Giant Robots Smashing Into Other Giant Robots

We are thrilled to announce the third session of our new Incubator Program. If you have a business idea that involves a web or mobile app, we encourage you to apply to our eight-week program. We'll help you validate your market opportunity, experiment with messaging and product ideas, and move forward with confidence toward an MVP. Learn more and apply at tbot.io/incubator. We look forward to seeing your application in our inbox! __ Co-host Will Larry interviews Stephen Hanson, the Director of Mobile Development at thoughtbot. The two explore the complexities of mobile app development, focusing on the advantages and disadvantages of React Native and Flutter. Stephen, who initially started as a full-stack web developer specializing in Enterprise Java, discusses React Native's cost-effectiveness and the convenience of having a unified codebase for iOS and Android platforms. However, he notes that Flutter might be a more suitable choice for high-performance needs. Both hosts emphasize the nuances of the mobile ecosystem, covering topics like in-app purchases, push notifications, and the strict guidelines set by app stores like Apple's. They agree that a comprehensive understanding of these aspects is crucial for an entire development team, including designers and project managers. Additionally, Stephen shares that the driving force behind his career is the opportunity to create apps that enhance people's lives. Stephen wraps up the discussion by detailing thoughtbot's goals of improving mobile development practices within the company and the broader developer community. __ React Native Flutter Follow Stephen Hanson on LinkedIn. Visit his website: shanson.co. Follow thoughtbot on X or LinkedIn. Become a Sponsor of Giant Robots! Transcript: WILL: This is the Giant Robots Smashing Into Other Giant Robots Podcast, where we explore the design, development, and business of great products. I'm your host, Will Larry. And with me today is Stephen Hanson, Director of Mobile Development here at thoughtbot. Stephen, thank you for joining me. STEPHEN: Hi, Will. Thanks for having me. I'm excited to be here. WILL: Yeah. I'm excited to talk about mobile development. But before we get started, tell us a little bit about who Stephen Hanson is: your personal life. STEPHEN: You know this because we often talk about our families when we get together. But I have two young kids, two and four years old. When you say personal life to anybody who has young kids, that's what we're talking about. [laughter] WILL: Yes. STEPHEN: So, they're keeping me busy but in the best way. WILL: Yeah, definitely. And I totally understand that. So, I know we talk about this often, but you like to woodwork. You like to work with your hands like most of us in tech. Like, we think so much with our head and mental that we try to find something to do physically, and yours is woodworking. Tell me a little bit about that. STEPHEN: Yeah. I think it's exactly what you said. I think working on a computer all day, you know, many years ago, I was like, what's something I can do with my hands, right? Something a little more physical. So yeah, fine woodworking has been a hobby of mine for quite a few years. And we were even chatting the other day about, you know, I'm trying to take time during the day to sneak out to the garage for 15 minutes, you know, during my lunch break or whatever to just get that mental reset and just work on something. WILL: Yeah. I know that you built your office that you work out of. I've been wanting to ask you, one, how did you do it? Two, how did you have the confidence to do it [laughter] to make sure that it was going to...how can I say this? I would be afraid that would it still be standing [laughter] after a little bit? [laughs] STEPHEN: Yeah, to be honest, that was definitely a fear. Yeah, I built my office in 2020, you know, COVID hit. All of a sudden, I was working fully remote. And we had another kid on the way. You know, we didn't have space in the house. So, I was like, what am I going to do? [laughs] I was already doing woodworking, but I didn't have any construction or carpentry experience. So, yeah, I definitely had the confidence issue. And I think, you know, I was just like, I don't know, let's just give it a try. [laughter] That's really all I can say. I didn't have the skills yet. But I watched a lot of YouTube and read a lot of [laughs] forums or, you know, just found info wherever I could, so...[laughs] WILL: Yep. And it's still standing today, correct? [laughs] STEPHEN: Correct. Yeah. [laughs] No, I'm just sitting in, like, a pile of rubble right now. [laughter] WILL: That's awesome, yeah. It's kind of like development sometimes for me. Like, you just got to take that leap sometimes, so... STEPHEN: You do, right? It's like, you know, fake it till you make it. [laughter] WILL: Yep. That's awesome. Awesome. Awesome. So, tell us a little bit about how did you get started in development in general? And then, how did you get started in React Native? STEPHEN: Yeah. So, I started out as a full-stack web developer. So, I didn't initially set out and say, "I'm going to build mobile apps," right? And I started out in 2011. I was working in Enterprise Java. I worked for American Airlines for a couple of years, and then I did enterprise consulting. I eventually made my way to, like, Rails and front-end development. And around 2016, 2017, I was freelancing. And eventually, clients started asking me to build mobile apps. [chuckles] WILL: [inaudible 04:16] STEPHEN: And I didn't know how to build mobile apps. So, I did what any web developer would do who doesn't build apps, and I used web technology. So, those first couple of apps that I built were hybrid apps. I used Ionic. And those are, you know, web apps that you package in a Native Wrapper. So, developing these apps, I literally developed them in a browser, right? And they're web apps. [laughs] And that was my first experience building apps. Even if they were web-based, I still had to work with the native app stores and learn, you know, app review guidelines and implement some native functionality, even though it was through, like, the Ionic wrappers. You know, people kind of trash on hybrid apps, and sometimes for good reason. But that wasn't a bad first experience for me or outcome, honestly. The clients were happy. They had apps in the app stores that were working for a pretty reasonable development cost. So yeah, that was my first experience in mobile. The end result isn't something I'd be necessarily proud of today. [laughs] WILL: I think that's all devs. [laughs] STEPHEN: Yeah, you know, [laughter] yeah, I -- WILL: Looking back at their work, yeah. [laughs] STEPHEN: I was talking about that. I could look back to something I built a month ago. [laughs] WILL: Yes. [laughter] STEPHEN: You don't have to go back far. [laughter] WILL: Yeah, so true [laughs]. You started working with the client when you were freelancing. So, how did you go from the hybrid web apps to actually saying, okay, I want to change, and I want to go all in on React Native? STEPHEN: React Native came out around that same time I was building those hybrid apps. So, the hybrid apps were 2016, 2017. React Native came out in 2015. So it was out, but it was still pretty new. And I was really interested in React Native right from the beginning, but I was also a little intimidated by it [chuckles]. So, when those first clients came to me for mobile apps, I didn't feel confident enough to say, "Yes, I can build you a React Native app." But a year or two later, I was working for another client on their Rails app. And I was building an API for their new React Native app. You know, I was really interested in React Native. So I said, "Hey, [chuckles] why don't I help out on the app side, too?" And they were like, "Sure, that sounds great." So that was kind of where I got my foot in the door with React Native. And then more opportunities like that just kept popping up over the next year. So, I got to work on a couple of other React Native apps. And like we talked about, I just started calling myself a React Native developer [laughs]. The rest is history. WILL: Yep. So true. We'll touch more on that later. But what would you say to a client who is trying to figure out if they should build native versus React Native? STEPHEN: There's a few things to consider when making that decision. But I think, usually, what I've seen is it comes down to budget and user experience. The bottom line is React Native is going to be a lot cheaper. You're basically building one app instead of two, right? Most of your code in a React Native app is going to be in JavaScript, and you can reuse all of that code across Android and iOS. If you're building a native app, you're just building two completely separate apps. So, it's just going to be cheaper to build that React Native app, and a lot of times, that's what it comes down to. For most companies, it can be really hard to justify that extra cost of building a completely native app for each platform. But then the question is when we talk about how can you justify the cost? Well, what would justify the cost, right? [laughs] I think probably the biggest trade-off when you build a React Native app versus a purely native app is there is a little bit of a performance penalty by building in React Native versus native. So, I think apps that will need to have a very flashy cutting-edge experience with lots of user-driven animation and effects, you know, when you get into that domain, I think that's where we see pure native starting to make more sense. But most apps and users would never feel that performance penalty of React Native. So, for most apps, that's not really something that enters into the equation. WILL: I want to dig into something you said. You were talking about if you do go native, you usually have to build an iOS and an Android separately. But with React Native, you could do it together. So, for someone who's maybe never done either one of them, can you kind of dig into, like, what does that look like? So, when you say I have to build an iOS and an Android portion versus I can do one codebase for React Native, can you walk us through kind of what that looks like, just a sample feature? STEPHEN: When I say React Native is a single codebase and, you know, native apps, you're building two apps, the way React Native works is you're basically building a React app. So, all of your business logic is going to be in React. And when your React code renders some UI, that gets translated into native UI. But your business logic is still going to be living in that JavaScript React app. So, one, when I say performance penalty, that's what I'm talking about is: there's a little bit of a performance penalty communicating back and forth between your JavaScript thread and the native system thread. But when we talk about one codebase versus two, that's what a React Native app looks like. You basically are working on a React app. It's one codebase with one set of business logic. And when you say, "Show a modal on the screen," that gets translated into a native Android modal or a native iOS modal, but in your code, you're just saying, "Show a modal." [laughs] So, you're just writing that one time. So yeah, a React Native project is just one codebase. Now, one thing that we haven't really touched on is in a React Native app, you do have the ability to drop down into native code. So, you have access to the native Android project and the native iOS project in your React Native app. So, you can write completely native code if you want to. But the appeal of React Native is you don't have to, you know, unless you get into one of those situations where you need to do something native that isn't supported out of the box with React Native or by an existing third-party library, or you want to have a very performant, very interactive part of your app. Maybe there's a reason you want to do that in native. You know, you do have that option in a React Native app of dropping down into that native code level. But to contrast that with a purely native project, you will have two completely separate codebases, one for Android and one for iOS. You'll have a development team for Android and a development team for iOS, you know, typically with different skill sets. The Android project will be Java, Kotlin. And your iOS project is swift. So, just in every sense, you really have two different projects when you're working on a purely native app. WILL: Okay, yeah, that makes sense. So like, for React Native, that show modal is just however many lines to show that one modal, and it does it for iOS and Android. But when you talk about native, you're saying that; however, iOS says to show that modal, you have to do it that way. But then Android, you also have to do it the Android way. And one developer, unless they know both of them, may not be able to handle both for those cases, correct? STEPHEN: Yeah, exactly. React Native abstracts away those underlying platforms. So, you really just need to know React Native for most cases. Though, there's definitely a benefit of knowing the underlying platforms. WILL: Definitely. Especially, like you touched on if you wanted to go into that native portion to add in a feature. You know, for example, I know we both worked on a project where we had a scanning app. And we had to tap into that native portion and React Native in order to get the scanning app to work, correct? STEPHEN: Yeah, that's right. We had to support some barcode scanning devices and hook into those barcode scanning frameworks that were proprietary [chuckles] to those devices. So yeah, we had to build native modules for Android and iOS to support those. WILL: Gotcha. Okay. I want to touch back on something you said earlier about the flashy experiences. You said sometimes you may not see it or whatever, but sometimes, if you want that flashy experience, it's better to go the native route. Can you explain that a little bit more? STEPHEN: So yeah, it's kind of what I was touching on a second ago. You know, in a React Native app, you have the JavaScript thread that is always running and coordinating UI changes with business logic. So, you've got your business logic in JavaScript. You've got the UI in native. And those need to be coordinated to interact. So, that's kind of where that performance penalty can happen. You know, again, most apps and users would never feel this penalty. I've never been, like, using my phone and been like, oh, this is a React Native app; I can feel it, you know. [laughs] It's not something that typically enters the picture for most apps that we work on. But there are certain types of apps that might be more important, you know, highly interactive games or things that just need to have that extra flashiness and interactive flashiness specifically, where it could make sense to build that natively. Another interesting thing in the React Native space is React Native recently re-architected their rendering engine to be written in C++ and be more efficient. So, this performance overhead might be a little bit less of a trade-off. They've re-architected the way that React Native JavaScript talks to the native layer, which might make this even less of an issue going forward. WILL: I looked it up for the podcast. But do you know some of the companies that we probably are familiar with, like they built apps on React Native? Can you name a couple? STEPHEN: Yeah, I was recently looking at this, too. And, you know, the big one is Facebook, right? Facebook built React Native. So, they're the sponsor of that project. So, Facebook and Facebook Messenger, I believe those apps are built with React Native. I don't know if the entire apps are or not [chuckles]. Do you know by chance? [laughs] WILL: React Native on their website says, "Hey, we're going to showcase these apps that they're built in React Native." So, I'm guessing a huge portion of it was built in React Native, so... STEPHEN: Yeah. That's a good point. Yeah, you're right. They're showcasing it there. So yeah, you know, other ones, you know, lots of brands, Shopify, looks like PlayStation. I'm looking at the list now on the React Native website: Pinterest, Flipkart, Discord, Walmart, Tesla, Coinbase, Mercari. Yeah, I mean, it's just a lot of big-name apps built in React Native, including quite a few that we've [laughs] that we've built. [laughter] MID-ROLL AD: Are you an entrepreneur or start-up founder looking to gain confidence in the way forward for your idea? At thoughtbot, we know you’re tight on time and investment, which is why we’ve created targeted 1-hour remote workshops to help you develop a concrete plan for your product’s next steps. Over four interactive sessions, we work with you on research, product design sprint, critical path, and presentation prep so that you and your team are better equipped with the skills and knowledge for success. Find out how we can help you move the needle at tbot.io/entrepreneurs. WILL: If I'm absolutely sold on getting that flashy experience, is native the only route to go? STEPHEN: I think until pretty recently, that would have been your option [laughs]. But Flutter has been picking up a little bit of momentum. So, Flutter is developed by Google. And it's kind of a challenger in that React Native space. It kind of has the same write once, run anywhere, you know, philosophy as React Native. You have one codebase. But they tout kind of being a more performant option than React Native. So, it compiles down to native ARM or Intel code, which can give better performance without, you know, not needing that JavaScript bridge kind of handling that communication between the UI and the business logic. WILL: So, when would you use Flutter versus React Native? STEPHEN: I kind of keep going back to, like, you know, we talk about the performance overhead of a React Native app. I don't think that's even on the map for the vast majority of apps. Like, this isn't a performance penalty that you can typically feel. So, looking at Flutter versus React Native, React Native has several advantages. I think the biggest one is it's React. So, every team has React developers already on the team, pretty much nowadays. So, you know, if you've got an organization that says, "Oh, we need to build a mobile app," they probably already have a team of React developers somewhere working on their web app [laughs]. So, there's a big benefit of kind of centralizing their team around that technology. You know, you can have a little bit of cross-pollination between web and mobile, which can be really nice. I think, similarly, it's a lot easier to find and hire React or React Native developers right now than it is to find and hire Flutter developers. So, Flutter is written in Dart, and it has its own front-end framework. So, this isn't necessarily a technology that you're going to have on your existing team. Like, I've never worked with Dart, personally. It's not nearly as common as React developers. You know, that, to me, is going to be a big downside. You know, the talent pool is a lot smaller for Flutter/Dart developers. Also, the ecosystem with Flutter being newer, it's not as established. It doesn't have as large of an ecosystem as React Native. So, for those reasons, I think React Native is still, at least for us, like, it's usually where we would steer a client over Flutter, unless they're in that category of, like, they're really going for something, you know, groundbreaking. And, you know, the choice is either, you know, they've ruled out React Native. They need to get that native performance, and maybe they could achieve that with Flutter, and maybe Flutter would be a good option then. WILL: Okay. You mentioned that—and I agree with you—like, you probably have some React devs on your team somewhere. Most companies does. So, say if I am bought in, I'm going all in on React Native, and I have React web developers on my team. Is that an easy transition for those developers, or what does that transition look like? STEPHEN: Yeah, this is something...I think you and I have talked about this a lot because we both transitioned from React Web to React Native. And, you know, it wasn't all that easy, right? [laughs] WILL: No, it was not [laughter] at all. [laughter] STEPHEN: So yeah, you know, it is a fallacy to say, "Hey, we've got a React team, you know, let's just start tomorrow on building an app, and it'll be smooth sailing. And, you know, no one needs to learn anything, and we'll be good to go," right? [laughs] So, you know, what I always say is a React web developer can successfully work on a React Native app. But I don't think they have the skills yet to lead that initiative because there's just so much to the mobile ecosystem that needs to be learned. And really, you know, my first couple of React Native apps, I wasn't the lead developer. There was somebody on those projects who really knew that space better than I did. And that was really helpful for me to have. How about you? What about your first, like, React Native project? What did that look like? WILL: It was at another company, and the exact words paraphrasing was, "You know React, so you can easily work on React Native." And so, I got on the project. And I really struggled, to be honest with you, because there's a lot of things that I didn't know: in-app purchases, push notifications, how to deal with Apple store, Android store, deploying to those stores. Like all of those things, navigation is totally different than React navigations and routes. It was a lot. It was a lot more than they led on to what it was. Eventually, I caught on. It took me a while. I needed to work with some more senior React Native developers, and I was able to really pick it up. But yeah, it was tough. I'll be honest: I struggled for a while because I went in feeling like I should have known all those things because that's the way it was conveyed to me. Now that I look back on it I was like, there's no way I could have known those things. It's just a different language. So, I had to get in there and learn it. And I even...I'm trying to think I've learned a couple of new languages. But it's almost like learning a new language just with, you know, the, like I mentioned, the in-app purchases, push notifications. It's just totally different. STEPHEN: Yeah, that's been my experience also. I think the challenges weren't, like, coding [laughs] because, you know, building a React Native app is coding in React. The challenges that I faced were, like you said, it's just the mobile ecosystem and learning all the intricacies, the functionality that users have come to expect in mobile apps, you know, like password manager, integration, and background execution modes, and deep linking strategies, all that kind of stuff. You know, if you don't know what questions to ask or what features to be thinking of, it's just really hard. And [laughs] I think it's more than just the developer needing to know that too. I think anytime it comes, you know, down to building an app, the whole team needs to have that mobile background. It's just a completely different platform than building for the web, right? So like, product owners, project managers, designers, developers all need that context so we can be prioritizing the right features and building a UI that matches the patterns that people have come to expect in a mobile app. And then, of course, developing those apps using the, you know, the proper native modules. WILL: Yeah, definitely. And I [chuckles]...you mentioned that it's mostly on, like, the mobile side. I don't know the best way to say that. But, like, I can tell you, when I first got onto the React Native project, there were numerous features that I could implement, and to a certain point to where I had to go that mobile. So, like, I was like, oh yeah, I can learn these new components that's in React Native. Okay, I got it to work. It's finished. You know, my PM would be like, "Well, it's not completely finished because you have to deploy it." And I was like, oh, I have no idea what I'm doing now. Like, I just know [laughs]...I know up to this point. STEPHEN: [laughs] WILL: But anything over that, I'm like, yeah, I have no idea. STEPHEN: Especially with consulting, right? With consulting, you need even more expertise, right? The clients are counting on you to build their app. And that's where, you know, having that deep, deep familiarity where you can say to a client, "This is how we're going to do the deployment process, you know, and I need, you know, X, Y, and Z to help set it up. And here are the deliverables, and here's when we'll have it," that kind of thing. Like, it really takes it up a whole nother notch what you need to know. WILL: Definitely, yeah. Because I think compared to mobile, I feel like web development can almost be like the Wild Wild West. And what I mean by that is, like, there's no rules for you to push out a website in web. Like, you know, you build it. You push it out. It can be out there, you know. Whoever is hosting it, unless you go against their rules, maybe, but their rules are very relaxed and stuff like that. Mobile, there's a totally different set of rules. Because, like, I was laughing not too long ago. There was rumors that Elon Musk was going to remove the blocking feature on Twitter [chuckles]. And it was funny because all the mobile devs they came out. And if you're a mobile dev, you know this. Apple is very strict. STEPHEN: [laughs] WILL: If this is a social media app that you're building, you have to have that blocking feature, which I agree it needs to be there. But it's funny, like, all the mobile devs was like, yeah, that's not going to work. Good luck [chuckles]. Good luck being an app again. STEPHEN: Yeah, [laughs] good luck. WILL: Like, they're going to kick it off. And yeah, they're very big on kicking it off if it doesn't follow those rules and things like that. So yeah, for React Native, you have to learn those rules, or, like I said, they won't approve it. They won't push it out to their store. STEPHEN: Yep, exactly. Yeah. I feel like the new one at every client project; I have to say, "We have to offer a way to delete your account in the app," because [laughs] that's a new one that launched last year, and I think has just started being enforced more recently. Like, all those little gotcha rules, you know, like, if you don't know about that, then you're going to go to submit your app to the stores, and you're going to get rejected every single time. [laughs]. WILL: And they're not shy about rejecting you [laughs]. STEPHEN: Yeah. But I would say, like, a lot of the rules, I'm like, yes, this is amazing that we have these rules, you know. It does help keep the community safer like things like blocking. But then there's the other rules of, like, Apple's like, hey, you've got to use our payment system and pay us 30% of every sale. WILL: Yes [laughs]. STEPHEN: I was, like, you know, there's some evil stuff happening there, too. WILL: I totally agree. And we ran into that issue. We had an app that used Stripe. And we actually had to remove it in order to use in-app purchases because...I forgot the rules around it, but it was essentially for digital content. I think it's what it was. And so, we had to use Apple's in-app purchases. So yeah, I totally agree with you on that. STEPHEN: Yeah. I feel like I've been a part of so many apps where we're, like, reading those rules. And we're like, okay, you know, it's like, we're watching a live stream of birds. WILL: [laughs] STEPHEN: You know, like, the birds aren't digital [laughter], you know. It's like, [laughs] where does this fall in the rule? [laughs] WILL: Yes [laughs]. I've done that, too [laughter]. Yep. It's almost like, you know, I feel like lawyers, okay, like, is this what this rule is, or the law what is written, or does this fall underneath that? So yeah, totally, totally agree. STEPHEN: Yep [laughs]. WILL: So, you've been here a couple of years at thoughtbot. What has been your experience building React Natives here for clients at thoughtbot? STEPHEN: Yeah, yeah. I've been at thoughtbot for about five years now. And I have been building React Native apps that whole time. And, I mean, I started at thoughtbot a little more in the full-stack space, web development, and have transitioned to where I'm mostly only building React Native mobile apps now. It's been a great experience. I think that React Native is really a sweet spot of; we're able to build these apps really efficiently and much less expensively than when we're doing pure native. And the end product is a really good app. So, it's been a great experience, you know, React Native is really...it has a really nice development experience. You know, it's the JavaScript React ecosystem. And we use TypeScript, and we have a really good developer experience with it. And then we're building apps that clients are really happy with and with a good budget. So, I think it's kind of that, you know, like, win-win-win kind of scenario where everybody is happy. And yeah, I don't see it going anywhere. And I think we're going to be building React Native apps for quite a while to come. WILL: Yeah, I totally agree with that. Where do you see React Native and mobile dev going here at thoughtbot in the next six months or even the next year? What are your goals for the mobile team? STEPHEN: We've got a couple of goals. One of them is around kind of what we've talked about with the mobile space in general. This isn't really specific to React Native, but it can be. But, consulting in the mobile space is challenging because there's a lot of mobile-specific domain knowledge that a team really needs to have. So, that's something that we've started looking into is, like, how do we build up our resources internally and then, hopefully, externally as well to help guide us on our projects and ensure that we have, like, you know, we are developing apps consistently and efficiently every time? So, that's something we're looking into is, like resources to help our teams—not just developers, but project managers, designers, and developers—help us navigate the mobile space. Okay, you're going to do push notifications. Here's the library we use. Here's things to think about, and interactions to think about, and iOS-specific functionality that we could support, and Android-specific functionality that we can support. You know, you're going to do deep linking; do you want to use universal links, or do you want to use a different strategy, a scheme-based link? So, basically, building up that set of resources so that our teams are all able to consult and build efficiently and consistently across the board. So, that's kind of goal number one. And then, goal number two is to kind of bring some of that out into the community a little bit more. So, thoughtbot is very well known in the Rails space for all of the open-source content we've put out and blog posts, and courses, and books. I mean, there's just so much on the Rails side that thoughtbot has done. And we're just a little bit less mature on the React Native side in terms of what we've put out there. So, that's kind of the second goal is giving back, helping others kind of do that same thing. I feel like we have developed our practices internally, and we're building some great apps. And it's kind of time to contribute back a little bit more. WILL: Awesome. I'm looking forward to reaching those goals. If you can go back and give yourself advice, what would you tell yourself? STEPHEN: I would maybe say, read the documentation [laughs]. I don't know when I got into mobile; I think I just jumped in. And, you know, we've talked about some of the mobile-specific domain, and not knowing what you don't know, and app review guidelines. I feel like early on, I just responded to challenges as they came up, as opposed to just digging into, you know, Apple's documentation and Android's documentation and just really understanding the underlying operating systems in stores. That's probably a piece of advice. If I could go back, I would just start at the documentation, you know, go to developer.apple.com and read about all of the underlying APIs of StoreKit and, you know, associated domains and all of these sorts of things. Just learn 'em, and then you know 'em. [laughs]. So, maybe that could have saved me some heartache if I just was a little more intentional about, okay, I'm getting into app development. I'm going to set aside some time and just really learn this stuff, as opposed to kind of where I had one foot in the door, one foot out of the door for a while. And I think that kept me from just sitting down and really going deep. WILL: That's really good advice. Just read the documentation. And that's not just Apple. STEPHEN: [laughs] WILL: That's a lot of departments, sections of my life. So, yes, I like that. [laughter] STEPHEN: I actually...that's something I did early in my career. So, I started as an Enterprise Java developer in 2011, and I was using the Spring framework. I downloaded the entire PDF. It was, like, 250 pages, the documentation [laughs]. And I remember just being on, like, airplane flights, and I just read the documentation, just cover to cover. That served me so well. I was, like, the expert, you know [laughs]. I don't always do it, but when I do, I'm like, oh yeah, why didn't I do that sooner? [laughs] WILL: Yeah, totally agree. I like that. What is the wind in your sails? What motivates Stephen? STEPHEN: Like, I think what attracted me to software development is just being able to build stuff, you know, probably the same thing that attracted me to woodworking. So, I think what motivates me is that prospect of, hey, I'm building an app that people are going to use, and it's going to make their life better. So, that's really what gets me up and gets me motivated. It's less so the actual coding, to be honest. It's really the prospect of, like, hey, I'm building something. WILL: Awesome. Yeah. Is there anything that you would like to promote? STEPHEN: If you're interested in building a mobile app, come talk to us. We'd love to build your mobile app. Go to thoughtbot.com/hire-us; I believe hire-us. We would love to talk to you about your mobile project. So, don't hesitate to reach out. We'd love to hear about what you're interested in building. WILL: Awesome. Well, Stephen, it was great to chat with you. It's always great to chat with you about mobile development and just personal life things. So, I really appreciate you being on the podcast today. STEPHEN: Thanks for having me, Will. It was a lot of fun. Always good talking with you. WILL: You can subscribe to the show and find notes along with a complete transcript for this episode at giantrobots.fm. If you have any questions or comments, email us at hosts@giantrobots.fm. You can find me on Twitter @will23larry. ANNOUNCER: This podcast is brought to you by thoughtbot, your expert strategy, design, development, and product management partner. We bring digital products from idea to success and teach you how because we care. Learn more at thoughtbot.com.Special Guest: Stephen Hanson.Sponsored By:thoughtbot: Are you an entrepreneur or start-up founder looking to gain confidence in the way forward for your idea? At thoughtbot, we know you’re tight on time and investment, which is why we’ve created targeted 1-hour remote workshops to help you develop a concrete plan for your product’s next steps. Over four interactive sessions, we work with you on research, product design sprint, critical path, and presentation prep so that you and your team are better equipped with the skills and knowledge for success. Find out how we can help you move the needle at: tbot.io/entrepreneursSupport Giant Robots Smashing Into Other Giant Robots

Victoria and Will interview Rishi Malik, the Founder of Backstop.it and VP of Engineering at Varo Bank. They talk about Rishi's recent adventure at DEF CON, the renowned annual security conference that he's attended for six years, and describes how it has transformed from a mere learning experience into a thrilling competition for him and his team. The conference = their playground for tackling an array of security challenges and brain-teasing puzzles, with a primary focus on cloud security competitions. They talk about the significance of community in such events and how problem-solving through interaction adds value. Rishi shares his background, tracing his path from firmware development through various tech companies to his current roles in security and engineering management. The vital topic of security in the fintech and banking sector highlights the initial concerns people had when online banking emerged. Rishi navigates through the technical intricacies of security measures, liability protection, and the regulatory framework that safeguards online banking for consumers. He also highlights the evolving landscape, where technological advancements and convenience have bolstered consumer confidence in online banking. Rishi shares his unique approach to leadership and decision-making, and pearls of wisdom for budding engineers starting their careers. His advice revolves around nurturing curiosity and relentlessly seeking to understand the "why" behind systems and processes. __ Backstop.it Follow Backstop.it on X. Varo Bank Follow Varo Bank on Instagram, Facebook, X, YouTube, or LinkedIn. Follow Rishi Malik on LinkedIn. Follow thoughtbot on X or LinkedIn. Become a Sponsor of Giant Robots! Transcript: VICTORIA: This is the Giant Robots Smashing Into Other Giant Robots podcast, where we explore the design, development, and business of great products. I'm your host, Victoria Guido. WILL: And I'm your other host, Will Larry. And with us today is Rishi Malik, Founder of Backstop.it and VP of Engineering at Varo Bank. Rishi, thank you for joining us. RISHI: Thanks for having me. I'm excited to be here. VICTORIA: Yes, Rishi. I'm so excited to talk with you today about your security background and get into your role at Varo and Backstop IT. But first, I wanted to hear a little bit more about your recent experience attending DEF CON. How was that? RISHI: It was awesome. I do have quite the background in security at this point. And one of the things I started doing early on, as I was getting up to speed and learning more about the security-specific side of things, was beginning to attend DEF CON itself. So, I've now gone six years straight. And it started out as just kind of experiencing the conference and security and meeting folks. But it's progressed to where I now bring a team of people where we go and we compete. We have a good time. But we do get to kind of bring the security side of things into the software engineering and engineering leadership stuff that we all do on a day-to-day basis. VICTORIA: Yeah. And what kind of puzzles do you solve with your team when you attend DEF CON? RISHI: There's definitely a lot of variety there, which I think is part of the fun. So, DEF CON frequently has electronic badges, you know, with random puzzles on there that you have to solve. Some of it are cryptographic. Some of them are kind of random cultural things. Sometimes there's music challenges based around it. Sometimes, it's social and interactive. And you have to go find the right type of badge or the right person behind it to unlock something. So, all of those, you know, typically exist and are a ton of fun. Primarily, in the last few years, we've been focusing more on the cloud CTF. So, in this case, it's our team competing against other teams and really focused on cloud security. So, it's, you know, figuring out vulnerabilities in, you know, specially designed puzzles around AWS and GCP, the application side of things as well, and competing to see how well you can do. Three years ago, the last couple of years, we've not won it, but we've been pretty competitive. And the great thing is the field is expanding as more and more people get into CTF themselves but, more importantly, into cloud infrastructure and cloud knowledge there. So, it's just great to see that expansion and see what people are into, what people are learning, and how challenging some of these things can be. VICTORIA: I love the idea of having a puzzle at a conference where you have to find a specific person to solve it. And yeah, I'm always interested in ways where we can have these events where you're getting together and building community and growing expertise in a field but in a way that makes it fun [laughs] and isn't just life-draining long, like, talks about random stuff. RISHI: [laughs] I think what you're touching on there is crucial. And you said the word community, and, to me, that is, you know, a big part of what DEF CON and, you know, hacking and security culture is. But it is, I think, one of the things that kind of outside of this, we tend to miss it more, you know, specifically, like, focused conferences. It is more about kind of the content, you know, the hallway track is always a thing. But it's less intentional than I personally, at this stage, really prefer, you know. So, I do like those things where it is encouraging interaction. For me, I'd rather go to happy hour with some people who are really well versed in the subject that they're in rather than even necessarily listening to a talk from them on what they're doing. Simply because I think the community aspect, the social aspect, actually gets you more of the information that is more relevant to what you're doing on a day-to-day basis than just consuming it passively. VICTORIA: I agree because consuming it passively or even intentionally remotely, there are things that you didn't even think to think about [laughs] that aren't going to come up just on your own. You have to have another person there who's...Actually, I have a good friend who's co-working with me this week who's at Ticketmaster. And so, just hearing about some of the problems they have and issues there has been entertaining for me. So yeah, I love that about DEF CON, and I love hearing about community stories and fun ways that companies can get a benefit out of coming together and just putting good content out there. RISHI: Absolutely. I think problem-solving is where you get the most value out of it as a company and as a business. VICTORIA: Yeah, maybe that's a good segue to tell me a little bit more about your background and how you came to be where you are today. RISHI: Yeah. For me growing up, I was always that problem-solver type of person. So, I think that's what kind of naturally gravitated me towards tech and, you know, hardware and software engineering. You know, so, for me, I go back quite a while. I'd been doing a lot of development, you know, in the early days of my career. I started out doing firmware development back in the days of large tape libraries, right? So, if you think about, like, big businesses back before cloud was a big thing and even back before SSDs were a thing, you know, it was all spinning disks. It was all tape. And that's kind of the area that I started in. So, I was working on robots that actually move tapes around these giant tape libraries that are, you know, taller than I am that you can walk inside of because they're so big, for big corporations to be able to backup their data on an overnight basis. You have to do that kind of stuff. Then I started going into smaller and smaller companies, into web tech, into startups, then into venture-backed startups. And then, eventually, I started my own company and did that for a while. All of this is really just kind of, you know, software engineering in a nutshell, lots of different languages, lots of different technologies. But really, from the standpoint of, here's a whole bunch of hard problems that need to be solved. Let's figure out how we can do that and how we can make some money by solving some of these problems. That eventually kind of led me down the security path as well and the engineering management side of things, which is what I do now, both at Backstop...is a security consulting business and being VP of Engineering at Varo Bank. WILL: How was your journey? Because you started as an intern in 2003. RISHI: [laughs] WILL: And then, you know, 20 years later. So, how was your journey through all of that? [laughs] RISHI: [laughs] You know, I hadn't actually put it together that it has been 20 years this year until you said that. So, that's awesome. It's been a blast, you know. I can honestly say it's been wildly different than what I imagined 20 years ago and interesting in different ways. I think I'm very fortunate to be able to say that. When I started out as an intern in 2003, technologies were very different. I was doing some intern shifts with the federal government, you know, so the pace was wildly different. And when I think of where technology has come now, and where the industry has gone, and what I get to do on a day-to-day basis, I'm kind of just almost speechless at just how far we've come in 20 years, how easy some things are, how remarkably hard some other things are that should honestly be easy at this point, but just the things that we can do. I'm old enough that I remember cell phones being a thing and then smartphones coming out and playing with them and being like, yeah, this is kind of mediocre. I don't really know why people would want this. And the iPhone coming out and just changing the game and being like, okay, now I get it. You know, to the experience of the internet and, you know, mobile data and everywhere. It's just phenomenal the advances that we've had in the last 20 years. And it makes me excited for the next 20 years to see what we can do as we go forward. VICTORIA: I'm going to take personal offense to someone knowing that technology being too old [laughs], but, yeah, because it really wasn't that long ago. And I think one thing I always think about having a background in civic tech and in financial tech as well is that the future is here; it's just not evenly distributed. So, now, if you're building a new company, of course, the default is to go straight to the cloud. But many companies and organizations that have been around for 60-80 years and using the internet right when it first came out are still in really old technologies that just simply work. And maybe they're not totally sure why, and change is difficult and slow. So, I wonder if you have any experience that you can take from the banking or fintech industry on how to make the most out of modern security and compliance platforms. RISHI: Yeah, you know, I think most people in tech especially...and the gray hairs on me are saying the younger folks in tech especially don't realize just how much older technologies still exist and will exist for quite some time. When you think of banking itself, you know, most of the major companies that you can think of, you know, in the U.S. especially but kind of across the world that are the top tier names of banks, and networks, and stuff like that, still run mainframes. When you swipe your credit card, there's a very good chance that is processed on a mainframe. And that's not a bad thing. But it's just, you know when you talk to younger engineers, it's not something that kind of crosses their mind. They feel like it is old-tech. The bulk of businesses don't actually run on the cloud. Having been through it, I've racked and stacked servers and had to figure out how to physically take hardware across, you know, country borders and things like those lines. And now, when I do want to spin up a server somewhere else, it's just a different AWS region. So, it's remarkably easy, at this point, to solve a lot of those problems. But once you're up and live and you have customers, you know, where downtime is impactful or, you know, the cost of moving to the cloud or modernizing your technology is substantial, things tend to move a lot slower. And I think you see that, especially when it comes to security, because we have more modern movements like DevOps bringing security into it. And with a lot of the, you know, the modern security and compliance platforms that exist, they work very, very well for what they do, especially when you're a startup or your whole tech stack is modernized. The biggest challenges, I think, seem to come in when you have that hybrid aspect of it. You do have some cloud infrastructure you have to secure. You do have some physical data centers you have to secure. You have something that is, you know, on-premise in your office. You have something that is co [inaudible 10:01] somewhere else. Or you also have to deal with stuff like, you know, much less modern tech, you know, when it comes to mainframes and security and kind of being responsible for all of that. And I think that is a big challenge because security is one of those things where it's, you know, if you think of your house, you can have the strongest locks on your door and everything else like that. But if you have one weak point, you have a window that's left open, that's all it takes. And so, it has to be all-inclusive and holistic. And I think that is remarkably hard to do well, even despite where technology has come to these days. WILL: Speaking of securities, I remember when the Internet banking started a couple of years ago. And some of the biggest, I guess, fears were, like, the security around it, the safety. Because, you know, your money, you're putting your money in it, and you can't go to a physical location to talk to anyone or anything. And the more and more you learn about it...at first, I was terrified of it because you couldn't go talk to someone. But the more and more I learned about it, I was like, oh, there's so much security around it. In your role, what does that look like for you? Because you have such a huge impact with people's money. So, how do you overcome that fear that people have? RISHI: There's, I think, a number of steps that kind of go into it. And, you know, in 2023, it's certainly a little bit easier than it used to be. But, you know, very similar, I've had the same questions, you know, and concerns that you're describing. And I remember using one of the first banks that was essentially all digital and kind of wondering, you know, where is my money going? What happens if something goes wrong? And all of those types of things. And so, I think there is kind of a number of different aspects that go into it. One is, you know, obviously, the technical aspects of security, you know, when you put your credit card number in on the internet, you know, is it encrypted? You know, is it over, you know, TLS? What's happening there? You know, how safe and secure is all that kind of thing? You know, at this point, pretty much everyone, at least in the U.S., has been affected by credit card breaches, huge companies like Home Depot and Target that got cards accessed or, you know, just even the smaller companies when you're buying something random from maybe something...a smaller website on the internet. You know, that's all a little bit better now. So, I think what you have there was just kind of a little bit of becoming comfortable with what exists now. The other aspect, though, I think, then comes into, well, what happens when something goes wrong? And I think there's a number of aspects that are super helpful for that. I think the liability aspect of credit card, you know, companies saying, you know, and the banks "You're not liable for a fraudulent transaction," I think that was a very big and important step that really helps with that. And on top of that, then I think when you have stuff like the FDIC, you know, and insurance in the U.S., you know, that is government-backed that says, you know what? Even if this is an online-only digital bank, you're safe. You're protected. The government's got your back in that regard. And we're going to make sure that's covered. At Varo, that's one of the key things that we think about a lot because we are a bank. Now, most FinTechs, actually, aren't banks, right? They partner with other third-party banks to provide their financial services. Whereas at Varo, we are federally regulated. And so, we have the full FDIC protection. We get the benefits of that. But it also means that we deal with the regulation aspects and being able to prove that we are safe and secure and show the regulators that we're doing the right things for our customers. And I think that's huge and important because, obviously, it's safety for customers. But then it changes how you begin to think about how you're designing products, and how you're [inaudible 13:34] them, and, you know, how you're marketing them. Are we making a mobile app that shows that we're safe, and secure, and stable? Or are we doing this [inaudible 13:42] thing of moving too fast and breaking things? When it's people's money, you have to be very, very dialed into that. You still have to be able to move fast, but you have to show the protection and the safety that people have because it is impactful to their lives. And so, I think from the FinTech perspective, that's a shift that's been happening over the last couple of years to continue that. The last thing I'll say, too, is that part of it has just come from technology itself and the comfort there. It used to be that people who were buying, you know, items on the internet were more the exception rather than the rule. And now with Amazon, with Shopify, with all the other stuff that's out there, like, it's much more than a norm. And so, all of that just adds that level of comfort that says, I know I'm doing the right things as a consumer, that I'm protected. If I, you know, do have problems, my bank's got my back. The government is watching out for what's happening and trying to do what they can do to regulate all of that. So, I think all of that has combined to get to that point where we can do much more of our banking online and safely. And I think that's a pretty fantastic thing when it comes to what customers get from that. I am old enough that I remember having to figure out times to get to the bank because they're open nine to five, and, you know, I have to deposit my paycheck. And, you know, I work nine to five, and maybe more hours pass, and I had no idea when I can go get that submitted. And now, when I have to deposit something, I can just take a picture with my phone, and it safely makes it to my account. So, I think the convenience that we have now is really amazing, but it has certainly taken some time. And I think a number of different industry and commercial players kind of come together and make that happen. MID-ROLL AD: Now that you have funding, it's time to design, build, and ship the most impactful MVP that wows customers now and can scale in the future. thoughtbot Liftoff brings you the most reliable cross-functional team of product experts to mitigate risk and set you up for long-term success. As your trusted, experienced technical partner, we'll help launch your new product and guide you into a future-forward business that takes advantage of today's new technologies and agile best practices. Make the right decisions for tomorrow today. Get in touch at thoughtbot.com/liftoff. VICTORIA: I appreciate that perspective on approaching security from the user experience of wanting safety. And I'm curious if we can talk in contrast from that experience to the developer experience with security. And how do you, as a new leader in this financial product company, prioritize security and introduce it from a, like, building a safety culture perspective? RISHI: I think you just said that very eloquently. It is a safety culture. And cultural changes are hard. And I think for quite some time in the developer industry, security was either an afterthought or somebody else's problem. You know, it's the security team that has to think about it. It's, you know, and even these days, it's the red team that's going to go, you know, find these answers or whatever I'm shipping as a developer. My only thing to focus on is how fast I can ship, or, you know, what I'm shipping, rather than how secure is what I'm shipping. And so, I think to really be effective at that, it is a cultural shift. You have to think and talk about security from the outset. And you have to bake those processes into how you build product. Those security conversations really do need to start at the design phase. And, you know, thinking about a mobile