Startup to Last

Discover the art of recruiting beta testers and the key components of a successful beta program. Learn how to identify ideal users, design your program, and where to find potential testers. The discussion highlights innovative strategies in the health insurance space, covering the importance of personalized engagement and aligning incentives. The hosts share insights on building stronger connections with beta users to enhance feedback and product development. Explore branding essentials that can elevate your startup experience!

This episode ended up being a brainstorming exercise on how Tyler can increase the acceptance rate of his job offers at Less Annoying CRM. Takeaways include:Survey candidates after they either accept or reject to learn moreWhen someone says no, ask why they're saying no. That might lead to some really quick problems you could solve.Look at this from two lenses:Controllable rejections - there’s a way you could’ve changed this outcome. Uncontrollable rejections - there's no way you could've changed it. Even if it's uncontrollable, that doesn't mean there's no action you could've taken.You probably could have figured this out earlier in the interview process, and just stopped interviewing them because they were never going to accept anyway. Understand why people accept your offerThis can lead to some of the best insights on the value propositions that you need to focus on more with future candidates.Highlight your differentiation throughout the interview processMake sure your candidates understand why your workplace is unique and specialYou can do this at every touchpointWhen you make an offer, show them your excitedMake a personal call or send a personal noteHave other people at the company reach out after we give an offer to encourage them to acceptDon’t be afraid to share your excitement with emotionTry making the offer in-personYou could have them come into the office for a final meetingOr you could go to themInvite questions and concerns before a final decisionOffer to go out and meet them and talk about stuff after the offer.Consider whether your acceptance rate is good enoughMaybe it would be better to focus on more applicants instead of increase the conversion rateMake the written offer special Make the offer letter personalSell the role and company instead of just explaining what the offer is. Answer the key questions about total compensation and benefitsBefore you make an offer, find out where the candidates standsBefore you stop the final interview and move to offer mode, spend some time with the candidate and try to pull concerns out, pull anxieties out, pull out what might make them say no. Then address the issues before you make an offer.Question examples:“If you're not working here five years from now, what's the most likely reason why?”“If you were to decline our offer, what would be the most likely reasonWhen you are the employer, there’s a power imbalanceKeep this power imbalance in mind to avoid false signals and to make sure your candidate is comfortableIntroductionTyler: The topic for today is basically flipping interview advice on its head, and saying normally it's assuming that the company is in the driver's seat and has all the power. What I want to talk about today is after you get to the point where you know you want someone, well or before that point, but what can you do to really maximize the odds of someone actually accepting one of these offers. We have a coding fellow, which is where we teach people to code, we have two different internships, and we have a full time position we're recruiting for right now. It really, really sucks when you find the perfect person, you give them the offer, and they decline. I just want to avoid that if I can.Rick: Yeah. Well, before the show I asked you I think what your acceptance rate was currently, can you share that?Tyler: Yeah, this is kind of back of the napkin because we don't have a real applicant tracking system for this, but I would guess it's about 75% probably say yes, and 25% decline, would be my guess. More people decline earlier, but I'd say if we give an offer, some people bow out of the process before this, but if we give an offer, I'd say we have about 75%.Rick: Cool. It sounds like what you want to focus on is how to increase that 75% up to a higher rate.Tyler: Yeah. Absolutely. And I think there's other benefits to this too. It's sort of like the way a good sales process for a company is going to lead to better customer retention also. This is the first impression for a recruit, and we want to build momentum that carries all the way through to after they start.Rick: Okay. All right. Well, I guess, what would be success for this conversation?Tyler: Yeah, I mean, what I'm looking for, I think, I mean ultimately the vague version of this is I just want to get people to actually say yes when I give them job offers. Specifically, I think I'd love a couple tangible takeaways or, not even... just ideas. I feel this is like a brainstorming thing where it's like maybe we can come up with five or ten things I can try, and maybe I'll actually actually try three of them, and one of them will work. But things I can actually do to just do more than whatever I'm doing now, which might be, in some ways, the bare minimum to get people to say yes.How the interview and offer process works currentlyRick: Well can you talk about what you're doing now?Tyler: Yeah. I'm inclined to break this into two categories. One is what's the whole interview process? Because that's leaving an impression on the