Jonathan Siegel is a buddy of mine who lives in Tokyo. I can’t decide whether I’m more floored by the fact that he runs five businesses at once or has eight kids. He recently wrote a book The San Francisco Fallacy, mostly to share his experience with running software businesses for the last two decades with folks who might be getting a wee bit too much of their advice from Techcrunch. I think this makes an interesting companion interview to the last one we did (~6 months ago) with Thomas Smale, who runs the firm which helped me sell both of my businesses. Jonathan is an operator but he’s also a buyer of businesses, as opposed to me (an operator who recently sold businesses) or Thomas (a broker of them). [Patrick notes: As always, the below transcript occasionally has my thoughts inserted in this format.] What you’ll learn in this podcast: Why folks with successful businesses sometimes sell them (and how this creates opportunity for buyers) Why to make good decisions as a businessperson so that you can make “bad” decisions as a coder/artist/etc How to run five businesses at once (spoiler: put people in charge of the day-to-day work) How two entrepreneurs have found their goals changing over the course of their careers Running A Business Portfolio with Jonathan Siegel Patrick McKenzie: Hideho everybody. My name is Patrick McKenzie, better known as patio11 on the Internets, and I’m here today in Tokyo with my friend, Jonathan Siegel, who also lives in Tokyo. Jonathan is a multi-time entrepreneur, but I’ll let him give his self-introduction. Jonathan Siegel: Thank you, Patrick. It’s a pleasure to be here. I’d say my background is easiest to understand if you really think about me as a techie. I grew up loving anything that had a battery or I could plug it in the wall. I took apart everything, tried to put it all back together, and it rarely worked. I remember when I was 12, got my first computer. It was a 286 12 MHz. Took it apart, put it back together, and it actually worked. That’s back when you had the big cards in the computer with the hundred little ICs on the green silicon chips. Then after that, I got fascinated, and just did everything else that I possibly could on top of the computer. Ultimately, I learned how to do some software, and then went to school and did more software. Ever since then I’ve been tinkering around, for fun, on the computer and I’ve been rewarded with tons of opportunity from that, business and otherwise. Patrick: Yeah, I remember, I think I met you originally because at the time you owned, Earth Class Mail, which is a mail forwarding service that I’ve used to have a virtual mailbox in the United States for sending stuff to Japan for the last couple years. But it turns out –... For the full transcript see here.

I sold Bingo Card Creator, the business I’m probably best known for, through FEI last year. Thomas Smale, the principal of that brokerage, is now a buddy of mine, and he agreed to chat with me a bit about what goes into buying and selling online businesses. I think it is of particular interest to those of you with SaaS businesses already, but it might also be interesting for those of you who might found one eventually, as you can make early decisions (like e.g. technology stack) which built improved saleability into the business from day one. I’ve previously written about the BCC acquisition here. Note that this interview doesn’t go into much depth about that acquisition per se, partially because that isn’t a new topic for me and partially because I’m NDAed with regards to specifics. [Patrick notes: As always, the below transcript occasionally has my thoughts inserted in this format.] What you’ll learn in this podcast: Why SaaS businesses (and others with recurring revenue) receive a valuation premium Why you should use a broker to sell a business How to start getting a business ready for sale months before the process formally starts How to ease the acquisition process, both for the buyer and the seller Selling Online Businesses With Thomas Smale Patrick McKenzie: Hideho everybody. My name is Patrick McKenzie, better known as Patio11 on the Internets. I’m here for the 13th episode of the Kalzumeus Podcast with my friend Thomas Smale, who runs FEI. It’s a brokerage for online businesses, which I used last year to sell Bingo Card Creator. Thomas Smale: Hi, Patrick. Thanks so much for having me on. Patrick: Thomas, last year, you helped me sell Bingo Card Creator, which was the first business that I had been running from about 2006 through 2015 selling bingo cards over the Internet to elementary school teachers. Do you guys do a lot of work with SaaS companies? Thomas: In the last 12 months, just to put it in perspective, we did about 80 deals, and this year, we’re on track to do around 100 deals. At the moment, around a third of our business is in the SaaS or software space. It’s not all we do, but it is quite a big focus internally. Patrick: Just out of curiosity, what are the other sort of businesses that you guys see a lot? Thomas: If we broke it down a third, a third, a third, to keep it quite simple, we do e-commerce businesses, selling on Amazon or Amazon FBA. E-commerce through their own store would be about another third. Then the third content businesses, whether that’s content-based sites monetized with AdSense or Amazon affiliates, they’ve gotten quite popular, especially on the lower end. Then we also have a mixture of other businesses we do. Generally speaking, if it’s an online-based business, we will take a look at it. Patrick: One... For the full transcript see here.

In this podcast, Patrick McKenzie interviews Josh Doody, an expert in salary negotiation for engineers. They discuss topics such as avoiding the 'what is your desired salary?' question, trading off across multiple axes during negotiation, getting raises after being hired, and the importance of not revealing too much in salary negotiations. They also explore tactics for negotiating a salary raise and navigating salary negotiation and manager attitudes.