app for a bank as an example, you know, it starts when you're just thinking about the different screens on a mobile app that people are going to go through. How are people interpreting this? You know, what is the [inaudible 17:23], and the feeling, and the emotions, that we're building towards? You know, is that safe and secure or, you know, is it not? But then it starts getting to the architecture and the design of the systems themselves to say, well, here's how they're going to enter information, here's how we're passing this back and forth. And especially in a world where a lot of software isn't just 100% in-house, but we're calling other partners for that, you know, be it, you know, infrastructure or risk, you know, or compliance, or whatever else it may be, how are we protecting people's data? How are we making sure our third parties are protecting people's data? You know, how are we encrypting it? How are we thinking about their safety all the way through? Again, even all the way down to the individual developer that's writing code, how are we verifying they're writing good, high-quality, secure code? Part of it is training, part of it is culture, part of it is using good tooling around that to be able to make sure and say, when humans make mistakes because we are all human and we all will make mistakes, how are we catching that? What are the layers do we have to make sure that if a mistake does happen, we either catch it before it happens or, you know, we have defense in depth such that that mistake in and of itself isn't enough to cause a, you know, compromise or a problem for our customers? So, I think it starts right from the start. And then, every kind of step along the way for delivering value for customers, also let's add that security and privacy and compliance perspective in there as well. VICTORIA: Yes, I agree. And I don't want to work for a company where if I make a small human mistake, I'm going to potentially cost someone tens or however many thousands of dollars. [laughs] WILL: I have a question around that. How, as a leader, how does that affect you day to day? Because I feel like there's some companies, maybe thoughtbot, maybe other companies, that a decision is not as critical as working as a bank. So, you, as a leader, how do you handle that? RISHI: There's a couple of things I try and consider in any given big or important decision I have to make, the aspects around, like, you know, the context, what the decision is, and that type of stuff. But from a higher level, there's kind of two things I try and keep in mind. And when I say keep in mind, like, when it's a big, impactful decision, I will actually go through the steps of, you know, writing it down or talking this out loud, sometimes by myself, sometimes with others, just, again, to make sure we are actually getting to the meat of it. But the first thing I'm trying to think of is kind of the Amazon idea of one-way versus two-way doors. If we make this decision and this is the wrong decision, what are the ramifications of that? You know, is it super easy to undo and there's very little risk with it? Or is it once we've made this decision or the negative outcome of this decision has happened, is it unfixable to a certain degree? You know, and that is a good reminder in my head to make sure that, you know, A, I am considering it deeply. And that, B, if it is something where the ramifications, you know, are super huge, that you do take the time, and you do the legwork necessary to make sure you're making a good, valid decision, you know, based on the data, based on the risks involved and that there's a deep understanding of the problem there. The second thing I try to think of is our customers. So, at Varo, our customers aren't who most banks target. A lot of banks want you to take all your money, put it in there, and they're going to loan that money out to make their money. And Varo is not that type of bank, and we focus on a pretty different segment of the market. What that means is our customers need their money. They need it safely and reliably, and it needs to be accurate when they have it. And what I mean by that is, you know, frequently, our customers may not have, you know, hundreds or a thousand dollars worth of float in their bank accounts. So, if they're going and they're buying groceries and they can't because there's an error on our side because we're down, and because the transactions haven't settled, then that is very, very impactful to them, you know, as an individual. And I think about that with most of these decisions because being in software and being in engineering I am fortunate enough that I'm not necessarily experiencing the same economic struggles that our customers may have. And so, that reminder helps me to think about it from their perspective. In addition, I also like to try and think of it from the perspective...from my mom, actually, who, you know, she is retired age. She's a teacher. She's non-technical. And so, I think about her because I'd say, okay, when we're making a product or a design decision, how easy is it for her to understand? And my biases when I think about that, really kind of come into focus when I think about how she would interpret things. Because, you know, again, for me, I'm in tech. I think about things, you know, very analytically. And I just have a ton of experience across the industry, which she doesn't have. So, even something as simple as a little bit of copy for a page that makes a ton of sense to me, when I think about how she would interpret it, it's frequently wildly different. And so, all of those things, I think, kind of come together to help make a very strong and informed decision in these types of situations where the negative outcomes really do matter. But you are, you know, as Varo is, you're a startup. And you do need to be able to build more products quickly because our customers have needs that aren't being met by the existing banking industry. And so, we need to provide value to them so that their lives are a bit better. VICTORIA: I love that focus on a specific market segment and their needs and solving for that problem. And we know that if you're at a certain income level, it's more expensive [laughs] because of the overdraft fees and other things that can cause you problems. So, I really appreciate that that's the mission at Varo, and that's who you're focusing on to create a better banking product that makes more sense. I'm curious if there were any surprises and challenges that you could share from that discovery process and finding out, you know, exactly what were those things where your mom was, like, uh, actually, I need something completely different. [laughs] RISHI: Yeah, so, [chuckles] I'm chuckling because, you know, it's not, like, a single kind of time or event. It's, you know, definitely an ongoing process. But, you know, as actually, we were talking, you know, about earlier in terms of being kind of comfortable with doing things digital and online, that in and of itself is something that even in 2023, my mom isn't as comfortable or as confident as, you know, say, maybe the three of us are. As an example, when sending money, you know, kind of like a peer-to-peer basis, like, if I'm sending my mom a little bit of money, or she's sending me something, you're kind of within the family. Things that I would think would be kind of very easy and straightforward actually do cause her a little bit more concern. Okay, I'm entering my debit card number into this so that it can get, you know, the cash transferred into my bank account. You know, again, for me, it didn't even cross my mind, actually, that that would be something uncomfortable. But for my mom, that was something where she actually had some concerns about it and was messaging me. Her kind of personal point of view on that was, I would rather use a credit card for this and get the money on a credit card instead of a debit card because the debit card is linked to a bank account, and the security around that needs to be, you know, much tighter. And so, it made her more uncomfortable entering that on her phone. Whereas even a credit card it would have given her a little bit more peace of mind simply because it wasn't directly tied to her bank account. So, that's just, you know, the most recent example. I mean, honestly, that was earlier today, but it's something I hadn't thought of. And, again, for most of our customers, maybe that's not the case and how they think. But for folks that are at that retirement age, you know, in a world where there are constant barrages of scam, you know, emails, and phone calls, and text messages going around, the concern was definitely there. VICTORIA: That happened to me. Last week, I was on vacation with my family, and we needed to pay my mom for the house we'd rented. And I had to teach her how to use Zelle and set up Zelle. [laughter] It was a week-long process. But we got there, and it works [laughs] now. But yeah, it's interesting what concerns they have. And the funny part about it was that my sister-in-law happens to be, like, a lawyer who prevents class action lawsuits at a major bank. And she reassured us that it was, in fact, secure. [laughs] I think it's interesting thinking about that user experience for security. And I'm curious, again, like, compare again with the developer experience and using security toolings. And I wonder if you had any top recommendations on tools that make the developer experience a little more comfortable and feeling like you're deploying with security in mind. RISHI: That, in particular, is a bit of a hard question to answer. I try and stay away from specific vendors when it comes to that because I think a lot of it is contextual. But I could definitely talk through, like, some of the tools that I use and the way I like to think about it, especially from the developer perspective. I think, first off, consider what aspect of the software development, you know, lifecycle you're in. If you are an engineer writing, you know, mostly application code and dealing with building product and features and stuff like that, start from that angle. I could even take a step back and say security as an industry is very, very wide at this point. There is somebody trying to sell you a tool for basically every step in the SDLC process, and honestly, before and after to [inaudible 26:23]. I would even almost say it's, to some extent, kind of information and vendor overload in a lot of ways. So, I think what's important is to think about what your particular aspect of that is. Again, as an application engineer, or if you're building cloud infrastructure, or if you're an SRE, you know, or a platform team, kind of depending on what you are, your tooling will be different. The concepts are all kind of similar ideas, but how you go about what you build will be different. In general, I like to say, from the app side of things, A, start with considering the code you're writing. And that's a little bit cultural, but it's also kind of more training. Are you writing code with a security mindset? are you designing systems with a security mindset? These aren't things that are typically taught, you know, in school if you go get a CS degree, or even in a lot of companies in terms of the things that you should be thinking about. So, A, start from there. And if you don't feel like you think about, you know, is this design secure? Have we done, you know, threat modeling on it? Are we considering all of the error paths or the negative ways people can break the system? Then, start from that and start going through some of the security training that exists out there. And there's a lot of different aspects or avenues by which you can get that to be able to say, like, okay, I know I'm at least thinking about the code I write with a security mindset, even if you haven't actually changed anything about the code you're writing yet. What I actually think is really helpful for a lot of engineers is to have them try and break things. It's why I like to compete in CTFs, but it's also why I like to have my engineers do the same types of things. Trying to break software is both really insightful from the aspect that you don't get when you're just writing code and shipping it because it's not something you have time to do, but it's also a great way to build up some of the skills that you need to then protect against. And there's a lot of good, you know, cyber ranges out there. There's lots of good, just intentionally vulnerable applications that you can find on GitHub but that you can just run, you know, locally even on your machine and say, okay, now I have a little web app stood up. I know this is vulnerable. What do I do? How do I go and break it? Because then all of a sudden, the code that you're writing you start to think about a little bit differently. It's not just about how am I solving this product problem or this development problem? But it's, how am I doing this in a way that is safe and secure? Again, as an application side of things, you know, just make sure you know the OWASP Top 10 inside and out. Those are the most basic things a lot of engineers miss. And it only takes, again, one miss for it to be critical. So, start reviewing it. And then, you start to think about the tooling aspect of it. People are human. We're going to make mistakes. So, how do we use the power of technology to be able to stop this? You know, and there is static scanning tools. Like, there's a whole bunch of different ones out there. You know, Semgrep is a great one that's open source just to get started with that can help you find the vulnerable code that may exist there. Consider the SQL queries that you're writing, and most importantly, how you're writing them. You know, are you taking user input and just chucking it in there, or are you sanitizing it? When I ask these questions, for a lot of engineers, it's not usually yes or no. It's much more of an, well, I don't know. Because in software, we do a really good job of writing abstraction layers. But that also means, you know, to some extent, there may be a little bit of magic in there, or a lack thereof of magic that you don't necessarily know about. And so, you have to be able to dive into the libraries. You have to know what you're doing to even be able to say something like, oh no, this SQL query is safe from this user input because we have sanitized it. We have, you know, done a prepared statement, whatever it may be. Or, no, actually, we are just doing something here that's been vulnerable, and we didn't realize we were, and so now that's something we have to address. So, I think, like, that aspect in and of itself, which isn't, you know, a crazy ton of things. It's not spending a ton of money on different tools. But it's just internalizing the fact that you start to think a little bit differently. It provides a ton of value. The last thing on that, too, is to be able to say, especially if you're coming from a development side, or even just from a founder or a startup side of things, what are my big risks? What do I need to take care of first? What are the giant holes or flaws? You know, and what is my threat model around that? Obviously, as a bank, you have to care very deeply right from the start. You know, if you're not a bank, if you're not dealing with financial transactions, or PII, or anything like that, there are some things that you can deal with a little bit later. So, you have to know your industry, and you have to know what people are trying to do and the threat models and the threat vectors that can exist based on where you are. WILL: That's amazing. You know, earlier, we talked about you being an engineer for 20 years, different areas, and stuff like that. Do you have any advice for engineers that are starting out right now? And, you know, from probably year one to year, you know, anything under ten years of experience, do you have any advice that you usually give engineers when you're chatting with them? RISHI: The advice I tend to give people who are just starting out is be the type of person that asks, "How does this work?" Or "Why does this work?" And then do the work to figure out the answer. Maybe it is talking to someone; maybe it's diving into the details; maybe it's reading a book in some aspect that you haven't had much exposure to. When I look at my career and when I look at the careers of folks around me and the people that I've seen be most successful, both in engineering but also on the business side, that desire to know why something is the case is I think, one of the biggest things that determines success. And then the ability to answer that question by putting in the right types of work, the right types of scientific method and processes and such, are the other factor. So, to me, that's what I try and get across to people. I say that mostly to junior folks because I think when you're getting started, it's really difficult. There's a ton out there. And we've, again, as software engineers, and hardware engineers, and cloud, and all this kind of stuff, done a pretty good job of building a ton of abstraction layers. All of our abstraction layers [inaudible 32:28] to some degree. You know, so as you start, you know, writing a bunch of code, you start finding a bunch of bugs that you don't necessarily know how to solve and that don't make any sense in the avenue that you've been exposed to. But as soon as you get into the next layer, you understand how that works begin to make a lot more sense. So, I think being comfortable with saying, "I have no idea why this is the case, but I'm going to go find out," makes the biggest difference for people just starting out their career. WILL: I love that advice. Not too long ago, my manager encouraged me to write a blog post on something that I thought that I really knew. And when I started writing that blog post, I was like, oh boy, I have no idea. I know how to do it, but I don't know the why behind it. And so, I was very thankful that he encouraged me to write a blog post on it. Because once you start explaining it to other people, I feel you really have to know the whys. And so, I love that advice. That's really good advice. VICTORIA: Me too. And it makes sense with what we see statistically as well in the DORA research. The DevOps Research Association publishes a survey every year, the State of DevOps Report. And one of the biggest findings I remember from last year's was that the most secure and reliable systems have the most open communication and high trust among the teams. And so, being able to have that curiosity as a junior developer, you need to be in an environment where you can feel comfortable asking questions [laughs], and you can approach different people, and you're encouraged to make those connections and write blog posts like Will was saying. RISHI: Absolutely, absolutely. I think you touched on something very important there as well. The psychological safety really makes a big difference. And I think that's critical for, again, like, folks especially earlier in their career or have recently transitioned to tech, or whatever the case may be. Because asking "Why?" should be something that excites people, and there are companies where that's not necessarily the case, right? Where you asking why, it seems to be viewed as a sign that you don't know something, and therefore, you're not as good as what you should be, you know, the level you should be at or for whatever they expect. But I do think that's the wrong attitude. I think the more people ask why, the more people are able and comfortable to be able to say, "I don't know, but I'm going to go find out," and then being able to be successful with that makes way better systems. It makes way safer and more secure systems. And, honestly, I think it makes humans, in general, better humans because we can do that. VICTORIA: I think that's a great note to start to wrap up on. Is there any questions that you have for me or Will? RISHI: Yeah. I would love to hear from both of you as to what you see; with the experiences that you have and what you do, the biggest impediments or speed bumps are when it comes to developers being able to write and ship secure code. VICTORIA: When we're talking with new clients, it depends on where they are in really the adoption of their product and the maturity of their organization. Some early founders really have no technology experience. They have never managed an IT organization. You know, setting up basic employee account access and IDs is some of the initial steps you have to take to really get to where you can do identity management, and permissions management, and all the things that are really table stakes for security. And then others have some progress, and they have a fair amount of data. And maybe it's in that situation, like you said before, where it's really a trade-off between the cost and benefit of making those changes to a more secure, more best practice in the cloud or in their CI/CD pipeline or wherever it may be. And then, when you're a larger organization, and you have to make the trade-offs between all of that, and how it's impacting your developer experience, and how long are those deployed times now. And you might get fewer rates of errors and fewer rates of security vulnerabilities. But if it's taking three hours for your deployments to go out [laughs] because there's so many people, and there's so many checks to go through, then you have to consider where you can make some cuts and where there might be more efficiencies to be gained. So, it's really interesting. Everyone's on a different point in their journey. And starting with the basics, like you said, I love that you brought up the OWASP Top 10. We've been adopting the CIS Controls and just doing a basic internal security audit ourselves to get more ready and to be in a position where... What I'm familiar with as well from working in federal agencies, consulting, maintaining some of the older security frameworks can be a really high cost, not only in terms of auditing fees but what it impacts to your organization to, like, maintain those things [laughs] and the documentation required. And how do you do that in an agile way, in a way that really focuses on addressing the actual purpose of the requirements over needing to check a box? And how do we replicate that for our clients as well? RISHI: That is super helpful. And I think the checkbox aspect that you just discussed I think is key. It's a difficult position to be in when there are boxes that you have to check and don't necessarily actually add value when it comes to security or compliance or, you know, a decrease in risk for the company. And I think that one of the challenges industry-wide has always been that security and compliance in and of itself tends to move a little bit slower from a blue team or a protection perspective than the rest of the industry. And so, I mean, I can think of, you know, audits that I've been in where, you know, just even the fact that things were cloud-hosted just didn't make sense to the auditors. And it was a struggle to get them to understand that, you know, there is shared responsibility, and this kind of stuff exists, and AWS is taking care of some things, and we're taking care of some other things when they've just been developed with this on-premise kind of mentality. That is one of the big challenges that still exists kind of across the board is making sure that the security work that you're doing adds security value, adds business value. It isn't just checking the box for the sake of checking the box, even when that's sometimes necessary. VICTORIA: I am a pro box checker. RISHI: [laughs] VICTORIA: Like, I'll get the box checked. I'll use Trello and Confluence and any other tool besides Excel to do it, too. We'll make it happen with less pain, but I'd rather not do it [laughs] if we don't have to. RISHI: [laughs] VICTORIA: Let's make it easy. No, I love it. Is there anything else that you want to promote? RISHI: No, I don't think there's anything else I want to promote other than I'm going to go back to what I said just earlier, like, that culture. And if, you know, folks are out there and you have junior engineers, you have engineers that are asking "Why?", you have people that just want to do the right thing and get better, lean into that. Double down on those types of folks. Those are the ones that are going to make big differences in what you do as a business, and do what you can to help them out. I think that is something we don't see enough of in the industry still. And I would love for that to change. VICTORIA: I love that. Thank you so much, Rishi, for joining us. RISHI: Thanks for having me. This was a great conversation. I appreciate the time. VICTORIA: You can subscribe to the show and find notes along with a complete transcript for this episode at giantrobots.fm. If you have questions or comments, email us at hosts@giantrobots.fm. And you can find me on Twitter @victori_ousg. WILL: And you could find me on Twitter @will23larry. This podcast is brought to you by thoughtbot and produced and edited by Mandy Moore. Thanks for listening. See you next time. ANNOUNCER: This podcast is brought to you by thoughtbot, your expert strategy, design, development, and product management partner. We bring digital products from idea to success and teach you how because we care. Learn more at thoughtbot.com.Special Guest: Rishi Malik.Sponsored By:thoughtbot: Now that you have funding, it’s time to design, build and ship the most impactful MVP that wows customers now and can scale in the future. thoughtbot Lift Off brings you the most reliable cross-functional team of product experts to mitigate risk and set you up for long-term success. As your trusted, experienced technical partner, we’ll help launch your new product and guide you into a future-forward business that takes advantage of today’s new technologies and agile best practices. Make the right decisions for tomorrow, today. Get in touch at: thoughtbot.com/liftoffSupport Giant Robots Smashing Into Other Giant Robots

Amy Spurling is the Founder and CEO of Compt, helping companies build and scale flexible perks, stipends that delight teams. She explains how Compt's approach to benefits aligns with an employee's life stages, and shares insights from data that revealed the vast diversity of vendors utilized by employees. Amy talks about fundraising for Compt, highlighting the gender investment gap and the difficulties faced by female founders. She also shares her personal experiences as a lesbian founder and emphasizes the importance of a diverse workforce. She outlines Compt's mission to provide equitable compensation and foster a broader perspective within companies, the economic miss of not investing in female-founded companies, and the complexities of transitioning into different roles within a startup. Amy's leadership values of balance and belonging are explored, and she shares insights about navigating hurdles like SOC 2 and GDPR compliance. Additionally, they talk about trends in the tech industry, such as AI's use in healthcare and the potential for bias in software, along with data privacy issues. __ Compt.io Follow Compt.io on LinkedIn, Instagram, Facebook, or Xr. Follow Amy Spurling on LinkedIn or X. Follow thoughtbot on Twitter or LinkedIn. Become a Sponsor of Giant Robots! Transcript: VICTORIA: This is the Giant Robots Smashing Into Other Giant Robots Podcast, where we explore the design, development, and business of great products. I'm your host, Victoria Guido. WILL: And I'm your other host, Will Larry. And with us today is Amy Spurling, Founder and CEO of Compt, helping companies build and scale flexible perks, stipends that delight teams. Amy, thank you for joining. AMY: Thanks so much for having me. VICTORIA: Amy, I saw in your LinkedIn background that you have a picture of someone hiking in what looks like a very remote area. So, just to start us off today, I wonder if you could tell us a little bit more about that. And what's your hobby there? AMY: Sure. I do spend a lot of time backpacking. That picture, I believe, was actually taken in Mongolia a couple of years ago. We spent ten days kind of hiking around in, I mean, everything is backcountry basically in Mongolia. So, spending a lot of time walking around, looking at mountains, is kind of my pastime. WILL: I have a question around backpacking itself. When you say backpacking, what does that mean? Does it mean you only have a backpack, and you're out in the mountains, and you're just enjoying life? AMY: It depends. So, in Mongolia, there were a couple of folks with camels, so carrying the heavy gear for us but still living in tents. My wife and I just did a backpacking trip in the Accursed Mountains in Albania, though, and everything was on our backpack. So, you're carrying a 35-pound pack. It has all your food, your water, your camping gear, and you just go. And you're just kind of living off the land kind of. I mean, you're taking food, so it's not like I'm foraging or hunting but living in the outback. WILL: Wow. What does that do for you just internally, just getting off the grid, enjoying nature? Because I know with tech and everything now, it's kind of hard to do that. But you've done that, I think you said, for ten days. Like, walk us through that experience a little bit. AMY: Some people use yoga, things like that, to go to a zen place, be calm, you know, help quiet their mind. For me, I need to do something active, and that's what I use this for. So getting off away from my phone, away from my laptop—those are not available to me when I'm in the mountains—and just focusing on being very present and listening to the birds, smelling the flowers. You know, pushing myself to where I'm, you know, exerting a lot of energy hiking and just kind of being is just...it's pretty fantastic. VICTORIA: And I'm curious, what brought you to decide to go to Albania to get to that experience? Because that's not a top destination for many people. But -- AMY: It is not. So, we travel a fair amount, and we backpack a fair amount. And the mountains there are honestly some of the most beautiful I've seen anywhere in the world. And so, we're always looking for, where can you get off the grid pretty quickly? Where can you be in the mountains pretty quickly in a way that still has a path so that you're not putting yourself in danger? Unless...I mean, we've done that too. But you want to make sure you have a guide, obviously, if you're going completely no path, no trail kind of camping, too. But it just looked really beautiful. We planned it actually for three years ago and had to cancel because it was May of 2020. And so, we've had this trip kind of on the books and planned for it for a while. VICTORIA: That's awesome. Yeah, I know of Albania because I had a friend who worked there for a few years. And she said the rock climbing there is amazing. And it actually has one of the last wild rivers in Europe. So, it's just a very remote, very interesting place. So, it's funny that you went there [laughs]. I was like, wait, other people also go to Albania. That's awesome. I love the outdoor space. Well, what a great perk or benefit to working to be able to take those vacations and take that time off and spend it in a way that makes you feel refreshed. Tell me more about Compt and your background. What led you to found this company? AMY: Sure. I've been in tech companies for, you know, over 20 years. I've been a CFO, a COO building other people's dreams, so coming in as a primary executive, you know, first funding round type of person, help scale the team, manage finance and HR. And I loved doing that, but I got really frustrated with the lack of tools that I needed to be able to hire people and to retain people. Because the way we compensate people has changed for the last 10, 15 years. And so, ultimately, decided to build a platform to solve my own problem and my own team's problems, and started that getting close to six years ago now. But wanted to build a tech company in a very different way as well. So, in the same way, I take time off, I want my team to take time off. So, we operate on a basis of everyone should be taking their time off. Don't check in while you're out. We'll make sure we're covered. You know, let's build a sustainable business here. And everybody should be working 40 to 45 hours a week, which is definitely not a startup culture or norm. WILL: Yeah. I love that. I was doing some research on Compt. And so, in your words, can you explain to everyone exactly what your company does? AMY: Sure. So, we build lifestyle benefit accounts for companies. And what that means...and the terminology keeps changing, so some people may call them stipends or allowances. But it's really looking at how you pull together employee perks, benefits that will help compete for talent. And right now, retention is kind of the key driver for most companies. How do I keep the people I have really happy? Competitive salaries are obviously table stakes. Health insurance for most industries is table stakes. So, it's, what else are you offering them? You can offer a grab bag of stuff, which a lot of companies try and do, but you get very low utilization. Or you can do something like a stipend or a lifestyle spending account, which is what we build, which allows for complete flexibility so that every employee can do something different. So that even if you're offering wellness, you know, what the three of us think about as wellness is likely very different. I spend a lot of money at REI, like, they are basically, like, as big as my mortgage. I spend so much money there because I want backpacking gear. Wellness for you folks may be a little bit different. And so, allowing for that personalization so everybody can do something that matters to them. VICTORIA: Right. And I love that it comes from a problem you found in your own experience of working with early-stage startups and being on the executive level and finance and building teams from the ground up. So, I'm curious, what lessons did you find in your previous roles that were maybe ten times more important when you started your own company? AMY: I learned so much through all of my prior companies and pulled in the lessons of the things that worked really well but then also the things that it was, like, wow, I would definitely do that different. DEI is very important to us. I knew building a diverse team was going to be a competitive advantage for us. And none of my prior teams really met that mark. You know, most of them were Boston-based, the usual kind of profile of a tech company: 85%-95% White guys, mostly from MIT, you know, very, very talented, but also coached and trained by the same professors for the last 20 years. So, I knew I wanted different perspectives around the table, and that was going to be really key. So, looking at non-traditional backgrounds, especially as we were looking at hiring engineers, for instance, that was really interesting to me because I knew that would be part of our competitive advantage as we started building up this platform that is employee engagement but very much a tax compliance and budgeting tool as well. VICTORIA: I love hearing that. And it's something I've heard from actually thoughtbot's founder, Chad. That is something he wished he invested more in when he first started it. So, I'm curious as to how that's played out from when you started to where you are now. You said, I think, it's been six years, right? AMY: January will be six years, so five and a half-ish, I guess, right now. I mean, it was a stated part of what we were going to do from day one. All of my prior companies wanted that as well. I don't think anybody starts out and says, "Hey, I'd really love a one-note company." No one says that. Everybody thinks that they're doing the right things and hiring the best talent. But what you do is you end up hiring from your network, which usually looks just like you. And when you get to be, you know, 100, 150 people and you're looking around going, wow, we have some gaps here, it's really hard to fill them because who wants to be the first and the only of whatever? You know, I've been the only woman on most management teams. So, for us, it was day one, make it part of the focus and make sure we're really looking for the best talent and casting a very wide net. So, right now, we're sitting at 56% female and 36% people of color, and somewhere around 18%-19% LGBTQIA. So, we're trying to make sure that we're attracting all those amazing perspectives. And they're from people from around the country, which I also think is really important when you're building a tech company. Don't just build in areas where you're in your little tech bubble. If you want to build a product that actually services everyone, you need to have other kind of cultural and country perspectives as well. VICTORIA: Yeah. And that makes perfect sense for what you described earlier for Compt, that it is supposed to be flexible to provide health benefits or wellness benefits to anyone. And there can be a lot of different definitions of that. So, it makes sense that your team reflects the people that you're building for. AMY: Exactly. WILL: Yeah. How does that work? How does Compt accomplish that? Because I know early on I was doing nonprofits and I was a decent leader. But I struggle to get outside of myself, my own bubble if that makes sense. So, like, that was before I had kids. I had no idea what it meant to have kids and just the struggles and everything if you have kids. So, there's so many different things that I've learned over the years that, like, just people have their own struggles. So, how does Compt accomplish the diversity of a company? AMY: So, it's so interesting you mentioned that. I was on a podcast the other day with somebody who was, like, "You know, we didn't really think about our benefits and how important they were." And then, the founder who was the person on the podcast, and he was like, "But then I had kids. And suddenly, I realized, and we had this amazing aha moment." I'm like, well, it's great you had the aha moment. But let's back it up and do this before the founder has children. Sometimes you need to recognize the entire team needs something different and try and support them. My frustration with the tools out there are there are tools that are like, hey, we're a DE&I platform. We will help you with that. You know, we've got a benefit for fertility. We've got a benefit for, you know, elder care. There's all kinds of benefits. These are great benefits, but they're also very, very specific in how they support an employee. And it's very small moment in time, usually. Whereas with something like Compt, where we say, "Hey, we support family," your version of family, having children is very different from my version of family, where I don't have children, but we both have families. And we can both use that stipend in a way that is meaningful for us. What puts the employee back in charge, what matters in their lives, instead of the company trying to read everyone's mind, which is honestly a no-win situation for anyone. So, it just makes it very, very broad. VICTORIA: Yes. And I've been on both sides, obviously, as an employee, but also previously role of VP of Operations. And trying to design benefits packages that are appealing, and competitive, and fair is a challenging task. So -- AMY: It's impossible. It's impossible. [laughs] VICTORIA: Very hard. And I'm curious what you found in the early stages of Compt that was surprising to you in the discovery process building the product. AMY: So, for me, I mean, discovery was I am the buyer for this product. So, I wanted this about five years before I decided to go and build it. And I was talking to other finance and HR professionals going around going, "All right, are you feeling this exact same pain that I'm feeling? Because it is getting completely insurmountable." We were all being pitched all these different platforms and products. Everybody had something they wanted to sell through HR to help attract, and engage and retain talent and all the things, right? But there's no tracking. It's not taxed correctly. And ultimately, no matter what you bring in, maybe 2% to 3% of your team would use it. So, you're spending all this time and energy in putting all this love into wanting to support your team, and then nobody uses the stuff that you bring in because it just doesn't apply to them. And so, I realized, like, my pivotal moment was, all right, none of this is working. I've been waiting five years for somebody to build it. Let's go build something that is completely vendor-agnostic. There's no vendors on this platform by design because everyone ultimately wants something different. And, you know, through that process, we were, of course, pushed by many VCs who said, "Hey, build your marketplace, build your marketplace, you know, that's going to be your moat and your special sauce." And I said, "No, no, no, that's not what we're going to do here because that doesn't solve that problem." And we finally had the data to prove it, which is fantastic. You know, we actually did a sample of 8,700 people on our platform, and we watched them for a year. And said, "How many different vendors are these 8,700 people going to use?" Because that's the marketplace we'd have to build because we have 91% employee engagement. Nobody can beat us in the industry. We've got the highest employee engagement of any platform in our category. So, how many different vendors could 8,700 people use in that time period? Do you guys have any guesses how many they used in that time period to get to that engagement? VICTORIA: Out of 8,700 vendors? AMY: No, 8,700 employees. So, how many different vendors they used in that time period. VICTORIA: Hmm, like, per employee, I could see maybe, like, 10? I don't know. Two? AMY: We saw 27,000 different vendors used across all the employees, so 27,000 different unique vendors. So, on average, every employee wants three unique vendors that no one else is using. VICTORIA: Oh wow. WILL: Wow. VICTORIA: Yeah, okay. [laughter] Right. AMY: So, it's just you can't build that, I mean, you could build that marketplace, but nobody's going to visit that marketplace because nobody wants to scroll through 27,000 things. And so, it just keeps changing. You know, and I saw that even with the woman who started the company with me, you know, when she...we, of course, use Compt internally. And she started using her wellness stipend. You know, at first, she was doing 5Ks. So, she'd register for the race. She'd go train. She'd do all the things. Then she got pregnant and had a baby and started shifting over to prenatal vitamins, to Lamaze classes, to, you know, mommy yoga, things like that. Then once she had the baby, it shifted again. And so, it allows for a company to flow with an employee's lifecycle without having to get into an employee's life stage and, "Hey, what do you need at this moment in time?" Employees can self-direct that, so it makes it easier for employees and a lot easier for companies who are not trying to...we don't want to map out every single moment of our employee's personal life. We shouldn't be involved in that. And so, this is a way to support them but also give them a little space too. WILL: I absolutely love that because that is, yes, that is a flow. Like, before you have kids, it's, like, yes, I can go run these 5Ks; I can do this. When you have kids, it totally changes. Like, okay, what can I do with my kids? So, workout, or that's my away time. So, I love that it's an ebb and flow with the person. And they can pick their own thing, like -- AMY: Right. We're all adults. WILL: Yes. [laughs] AMY: I think I sat there going; why am I dictating someone's health and wellness regimen? I am not qualified for this on any stretch. Like, why am I dictating what somebody's mental health strategy should be? That's terrifying. You're adults. You work with your professionals. We'll support it. WILL: Yes. I remember at one company I worked for; they had this gym that they had, you know, got a deal with. And I was so frustrated because I was like, that's, like, 45 minutes away from my house. AMY: [laughs] Right. WILL: It's a perk, but it means absolutely nothing to me. I can't use it. So yes, yeah. [laughs] AMY: Well, and, like, not everybody wants to work, say...there was, you know, we see a lot of that is there's been a transition over time. COVID really changed that as people couldn't go to gyms, and companies shifted to stipends. But you may not want to work out with your co-workers, and that's okay, too. Like, it's okay to want to do your own thing and be in your own space, which is where we see this kind of decline of the, you know, on-site company gym, which, you know, some people just don't want to do that. VICTORIA: Yeah. So, I love that you stayed true to this problem that you found and you backed it up with data. So, you're like, here's clear data on, say, why those VCs' advice was bad [laughs] about the marketplace. AMY: Ill-informed. They needed data to see otherwise. [laughs] VICTORIA: Yeah. Well, I'm curious about your experience going through fundraising and starting up for Compt with your background as a CFO and how that was for you. AMY: It was...I naively thought it would be easier for me, and maybe it was because I had all this experience raising money as a CFO in all these prior companies. But the reality is that women receive less than 2% of all funding, even though we start 50% of the businesses. And if you look at, you know, Black female founders, they're receiving, like, 0.3, 0.5% of funding. Like, it's just...it's not nice out there. You know, on average, a lot of VCs are looking at 3,000, 4,000, or 5000 different companies a year and investing in 10. And so, the odds of getting funded are very, very low, which means that you're just going to experience a whole lot of unique situations as a female founder. I saw that you folks work with LOLA, which is fantastic. I'm a huge fan of LOLA and kind of what their founders put together. And I've heard some amazing things about the pitches that she's done for VCs and that she's just not shy about what she's building. And I really appreciate that. It's never a fun situation. And it gets easier the later stages because you have more metrics, and data, and all of that. And we ultimately found phenomenal investors that I'm very, very happy to have as part of our journey. But it's definitely...it's not pretty out there is the reality. VICTORIA: Right. And I saw that you either attended or put on an event about the gender investment gap, which I think is what you just referred to there as well. So, I'm curious how that conversation went and if there were any insights about what the industry can do to promote more investment in women and people of color founders. AMY: So, that's actually coming up August 10th, and so that's coming up in a few weeks that we're going to be hosting that. I'm actually part of a small group that is spearheading some legislation in Massachusetts to help change this funding dynamic for female founders, which I'm pretty excited about. And California also has some legislation they're looking at right now. In Mass, we're looking at how fair lending laws can apply to venture capital. There are laws on the books on how capital gets distributed when you look at the banking system. But there's virtually no regulation when you look at venture funding, and there's no accountability, and there's no metrics that anybody is being held to. I don't believe that you know, just because I pitched a VC that they should be funding me, you know, it needs to be part of their thesis and all of those things. But when you see so much disparity in what is happening out there, bias is coming into play. And there needs to be something that helps level that playing field. And so, that's where legislation comes into play and helps change that dynamic. So, pretty excited about the legislation that's before both the Senate and the Mass State House, likely going to be heard this November. So, we're pretty excited about that. Mid-Roll Ad: As life moves online, bricks-and-mortar businesses are having to adapt to survive. With over 18 years of experience building reliable web products and services, thoughtbot is the technology partner you can trust. We provide the technical expertise to enable your business to adapt and thrive in a changing environment. We start by understanding what’s important to your customers to help you transition to intuitive digital services your customers will trust. We take the time to understand what makes your business great and work fast yet thoroughly to build, test, and validate ideas, helping you discover new customers. Take your business online with design‑driven digital acceleration. Find out more at tbot.io/acceleration or click the link in the show notes for this episode. WILL: So, Amy, you're talking a lot about diversity, inclusion, and just biases, and things like that. You're doing a great job with it. Your product is perfect for that because it reaches so many different levels. And I just want to ask you, why are you so passionate about it? Why is this so important to you? AMY: For me, personally, I am a lesbian founder. I am the only, you know, LGBTQ in many of my companies. And I'm always the, I mean, very frequently, the only woman in the boardroom, the only woman on the leadership team. That's not super comfortable, honestly. When you are having to fight for your place at the table, and you see things that could be done differently because you're bringing a different perspective, that, to me, is a missed opportunity for companies and for employees as well who, you know, there's amazing talent out there. If you're only looking at one flavor of talent, you're missing the opportunity to really build a world-class organization. And so, to me, it's both the personal side where I want to work with the best people. I want to work with a lot of different perspectives. I want to work with people who are bringing things to the table that I haven't thought about. But also, making sure that we're creating an environment where those people can feel comfortable as well, and so people don't feel marginalized or tokenized and have the ability to really bring their best selves to work. That's really important to me. It's a reflection of the world around us. It's bringing out the best in all of us. And so, for me, that's the environment I want to create in my own company. And it's also what I want to help companies be able to foster within their companies because I think a lot of companies really do want that. They just don't know how to go about it. They don't have actual tools to support a diverse team. You pay for things for the people you have, and then you hire more people like the people you have. We want to be a tool to help them expand that very organically and make it a lot easier to support a broader perspective of people. VICTORIA: I appreciate that. And it speaks to something you said earlier about 50% of the businesses are started by women. And so, if you're not investing in them, there's a huge market and huge potential and opportunity there that's just not -- AMY: The economic miss is in the trillions, is what's been estimated. Like, it's an absolute economic miss. I mean, you also have the statistics of what female-founded companies do. We tend to be more profitable. We tend to be more capital efficient. We tend to, you know, have better outcomes. It's just so the economics of it are there. It's just trying to get folks to understand where their biases are coming into play and funding things that may be a little outside their comfort zone. VICTORIA: Right. That's going to be a big project to undo all of that. So, each piece that works towards it to break it down, I think, is really important. And it seems like Compt is a great tool for companies to start working towards that, at least in the equity of their benefits, which is -- [laughs] AMY: Exactly. Because, I mean, if people can't use a perk, then it's inequitable compensation. And if you have inequitable compensation, you're already going down that path. You end up with wage gaps, and then you end up with promotion gaps. And all these things feed into each other. So, we're just trying to chip away at one piece of the problem. There's lots of places that this needs to be adjusted and changed over time. But we want to at least chip away at that one piece where this piece of compensation can be equitable and support everyone. WILL: Yeah, I love that. I was looking at your LinkedIn. And it looks like you've been almost, later this year, maybe six years of Compt. What was some of the early traction? Like, how was it in the early days for you? AMY: It was an interesting transition for me, going from CFO and COO over to the CEO role. That was easier in some ways than I thought it was going to be and harder in other ways. You know, on the easy side, I've already done fundraising. I understand how to write a business model, and look at financial plans, and make sure the concept is viable and all the things. But I also am not an engineer. I'm not a product designer. And so needed to make sure we immediately surrounded ourselves with the right talent and the right help to make sure that we could build the right product, pull the things out of my brain that are conceptual but definitely not product design. No one wants me touching product design. I've been barred from all codebases in this company. They don't want me touching anything, with good reason. And so, making sure that we have those right people to build and design the software in a way that functionally makes sense. VICTORIA: I think that is great that...I laughed when you said that you are barred from touching any of the code. [laughs] It's like, you're able to...I think a strong leader recognizes when other people have the expertise and makes space for them to do their best work. I also see that, at the same time, you've been a mentor with the MassChallenge group. And I'm curious if you have a most frequent piece of advice that you give to founders and people starting out building great products. AMY: The biggest piece of advice, I think, is to make sure you're taking care of yourself through this process. It's an exhausting process to build a company. And there's always way more that you should be doing every day than you can possibly get done. And if you just completely absorb yourself in it, you're going to end up burning out. So, making sure that you rest, that you still make time to exercise and to move, and that you spend time with family. All of those things, I think, are really, really important. That's been part of our core tenets. From day one, I said, "No more than 40 to 45 hours a week." It doesn't mean I'm not thinking about this business far more than 45 hours a week, but I'm not going to sit behind a computer that many hours in a week because I will burn out. And if I'm out and I'm reading something, or I'm, you know, going for a walk, I'm going to have moments of inspiration because I can actually have those creative thoughts firing when I'm not just putting out fires. And so, I think that's really, really important for founders to make sure they take that time and allow their brains to clear a little bit so that they can build more efficiently, build faster, and have really good critical reasoning skills. WILL: I love that you not only have the product to, you know, help taking time off, but you also are preaching it per se, like, take time off. Don't work more than 40-45 hours. Like, take care of yourself. So, I love that advice that you're giving is right in the message with your product. So, I love it. AMY: Thank you. I do hammer home with this team. What we build is obviously very, very important to me, but how we build this company is equally important. We spend just as much time thinking about how we're building and designing this company internally as we do about our product because they need to be a virtuous cycle between the two, quite frankly. And so, if they aren't aligned, we're going to fail. WILL: Definitely. Wow. Awesome. What does success look like for you and Compt in the next, you know, six months to a year? AMY: For us, it's really about reaching