person, and then there's the actual offer itself. I'm probably really bad at the offer itself. That's probably like the low hanging fruit here. But I'm happy to start at the beginning if you think that'd be helpful.Rick: Totally up to you. We can dive in right to the offer, how you're positioning that, or you could add context about how you're going about this.Tyler: Okay. Let me add a little context, but let's start by talking about the offer just because I think there's the most opportunity to improve there. We go and recruit mostly at schools, but sometimes through LinkedIn, or whatever other channel. The general process, it depends on the job, but it's something like a phone screen followed by, well sorry, they apply with a writing sample and a resume, we do a phone screen, then we bring them in for an in-person. The in-person interview is pretty long. And one of the reasons for that is it's like half us interviewing them, but half us trying to show them they would like it here. Which is easy for college students. With an adult, it's a little harder. Everyone wants different things. College students don't have a very refined idea of what they want. We play a board game with them, and give them free food, and they're like, "Oh great." But it's about a four-ish hour in-person with about half of that being us trying to make them think it's a cool place to work. Normally there's maybe let's say a week, or two, or three where we're finishing all those in-person interviews and we give the offer. What we do for that right now is I call them up. One thing I'm interested in your thoughts on is should it be me, should it be the person's direct manager calling them, but I call them up. No one ever picks up their phone, so the options are leave a voicemail, a vague voicemail that's like call me back or just give them the offer in the voicemail. I've dabbled with both. Right now I'm of the opinio...

The discussion dives into the concept of Minimum Viable Products (MVPs) and explores unique strategies such as the productized service and skateboard approaches. The hosts emphasize the importance of validating ideas through MVPs and the distinction between an MVP and a Minimum Sellable Product (MSP). Real-world experiences highlight the significance of customer feedback in shaping product features. They also share insights on balancing risk with learning and the effective use of email for simplified business solutions.

This episode ended up being a brainstorming exercise on how Tyler can increase usage of  Less Annoying CRM’s customer referral program. Tyler may focus in the following areas: Trying to increase usage of the existing referral program by driving more awarenessTrying to capture more information from signups to determine if they were referredTrying to repackage the referral program to make it more transactional.Takeaways include:It’s important to have a remarkable product experience (that people want to talk about) before you focus on referralsDecide what the objective of your customer referral program is upfrontFor example, is it to create leads or paid signups?It’s hard to create a customer referral program for products with long sales cyclesIf you have a long sales cycle, consider creating or packaging a mini-product that is more transactional in nature to make it easier for your customers to refer (e.g. Hubspot’s website grader)It’s hard to incentivize referrals on a low-ACV productThis is especially hard if there is also a long sales cycleConsidering gamifying and /or tieing referrals into product featuresThink of your customers referral program as a product that requires its own product / market fit.Consider the size of your market (customers and their potential referrals) and how to build the right product for both partiesOnce you think you have a solid referral program product, make sure your customers are aware of itBe careful, you don’t want to be annoying or spammyConsidering marketing it passively as part of larger “join the movement” community buildingWith thoughtful design, you can do this in passive sections of your newsletters, emails, website pages and app pages. (But, don’t be too annoying)Morning Brew, a daily newsletter, provides a good example of an awesome referral program.They've actually written a blog post about it.IntroductionTyler: We're framing it as, how to structure a referral program. But let me dive into why I'm thinking about this.Less Annoying CRM, my business, is currently at about two and a half million dollars in annual recurring revenue. We're growing about 20% per year. I'm happy with both of those numbers, but every company obviously wants to grow, at the very least continue growing and maybe even increase growth. We have not had a lot of success with a lot of marketing things we've tried. One of the reasons for this is totally my fault that I refuse to do certain things. I don't want to do retargeting advertising because I think it's a privacy violation. Anything that's not permission marketing, I'm pretty much opposed to. Also, it's just not one of our core competencies, and because our price point is so low, we don't have the type of budget to compete with other companies on marketing. As a result of that, the way we grow is almost entirely through word of mouth, which is awesome because it's free, it aligns what we're doing with customers. I really like word of mouth growth, but the downside is we have no control over it. I think that's... Would you agree that's true with most companies, that you just cross your fingers and hope word of mouth happens?Rick: Yeah, I would say so. It's definitely one of those voodoo marketing tricks versus a systematic levered sales approach.Tyler: Right? Word of mouth is a big topic. Making the product better, for example, maybe is one way to help with it. That's not what I want to talk about today. What I want to specifically do is say, in as much as we can control word of mouth growth, well, A, we have to be able to track it in order to do anything with it, and B, a referral program is one of potentially many ways to increase word of mouth growth. That's what I want to talk about. Historically, what we've done as a company is, we've offered a deal. It's basically the Dropbox deal, which is, anyone of our customers who refers someone else, that other person gets an extra free month of their free trial, and the person who did the referring gets a $10 credit. A free month themselves.Rick: Give one get one.Tyler: Give one get one. A pretty classic approach, it's worked plenty of times before. Unfortunately, not many people actually use this. Anecdotally, we have quite a bit of reason to believe that lots of people... almost all our growth comes from word of mouth, but the vast majority of that, I would estimate it at about five to 10%, actually uses the referral program. Which is not great because it means we can't track it, we can't tell what's working, we can't experiment very easily. Basically what I would like to talk about today is, how do we offer some kind of referral program that gets our users, when they refer someone, when they do the word of mouth thing, the person who's signing up actually uses a link that tracks back to... Or maybe that's not even the way to do it, but that one way or another we can track it back to the person who did the referral. This might involve giving incentives, it might be restructuring how the technology for the link tracking works. I don't know, but that's the basic problem I'm interested in talking about.Rick: Yeah. Recapping, I want to make sure I got this. You've got a couple of challenges. Well, you've got a great product that people want to talk about, that's the good thing.Tyler: Yeah, that's the good thing.The challenge of low ACVsRick: You know that that's happening, you just don't have control over it. One constraint you have is that you have a low ACV, which means you can't spend a whole lot of money on this. I think the bigger constraint though is your philosophical constraints that you're placing on yourself that don't allow you to engage in some of the marketing activities that actually do give you control over this in terms of data collection.Tyler: Fair. Maybe we should talk about this because it's a case by case basis I guess.Rick: Yeah. I think it's hard enough to control marketing on a low ACV by itself. Then when you add, "Oh I'm not going to do that-"Tyler: Sorry, ACV is annual contract value, right?Rick: Correct. Thank you. Annual contract value, which is... Let's just talk in, it's $10 per user per month. With that amount of money, you don't have a whole lot of money to spend on advertising or anything like that. Then on top of that you're saying, but I wouldn't even be willing to do that if I did have the money because I don't believe in it.Tyler: That's one of the reasons I'm trying to constrain to say, there is a whole range of topics about marketing that we could be talking about. But just to keep this constrained I'm saying, people are already doing word of mouth like referrals. I want to be able to track it and consider ways to specifically enable them. One of the things I love about word of mouth is that the customer wants to refer people to us. Everyone is aligned here. I just want to empower them to do it and...

In this episode, we discuss how to reset expectations with stakeholders when things change. Rick shares a challenge he is facing at one of his companies. While we worked through a specific situation, the general concept applies often. Here’s the general framework that emerged:Clarify what needs to change and whyFrame the problem(s) thoughtfullyIdentify the stakeholders and where do they standIdentify who has decision-making authority and who can be an allyDecide who to talk to first and iterate from there as a teamBe open to feedbackGet everyone aligned and move forward togetherBe aware of fundamental differences; these may require you or someone else to leaveTakeaways include: Change happens all the time and resetting expectations is critical when it happensSome companies die because they never change their expectationsWhen you're going through change, the minimum time investment isn't enough. You have to talk a lot moreStart with the problems, but be thoughtful about how you frame them so that they're generalized problems that don't cause defensivenessAs a leader, people don't see the world like you do. Your job is to get them to see it like you do, and that takes communication and it takes patienceIt is critical to get everyone to see the problems and talk about the problemsWhen you can talk about the problems because they're emotional, you can't talk about the solutions and get on the same pageWhen there is a fundamental disagreement you can’t get over, someone has to go (and it may be you). Get aligned on fundamental values and expectations before forming new partnershipsThe problemRick: In life, change happens all the time. That's especially true in the workplace. Once you've been in business for more than a couple of years... even in the first year... lots of things that you thought were true are no longer true, and you have to change