as many people as possible. So, how do we have an impact on as many lives as possible and help people be able to access this piece of their compensation? What is interesting right now is we're in a really interesting moment. The tech industry is going through...shall we call it an awakening? Where money is tighter. There's been some layoffs. You know, it's just a very different world in tech right now. And everybody's in a little bit of a holding pattern to figure out, okay, what's next? What we're seeing across our portfolio of companies is that there's a lot of industries that are, for the first time, really thinking about how do we retain folks? How do we think about hiring in a new way? So, industries like construction and manufacturing. Industries that never had employee kind of lifestyle benefits or perks they're taking a look at that because unemployment is so, so low. And so, for the first time ever, we have the ability to have an impact on groups that never had access to professional development, to wellness, to things like that. And that's really exciting because you can have such a huge, impactful moment where people have just been without for so long. And so, that's pretty exciting for us. VICTORIA: You're touching upon a topic that I've thought about before, where in the tech industry, we're used to having a lot of benefits and perks and that not every industry is the same way. So, I'm curious; you mentioned construction and some other groups that are looking to adopt more of these benefits because unemployment is so low. I'm curious, like, if there are any patterns or things that you see, like, specific industries that are more interested than others, or what's going on there? AMY: Our portfolio of tech companies are only about...they're less than 40% of our customers, actually. So, a relatively low percentage of our customers come from the tech industry. What we find is that healthcare systems this is really important. As you're thinking about how you're going to retain nursing staff, it is incredibly difficult. And so, we see a lot of movement in the healthcare space. We see a lot of movement, again, across manufacturing and construction, you know, financial services. Pretty much anybody who is struggling to hire and is worried about retaining is trying to figure out what's my strategy? How do I do this in the least expensive way possible but reach everyone? Because those employee engagement metrics are so consistently important to look at. And most platforms and things that you could be doing out there are going to give you a 2% to 3% utilization. So, it's very, very low. You know, wellness is by far the most common use case we see companies putting in place. It's good for employees. It's good for the employer. That's by far the most important or the most common. But we also see things like family, and just more of a whole well-being kind of concept as well, so beyond wellness, so allowing for that broader reach. We're also seeing industries where people are starting to age out. So, we've got five generations at work right now. There's industries where folks have historically stayed forever. You know, you've got the people who have been there 20-30 years. Well, those same industries are now sitting there going, all right, how do I get the next two generations to come in here? Because it's such an old-guard and old approach. We've got to change things up. And so, we're seeing a pretty big cultural shift happen within a lot of these more nascent industries. WILL: Yeah. I can definitely see how that would be tough going from, you know, you said five generations are currently in the workforce? AMY: Yep. WILL: I didn't even think about that. Wow. AMY: Yeah, you got a lot of different parts of the life cycle. You know, think about professional development. Professional development for a 22-year-old is very different from professional development for a 65-year-old. But both are in the workplace, and both want to keep learning. It's just what your needs are and what you need to learn. And how you want to learn is going to be very, very different. WILL: Wow. So true. I love how you're talking about your leadership and just the way you lead. I can just hear it in what you're saying. What are some of your core values that drive you every day? AMY: One of the big ones, and it probably goes back to, you know, I'm sure, birth placement, whatever. I'm an oldest child, all the things that come with being an oldest child. But fairness is a really big one for me. And so, it's thinking about how we apply that as a company, so equitable compensation falls under that. Making sure that we've got a team that is balanced and diverse is really important to me. You know, thinking, you know, our core values are balance and belonging. That runs through absolutely everything that we do and is core and central to it. Because, again, how we build this company is just as important to me as what we're building. And so, making sure that we hold true to those values is critical because we have amazing people, and they need to feel supported as well. VICTORIA: Well, that really comes through in everything that you say and that we've talked about so far today, and I really appreciate that. And I'm curious if you could go back in time to when you first started Compt and tell yourself any piece of advice or information; what would you say? AMY: That piece of advice has changed over time; I will tell you that. The one that is most recent for me is really because we're an HR tech platform, and we service, you know, an entire organization, is really thinking about how you support different industries at different moments in time, the concept of product-market fit. When you're that type of a platform, which there aren't many, there's not many platforms that sit across an entire organization, but compensation is one of them. You need to be thinking about which industries are struggling to hire, which are struggling to retain at this moment in time. And so, I don't think there's one place, like, hey, we have product-market fit, now we can scale. I think that's a misnomer for our part of the HR tech space. And so, it's constant experimentation on go-to-market strategy and constant kind of adjustment as markets ebb and flow over time. WILL: What is some of your biggest hurdles right now or even in the future that you can see coming? AMY: If I had a crystal ball, life would definitely be easier. I'd love to know when this economic cycle is going to shift and, you know when things get a little bit easier for companies. You know, HR leaders and finance leaders are not having the most fun at this moment in time. They're being tasked with making everybody happy but on very small budgets, and so they're really challenged with that. And they're really burnt out, and they're exhausted. So, I'm looking forward to a shift so when people can get back to feeling a little bit physically better. But also, it just helps navigate a market and be better able to support your employees. VICTORIA: I've been thinking about that question recently, what I would tell my past self, and I think it's mostly, like, food related. [laughter] AMY: Ooh, interesting. VICTORIA: Use better vinegars, like, invest in fancier olive oil. [laughs] AMY: So, my new luxury pro-tip is you buy a $7 bunch of eucalyptus at the grocery store, and you tie it above your shower head. I'm not kidding; you will feel like you're at a spa. It costs $7. I learned it because I was at some fancy resort. One of my investors, you know, paid for us to go to a conference that I was not paying for. And I was like, that is genius. You suddenly feel like you are in someplace fancy, and it was seven bucks. It's amazing. WILL: Yes. VICTORIA: That sounds incredible. I'm going to do that. WILL: Same. [laughter] VICTORIA: [inaudible 34:35] buy some. No, it's so good. Do you have any questions for us, Amy? AMY: Yeah. I mean, what trends are you seeing in the market right now? Like, what types of companies are being developed? Where do you see growth happening in the market? VICTORIA: That's probably a better question for me. As a managing director, I spend more time networking and going to events. And it's interesting being in San Diego. There's a big biotech startup here. So, I went to an EvoNexus Demo Day and saw the things that people were using. And there seemed to be a trend of using AI and machine learning to create better health outcomes, whether that's for predictors for which people will respond better to anti-cancer drugs, or, you know, how do we monitor the release of drugs for someone's system who's, you know, going through methadone in therapy. So, it's really interesting. I think that you know, you mentioned that there's not the same amount of money in the tech market, but I think there is still a lot of work being done to solve real problems that people have. So yeah, I'm really curious to see those types of projects and which ones are going to be successful, and how much the AI trend will really fade out. Like, clearly, in some use cases, you can see how beneficial it could be. And other times, it seems like it's kind of just like slapped on there for -- AMY: Agreed. VICTORIA: Marketing purposes, so... AMY: That's really just a database query. It's not AI. [laughs] VICTORIA: Right. [laughs] It's interesting because, you know, I just had lunch with a bunch of other CTOs in San Diego, and we were talking about AI, and some of the inherent risks of it, and the damage it can cause. And I always like to bring it back to, like, there are some people who are already harmed by these trends. And we have to work around that. Like, there is some, you know, greater supposed existential threat with AI that I think is rather unlikely. But if we think about that too much and not focus on the current harm that's being done, then that's, you know, more dangerous than the other one. AMY: Yeah. No, absolutely. I mean, there's definitely, I mean, even just with facial recognition and how that's applied and what that's used for. I mean, any software that is built with people has bias. And so, whatever biases they're bringing into it is the bias that's going to exist in the software. And so, there's...we already are starting from, you know, going back to our earlier conversation, if companies are not diverse and not building for really diverse perspectives, they're inherently going to build bias software, whether or not, I mean, I don't think that's anybody's intention. But that's what's going to happen because you just didn't think about things you didn't know. VICTORIA: Right. And, of course, I'm here in Southern California. There's the strikes for the actors and writers' strike happening a few hours north of us. And they were actually, you know, for some actors, signing away their rights to their likeness. AMY: Wow. VICTORIA: And then they could make an AI image and -- AMY: Wow. You could just create an entire movie with somebody's image and dub in a voice, and suddenly you don't need actors. VICTORIA: Right. And it's, of course, more often non-White actors and models who are being replaced. And so, I think that's a very interesting trend that people may not have thought about yet. AMY: Fascinating. VICTORIA: So yeah, I mean, having people on your leadership team who are thinking about these [laughs] different types of issues, like, yeah, I think it's really important. And then also, from, like, a data privacy perspective, all the laws that are coming out and that have come out. And I think that some founders and CTOs are really struggling with how to comply and protect everyone's data that way. AMY: No. It's something we think about a lot because we have the potential to have access to a lot of employee data. We take a very minimalist approach stated, not a big data play. That's not what we're here for. That's not what we're trying to do, this mountain of data on people, and then we'll figure out how to monetize it. We want to build something a little bit different. And so using only data that needs to be used so that we can truly support people with what our actual goal and aim is, rather than having that be a secondary cause. VICTORIA: Yeah. And I wanted to ask you about that actually because you have SOC 2 and GDPR compliance. And it's a topic that I think a lot of founders know that security is important, but it can be a significant investment. So, I'm curious your trade-offs and your timing for when you went for those compliance frameworks. AMY: We went early for it. I mean, so our platform, I mean, we're integrated with payroll platforms. We're touching employee data. So, we went for it early because we knew that it was going to be important, and it's a lot easier to do it before you make a mess than it is after the fact. I've done SOC 2 compliance in two prior companies. It's not fun. It is not my most fun thing that I've ever done. Fortunately, there are geniuses out there who built platforms to make this very, very easy now. We use a platform called Vanta that is absolutely incredible, made it super easy to get SOC 2 compliant, go through our audits, do all the things, so that, at least, is a lot easier. But it was something that we needed the funding to invest in. It's not inexpensive. But we knew that it was going to be critical because people need to feel that their data is secure and that you know what you're doing, and that you're not just kind of flying by the seat of your pants. There's a lot of tech companies that operate on, we'll figure out the tax, or we'll figure out the law. We'll figure out the compliance later. And that's been a stated part of their mission. That's just not the way I'm going to operate. And that doesn't work very well when you're dealing with HR, quite frankly, or finance because we have to comply with laws. So, getting ahead of that early was part of our strategy. VICTORIA: That makes sense. Your finance background making it clear what the legal implications are. [laughs] AMY: Exactly. Like, I'm not messing around with the IRS. Nobody wants to get audited by the IRS. It's not fun. Let's just keep things tax compliant. Chances are you're not going to get audited by the IRS. But if you are a tech company, if you do want to go public, if you do want to be acquired likely from a public company, you have to have these things in order because otherwise, it's coming off your purchase price or your stock price because you've got disclosures you've got to put out there, so little hidden, nasty gotchas. And it can be a six-year lookback period. So, you're like, oh, I'll worry about it later. Six years is a long time. And if you start messing around with that, it gets very, very expensive to clean up. So, just do it right from the beginning. You know, the same way you're doing payroll correctly now, invest a little bit, and it makes it a lot easier. VICTORIA: Yeah, I agree. And I think the tooling that's out there makes it a little bit easier; at least then, you know you have the confidence that your data is protected. Especially if you're a non-technical founder, I can imagine that makes you feel better that things are the way they should be. AMY: Exactly. Somebody has looked at this thing. Somebody is making sure that it's working the way it's supposed to. You know, that definitely helps when you're a non-technical founder, or just not a tax expert, or a legal expert, you know, around these things. It's not even the technical founders that have to worry about it. Data comes in all kinds of forms. VICTORIA: Yeah, that makes a lot of sense. AMY: This has been a fantastic conversation. I've really enjoyed it. VICTORIA: Well, thank you. WILL: Same. VICTORIA: I've enjoyed it as well. I really appreciate you taking the time. You can subscribe to the show and find notes along with a complete transcript for this episode at giantrobots.fm. If you have questions or comments, you can email us at hosts@giantrobots.fm. You can find me on Twitter @victori_ousg. WILL: And you can find me on Twitter @will23larry. This podcast is brought to you by thoughtbot and produced and edited by Mandy Moore. Thanks for listening. See you next time. ANNOUNCER: This podcast is brought to you by thoughtbot, your expert strategy, design, development, and product management partner. We bring digital products from idea to success and teach you how because we care. Learn more at thoughtbot.com.Special Guest: Amy Spurling.Sponsored By:thoughtbot: As life moves online, bricks-and-mortar businesses are having to adapt to survive. With over 18 years of experience building reliable web products and services, thoughtbot is the technology partner you can trust. We provide the technical expertise to enable your business to adapt and thrive in a changing environment. We start by understanding what’s important to your customers to help you transition to intuitive digital services your customers will trust. We take the time to understand what makes your business great and work fast yet thoroughly to build, test, and validate ideas, helping you discover new customers. Take your business online with design‑driven digital acceleration. Find out more at: url tbot.io/acceleration or click the link in the show notes for this episode.Support Giant Robots Smashing Into Other Giant Robots

Sean O'Connor is the Director of Engineering at Datadog. Datadog is the essential monitoring and security platform for cloud applications. Sean discusses his transition from an individual contributor to management and shares why he chose Datadog, emphasizing the appeal of high-scale problems and the real business nature of the company. They delve into the importance of performance management and observability and cover the cultural and technical challenges Sean faces in managing a diverse, geographically spread team, and discuss the transition at Datadog from a decentralized model to more centralized platforms, the corresponding changes in both technical strategies and people management, and what excites him about Datadog's future, including the integration of security offerings into developers' daily experiences, and the evolution of Kubernetes and internal build and release tooling. __ Datadog Follow Datadog on LinkedIn, Instagram, Youtube, or Twitter. Follow Sean O'Connor on LinkedIn or Twitter. Visit his website at seanoc.com. Follow thoughtbot on Twitter or LinkedIn. Become a Sponsor of Giant Robots! Transcript: VICTORIA: This is the Giant Robots Smashing Into Other Giant Robots Podcast, where we explore the design, development, and business of great products. I'm your host, Victoria Guido. WILL: And I'm your other host, Will Larry. And with us today is Sean O'Connor. He is the Director of Engineering at Datadog. Datadog is the essential monitoring and security platform for cloud applications. Sean, thank you for joining us. SEAN: Hi, thanks for having me on. VICTORIA: Yeah, I'm super excited to get to talking with you about everything cloud, and DevOps, and engineering. But why don't we first start with just a conversation about what's going on in your life? Is there any exciting personal moment coming up for you soon? SEAN: Yeah, my wife and I are expecting our first kiddo in the next few weeks, so getting us prepared for that as we can and trying to get as much sleep as we can. [laughs] WILL: Get as much sleep as you can now, so...[laughs] I have a question around that. When you first found out that you're going to be a dad, what was your feeling? Because I remember the feeling that I had; it was a mixed reaction of just everything. So, I just wanted to see what was your reaction whenever you found out that you're going to be a dad for the first time. SEAN: Yeah, I was pretty excited. My wife and I had been kind of trying for this for a little while. We're both kind of at the older end for new parents in our late 30s. So, yeah, excited but definitely, I don't know, maybe a certain amount of, I don't know about fear but, you know, maybe just concerned with change and how different life will be, but mostly excitement and happiness. [laughs] WILL: Yeah, I remember the excitement and happiness. But I also remember, like, wait, I don't know exactly what to do in this situation. And what about the situations that I have no idea about and things like that? So, I will tell you, kids are resilient. You're going to do great as a dad. [laughter] SEAN: Yep. Yeah, definitely; I think I feel much more comfortable about the idea of being a parent now than I may have been in my 20s. But yeah, definitely, the idea of being responsible for and raising a whole other human is intimidating. [laughs] VICTORIA: I think the fact that you're worried about it is a good sign [laughs], right? SEAN: I hope so. [laughs] VICTORIA: Like, you understand that it's difficult. You're going to be a great parent just by the fact that you understand it's difficult and there's a lot of work ahead. So, I think I'm really excited for you. And I'm glad we get to talk to you at this point because probably when the episode comes out, you'll be able to listen to it with your new baby in hand. So... WILL: Good. Excited for it. [laughs] VICTORIA: Yeah, love that. Well, great. Well, why don't you tell me a little bit more about your other background, your professional background? What brought you to the role you're into today? SEAN: Yeah. Well, like we mentioned in the beginning; currently, I'm a Director of Engineering at Datadog. I run our computing cloud team. It's responsible for all of our Kubernetes infrastructure, as well as kind of all the tooling for dealing with the cloud providers that we run on and as well as kind of [inaudible 02:54] crypto infrastructure. Within Datadog, I've always been in management roles though I've kind of bounced around. I've been here for about five and a half years. So, before this, I was running a data store infrastructure team. Before that, when I first came in, I was running the APM product team, kind of bounced around between product and infra. And that's kind of, I guess, been a lot of the story of much of my career is wearing lots of different hats and kind of bouncing around between kind of infrastructure-focused roles and product-focused roles. So, before this, I was running the back-end engineering and DevOps teams at Bitly. So, I was there for about five and a half years, started there originally as a software engineer. And before that, a lot of early-stage startups and consulting doing whatever needed doing, and getting to learn about lots of different kind of industries and domains, which is always fun. [laughs] VICTORIA: That's great. So, you had that broad range of experience coming from all different areas of operations in my mind, which is, like, security and infrastructure, and now working your way into a management position. What was the challenge for you in making that switch from being such a strong individual contributor into an effective manager? SEAN: Sure. You know, I think certainly there is a lot of kind of the classic challenges of learning to let go but still staying involved, right? You know, as a manager, if you're working on critical path tasks hands-on yourself, that's probably not a good sign. [laughs] On the other hand, if you come, like, completely divorced from what your team is doing, especially as, like, a team lead level kind of manager, you know, that's not great either. So, figuring that balancing act definitely was a bit tricky for me. Similarly, I think time management and learning to accept that, especially as you get into, like, further steps along in your career that, like, you know, it's not even a question of keeping all the balls in the air, but more figuring out, like, what balls are made out of rubber and which ones are made out of glass, and maybe keeping those ones in the air. [laughs] So, just a lot of those kind of, like, you know, prioritization and figuring out, like, what the right level of involvement and context is, is definitely the eternal learning, I think, for me. [laughs] WILL: I remember whenever I was looking to change jobs, kind of my mindset was I wanted to work at thoughtbot more because of the values. And I wanted to learn and challenge myself and things like that. And it was so much more, but those were some of the main items that I wanted to experience in my next job. So, when you changed, and you went from Bitly to Datadog, what was that thing that made you say, I want to join Datadog? SEAN: Yeah, that was definitely an interesting job search and transition. So, at that point in time, I was living in New York. I was looking to stay in New York. So, I was kind of talking to a bunch of different companies. Both from personal experience and from talking to some friends, I wasn't super interested in looking at, like, working at mostly, like, the super big, you know, Google, Amazon, Meta type of companies. But also, having done, like, super early stage, you know, like, seed, series A type of companies, having played that game, I wasn't in a place in my life to do that either. [laughs] So, I was looking kind of in between that space. So, this would have been in 2018. So, I was talking to a lot of, like, series A and series B-type companies. And most of them were, like, real businesses. [laughs] Like, they may not be profitable yet, but, like, they had a very clear idea of how they would get there and, like, what that would look like. And so, that was pleasant compared to some past points in my career. But a lot of them, you know, I was effectively doing, like, automation of human processes, which is important. It has value. But it means that, like, realistically, this company will never have more than 50 servers. And when I worked at Bitly, I did have a taste for kind of working in those high-scale, high-availability type environments. So, Datadog initially was appealing because it kind of checked all those boxes of, you know, very high-scale problems, high availability needs, a very real business. [laughs] This is before Datadog had gone public. And then, as I started to talk to them and got to know them, I also really liked a lot of kind of the culture and all the people I interacted with. So, it became a very clear choice very quickly as that process moved along. VICTORIA: Yeah, a very real business. Datadog is one of the Gartner's Magic leaders for APM and observability in the industry. And I understand you're also one of the larger SaaS solutions running Kubernetes, right? SEAN: Yep. Yeah, at this point. Five years ago, that story was maybe a little bit different. [laughs] But yeah, no, no, we definitely have a pretty substantial Kubernetes suite that we run everything on top of. And we get the blessings and curses of we get some really cool problems to work on, but there's also a lot of problems that we come across that when we talk to kind of peers in the industry about kind of how they're trying to solve them, they don't have answers yet either. [laughs] So, we get to kind of figure out a lot of that kind of early discovery games. [laughs] VICTORIA: Yeah. I like how exciting and growing this industry is around kind of your compute and monitoring the performance of your applications. I wonder if you could kind of speak to our audience a little bit, who may not have a big technical background, about just why it's important to think about performance management and observability early on in your application. SEAN: There can be a few pieces there. One of the bigger ones, I think, is thinking about that kind of early and getting used to working with that kind of tooling early in a project or a product. I think it has an analogous effect to, like, thinking about, like, compounding interest in, like, a savings account or investing or something like that. In that, by having those tools available early on and having that visibility available early on, you can really both initially get a lot of value and just kind of understanding kind of what's happening with your system and very quickly troubleshoot problems and make sure things are running efficiently. But then that can help get to a place where you get to that, like, flywheel effect as you're kind of building your product of, as you're able to solve things quickly, that means you have more time to invest in other parts of the product, and so on and so forth. So, yeah, it's one of those things where kind of the earlier you can get started on that, the more that benefit gets amplified over time. And thankfully, with Datadog and other offerings like that now, you can get started with that relatively quickly, right? You're not having to necessarily make the choice of, like, oh, can I justify spending a week, a month, whatever, setting up all my own infrastructure for this, as opposed to, you know, plugging in a credit card and getting going right away? And not necessarily starting with everything from day zero but getting started with something and then being able to build on that definitely can be a worthwhile trade-off. [laughs] VICTORIA: That makes sense. And I'm curious your perspective, Will, as a developer on our Lift Off team, which is really about the services around that time when you want to start taking it really seriously. Like, you've built an app [laughs]. You know it's a viable product, and there's a market for it. And just, like, how you think about observability when you're doing your app building. WILL: The approach I really take is, like, what is the end goal? I'm currently on a project right now that we came in later than normal. We're trying to work through that. SEAN: I haven't come from, you know, that kind of consulting and professional services and support kind of place. I'm curious about, like, what, if any, differences or experiences do you have, like, in that context of, like, how do you use your observability tools or, like, what value they have as opposed to maybe more, like, straight product development? VICTORIA: Right. So, we recently partnered with, you know, our platform engineering team worked with the Lift Off team to create a product from scratch. And we built in observability tools with Prometheus, and Grafana, and Sentry so that the developers could instrument their app and build metrics around the performance in the way they expected the application to work so that when it goes live and meets real users, they're confident their users are able to actually use the app with a general acceptable level of latency and other things that are really key to the functionality of the app. And so, I think that the interesting part was, with the founders who don't have a background in IT operations or application monitoring and performance, it sort of makes sense. But it's still maybe a stretch to really see the full value of that, especially when you're just trying to get the app out the door. SEAN: Nice. VICTORIA: [chuckles] That's my answer. What kind of challenges do you have in your role managing this large team in a very competitive company, running a ton of Kubernetes clusters? [laughs] What's your challenges in your director of engineering role there? SEAN: You know, it's definitely a mix of kind of, like, technical or strategic challenges there, as well as people challenges. On the technical and strategic side, the interesting thing for our team right now is we're in the middle of a very interesting transition. Still, today, the teams at Datadog work in very much a 'You build it, you run it' kind of model, right? So, teams working on user-facing features in addition to, like, you know, designing those features and writing the code for that, they're responsible for deploying that code, offering the services that code runs within, being on call for that, so on and so forth. And until relatively recently, that ownership was very intense to the point where some teams maybe even had their own build and release processes. They were running their own data stores. And, like, that was very valuable for much of our history because that let those teams to be very agile and not have to worry about, like, convincing the entire company to change if they needed to make some kind of change. But as we've grown and as, you know, we've kind of taken on a lot more complexity in our environment from, you know, running across more providers, running across more regions, taking on more of regulatory concerns, to kind of the viability of running everything entirely [inaudible 12:13] for those product teams, it has become much harder. [laughs] You start to see a transition where previously the infrastructure teams were much more acting as subject matter experts and consultants to, now, we're increasingly offering more centralized platforms and offerings that can offload a lot of that kind of complexity and the stuff that isn't the core of what the other product-focused teams are trying to do. And so, as we go through that change, it means internally, a lot of our teams, and how we think about our roles, and how we go about doing our work, changes from, like, a very, you know, traditional reliability type one on one consultation and advising type role to effectively internal product development and internal platform development. So, that's a pretty big both mindset and practice shift. [laughs] So, that's one that we're kind of evolving our way through. And, of course, as what happens to kind of things, like, you still have to do all the old stuff while you're doing the new thing. [laughs] You don't get to just stop and just do the new thing. So, that's been an interesting kind of journey and one that we're always kind of figuring out as we go. That is a lot of kind of what I focus on. You know, people wise, you know, we have an interesting aim of...There's about 40 people in my org. They are spread across EMEA and North America with kind of, let's say, hubs in New York and Paris. So, with that, you know, you have a pretty significant time zone difference and some non-trivial cultural differences. [laughs] And so, you know, making sure that everybody is still able to kind of work efficiently, and communicate effectively, and collaborate effectively, while still working within all those constraints is always an ongoing challenge. [laughs] WILL: Yeah, you mentioned the different cultures, the different types of employees you have, and everyone is not the same. And there's so many cultures, so many...whatever people are going through, you as a leader, how do you navigate through that? Like, how do you constantly challenge yourself to be a better leader, knowing that not everyone can be managed the same way, that there's just so much diversity, probably even in your company among your employees? SEAN: I think a lot of it starts from a place of listening and paying attention to kind of just see where people are happy, where they feel like they have unmet needs. As an example, I moved from that last kind of data store-focused team to this computing cloud team last November. And so, as part of that move, probably for the first two or three months that I was in the role, I wasn't particularly driving much in the way of changes or setting much of a vision beyond what the team already had, just because as the new person coming in, it's usually kind of hard to have a lot of credibility and/or even just have the idea of, like, you know, like you're saying, like, what different people are looking for, or what they need, how they will respond best. I just spend a lot of time just talking to people, getting to know the team, building those relationships, getting to know those people, getting to know those groups. And then, from there, figuring out, you know, both where the kind of the high priority areas where change or investment is needed. But then also figuring out, yeah, kind of based on all that, what's the right way to go about that with the different groups? Because yeah, it's definitely isn't a one size fits all solution. But for me, it's always kind of starting from a place of listening and understanding and using that to develop, I guess, empathy for the people involved and understanding their perspectives and then figuring it out from there. I imagine–I don't know, but I imagine thoughtbot's a pretty distributed company. How do you all kind of think about some of those challenges of just navigating people coming from very different contexts? WILL: Yeah, I was going to ask Victoria that because Victoria is one of the leaders of our team here at thoughtbot. So, Victoria, what are your thoughts on it? VICTORIA: I have also one of the most distributed teams at thoughtbot because we do offer 24/7 support to some clients. And we cover time zones from the Pacific through West Africa. So, we just try to create a lot of opportunities for people to engage, whether it's remotely, especially offering a lot of virtual engagement and social engagement remotely. But then also, offering some in-person, whether it's a company in-person event, or encouraging people to engage with their local community and trying to find conferences, meetups, events that are relevant to us as a business, and a great opportunity for them to go and get some in-person interaction. So, I think then encouraging them to bring those ideas back. And, of course, thoughtbot is known for having just incredible remote async communication happening all the time. It's actually almost a little oppressive to keep up with, to be honest, [laughs] but I love it. There's just a lot of...there's GitHub issues. There's Slack communications. There's, like, open messages. And people are really encouraged to contribute to the conversation and bring up any idea and any problem they're having, and actively add to and modify our company policies and procedures so that we can do the best work with each other and know how to work with each other, and to put out the best products. I think that's key to having that conversation, especially for a company that's as big as Datadog and has so many clients, and has become such a leader in this metrics area. Being able to listen within your company and to your clients is probably going to set you up for success for any, like, tech leadership role [laughs]. I'm curious, what are you most excited about now that you've been in the role for a little while? You've heard from a lot of people within the company. Can you share anything in your direction in the next six months or a year that you're super excited about? SEAN: So, there's usually kind of probably two sides to that question of kind of, like, from a product and business standpoint and from an internal infrastructure standpoint, given that's where my day-to-day focus is. You know, on the product side, one thing that's been definitely interesting to watch in my time at Datadog is we really made the transition from kind of, like, a point solution type product to much more of a platform. For context, when I joined Datadog, I think logs had just gone GA, and APM was in beta, I think. So, we were just starting to figure out, like, how we expand beyond the initial infrastructure metrics product. And, obviously, at this point, now we have a whole, you know, suite of offerings. And so, kind of the opportunities that come with that, as far as both different spaces that we can jump into, and kind of the value that we can provide by having all those different capabilities play together really nicely, is exciting and is cool. Like, you know, one of the things that definitely lit an interesting light bulb for me was talking to some of the folks working on our newer security offerings and them talking about how, obviously, you want to meet, you know, your normal requirements in that space, so being able to provide the visibility that, you know, security teams are looking for there. But also, figuring out how we integrate that information into your developers' everyday experience so that they can have more ownership over that aspect of the systems that they're building and make everybody's job easier and more efficient, right? Instead of having, you know, the nightmare spreadsheet whenever a CVE comes out and having some poor TPM chase half the company to get their libraries updated, you know, being able to make that visible in the product where people are doing their work every day, you know, things like that are always kind of exciting opportunities. On the internal side, we're starting to think about, like, what the next major evolution of our kind of Kubernetes and kind of internal build and release tooling looks like. Today, a lot of kind of how teams interact with our Kubernetes infrastructure is still pretty raw. Like, they're working directly with specific Kubernetes clusters, and they are exposed to all the individual Kubernetes primitives, which is very powerful, but it's also a pretty steep learning curve. [laughs] And for a lot of teams, it ends up meaning that there's lots of, you know, knobs that they have to know what they do. But at the end of the day, like, they're not getting a lot of benefit from that, right? There's more just opportunity for them to accidentally put themselves in a bad place. So, we're starting to figure out, like, higher level abstractions and offerings to simplify how all that for teams look like. So, we're still a bit early days in working through that, but it's exciting to figure out, like, how we can still give teams kind of the flexibility and the power that they need but make those experiences much easier and not have to have them become Kubernetes experts just to deploy a simple process. And, yes, so there's some lots of fun challenges in there. [laughs] Mid-Roll Ad: When starting a new project, we understand that you want to make the right choices in technology, features, and investment but that you don’t have all year to do extended research. In just a few weeks, thoughtbot’s Discovery Sprints deliver a user-centered product journey, a clickable prototype or Proof of Concept, and key market insights from focused user research. We’ll help you to identify the primary user flow, decide which framework should be used to bring it to life, and set a firm estimate on future development efforts. Maximize impact and minimize risk with a validated roadmap for your new product. Get started at: tbot.io/sprint. WILL: I have a question around your experience. So, you've been a developer around 20 years. What has been your experience over that 20 years or about of the growth in this market? Because I can only imagine what the market was, you know, in the early 2000s versus right now because I still remember...I still have nightmares of dial-up, dial tone tu-tu-tu. No one could call you, stuff like that. So, what has been your experience, just seeing the market grow from where you started? SEAN: Sure, yeah. I think probably a lot of the biggest pieces of it are just seeing the extent to which...I want to say it was Cory Doctorow, but I'm not sure who actually originally coined the idea, but the idea that, you know, software is eating the world, right? Like, eventually, to some degree, every company becomes a software company because software ends up becoming involved in pretty much everything that we as a society do. So, definitely seeing the progression of that, I think, over that time period has been striking, you know, especially when I was working in more consulting contexts and working more in companies and industries where like, you know, the tech isn't really the focus but just how much that, you know, from an engineering standpoint, relatively basic software can fundamentally transform those businesses and those industries has definitely been striking. And then, you know, I think from a more individual perspective, seeing as, you know, our tools become more sophisticated and easier to access, just seeing how much of a mixed bag that has become [laughs]. And just kind of the flavor of, like, you know, as more people have more powerful tools, that can be very enabling and gives voice to many people. But it also means that the ability of an individual or a small group to abuse those tools in ways that we're maybe not fully ready to deal with as a society has been interesting to see how that's played out. VICTORIA: Yeah. I think you bring up some really great points there. And it reminds me of one of my favorite quotes is that, like, the future is here—it's just not evenly distributed. [laughs] And so, in some communities that I go to, everyone knows what Kubernetes is; everyone knows what DevOps is. It's kind of, like, old news. [laughs] And then, some people are still just like, "What?" [laughs]. It's interesting to think about that and think about the implications on your last point about just how dangerous the supply chain is in building software and how some of these abstractions and some of these things that just make it so easy to build applications can also introduce a good amount of risk into your product and into your business, right? So, I wonder if you can tell me a little bit more about your perspective on security and DevSecOps and what founders might be thinking about to protect their IP and their client's data in their product. SEAN: That one is interesting and tricky in that, like, we're in a little bit of, like, things are better and worse than they ever have been before [laughs], right? Like, there is a certain level of, I think, baseline knowledge and competency that I think company leaders really just have to have now, part of, like, kind of table stakes, which can definitely be challenging, and that, like, that probably was much less, if even the case, you know, 10-20 years ago in a lot of businesses. As an example, right? Like, obviously, like if it's a tech-focused company, like, that can be a thing. But, like, if you're running a plumbing business with a dozen trucks, let's say, like, 20 years ago, you probably didn't have to think that much about data privacy and data security. But, like, now you're almost certainly using some kind of electronic system to kind of manage all your customer records, and your job scheduling, and all that kind of stuff. So, like, now, that is something that's a primary concern for your business. On the flip side of that, I think there is much better resources, and tools, and practices available out there. I forget the name of the tool now. But I remember recently, I was working with a company on the ISO long string of numbers certifications that you tend to want to do when you're handling certain types of data. There was a tool they were able to work with that basically made it super easy for them to, like, gather all the evidence for that and whatnot, in a way where, like, you know, in the past, you probably just had to hire a compliance person to know what you had to do and how to present that. But now, you could just sign up for a SaaS product. And, like, obviously, it can't just do it for you. Like, it's about making your policies. But it still gave you enough support where if you're, like, bootstrapping a company, like, yeah, you probably don't need to hire a specialist to [inaudible 25:08], which is a huge deal. You know, similarly, a lot of things come much safer by default. When you think about, like, the security on something like an iPhone, or an iPad, or an Android device, like, just out of the box, that's light-years ahead of whatever Windows PC you were going to buy ten years ago. [laughs] And so, that kind of gives you a much better starting place. But some interesting challenges that come with that, right? And that we do now, literally, every person on the planet is walking around with microphones and cameras and all kinds of sensors on them. It's an interesting balance, I think. Similarly, I'm curious how you all think about kind of talking with your clients and your customers about this because I'm sure you all have a non-trivial amount of education to do there. [laughs] VICTORIA: Yeah, definitely. And I think a lot of it comes in when we have clients who are very early founders, and they don't have a CTO or a technical side of their business, and advising them on exactly what you laid out. Like, here's the baseline. Like, here's where you want to start from. We generally use the CIS controls, this internet for internet security. It puts out a really great tool set, too, for some things you were mentioning earlier. Let's figure out how to report and how to identify all of the things that we're supposed to be doing. It could be overwhelming. It's a lot. Like, in my past role as VP of Operations at Pluribus Digital, I was responsible for helping our team continue to meet our...we had three different ISO long number certifications [laughs]. We did a CMMI as well, which has come up a few times in my career. And they give you about a couple of hundreds of controls that you're supposed to meet. It's in very kind of, like, legalese that you have to understand. And that's a pretty big gap to solve for someone who doesn't have the technical experience to start. Like, what you were saying, too, that it's more dangerous and more safer than it has been before. So, if we make choices for those types of clients in very safe, trusted platforms, then they're going to be set up for success and not have to worry about those details as much. And we kind of go forward with confidence that if they are going to have to come up against compliance requirements or local state regulations, which are also...there's more of those every day, and a lot of liability you can face as a founder, especially if you're dealing with, like, health or financial data, in the state of California, for example. [laughs] It puts you at a really big amount of liability that I don't think we've really seen the impact of how bad it can be and will be coming out in the next couple of years now that that law has passed. But that's kind of the approach that we like to think. It's like, you know, there's a minimum we can do that will mitigate a lot of this risk [laughs], so let's do that. Let's do the basics and start off on the right foot here. SEAN: Yeah, no, that makes sense. Yeah, it's definitely something I've come to appreciate, especially doing work in regulated spaces is, when you do reach the point where you do need to have some kind of subject matter expert involved, whether it's somebody in-house or a consultant or an advisor, I've definitely learned that usually, like, the better ones are going to talk to you in terms of, like, what are the risk trade-offs you're making here? And what are the principles that all these detailed controls or guidelines are looking to get at? As opposed to just, like, walking you through the box-checking exercise. In my experience, a really good lawyer or somebody who will talk to you about risk versus just saying whether or not you can do something. [laughs] It has a very similar feeling in my experience. VICTORIA: Yeah, it's a lot about risk. And someone's got to be able to make those trade-off decisions, and it can be really tough, but it's doable. And I think it shouldn't scare people away. And there's lots of people, lots of ways to do it also, which is exciting. So, I think it's a good space to be in and to see it growing and pay attention to. [laughs] It's fun for me to be in a different place where we're given the opportunity to kind of educate or bring people along in a security journey versus having it be a top-down executive-level decision that we need to meet this particular security standard, and that's the way it's going to be. [laughs] Yeah, so that I appreciate. Is there anything that really surprised you in your conversations with Datadog or with other companies around these types of services for, like, platform engineering and observability? Is there anything that surprised you in the discovery process with potential clients for your products? SEAN: I think one of the biggest surprises, or maybe not a surprise but an interesting thing is, to what extent, you know, for us, I don't know if this is still the case, but I think in many places, like, we're probably more often competing against nothing than a competing product. And by that, I mean, especially as you look at some of our more sophisticated products like APM, or profiling, it's not so much that somebody has an existing tool that we're looking to replace; it's much more than this is just not a thing they do today. [laughs] And so, that leads to a very interestingly different conversation that I think, you know, relates to some of what we were saying with security where, you know, I think a non-trivial part of what our sales and technical enablement folks do is effectively education for our customers and potential customers of why they might want to use tools like this, and what kind of value they could get from them. The other one that's been interesting is to see how different customers' attitudes around tools like this have evolved as they've gone through their own migration to the cloud journeys, right? We definitely have a lot of customers that, I think, you know, 5, 10 years ago, when they were running entirely on-prem, using a SaaS product would have been a complete non-starter. But as they move into the cloud, both as they kind of generally get more comfortable with the idea of delegating some of these responsibilities, as well as they start to understand kind of, like, the complexity of the tooling required as their environment gets more complex, the value of a dedicated product like something like Datadog as opposed to, you know, what you kind of get out of the box with the cloud providers or what you might kind of build on your own has definitely been interesting. [laughs] VICTORIA: Is there a common point that you find companies get to where they're like, all right, now, I really need something? Can you say a little bit more about, like, what might be going on in the organization at that time? SEAN: You know, I think there could be a few different paths that companies take to it. Some of it, I think, can come from a place of...I think, especially for kind of larger enterprise customers making a transition like that, they tend to be taking a more holistic look at kind of their distinct practices and seeing what they want to change as they move into the cloud. And often, kind of finding an observability vendor is just kind of, like, part of the checklist there. [laughs] Not to dismiss it, but just, like, that seems to be certainly one path into it. I think for smaller customers, or maybe customers that are more, say, cloud-native, I think it can generally be a mix of either hitting a point where they're kind of done with the overhead of trying to maintain their own infrastructure of, like, trying to run their own ELK stack and, like, build all the tooling on top of that, and keeping that up and running, and the costs associated with that. Or, it's potentially seeing the sophistication of tooling that, like, a dedicated provider can afford to invest that realistically, you're never going to invest in on your own, right? Like, stuff like live profiling is deeply non-trivial to implement. [laughs] I think especially once people get some experience with a product like Datadog, they start thinking about, like, okay, how much value are we actually getting out of doing this on our own versus using a more off-the-shelf product? I don't know if we've been doing it post-COVID. But I remember pre-COVID...so Datadog has a huge presence at re:Invent and the other similar major cloud provider things. And I remember for a few years at re:Invent, you know, we obviously had, like, the giant 60x60 booth in the main expo floor, where we were giving demos and whatnot. But they also would have...AWS would do this, like, I think they call it the interactive hall where companies could have, like, more hands-on booths, and you had, like, a whole spectrum of stuff. And there were, like, some companies just had, like, random, like, RC car setups or Lego tables, just stuff like that. But we actually did a setup where there was a booth of, I think, like, six stations. People would step up, and they would race each other to solve a kind of faux incident using Datadog. The person who would solve it first would win a switch. I think we gave away a huge number of switches as part of that, which at first I was like, wow, that seems expensive. [laughs] But then later, you know, I was mostly working the main booth at that re:Invent. So by the, like, Wednesday and Thursday of re:Invent, I'd have people walking up to the main booth being like, "Hey, so I did the thing over at the Aria. And now I installed Datadog in prod last night, and I have questions." I was like, oh, okay. [laughs] So, I think just, like, the power of, like, getting that hands-on time, and using some of the tools, and understanding the difference there is what kind of gets a lot of people to kind of change their mind there. [laughs] VICTORIA: You'd get me with a switch right now. I kind of want one, but I don't want to buy one. SEAN: [laughs] WILL: Same. [laughs] VICTORIA: Because I know it'll take up all my time. SEAN: Uh-huh. That's fair. [laughs] VICTORIA: But I will try to win one at a conference for sure. I think that's true. And it makes sense that because your product is often going with clients that don't have these practices yet, that as soon as you give them exposure to it, you see what you can do with it, that becomes a very powerful selling tool. Like, this is the value of the product, right? [laughs] SEAN: Yeah, there is also something we see, and I think most of our kind of peers in the industry see is, very often, people come in initially looking for and using a single product, like, you know, infrastructure, metrics, or logs. And then, as they see that and see where that touches other parts of the product, their usage kind of grows and expands over time. I would obviously defer to our earnings calls for exact numbers. But generally speaking, more or less kind of half of our new business is usually expanded usage from existing customers as opposed to new customers coming in. So, I think there's also a lot of just kind of organic discovery and building of trust over time that happens there, which is interesting. VICTORIA: One of my favorite points to make, which is that SRE sounds very technical and, like, this really extreme thing. But to make it sound a little more easier, is that it is how you validate that the user experience is what you expect it to be. [laughs] I wonder if you have any other thoughts you want to add to that, just about, like, SRE and user experience and how that all connects for real business value. SEAN: I think a lot of places where, you know, we've both seen internally ourselves and with customers is, you know; obviously, different companies operate in different models and whatnot. Where people have seen success is where, you know, people with formal SRE titles or team names can kind of be coming in as just kind of another perspective on the various kind of things that teams are trying to drive towards. The places reliability is successfully integrated is when they can kind of make that connection that you were talking about. It's, like, obviously, everybody should go take their vitamins, but, like, what actual value is coming from this, right? Nobody wants to have outages, but, like, to do the work to invest in reliability, often, like, it can be hard to say, like, okay, what's the actual difference between before and after? Having people who can help draw those connections and help weigh those trade-offs, I think, can definitely be super helpful. But it is generally much more effective, I think, in my experience, when it does come from that perspective of, like, what value are we providing? What are we trading off as part of this? As opposed to just, well, you should do this because it's the right thing to do, kind of a moralistic perspective. [laughs] But, I don't know, how do you all kind of end up having that conversation with your customers and clients? VICTORIA: That's exactly it. That's the same. It's starting that conversation about, like, well, what happens when this experience fails, which designers don't necessarily think about? What's, like, the most important paths that you want a user to take through your application that we want to make sure works? And when you tie it all back there, I think then when the developers are understanding how to create those metrics and how to understand user behavior, that's when it becomes really powerful so that they're getting the feedback they need to do the right code, and to make the right changes. Versus just going purely on interviews [laughs] and not necessarily, like, understanding behavior within the app. I think that starts to make it clear. SEAN: Part of that, I think that's been an interesting experience for us is also just some of the conversation there around, like, almost the flip side of, when are you investing potentially too much in that, right? Because, like, especially after a certain point, the cost of additional gains grows exponentially, right? Each one of those nines gets more and more expensive. [laughs] And so, having the conversation of, like, do you actually need that level of reliability, or, like, is that...just like what you're saying. Like, you know, kind of giving some of that context and that pressure of, like, yeah, we can do that, but, like, this is what it's going to cost. Is that what you want to be spending your money on? Kind of things can also be an interesting part of that conversation. VICTORIA: That's a really good point that, you know, you can set goals that are too high [laughs] and not necessary. So, it does take a lot of just understanding about your data and your users to know what are acceptable levels of error. I think the other thing that you can think about, too, like, what could happen, and we've seen it happen with some startups, is that, like, something within the app is deeply broken, but you don't know. And you just think that you're not having user engagement, or that users are signing off, or, like, you know, not opening the app after the first day. So, if you don't have any way to really actively monitor it and you're not spending money on an active development team, you can have some method to just be confident that the app is working and to make your life less miserable [laughs] when you have a smaller team supporting, especially if you're trying to really minimize your overhead for running an application. SEAN: Yep. It's surprisingly hard to know when things are broken sometimes. [laughs] VICTORIA: Yes, and then extremely painful when you find out later [laughs] because that's when it's become a real problem, yeah. I wonder, are there any other questions you have for me or for Will? SEAN: How big of an organization is thoughtbot at this time? VICTORIA: Close to 75 people? We're, yeah, between the Americas and the [inaudible 38:31] region. So, that's where we're at right now, yeah. SEAN: Nice. At that size, like, and I guess it sounds like you're pretty heavily distributed, so maybe some of this doesn't happen as much, but, like, one of the things I definitely remember...so, when I joined Datadog, it was probably about 500 people. And I think we're just under 5,000 now. There are definitely some points where there were surprisingly, like, physical aspects to where it became a problem of just, like, where certain teams didn't fit into a room anymore. [laughs] Like, I had surprise in the changes in that, like, dynamic. I'm curious if you've all kind of run into any kind of, I don't know, similar interesting thresholds or changes as you've kind of grown and evolved. WILL: I will say this, we're about 100, I think, Victoria. VICTORIA: Oh, okay, we're 100 people. I think, you know, I've only been at thoughtbot for just over a year now. And my understanding of the history is that when we were growing before COVID, there's always been a very intentionality about growth. And there was never a goal to get to a huge size or to really grow beyond just, like, a steady, profitable growth. [laughs] So, when we were growing in person, there were new offices being stood up. So, we, you know, maybe started out of New York and Boston and grew to London. And then, there was Texas, and I think a few other ones that started. Then with COVID, the decision was made to go fully remote, and I think that's opened up a lot of opportunities for us. And from my understanding in the previous and the past, is that there's a big shift to be fully remote. It's been challenging, where I think a lot of people miss some of the in-person days, and I'm sure it's definitely lonely working remote all day by yourself. So, you have to really proactively find opportunities to see other people and to engage remotely. But I think also, we hire people from so many different places and so much different talent, and then, also, you know, better informs our products and creates a different, you know, energy within the company that I think is really fun and really exciting for us now. WILL: Yeah, I would agree with that because I think the team that I'm on has about 26 people on the Lift Off team. And we're constantly thinking of new ways to get everyone involved. But as a developer, me myself being remote, I love talking to people. So, I try to be proactive and, like, connect with the people I'm working with and say, "Hey, how can I help you with this?" Let's jump in this room and just work together, chat together, and stuff like that, so... And it has opened the door because the current project that I'm on, I would never have had an opportunity to be on. I think it's based in Utah, and I'm in South Florida. So, there's just no way if we weren't remote that I'd been a part of it. So... SEAN: Nice. And I can definitely appreciate that. I remember when we first started COVID lockdown; I think, at that point, Datadog was probably about...Datadog engineering was probably about 30% remote, so certainly a significant remote contingent but mixed. But my teams were pretty remote-heavy. So, in some ways, not a lot changed, right? Like, I think more people on my team were, like, who are all these other people in my house now instead of [laughs], I mean, just transition from being in an office to working from home. But I do remember maybe, like, about six months in, starting to feel, yeah, some of the loneliness and the separation of just, like, not being able to do, like, quarterly team meetups or stuff like that. So, it's definitely been an interesting transition. For context, at this point, we kind of have a hybrid setup. So, we still have a significant kind of full-time remote contingent, and then four people who are in office locations, people joining for about three days a week in office. So, it's definitely an interesting transition and an interesting new world. [laughs] VICTORIA: Yeah. And I'm curious how you find the tech scene in Denver versus New York or if you're engaging in the community in the same way since you moved. SEAN: There definitely is some weirdness since COVID started [laughs] broadly [inaudible 42:21]. So, I moved here in 2020. But I'd been coming out here a lot before that. I helped to build an office here with Bitly. So, I was probably coming out once a quarter for a bunch of years. So, one parallel that is finally similar is, like, in both places, it is a small world. It doesn't take that long for you to be in that community, in either of those communities and start running into the same people in different places. So, that's always been [inaudible 42:42] and especially in New York. New York is a city of what? 8, 9 million people? But once you're working in New York tech for a few years and you go into some meetups, you start running into the same people, and you have one or two degrees [inaudible 42:52] to a lot of people, surprisingly quickly. [laughs] So, that's similar. But Denver probably is interesting in that it's definitely transplant-heavy. I think Denver tends to check the box for, like, it was part of why Bitly opened an office here and, to a degree, Datadog as well. I think of like, you know, if you're trying to recruit people and you previously were mostly recruiting in, like, New York or Silicon Valley; if you're based in New York, and you're trying to recruit somebody from Silicon Valley, and part of why they're looking for a new gig is they're burned out on Silicon Valley, asking them to move to New York probably isn't all that attractive. [laughs] But Denver is different enough in that in terms of kind of being a smaller city, easier access to nature, a bunch of that kind of stuff, that a lot of times we were able to attract talent that was a much more appealing prospect. [laughs] You'll see an interesting mix of industries here. One of the bigger things here is there's a very large government and DOD presence here. I remember I went to DevOps Days Rockies, I think, a few years ago. There was a Birds of a Feather session on trying to apply DevOps principles in air-gapped networks. That was a very interesting conversation. [laughs] VICTORIA: That's interesting. I would not have thought Colorado would be a big hub for federal technology. But there you go, it's everywhere. WILL: Yeah. SEAN: Denver metro, I think, is actually the largest presence of federal offices outside of the D.C. metro. VICTORIA: That's interesting. Yeah, I'm used to trying to recruit people into D.C., and so, it's definitely not the good weather, [laughs], not a good argument in my favor. So, I just wanted to give you a final chance. Anything else you'd like to promote, Sean? SEAN: Generally, not super active on social things these days, but you can find whatever I have done at seanoc.com, S-E–A-N-O-C.com for the spelling. And otherwise, if you're interested in some engineering content and hearing about some of those kind of bleeding edge challenges that I was mentioning before, I would definitely check out the Datadog engineering blog. There's lots of kind of really interesting content there on both, you know, things we've learned from incidents and interesting projects that we're working on. There's all kinds of fun stuff there. VICTORIA: That makes me think I should have asked you more questions, Sean. [laughs] No, I think it was great. Thank you so much for joining us today. I'll definitely check all that stuff out. You can subscribe to the show and find notes along with a complete transcript for this episode at giantrobots.fm. If you have questions or comments, email us at hosts@giantrobots.fm. You can find me on Twitter @victori_ousg. WILL: And you can find me on Twitter @will23larry. This podcast is brought to you by thoughtbot and produced and edited by Mandy Moore. Thanks for listening. See you next time. ANNOUNCER: This podcast is brought to you by thoughtbot, your expert strategy, design, development, and product management partner. We bring digital products from idea to success and teach you how because we care. Learn more at thoughtbot.com.Special Guest: Sean O'Connor.Sponsored By:thoughtbot: When starting a new project, we understand that you want to make the right choices in technology, features, and investment, but that you don’t have all year to do extended research. In just a few weeks, thoughtbot’s Discovery Sprints deliver a user-centered product journey, a clickable prototype or Proof of Concept, and key market insights from focused user research. We’ll help you to identify the primary user flow, decide which framework should be used to bring it to life, and set a firm estimate on future development efforts. Maximize impact and minimize risk with a validated roadmap for your new product. Get started at: tbot.io/sprintSupport Giant Robots Smashing Into Other Giant Robots

Kendall Miller is the Co-Founder and COO of CTO Lunches, a network of engineering leaders to get trusted advice and connections. The first half of the conversation with host Victoria Guido and special guest host, Joe Ferris, CTO of thoughtbot revolves around the use, adoption, and growth of Kubernetes within the technology industry. The discussion explores Kubernetes' history, influence, and its comparison with other platforms like Heroku and WordPress, emphasizing its adaptability and potential. The second half focuses on more practical aspects of Kubernetes, including its adoption and scalability. It centers on the appropriateness of adopting Kubernetes for different projects and how it can future-proof infrastructure. The importance of translating technical language into business speak is emphasized to influence executives and others in the decision-making process and Kendall also discuss communication and empathy in tech, particularly the skill of framing questions and understanding others' emotional states. __ CTO Lunches Follow CTO Lunches on LinkedIn or Twitter. Follow Kendall Miller on LinkedIn. Follow thoughtbot on Twitter or LinkedIn. Become a Sponsor of Giant Robots! Transcript: VICTORIA: This is the Giant Robots Smashing Into Other Giant Robots Podcast, where we explore the design, development, and business of great products. I'm your host, Victoria Guido. And with me today is Kendall Miller, Co-Founder and COO of CTO Lunches, a network of engineering leaders to get trusted advice and connections. Kendall, thank you for joining me. KENDALL: Thanks for having me. I'm excited. VICTORIA: And today, we have a special guest host, Joe Ferris, CTO of thoughtbot. Joe, thank you for joining us. JOE: Hello there. Thank you for having me. KENDALL: Hi, Joe. Thanks for being here. It's exciting. VICTORIA: Yes. It's so exciting. I think this is going to be a great episode. So, Kendall, I met you at a San Diego CTO lunch recently, and I know that's not the only thing that you do. So, you're also an advisor, a board member, and CXO. So, maybe tell us a little bit more about your background. KENDALL: Gosh, my background is complicated. I've been involved in tech for a very long time. In college, I worked for a company that started Twitter about five years too soon, and then worked in the nonprofit space in China for ten years, then came back, got back involved in tech. Today, I'm usually the business guy. So, when technical founders start technical products and want help turning them into successful technical businesses, that's when they call me. So, I have the technical background. I have never been paid to write code, which is probably a good thing. But I can hang in the technical conversations for the most part, but I'm much more interested in the business side and the people leadership side of business. So that tends to be where I play. Every organization hires me to do something different. VICTORIA: Thank you for that. And I'm just curious about the CTO Lunches. Just tell me a little bit more about that. And what's the idea behind it that led you to co-found it? KENDALL: CTO Lunches has actually been around for about eight years. And I didn't start the initial incarnation of it. It was two people that got us started, and I was trying to hire one of them; one thing led to another. Actually, originally, they did not want me to join. I think, at the time, my title was COO at a company that I was working with. About six months later, I took over engineering as VP of engineering, and then they're like, you can join the group now. We're less strict about that [laughs] now. Although it is highly focused on senior engineering leaders, it's not exclusively CTOs. But the group's been in place for a very long time, just intended as a place to network, have conversation with people who are in that senior-most technical position at technical organization. So, the CTO role is a lonely role. CTOs get fired all the time. There's not a technical person at the company that doesn't think they can do the job better than them. So, the CTO is always getting feedback. You're doing this wrong. The trade-offs you're making are wrong. This isn't going where it should be going. We should automate that. Why haven't we automated that? We should switch to this other tool. I've used it before; it's 100 times better. Joe, let me know if I'm getting any of this wrong. But that's the experience that I've had. Having a place where people can get together and, you know, half the time just complain to each other, hey, this is hard, is really why the networking group exists. So, it's a listserv. And there are local lunches that started in Boulder, Colorado. It's gotten pretty global. About a year ago, a little over a year ago, I was talking with one of the people who'd gotten it started. I've been involved in the Denver chapter for most of those eight years. And I was suggesting to him that he change a few things about it, to monetize it so that he could invest in it further. And he came back a few months later and said, "I want to take your advice and do this, but I want you to come do it with me." So, we founded the company officially...I think in December is when paperwork went into place. And we started investing in it a little bit more heavily. I was living in Europe last year, so we went and put on lunches in Paris, and Lisbon, and London, and, gosh, all over the place. I'm sure I'm missing some, Amsterdam. But there's been chapters all over the U.S. and a couple of other parts of the world for a long time. VICTORIA: That reflects my experience attending a CTO lunch. It's just very casual, like, just get together and eat food and talk about what you've worked on recently, issues you're having, just get ideas and make some friends. So, I really appreciated the group, and I'm going to personally plug the San Diego Chapter has picked up again. And we're meeting next Friday down in Del Mar. And we're going to be meeting on the last Friday of every month through October. So, I'm super excited to be a part of the group. And Joe, yeah, I'm curious about your perspective. As a CTO with thoughtbot, just what are your thoughts about that kind of thing? KENDALL: Yeah. How right am I about how lonely you are, Joe? JOE: [laughs] You know, I've been lonelier since we went remote. I used to work in the office, and I was a CTO, but also, I had lunch with people, which was nice. So, I'm lonelier. But yeah, I think everybody needs a group like that, like, senior developer therapy just to talk about your woes together, drown your sorrows. KENDALL: Well, I think years ago, I heard that CTOs are the most fired C-level executive. JOE: You're making me nervous now. KENDALL: [laughs] You've been there a long time, Joe. I know you've been there a long time. If you haven't been fired yet, you probably got a little while longer in you. This will be really awkward if it's published and you've already been fired. VICTORIA: We can always edit that out afterwards. [laughter] KENDALL: Yeah, no, I think it is a particularly lonely position. And, again, I think a lot of it is the average engineer in a technical company doesn't look at the COO or the CFO or even the CEO and think I could do that. But they're all looking at the CTO and thinking, what does that person do that I can't do? It's ridiculous because most of them would make terrible CTOs because it does require some of the business sense. Or, you know, right out of the gate, they might make terrible CTOs. It actually is quite a skill to be the most technical person and speak the business language. I mean, am I right about that, Joe? Like, was that hard for you to learn? JOE: Yeah, I definitely think...so, my background is also technical. I have a background in consulting. So, I always did a lot of metaprogramming, if you will. But making that transition to thinking about organizations that way, thinking about how all the other pieces play into it, was a pretty big step for me, even before I became a CTO as a consultant. KENDALL: Well, because you can't just chase the newest, hottest technology. You have to make business trade-offs. And not everything can be resume-driven development, right? Even if that technology over there is newer or hotter, it doesn't mean you have a business model that supports it. And it doesn't mean that migrating to it can be done, right? JOE: Yeah. I mean, even beyond choosing technologies, just choosing where to invest in your software stack, like, what needs to be reworked, what doesn't, and trying to explain those trade-offs, I think, is a rare skill. Being able to explain why something would be harder than something else when you're working with the leadership to prioritize a backlog it's a puzzle. KENDALL: Well, and I think when I'm in an executive conversation, and the CTO says, "Here's the thing that I think is the best decision technically, and I think it's the wrong decision for the business because of X, Y, or Z," I'm always super impressed, right? Like, this is the right technical solution for what we want. However, we shouldn't pursue that for business reasons right now. Maybe we can in six months, but right now, we need to prioritize this other thing. I don't know, that's always when I feel like, oh, this person knows what they're doing. JOE: There's nothing more dangerous to software than a bored developer. [laughs] One nice thing about being a consultant is that I don't have to invent problems to solve with technology at my company because sooner or later, I'll run across a company that has those problems, and I'll get to use that technology. But I think a lot of people are mostly happy...they might be happy in their role. They might be happy with our team. But they're very interested in whatever is hot right now, like machine learning, AI. And so, suddenly, that surreptitiously makes its way into the tech stack. And then, years later, it's somebody's problem to maintain. KENDALL: [laughs] Well, I have a specific memory of a firm in New York City that was, you know, this is relevant to y'all as thoughtbot is that, you know, at least historically, it was, to me, the premier Ruby on Rails consulting shop. I think that's still largely y'alls focus. Am I right about that? JOE: We still do a ton of Rails, yeah. KENDALL: Okay. Well, so this organization was all Ruby on Rails. It was a big organization. They had a very large customer base. And they hired a new CTO who came in, told everybody in the company they were stupid, laid off 70% of the engineering organization, and told the CEO he was going to completely rewrite the product from scratch in .NET, and he could do it in three weeks. And I'm pretty sure the business went under about three months later [laughs] because that was just so outrageously nuts to me. JOE: It's too bad he laid everybody off beforehand. I've been in that situation where somebody tells me, "I'm going to rewrite this. It'll be ready in three weeks." And I could fight with them and try and convince them they're wrong. But I feel like somebody who's approaching that with that attitude they're missing all of the nuance and context that would make it possible to explain to them why it's not going to work. And so, it's easier to just say, "You know, take the three weeks. I'll talk to you in three weeks." But if you've already laid off your development team, that's hard [laughs] to recover from. KENDALL: That's exactly right. VICTORIA: There's got to be a name for that kind of CTO who just wants to come in and blow everything up [laughs]. Yeah, so you spend a lot of time talking to different CTOs and doing this social networking aspect. I'm wondering if there's, like, patterns that you see. You've mentioned already one about just, like, the most often getting fired. [laughs] But what are the patterns you see, like, in challenges, and then what makes someone successful in that CTO role? KENDALL: Well, oh gosh, I have so many thoughts about this. First of all, I run into a couple of different categories of CTOs. There's a lot of people who come to CTO Lunches who are small company CTOs. I mean, it makes sense that there's a lot more small company CTOs than there are big company CTOs. But the small company CTO who maybe it's their first gig in the role or they're a serial CTO. There's the fractional CTOs that come that are doing it across several different organizations at the same time, and then there's the big company CTO who shows up. And honestly, all of their problems are very different. The thing that they have in common is even at a very large organization, in that position, they can make a decision that causes the company to go under. So, there is a significant amount of volatility in the amount of power that they wield. So, what's interesting about that is not everybody understands that. And so, first of all, there's the kind of CTO that just doesn't get that, and that doesn't matter if they're fractional, or a small company CTO, or a big company CTO. If they don't understand that, they're going to cause significant problems, right? Like the person I just mentioned who said, "I can just re-platform this in three weeks in .NET." There's that. I mean, I think, as with any senior leadership position, the comfort with volatility, the ability to know what to communicate down versus across and versus up, and then the ability to speak the business language. For everybody, the CFO's job is to communicate the financial needs alongside of the business leads, right? If the CFO's sole goal is to cut costs or make sure we're running as lean as possible, they're a bad CFO. But they're not as good of a CFO as the CFO who can say, "Hey, we're underspending right here. And I can look at the numbers and know we should invest more there. How can we invest more there and invest it well?" And it's the same thing for a technology executive to be able to look at the business context and communicate it back. And there are so many CTOs that I've worked with who they're the most technical person in the room, and they know it. And as a result, they're just a jerk to everyone around them, like, everything you did here was wrong. You know, that's where they fail. And so, if they can communicate the business needs, navigate the volatility, and support a team that's going to make decisions that aren't always the same decision they're going to make, they're going to be successful. Honestly, there's very, very few CTOs that I've met like that. People who are excited to meet you at work, excited to see you succeed, excited to see that you went and built a thing is great. I mean, the reason I was VP of engineering is the CTO that I was working with at the time...it's a terrible story. There was an engineer who had seen something that we were doing on repeat all the time and, in his spare time, spent about 40 hours outside of work, not during work hours, automating this task that we were doing regularly. And it was related to standing up a whole bunch of things in our standard infrastructure. He brings it to the CTO and says, "Look what I built." And the CTO, instead of saying, "Hey, this is incredible. Thank you. This is going to save us a bunch of time. Let's iterate on it. Here's some things I'd like to tweak. Can we bring it in this direction? Can we..." you know, whatever, said, "Why is this in Python? It should be in Ansible," something like that. I can't remember. And the engineer literally burst into tears. [laughs] JOE: Oh my God. KENDALL: [laughs] Well, I mean, yeah, it was like; literally, that's why the CTO stopped managing people that day. There's a lot of examples that I have like that. Joe, I appreciate that your response is, "Oh my God." Because I think there's a lot of people who'd be like, wait, what was wrong with that? Shouldn't it have been in Ansible? JOE: [laughs] Yeah, I've seen CTOs come into primarily two groups. One is the CTO who just tells, you know, like, they make the decisions, and they tell everybody what to do. They obviously don't have all of the information because you can't be in every room all the time. And the other is the CTO, who just wants to be one of the team members and doesn't make any decisions and tries to get people to make decisions collectively on their own without any particular guidance or structure. And finding that middle spot of, like, not just saying, "Hey, everything's in Ansible," allowing for the creativity and initiative, but also coalescing the group into a single direction, I think, is what makes a good CTO. KENDALL: Well, yeah, because the CTO does have to say no, sometimes, right? Like, the best product, people say, "No." Good CTOs say, "No." There is some amount of, hey, I need you to come to me with trade-offs about this. Why are you going to make that decision? And I'm sorry, you still didn't convince me, right? Like, I mean, those are appropriate things to say. But yeah, I'm with you on that. You said they fall into two categories. But you really mean the third and that middle ground. Is it easy for you to walk that middle ground, Joe? JOE: I wouldn't say it's easy. [laughs] KENDALL: Yeah. Well, I'm always nervous to say something. I'm doing well because I know there's a report out there that can point at every time I failed at it, right? So... MID-ROLL AD: Are you an entrepreneur or start-up founder looking to gain confidence in the way forward for your idea? At thoughtbot, we know you’re tight on time and investment, which is why we’ve created targeted 1-hour remote workshops to help you develop a concrete plan for your product’s next steps. Over four interactive sessions, we work with you on research, product design sprint, critical path, and presentation prep so that you and your team are better equipped with the skills and knowledge for success. Find out how we can help you move the needle at: tbot.io/entrepreneurs. VICTORIA: Yeah, what I'm getting from what you're saying, too, is this communication ability and not just, like, to communicate clearly but with a high level of empathy. So, if you say like, "Well, why is it in Python and not Ansible?" is different than being like, "What makes Python the best solution here?" Like, it's a different way to frame the question that could put someone on the defensive that just really requires, like, a high level of emotional intelligence. And also, if they've just worked, like, an 80-hour week, [laughs] I probably would maybe choose a different time to bring those questions up and notice that they have been burning the candle at both ends and prioritize getting them some rest. So, speaking of, like, communication and getting prioritization for [inaudible 15:34], especially on, like, infrastructure teams, maybe we could talk a little bit about Kubernetes, like, when that comes up as an appropriate solution, and how you talk about it with the business. KENDALL: My background with Kubernetes is long because a company that I still work with, Fairwinds, used to be called ReactiveOps, has been in the Kubernetes space for a very long time. I think we were one of the very first companies working with Kubernetes. It was coming up that people were running into the limits of something like Heroku, right? And I think it's Kelsey Hightower who said every company wants a PaaS. They just want the Paas that they built themselves. And that's really accurate. And I think Kubernetes isn't quite a framework for building your own PaaS or isn't quite a foundation where I think of a foundation for a house. Instead, it's more like rebar and cement and somebody saying, "Good luck, buddy." You know, you still have to know how to put the rebar and cement together to even make the foundation, but it is the building blocks that help get you to a custom-built PaaS. And it's become something that a lot of people have landed on as, you know, the broadly accepted way to build cloud-native infrastructure. The reason I've been in the Kubernetes space and the space that I see Kubernetes still filling is we need to standardize on something. We can choose a cloud provider's PaaS. We can choose a third-party PaaS, or we can standardize on something like Kubernetes. And even though we're not going to migrate from AWS to Azure, the flexibility that Kubernetes gives us as a broadly adopted pattern is going to give us some ability to be future-proofed in our infrastructure in a way that previous stacks were not, you know, it was Puppet, and it was Ansible. And it was SaltStack. And it was all Terraform all the time. I'm not saying those things don't exist anymore. I'm saying Kubernetes kind of has won that battle. Joe, since you're here and I know y'all are doing some Kubernetes work now at thoughtbot, I'm curious if you agree with that characterization. JOE: Yeah, I think that's true. I think it's the center for people to coalesce around. Like, for an effort in the industry to move forward, there needs to be some common language, some common ground. And I think Kubernetes struck the right balance of being abstract. So, you can use it in different environments but still making some decisions, so you don't have to make them all. And so, like, all of the things you had to do with containers like figuring out what your data solution is going to be, what your networking solution is going to be, Kubernetes didn't even really make those decisions. [laughs] They just made a platform where those decisions can be made in a common way. And that allowed the community and the ecosystem to grow. KENDALL: I mean, I think of it a lot like WordPress; you know, WordPress is hated by many. When WordPress came out, it was hot, right? And it was PHP, which everybody was super excited about at the time. Kubernetes is going to reach a point where it's as long in the tooth and terrible as people think WordPress is, but it has become the standard. And the advantage of the standard is you can use the not standard. You can go build a website in Jekyll instead of WordPress, and there's going to be some things that are nicer about Jekyll. But because WordPress is so broadly adopted, there's a plugin for everything. And I think that's where Kubernetes sits is because it's become so widely adopted everybody's building for it. Everybody's adapting for it. If you run into a problem, you're going to find somebody else out there who has that problem. In fact, I think of one organization that I know that was on HashiCorp's Nomad. And they said, "Actually, we think Nomad has better technology through and through. But we think we're the only company at this size and scale using Nomad. And so, when we run into a problem, we can't Google for it. There's no such thing as a plugin that exists to solve this. Nobody has ever run into this before on Nomad. But there's 100 companies dealing with the same problem in Kubernetes, and there's ten solutions." And I think that's the power that it brings. VICTORIA: So, it's not just a trend that CTOs are moving towards, you think. KENDALL: I mean, I think it's already won the battle and the hockey stick of adoption. We're still right at the very bottom of that tick-up because it takes people a long time to adapt new technology like this, especially in their infrastructure. It's a big migration, to move. So, I don't think it's the widely adopted infrastructure technology even yet. I think a lot of the biggest organizations are still running on things that predate Kubernetes. But I think it has won the battle, and it is winning the battle and is going to be the thing going forward, so yeah. JOE: I think it also has a lot of room to grow still. Like, there are other technologies that I used previously, like Docker, and they were a big step up from some of the things I was doing at the time. But you quickly hit the ceiling, or it was, like, I don't know where to go with this next. I don't know what else is going to happen. Whereas with Kubernetes, there are so many directions it can go in. Like, the serverless Kubernetes offerings that are starting to pop up are extremely interesting, where, you know, you don't actually maintain a cluster or anything. You just deploy things to this ethereal cluster that always exists. And so, that sort of combination of platform as a service, function as a service, Kubernetes, as that evolves, I think there are a lot of exciting things that have yet to come in the Kubernetes space. KENDALL: Well, so say more about that, Joe, because I've been going to KubeCon for a very long time, maybe...I don't know if it's 2016 or so when I first went. And it felt for a number of years...maybe those first four-ish years it was always the people at KubeCon were the, like, big dreamers and thinkers and, like, we're here to change the future of cloud infrastructure. And this is going places, and we're excited to be here and be a part of it. And here's what I'm going to do that changes the next thing. And I feel like now if I go to KubeCon, it's a lot of people from, you know, IBM and some big bank that are, like, deep sigh, well, I have to adopt Kubernetes. I need to know what the vendors are. What do you guys do, and how does this work? Can you please teach it to me? Because I'm being told by my boss, I have to do it. I don't see that excitement around Kubernetes anymore. The excitement I see is all around further up the stack, you know, things like Wasm, WebAssembly, or eBPF, the networking things and tracing things that are possible. Maybe that's further down the stack. I guess it depends on how you think about it, but different part of the stack. So, I'm curious, touching on the serverless components of Kubernetes; sure, I get that. And I do think, increasingly, the PaaSs of the future are all going to be Kubernetes-based, whether that's exposed or not. But where are the places that you think it's still going to go? Because I feel like it's already gotten boring, maybe in a positive way. But I don't see the excitement around it like I saw a few years back. And I'm curious what else you think is going to happen. JOE: Yeah, I mean, I don't think I disagree. I think Kubernetes itself, the core concept, is, like, it's still changing. But you're right that the excitement about Kubernetes existing has gone down because it's been there for a while. But I feel like the ecosystem is still growing pretty rapidly. Like, the things you mentioned, like Wasm and Istio, and all the tools in that ecosystem that continue to grow, is where I think the interesting things will happen. Like, it's created this new lower-level layer of abstraction that makes it possible to build concepts and technology that could not have existed before. KENDALL: Yeah, well, and I'm, you know, talking to people who are working really hard at making short-run ephemeral workloads work better on things like GPUs for the sake of AI, right? Like, I mean, there is some really interesting things happening, and people are doing this in Kubernetes. So, I get that. I agree with that. It is interesting that Kubernetes has become sort of the stable thing, and now it's about who can build the interesting add-ons. It's almost like, okay, we've built Half-Life. What is Counter-Strike going to look like? You know. That's a terrible (I'm aging myself.) example. But still. VICTORIA: I think it's interesting, I mean, to look at the size of the market for platform engineering right now. In 2022, was 4.8 billion, and it's estimated to be in 10 years $41 billion. So, there is this emerging trend of different platform engineering products, different abstractions on top of Kubernetes. And I wonder what advice you would have for a technical founder who's looking to build and solve some of these interesting issues in Kubernetes and create a business around it. KENDALL: Well, okay, let me clarify that question. Are you thinking, I'm a startup, and I need to build my infrastructure, and I'm going to choose Kubernetes. What advice do I need? Or are you thinking, I am founder, and I want to go build on the Kubernetes ecosystem. What advice do you have? VICTORIA: Now I want to know the answer to both. But my question was the second one to start. KENDALL: One of the things that is hard about the Kubernetes ecosystem is there's not a ton of companies that have made a whole bunch of money in Kubernetes because, as I said, I still think we're actually really early in the adoption curve. The kinds of companies that have adopted Kubernetes are the kinds of companies that don't spend lots and lots of money on an infrastructure. [laughs] They're the kinds of companies that are fast-moving, early adopters, or, you know, those first followers, and so they're under $100 million companies for the most part. Where the JP Morgans and Chase are running Kubernetes somewhere in their stack, but they haven't adopted it across the stack to need the biggest, best tools about it. So, the first piece of advice that I'd give is, be a little wary. It's still very early to the market. Maybe now is the time to build the thing. When ReactiveOps pivoted to Kubernetes, I think it was six months of having conversations with companies who were just, like, so excited about it, and this is definitely what we want to do. But nobody was doing it yet. You know, it was, we have, like, six solid months of just excitement and nobody actually pulling the trigger. And, you know, we were a little too early to that market. And that was just the people adopting it. So, I think there is some nervousness that cloud-native solutions the only people who are really making money in Kubernetes are named Amazon, Google, and Microsoft because it's the cloud providers that are making a ton off of it. Now, there's Rancher. There is StackPointCloud. There's a few others that have had big exits in this space. But I don't think it's actually as big of a booming economy as a lot of people think, in part because EKS is an incredibly amazing product. Like, eight years ago, the thing people paid us the most to do at ReactiveOps was just stand up Kubernetes because it was so stinking hard to just get it up and working. And now you click some buttons. Anybody can go do that. So, it's changed a lot, right? And I think be wary when you're entering that ecosystem. And then, my advice to the founder that's not building on the ecosystem but just looking to adopt a technology that's going to be a future-proofed infrastructure is just adopt one of the cloud-native platforms. And there are a whole bunch of sort of default best-in-class add-ons out there that you need to throw in. Don't adopt too many because then you have to maintain them forever. That's the easiest way to get started. You can figure out all the rest of it later. But if you go use EKS, or GKE, AKS, you can get started pretty easily and build something that is going to be future-proofed. I don't know, Joe; I'm curious if you disagree with any of that. JOE: Well, I think it's interesting to think about who's making money in Kubernetes. Like, I think there might not be as many companies who are doing only Kubernetes and Kubernetes-focused products that are massively successful. But I think because it has had a good amount of adoption and because it's easier to work with something that's standardized, it has helped companies sell things that they wanted to sell anyway. Like, all the Datadog, all the Scalas, the logging companies, they all have Kubernetes add-ons. And now everybody is paying Datadog [laughs] to have a dashboard for their Kubernetes cluster. I think they're making more money than they would have been without targeting the market. And so, I think that's really...if you want to get into the market, it's not, like, I'm going to build a Kubernetes product. It's if I'm building operations and an infrastructure product, I should definitely have it work with Kubernetes, and people will want to click and install it. KENDALL: So, to be clear, you know, one of the companies that I work with is called Axiom, and they play in the same, you know, monitoring, observability space as Datadog does. And part of what makes Kubernetes interesting in that space is in a microservice environment; there's so much happening. Where are problems being caused? We don't live in a day where I can just run my code, and it tells me that there's an unexpected semicolon on line 23, right? Like, that still happens. You're still doing those things. But this microservice talking to that microservice is where things tend to break down. Did I communicate this correctly? What was sent? What was received? Where did it break down? What was the latency? And if you were doing things in the old way back when you were standing it up with, say, Ansible, or Puppet, or something like that, and you were orchestrating all of these cloud virtual machines, you had to really work hard to instrument the tracing and logging and everything involved in order to track what was going on. Whereas that's one of the magic things about Kubernetes is with a few of the add-ons or some of the things out of the box with Kubernetes, it's a couple of clicks to get so, so much of the data and have insight into where things are going and what's going wrong. And so, I 100% agree with that. Kubernetes is generating a tremendous amount of data. And if you're a data company, it's really nice to have all that come in, and it helps them make money, helps the user of Kubernetes in that situation understand where problems are happening and breaking down. Yeah, there's definitely some network effects of what Kubernetes is doing in that. I completely agree. JOE: I think there are also some interesting companies, like, where they make...Emissary, Ambassador, and they have that sort of dual -- KENDALL: Komodor, is that -- JOE: Yeah, maybe. They have open source, but then they have a product. KENDALL: You're thinking of Ambassador Labs. JOE: Yeah. Ambassador Labs, yeah. I guess I don't really know how much money they're making. But I think that's a really interesting concept as people who make open-source things then make a well-supported product built around it. KENDALL: Sure. What's interesting is, I think in the VC world, at least right now, and it may pick up again, but post-Silicon Valley Bank nearly caving in, I think that the VC tolerance for, yeah, just go get a billion open-source adopters, and we'll figure out how to monetize later I think that the tolerance for that is a lot lower than it was even six months ago. JOE: Yeah, I think you have to have a dual model right from the beginning now. KENDALL: Yeah. Agreed. VICTORIA: You got to figure out how to make money on Kubernetes before you can. [laughs] KENDALL: You know, minor detail. That's why I think services companies in this space still have a lot going for it. Because in order to even be able to sell software to a company using Kubernetes, you half the time have to go stand up Kubernetes for them because it is still that hard for so many people to really adopt it. VICTORIA: Yeah. And maybe, like, talking more about, like, when it is the right decision to start on Kubernetes because I think the question I get sometimes is just, is it overkill? Is it too much for what we're building? Especially, like, if you're building a brand-new product, you're not even sure if it's going to get adopted that widely. KENDALL: I mean, and I'm [laughs] curious your thought on this, Joe, but there's a good argument to be made that Heroku was enough for the vast majority of founders early on. But the thing is, Kubernetes isn't as hard as it used to be. Going and clicking a couple of buttons on GKE and deploying something into Kubernetes with GKE Autopilot running it's not as easy as Heroku, but it's not wildly far off. And it does substantially future-proof you. So, when is it too early? I'm not sure it's ever too early if you have an intention of scaling if you're planning on running some kind of legacy workload, like, things that are going to be stateful. Or maybe WordPress, for example, you don't probably need to deploy your WordPress blog onto Kubernetes. You can do that in your cPanel on Bluehost. I don't actually know if Bluehost even exists anymore, but I assume it's still a thing. I don't know, what would you say, Joe? JOE: I agree with that. I think it's a hard first pill to swallow. But I think the reality is that it's very easy to underestimate the infrastructure needs of even an early product. Like, it doesn't really matter what you're building. You're still going to have things like secrets management. You're still going to have to worry about networking. They just don't go away. There's no way you have a product without them. And so, rather than slowly solving all those problems from scratch on a platform that isn't designed for it, I think it's easier to just bite the bullet and use one of the managed solutions, especially, as you said, I think it's getting easier and easier. The activation energy from going from credit card to Kubernetes cluster is just getting lower. KENDALL: And so, the role of the CTO is just getting easier and easier because they can just adopt the one technology, and it's obviously Kubernetes. And it's obviously Rust, right? [laughter] Yeah, no, I'm with you. And I think if you find somebody who knows Kubernetes inside and out, it's really not going to take them long to get started. VICTORIA: Yeah, once again, change management is the biggest challenge for any new innovation coming into adoption. So, I'm curious to talk more about the influence that you need and how you influence others to come around to these types of ideas, like, in the executive suite and with the leadership of a company, especially on these types of topics, which can feel maybe a little abstract for people. KENDALL: How you influence them specifically to use Kubernetes, or just how you talk with them about technology adoption in general? Or what are you asking? VICTORIA: Yeah, like, how do I get people to not just turn their ears off when I say the word Kubernetes? [laughs] KENDALL: Yeah, I mean, I think...so I think that's where it's the technologist's job and the role of the CTO to translate these things into business speak. And that's why I'm using words like future-proofing your infrastructure is because there are companies that...I know one company that made a conscious decision that they were going to try to re-platform every single year, and that is not a good idea or sustainable for the vast majority [laughs] of companies. In fact, I can't think of a single situation where that makes sense. But if you can say to the CFO, "Hey, it's going to cost us a little bit more right now. It's going to save us substantially in the long term because this is the thing that's winning. And if we go standardize on Heroku right now, every company does eventually have to migrate off of Heroku. They either go out of business, or they get too big for it." That's the kind of thing that needs to be communicated in order to get people to adopt it. They don't care what the word is. They don't care if you're saying Kubernetes; you know, most CFOs understand it about as well as my mom does. My mom tries to bring it up in conversation because she's heard me use it. And she thinks it makes her sound smart, which maybe it does in the right climate. VICTORIA: My partner does the same thing. He says DevOps and Kubernetes all the time. I'm like; you don't know what you're talking about. [laughter] JOE: Those words do not come up in my house. KENDALL: One of my kids asked me to explain Kubernetes. And I do a whole talk, particularly at organizations where understanding Kubernetes is essential to the salespeople's role. And I give a whole talk about the background of how we got here from deploying on some servers in our back room. And, you know, what's different about the cloud, what containerization did, et cetera. And I have this long explanation. And I remember taking a deep breath and saying to my kids, "Do you really want to hear this?" And I had one son say, "Yes, absolutely." And my wife and three of the other kids all stood up and said, "No way," and left the room. So, when somebody asks me, "What do you do?" Actually, one of the key relationships I built with some of the early people at GCP when we were partnering closely with them was a person that I met, and I asked, "What do you do for a living?" And he said, "I can tell you, but it's not going to mean anything to you." And I was like, "That's what I say to people." And it turned out he was in charge of, you know, Kubernetes partnerships for Google. I can explain to you what it means and why it's important. But you're not going to be happy that I spent that time explaining it to you. VICTORIA: [laughs] That sounds awesome, though. It sounds like you built a server rack just to demo to your children what it was. KENDALL: No, no. I just talked back through the history of...that company that I mentioned that built Twitter about five years too early; we had a, you know, we had a server rack in the...literally physically in our closet that was serving up our product at the time. VICTORIA: Probably the best demo I ever saw was at Google headquarters in Herndon, and someone had built...They had 3D-printed a little mini server rack that they had put Raspberry Pis onto, and then they had Kubernetes deployed on it. And they did an automatic failover of a node to just demo how it works and had little lights that went with it. It was pretty fun. So maybe you should get one for yourself. [laughter] It's a fun project. KENDALL: They remember the things that it enables. They don't remember what it does. And so, when I say so, and so is a client that's using this technology, then they get real excited because they're like, "My dad makes that work." And I'm like, well, okay, that's kind of a stretch, but you get the idea. VICTORIA: Yeah, you got to lean into that kind of reputation in your house. KENDALL: That's right. VICTORIA: And you're like, yes, that's correct. KENDALL: That's right. [laughs] VICTORIA: I do make Kubernetes. I make all the clouds work, yeah. KENDALL: Actually, my most common explanation is Kubernetes is the plumbing of the internet. Unless you're a plumber, you don't care about the pipes. You just want your shit to flush when you use the toilet. You want the things to load when you click your buttons. You don't actually care what's going on behind the scenes, but this is what's orchestrating it increasingly across the internet. VICTORIA: So far, we've called Kubernetes WordPress or the toilet. [laughs] KENDALL: The plumbing. [laughter] VICTORIA: You are really good at selling it. [laughter] KENDALL: Hey, if you want to build a nice, clean city, you need good plumbing. You might not care what the pipes are made of, but you need good plumbing. [laughs] VICTORIA: Works for me. On that note -- [laughs] KENDALL: Yeah. Right? Right? VICTORIA: That's [inaudible 36:41] on a high note. Is there anything else that you'd like to promote? KENDALL: With regards to CTO Lunches, we have a free listserv. There are local lunches. If there isn't a local lunch where you are, it's very lightweight to start up a chapter. We often have folks who are willing to sponsor that first lunch to get you going. We do have a paid tier of CTO Lunches. If you want a small back room Slack channel of people to discuss, I think it's $99 a month. Yeah, if you're a CTO and/or a senior engineering leader and you want a community of people to process with, be it our free tier or our paid tier, we've got something for you. We're trying to invest in this to build community around it. And it's something we enjoy doing more than almost anything. Come take part. VICTORIA: You can subscribe to the show and find notes along with a complete transcript for this episode at giantrobots.fm. If you have questions or comments, email us at hosts@giantrobots.fm. And you can find me on Twitter @victori_ousg. This podcast is brought to you by thoughtbot and produced and edited by Mandy Moore. Thanks for listening. See you next time. ANNOUNCER: This podcast is brought to you by thoughtbot, your expert strategy, design, development, and product management partner. We bring digital products from idea to success and teach you how because we care. Learn more at thoughtbot.com.Special Guest: Kendall Miller.Sponsored By:thoughtbot: Are you an entrepreneur or start-up founder looking to gain confidence in the way forward for your idea? At thoughtbot, we know you’re tight on time and investment, which is why we’ve created targeted 1-hour remote workshops to help you develop a concrete plan for your product’s next steps. Over four interactive sessions, we work with you on research, product design sprint, critical path, and presentation prep so that you and your team are better equipped with the skills and knowledge for success. Find out how we can help you move the needle at: tbot.io/entrepreneursSupport Giant Robots Smashing Into Other Giant Robots