your mindset around what the truth is and what's going to happen next as a result of that. When you're on your own as a solo entrepreneur or you're an early founder, you just have a couple people that are all working pretty well together. It can be pretty easy to make those changes happen because the people in charge are able to make the decisions necessary to change their expectations. When you grow and you have multiple hands in the pot at different levels and it's been a longer period of time investment, you get to this place where resetting expectations is critical when a change happens, but it gets a lot harder. It gets a lot more emotionally complex. It gets a lot more complex just from sheer volume.Tyler: Different stakeholders who all want different things and they think they know what you're doing and things change.Rick: Multidimensional complexity increases over time. This applies to employees, partners, board members, investors. Even at home, when I was thinking about how to frame this problem I was thinking, "Well, this a Sable and Rick..." Sable is my wife. We deal with this constantly, especially in our first year of marriage where we're trying to talk about when do we have kids, what's our budget for certain things? I got fired a week before our marriage from my CEO job. It's one of those things that's like that had to go through a lot of expectation changes. Mostly, what I want to talk to you about is dealing with this at work with the stakeholders that you deal with, specifically at a nonprofit. At GroupCurrent, we focus on helping member-based groups reach sustainability. Most of these groups are nonprofits. By design, most of our customers or nonprofit customers come to us because they've not been successful sustaining themselves. I don't want to say it's a shit show, but it's not a good situation.Tyler: To clarify sustaining themselves, you're saying they start out where they're getting donations from various places but it's a one-time donation. They can operate for a while, but what they want is an actual business model that they can count on, and that's where they come to you to help with.Rick: Yeah, and donations can be sustainable if you have a way of predicting them and continuing to receive them. When we starting GroupCurrent and deciding whether or not we wanted to be in this business, the thing that got me really excited is I discovered this problem that nonprofits often face, and it's not too different from a lot of founders... serial entrepreneurs, in my opinion. The situation is called the organizational starvation cycle. Some people call it the nonprofit starvation cycle, but I like organizational because I think it applies to more than just nonprofits. It starts with some unrealistic expectations from founders. In the nonprofit world, founders are called funders because generally the founders just provide the money and some guidance at the board level. They don't do the work. A lot of times, what they do is they hire a managing director or bring on some fellow board members to help run it, and they have super high expectations, unrealistic expectations. Those people that they hired feel a significant amount of pressure to conform to those expectations, which leads to either overworking, which leads to burnout, or it leads to fudging certain accuracy of things, whether it's maybe omitting when it should be said or rounding up when it should be rounded down. I speak to this stuff sensitively, because it is sensitive, but it leads to bad behavior to meet those expectations, which in turn leads to more unrealistic expectations because you're not dealing with the problem, which is unrealistic expectations. This cycle typically continues from the early days until it reaches a breaking point, which one of two things happen. Either there's no money and management gets fired and the nonprofit gets into this zombie land of, "What do we do next?" Maybe they shut down. Most of them just kind of live without doing much. Or the management goes, "Screw you guys. I can't do this anymore. I quit." There's some actual good things going on, but no one there to do the things anymore. To be successful at GroupCurrent, our clients are going to come to us because they've been in this situation, which is extremely complex emotionally. You've got founders who put a lot of money into it. You've got former people who have worked at the company who probably didn't feel like they were treated the right way. It's extremely complex. In order for us to be successful, we've got to be really good at coming in and resetting those expectations and getting all the stakeholders... the founders, the board members, and the employees that are currently working there, any current donors or community partners, any customers... on the same page with what to expect going forward. Those expectations could be mission, vision, values. It could be business model. It could be, "Hey, board members, you've got to start doing work now. You can't just sit." Roles are changing. We're dealing with this with one of our clients. We're very happy with our customer. This isn't a talk about how much the situation sucks, it's just there's a reality of the situation where the organization has gone through different renditions and it hasn't gotten yet to that place of sustainability. And it's not there yet, even with the work that we've done so far. I guess... go ahead.Tyler: I was just going to say I like this topic because we're going to talk about it specifically in your case. But this applies very much to the topic of...

Here’s what you should know about Rick:Born in Raleigh, NC and grew up in Morganton and Charlotte, NCWent to college at Duke UniversityMajored in Economics and Computer ScienceWrestled at DukeMoved to Park City to Ski bum in after graduationMet Tyler at a startup called Zane Benefits (which is now part of PeopleKeep) in 2007Became the President of Zane Benefits after a mass layoff in 2008Bootstrapped Zane Benefits to $4+ million in annual revenue in 2013/2014After a regulatory threat in 2013, launched a new business called PeopleKeepRaised ~$3M in venture capital to finance thisWrote a book in 2014 which was published by WileyMerged Zane Benefits with PeopleKeep after confirming the legality of PeopleKeep’s approach and reaching product market fit in 2018. Milestones included:$120K in monthly recurring revenue (MRR)Profitable unit economics50+ user NPSLow churn for very small business segmentNumerous customer growth and product expansion opportunitiesWas fired by the board in October 2018 when unable to align on long term compensationFounded LegUp Ventures in May 2019, which owns and operates companies that empower underdogs. Current ventures include:GroupCurrent, which helps member-based groups reach sustainabilityRickLindquist.com, where Rick writes and consults on various topicsStartup to Last, this podcastLikes:Physical fitnessContinuous improvementSustainability (i.e. balance)Dislikes:BulliesVictim playingIntellectual lazinessEntrepreneurial beginningsTyler: Can you just kind of give a little background on how you got into the startup space, entrepreneurship in general?Rick: Well, I guess I do kind of have that story of always being a little entrepreneurial. I had lemonade stands.Tyler: You did? At what age was your very first venture?Rick: Four or five. Yeah, I did the lemonade stands. I took it very seriously. I mowed grass. I tried a lot of different things. I always thought about it. I read business books when I was in high school, entrepreneurial books. I always knew that was what I wanted to do, but I didn't know what my path was. I thought it was something that ... The story I like to tell is, my dad is a lawyer, which is kind of a sole proprietorship in a way. You're a partner in a law firm and you do actually have to produce for yourself. And then my grandfather owned an ACE Hardware store, True Value Hardware store. So I witnessed a lot of entrepreneurship growing up, but my dad always hated his job. He's a litigator and he always had to fight with people for a living. So I was really scared to go to start working because I thought I'd hate my life. I thought that's what everyone did. So I was born in North Carolina. My parents got a divorce at a young age. So I moved all around North Carolina. I think I lived in, like, 17 different houses. I never had that one house. In fact, living in Utah, the Park City area, that's the longest time I've ever lived anywhere. College and majorRick: And so anyway, I ended up going to Duke for college. I graduated in 2007 and had no idea what I wanted to do.Tyler: Well, let me stop you for a second. So what did you major in?Rick: Economics and computer science.Tyler: So you had an entrepreneurial spirit before college. Did that inform what you majored in or anything like that?Rick: Yeah. One thing that I think you'll learn about me is, I'm generally open to anything but, once I form an opinion about it, I form a pretty strong opinion about it. So I actually did not declare a major until the end of sophomore year. I took just about every 101 course at Duke, including political science and I dropped that class midway through and had a really big blowup with the professor. I hate political science classes. They're too political.Tyler: Who would've thought?Rick: Yeah. Who would've thought? So I knew that I was interested in economics. I knew that I was interested in computer science. So those were my first two if I had declared freshman year, but I wanted to see what was out there. And then they were the most practical. One was learning about how money works and the other ... and people work and markets work, and the other was how to build things, I thought. And then I realized, computer science is actually a bunch of theory and bullshit. And I think I had two programming classes and they were my favorite classes at Duke.Tyler: Yeah. I mean, all college professors are theorists, right? So in a sense, every major is theory.Rick: Yeah.Tyler: Anyway.Rick: Yeah. So I did a lot in college. I wrestled. I was in a frat. It was an atypical frat, but still a frat. I did student government. I did a lot of different stuff. By the time I graduated, I was pretty burnt out and so I remember everyone just doing investment banking interviews and I went through a couple of those and I was like, "I cannot do this. I could not move to New York and work with these guys. I need a break." So I decided to move out to Park City to ski bum. Called my dad. He basically said, "That's cool, as long as you're off the payroll." I think he gave me until July to move out and I basically just came out here expecting to ski bum. Unlike you, who came for a job.Ski bumming to startupTyler: A job. I never heard of Park City, nor had I ever skied before. But you knew what you wanted to do here.Rick: Yeah. So my grandfather bought a condo out of bankruptcy in the '80s with an ownership group. So we always came out here for a week to ski. So I was very familiar with the area and I always heard my dad and my grandfather and people talking, like, "I wish I had taken a year off to go ski bumming." So I called them out on that and I took advantage of it. But I got out here, I'd carpet clean in the mornings for a carpet cleaning company locally and then I was a bellman at a hotel called Park City Hotel. And then sometime in November ... I got here in July, and sometime maybe in November that year, I met a headhunter who was recruiting for this startup called Zane Benefits. They had just raised a $3 million series A. And I was driving this person around or it was something like, "What are you doing? You have a Duke degree and you're carpet cleaning and driving people around?" I said, "Yeah. I'm serious about ski bumming." So anyway, I ended up taking a job there because I got really interested in the problem. And I came on as an entry level sales rep and that was my first professional, what I would call my first professional job.Tyler: Because you didn't do internships or anything like that, right?Rick: My internship ... So one summer,...