Alaina Percival is the Co-Founder and CEO of Women Who Code, with a mission to empower diverse women to excel in technology careers. Alaina delves into the origin and mission of Women Who Code, highlighting its community building, free technical events, and collaboration with companies to promote diversity in hiring. Victoria adds her personal experience with the organization, emphasizing its positive impact on her career. They discuss the challenges faced while expanding Women Who Code, including the need for systems and processes to manage growth. Alaina recounts stories of discrimination faced by women in tech and stresses the need for continued support and encouragement. The conversation also touches on the financial benefits of diversity and the alignment of Valor Ventures with Women Who Code's values. This discussion offers a detailed look into the women in tech movement, the importance of community, and the drive to create a more equitable industry. It serves as a reflection on both the strides made in fostering diversity and the work still needed to create a truly inclusive technology field. __ Women Who Code Join the Women Who Code Slack! Women Who Code Podcast Follow Women Who Code on Facebook, LinkedIn, Instagram, GitHub, Twitter, or YouTube Follow Alaina Percival on LinkedIn or Twitter. Follow thoughtbot on Twitter or LinkedIn. Become a Sponsor of Giant Robots! Transcript: WILL: This is the Giant Robots Smashing Into Other Giant Robots Podcast, where we explore the design, development, and business of great products. I'm your host, Will Larry. VICTORIA: And I'm your other host, Victoria Guido. And with me today is Alaina Percival, Venture Partner at Valor Ventures and Co-Founder and CEO of Women Who Code, with a mission to empower diverse women to excel in technology careers. Alaina, thank you for joining us. ALAINA: Thank you so much for having me. I'm thrilled to be here. VICTORIA: I'm thrilled to have you as well. I reached out. As you know, I was previously a Director of Women Who Code D.C. and helped to organize our DevOps and cloud series when I lived there. And it really had a huge impact on my career. So, I'm just super psyched to talk to you today. What's going on in your world, Alaina? ALAINA: So, in addition to my full-time job of working with Women Who Code, I'm also a mom of two young children, and so they're currently three and five. And so, it's summer. We've got summer camp. Every week is a different program with different details and things that you have to read and stay up on. It's a lot of additional project management added on over the summer. I'm looking forward to getting back to the school year, where I can kind of focus on just one role. WILL: That's amazing. And I can totally relate because I have a four, a three, and a one-year-old. Yes, it's a different story when you have to, like you said, project manage around them. So, that's amazing that you're wearing so many hats, and you're doing that. Hats off to you. ALAINA: Same to you. [laughter] WILL: Victoria, what about you? What's going on in your world? VICTORIA: Well, it is summertime at the beach, so all the kids are out. [laughs] It's busy. But that means that you know, the weather is warming up. It's tempting to try to go surfing again, so we'll see if that ends up happening anytime soon. But no, I'm hanging out. I'm local. I'm kind of done traveling for a little bit, so not until I go out to Outer Banks to visit my baby niece and nephew in August. So that's where I'm at right now. I'm kind of hunkered in trying to survive without air conditioning here and get through the summer. [laughs] WILL: You don't have AC? VICTORIA: I do not. Yeah, there's a lot of houses around here just never were built with it. I have heat, but I have no air conditioning. ALAINA: Are you being hit with the heat wave that's happening? VICTORIA: Yes. But it's still very mild. We're spoiled here for sure on weather. WILL: [laughs] VICTORIA: It's like 77, and I'm like, ugh, it's so hot. [laughs] WILL: I'm in Florida, and it amazes me. So, I got up early, around 7:00 o'clock, to go out for a run, and it's, like, 87 degrees. And it feels like almost 100 at 7:00 a.m. And I'm like -- VICTORIA: Oof. WILL: How? [laughs] Like, the sun is barely out, and it's already reaching 100. So yeah. ALAINA: I feel you. I'm in Atlanta. Yesterday, I had an in-person meeting. Typically, we're entirely remote. So, I was wearing real pants [laughs], and it was a hard day. We're not quite as hot as Florida. We are in the low 90s. But yeah, this weather is for real. WILL: Yes. [laughter] VICTORIA: That is the...yeah, working in person again in a hot climate. [laughs] I forgot the challenges of that of, like, trying to navigate life while having to be fully clothed is difficult in that kind of weather. So, I'm glad. I hope you all find some ways to stay cool and to entertain your children [laughs] so that you have some sanity and can get through the summer. I've also been really interested in the European model of just taking five weeks off in the summer. Doesn't that sound nice? WILL: Yes. [laughs] ALAINA: Yeah. I started my career off in Germany. I worked for Puma. Their headquarters is right outside of Nuremberg in a town called Herzogenaurach. And people really do take the whole month off August. And, in fact, you would even separate out the salaries. So, you got something called urlaubsgeld, which was vacation money. So, you would get kind of a little bonus going into August, and then everybody would take off. So, I agree with you. We should be doing that. VICTORIA: Yeah, we should be doing that. And I'm so excited. Maybe we can segue into, like, your background and how you got started. How did you go from there to founding Women Who Code? ALAINA: Yeah, so after working at Puma, I somewhat came back to the United States. I did a dual degree program, an MBA where I was studying between Atlanta, so I could get back in the United States, spend some time with my family, and then also the Sorbonne in Paris. And I did an MBA and a degree in organizational management, Master's in organizational management. Then I went to work for really small ones, performance wear company. And that was more, like, a startup because you really had to think outside of the box. You know, you're a small $10 million a year company, and Nike and Mizuno, you know, these big companies are your competitors. So, I had the opportunity to move out to San Francisco. It was one of the cities that was always on my list of, hey, if you get a chance to do it, go for it. And I did. So, I moved out there, and I kind of hit a bit of a wall with my career, an unexpected wall because up until that point, I had just this really, you know, successful early career. I got out there, and they're, like, Puma. You know, you haven't worked for Microsoft, or Twitter, or Facebook, or Google. Who are you? So, I started learning to code just to transition my skill set to help me understand the culture and the language and just getting more involved in the tech community. And I was still struggling a little bit in figuring out my transition pathway and got more and more involved with Women Who Code and started, you know, spending my nights and weekends. And finally, I was at a small startup that had gotten acquired, so I had my official tech credibility. And I went to work for one of the top technical recruiting firms, executive recruiting firms in the Bay Area, as their head of developer outreach. And I largely chose that role because they were allowing me to run their philanthropic arm, and I focused that around supporting underrepresented communities, you know, get a leg up in the tech community. And then, while I was there, I was working with CTOs, vice presidents of engineering, directors of engineering on a day-to-day basis. And I started learning what they were doing in their career to help develop and cultivate the success that they were having, and I started bringing that knowledge and programming into Women Who Code. And that's where our mission around seeing diverse women excel in technology careers came about is, you know, that piece of retaining and seeing diverse women excelling was an area that wasn't really the focus at the time. And I feel like it sounds funny now because it's such a big piece of conversation. But that was the beginning. VICTORIA: Yeah, it's so interesting that your experience from being in a startup and then how you moved up into being really involved in the hiring and the process of how women...how anyone would actually, like, move up in their career led you to have that background to found Women Who Code. And for people who maybe don't know, [laughs] no, I certainly know what it is. Can you talk a little bit more about what it offers to women and what it offers to companies who are looking to hire diverse women? ALAINA: For individuals, we are the largest and most active community of diverse technologists. We have close to 350,000 members. We're serving members across 147 countries. And we're producing close to 2,000 free technical events every single year, so that's about an average of 5 per day. Once those events take place, if you happen to miss them if you happen to not be in a location where they're having them in person, we're putting a lot of that on our YouTube channel. So, you can go back when you have time, when you're available, still invest in yourself and learn some of these technical and career-related skills. You can also, you know, when you think about, say, the 2,000 talks that are being delivered at Women Who Code, the majority of them are being led by and delivered by diverse technologists. So, we're creating role models and helping people who are on their career path have a sense of belonging, see a pathway to success. People who are thinking about the career path see themselves represented as thought leaders, as leaders in the tech industry. And that sense of belonging, that sense of drive, is just so important to be able to continue on in your career. But we work with companies. So, Women Who Code is dedicated to accessibility. All of our programming is free or scholarship accessible. And so, what we do is we work with companies, and we do this for two reasons: for programmatic reasons. Because we know that if companies develop strong diversity, equity, and inclusion, and belonging practices, that we will reach our mission and vision so much faster than if we work with every individual in the world. But it also creates an opportunity for us to be able to support the community. So, we work with companies to sponsor Women Who Code to donate to support Women Who Code's programming. We have our first-ever walk coming up, so a walk, run, roll called Women Who Code to the Finish Line. And we're going to be having that in September of this year. And that's going to be an opportunity for the stakeholders. You know, often, people who aren't in our community but absolutely support us say, "How can we help?" And so, companies can form teams and go and walk, run, roll to change the face of the tech industry. Right now, we're also in a position where the tech industry has been doing a lot of layoffs, so there's a lot of instability. And so, when that happens, our programming thrives. So, people are coming to our events in high numbers. People are participating in our programming. People are visiting our job board. It's the time when companies are stepping back and pulling back on their funding and things like that. So, I just encourage every single company to...if you have a great technical job open, make sure you're sharing it with the Women Who Code community because we have incredible technologists. They deserve access to companies that are willing to support them and the best roles that are available in the industry today. WILL: Alaina, I just want to honestly and truly say this, what you're doing is amazing. Having a background in nonprofit, over 140 companies, over 300,000 in your membership, and it's an international nonprofit. It's truly amazing what you're doing and helping women find their role and help them become better. I'm truly just blown away by, you know, you started in September 2011, so you're coming up on 12 years this year. And just 12 years as a nonprofit and doing this, share with us how was it received at the very beginning? Because I feel like that was a different time that we're in right now. ALAINA: Yeah, it started off as a meetup, just a community group in San Francisco. And it was incredible. It felt like our little secret. And we were spending time together. We were learning. We were building connections. And just it was this incredible community. And then, the world started talking about, hey, we need to teach girls to code. We need to teach women to code. And we were this community of people in the industry. Our average age at Women Who Code is 30, so 50% of our members are currently in technical roles. So, we had this moment of, hey, we need to elevate the voice of those who are in the industry right now, alongside teaching girls to code and teaching women to code. Because if you miss out on that, it actually becomes a threat to the women in the industry who, every time you hear "Teach women to code," you're saying she doesn't already know how to do it. And we had so many people in our community who already did and already had to kind of prove themselves on a regular basis or constantly underestimated. In the early years, a Women Who Code leader who told me that she was managing a booth at a conference, and everyone was an engineer except for one recruiter, and the recruiter's name was Brian. Someone walked up to her and said, "Are you Brian?" Because it was easier to imagine that her name was Brian than that she was one of the engineers at the table. And so, kind of going through this, we said, hey, we need to elevate our voices. We need to elevate the needs of women in the industry. And it feels being in it day by day, that nothing's happening. But when you look back over 13-15 years, you see that parental leave policies have improved significantly, that we see numbers in leadership going up across the board, that it's part of the conversation that relatively standard and tech companies to have DEI roles within the organization, within the people team. And so, these are not enough. It's just the beginning. But it is a lot that's taken place over the past 10 to 15 years. VICTORIA: I agree. And I can relate as someone who was a project manager working in a technology space. Was it back in, like, 2013 or something? And you'd go to tech meetups, and most likely, I would be the only woman there. [laughs] But then, with Women Who Code, my friend invited me to go to a Ruby event, and it was, you know, all women. [laughs]. There was a woman who was even giving the instruction. And so, that was just a really cool feeling after having been out networking and feeling kind of isolated to really find a lot of people who are similar to you. And I remember part of the narrative at that time when we were talking about increasing inclusion and diversity in technology; there was a narrative that, well, there just aren't as many women in tech. And being a part of Women Who Code, I could be able to, like, answer back to say, "Well, there actually is a lot of women in tech." And it's the bigger problem that women would get started because they're interested in the industry and having good careers, but then they would fall out midway. So, there just wasn't enough progression in their careers. There wasn't enough support on the parental leave side, or there just wasn't enough community to keep people interested, like, when you're the only one. And many of our members they were the only women in their company, and then Women Who Code was where they found people they could really connect with. So, I just think it's interesting that it solves a particular problem where we would have women who are just interested in learning to code who would come to our events. And then, we had women who were actively coding in their jobs and teaching others in these leadership roles within the community to advance their own careers. And that's certainly what I did, and how I broke into executive leadership was, like, I'm a director at Women Who Code and I've got all this other leadership experience. And I'm bringing that network with me. It really increases your value to employers and demonstrates your leadership abilities. ALAINA: Yeah, I couldn't agree more. The program which we kind of fell into, it's our volunteers, is our program that I'm actually most proud of at Women Who Code. And it's probably because I get to know our volunteers because I know so many people's lives and careers are impacted by our programming. But that leadership development, that practice-based leadership that our volunteers are able to obtain, the doors that get open, and just like you said, it opened doors. And I remember it hit me when one of our volunteers told me she was interviewing with SpaceX. And one of the reasons they said they were excited to talk to her was because of her Women Who Code leadership experience. And I just thought to myself, we're doing something right. [laughs] VICTORIA: Yeah, absolutely. And I think maybe part of Will's question before, too, is, like, did it always feel like you were doing something right? Or did it all just come together naturally? Or what kind of bumps did you initially hit when you were getting things off the ground? ALAINA: Yeah. When we first got started and realized, hey, we need to make Women Who Code more accessible, we were doing everything in a very manual way. We needed to adapt to building systems and processes, and that's not the fun part of running a volunteer organization. And when you're moving so fast, it means slowing things down a little bit to be able to make sure that you can do things better, more consistently, more efficiently, but it's so critical. And so, I would say we kind of launched outside of the Bay Area in a couple of cities. And it just snowballed until we expanded into 20 to 40 more cities within probably a year outside of that. And we just really needed to catch up on creating systems and processes, which is not beautiful at all, but it's an important part of running a real business, a real company. WILL: That's amazing. First off, I just want to say I am so sorry that the world we live in looks down upon women or anybody. So, I'm just so sorry that, like, the story you said about Brian, asking the lady that. I feel like that's so disrespectful. I am so sorry if you ever got treated that way or anything like that. And so, I was going to ask this question, and then I kind of answered it. But the question was, do you think women are at a place to where kind of equal in tech? And I kind of answered my own question and said, "No." And so, I want to reframe it. What do you think it will take to continue to help the women get to that level of where it should be? ALAINA: It's going to take a lot of things. But the fastest and easiest way to create more equality for women and girls in the tech industry is by investing and supporting the incredible talent that is in the industry today. We need them to thrive. We need them to stay in their careers. We need them to become leaders with power and influence to create more equity in the industry so that when future generations are coming in, they're coming into an industry that is less broken for them, that is more welcoming, that shows and demonstrates more opportunity. This is one of the most exciting and innovative industries to be a part of. So many things are being shaped and built for the first time that are systems that are going to be the foundations for years or centuries to come. And so, it's more important now than ever for us to be thinking about bringing equity into that so we're not dealing with technical debt, where we're starting from a system that has more equality to it. VICTORIA: I really appreciate that perspective. And I'm curious how that relates to your work at Valor Ventures as well. ALAINA: Valor Ventures is very aligned with the values of Women Who Code, which is why I chose it. I am passionate about creating more equality and opportunity for diverse individuals to thrive and succeed in general but via the tech industry. And so, when I move into focusing on entrepreneurs and focusing on seeing diverse entrepreneurs succeed in building thriving organizations, I see an opportunity to have someone who will be thinking earlier about the policies and the practices that are going to build more equitable teams, products that are really for all of their users. VICTORIA: I think that's a great mindset. And it reminds me that when we talked about, like, the importance of diversity, and equity, and inclusion, that it's not purely a moral thing, even though morally we know we want to support and be inclusive, but that it's also good business strategy [laughs], just by the value of having different perspectives and different types of people, and then being able to have your products be accessible for a diverse group as well, right? ALAINA: Yeah, the data shows teams that are diverse are smarter. Companies that have women represented in leadership they have a stronger ROI. There's business reason behind it. There's certainly a social-moral reason that it just should take place. But, you know, if you need to come back to your shareholders or your investors, there's financial data around it. WILL: Yeah, I totally agree on all that, like, yes, yes, yes, yes, yes. MID-ROLL AD: Now that you have funding, it's time to design, build, and ship the most impactful MVP that wows customers now and can scale in the future. thoughtbot Liftoff brings you the most reliable cross-functional team of product experts to mitigate risk and set you up for long-term success. As your trusted, experienced technical partner, we'll help launch your new product and guide you into a future-forward business that takes advantage of today's new technologies and agile best practices. Make the right decisions for tomorrow today. Get in touch at thoughtbot.com/liftoff. WILL: What have you seen hold back women in this space? And the reason I'm asking this question is because there are some biases out there, and, at times, we don't even realize it. For example, I know we have parental leave. And before I had kids, I didn't understand parental leave at all. But then, now that I have kids, I'm like, oh, it is not even close to being enough time during that time, you know, four or five hours of sleep at night, just all those things. So, in your experience, what have you seen? And hopefully, we can use this as a learning opportunity for anybody that just may be blind to it. What have you seen that kind of holds it back? ALAINA: That's holding back, like, implementing specific policies and practices or? WILL: Yes, holding back the policies, or maybe women not being as prevalent in tech roles any of those areas. ALAINA: So, sort of two different approaches with that is I'm optimistic. I think most companies, yes, they care about the bottom line, but they want to be doing the right thing if it's easy. Leaders like me we need to put pressure on companies making better decisions. But also, industry leaders and organizations out there need to be able to make it easier for companies to make the decisions that are going to create more equity inside of their organization. I know that's taking the responsibility off of them a little bit. But companies won't make commitments. They won't do the hard things if they don't know how to do it. And so, the easier that we can make it for them to make the right decision, the more likely they are to make the right decision. VICTORIA: I think that people want to do the right thing if it's easy is a really succinct way to explain a lot of, like, social and moral [laughs] issues right now, right? Most people generally want to do the right thing, but it can be complex. I'm curious about, speaking of complexity, for Women Who Code, going through, you know, being an organization that was built around in-person events, and then having COVID happen, so, like, what were some of the challenges of the last few years and changes that you experienced along the way? ALAINA: Yeah, when COVID hit, that was a big moment for the whole world. It was certainly really hard for organizations that rely on in-person activities. You know, our major conference supplied a third of our operating revenue. Our members were going to, you know, close to 2,000 in-person events. And so, we had to adapt just like everyone else. The organizations and the companies that adapted were the ones that thrived. So, we had to completely retrain all of our volunteers from doing in-person events to be able to create digital events for our community. We had to figure out how to produce major events, and conferences, and hackathons and do it in a remote way. And then, of course, there's the day-to-day that absolutely everyone had, and that was, you know, just your team went from meeting in person to everyone being remote. And some of the great things that came out about that is we were serving members in about 26 countries and about 80 cities, and now we serve members in 147 countries. It just made it accessible that if you don't happen to be in a location where an event is happening and you also don't happen to have childcare, be able to participate, that you are still able to participate in an online setting. And then, what we saw with being able to start moving more of, you know, those talks that were being delivered to our YouTube channel, it then became even more accessible. People spent about five years of life watching our YouTube trainings, and that's time people are investing in themselves. And when I say they did it, and I'm talking about in 2022. So, our YouTube channel, our trainings, they continue to grow, and then our online events continue to happen. But luckily, now we are able to start going back in person. And it's, again, just so amazing to be able to see the people you haven't seen in a long time, feel that feeling that is just a little bit different for an in-person event. WILL: That's amazing. So, from, say, 2019, 2020 to now, it went from 80 countries to over 140, just because of the pivot to go more, like, YouTube and tech. Is that kind of what you're saying about the growth of it? ALAINA: Yeah, so about 80 cities, so about 25 countries to serving members in 147 countries. WILL: That's amazing. ALAINA: Yeah, a tremendous amount of growth and creating accessibility around the globe. Previously, we were really only able to focus on tech hubs that had an ecosystem to support it. But, you know, just because you're from a rural area of your state or from a country in the Global South, you still deserve access to this incredible community and all of the free accessible programming that Women Who Code has to offer. When we have a conference, we have people from 88 countries participating. And when you sign into the networking session, you're going to hop on the phone with someone from Nigeria, someone from Bangladesh, someone from your same city, and it's just such an incredible experience to be able to have that global focus and reach. WILL: Wow, that is so amazing. So, let's talk about right now. What does your next milestone look like, you know, in the next six months or next year? What does that look like for you? ALAINA: As I mentioned before, one of the big challenges we've had this year is our programming is going so, so well, but our funding has pulled back a little bit. And so, we're working to diversify our revenue strategy a little bit and have a traditional nonprofit walk that we've never done before. And it's a remote walk, so anyone all over the world can participate just like you can with our digital events. But this has been something new for us. Because when we went through it during COVID, again, you know, you'd get on the call with all of your partners. You know, the world is going through something, and you kind of say, oh yeah, we're in it together. But you don't see the grace that you saw in 2020 and sort of the camaraderie, and we're in this together, and we're going to give you space and support you, you know, in every way that we can that, you know, is just really missing this time around. You know, we have members who absolutely need support in their careers right now. And so, it's navigating through something different. VICTORIA: Yeah. And I guess talking more about inclusivity, like, we have all this free content, and it is Women Who Code. But I remember when I was an organizer, I had a few people ask me, "Well if I'm a man, can I come to your event?" And I was like, "Yes, it's open to everyone," right? Like, it's promoting women, and it's about women growing in their careers. And certainly, if that's not also your intention with attending the event, you should keep that in mind and make sure you're leaving space for other people. But I also really appreciated that it's open for everyone and that it's open for everyone who is in the women umbrella, and being intentional about that, and that it's inclusive of everyone who relates to being a woman, right? ALAINA: Yeah. Women Who Code welcomes all genders. We, you know, really struggle with our name from a brand perspective because it isn't as inclusive as we'd like it to be. So, actually, after we say our name, we try not to repeat the word women anywhere else. From the beginning, been dedicated to having an open, accessible community. But we definitely require, you know, that you are following our code of conduct, that you're there for the intended purpose of the event. And we want to make sure that we're protecting our community. VICTORIA: Well, I really appreciate that. And I appreciate...it sounds like a value organization that I'm with. I always look for those things that that's what we're really promoting. There's been so many changes that have happened with Women Who Code and in your career. If you could go back in time and give yourself some advice when you were first getting started, what would you tell yourself? ALAINA: If I was going back and thinking about what I would tell myself in the beginning, I'd probably tell myself to focus on data sooner. Coming from the history of being a meetup group to transitioning to being a global nonprofit, we dragged our feet around focusing on data impact, and really, it's because we're constantly doing so much programming. We're always doing so many things, and anything you add on is an extra thing to do. And so, I would say focus on the data much sooner. VICTORIA: I can speak to there being a lot of events. I remember back in the heyday in D.C., it was, like, algorithms on Tuesdays and Ruby on Thursdays, and then next week, it would be DevOps. And there was just always something going on. And I thought that was so cool. And I really appreciate just really everyone who is involved in putting on those programs. I really want to emphasize, too, like, the value for companies working with Women Who Code. And what do they get out of the partnership, and how can they really engage with the community? ALAINA: Yeah. So, companies that work with us, it's a partnership. They are there to support the community, and that's what they have to do to really develop trust. And we're going to make sure that we're guiding them in that process. So, if we see an opportunity for them to engage in a more authentic way, we're going to point that out. But companies are often hiring from our community; that's one of the big reasons, not just through our job board because our members are unicorns. They're diverse technologists, and everyone wants to hire them. And so, you can just say, "Hey, come work for me." But really, they want you to explain who's on the team? What are the exciting projects, and what are the exciting technologies that your company is building? So that they can actually identify that your company is an organization that they would want to work for before just applying for a job. And that's what a lot of our partnership creates space for. So, maybe getting an opportunity to join our podcast and tell the story and get to know some of the diverse leadership team or diverse engineering team, learn about some of your, like, commitment to DEI and things like that. Because when a senior engineer receives multiple job outreaches, they're going to respond to the one that they've heard of, that they already know is a good company, that they know is supporting and investing in building equity into the tech ecosystem. That's going to go a long way in them deciding to reply. WILL: That's awesome. Earlier, you mentioned being inclusive of all the members. I think I know the answer, but I just want to double-check. If I want to volunteer, am I able to volunteer at Women Who Code? ALAINA: Yes, absolutely. If you visit our website...and we just updated our website, so I encourage everyone to go visit womenwhocode.com today. It's looking different than it has over the past five years. There's a sign-up to volunteer. You would be absolutely welcome, Will. WILL: Awesome. And, as a volunteer, what would that look like? What could I get involved in? What areas? ALAINA: You could decide to be a speaker. You could apply to be a network leader. You could become a lead in a particular technology area. We have six technical tracks. Our tracks are cloud, data science, Python, mobile. When [inaudible 32:53] hears about it, we will have emerging technologies track that was expanded from our blockchain community this year. And then, we also have a career track as well. So, you can become a lead focused on one of those particular areas in our digital communities. You can get engaged with the Women Who Code community in many different ways. We also have some really cool programs like mentor me and buddy system, so getting involved in those. Building long-form connections or long-time connections with individuals in the community really helps to create a sense of belonging and start to build trust and an opportunity to exchange knowledge. VICTORIA: I always really appreciated people who were, like, "Do you need a space to host your meetup?" Or "Do you want us to buy you pizza for your meetup?" [laughs] Those are very easy ways to engage. And it's true that the membership does see and pay attention to, like, who is regularly getting involved in committing to this, and it makes a difference in your brand and reputation. ALAINA: Absolutely. The companies that work with us absolutely hire from the Women Who Code community. I'll give two examples. So, one of the most exciting examples was we had an event at a company, and they sort of were connecting in an authentic way, not, like, an interview way, but they essentially were doing an early interview with people who were there. And so I remember that it took place on Tuesday, and they had a job offer on Friday at the company that they were at. So, they were just able to move so quickly and hire someone from our community. And then, ages ago, Snapchat was at our first-ever conference, and they had hired four or six people at that event. And it was just so cool to see that we're not a recruiting agency, so we really just rely on either individuals or companies to tell us when they have these amazing career outcomes. So, every time we hear about it, it's always exciting to me. VICTORIA: That's super cool. And I wonder, what is the thing you're most excited about coming up for Women Who Code this year? ALAINA: We have CONNECT Asia taking place later on this year, and so that's our major technical conference with a focus in the Asia market. It's going to be just really, really exciting. We haven't had one since pre-COVID. It's still going to be a remote event. We had CONNECT LATAM, so our first-ever conference focused on Latin America last year. And this year, it's focused on Asia. So, it's really exciting to get back and provide some support to our regional audiences and really showcase some of the incredible talent and leadership coming out of those regions. WILL: That's amazing. So, the question I have for you, and it's easy to assume this question, but I want to hear from you because I know you talked about, at the beginning, how it was when you started the nonprofit. But what is the wind in your sails? Like, what keeps you motivated and going? It sounds like it's an easy answer, but just from your heart, what motivates you? ALAINA: Oh, it is absolutely the stories that I hear, like I said, especially from our volunteers. So, the Mexico City volunteer who, in under a year, told me her salary increased 200%. The director from Toronto, you know, when she stepped up, was an individual contributor, and under one year, she made it to director level, and today she's a vice president. So, when I think of the career impacts that are taking place for our members, and every single time I hear about it, it drives me to wake up. It drives me to work harder. It drives me to deliver better program and just makes me completely connected to what we do as an organization. VICTORIA: What a great benefit. And for myself, personally, it absolutely has been a factor in the last, like, two jobs I've gotten. [laughs] They're like, "Oh, you are a director at Women Who Code? That's so interesting." So, I really appreciate everything that you've done and happy to be a part of that. And my personal network, I know many women who have been through that and benefited immensely from having that networking community. And really, even just being able to see yourself and know that you belong in the industry, I think, is really, really important. ALAINA: I'm sure I'm going to be telling your story the next time someone asks me. [laughter] VICTORIA: That's great. No, please do. And let's see; we're wrapping up at the end of our time here. Is there anything else that you would like to promote? ALAINA: Yeah, please visit womenwhocode.com. If you have technical jobs available, please post them to the Women Who Code job board. Again, it's just womenwhocode.com/jobs. Join our community. Check out our amazing, new, beautiful website, and follow us on social media @WomenWhoCode. VICTORIA: Love that. Thank you so much for joining us today. You can subscribe to the show and find notes along with a complete transcript for this episode at giantrobots.fm. If you have questions or comments, you can email us at hosts@giantrobots.fm. And you can find me on Twitter @victori_ousg. WILL: And you can find me @will23larry. This podcast is brought to you by thoughtbot and produced and edited by Mandy Moore. Thank you for listening. See you next time. ANNOUNCER: This podcast is brought to you by thoughtbot, your expert strategy, design, development, and product management partner. We bring digital products from idea to success and teach you how because we care. Learn more at thoughtbot.com.Special Guest: Alaina Percival.Sponsored By:thoughtbot: Now that you have funding, it’s time to design, build and ship the most impactful MVP that wows customers now and can scale in the future. thoughtbot Lift Off brings you the most reliable cross-functional team of product experts to mitigate risk and set you up for long-term success. As your trusted, experienced technical partner, we’ll help launch your new product and guide you into a future-forward business that takes advantage of today’s new technologies and agile best practices. Make the right decisions for tomorrow, today. Get in touch at: thoughtbot.com/liftoffSupport Giant Robots Smashing Into Other Giant Robots

Introducing thoughtbot's ongoing maintenance service. Need reliable support and maintenance for your software? Look no further. Our expert team handles upgrades, bug fixes, UI adjustments, and new feature development. And the best part? Our maintenance packages start at just 5k per month for companies of all sizes. From Ruby on Rails to Node, React, and, yes, even PHP, we've got you covered. Trust thoughtbot for top-notch support and optimized performance. To receive a custom quote, contact sales@thoughtbot.com. Marc Mar-Yohana is the CEO and Founder of OtisHealth, a personal health application and platform for patient-caregiver engagement, population health, and clinical research. The conversation revolves around the origin and working principles of OtisHealth, a healthcare app designed to consolidate health information. Marc was motivated to start the app following the tragic death of his eight-year-old daughter, Constance, from an undiagnosed brain tumor. Despite being under the care of multiple health providers, the fragmentation of her medical data meant they missed the signs of her condition. Marc has dedicated his life to developing better tools for families and caregivers to manage their loved one's health. He aimed to create a unified system where all health data could be gathered, enabling caregivers, patients, and medical providers to see the whole picture. OtisHealth allows patients to integrate data from different sources, including wearable devices, and capture information outside clinical settings. The initial outreach strategy of OtisHealth through consumer channels was slow to get traction. The company switched to recruiting through organizations with health interests, such as health insurers or "payers," leading to a significant increase in users. Although not everyone uses the app daily, it is a crucial health management tool for those with chronic illnesses or emergencies. The trustworthiness of OtisHealth is demonstrated through accreditation from the Electronic Healthcare Network Accreditation Commission, indicating that their practices meet or exceed federal regulatory requirements and industry guidelines. This, along with community outreach and educational content, helped build trust with users. Marc's diverse corporate background gave him the skill set to lead OtisHealth, emphasizing the importance of team development and collaboration with other organizations, even competitors, to move the mission forward. __ OtisHealth Follow OtisHealth on Facebook, LinkedIn, Instagram, or YouTube Follow Marc Mar-Yohana on LinkedIn. Follow thoughtbot on Twitter or LinkedIn. Become a Sponsor of Giant Robots! Transcript: VICTORIA: This is the Giant Robots Smashing Into Other Giant Robots Podcast, where we explore the design, development, and business of great products. I'm your host, Victoria Guido. And with me today is Marc Mar-Yohana, CEO and Founder of OtisHealth, a personal health application and a platform for patient-caregiver engagement, population health, and clinical research. Marc, thank you for joining me. MARC: Victoria, I'm honored to be here. Thank you so much for inviting me to join you on this podcast. VICTORIA: You're welcome. I'm excited to have you. So, why don't you just tell me a little bit about what's going on in your world right now? MARC: Well, OtisHealth is keeping me pretty busy. So, I live in Northern California. My team is mostly in California, a little bit in Illinois. And we're busy every day, both supporting our members and working with clients. And so, it's exciting times, especially on our advocacy front. We work with organizations across the country to advocate for patient access to their health records and also for individuals themselves to improve their access to quality healthcare wherever they reside in the United States. The advocacy, the work with our clients, and the work with our members keeps us super busy. Although I do still try to make time to hike in the beautiful scenery out here. I'm new to California. I'm originally from Illinois, so it's great to just be able to get out every once in a while for a hike in the area. VICTORIA: That's wonderful. Have you made it to any redwood forest out there? MARC: Yeah, Muir Woods, which is just north of us, north of the San Francisco Bay Area. Most of the time, we like to walk the coastline. So just north of Santa Cruz is a great state park known as Wilder State Ranch. And they have amazing views of the coastline, wonderful views of birds, as well as occasionally spotting whales, and dolphins, and sea otters along the coast. VICTORIA: That's so cool. I had a friend, actually, who just went up there and went kayaking with the otters, and I'm very jealous. [laughter] It sounds beautiful. MARC: Yeah, that can be fun. Otters are really cute creatures. And they can be aggressive too. There's a concern right now. There's one female otter that likes to grab people's surfboards. And I saw a video of a sea lion jumping on top of a sea kayak to steal a fish from a fisherman. VICTORIA: I think if a sea otter or a sea lion wanted my vessel, a kayak or surfboard, I mean, you can have it. [laughter] You worked this hard. [laughs] MARC: Yeah, they're pretty aggressive. They're more comfortable in the water than we are, so they [laughs] pretty much are in charge in the environment. VICTORIA: That's right. We're in their house, right? So, I'm, like, okay, [laughs] you can have it. That's great. Oh, wonderful. I'm glad you still have time to get outside and enjoy hiking with your family, even though you're a very busy founder [chuckles] and very active advocate for your community. So, why don't you tell me how everything with OtisHealth got started? MARC: So, it started with a tragedy, a horrible tragedy in my life. My daughter, Constance, who was eight years old at the time and had been previously diagnosed with autism, apraxia of speech, and epilepsy, died from an undiagnosed brain tumor. She had great healthcare. She had a neurologist, a pediatrician. She had therapists that saw her five days a week and, of course, her parents watching over her. Yet, we all missed the symptoms, the major illness that claimed her life. And so, because all of her healthcare providers were on different systems, and as parents, we didn't have a system, there wasn't a place to put our observations together. And everyone attributed their observations of her changing condition to other medical concerns. And so, after she passed, I started to spend a couple of years trying to understand what happened. And I realized a big part of it was the information was in front of us. It was just in different people's hands. And when we put it together, we could have seen the whole picture that would have shown that she had a more serious illness. And so I chose a new mission in my life: to abandon my corporate career and move into this role of developing a better set of tools for families and caregivers to manage their loved one's health. And so, our mission today is to work with families, caregivers, and people with chronic illness to give them better tools to manage their everyday health and the health of their loved ones, and thereby also improving lives in the community. VICTORIA: Well, I love that out of the tragedy, you were able to find direction and purpose to solve this major problem, which I can relate to having moved across the country. Your medical records don't come with you. You have to basically kind of start all over, or they have to go get them from your past patients. It's not unified as a system, as you might think that is. [laughs] MARC: That's absolutely right. Our data is spread out across different clinical sources. Just in the time I moved out here to California from Chicago, I saw five different providers just because I wanted to get some tests done. So, I had to go to a few different locations to do a normal battery of tests. And so, I had at least five different health records created just when I moved out here. And they're all in different systems, and they're not even on the same type of application. So, to bring them together, I had to basically download them and put them in files on my desktop computer. With OtisHealth, I'm able to retrieve that data and put it onto one continuous record and watch it. But that's still just our clinical data, meaning data collected in clinical settings. We have more data to share of things that you and I observe as regular people or our families observe. And so, the part that's missing in the record is all the observations in the time that we're not in the physician, in a physician's office, or in the presence of a clinician. We can; with our tools today, such as wearable watches, or blood pressure cuffs that are Bluetooth-connected, we can get a lot more data and share that back into our records so that we have a true baseline, not the once-a-year that I go to see a physician, and they say my blood pressure is high. And the next time I go, it's low. It's because we only have two data points over two years. Where today, with our technology and our capabilities, we can have a baseline of true data continuously throughout the year that will give the physician or care team more insights into how we're doing in terms of our health. VICTORIA: That's so interesting. And it makes a lot of sense to me why someone would want to use this or why doctors would want to use this. And I'm curious, once you had this idea, how did you get that initial traction to get started with OtisHealth? MARC: Initially, it was a little difficult. And this is kind of part of our lessons learned when we started the company. We started advertising on Facebook. This is after we launched the product. So, we launched in 2021. We had the idea that we were going to make this available to a lot of people. We knew a lot of folks that needed it. It was okay to get the first 100 or so people because there were folks that we knew needed the application or folks that were curious about it and wanted to try it. And we started advertising through consumer channels such as Facebook, and LinkedIn, and other magazines to people that we knew had the need for the app. Yet, it was a very slow uptake. And the part of what we learned and we started applying to our marketing or our membership development or recruitment thesis is that the health records are kind of like an umbrella. We don't think about the umbrella or going out to get an umbrella until it's raining, and for most people, it doesn't rain very often. And so, it's not something that people would use every day. In most cases, they use it only when they have an emergency or when they're managing their chronic illness or the chronic illness of a loved one. And so, we eventually changed the way we were recruiting and started recruiting through other organizations, such as clients where we're able to get thousands of users through the client that has members. And then, slowly, over time, teach them the importance of managing their everyday health, and taking their own vitals, and recording that, and they record for themselves and their family. VICTORIA: Right. So, you were able to offer the app for free for daily users because you found another group that was interested in having access to the data and having this app, right? MARC: Yeah. So, anybody today can go to the Apple Store or the Google Play Store and they could download the app for free. And they can use the web version also. And they could share it with friends and family, which I always encourage people to do. So, if you have an emergency contact, invite them to your medical records; at least they have your basic medications, and allergies, and other key information in case of an emergency. What we did in terms of our change of strategy early on is we started going to organizations that also had an interest in improving the health of their population and, in particular, health insurers or what we call in the industry payers. And so, payer organizations could be Medicaid, Medicare, or it could be employee health plan, one of the big health insurance companies like Blue Cross or UnitedHealthcare. They have an interest in people managing their everyday health. And so, one of our clients right now, everyone that enrolls in one of their plans automatically gets enrolled in a version of OtisHealth specifically for their members. And those members could still invite people to join them on the platform, and those people can get on with OtisHealth. But the nice thing is now this payer has a way to both encourage healthier activity or healthier practices for their population and monitor if there's a problem. So, if somebody is missing medications, or not taking their medications on time, or has vitals that are tracking poorly, this gives the payer an opportunity to reach out and ask them if they need help managing their health. VICTORIA: So, how does that dynamic affect how you measure successful engagement on the platform, like, a successful rate of engagement? MARC: So, for us, most people don't use the app every day. Most of us don't even think about our health [laughs] on a daily basis from a standpoint of our medical health or clinical health. Sometimes those of us