In this short bonus episode, we talk a bit about why we started this podcast and what we hope our listeners can get out of it

This episode ended up being much more about how to increase workforce diversity than how to hire interns. Here’s a quick rundown: Tyler and his team at Less Annoying CRM want to increase diversityThey primarily source candidates via their summer internship programTyler and his team have had great success at WashU with this modelHowever, this has led to a lack of diversity across his 17 employees (~50% went to WashU)Tyler wants more internships to come from schools other than WashUDespite effort, Tyler has not been able to replicate the internship funnel at other schools in MissouriE.g. He’s tried recruiting via career fairs, by connecting with professors, and by partnering with student groupsTyler pointed out that WashU is successful is due to the numerous former WashU graduate success stories that currently work or formerly worked at Less Annoying CRMI.e. They have product-market fit at WashU for their internship offeringHowever, at other schools, they can’t even get students to applyI.e. They don’t know if they have the right internship offering yetRick recommended Tyler focus on customer development to learn more about what the students at these other colleges are looking forTyler realized that creating diversity is really hard, and focusing on small wins initially is keyTakeaways include: Internships provide a safe way to hire because they allow you to work with someone temporarily before you extend a full-time offerSummer internships, by their nature, discriminate in favor of privilegePrivate schools have a culture that encourages summer internships; Public schools don’t seem to have this same focus.One challenge is that college students, privileged or not, are not very responsiveWhen working to increase diversity, focusing on small wins up front is key. Once you get your foot in the door with a new segment, it gets much easier from there.The problemTyler: All right, let's dive into the topic for today. So this one is mine. So basically we're going to talk about how to recruit interns. And I can give a little background on where I'm coming from with this topic. Basically at Less Annoying CRM, so we have 17 employees, but we've hired significantly more than that in total because every summer we have about 10-ish interns, or coding fellows, which coding fellows and interns are about the same thing here. Tyler: Basically college students who come for the summer. We've had a lot of success with this. It makes hiring really easy because you get to take risks on people kind of and bring in a bunch of people. And then if someone's really a perfect fit, give them a full-time offer to work here after they graduate. So have had a lot of success with that. Really enjoy it. And I kind of have a system worked out, which maybe one thing we should talk about today is just what's currently working. Like Rick, you went to Duke, I went to WashU. That type of place has an intern culture. Students are planning on applying for these, it's expected. Other universities in the area don't have that culture. And we've struggled to get students interested in it, which is kind of counter intuitive because they're schools where the fact that they're paid internships and it's a really great opportunity. You'd think it'd be even more appealing to someone who's not going to as top tier of a school. But the reality is we really struggle to get anyone from those other schools even to apply. So the results-Rick: Sorry, what are they doing instead?Tyler: Yeah, it's a combination of things. Part of it is a lot of these schools, people aren't full-time students as much and so they're not off for the summer in the same way. So that's one challenge. And then the other thing is, I think if