that exercise regularly think about it in those terms or eating healthy. But we don't think about keeping a record or using an app to maintain our health. And so, for us, an active user is anybody that's logging in at least once a month to update their information. Our really great users are the ones who are using the reminder features to take supplements or take their medications. And so, I would say of the few thousand users that we have—we're approaching 10,000 right now active users—only a small percentage of those, maybe 10%, are actually using it on a daily basis for themselves or their family. And so, for us, a good engagement and good practice is folks setting reminders on at least a weekly basis to take vitals, weigh themselves—something that would help them track their health over time—and if they're taking medications, to set daily reminders for the medications that they take. And so, we currently have far more people enrolled in OtisHealth and that, you know, 5,000, 6000 I mentioned that are active. But they basically bought the umbrella, and they just put it in their closet. They're waiting for that rainy day that they have to pull it out and start using it. VICTORIA: That makes sense. And I'm already in my head going through the people in my family who would benefit from this where, you know, I have family members who have a learning and a physical disability, and tracking everything that they're supposed to be doing to maintain their health is quite difficult. So, I can definitely see the value in that and why people would want to use it. And I think for, you know, healthcare apps, you have to build this high level of trust. You know, people are giving you all this data about their health information. So, how do you go about building a product that people can trust from the beginning? MARC: One of the things we sort early in the life of OtisHealth is an accreditation. An accreditation is not required by law. It's not required by any institution necessarily. It's a third party that reviews our practices and our systems to see if we're actually following good privacy and security standards and practices. And so we went live in November of 2021, and by the end of December of 2021, we already had our full accreditation in what's called a comprehensive level from a national established organization known as The Electronic Healthcare Network Accreditation Commission. And so, that was the first step of making sure that folks understood that we took their privacy and security seriously. That accreditation means that our practices and our technology meets or exceeds federal regulatory requirements and industry guidelines. And that's just the first step. Then after that, it's really a matter of people gain their trust because an accreditation itself doesn't necessarily mean that we trust that brand. That's just a basic starting point for us. After that, we publish articles about maintaining health. We have launched some videos about different aspects of our advocacy, such as with autism for caregivers. And we participate in community activities at the national level to improve patient access and to talk about how important it is to manage our own health and the health of our loved ones. And so, it's a combination of both basic accreditations that show that we made the investment, and we provided a third party to critique us and to review us. And we actively maintain that accreditation is not a one-time stamp. And then, the second part is continuous outreach, and letting the community know what we're working on, what's important to us, so that, over time, they start to look at what we do and start to trust it and invite other people to trust it as well. VICTORIA: That makes a lot of sense. And I'm curious if there were experiences from your corporate career that informed how you acted as a founder and what you prioritized. MARC: I've had an odd corporate career. [laughs] So, I started my career as an engineer in manufacturing operations and in product development and then went down to as a consultant strategy in ops and market management, and then, later, investment management and private equity, and then, later, for a safety science company where I was managing global capital investments in technology and new operations. And so, I've been fortunate that I've had a breadth of experience, from marketing to sales, to product and technology development, and infrastructure management. So, I had some basic skills that helped me understand what...well, the endeavor before I jumped into it because I spent a couple of years thinking about whether or not I even wanted to do something like this. And then, I would say probably the most important part of my previous experience that I apply every day at OtisHealth is developing teams and developing collaboration with different organizations. You know, aside from the team that I have, our own staff, we also work very closely with other organizations, even competitors, to make sure that we're all successful. And so, that collaboration across organizations that don't even have a necessarily contractual relationship is something that I brought over from my previous work and seeing how working across the industry, we can help each other and serve the mission. So, I think that was probably the most important part of my previous work experience that I apply today is this: building a team and building a coalition of organizations that want to move forward together. VICTORIA: That's great. And I'm wondering if there was anything that surprised you in that early phase of building collaboration with other companies and understanding your users that changed the strategic direction you were going with in the app. MARC: So, one of the things that I was really just in awe of was how willing people in the healthcare industry were to jump in and help out when we started talking. And so, many of the organizations that we work with, the founders or the senior staff within the nonprofits we work with, all have a story of why they're doing what they're doing. Many are brilliant people who could have taken their careers in many different directions, not in healthcare. And they chose to move forward in healthcare because of some personal experience in their life. And so, as I learned about the people I was working with, I was surprised how quickly they just took me under their wing and said, "Hey, let's get you started marketing. Let's move OtisHealth forward." And so, we have organizations like Onyx and Invitae [SP] that are giving us support in data access. There's another organization that I can't mention yet; that's another private entity that has offered their support, and we hope to launch with them in the next couple of weeks. And so, we're forming these data access bridges to help get patients more access to their data, their loved ones' data. And then, there's the nonprofits in the advocacy and standards organizations we work with, such as HL7, which is an international health technology standards organization, and DirectTrust, which is an organization that establishes trust networks in ecosystems, as well as the technology infrastructure behind how those systems communicate. And we work also with EHNAC, the accreditation commission. So, we not only are using the accreditation from EHNAC, we're on committees to advise them on future criteria for accreditation. VICTORIA: That's really cool. I love that there's that collaboration and just openness and willingness to try to make things better and to invest in solutions together. Mid-Roll Ad: VICTORIA: Introducing thoughtbot's ongoing maintenance service. Need reliable support and maintenance for your software? Look no further. Our expert team handles upgrades, bug fixes, UI adjustments, and new feature development. And the best part? Our maintenance packages start at just 5K per month for companies of all sizes. From Ruby on Rails to Node, React, and, yes, even PHP, we've got you covered. Trust thoughtbot for top-notch support and optimized performance. To receive a custom quote, contact sales@thoughtbot.com. VICTORIA: And with me here, I have Richard Newman, who is the Development Director on our Boost Team, to talk to me a little bit more about what maintenance actually looks like once you've built your software application, right? RICHARD: Hi, Victoria. VICTORIA: Hi, Richard. You have experience building applications. I wonder if you could describe to a founder who's considering to build an application, like, what should they consider for their long-term maintenance? RICHARD: Well, like you said earlier, part of what you're going for with that long-term maintenance is making sure the health of your project, of your application, is always there. And you don't want to be surprised as you're continuing to work with your users and so forth. And so, a number of things that we pay attention to in maintenance are, we're paying attention to keeping the application secure, providing security updates. We want to make sure that the ecosystem, basically, all of the tools and third-party services that are tied to your application that, we're responding to those sorts of changes as we go along. And then part of it is, occasionally, you're going to find some smaller issues or bugs or so forth as your user group continues to grow or as needs continue to change. You want to be able to respond to those quickly as well. And so, a lot of what goes into maintenance is making sure that you're paying attention and you're ahead of those things before they surprise you. VICTORIA: Because what can happen? Like, what are the consequences if you don't do that ongoing maintenance? RICHARD: Well, the security updates those happen across gems and in the platform sort of tools that are there. And so, if you're not keeping those up to date, your exposure, your vulnerability to being hacked, or having a bad actor come into your application start growing on you if you're not doing the maintenance. The other ones that can come up is there's new interfaces that these third-party services...they may be updating their APIs. They may be updating how you're supposed to work with their tool. And so, those can occasionally break if you're not paying attention to what's going on or you're suddenly surprised by an upgrade that you have to make. And then, finally, there's this long-term sort of code change that just builds up over time if you're not keeping it refactored for the changes that are upcoming in a language or the gems that you work with. And then, suddenly, after a while, it suddenly gets to the point where you have a lot of work that you might have to do to rehabilitate the application to take on some of the newer features that are being released. And so, that makes it that much more difficult, that much more friction about being able to deliver updates for your users or to be able to respond to changes that are happening out there in your application. VICTORIA: Right. So, if you don't have that ongoing maintenance, you could run into a situation where, suddenly, you need to make a very large investment and fixing whatever is broken. RICHARD: Absolutely. It's going to be very tough to plan for if you weren't keeping up all the way along and, yes, absolutely ends up being much slower if you have to remediate it. VICTORIA: That makes sense. I wonder if you have any examples of a project you've walked into and said, "Wow, I wish we had been doing a little bit more maintenance." [laughs] And maybe you can share some details. RICHARD: Yeah. We had a fairly large application that involved a number of clinic services. So, we had an application that users were going in every day and counting on our fast response. And, over time, we've got surprised by a database upgrade that had to happen. Basically, the database was going to be changed by our third-party hosting service, and that hadn't been tested. There hadn't been procedures in place when we discovered this need. And there was a very hard date that that change had to be done or else the entire application was going to go down. And it came at a very inconvenient time, at the end of the year around Christmas, that we had to respond to all of that. And had we been in front of it and just updated it every quarter and staying current with it, it wouldn't have been nearly the lift that it turned out to be. We were facing a pretty hard deadline [laughs] there to keep things going. It was very, very stressful and disruptive for the team and potentially for the clinics. VICTORIA: Right. And it always happens around a big holiday or something like that, right? When it all comes to a head. So... [laughter] RICHARD: Absolutely. You want to be in control of the timeframe and not have the timeframe be in control of you. VICTORIA: Right. And if you have a team like thoughtbot supporting you, you can go on your vacation with a little bit more knowledge that if something breaks, there's someone there who can respond and fix things, and you don't have to interrupt your very valuable time off. So... RICHARD: [chuckles] Absolutely. VICTORIA: Yeah. Well, thank you so much, Richard, for joining me today. I appreciate you coming here to talk with us. And we'll talk to you again soon. RICHARD: Yeah, it was a pleasure. Thank you. VICTORIA: You mentioned advocacy. And I'm curious if you could say more about what advocacy are you doing or how does that blend into your business model and what you're doing with OtisHealth? MARC: I'll give you an example. One of the organizations we belong to and I participate in personally is the Health Information Management System Society. And so, this is a professional society of healthcare IT professionals. And in Northern California, there's an advocacy committee that works directly with the state legislature to promote legislation that will improve the quality of healthcare for people in California. We actively talk to members of the legislature to tell them what bills we think are important. The ones we focus on and the ones I personally focus on are the ones that improve access to our data and also improve our privacy. So, there's a legislation in California, as an example, that will prohibit access to people's healthcare data without proper legal warrant. So, it's basically extending HIPAA protections across any health app launched in California. And we, of course, are already HIPAA-compliant, so that's very easy for us. There's also advocacy specific to certain health conditions. So, my daughter had autism. I work with the Autism Society here in California and also Achieve Tahoe, which is an organization that teaches skiing and other skills to people with disabilities in particular. This past season was my first season. I work primarily with children and young adults with autism and other developmental disorders. And then we also partner with organizations when we think that they're aligned with some of our mission. And so we work with the Caregiver Action Network. We also will work with AARP and other organizations regarding caregiver rights and also teaching caregivers how to access the healthcare data of their loved ones and how to take care of themselves personally. VICTORIA: That's wonderful. And I guess it's not really a question, but I saw that autism service dogs are a thing, and I just thought that was really cool. [laughs] MARC: Yeah, OtisHealth is named after Constance's autism service dog, Otis. And so, service dogs are extraordinary animals. They're highly trained. Otis had been trained for two years before we received him. He was trained specifically for Constance's needs, and he kept her safe. And that was the primary interest in Otis is observing things that she...because of her cognitive limitations, wasn't always aware of her surroundings and wasn't always safe. And so, the dog maintained her safety and her boundaries and kept her focused, as well as just basically blocked her if she was going to do something that was unsafe. So, there are many different kinds of service dogs, and I'm talking specifically about ADA, the Americans with Disability Act type service dogs. These aren't, like, companion dogs or therapy dogs. These are truly highly trained animals that are focused on specific tasks to help an individual be safer, more free, or have more abilities than their disabilities may allow. VICTORIA: Well, I love that. And I like that the app is named after her dog as well. That's just very sweet. And I love that that's how that worked. And I'm curious, what's on the horizon? What are you most excited about for OtisHealth in the next year? MARC: Like all startups, we have [laughs] a lot of plans. And we've been invited to speak at some conferences. I spoke at two already this year. And I have another one coming up in Washington, D.C., where we're going to advocate, again, for patient access. And this is primarily talking to the health systems themselves in adopting technology that makes it easier for patients to securely access their health records. And so, we're excited about that movement in the industry to recognize and start to act on that need for patients to be able to access their health records. And we work with our partners to promote that and also with the federal government. We work with the health and human services to promote this access. And we were published in a report earlier this year because of our technology demonstration with health and human services. And it sounds like it's finally getting some real traction in hospital systems. And members of the Federal Congress are also saying that this is something we need to move forward with in a more aggressive manner. On a more direct path, we're excited our membership's growing. We've had tens of thousands of people register to use the app, with thousands actively using it today. We're working on some new programs right now for payers and for providers that will improve health outcomes and within their populations, as well as bring on hundreds of thousands of other people on the app. We're really excited to know that we're getting both recognized for the work that we're doing and that people are starting to understand the importance of managing everyday health, whether it's with OtisHealth or another application. VICTORIA: Well, I love being excited for these opportunities to advocate for your product and for the mission behind the product. I'm not going to recommend being excited about going to D.C. during the summer. [laughs] Last time I was there when I landed at 9:00 p.m., it was 90 degrees outside [chuckles] and humid, like, 90% humidity. But it's great to have access to people who care and are trying to make things better and have that voice. I'm excited to see you grow. And then, it's been two years since you started the app. I wonder, if you could go back in time to when you first were getting started, what advice would you give yourself? MARC: So, this is a really hard thing for anybody to look back and say that they'd like to change a few things. There are things I would change. I have a lot of experience managing large, sophisticated programs. Because in the past I had large budgets, it was really easy to maintain strict discipline around the implementation. And I think I was too loose in the implementation process at the onset of OtisHealth. I would have been more disciplined around my program management and the accountability that I had to developers I was using. As a startup, I didn't have a large development team in-house. I needed to use external parties. And I should have been a little more closely on top of that process. The other things that we experienced were primarily a result of pivots. We were constantly pivoting as we were learning. I think having a team to review our process and pivot more quickly is really critical. You don't want to pivot 20 times a week. You need to stay focused for a while, but also having friends or advisors or members of your team that can help you assess when a pivot is necessary, or a new opportunity presents itself, I think, is critical. And so, we all know, as founders, the team is key. And I think the earlier you engage a team and not be bashful by asking for advice, the better. VICTORIA: I love that. And I'm curious if you have any advice from your program or from your startup career now on choosing the right development teams. And how do you find those right partners to actually build the app and have that accountability? MARC: So, I would say the number one thing that I've learned, that I knew previously, but I really appreciate it more now as a founder of a small company, is you need mission alignment, not just company to company, but person to person. And I took my time picking advisors to join us, and I took my time getting people on board to OtisHealth. We pick folks that we believe understand what we're doing, and we take our time and make sure that they appreciate it and that we're comfortable with them. Our startup is too small to make a bad hire or to have the wrong perspective because somebody has other motives, such as just making money. If I was providing advice in terms of picking teams or picking vendors to work with, I would say take it slow. Don't rush, even though you may be in a rush, or we may be in a rush to get moving, either for financial reasons or personal reasons. It's important just to feel comfortable. Get to know folks. Meet them in person if you can and spend a few hours with them at a time [laughs], just to make sure that they believe in you, and you believe in them, and that you have a common vision. Because when things get rough or tough, financially or otherwise, you need people that are going to be able to stick through it and work with you. VICTORIA: That makes a lot of sense. There's a lot of pivots happening. You want everyone to be on the same page. And you don't want to have to be corralling everyone all the time if they have competing priorities, so that makes a lot of sense. MARC: Absolutely. Just to be clearer on that, we all run into challenges. So, in some cases, we had to make some financial sacrifices, and everyone did it together. You really need people that are that committed that say, "Okay, I understand where we are, and so, I'm willing to take a pay cut for a while or not get paid for a while until we can get this spec started again." Even vendors I work with today that are strategic vendors understand that and have helped us financially when we need some time to get more revenue in. VICTORIA: Great. And so, when you were building a healthcare app, was there people you needed to have on your team who had that exact specialty in either patient care, or medical records, or something like that? MARC: Yes, yeah, you need experts. So, I'm a quick read. I mean, I spent a couple of years learning the industry and understanding the technology. But the person that's our IT director he has over 25 years of experience in healthcare IT systems, so he is the expert in-house. We also have advisors on our team that are experts in payer services and payer systems, launching healthcare apps, managing standards, and managing SaaS services. We have a data and an AI expert, and a clinical research specialist. We also have physicians we refer to. [laughs] So, we have a pretty big entourage of individuals that we go to for very specific advice and work. VICTORIA: That makes a lot of sense. Let's see, what question should I be asking that I haven't asked yet? MARC: You know, I think most of the people listening to this podcast are technical founders. And it was surprising to me, and I had some founders contact me, asked for some free advice, which I'm happy to do, but they didn't seem sincere in their interest in being in healthcare. And one thing I told them, and I would say to anybody that's interested in being a healthcare technology developer, is you have to have a reason to do it besides the money. It will be a really hard battle to move forward with a technology if the only motivation is a financial opportunity. That isn't going to sustain the pivots or the development. You'll run into a lot of walls, primarily because everyone will see it. Everyone in the industry sees those players come in that just have a financial interest, and the consumers see it, and they don't like it. So, my advice to anybody that wants to develop technology in healthcare is you have to be a little sincere about it and have a real reason to do it beyond just making money, and I think you'll find it more rewarding. There's so much need for healthcare technology and better technology out there. So, I welcome folks to join the fight, the battle, or the opportunities. But I would say that just come in with the idea that you're helping people, not just making money. VICTORIA: I think that rings true for any business you're in, right? But especially in healthcare because it is this big target. Even in consulting, if you're doing business development and you're thinking of working on health IT projects, there's just a huge market that you have to narrow down and figure out where you're going to be. So, if you don't have that intrinsic motivation, it can be overwhelming and scattered, and then people won't connect with you, right? Because everybody is going after the same thing. MARC: That's exactly right. One of the conferences I went to earlier this year, a speaker got up and said, "People invest in people, or people make deals with other people." We talk about companies signing a deal with another company, but it's really one person trusting another person. Whether it's in healthcare or another industry, obviously, that trust needs to happen. At some point, if I don't trust the individual I'm talking to, I'm less likely to have a deal with that company. VICTORIA: Right. It's like; I don't know how, you know, it doesn't really matter how impressive your credentials are. If there's not a basic level of trust, you might not move forward with it, so that makes a lot of sense to me. MARC: Yeah, that's absolutely right, Victoria. VICTORIA: Absolutely. Is there anything else that you'd like to promote at the end of this podcast? MARC: I'd love for folks to try OtisHealth. If you have family that have chronic medical needs or need help managing their medical information, please download OtisHealth, help them join. There are videos on YouTube that explain how to use it if you need some guidance, but we believe most of it is self-explanatory. We are continuously adding data access points. We're going to be launching this week new versions of OtisHealth that have access privileges for people in New York and Nevada and parts of California and Colorado. And so that means that with the app, once you're ID-proofed on the app, you can use it to get your medical records from different sources without having to log into all these different patient portals. So please try it. Use it for yourself but especially use it for your family or anybody who you care for. We'd love to get your feedback as you use the app too. VICTORIA: That's great. And I'm actually already thinking about...next week; I'm going to be going to The San Diego Annual Veterans Stand Down, where anyone who is experiencing homelessness can come in and get access to all the services that they might need, whether it's legal, or healthcare, or dentistry, showers, food, all of these things. And I'm curious if that organization might benefit from having a tool like that for their users. So, I'll be talking about it. [laughs] MARC: Oh, thank you so much. That'd be wonderful. Thank you. VICTORIA: That's great. Well, thank you so much, Marc, for joining us. MARC: My pleasure. Thank you, Victoria, for having me on the show. VICTORIA: Excellent. You can subscribe to the show and find notes along with a complete transcript for this episode at giantrobots.fm. If you have questions or comments, email us at hosts@giantrobots.fm. And you can find me on Twitter @victori_ousg. This podcast is brought to you by thoughtbot and produced and edited by Mandy Moore. Thank you for listening. See you next time. ANNOUNCER: This podcast is brought to you by thoughtbot, your expert strategy, design, development, and product management partner. We bring digital products from idea to success and teach you how because we care. Learn more at thoughtbot.com.Special Guest: Marc Mar-Yohana.Support Giant Robots Smashing Into Other Giant Robots

Introducing thoughtbot's ongoing maintenance service. Need reliable support and maintenance for your software? Look no further. Our expert team handles upgrades, bug fixes, UI adjustments, and new feature development. And the best part? Our maintenance packages start at just 5k per month for companies of all sizes. From Ruby on Rails to Node, React, and, yes, even PHP, we've got you covered. Trust thoughtbot for top-notch support and optimized performance. To receive a custom quote, contact sales@thoughtbot.com. __ Simon Ritchie, the founder and CEO of Blox, discusses his background and journey leading up to starting the company. He began his career in finance but discovered his passion for technology and finance systems. He worked at Anaplan, a successful finance planning and analysis software company, but saw the limitations of rigid systems when COVID-19 hit. He realized there was a need for a more flexible and accessible financial modeling and planning tool, especially for small businesses and charities. Blox aims to fill this gap by providing a powerful yet easy-to-use modeling, calculation, and planning engine that sits between spreadsheets and complex enterprise software. The company is about a year old, has raised venture funding, and launched a free tier of its product. They prioritize building a compelling product, iterating quickly, and engaging with users to understand their needs. Simon acknowledges that building the product has been enjoyable, leveraging his background in product management. However, sales, marketing, and customer traction have proven challenging. Nonetheless, he remains optimistic about Blox's progress and is committed to providing a valuable solution to help businesses make informed decisions and achieve their financial goals. Blox Follow Blox on Twitter, Facebook, LinkedIn, Instagram, or TikTok Follow Simon Ritchie on LinkedIn. Follow thoughtbot on Twitter or LinkedIn. Become a Sponsor of Giant Robots! Transcript: VICTORIA: This is the Giant Robots Smashing Into Other Giant Robots Podcast, where we explore the design, development, and business of great products. I'm your host, Victoria Guido. WILL: And I'm your other host, Will Larry. And with me today is Simon Ritchie, Founder and CEO of Blox, which provides pre-built planning models to help business leaders escape the tyranny of complex, clunky, and error-prone spreadsheets, giving you visibility into and confidence in the reality of your business. Simon, thank you for joining us. How are you doing today? SIMON: Hey, guys. Yeah, I'm very good today. VICTORIA: So, Simon, where are you joining us from today? SIMON: So, I'm joining from the UK. I live in a city called Brighton on the South Coast of the UK, where it's a lovely day today. It's nice and sunny. VICTORIA: Oh, that's where our thoughtbot summit has been the last two years, in Brighton, actually. SIMON: Fantastic. Yeah, it's a wonderful place. VICTORIA: And a great place to be in the summer right now, right? Do you get out in the water very often? SIMON: Yeah. Yeah, absolutely. Like many others, we have a paddle board. So, I go out with my family. I have four kids, so we go out and have fun at the beach. Brighton's got a stony beach. So we are, as Brightoners, we're very proud of the stones. You know, if you have sand, you get sand everywhere, stones are...it's much cleaner. [laughter] It does hurt your feet, though. There you go. [laughter] WILL: Yeah, that was the first time I've ever seen that, and I was like, that's very interesting. SIMON: Yeah. [laughs] WILL: I probably will like it because I don't like the sand getting everywhere, so... SIMON: Yeah, absolutely. WILL: So, yeah, I probably could trade that in. [laughs] SIMON: Yeah, yeah. You just have to wear shoes if you want to go run around. We're proud. We're proud of it. VICTORIA: I didn't think about that either. It makes a lot more sense. I don't really like the sand [laughter]. Rocks make more sense. But in California here, we're surfing, so having too many rocks on the beach would be a problem [laughs] for those of us who can't control ourselves. [laughter] SIMON: Yes. Yeah, Victoria, I thought you lived in Wales when I first looked at your profile -- VICTORIA: Oh, right. SIMON: On LinkedIn. And I thought, oh -- VICTORIA: That's...yeah. SIMON: A Welsh girl. That's -- VICTORIA: My family is actually Welsh on my mother's side. SIMON: Oh really? VICTORIA: Yeah. SIMON: Okay. VICTORIA: And Cardiff...California is named after Cardiff, Wales. SIMON: Okay, oh. VICTORIA: But yeah, so that's where it came from. So, I thought that was very cute, too. SIMON: [laughs] Very cool. VICTORIA: But, you know, Cardiff-by-the Sea is its own little beach town here. SIMON: It's not Wales. [laughs] VICTORIA: Not Wales. [laughs] Pretty different. But I do hear Wales is beautiful. SIMON: Oh, it is. Yeah, absolutely. VICTORIA: Awesome. Well, let's talk about Blox a little bit. So, why don't you tell us maybe a little bit about your background and how you came around to starting it? SIMON: Yeah, great. So, and just in terms of me and my background, so I started my career in finance, actually. I didn't really know what to go and study, so I thought, you know, studying numbers was probably a good thing. So, I did an accounting finance degree. And I got into the world of work in finance roles very quickly realized that finance wasn't for me. I just didn't really want to be a CFO. I just didn't feel the passion for it. But I was the techie guy always in the finance team. I was the guy people turned to and originally for, you know, Excel and spreadsheet modeling. And behind Excel, you've got VBA. So, you've got this little, you know, it was my first exposure to programming and some, you know, and what coding was. And so, I sort of just realized, actually, I love the technology side. And so, I followed my passion more into the finance systems arena. And my passion has always been...the focus of my career has been helping leaders understand what's going on in the business by getting hold of those numbers, the data that they have, and analyzing it, summarizing it, trying to draw insights from it so they can make decisions. And so, in the early days, it was lots of Excel spreadsheet modeling. And, in some businesses, there's still tons of spreadsheet modeling going on. And then the next phase of my career was actually working in...there are a number of software options that help you with planning, modeling, reporting, et cetera. So, I joined...well, I did some consulting for a while and then joined a company called Anaplan. And was an early employee, the company was still very early in their journey. They were just launching a European office, so I joined as one of the early European employees. And Anaplan went on, over the course of nearly eight years that I was there, to be [inaudible 04:31], absolute rocket ship, grew up to 2,000 people, and we floated on the New York Stock Exchange and then IPO in 2018. It was acquired last year for a very big number. So really fantastic time there. But to just talk about Blox, so I left Anaplan two years ago. The observations that I made that led to Blox ultimately were there were sort of three main aspects. Like, when COVID happened, the world changed radically. And what I saw...I was working in Anaplan. For anyone who doesn't know, Anaplan they focus on selling to large enterprise. So, you may not be familiar with the company if you're not a CFO or a finance person in a very large company. And they sell very expensive product. It's very, very powerful modeling, calculation, FP&A, finance planning, and analysis software. And so, companies...we were working with companies like Procter & Gamble, HP, Cisco, Google, and others. What I observed was when COVID kicked in, the FP&A system was too rigid. So, Anaplan, you know, these models that people had built up, spent a lot of time and energy building up, it was too rigid. The world changed so much that they couldn't really use their typical budgeting systems or these FP&A solutions. They couldn't use Anaplan. So, everybody just jumped back into a spreadsheet to figure out, you know, do I still have a business? How am I going to survive this if I just had to shut all my retail stores or if I had to send everybody home? You know, so everyone was using spreadsheets, basically. And so my observation there was that the tools that are available at that point are still way too hard to use. They're not flexible enough. You can't mold them quickly enough to really handle some of those scenarios that you want to throw at it as a leader. So, when you're trying to make big decisions about new revenue streams, new offices that you would want to launch, restructuring your team, investing in more people, those things they're really hard to model in the tools that are available. You need real specialist experience and expertise. That's very expensive, et cetera. So that was one part. And then the other thing that happened was I've worked most of my career in larger companies. And I'd worked in, yeah, in finance, in businesses. And also, I'm a chartered management accountant. It's all about helping with managing a business with your numbers. And I hadn't really worked with many very small companies. I ended up volunteering. When the lockdowns were happening, there were lots of people that were sheltering in place and they were staying at home. And so, a local charity had organized to put together food parcels, and then they found drivers to drive them around. And so I had volunteered through a friend of a friend, and somewhere my name got put in. So, I ended up driving these food deliveries around for the summer, and I loved it. Every Thursday, I'd take a couple of hours to just drive around and drop some food on people's doorsteps and then maybe have a quick conversation with them from a distance. I got connected with the charity. It is a local charity that runs on the South Coast in England here. And they found out I was an accountant, and I worked in software technology. They were like, [gasps], please, you can be our new best friend. We need some help. So, I ended up helping them a bit in their back office with some of the reporting that they do. And to cut a long story short, they're a charity. They live on grant funding that they get. So, they apply for grants, and then the grant providers want them to report back on the progress that they've made, the services that they've offered, the people they've helped. So, I went and helped them, and they needed these reports and some plans for grants that they were trying to get. What seemed really easy to me, like, they were showing me that they had to download this data from a system. And they needed to filter it and then count how many people they had been helping. And they basically were just, you know, with different needs and in different categories and cohorts. So, they would basically download the data, open it in a spreadsheet, put a filter on, select some filters, and then they would count the number of rows that had that criteria. And then, they would type the number into an email. And I just showed them some very simple things, like, when you do a filter or if you select the cells, you can see a countdown at the bottom-right in Excel, and I showed them that. And they almost fell off their chair because [laughs] they were like, "Oh, you know, why did we not see that sooner?" But I suppose through that, and, you know, through the various times that I helped them...and I just helped them with initially some spreadsheets and just some help with that. But it just showed me that there are a lot of businesses, a lot of charities in this case, but a lot of businesses where the leaders are not finance savvy, and they are not accountants. They're not MBAs, but they still need help running their business. They need to do reporting. They need to do planning, you know, manage their business, control the finances. So, I just thought, you know, just started thinking a lot more about what does a small business need? What does a leader in a business need to make great decisions, run the business? And how could we get them a tool or some software that doesn't cost hundreds of grand every year but is accessible, a nice, low price point, and really easy for them to use? And that's the problem that I thought about for a long time. And ultimately, that's what we're trying to work on with Blox. WILL: That's amazing. I used to work at a nonprofit. And I remember those days of, like, because I wasn't an MBA, like you said, MBA finance and just trying to figure out numbers. I don't even remember the software we used. SIMON: [laughs] WILL: But it was old and very hard to maneuver. [laughter] SIMON: Oh yeah. WILL: It was harder to maneuver than spreadsheets. And I was like, ahh, this is a nightmare. So, this is amazing that you're doing that. Can you tell us more about how Blox solves that issue? Because it sounds like it is a tween of big software that's for enterprise companies and spreadsheets. So, it's kind of in the middle; it sounds like. SIMON: So, spreadsheets are great. They're really easy. They're easy to start with. You'll often find that your spreadsheet will just kind of reach its natural end. It becomes too complex. And that normally happens when you've got, like, you're planning for lots of people, or lots of products, or lots of different projects. And so, you end up sort of having to figure out how to scale the model, you know, across lots of different columns or rows, or you start copying. And how you'll have three identical tabs or ten identical tabs. And, at that point, you've basically outgrown Excel, and trying to keep that spreadsheet running and working it becomes a real nightmare. And so, that's the point where Blox comes in. You could use Blox right from the very beginning. We've started with a focus on making really nice, simple models that you can just pick up and use. So, our earliest customers are startups doing a financial model for a brand-new idea. So, you can use Blox from the beginning, but you could probably use a spreadsheet, too. Where you would want to use Blox is where it becomes more complex, and you've got a lot more going on. You might have lots of different months, and you've got loads of time. You might want to connect it to your actual accounting system or a CRM system. And so, when you want to pull in actual data and do some reporting and maybe have different scenarios, different versions of a plan or of a report, that's where you've basically outgrown a spreadsheet, and it just becomes complex and unwieldy. And that's where you would want to move into a system. That's what we're building with Blox is basically a powerful modeling calculation planning engine that scales really easily. So, you can build up your dimensions, products, countries, time, et cetera, and you can build up those dimensions. You can build up your logic. You can add your own KPIs. You can add your own projection logic, et cetera. You can build out a model. We've got lots of template models that you can start with because you shouldn't have to start from scratch every time. You can get going. You can load up your own data very quickly at the beginning. For a lot of models, it's just assumptions. You're just trying to work out, okay, like, we've got some service businesses that use Blox. To get a basic model together, what you need to know is how many people do you have roughly? How much do you pay them? And then, how many people do you plan to hire at certain times? And how long does it take to ramp a new hire? Because, normally, there's some sort of ramp time. And if it's a service business and you're selling time, then you kind of have an average number of hours billable or often called utilization. So, with a few quick assumptions, you could throw them in. You could build out a multi-year plan for your business. And you could use that to think about, okay, how can I grow this business? I kind of talk about it as a financial roadmap that you could create. So, you know, often in the product world, we talk about product roadmaps. I like to talk about, you know, a business roadmap or financial roadmap. And that's really what we are working on; Blox and Blox will help you with this financial roadmap that you can build out. You know, I'd like to get my business to this point to, you know, 2 million in revenue, or 10 million in revenue, or maybe there are some financial or non-financial goals that you're trying to get to. And, with a model, you can help try and kind of work out what the assumptions and drivers and what those things need to look like. And then, as a manager of the business, you can start working on, okay, how do I increase my headcount? Or how do I decrease this particular cost per unit or various things like that? So yeah, that's a very high level on what we're doing with Blox. VICTORIA: Thank you for that. And I certainly can relate to that, having worked for several different consulting services companies and how difficult it can be to get software [laughs] to project that -- SIMON: [laughs] VICTORIA: Far into the future, like, to think about how you're going to hire, all the things that go into it. So, I'm curious about your own plan for Blox. Like, how would you describe where you are in your plan for the company? SIMON: We are a year old, actually just celebrated our one-year anniversary. In the last year, we've formed, hired an early team. We've fundraised successfully. So, we raised venture finance to fund the business. It's a complex product to build. We're trying to replace a spreadsheet, which has got tons and tons of features. They've been developing that for a long time. So, for someone to come across, it needs to be a relatively mature product. So, we raised venture funds from investors. We're busy investing that to build up the product and take that to market. It's been a fantastic year. And this is my first time as a founder. I've worked in leadership roles in technology businesses, in customer success, and in product as well. Yeah, I definitely would say working as a founder in a brand-new startup is very different to working in product, in a scale-up. You know, some of the lessons that I learned back there have been useful. You know, you learn how to juggle chaos, how to juggle...how to spin lots of plates. But yeah, I'm really delighted with our progress so far. We've fundraised. We ran a beta of our product last year with some early customers. We graduated from that. Our approach has always been to try and get the product out, so really embrace agile. It's kind of you don't see it so often in enterprise software. What you see is companies that like to just put "Book a demo" on the website. And they don't like to show their software until they've already kind of sold the value, and they've pitched, you know, positioned their pricing, and qualified their leads, et cetera. Our approach has always been let's build a fantastic product. Let's build something which is super compelling, super easy to use. Let's get people into the product as quickly as possible so they can experience it, see if it's going to be valuable for them. We launched a free tier of our product, the first sort of MVP, as a free tier, so not paid, not with some of the features that we plan to add to the product. And so, we've got that out there, and it's been fantastic. We've got users from all over the world using it in all sorts of different ways. And that's the other thing that is really great for us. Because it's such a flexible product, it can be used in lots of places. So, we've got all sorts of different applications being used by it. People jump in; they use it. They can try different templates that we've got. And then, if they need something different...every business is slightly different. So, if they need something slightly different, they can just chat to us in the product. We absolutely love chatting to people. And then, you know, we'll often spin up a custom template for them. And when we've done a few of those, then we'll build a standard template for a new industry. That's a little bit about where we're at. We're a small team based between here and India, where most of our developers are. It's good fun. Some of the learning...so I would say maybe it's just because of my background. So, I moved into product, and I was a product manager and then product leader for the last six years. So, for me, I've found building the product has been the easier part, probably because it's my background and that's where my passion is. So, I absolutely love anytime I get to spend in the product and spend with the team. The original founding team is myself as founder and CEO. And I don't get too much time on the product. I have a product manager and a designer. And so, that was the first...the early team, the founding team. And then we've added marketing and some other roles and software development. And so that's the team. I've found building the product has been really fun, and that's been a bit easier. Trying to work out how to do fundraising was a real challenge, so that took a lot of energy. We've been pretty successful so far in that. Still, always more to go, always more fundraising needed definitely. The really hard thing, especially in the market that we're in right now, it's hard, you know, getting early customer traction and selling. And that's really hard trying to get your name out there, build a brand, find early customers. That's really hard. So yeah, that's definitely an observation for me that the product has been really fun and a bit easier than I thought. But yeah, trying to do sales, marketing, figure that out...and probably as well because it's not my background or my kind of natural area of interest, so I've been learning. That's always tough, isn't it? Mid-Roll Ad: VICTORIA: Introducing thoughtbot's ongoing maintenance service. Need reliable support and maintenance for your software? Look no further. Our expert team handles upgrades, bug fixes, UI adjustments, and new feature development. And the best part? Our maintenance packages start at just 5K per month for companies of all sizes. From Ruby on Rails to Node, React, and, yes, even PHP, we've got you covered. Trust thoughtbot for top-notch support and optimized performance. To receive a custom quote, contact sales@thoughtbot.com. VICTORIA: And with me here, I have Richard Newman, who is the Development Director on our Boost Team, to talk to me a little bit more about what maintenance actually looks like once you've built your software application, right? RICHARD: Hi, Victoria. VICTORIA: Hi, Richard. You have experience building applications. I wonder if you could describe to a founder who's considering to build an application, like, what should they consider for their long-term maintenance? RICHARD: Well, like you said earlier, part of what you're going for with that long-term maintenance is making sure the health of your project, of your application, is always there. And you don't want to be surprised as you're continuing to work with your users and so forth. And so, a number of things that we pay attention to in maintenance are, we're paying attention to keeping the application secure, providing security updates. We want to make sure that the ecosystem, basically, all of the tools and third-party services that are tied to your application that, we're responding to those sorts of changes as we go along. And then part of it is, occasionally, you're going to find some smaller issues or bugs or so forth as your user group continues to grow or as needs continue to change. You want to be able to respond to those quickly as well. And so, a lot of what goes into maintenance is making sure that you're paying attention and you're ahead of those things before they surprise you. VICTORIA: Because what can happen? Like, what are the consequences if you don't do that ongoing maintenance? RICHARD: Well, the security updates those happen across gems and in the platform sort of tools that are there. And so, if you're not keeping those up to date, your exposure, your vulnerability to being hacked, or having a bad actor come into your application start growing on you if you're not doing the maintenance. The other ones that can come up is there's new interfaces that these third-party services...they may be updating their APIs. They may be updating how you're supposed to work with their tool. And so, those can occasionally break if you're not paying attention to what's going on or you're suddenly surprised by an upgrade that you have to make. And then, finally, there's this long-term sort of code change that just builds up over time if you're not keeping it refactored for the changes that are upcoming in a language or the gems that you work with. And then, suddenly, after a while, it suddenly gets to the point where you have a lot of work that you might have to do to rehabilitate the application to take on some of the newer features that are being released. And so, that makes it that much more difficult, that much more friction about being able to deliver updates for your users or to be able to respond to changes that are happening out there in your application. VICTORIA: Right. So, if you don't have that ongoing maintenance, you could run into a situation where, suddenly, you need to make a very large investment and fixing whatever is broken. RICHARD: Absolutely. It's going to be very tough to plan for if you weren't keeping up all the way along and, yes, absolutely ends up being much slower if you have to remediate it. VICTORIA: That makes sense. I wonder if you have any examples of a project you've walked into and said, "Wow, I wish we had been doing a little bit more maintenance." [laughs] And maybe you can share some details. RICHARD: Yeah. We had a fairly large application that involved a number of clinic services. So, we had an application that users were going in every day and counting on our fast response. And, over time, we've got surprised by a database upgrade that had to happen. Basically, the database was going to be changed by our third-party hosting service, and that hadn't been tested. There hadn't been procedures in place when we discovered this need. And there was a very hard date that that change had to be done or else the entire application was going to go down. And it came at a very inconvenient time, at the end of the year around Christmas, that we had to respond to all of that. And had we been in front of it and just updated it every quarter and staying current with it, it wouldn't have been nearly the lift that it turned out to be. We were facing a pretty hard deadline [laughs] there to keep things going. It was very, very stressful and disruptive for the team and potentially for the clinics. VICTORIA: Right. And it always happens around a big holiday or something like that, right? When it all comes to a head. So... [laughter] RICHARD: Absolutely. You want to be in control of the timeframe and not have the timeframe be in control of you. VICTORIA: Right. And if you have a team like thoughtbot supporting you, you can go on your vacation with a little bit more knowledge that if something breaks, there's someone there who can respond and fix things, and you don't have to interrupt your very valuable time off. So... RICHARD: [chuckles] Absolutely. VICTORIA: Yeah. Well, thank you so much, Richard, for joining me today. I appreciate you coming here to talk with us. And we'll talk to you again soon. RICHARD: Yeah, it was a pleasure. Thank you. WILL: You mentioned getting your product out there how challenging it can be. So, what has been some other wins and some challenges that you've had as a first-time founder? SIMON: So, my approach to things as a leader is I basically like to bring silliness and games to help motivate and energize the team. So, as a human, I have quite a lot of energy. I roll around with lots of energy. And I take loads of photos of what I'm doing, and I share those. So, we have a Friday wrap-up with the team, and so I'll