you're going to a $60,000 a year private university, probably you come from wealth and probably you kind of have options. And you're like, "I'm going to dabble and try different things and see where my life takes me." If you're going to, for example, the local public university, UMSL, University of Missouri-St. Louis, still a good school. But if you go there probably you're like, "I need a job out of this." And you're majoring in whatever you're majoring in and you're not looking for random other opportunities that aren't specifically in your field.Rick: Sorry, I interrupted you when you were describing the problem. I'll let you finish that.A lack of diversity, starting with internsTyler: Yeah. Okay. Sorry, I'm rambling here. I'm basically done. But basically we have a model that works for hiring interns at WashU. We don't have a model that works elsewhere and the result of this is our employee base lacks diversity in any number of ways. First of all, there's kind of socioeconomic diversity of only rich kids go to WashU. And then also WashU has its own diversity problems in terms of race, in terms of gender, at least on the technical side. So we're not getting a very diverse applicant pool because of the way we're recruiting interns. So I'm interested in discussing how can we go out and attract interns from other universities that maybe don't have that strong of an intern culture.Rick: Got it. So diversify your interns?Tyler: Yes. Exactly.Rick: The problem is you lack diversity with your interns, you've been trying to increase that, you haven't been able to for a number of different reasons, which we'll probably go into later. I'm very interested in what you're... I think you're right. I think it should start with how you do interns. What the intern period is, what you're paying, what you're offering and what's going well so far with those.How Less Annoying CRM does internshipsTyler: Cool. Okay. So the history here, so a lot of people probably haven't heard of WashU, but in terms of price and difficulty to get into, it's kind of like a top 15 top 20 university. Lots of rich kids, people with high test scores, right?Rick: It's the best school that no one knows about.Tyler: Yeah, it's probably there. It's on par with the Northwestern. Except you've heard of Northwestern and you haven't heard it WashU.Rick: Exactly. I remember when one of my buddies in high school got into WashU and he was so excited. He was running around. This is a Charlotte private high school. He's running running around the halls going, "I got into WashU, I got in WashU." Everybody's like, "What is WashU? The University of Washington? You're going to go the West Coast?"Tyler: Or George Washington.Rick: "What are you talking about?"Tyler: Yeah, so no one's heard of it, but it's a pretty good school, which comes with all the downsides of good schools. So I did what every first time entrepreneur does, which is the first time I had to hire people, I was like, "I don't know. I'm going to go back to the school I went to. And I already know people there and I'm going to start recruiting." And it was pretty easy. Basically we posted on there, every university has a free job board and any employer can sign up and post there. We went to the career fair. People walk by, we g...

Tyler King, co-founder and CEO of Less Annoying CRM, shares his unexpected journey from computer science student to successful entrepreneur. He discusses the challenges of leading during the 2008 recession and pivoting from a traditional job to founding his CRM company to simplify processes for small businesses. Tyler reveals insights about moving from San Francisco to St. Louis for cost efficiency, the significance of nurturing a fulfilling work culture, and the perks of being a bootstrapped company that prioritizes innovation and customer satisfaction.

In this episode, we talk about why we started the podcast, who we think our ideal listener is, and how we plan to grow our audience.After going back and forth, the following framework emerged for marketing a podcastWhy did we start the podcast?Who is our audience and ideal listener?What problem are we solving for our audience?What makes our podcast unique?How will we measure success?How will we achieve success?Takeaways include: Our ideal listener is someone who:Wants to achieve freedom through entrepreneurshipWants to build something sustainable that will last for many yearsDoes things the way they see is the right way to do themDoesn't feel like they have a sufficient peer group for the hard conversationsControl, freedom, flexibility, and doing things the right way (as we define “right”) are important to our ideal listenerOur hosts (Tyler and Rick) share these valuesThere is a hole between the venture capital communities and serial entrepreneurs who are flipping companiesAnd that hole is build startups to last with sustainable impact and value creation for customers, employees, and ownersWe think the Startup to Last podcast is unique in the following ways:We have a deep-dive topic each weekWe do not follow the guest-interview frameworkOur hosts (Tyler and Rick) have skill sets that cover the whole spectrum in a way that most other podcast hosts don’tWe cover the spectrum in terms of company size and maturityTyler is 10 years into his company while Rick is in the very early stages of his companyWe are both comfortable with the essence of entrepreneurship: not knowing the answer and being OK with talking about it until we find itStartup to Last has achieved basic traction since launching in June 2019:200+ downloads across multiple platforms:33% are on Apple22% are on a web browser12% are on SpotifyThe rest are on various other platforms.11+ subscribers (Thank you)95% of our downloads and subscribers are from the U.SWe've got a couple in Mexico, and then some in EuropeFrom July to August, we doubled the number of downloads month-over-monthWe will measure success going forward by making the following metrics go up:SubscribersDownloads per most recent episodeWe will achieve success by:Talking to our existing listenersDoing customer development with potential listenersExperimenting with various growth channels and tacticsWe think our ideal listeners hang out in the following places:Online bootstrapper communities (e.g. people engaging at Indie Hackers and attendees at MicroConf )Social media sites (e.g. people who follow similar podcasts on Twitter)Q&A sites (e.g. people who are asking / answering related questions on Quora)Why did we start the podcast?Tyler: For anyone listening, you haven't been listening for long because this is our ninth episode ever. When we started this podcast, we were planning on just focusing on how do we make the content, so recording it, having a schedule, picking topics, editing, producing, publishing it. All that stuff, and at this point, we feel like we've kind of got it down. I mean, I'm sure we'll get better over time, but we've got a system where we can get podcasts published pretty regularly, so now the next question is, how do we get anyone to actually listen to this, and so we're going to talk about that today. Tyler: Keep in mind that neither of us have ever done a podcast before, so this is going to be very speculative and maybe every idea we have here is going to fail, but basically, we need to have this conversation anyway, so let's record it, and maybe people will find it interesting, what we're planning here. So with that said, you're more of a marketing person than me certainly, Rick, but I was thinking one thing we could potentially do is go over some ideas we already have or maybe you could start high-level and just talk about how you think we should even approach getting listeners to a podcast like this?Rick: I think one challenge that we have, Tyler, is that the reason we created a podcast was pretty selfish. It wasn't with a customer in mind or an audience in mind. For background, we started this podcast because we want to spend more time together. Right? You live in St. Louis. I live in Utah. Well, you came out every other quarter or every few quarters or so. I recently made a trip out to St. Louis. We had a great time, and we both said, "We'd like to spend more time together. How do we do that?" I think both of us were thinking podcast when we said that. Two reasons. One, we want to spend more time together. Two, it's kind of interesting to see if a podcast would work. Neither of us have ever done that. Let's try it. And so we did that, and now it's been, you said, nine episodes, I think?Tyler: Yeah. We did two or three that we kind of threw out before we started actually publishing them.Rick: Yup, yup, and so now, what is kind of weird here is we have content that is valuable to us. I'm getting value out of this every week when I talk to you. I think you're getting value out of it. But the content that we've created was made for us. It wasn't made for some market out there of potential listeners that we have a high confidence that will get value out of this.Tyler: Yes. Although, I listen to a lot of podcasts that are, if anything, even less for an audience than this. I listen to maybe five podcasts where it's two founders talking, and some of them don't even have deep-dive topics like we do. Some of them are just, "Hey, what did you work on this week? What did you work on this week? Okay. Bye," and I think they all have thousands or tens of thousands of listeners.Rick: In marketing, that's luck. Right?Tyler: Yes, but there's an audience that wants to listen to founders talking to each other I guess is my point.Rick: I can't disagree with that. We're coming at this from a product-first standpoint or not even a product-first. We're coming at it from a, "Hey, we want to spend more time together, and then see what happens," which is a little different than, "Hey, there's a problem out there," like a normal business venture or something that you're designing to actually be sustainable and make money. You go, "Hey, there's a problem out here that I know about, or that I heard about, or I've witnessed, or I've felt myself, and there's a market for people who had this problem. I've talked to them, and they're... They don't tell me what the solution is, but based on their symptoms, what's out there currently from a current solution standpoint, what they are looking to achieve, what their ultimate outcome or job-to-be-done is. You go, "Okay. Well, this person is trying to get from A to B. There's a problem getting in the way. I'm going to solve that problem, and then we're going to create a solution for that." We really didn't go through that process. So, we're in our ninth episode. We've got some traction, and we could talk about that, but I don...