often share a lot of the pictures of, you know, what I've been up to this week. So, yeah, there's been some really fantastic moments launching a product. We launched our MVP in three months. So, we basically set off...I actually funded the first season of the business, a couple of software developers, a couple of early employees. I funded the first season. We hadn't raised money. And I just spoke to my wife, and I said, "Look, now's the time. I really want to do this." You know, I've been saving up if you like, I had this, like, one day I'll do a startup fund. Some people would probably call that their long-term savings or like, you know, some...and I kind of called it my one day I'll do a startup fund. So, I'd been building up this fund because I knew that at some point, I'll probably go do this. The timing was way earlier than I thought. I thought I'd still do another four or five years in a career in a corporate role to try and get a few more notches in my belts to make fundraising easier, et cetera. The timing came. The team was perfect. And everything just felt right, so we went for it. But yeah, we basically set out. We didn't know where we were going to get funding from. The market was in a real state, so this was middle of 2022. The Ukraine war had kicked in; valuations had dropped by 90% for a lot of tech companies. The post-COVID bubble had burst. It was hard. So, we sat down, and we were like, okay, we could spend all of our runway trying to fundraise now, or we could crack on and try and build the first MVP. But we'd already done a lot of the market research, the user testing, early prototypes, et cetera. And that's a bit of a long story. But we had done that in the company that the founding team had worked at, and then we were actually a spin-out. So that happened. And we were sitting here thinking, okay, you know, we could spend all of our runway fundraising, or we could just crack on and build a product as quick as we can in the next three months. And so, we had this really hard conversation where we descoped so much stuff. And we just figured out what's the core piece that will really show the value of what we're trying to build, that we'd give to a user, that we could give to an early customer that they could use and get value from? And so, we came up with that scope. And we cracked on, and we built it. Within two and a half months, we had a working version. We played with it. Within three months, we kind of launched into this beta and got early users onto. So that was, you know, fantastic. So, we did that in the first three months, and then off the success of having an MVP, and just being able to show the product, and start getting some early user feedback, initial feedback was, you know, we took into account very quickly and improved. And just having that, you know, you basically start building momentum. Every step is still really hard, but you do build momentum. So, we got this product. We launched it. We went to a couple of events, and we talked about that, and then we did some fundraising. And we landed some funding, so that was fantastic. And then, you know, and then we've just gone sort of step by step from there. So, it's really fantastic what we've been able to achieve so far. The challenges there's been loads of them, especially when you're building a startup. It's really exciting. So, you can get people excited quite easily about the future potential. And you can kind of talk about what this can be. I've got a printed picture of a unicorn on my whiteboard in my office right here as a sort of a statement of, you know, where we're going. It's really hard as a founder or a leader trying to persuade people to leave a stable job, take a pay cut, and come and work with you and give them some equity, which you hope will be worth a ton, and you kind of paint the picture. But also, you don't know how long you can keep them because you're on runway. You're on runway. You haven't got infinite cash if it's not a profitable business. So, you know, there are some real challenges. And, as a founder, you go through ups and downs. Ben Horowitz talks about it in his great book, The Hard Things About Hard Things, as the struggle. I definitely understand that a lot more now because there is an up and down to this. You do build momentum, but you also...you're creating the momentum, you know, one hard push at a time. So that's that early customers come on. You kind of pitch the dream of what the product will do, and then it will fall over as soon as they touch it. But I absolutely love it. What I love is the chance to create and how quickly you can move in the early days of a startup or a new product, where you don't have masses of technical debt. You don't have hundreds of customers. You don't have all this, you know, you don't have a massive team where everyone's got their point of view on what you should do. So, you can move really fast, and that's fantastic [inaudible 30:14] creative season. So yeah, lots of ups and downs, but it's really fun. VICTORIA: That's so interesting and particularly interesting that you're trying to make something that's easier to use than Excel. So, I'm curious how you're testing to make sure that it's actually easy. And what might be...I'm sure there's some interesting feedback you got about that. SIMON: Yeah, so we're making Blox easier than Excel. But it's got to be powerful enough to be able to handle the data and the modeling that you need for a business. If you're doing projections for multiple years if you've got lots of products or teams, then it can be complex, so it needs to be powerful enough to handle that. It needs to be flexible enough because you can take a template, but every business has got its own unique quirks. So, it needs to be flexible enough that it can be tailored easy for a unique business. And then, crucially, and this is also important, it needs to be easy enough to use so that the person who understands the business can change the model to kind of suit their business. That's the bit that most of the other players, you know, the enterprise software that's available today, just that they haven't figured out how to make it easy enough so that a businessperson that, you know, doesn't have database experience, can't write SQL, not going to write Python, you know, doesn't do complex scripting or any of this stuff. It's got to be easy enough that they can, you know, tailor, reflect the way that their business works, the way that they make money, the way that their cost structure works, so they can figure out what drives the business. And so, if they're projecting revenue, they can work out the costs associated. So, one of our founding team is a UX designer, a really, really fantastic designer, very experienced. He's been in the game for 25 years since, way before it was called UX. And started doing graphic design, and then has done lots of branding and branding for some really fantastic, large companies, did lots of consulting. And then got into UX and how, you know, the art of wireframing and helping to make products easily usable. I call him my secret weapon. I've worked with some fantastic designers in the past, so, as a founder, I think I appreciate and understand the value of a really good design and a really good UX designer. So, Mike, our UX designer, has just been fantastic at that. He's very good at wireframing and very good at testing. And he's not a finance planning expert. That's why I call him my secret weapon because, you know, I understand planning really well, but sometimes I understand it too well. When I describe what a user is trying to do or, you know, what I expect a screen will look like, I'm just probably subconsciously replacing or recreating something that I've seen or used before, whereas he's coming at it brand new. He's not worked in planning or data modeling, or many of these things. He's worked in lots of different businesses. So, he comes at it with a mobile-first perspective. Normally, he's thinking about, okay, how could this be used by a busy leader on their phone and they're running around? And so, he's been really fantastic at helping to keep it simple and easy and to rethink and to create a product, which is just so different to what other tools in the space are doing. And that's some of the feedback we get. It looks so different. It works so different. But yeah, the hard thing is that spreadsheets are the most sticky tool, I think. They're just so useful for, you know, for everything where you need to get a list of things. You just start throwing it into a spreadsheet, and then you can, you know, organize it and improve structure over time. But yeah, it's a really sticky tool. And we train people how to use spreadsheets from early days from school. My 12-year-old daughter she already has been taught how to use a spreadsheet in school. So, what we're trying to do is create something which is easier. But there's also, you know, you want there to be some familiarity in there so that people will...to avoid some of the friction of the people who have it. No one really signs up to learn a new tool if they can avoid it. We're lazy. [laughs] VICTORIA: It makes sense that design would be a big priority for your product because that was your intention from the beginning, right? Is to make something that's easy to use, so you prioritize that as an investment. SIMON: That's right. That's absolutely right. Yeah. VICTORIA: What's on the horizon? What are you the most excited about for Blox in the coming months? SIMON: So, yeah, we've got some really exciting elements of our roadmap coming. So, yeah, really excited to see these things come to life. Like anyone working in building products, whether you're designing, doing product, sort of overseeing, or actually developing, it's so great to see these things come to life. You spend a long time thinking and chatting about them, imagining, ideating about how they could look. The thing that I'm just most excited about is—and that's probably why I love product—is, you know, you're building a product, and then you can...then you're talking to somebody about how they would use this. Or before that, you're talking about their day-to-day right now and what their problems are, and how you could help them save time, save money, et cetera. And so, you know, I absolutely love chatting to more and more different types of companies, leaders in different parts of the business. And, you know, especially in our space, it's mostly about, okay, how can I help? You know, how could we improve this planning process that we've got, whether it's, you know, planning for the cost of running a big project or trying to figure out how can I scale my business to reach my objectives? So, I just love chatting to lots of different leaders globally. So, I love going to events, chatting to people, fact-finding about how they run their business, how they think about finances, et cetera. In terms of the product roadmap, we're working on some exciting new scenario capabilities, so you can easily look at different scenarios around a decision. So, you might be trying to decide, you know, should I be aggressive with my investments and hiring, or should I be pessimistic? Or is there a middle ground? So, we're adding, like, scenario capabilities where you can build out different versions of that, and then easily compare and contrast, and then decide which one to do. We're working on some really...really enjoying working on some intelligent capabilities. So, again, in the search of making it really easy to use for a busy leader, for a busy businessperson, or a busy finance person, making it really easy to use. So, we've invested a lot in AI technology and been designing, developing POCs around how AI could help to onboard customers faster, how we could help to personalize models for businesses automagically. So, as soon as we understand the website of a user, what sort of industry they're in, we can automagically personalize the template for them, add their own KPIs, like, industry-specific KPIs, into the model, and throw in benchmark data and all these things. So, we've got some fantastic AI capabilities coming through the pipe and some data integrations. As we get out more and more, we're connecting to different data sources. So, yeah, exciting times ahead for the roadmap. And as we add more features, then we'll add different pricing tiers, you know, so we can try and offer a nice, affordable entry-level offering for Blox, but then we will, you know, as you get more and more different features, you'll pay at the appropriate level. So that's a little bit about what our future looks like. WILL: That's neat some of the things you have coming up. You mentioned AI and how you're kind of embracing that. Can you expound on that? Like, kind of I know you said some data models automagically is going to do it. But, like, where can you see the benefit for a customer to use that? Because I know AI can be scary and stuff like that. But, like, just kind of taking the fear out of it and talking about how beneficial it can be. SIMON: Yeah. So, there's lots of different places where AI can help. So, the typical model today for finance planning is you'd have a leader who's responsible for the business, and they're responsible for an advertising budget. You know, they just intuitively know, you know, where should I spend money, what's good return on my investment, what's, you know, what works. But when it comes to actually trying to model that, so how to put that into a financial model or some other model that you can understand the relationships between these things, put in the KPIs, have the formulas, calculating things in the right way at the right level, what you often find is that the leader is not the system's expert. So, you'll often have, especially in bigger businesses, you've got this expert data analyst or FP&A finance planning person that will do the modeling. So, we really believe that AI can be like a digital business coach to digitize that business advisory piece. So, the leader can be sitting down. They can be looking to try and improve some part of their business or understand some part of their spend and trying to work out, like, what would life look like if I increased my spend on this particular channel by X? And so, you know, we are looking at AI to help with lots of different areas around this. Initially, it's helping a new user to get onboarded with Blox. So, it's taking a template and helping to personalize it for their business. What we basically try and do is fetch as much data about a new user and a new company as possible. So, if their team is on their website, then we'll pull in their team. If their products are listed on their website, we'll pull in a list of their products and try and throw that into the model and take out a lot of the friction that you have. As a user in the new system, you have to type in everything normally. If you're trying to model a business, you used to type it all in or copy and paste it from a spreadsheet. So, we're looking at lots of options to help onboard new users. That has a good value add for us because we can increase the speed of adoption and help get users to value faster, which is great for us. And also, users are, you know, they're busy. They're impatient, and they want to understand what value they're going to get before they spend lots more of their time. So that's going to be useful for us and them. And yeah, helping to interpret the data. So, they'll connect us to their source systems. We'll be able to interpret what's going on, help them to understand different options and scenarios about how things might play out in the future. Basically, AI will help us to draw our insights that we can present to the user, will help explain what the user is looking at when they're looking at the model, so we can summarize some of the key insights so that they can use that. We're expecting to have all sorts of users, but we're really focusing on really busy leaders who may have a good understanding of spreadsheets and data, but they're just too busy, and so they don't have time. So, they want something which is quick and easy. Or leaders who don't have that expertise, so those are the ones that we really cater for. We try and keep it really simple and help guide them through the process, et cetera. So that's where AI is going to be, like, that digital business AI...We kind of kind of talk about this AI business coach concept. And, over time, we'll build up more and more elements to that coach capability. We call him Anton in our team when we talk. We'll add more and more capabilities to him. But we've built a number of different POCs. And we've launched a couple of those with some customers. We've been out to events and showing off these new capabilities to basically test them out, understand what's working, what's not. What more do we need to think about to productionize this proof of concept? So that's, yeah, it's a very exciting time to be working on those things. VICTORIA: I love hearing about that. That's super interesting to see where it's going to go. So, my last question for you today is, is there anything else that you would like to promote? SIMON: I think I would just say, yeah, if you're a leader running a business or maybe it's a service business, and you're trying to think about, you know, when hiring business planning, financial planning, anything like that, then I'd love for you to come over to Blox, and you can jump straight into the product from our website. You can sign up. I absolutely love chatting to people about their businesses and what they're trying to do with their finances. So, if you want to do that, you can sign up. You can chat to us. I actually take a lot of time to respond to people in there, so yeah, if you want to do that. Or, if you can, also find me on LinkedIn. You can search me there. Just strike up a conversation and say, "Hey, Simon, I'd love to chat about financial roadmapping or finance planning." Yeah, I absolutely just love to speak to different leaders that work right across the business in different roles and see how we can help them to build a business that really unlock the potential that they have in their business through a great understanding of finances. So, yeah, if I can be of help, I would love that. VICTORIA: Wonderful. And we'll have all those links in the show notes so our audience can go and take a look. WILL: You can subscribe to the show and find notes along with a complete transcript for this episode at giantrobots.fm. If you have questions or comments, email us at hosts@giantrobots.fm. You can find me on Twitter @will23larry. VICTORIA: And you can find me on Twitter @victori_ousg. This podcast is brought to you by thoughtbot and produced and edited by Mandy Moore. Thanks for listening. See you next time. ANNOUNCER: This podcast is brought to you by thoughtbot, your expert strategy, design, development, and product management partner. We bring digital products from idea to success and teach you how because we care. Learn more at thoughtbot.com.Special Guest: Simon Ritchie.Support Giant Robots Smashing Into Other Giant Robots

Introducing thoughtbot's ongoing maintenance service. Need reliable support and maintenance for your software? Look no further. Our expert team handles upgrades, bug fixes, UI adjustments, and new feature development. And the best part? Our maintenance packages start at just 5k per month for companies of all sizes. From Ruby on Rails to Node, React, and, yes, even PHP, we've got you covered. Trust thoughtbot for top-notch support and optimized performance. To receive a custom quote, contact sales@thoughtbot.com. __ Maggie Bachenberg, CEO, and Trisha Ballakur, CTO, are the co-founders of Pointz, a mobile mapping app that helps navigate bike and scooter riders through safe routes in cities. Victoria talks to Maggie and Trisha about their cycling backgrounds, how they met and became co-founders, and what they feel is the differentiator for their app versus what was/is already on the market for biking-related apps. Pointz Follow Pointz on Instagram, Facebook, LinkedIn, or TikTok Follow Maggie Bachenberg on LinkedIn. Follow Trisha Ballakur on LinkedIn. Follow thoughtbot on Twitter or LinkedIn. Become a Sponsor of Giant Robots! Transcript: VICTORIA: This is the Giant Robots Smashing Into Other Giant Robots Podcast, where we explore the design, development, and business of great products. I'm your host, Victoria Guido. With me today is Maggie Bachenberg, CEO and Co-Founder of Pointz, and Trisha Ballakur, CTO and Co-Founder of Pointz, a mobile mapping app that helps navigate bike and scooter riders through safe routes in cities. Just to get us started here, are you both cyclists? And if so, where do you do that at? What's your city? Where do you bike around? MAGGIE: Yeah, we both bike. So I live in Providence, Rhode Island, along with Trisha, and use my bike primarily as a transportation device. So I'm riding around from my house to work, to get groceries, to my friend's house, kind of all different types of purposes. TRISHA: Yeah, and I grew up biking but kind of stopped after age, like, six or seven. And it was only when I got to college at Brown, where I met Maggie, that I got back into it and felt more confident to get back on the bike. And that was completely actually because of Pointz. VICTORIA: Oh, that's nice. Yeah, speaking of confidence, I am not confident on a bicycle. I actually only learned after college. [laughs] And there's a video out there of my college friends helping me learn how to ride a bike. It's very cute. But still not my expertise. So I'm excited to learn more about it and learn about how Pointz could give you that confidence. So, whoever who'd like to start, why don't you tell me about what caused you to want to create Pointz? MAGGIE: Pointz was originally kind of my idea. And I got into biking in 2017 when I did a long-distance bike trip. I biked from Virginia to California. And it was my first time doing long-distance cycling, and I just kind of fell in love with it. But I realized that when I was riding, it was pretty scary to navigate cities in particular. And so, a lot of locals would redirect me onto different routes that were safer. And I was confused why this wasn't captured in a mapping app already. And so, that's kind of where the idea was seeded. But I didn't start working on it until I got to college and met Trisha. VICTORIA: Great. So you got to college, and you saw that there was a need to have easier access to biking and biking information in an area, right? MAGGIE: Yeah, exactly. VICTORIA: Very cool. What was that initial process like? It was just the two of you, and you started building stuff? How did you really get the traction going early on? MAGGIE: It started with doing some customer discovery interviews with local cyclists. And so we interviewed over 100 initially and just asked kind of what their biggest barrier was to start riding. And we kept hearing this recurring theme of people not feeling safe enough to go on different routes. And so we brainstormed a bunch of different ideas in a class that Trisha and I were in together. But we ended up landing on the one that we're working on today, which is, like, you know, the rating system, and then also putting the rating system of bike friendliness into a routing algorithm where people could actually find routes. VICTORIA: That's very cool. And was there anything that really surprised you in that customer discovery process? MAGGIE: Just maybe the consistency around people's fear and, like, I guess, being nervous on a bike because we were interviewing people of all types of backgrounds and experiences. And even people that were more experienced had this fear of getting hit by a car because of lack of infrastructure and that sort of thing. TRISHA: Doing customer discovery and chatting with so many different types of riders...and we call them riders, bike riders, rather than cyclists for the distinction that, you know, in the bike riding community, there's a lot of very avid fitness-geared cyclists, maybe who want to go on their bikes to burn calories and challenge themselves. A lot of people they would call themselves someone who rides a bike. And it's to those types of people where safety is really critical, especially in allowing new people to go and try to ride a bike for the first time or the first time in many years. And so, that's something else that we noticed from those customer discovery interviews is identifying the different types of riders. VICTORIA: Thank you. That clears it up for me because I never know to call someone a cyclist or a rider, but it makes sense that cyclist is more, like, the athletic pursuit versus riding and, you know, just trying to get about your day. [laughs] And it also makes me feel better that even people who are really experienced riders have fear of being unsafe or getting hit by a car because that's certainly what I'm thinking about when I'm [laughs] venturing out there. So, what was your initial build like for the app solving this problem? TRISHA: Initially, we had a couple of different Brown University interns or students working on it together one summer and myself included. And that evolved to me and this one other student who was working with us figuring out how to transition the app from, like, an iOS Swift native app to React Native so it could be cross-platform. And we had to teach ourselves React Native for that. So our intern at the time he had done an internship during the summer at this one startup where they taught him React Native. So he had done a couple of projects there. And I had a little bit of experience writing in JavaScript but really not as much as him. And so, together, we worked on coding the app from what we had in iOS in Swift, which was pretty limiting. But, at the time, it wasn't very much. But we were able to replicate that in React Native during; I think it was my junior...Maggie in my junior winter break. That became the start of our MVP, which had many, many more iterations to get all the features in and was a little bit slow to build until when we released it out, which was our senior year in about March or so. VICTORIA: So that's really exciting. So, like, how long did it take you to really get to that initial MVP with the team that you have? TRISHA: It took quite a bit longer than expected, as with all sorts of technology when you're building it for the first time. So what was important to us throughout the process was making sure that all the features we put out there were really well tested, and were useful, and were actually solving the problem of providing safer routing. And to get to that stage, at first, we, you know, we had an app in Swift. Then we wanted to make it cross-platformed, and we needed to have the routing algorithm actually take those different weights, the different bike friendliness ratings of the roads into account. And that took a lot of researching and talking to mentors. So there were quite a few really hard challenges to get to the MVP, which is why it spanned about a year to get to that point. But throughout it all, we worked with other students at Brown. Then we pulled in some front-end contractors from online, like contractor sites, who were awesome. And we were just focused on being really scrappy to get it out in March of 2022. VICTORIA: That's great. And maybe it felt like a long time, but I feel like a year for a really solid MVP is pretty good, [laughs] especially when you have those safety concerns, and the quality of your data, and what you're giving out is super important. So now you've got the MVP, and I believe you just raised your round of seed funding last year. What was that process like for you? MAGGIE: Yes, so the round of funding that we did, we raised the first initial amount actually going into our senior year, and that was from a firm called Rogue Venture Partners. And we also got a little bit of it from their Women's Fund. And, yeah, that was the kind of piece of funding that got us started and allowed us to really, you know, add additional resources to the product to get it out there, at least the MVP. And then, after that, we got a little bit more funding from them. And then we raised money from Techstars as well because we got into their accelerator at The Roux Institute. That's kind of in association with Northeastern, and that was out of Portland, Maine. I guess it wasn't really necessarily, like, a cohesive round. It was, like, a couple of different checks that all kind of went into, like, our early funding for Pointz. And I would say it was very much so based on, you know, our relationship that we had with our initial venture firm that were working with Rogue. They actually mentored us for quite a few months before they invested in us. So they started mentoring us our junior year when we were in school. And then we got the deal together September of 2021. VICTORIA: That's awesome. Well, congratulations. And I'm glad you were able to find the right partnerships, and mentors, and funding that you needed. What did you find was really the differentiator for your app versus what was already on the market for biking-related apps? MAGGIE: There are a couple of different types of competitors, so there are the biking-related apps that you just mentioned, and then there are the general kind of use case apps like Google Maps or Apple Maps. And so, for the bike-related apps, the main thing that's different about Pointz is that we're more focused on, like, bike riders in general, so people that are riding around for transportation and recreation, not so much the cyclist type of a person that Trisha described earlier. So, you know, a lot of our features are geared towards people that are getting around the city or maybe are exploring a city or a neighborhood. It doesn't necessarily have to be a city, but that's kind of the focus. Whereas for other cycling-specific apps, like Komoot or Ride with GPS, it's focused a lot on, like, the fitness side of things and the recreation fitness side of riders. And so, at least the Ride with GPS and a few other of, like, the technologies that are available to more hardcore cyclists tend to have a more sharp learning curve. And ours was built more as, like, a general use case in navigating and exploring. VICTORIA: That makes sense. So it's more for people like me who are trying to go the most scenic [laughs] or the flattest and the safest way, not necessarily the fastest or the more fitness-focused aspect of cycling and biking. MAGGIE: Yeah, exactly. And, you know, we actually built this for people like us. Granted, I did do that long-distance bike trip. But, generally, I don't consider myself that hardcore of a rider, I mean, in my daily life. So it's for people who don't really identify as a cyclist and are more just, like, riding their bike around and, honestly, for people who are new to riding in general. Because a lot of our riders have recently gotten into biking or have recently moved to a new area, and so, they're just trying to figure out, you know, where are the good places to ride? Where do I feel safe? And, you know, how can I get more comfortable on my bike? VICTORIA: I'm loving this idea because I have a bike that's been sitting in my patio for over a year. [laughs] I haven't used...my partner is like, "Can we get rid of it? Because you don't use it." But I'm like, "I will. I will use it." I know my neighborhood problem is that there are giant hills if we leave our street here. So getting out is fine. But getting back in [laughs], it's like you need an electric bike. So that's very exciting. So, tell me more about now that you've graduated and you're taking this up full time; what does the future look like? What's on your horizon? MAGGIE: I mean, we've been working a lot with one of our advisors on, you know, getting to the point where people really love the product, and that's been kind of happening over the last year. We met Anuj Adhiya from Lenny's Newsletter. We've been working with him to really hone in on what the thing is that people really love about Pointz and make that experience better. And then also figure out what exactly the persona is so we can target them eventually with marketing, which is kind of the stage that we're at right now. So we were seeing our retention curves really evening out in especially a couple of cities that we're targeting. And so, this summer, we're focusing on getting our user base up in Los Angeles and then trying to figure out how, like, a playbook for scaling up a user base in a specific geography. Right now, a lot of our users are distributed throughout the United States. And there are clusters, but there's not, like, a huge spike in one city. And so, that's what we're working on right now is figuring out how to get a geographic kind of density to happen. VICTORIA: That makes sense. And it sounded like the app also uses a lot of user-generated data for safety ratings and things like that. Am I getting that accurately? TRISHA: Yep, that's correct. And what we do is we have a bunch of different layers of our data that we pull from. We have a base layer of data that comes from OpenStreetMap, and then we build on top of that. We rate all roads on a one through five bike friendliness scale. And building on top of that, we pull from city-specific data sets from cities, and towns, and municipalities. And then, we layer on the crowdsourcing similar to how Waze does at the top. VICTORIA: Got it. So taking advantage of that open data, the open city data, and what other data the city is putting out there. Are you finding that you're using whether or not a city has open data to inform if you're going to expand into that location? MAGGIE: Kind of as a focus point. So, the way it works right now is Pointz is available actually anywhere in the U.S. So; it doesn't matter if you're in a city or a rural area, you can use Pointz. And you can use it for routing and navigation and all the features that are available. However, we only have visualized the ratings in all 350 or so urban areas in the U.S., and so those are all visualized, but not all of them have the supplemental city-data. And so, the way we decide when we pull in city data is based on gaps in, like, the base layer. So, if we're seeing that there are a lot of accuracy issues in a specific city, we'll go, and we'll look and see if there's a more accurate map that the city has put out or that an advocacy group has put out. And so, we've done this recently in Chicago, Minneapolis, Portland, Oregon, just to supplement the base layer of data, and it has helped a lot in terms of accuracy. And users or our riders really like it. VICTORIA: That's great. And what is your current level of usage in the app? How well have you been adopted? MAGGIE: Are you talking in terms of, like, user numbers or just, like, our engagement levels? VICTORIA: Yeah, whatever you're using to measure your level of engagement or number of users on the app. Like, what are your stats looking like? MAGGIE: Yeah, so, we use...we have our overall signups. And then we have a subcategory of, like, active and engaged users. And so, for our overall signups, we're at just over 9,000 total signups since we launched the MVP, and we haven't marketed it at all kind of until right now, where we're trying to push it out in LA a bit more. And then, in terms of our engaged cohort, I'd have to pull up the exact number. But last I checked, it was around 1,800 monthly active users. We kind of look at that cohort, and then we break it down into, you know, who's even more engaged in that? Who's coming back every week, every day? Mid-Roll Ad: VICTORIA: Introducing thoughtbot's ongoing maintenance service. Need reliable support and maintenance for your software? Look no further. Our expert team handles upgrades, bug fixes, UI adjustments, and new feature development. And the best part? Our maintenance packages start at just 5K per month for companies of all sizes. From Ruby on Rails to Node, React, and, yes, even PHP, we've got you covered. Trust thoughtbot for top-notch support and optimized performance. To receive a custom quote, contact sales@thoughtbot.com. VICTORIA: And with me here, I have Richard Newman, who is the Development Director on our Boost Team, to talk to me a little bit more about what maintenance actually looks like once you've built your software application, right? RICHARD: Hi, Victoria. VICTORIA: Hi, Richard. You have experience building applications. I wonder if you could describe to a founder who's considering to build an application, like, what should they consider for their long-term maintenance? RICHARD: Well, like you said earlier, part of what you're going for with that long-term maintenance is making sure the health of your project, of your application, is always there. And you don't want to be surprised as you're continuing to work with your users and so forth. And so, a number of things that we pay attention to in maintenance are, we're paying attention to keeping the application secure, providing security updates. We want to make sure that the ecosystem, basically, all of the tools and third-party services that are tied to your application that, we're responding to those sorts of changes as we go along. And then part of it is, occasionally, you're going to find some smaller issues or bugs or so forth as your user group continues to grow or as needs continue to change. You want to be able to respond to those quickly as well. And so, a lot of what goes into maintenance is making sure that you're paying attention and you're ahead of those things before they surprise you. VICTORIA: Because what can happen? Like, what are the consequences if you don't do that ongoing maintenance? RICHARD: Well, the security updates those happen across gems and in the platform sort of tools that are there. And so, if you're not keeping those up to date, your exposure, your vulnerability to being hacked, or having a bad actor come into your application start growing on you if you're not doing the maintenance. The other ones that can come up is there's new interfaces that these third-party services...they may be updating their APIs. They may be updating how you're supposed to work with their tool. And so, those can occasionally break if you're not paying attention to what's going on or you're suddenly surprised by an upgrade that you have to make. And then, finally, there's this long-term sort of code change that just builds up over time if you're not keeping it refactored for the changes that are upcoming in a language or the gems that you work with. And then, suddenly, after a while, it suddenly gets to the point where you have a lot of work that you might have to do to rehabilitate the application to take on some of the newer features that are being released. And so, that makes it that much more difficult, that much more friction about being able to deliver updates for your users or to be able to respond to changes that are happening out there in your application. VICTORIA: Right. So, if you don't have that ongoing maintenance, you could run into a situation where, suddenly, you need to make a very large investment and fixing whatever is broken. RICHARD: Absolutely. It's going to be very tough to plan for if you weren't keeping up all the way along and, yes, absolutely ends up being much slower if you have to remediate it. VICTORIA: That makes sense. I wonder if you have any examples of a project you've walked into and said, "Wow, I wish we had been doing a little bit more maintenance." [laughs] And maybe you can share some details. RICHARD: Yeah. We had a fairly large application that involved a number of clinic services. So, we had an application that users were going in every day and counting on our fast response. And, over time, we've got surprised by a database upgrade that had to happen. Basically, the database was going to be changed by our third-party hosting service, and that hadn't been tested. There hadn't been procedures in place when we discovered this need. And there was a very hard date that that change had to be done or else the entire application was going to go down. And it came at a very inconvenient time, at the end of the year around Christmas, that we had to respond to all of that. And had we been in front of it and just updated it every quarter and staying current with it, it wouldn't have been nearly the lift that it turned out to be. We were facing a pretty hard deadline [laughs] there to keep things going. It was very, very stressful and disruptive for the team and potentially for the clinics. VICTORIA: Right. And it always happens around a big holiday or something like that, right? When it all comes to a head. So... [laughter] RICHARD: Absolutely. You want to be in control of the timeframe and not have the timeframe be in control of you. VICTORIA: Right. And if you have a team like thoughtbot supporting you, you can go on your vacation with a little bit more knowledge that if something breaks, there's someone there who can respond and fix things, and you don't have to interrupt your very valuable time off. So... RICHARD: [chuckles] Absolutely. VICTORIA: Yeah. Well, thank you so much, Richard, for joining me today. I appreciate you coming here to talk with us. And we'll talk to you again soon. RICHARD: Yeah, it was a pleasure. Thank you. VICTORIA: I'm wondering if you have any incentives built into the app for users who are, like, contributing data back, or maybe they're writing every single day. Are there any little challenges or achievements that you could unlock within the app right now? MAGGIE: We do have some gamification, yes. And so, the way that people can earn points on the app...we call them points with a Z because of the name. The way that they can earn those points are a couple of ways. So, one is through riding their bike and using Pointz as a navigation tool or as a tool to record their ride. And so, for that, you get one point for every mile. And then the second way is by contributing to the map, so either crowdsourcing an amenity like a bike parking that isn't on the map already or by adding information about a hazard that might be on the map, like, for example, a car parked in the bike lane. And for each of those, you know, you get one point. And so, yeah, we have that gamification system built out and a couple of...like, we have a leaderboard. And then, also, we have, like, a way for you to kind of go up in your avatar on the app. But besides that, we do monthly contests. And so, this past month, we partnered up with a company called Po Campo, which makes stylish bike bags that can be taken off your bike and then worn as, like, a purse or a handbag. And so, they sponsored the prize, which is one of their bags, and whoever kind of gave the highest quality and quantity of crowdsourcing reviews and miles ridden they're the winner of the contest for this month of June. VICTORIA: That's very cool. I love to see that and hear about what strategies people have for engaging with their users within the app. I'm curious to go back to, you know when you two first met, how did you know that you were going to be good partners to work on this project together? TRISHA: One of the ways that we knew that was because we had first been introduced to each other from our mutual friend who is a close friend of both of ours, and she had been telling the other person about each other. And it was one day where we just met up, and we really clicked. But, at that point, Maggie was looking for someone who could work on the mobile development, and I didn't have any experience with that. However, I joined a club, which Maggie was leading, which was called The Women's Entrepreneurship Group. And we got a chance to work together and plan out many events, including a large conference right before COVID hit. Like, we saw how we'd worked together. We really enjoyed it. And we had very similar aspirations and motivations towards entrepreneurship. When I had the chance to basically join what Maggie was already working on with Pointz in the summer of 2020, I knew that that was going to be a great opportunity. And we decided to become co-founders by the end of the summer. VICTORIA: That's very cool. And I know how important it is to have the right team together to work on a project like this and to start something up from scratch. So, were there other big turning points? And you mentioned COVID, so I'm curious how that affected the growth and progress of this effort. MAGGIE: Yeah, to be honest, in the heart of COVID, like 2020, we weren't really built yet. So, it didn't quite affect us a whole lot, just because the product didn't get launched until the spring of 2020 to actually, you know, kind of publicly. But there were a couple of other turning points in our company, one of them was Techstars and kind of the progress we made during Techstars. We joined the accelerator, and we were having a bit of a hard time getting tech kind of pushed out really quickly. It was taking us a long time to build the features. And so, Trisha and I kind of evaluated why that was happening. And we came up with a process that worked a lot better, which we still use today. And speaking of team, we got a couple of really awesome teammates that made a huge difference on how quickly we could turn around features and bug fixes. And so, that was a really big turning point because we were able to iterate much more quickly and get feedback from our riders a lot faster. So that happened November, December of last year, of 2022. The other big turning point, I would say, is the slider that we released in March of this past year of 2023. And so we were having a hard time retaining users and getting them to really like the routing because people who bike tend to be very opinionated. And if the route isn't exactly kind of how they wanted it, they would be upset. And so, we'd fix it for one group of users, and then we would upset another group that didn't want that, you know, added to the routing. What we ended up doing was releasing this safety slider, which has the fastest routes on the left side of the slider and then the safest or the longest routes on the right side of the slider. And that really helped people get a wide variety of routes that fit their use case. And it's helped a ton with retention. And also, the feedback we were getting from users really changed from, like, really honing in on a very specific issue with routes that they were getting to general feedback about how we could enhance the app and keep people coming back more consistently. TRISHA: I just want to emphasize again that, yeah, the team is really critical. And, like, on our team, we have really awesome people who are 10xers and just great. Also, have someone who worked at MapQuest and has...I think our combined mapping experience is around 20-plus years. So it's really awesome to have that sort of a team together. VICTORIA: Yes. And, you know, talking about it now on the podcast, in retrospect, I'm sure it all seems like it came together, and it was kismet, and everything just worked. But was that how it really felt? Or were there moments where you doubted it and thought, maybe this isn't going to come together? MAGGIE: Yeah, definitely. There were moments of that feeling. One thing that gave us a lot of confidence was getting to the point where we felt like we could really iterate quickly and release features at a consistent and predictable cadence. So that gave us confidence that you know, there is a process for this, and there's a process of gathering user feedback and rider feedback, and then translating that into features, or bug fixes, or UI fixes. I think that gave me a lot of confidence that we could solve it. But, of course, it always takes a lot longer than you expect. And our advisor, Anuj, always says that 80% of what you're going to do won't work and 20% of it will. And it's all about how quickly you can iterate and figure out what works. And sometimes you get lucky, and it happens quicker. Or maybe you have unique insight into the problem, and you can guess, and it works out quicker. But I don't know; I definitely think it's been a learning process for everyone on our team. VICTORIA: That's great advice. And now that you've got your velocity up and you have your confidence, what's on the horizon? Are there new features that you all are working on that you're excited about? TRISHA: Yeah, so we're really excited about leaning into the whole generative AI trends that are happening, especially with ChatGPT and others. One thing that we've been hearing from most of our riders, people who use Pointz, is that using the app to create routes, which will allow them to explore new places, go to a new coffee shop that they've been hoping to go to but just don't know how to actually get there is critical. And most of our riders on Pointz are people who are new to a city. Maybe they've only lived there for a max of one year or less. So, exploring the area around them is really important to them, and that's why they use Pointz. And so, leaning into that, we're going to be releasing, in the next couple of weeks, a new explore feature where someone can go and, you know, describe to Pointz what type of route or...not even route, what type of things they want to see in a city, and Pointz will come up with that. It'll learn their preferences and continue to suggest really awesome places to get to, which they can do car-free, basically, through bikes, because they can be safe and, you know, they can rely on this app to get them through the city safely. VICTORIA: That's really exciting. And I'm excited to try it out myself [laughs] once you have that feature launched. Maybe you can tell me how that feature plays into...or what your success really looks like for Pointz in the next six months. MAGGIE: Yeah, so I think that feature is something that will be, I mean, of course, we got to test it, but I think that it will help people kind of use Pointz as an exploration tool more effectively. People are already using it for that, but it's not specifically built for exploration. Right now, it's built more for, I guess, routing to, you know, new places but not specifically, like, oh, let's go on a route that takes me through all these tourist destinations in the city I'm visiting. But this new feature will allow people to use it for that more. And I think, overall, you know, our mission at Pointz is to help people feel comfortable riding bikes so that they can drive less and feel like they can get around in a sustainable fashion, rather than having to rely on their car so often. And this feature is tied to that in the sense of, like, people can use it as a tool to help them, you know, find the safe route or a route they're comfortable with, and then use it to explore an area but maybe a bit more geared towards, like, tourists or, you know, more recreational-type use cases. VICTORIA: That's very cool. Thank you so much for sharing that. And what is your biggest challenge to achieving that success? MAGGIE: I think biking is a first step in that process of helping people feel like they can be more car-light or car-free, you know, use their car less. There are obviously a ton of other factors that go into whether or not you're driving, or you're taking a bike, or you're taking public transportation. And, you know, our next steps after we have really nailed this product are to explore those opportunities and build tools that help people choose alternative transportation more often. That's what we're excited about going into the future. You know, there's a ton happening in cities all across the U.S., not only for biking but also investments in transit, infrastructure, and whatnot. So, you know, young people and people of all ages...I think a lot of people feel comfortable and that they don't want to be sitting in traffic a whole lot [laughs] because that's not fun for anyone. And, you know, traffic and congestion is always frustrating. So, as much as we can reduce that, I think that's the mission of our company. And, of course, it takes a ton of scale. But it's a big goal, but we're going after it. VICTORIA: That's great. You know, I heard about a town in the U.S. that actually had banned cars and was pedestrians only for the whole town. It's like, what a great idea. [laughs] But I love it. I love that you're working on it. And I wonder now, you know, you're a couple of years into it. If you could go back in time and give advice to yourself when you first started this project, what advice would you give yourself? MAGGIE: For me, I would say to get a minimal viable product more minimal, [chuckles] so reduce it to, like, a single feature, get it out quickly, and start getting feedback more quickly from, like, a very practical, you know, piece of advice. And then, like, an overall piece of advice would be just to be more confident earlier on. It took a long time for me to gain the confidence of, like, being a thought leader in the space. And, you know, I felt like I was young, so there were all these people that knew more than me. But I think everyone has a really unique perspective, and if you really lean into that and share that with the world, it can inspire a lot of people. And you just have to be confident enough to do that. TRISHA: Yeah, I definitely second what Maggie just said. I think also from the tech perspective, if you're someone who is maybe more inexperienced, like, I just got out of college and did this, and I have never worked a full-time job before anywhere except this. And so I think there was a lot of doubt that I had of being able to lead the technical side because I didn't have 20 years experience working somewhere. But, actually, at the end of the day, that doesn't matter. It just matters that you're able to be in touch with what it takes to build certain features and talk to the users, or your riders, or whoever because they're the ones who are going to be dictating whether this is a success or not based on what you build. It's really not good if you're building and wasting a lot of resources and time on features which nobody wants or nobody uses. And so, that's been core to why I think I've gotten a lot of confidence in being able to be, like, the tech leader in this app and in this space. VICTORIA: Yeah, I'm curious to hear more about that. You touched on this really being your first full-time job. So, how do you build your personal brand as an executive leader in this company that you're building? TRISHA: For anyone who does startups, they'll know that it's a lot of figuring it out as you go, and things that you're taught in school don't necessarily translate well to the startup world because, like, I did, like, a Bachelor of Science in Computer Science. I did operating systems. I built a whole bunch of random stuff in school, and I studied for hours and hours. Of a lot of that, the most important thing, which actually translates to working in my field, is the perseverance to, like, keep going and working really hard. Otherwise, none of that stuff which I learned honestly translates. I had to learn everything myself with regards to building mobile apps. And I think the foundations were really critical from school but not really much of the hours of studying. I don't think that that's necessary, but I think it's necessary to build that sort of perseverance mindset. VICTORIA: That makes sense sort of to reflect that back a little bit, just having the perseverance to keep pushing, and keep learning, and keep understanding what is it going to take to build the features that you want? And that's really the core of being a CTO, right? TRISHA: Exactly. Exactly. Yeah. VICTORIA: And, Maggie, I wonder about you as well, like, what resources are you drawing on to really perform as a CEO for this company? TRISHA: One thing that I read a lot is...it's more product-focused, actually, but it's product and growth-focused. It's Lenny's Newsletter, which I mentioned earlier. I use that as a resource a lot. I listen to their podcasts, and I read their articles. And then secondly, I interact a lot with other CEOs and founders because I think that's one of the best ways you can learn is from other people who are in it right now, maybe are a couple of steps ahead of you, or who have done it before. And so, I lean into that quite a bit. And just, you know, try to get advice from people, take what makes sense, and apply it to what we're working on. VICTORIA: That sounds great, yeah. I can relate to that; just building your personal network with people who are in similar roles helps you stay in touch and understand what other challenges people are facing and what you might face someday, right? [laughs] That's really cool. I love that you have all that set up. And is there anything else that you all would like to promote today? MAGGIE: I would just say to anybody who's interested in biking or maybe is, like, a beginner rider, we'd love to have you try out the app and then explore your area and give it a try one weekend when you have some time and see if you feel more confident, you know, given the routes that are on more green and protected roads. VICTORIA: I'm really excited to be talking to you because I am that person. I need this app. [laughs] I'm excited to try it out. Thank you, Maggie and Trisha, for joining us today. [laughs] It was a really great conversation, and I'm excited to follow along and see what happens with Pointz in the coming years. You can subscribe to the show and find notes along with a complete transcript for this episode at giantrobots.fm. If you have questions or comments, email us at hosts@giantrobots.fm. And you can find me on Twitter @victori_ousg. This podcast is brought to you by thoughtbot and produced and edited by Mandy Moore. Thank you for listening. See you next time. ANNOUNCER: This podcast is brought to you by thoughtbot, your expert strategy, design, development, and product management partner. We bring digital products from idea to success and teach you how because we care. Learn more at thoughtbot.com.Special Guests: Maggie Bachenberg and Trisha Ballakur.Support Giant Robots Smashing Into Other Giant Robots

Introducing thoughtbot's ongoing maintenance service. Need reliable support and maintenance for your software? Look no further. Our expert team handles upgrades, bug fixes, UI adjustments, and new feature development. And the best part? Our maintenance packages start at just 5k per month for companies of all sizes. From Ruby on Rails to Node, React, and, yes, even PHP, we've got you covered. Trust thoughtbot for top-notch support and optimized performance. To receive a custom quote, contact sales@thoughtbot.com. -- Brittany Martin is an Engineering Manager at Shogun, where she manages a team of Ruby and React engineers and is the Co-host of The Ruby on Rails Podcast. Victoria and Will talk to Brittany about the multitude of stuff she's interested in, including Roller Derby, and gives the story of how she found herself co-hosting the show. She says knowing what your brand is and what listeners should expect from listening to you is super important, and she gives her opinion on what it means to be in the Ruby on Rails Community. Shogun The Ruby on Rails Podcast Follow Brittany Martin on LinkedIn or Twitter, or visit her website. Follow thoughtbot on Twitter or LinkedIn. Become a Sponsor of Giant Robots! Transcript: VICTORIA: This is the Giant Robots Smashing Into Other Giant Robots Podcast, where we explore the design, development, and business of great products. I'm your host, Victoria Guido. WILL: And I'm your other host, Will Larry. And with us today is Brittany Martin, an Engineering Manager at Shogun, where she manages a team of Ruby and React engineers. She is the Co-host of The Ruby on Rails Podcast, almost five years running. And she plays roller derby for Steel City Roller Derby under the pseudonym, catch this, Merge Conflict. She is based in Pittsburgh, Pennsylvania. Brittany, thank you for joining us. BRITTANY: I am so thrilled to be on here. I have been listening to Giant Robots for years. So it's an absolute honor to be on the show today. VICTORIA: Yes, thank you so much for joining us. And I met you at RailsConf this year. And, at the time, you had a boot on your foot. So, I have to ask you, are you healed? Are you recovered? Are you walking around again? BRITTANY: This is such a good question. When I was between jobs in March, I was, you know, having these two weeks, I had a whole list of things that I was going to be doing. You know, I was going to train, like, running and whatnot. And I had roller derby practice that first week, and I broke my ankle. And, you know, going into it, I had no idea what a blocker it was going to be. I was like, oh, this is minor. It'll just take a couple of weeks to heal. No, it's been a long process. But I can gleefully tell the listeners that I am out of the boot. I am walking. I am hopefully getting into a sports program next week that will train me up to get back into CrossFit, running, and skating. Though the really funny part is that I currently have another injury which is golfer's elbow. [laughs] WILL: Oh, wow. BRITTANY: Yeah. So I have that from overusing my arms. So I'm a little bit of a mess, but, you know, getting myself back together physically so I can get back on my skates. WILL: So I know it's called golfer's elbow. But did you actually hurt it doing golf, or was it another sport you were playing? BRITTANY: It's so funny that you ask that, Will, because whenever people ask me how I broke my ankle, I can be glamorous and be like, "Oh, it was roller derby." WILL: [laughs] BRITTANY: Like, it's a sexy injury, you know. I have a friend who just broke their ankle because they were dancing down the stairs and broke it, not as glamorous of a story, right? WILL: [laughs] BRITTANY: Golfer's elbow. I literally have no idea how this happened. I've never golfed a day in my life. So [laughter] it's my non-glamorous injury at this point. WILL: Yeah, that's my background, sports medicine. BRITTANY: Oh, great. WILL: So it's interesting. Yeah, golfer's elbow, and I'm like, it's usually not golf that does it. So...[laughs] BRITTANY: Yeah. So I said something to my PT. I was like, "Am I the first person to ever get golfer's elbow from, like, you know, fixing another injury?" And she's like, "Yes. Yes, you are." [laughs] And I was like, oh. [laughter] I really was expecting to get some reassurance that it wasn't me. But hey, what are you going to do? WILL: There you go. BRITTANY: I love the fact that you do love my roller derby name. As you can imagine, it is a beacon for finding the other programmers out on the track because they find it very funny. Nobody else finds it funny whatsoever. And people call me Merge for short, and some people think it's Marge. And I just allow it at this point. [laughter] My number is 200, and its status code okay. When you hit me, I get up okay until, apparently, I break my ankle. So...[laughter] WILL: I love it. Because if you're a programmer, you're like, oh, she means business. BRITTANY: Exactly. WILL: Because merge conflicts...yeah, never fun. BRITTANY: Exactly. VICTORIA: I love that. I love finding other people who work in tech in other random activities. Like, I've recruited people from the climbing gym. [laughs] I'm like, oh, we're climbing together, and, oh, you're an engineer. That's interesting. [laughs] So it's great to, like, be with your community in different settings, so... And you're just so involved in the Ruby on Rails Community. And I'm curious what really got you started into podcasting. BRITTANY: Yeah, that's a really good question. So I'm a former product manager former MBA. So I didn't know how to code. I moved out to San Francisco because I thought that's what everyone did. If you wanted to be in tech, you moved out to San Francisco, and so I did that. And I realized very quickly that it was going to be hard for me to be a product manager without knowing how to code. And so I went to a bootcamp at night, and I became a Ruby on Rails developer. So I wish I had, like, just a really cool story for why I chose Rails. It's literally the framework that was being taught by the bootcamp. WILL: [laughs] BRITTANY: But I'm so glad that it was because I love this community so much. But, you know, when I moved out to San Francisco, I just had my current partner at the time and my dog. I didn't have any friends. And so it was really the perfect time to learn how to code just because I was really able to focus. And I ended up having a lot of long walks at night, like, getting to the train, getting to the bus, and that's really when I got into listening to podcasts. I'm not a huge music person, which is kind of weird. I really...I deeply love podcasts. And so I just kind of glommed on to a bunch of podcasts like Giant Robots, CodeNewbie, Bike Shed. I figured if I listened to all the things that I wanted to be, like, osmosis would just happen, and I would just start learning the things because I was actively learning about how to code. And I thought just listening to those concepts would really help. And really what ended up happening is those people that I was listening to, like, to me, they became celebrities to me. Like, I don't care about regular celebrities. [laughter] I care about people within these communities that I care so much about. And so, you know, a couple of years into that, I was still very much devoted to listening to podcasts. I trained for my first marathon listening to podcasts. And I was listening to The Ruby on Rails Podcast, and, at the time, Kyle Daigle had taken over the show. And he had decided, in order to spice things up on the show, he was going to bring co-hosts on that he was going to rotate through. So, every couple of weeks, you would come on as a co-host, and you would drive the conversation with things that were going on in your life. And, at the time, you know, there wasn't a lot of women, female representation in podcasts. I felt that I was doing interesting things. I was working at a non-profit doing ticketing for the Broadway Symphony and opera, like, in Rails. So I felt like I was always working in Rails, and I thought I could provide some useful insight. So I reached out to Kyle. I must have been very ambitious that day because I reached out and I said, "Hey, how about bringing me on as a co-host?" And he said, "Yeah, absolutely. Like, that would be great." And so I came on as one of the regular co-hosts on The Ruby on Rails Podcast, which I should have been flying high, right? Like, this is exactly what I wanted. I got to become like one of my own celebrities, right? Well, Kyle got really busy. At the time, I believe it's when Microsoft was acquiring GitHub. And Kyle still works at GitHub today. Kyle is amazing. He's their COO now. But the podcast kind of went dormant for a couple of months. It was my big opportunity. I really loved, you know, being on a podcast. I had done a couple of episodes. So I reached out to Kyle and said, "Hey, is there any chance you would give me the podcast?" And he said, "Absolutely." And he signed over everything to me, [laughter] which was really scary because I was taking over a podcast that had been around, at that time, it had been around for at least ten years, hundreds of episodes deep. It was on its own network. It was on the 5by5 Network at the time. So it had sponsors and expectations. And so, really, I had to learn everything from the get-go. Like, I made up my own episode plans. I made up my own questions, like, how to do ad reads, how to edit, how to upload to the hosting platform like; that was entirely on me. And, you know, we can talk more about how the podcast has evolved over those years. But yeah, long story now made short, that is how I got my start in podcasting. WILL: That's actually really amazing that that's how it got started and everything. Let's go back to when you first started. What was your feelings like? You say it was a lot to take on. Can you dig deeper in that and tell us more about that? Because I think I felt the same way. I think we've been doing this for about a year now. It's scary, let's be honest. It's scary jumping on a podcast and sharing who you are and what you're doing. So, can you tell us more about that? BRITTANY: Absolutely. I think one thing is just knowing what is your brand and, you know, what listeners should expect from listening to you because this is a podcast that had been around for ten years. You know, it had changed formats several times. It was an interview-style podcast at one point. At one point, it was a bunch of co-hosts that would just meet every week to talk out what was going on. And so I really needed to take a moment and kind of look over the metrics of the episodes. Like, I have that marketing background. I have that product background. So I wanted to know, like, what's actually working? Like, what do listeners want to listen to? And I also, like, kind of pored through all the reviews of the podcast. I'm like, did people even notice that this podcast went offline? Like, what's the current ecosystem? How many podcasts are out there in the Ruby and Rails space? And so what I started doing is I wanted to create, like, a safe environment in order to start the podcast over again. So what I did is I did interview-style podcasts with my friends, people that would tolerate me, you know, making mistakes, knowing that I was probably...I am a terrible editor. And so bringing those people on to have just genuine conversations with. And then really just tried to pick up the listenership of the podcast because I'm basically waving my arms saying, "Hey, folks. Like, The Ruby on Rails Podcast is back. I'm here as your host. And, like, we are here to stay. Like, I want this to be a mainstay in the community." VICTORIA: That's great. So you started to apply those concepts from your product background. And I'm curious what you found in how the business of the podcast really works. BRITTANY: Yeah, I learned a lot, and we can talk about the transition. So, when I came on to the 5by5 Ruby on Rails Podcast, at the time, this was back in 2018. The podcast was being managed by 5by5, which is, like, a long-standing podcast network. They're still around, but they're much smaller than they used to be. So, like, all of the sponsorship and the episode management was being handled by them. And so I didn't have a lot of insight into that part of the podcast. What I did have insight into is, like, what content is performing well? And what is the audience reaction to what we're putting out there? Like, how is the listenership coming back and whatnot? Now, one thing that did happen over the course of me managing The Ruby on Rails Podcast is we decided to take the podcast independent at one point, you know, 5by5 was starting to wind down. And so, back in 2021, I reached out to 5by5 and said, "Hey, I genuinely really love this podcast. I want to be able to take it to a different platform, you know, have it go independent. But it's really important to me that I'm able to hold on to the current subscribers that I have." I think we all know that, like, if you rebrand something and it's a totally different RSS feed, it's really hard to get people to move over, especially if they're using something that makes podcast listening really easy like Apple Podcasts, you know, you subscribe. You get new episodes, and you just hit play. And so they were extremely willing to work with me. And so, we ended up taking the podcast independent. 5by5 created the hosting platform Fireside. And so we moved the podcast over to Fireside, and that was, like, a very seamless transition. But it was a moment in time where, you know, I was kind of questioning. We're no longer 5by5. It was the 5by5 Ruby on Rails Podcast. What do we call it? And so I genuinely had that moment where I was like, I could be really clever with the name. But then I stepped back, and I was like, no, everyone already refers to it as The Ruby on Rails Podcast. I'm just going to go with it. And so I think that ended up being a good decision. We did change the logo of the show. We kept the same feed. And we had, like, the first episode on the new...we're not even on a network now; we're independent. The first episode of, like, the V2 of The Ruby on Rails Podcast is really what we called it. We just kind of explained the whole move. And I'm just deeply grateful all of our listeners just kind of followed along. And I will say the biggest boon to us moving is that we did get a professional editor. And so, like, the quality of the episodes went up, which is the best money that you can spend. Get yourself a professional editor. I cannot stress that enough. Or you get really good at it yourself. But I know my own skills, and it was never going to be that way. And so we took it independent. And I also decided to do a format change as well because it was a lot to do years of a podcast by myself. It was a lot. So I'm really glad Victoria and Will that you have each other. I think it's really great to have co-hosts. So I ended up moving the podcast. I now have a producing partner, and that's Mirror Placement. They do recruiting for Ruby on Rails, and they are wonderful partners. But I also have three co-hosts that rotate through. I have Brian Mariani, who's a recruiter and founder of Mirror Placement. I have Jemma Issroff, who works on Ruby at Shopify. And I have Nick Schwaderer, who works on Rails infrastructure at Shopify. And that's been great because I rotate through those co-hosts. And I always have fresh content from them. But I also do the interview-style episodes as well, which Victoria was on recently. VICTORIA: Yes. I agree 100%. Having a co-host like Will makes it so much more fun. And I cannot appreciate our editor Mandy Moore enough. And I agree on that advice. And I actually would add when people ask me if they should start a podcast, recommend having at least one other person [laughs] who you want to talk with about that topic for every week. But I wonder, if someone's thinking about starting a podcast, what would you have them consider as to whether or not it's worth it for them? BRITTANY: I recently joined the podcasting subreddit on Reddit just because I was interested to see what kind of questions there were out there. Because when I got into podcasting, I was, like, oh, you just need to have a microphone and a way to record, and you just put it out there, and people are going to listen. It feels very much...like, you remember when, you know, the iPhone came out, and the App Store was empty? And then any app that you made was, like, amazing. Everybody would download it because there was nothing to download. We're now getting to a point with podcasts; there's just a lot out there. My first bit of advice is, something that I said earlier, is make sure that you have an identity around your podcasts. Like, make sure that you are targeting a niche. It's fine if there are other people doing it, but do something that is uniquely you and do something that brings you joy. I really love talking to people in the Ruby on Rails Community. I have a special affinity for people who have never been on a podcast before. It's a lot of work. So it's definitely worth it. I've gotten to meet a lot of my programming heroes because of it. And there are times where I've been very tempted to take a break and be able to step away from it. But, as of right now, it has been a good experience. And what I often say whenever I open up my conference talks is the Ruby on Rails Community is my community contribution because I'm not someone who regularly contributes to open source. And so this is kind of, like, how I give back, and I get to meet a lot of amazing people. Mid-Roll Ad: VICTORIA: Introducing thoughtbot's ongoing maintenance service. Need reliable support and maintenance for your software? Look no further. Our expert team handles upgrades, bug fixes, UI adjustments, and new feature development. And the best part? Our maintenance packages start at just 5k per month for companies of all sizes. From Ruby on Rails to Node, React, and, yes, even PHP, we've got you covered. Trust thoughtbot for top-notch support and optimized performance. To receive a custom quote, contact sales@thoughtbot.com. VICTORIA: And with me here, I have Richard Newman, who's the Development Director on our Boost Team, to talk to me a little bit more about what maintenance actually looks like once you've built your software application, right? RICHARD: Hi, Victoria. VICTORIA: Hi, Richard. You have experience building applications. I wonder if you could describe to a founder who's considering to build an application, like, what should they consider for their long-term maintenance? RICHARD: Well, like you said earlier, part of what you're going for with that long-term maintenance is making sure the health of your project, of your application, is always there. And you don't want to be surprised as you're continuing to work with your users and so forth. And so a number of things that we pay attention to in maintenance are we're paying attention to keeping the application secure, providing security updates. We want to make sure that the ecosystem, basically, all of the tools and third-party services that are tied to your application, we're responding to those sorts of changes as we go along. And then part of it is, occasionally, you're going to find some smaller issues or bugs or so forth as your user group continues to grow or as needs continue to change. You want to be able to respond to those quickly as well. And so a lot of what goes into maintenance is making sure that you're paying attention and you're ahead of those things before they surprise you. VICTORIA: Because what can happen? Like, what are the consequences if you don't do that ongoing maintenance? RICHARD: Well, the security updates those happen across gems and in the platform sort of tools that are there. And so, if you're not keeping those up to date, your exposure, your vulnerability to being hacked, or having a bad actor come into your application start growing on you if you're not doing the maintenance. The other ones that can come up is there's new interfaces that these third-party services...they may be updating their APIs. They may be updating how you're supposed to work with their tool. And so those can occasionally break if you're not paying attention to what's going on or you're suddenly surprised by an upgrade that you have to make. And then, finally, there's this long-term sort of code change that just builds up over time if you're not keeping it refactored for the changes that are upcoming in a language or the gems that you work with. And then, suddenly, after a while, it suddenly gets to the point where you have a lot of work that you might have to do to rehabilitate the application to take on some of the newer features that are being released. And so that makes it that much more difficult, that much more friction about being able to deliver updates for your users or to be able to respond to changes that are happening out there in your application. VICTORIA: Right. So, if you don't have that ongoing maintenance, you could run into a situation where suddenly, you need to make a very large investment and fixing whatever is broken. RICHARD: Absolutely. It's going to be very tough to plan for if you weren't keeping up all the way along and, yes, absolutely ends up being much slower if you have to remediate it. VICTORIA: That makes sense. I wonder if you have any examples of a project you've walked into and said, "Wow, I wish we had been doing a little bit more maintenance." [laughs] And maybe you can share some details. RICHARD: Yeah. We had a fairly large application that involved a number of clinic services. So we had an application that users were going in every day and counting on our fast response. And, over time, we've got surprised by a database upgrade that had to happen. Basically, the database was going to be changed by our third-party hosting service, and that hadn't been tested. There hadn't been procedures in place when we discovered this need. And there was a very hard date that that change had to be done or else the entire application was going to go down. And it came at a very inconvenient time, at the end of the year around Christmas, that we had to respond to all of that. And had we been in front of it and just updated it every quarter and staying current with it, it wouldn't have been nearly the lift that it turned out to be. We were facing a pretty hard deadline [laughs] there to keep things going. It was very, very stressful and disruptive for the team and potentially for the clinics. VICTORIA: Right. And it always happens around a big holiday or something like that, right? When it all comes to a head. [laughter] RICHARD: Absolutely. You want to be in control of the timeframe and not have the timeframe be in control of you. VICTORIA: Right. And if you have a team like thoughtbot supporting you, you can go on your vacation with a little bit more knowledge that if something breaks, there's someone there who can respond and fix things, and you don't have to interrupt your very valuable time off. So... RICHARD: [chuckles] Absolutely. VICTORIA: Yeah. Well, thank you so much, Richard, for joining me today. I appreciate you coming here to talk with us. And we'll talk to you again soon. RICHARD: Yeah, it was a pleasure. Thank you. WILL: I have a question around your listeners. I just want to take a second and just thank everyone who listens to the podcast. We really appreciate you so much, so just thank you, thank you, thank you. Because if you don't have listeners, you don't have a podcast, like you said a second ago. And you went through so many changes. What's been your biggest win, and how do you continue winning with your listeners? And how do you engage with them? BRITTANY: This is a fun answer because, actually, thoughtbot comes into play there. They did not pay me to say this. But one thing that The Bike Shed used to do is they used to go to RailsConf and RubyConf, and they would record episodes during the conference with various Ruby heroes in the community. This is going back to me seeing these people as celebrities. I just thought that was, like, the coolest thing. And, at the time, I couldn't afford to go to conferences like that. So being able to listen to those podcasts and get to hear that kind of content was really important to me. And so, you know, eventually, that stopped being a thing at RubyConf and RailsConf. And two years ago, I reached out and said, "Hey, I really love those kinds of sessions. Is there any way that I could take the lead on bringing those sessions back?" And we did. So it took in the form of a podcast panel at these different conferences where we would bring in different podcasts in the community. And we would have a panel. We would answer listener questions. It was genuinely a lot of fun. So that is a proud moment for me. But it's a proud moment for me because it gave me the opportunity to reach out to podcasts in the community and say, "Hey, we're not competing here. We're friends. I want to record content with you. Like, please be part of my podcast community." And we have never been tighter. So, like, we guest on each other's podcasts. We promote each other's podcasts on like Mastodon and Twitter. And it is just the most lovely thing ever because now we say things like, oh, yeah, like, this podcast, like, that's our, like, sister podcast, or that's our brother podcast. Like, it's so cool that we, you know, rising tide raises all ships. That's exactly what's happening here in the Ruby podcast community. VICTORIA: I like that familial sense within the different Ruby on Rails podcasts, and maybe even Giant Robots is a part of that. Like, are we a cousin or an uncle? [laughter] Who knows? But I was actually there when you recorded the episode live at RailsConf in Atlanta this year. Was that your favorite moment at RailsConf, or was it something else? BRITTANY: Yeah, I would say that was my favorite moment at RailsConf. No matter how many times I meet Aaron Patterson, I am always, like, deeply intimidated by just how funny and intelligent he is. So having that excuse of reaching out to him and saying like, "Hey, will you please be on this podcast panel?" was so fun. I deeply adore Irina Nazarova, and so having her on the panel as well was fun. And then just doing the wildcard of having the audience, like, vote in who was going to be the third panel was truly a risky move, Victoria. [laughs] But it ended up paying off, and it ended up generating some really fun content for us. VICTORIA: That's awesome. And I'm curious, you know, to talk a little bit more about the Ruby on Rails Community. And what do you see is the biggest challenge that it's facing right now? BRITTANY: Oh, I have so many opinions on this. What a great question. [laughs] So I recently put together a talk proposal. It's currently waitlisted at a conference, but it is a talk that I very much want to give. But one project that I would really like to work on is...between, I would say, 2013 and 2015, Ruby on Rails was definitely the number one framework that was being taught in bootcamps. And I'm really curious about what happened to all those people. I'm one of them. I learned Ruby on Rails in 2014. I still believe that I'm in the Ruby on Rails Community, not only for the podcast, but I'm an engineering manager for a company that writes Rails. So I believe I'm very much in the community. I'm so curious. Those people had so much potential of being seniors, principals, staff engineers, founders, engineering managers, architects. What happened to them? And did they stay in our community? And then my second part of that is, what does it mean to be in the Ruby on Rails Community? Like, can you just listen to podcasts and be in the community? Do you need to actively write Ruby? I just find that whole thing very interesting. We're very obsessed with bringing new programmers into the Rails community, which I think is important. But what about the people who we taught Rails and left us? Like, is there an opportunity to bring them back? WILL: It's funny you say that because I wasn't in that year range. I was a little later, like, 2017. And I learned Ruby on Rails, and then I went to JavaScript, you know, React, React Native, but I'm slowly inching back towards Ruby on Rails. My current project, I'm actually able to do some Ruby on Rails. And I'm really excited about it because, like you, that was my first language style that I learned, and I still love it. It is weird, but you always love your first language; I do, at least. So it's interesting that you said that because, yeah, I can say, for me, I'm slowly coming back towards it. BRITTANY: Well, welcome back, Will. We're excited to have you. I know that Node was such a heavy hitter when it came out, and it made a lot of sense. Like, we're going to teach you JavaScript on the front end. Oh, hey, we're going to also teach you JavaScript on the back end. You know, from the business side, I'm so curious whether or not Rails is still, like, one of the top three solutions in order to get an MVP off the ground. I don't have my thumb on that, so I'm very curious whether or not that's true or not. VICTORIA: We certainly still tend to default to it at thoughtbot and to get MVPs off the ground. And we're still building a bunch of products every year with it. [laughs] So, Ruby on Rails and React together, especially if you're trying to iterate very quickly and test your assumptions about what you're building, I think that it's still a really fast and high-performing framework to use. And it's interesting because there's a coding school in San Diego, Codecademy, which is really heavily involved, [chuckles] of course, in the Ruby on Rails Community, and they still teach it in their bootcamp. And one of the reasons they said to me was because it's one of the frameworks that gives you that holistic view of how everything works. [laughs] Like, if you're new to tech, new to programming, in general, it's a very easy entry point to understanding. And I think that, of itself, when you're talking, like, the long-term viability of a framework, being able to hire people who can step in and understand what's going on in your codebase, that framework gives you a higher chance of that. [laughs] You know, that might point to your long-term success, too. BRITTANY: Now, that's a really good point. Going back to the podcast as well, I think one thing that is not very well solved is just being able to make it sustainable as well because there are only so many sponsors out there. And it's really hard to prove ROI from sponsoring a podcast, right? Like, you can put links in the show notes. And you can hope people click on them and they convert. And you can be able to say, "Hey, this podcast is the reason." But I've seen a lot of people start podcasts, and they think, well, if I put a bunch of episodes out and some people listen, then sponsors are going to knock down my door. I'm very lucky that I've had some long-term sponsors that have been able to keep the show sustainable. And I love seeing podcasts that come out of companies, you know, like thoughtbot, where you are being sustained by the company that, you know, is producing it. It's really hard to justify a podcast as a business unless you are already a major celebrity already, right? VICTORIA: Yeah, we certainly don't do it for the money it makes us directly off the podcast. We do not. [laughter] BRITTANY: We do not. VICTORIA: Yeah, I agree with that. And yeah, and even it's interesting as an advertising vehicle or marketing for your company. It can be great because, like, I feel with Giant Robots, we have so many listeners, like, loyal listeners over the years that we have this, like, direct way of communicating with a community that we care about. [laughs] But if you don't have...trying to, like, create that market and create that group of people from the ground up can be really tough. [laughs] And it takes a lot of time, a lot of investment, and a lot of effort, especially if you can't afford a professional editor. [laughs] BRITTANY: Agreed. There's just some cost that I believe, like, the longer I do this, that are just, like, non-negotiable. There are some things that you can definitely have as optional. You know, for me, like, you have to have a good microphone. You have to have a professional editor. I pay for, like, my calendar scheduling software because I want to make that really, like, slick for my guests. Like, I used to...oh, I used to do the emails back and forth of, like, I'm available at Thursday at 2:00 or Friday at 3:00. Like, would one of these work for you? No. [laughs] It's just...that's a rotten experience. For us, we do send, like, a thank you gift after being on the show, which has been, like, a nice add with having a producing partner that will back me on that. And I try to get to as many conferences as possible because I think it's a great vehicle to promote the podcast, but those end up all being optional. And all those things they do cost money. VICTORIA: They do. And it's funny, like, yeah, getting out to the conferences, it's still the number one way to grow things is by meeting people in person [laughs], like, being real and human. BRITTANY: Shocking, right? [laughs] VICTORIA: Yeah. And I'm just kind of curious, like, in terms of how you picture what success means for your podcast. Like, what does that look like in the next six months or even, like, five years of hosting this podcast for you? BRITTANY: Ooh, this is, like, the existential crisis question because I've been doing it for nearly five years. And I think the question is always going to be, you know, like, how long do I want to keep hosting the podcast? I will say the podcast is a positive influence on me in terms of making sure that I stay connected to people, that I keep writing code on the side so that way, I know what I'm talking about. I have this whole imposter thing of, like, what if someone finds out I'm not a Ruby on Rails developer day to day and that I'm, like, actually thinking about business problems; I was, like, an engineering manager? You know, I'm going to get found out, and people are going to unsubscribe. But in all seriousness, I think the success for this podcast is that it can go on without me. It's been around for that long already. And eventually, like, I want to have a succession plan where someones, I will say, like, multiple co-hosts to be able to take it over from there. It'll be rough to watch because, like, I really enjoy, you know, my current era because I feel like the podcast has gone through different eras. I really do enjoy it. But, at some point, it's just not going to make sense in terms of my professional goals. Do you feel the same? VICTORIA: Yes. But we're only a year in. So I feel like I'm still...[laughter] I feel like I'm still new to hosting. And I'm like, oh, I've already recorded, like, 30 episodes or something. [laughs] There's been a lot of change. And we're always thinking about, like, how do we make it better? What do we do? And trying to figure out how do we really get the most out of it for ourselves. But I feel the same way that it's just one of the more fun things that I do at thoughtbot [laughs]. And it gives me that chance to reach out to people and start conversations that I otherwise would not have had. So I really appreciate it. I don't know what you think, Will. WILL: No, I totally agree with you. I love meeting new people. And I love meeting the diverse group of people that we have on the podcast. I love that just, like, how did you get here? Like, what makes you keep at it? Like, you've been at it for five years. What makes you keep at it? Just those questions like that I really love. For me personally, I think that I'm still in the growing phase of podcast hosting. Like, I can get better at this. I can get better at that. What else can I get better at? So I think that's where I'm at in this phase. But, like Victoria said, that's only a year in. It's a different story when you're five years in. BRITTANY: [laughs] It is. And one thing that I will do to make it more sustainable is, you know, like when you're running, you can either be sprinting, or you can be doing, like, a long endurance race. So with the podcast, I will book a bunch of podcasts in one week and say, this is my week to be recording. Like, I'm going to be very heads down on the podcast. I have other things going on in my life, but I'm like, this is a podcast week for me. And so I will record a bunch of episodes. And that essentially gives me a couple of weeks where I can essentially take a break from the podcast. But guess what, listeners? Like, you're still getting new episodes. So you have no idea that I'm secretly taking a break. And I think that has also been a huge help. Odd fact is that the five years that I've been hosting The Ruby on Rails Podcast, I am only missing from one episode. And the reason for that is that when I broke my ankle, [laughs] I called my co-host and was like, "Hey, I'm going into surgery tomorrow. We have this great episode being recorded tomorrow. I need you to take it." [laughs] And so that is the one episode that I am missing from, but I think it was a good lesson for me to know that I can step away and good content can still happen. WILL: That's amazing. That's a pretty good record. [laughs] BRITTANY: Or it might be obsessive, Will. I don't know. [laughter] WILL: Let me ask you this, what does success look like for you personally - roller derby, your full-time job? What does success look like for you in those areas in six months or a couple of years? BRITTANY: Oh, that's a really great question. So I had stepped away from roller derby during the pandemic. And so I absolutely love fitness. I do CrossFit. I have a peloton. I have my own little home gym that I built during the pandemic that I absolutely adore. So, you know, success for me is continuing to invest in that self-care. I want to keep skating just because I'm that person. Everyone came to me, and they're like, "Oh, you broke your ankle. I bet you won't go back to a roller derby." And I was like, oh, you think I won't? You think I won't go back? [laughs] So I'm headed back, but I'm going to be very careful about it. Because I've seen that, you know, your body can break, and you need to give yourself some rest. But to answer, overall, like, I am an engineering manager now, and, you know, my goal is to eventually to get to that director level. And, in some ways, like, I can justify the podcast just because I do get the excuse to talk to people that have the job that I eventually want to have in my career. And so it helps in that regard as well. VICTORIA: I think that's great, and I agree. That's also why I started getting involved in my community a lot, maybe 5 or 10 years ago. I was just like, here's opportunities to show my leadership and see how connected I am with other leaders. [laughs] It helps in that way. And on blading, I actually bought rollerblades recently just to go around the neighborhood. BRITTANY: Yeesssss! VICTORIA: And I got heckled by a woman [laughs] who said...I think she was being sincere, but she was like, "Bend your knees, and it's going to be okay." [laughter] Like, "Wear wrist guards next time." [laughter] I was like, maybe just my face was very try-hard in that moment. Because I have a lot of respect for people who can roller derby and get around on skates that fast. [laughs] BRITTANY: Well, you know what's really funny? (I haven't even talked about this on my own podcast.) is that you know, I'm involved in the Roller Derby League. Obviously, I can't skate right now. And so I needed to find a committee so that I was able to still, you know, provide value to the league. And so, for some reason, I decided that skater resources would be a good idea. So I'm essentially one of the people who is, you know, human resources within the Roller Derby League. And so when there are disputes or questions, or people have hurt feelings, like, they're coming to me, which is, you know, really funny because I do some of that as an engineering manager. So, like, to your point, Victoria, like, you know, I can do growth because they're way more extreme through roller derby, as you can imagine. And, in some ways, it ends up being good practice. VICTORIA: Yes, that does sound like practice for higher-level management decisions, [laughs] so get ready. You're going to have issues and problems, and you're the one to solve it. So... BRITTANY: Yeah. It's not like their problems don't matter. But, in some ways, it's almost like playing with monopoly money because, like, you know, you're not dealing with somebody's, like, livelihood. You're dealing with a sport that they do for fun. Like, trust me, no one is being paid to play roller derby. [laughs] It's a very expensive sport. There's a lot of equipment involved. And, Victoria, yes, you want to wear wristguards. [laughter] VICTORIA: Yes. I learned my lesson. BRITTANY: You write code. You want to wear wrist guards. [laughter] VICTORIA: Right. And yeah, it's funny about things like that. Like, it's still very meaningful to people. Like, when I used to coach kids' climbing competitions, it's, like, the same thing. Like, it's rock climbing, everybody, but some people take it very seriously. [laughs] There's a lot of feelings involved. But, at the end of the day, it's nice to have that practice outside of the pressure of it being someone's livelihood and all of those details. BRITTANY: Agreed. VICTORIA: Well, let me ask you this question. It's one of our favorite ones. But if you could go back in time and give advice to your younger self, what would you say? And maybe it's at the beginning of the podcast or some other inflection point in your career. BRITTANY: That is...oh, what a gift because hindsight is 20/20, isn't it? When I was going through school, I ended up getting a marketing degree because I really enjoyed business. I really liked, you know, the mechanics behind marketing. But, at the time, I had taken a couple of computer classes, and this was back in 2006. And, you know, I thought about double majoring in computer science and marketing. And someone gave me the terrible advice that computer programming was going to go away [laughs], and so it would be a waste of time to get that double degree in computer science. And so, you know, I'm very much a second career developer. Like I noted earlier, you know, I was a PM. I was a non-technical product manager before I learned how to code, and so I learned how to code in my 30s. So I wish I could go back and get into programming way earlier. It would have changed the entire trajectory of my life. But part of me always wants to live out, like, that Black Mirror, like, what it would have been like if I had learned to code so much earlier. Would I have found Ruby? Maybe not. WILL: I totally agree with that because the same story. I remember growing up, and I had a cousin that lived next door. He used to program, and I was just, like, he was a celebrity because I was like, whoa, look what he's doing, and how can you do that? And then I went off to college. Well, I grew up in a small town, so we didn't really have many computer programs. I went to a college, and they said, "Hey, we have this one computer course you can either take it or test out." I was like; I'm not taking it; test out. I want to save that money. And I didn't realize how much I'll love computers and programming until later in life, late 20s, early 30s. And I wish I could have started early, so I totally agree with you about that. VICTORIA: Like, I wish I would have time now to learn how to code. [laughs] Like, I still need to learn it. No, I think that...oh, would I advise? I don't know. You know what's funny? A recent guest said that if that had happened, they still wouldn't have believed themselves [laughs], right? Like, would you really believe someone telling you what to do? Like, you know, you try to make the best decision that you can at the time. BRITTANY: I think it's fun to look back and see all the little things that happened that got you to where you are. So, like, two of, like, crucial things that happened for me. I was in school to become a genetic counselor, and I hated it. And so I had gotten an internship, and, like, that internship changed everything because it was like a day in the life as a genetic counselor, and I really did not like it at all. And so, I ended up dropping all my classes and moving into the business school. And so that was one thing that happened. And then the second thing is, you know, I was working at a cowboy restaurant. [laughs] It was ridiculous. And I was getting ready to graduate school and just absolutely terrified about not having a job. I ended up getting this table of this company that was, like, having a business meeting, and we ended up chatting, and they were so wonderful. And they left me their business card, and, like, that ended up being my first job. It's just the little micro-decisions that you make that, like, change your entire trajectory, which is really so cool. So you end up not really regretting anything, but you always just kind of look back and reflect, and you're like, what if I had given that table away? Or what if I hadn't been ambitious and, like, tried to get that internship? So just everything's an opportunity, right? WILL: Yeah, I totally, totally agree with that. So you do roller derby, CrossFit, marathons, coding, your podcast. So you do a lot of self-care, which I don't think, especially in the tech world, we do enough self-care. I know I don't. I am horrible at it, trying to get better. What's your wind in your sails for that? Like, how do you keep going? Like, how do you stay disciplined with that? BRITTANY: I think, for me, I feel better when I move my body. I make better decisions. I am more patient. I need to work out earlier in the day. Like, I am a morning person, and so it makes me feel good. And so then I go into work in a good mood. And I deal with people day to day, right? Like, I manage ten developers. And so it's also something that I can use to connect with my team as well. A lot of them also like to do physical things, and so that works out nicely. In terms of nutrition, I definitely could be better. But I will say my partner and I take turns meal prepping our lunches. We both work from home. And so being able to, like, in between meetings run over and grab a box of actually good food to be able to eat lunch. We do, like, a meal service at night as well. I don't know, like, you need to look out for you. Because while the belief is that other people are also looking out, nobody's going to look out for you like you are. And so you have to prioritize self-care and just making sure that you're getting those moments. And I agree with you, Will; sometimes, I'm absolutely terrible at setting up those processes so that way you don't fall through. VICTORIA: I think there's a book that makes me think of it called, like, The Subtle Art of Not Giving a F*ck. [laughs] BRITTANY: Yes. VICTORIA: Yeah. BRITTANY: Yes. VICTORIA: Yep. And I think that's part of it, too. Like, there's a lot of pressure to be so high-performing and to do all the things for your family, and for your work and your personal life. But, at the end of the day, it's also okay to just sit around and do nothing [laughs] and, like, relax. BRITTANY: Yeah, I've watched a lot of Drag Race, a lot. [laughs] VICTORIA: Oh, awesome. Yes. What's your favorite season? BRITTANY: Oh, season six, I would say. Season six is just so good. Are you watching All-Stars? VICTORIA: I'm not right now. I'm actually...I usually binge-watch it at random times. So I'm not really caught up. But I have met a few of them at drag shows. I think I've met Milk. Is that [inaudible 44:27] BRITTANY: Oh, wow. What a queen to have met. VICTORIA: I know. BRITTANY: That's amazing. [laughs] VICTORIA: That was actually a very funny story. I'll tell you another time. [laughs] But yes. BRITTANY: But honestly, like, Drag Race actually relates to engineering management for me because, you know, at my last job, I had two developers that I was struggling to connect with. And I realized that after stand-up, they were staying behind to talk about Drag Race, and I wanted to connect with them. And I was like, oh, I'll check out a couple of episodes and became so deeply addicted [laughs] that, like, I surpassed them in how much I loved it. So, like, it is a fun, like, I've always thought about giving a conference talk where, like, each report that I have, like, one crazy thing that they do...well, not crazy but, like, one, you know, passion that they have and, like, trying it just to have something to relate to. Though I will say, I did manage somebody who really liked to jump out of planes, and that is just not in the cards for me. VICTORIA: I love that too. I like when someone is really passionate about something. I'm like, okay, I'll give it a chance, at least once, you know. But I have some friends right now who are into freediving, and I'm not convinced [laughs] that I want to go try to hold my breath underwater. BRITTANY: What in the world is freediving? VICTORIA: It's diving underwater without oxygen. BRITTANY: No. VICTORIA: Yeah. Yeah. BRITTANY: That's a big nope for me. VICTORIA: And, like, hunting fish. So, like, they catch tuna and stuff. They're down there pew-pew and making sushi when they get back. BRITTANY: Well, that actually sounds wonderful. But -- VICTORIA: Yeah, I'm like, I will eat this. I will eat [laughs] whatever you catch. BRITTANY: Yes, that's fair. VICTORIA: Yeah. Like, I'm into the results but not...I might try some of the, like... a lot of it is, like, training your breath and being able to hold your breath and to stay calm because that's really the biggest problem. [laughs] I do rock climbing. I think that's enough. Like, that's -- WILL: [laughs] BRITTANY: That's pretty badass. VICTORIA: Yeah. [laughs] WILL: Yes. BRITTANY: That is a very cool sport. VICTORIA: Yeah. And, actually, you're mentioning how it was, like, you worked at a cowboy restaurant, and that was how you got your first connection to your job. And, like, I would go up to, like, my college climbing wall and be, like, I'm a rock climber; you should hire me. And [laughs] through that connection, I got my first referral to my first job in DC. And so, basically, my whole life revolves around it. [laughs] Nothing would happen without these little connections that you make. I'm curious, Will, if you had a pivot point like that you can tell us about. WILL: It was probably getting to tech because it was more of a hobby, and sometimes it's still a big hobby for me. So I will say either getting into tech or working out. So I try to work out with friends. So I used to play football. Everything was a group workout. So after football, it was very hard for me to work out because it was always a group workout. So after many, many years of finally realizing that, I try to work out in groups, with friends, and stuff like that. So that's probably the biggest thing for me is, like, working out in a group and having someone to hold me accountable. BRITTANY: I love that. That's one reason...so I used to be a fitness instructor. I should reveal that as well. I used to be a BODYPUMP instructor. And the reason for that is just, like, again, I thought people that were fitness instructors were just, like, celebrities and absolute badasses. And so, I used to only go to group fitness class as well because I needed that accountability. And so, yeah, there's definitely days I wake up where I absolutely do not want to do anything. But having that accountability, it's just really awesome, and really, it makes sure that you follow through. VICTORIA: That makes sense how you've practiced your voice and why your podcasting voice is so strong [laughter] because you're a fitness instructor. That's what is starting to add up for me. [laughter] BRITTANY: You know what? The biggest challenge of being a fitness instructor is that they would send me the routines, and I would have to memorize them. And being able to memorize like, oh, I'm going to squat on the fourth count. And I'm going to do a clean and press on the eighth count. Oh my God, is that an algorithm -- WILL: Yes. BRITTANY: You know, for a pro...and I was like, is there any way that I could somehow automate? Like, part of me wanted to game it. I'm like, how do I game this so I don't have to spend so much time trying to memorize it? I mean, it was truly, truly challenging. And it was probably, like, the best brain teaser that I could have been doing because you're essentially putting on a live performance while working out. And everyone needs to be able to follow you and feel encouraged by you. It was just...it was a wild time. WILL: [laughs] VICTORIA: That sounds very demanding. Well, coming up to the end of our time here, is there anything else you would like to promote today? BRITTANY: Ooh, no. We're currently not hiring at my job. Normally, that is something that I would promote. I would say if you are interested in checking out my podcast, it is The Ruby on Rails Podcast. We have plenty of things on there that are not Rails-specific. We've had conversations about, like, what's it like to get stock options at a company? What does the recruiting landscape currently look like? And then we also have, like, deep topics about, like, what's currently being merged into Ruby Core? So, really, we have a wide variety of topics. So, if you find my voice somewhat pleasant, come on over; we'd be happy to have you. And, of course, you can listen to Victoria's episode, that will be linked up in the show notes. But this was such a pleasure. It was great spending time with you both, Will and Victoria. WILL: Yeah, it was great. Loved chatting with you. VICTORIA: Yes, thank you so much for joining. This was super fun. You can subscribe to the show and find notes along with a complete transcript for this episode at giantrobots.fm. WILL: If you have any questions or comments, email us at hosts@giantrobots.fm. And you could find me on Twitter @will23larry. VICTORIA: And you can find me on Twitter @victori_ousg. This podcast is brought to you by thoughtbot and produced and edited by Mandy Moore. Thanks for listening. See you next time. ANNOUNCER: This podcast is brought to you by thoughtbot, your expert strategy, design, development, and product management partner. We bring digital products from idea to success and teach you how because we care. Learn more at thoughtbot.com.Special Guest: Brittany Martin.Support Giant Robots Smashing Into Other Giant Robots