Keith and I are joined by special guest Jay Winder, CEO of MakeLeaps, in this 11th episode of the podcast.  We talk a bit about doing business in Japan, raising money vs. bootstrapping as a SaaS company, how AngelList is going to eat the world, and the usual eclectic mix of topics. [Patrick notes: The transcript below has my commentary inserted like this, as usual.] What you’ll learn in this podcast: Why you should negotiate from a position of strength and abundance. How to raise a round of funding through AngelList while not being in Silicon Valley. Why AngelList Syndicates are the future of seed stage fundraising. How to manage relations with investors when you have lots of them. How running a bootstrapped SaaS company is different than one which has raised early investment rounds. How the SaaS market is different in Japan. A bit about Jason’s new project, Sales for Geeks. A brief announcement: Keith and his co-founded Rachel launched a new product recently called Segmetrics.  It’s Baremetrics, for InfusionSoft — gives you actionable, one-look insight into which of your InfusionSoft segments (e.g. traffic sources) are producing results for your business.  If that sounds relevant, make with the clicky-clicky. Podcast: Customer Onboarding MP3 Download (~60 minutes, ~59.3 MB) : Right-click here and click Save As. Podcast format: either subscribe to https://www.kalzumeus.com/category/podcasts/feed in your podcast reader of choice or you can search for Kalzumeus Podcast in the iTunes Store. [powerpress] Transcript: Bootstrapping vs. Raising Money Patrick McKenzie:  Hello, everybody. Welcome to the 11th episode of the Kalzumeus podcast. I’m Patrick McKenzie, here with my noted co‑host, Keith Perhac and our good friend, Jay Winder as CEO of MakeLeaps here in Tokyo. Keith Perhac:  I’m Keith. Welcome to the 11th episode. I can’t believe that we got this out, literally one week after our last episode. Patrick:  This is downright scary. Keith:  This is scary. Patrick:  It’s almost like we have an actual podcast. Keith:  I don’t think so. All right. Cool. Welcome, Jay. Jay Winder:  Thank you. Hello. I appreciate the welcome. I was looking at you guys doing a podcast behind a thick Plexiglas window and I think, “Geez, that looks really warm and cozy inside that little podcast igloo”, so thank you very much for inviting me in. It’s a pleasure to be here. Patrick:  We’re happy to have you from outside in the cold. Jay:  Well, we have an air‑conditioner right here. Keith:  Hopefully you guys cannot hear, otherwise our editor is going to be very, very mad at us. Patrick:  Very, very angry at us. Keith:  In fact… Jay:  Should we turn it off? Patrick:  We were testing a little bit ago and it sounded OK. Keith:  You couldn’t hear it. Patrick:  Alright, so we’ll be talking about a few different things this time. Jay has a SaaS business called MakeLeaps. Why don’t you just give us a little bit of background on what that is for people to... For the full transcript see here.

Keith and I are back with the 10th episode of the podcast.  This time we’re talking about our wives and kids, how much they mean to us (lots!), and how we try to fit being good husbands/fathers around our mutual desire to keep growing the businesses. [Patrick notes: The transcript below has my commentary inserted like this, as usual.] What you’ll learn in this podcast: What Keith has been up to with Summit Evergreen and what Patrick has been up to with Appointment Reminder. How having children changed how we run our businesses. How delegating tasks is key to making sure we can spend appropriate amounts of time/brainsweat on being good husbands and fathers, as opposed to optimizing Nginx config files. How Japan’s poor systematic answers to the question of work/life balance decreases the birth rate here.  (Who said this podcast wasn’t educational?) Podcast: Putting the “Family” in Family Business MP3 Download (~53 minutes, ~50 MB) : Right-click here and click Save As. Podcast format: either subscribe to https://www.kalzumeus.com/category/podcasts/feed in your podcast reader of choice or you can search for Kalzumeus Podcast in the iTunes Store. [powerpress] Transcript: Putting the “Family” in Family Business Patrick McKenzie:  Hi, everybody. Welcome to ‑‑ what is this? ‑‑ the 10th episode of the Kalzumeus Podcast. I’m Patrick McKenzie, better known as patio11 on the Internet. I’m here with my buddy, Keith. Keith Perhac:  Hi, this is Keith. We are on the 10th episode, three and a half years in the making. Probably the slowest podcast ever. I know every time we say we’re going to make these a little bit faster and do this a little more regularly. Hopefully, in this new year, 2015, we’ll actually get that done. Here’s knocking on wood. Patrick:  Knocking on wood. I think we ship products and children about as quickly as we ship podcasts. Keith:  [laughs] Patrick:  In fact, I think that’s almost literally true. [crosstalk] Patrick:  This segues nicely the topic for today. We’re going to be talking about what it’s like to run a business as two guys who are very committed to being family men. Not just to grinding away and burning the midnight oil and the work stuff, as we might have done in our younger and stupider years. Keith:  [laughs] I don’t know. I still do that on occasion, but having a family has definitely changed it. Patrick:  Yeah, so we are going to talk a little bit about family stuff in a few minutes, but we want to steal a [inaudible 01:06] from Rob Walling and Mike Taber at the “Startups for the Rest of Us” podcast, which is one of my personal favorites. They start off every episode with just a little update on what’s new and exciting in their businesses. I thought, “Hey that’s kind of interesting to pattern after.” We’ll try it and see if it looks it. Keith, we haven’t heard much about Summit Evergreen recently. Why don’t you start us off with that? How’s... For the full transcript see here.

Samuel Hulick, one of the guys I trust most with regards to SaaS user onboarding, joined us for this episode of the podcast.  I met Sam first when he was writing a book on the topic.  The best evidence I can give you for the proposition “Sam knows more than the vast majority of people about user onboarding experiences” is the fact that he’s written up 25+ of them publicly (e.g. Basecamp’s) and that the writeups are of very high caliber.  Check them out sometime. [Patrick notes: The transcript below has my commentary inserted like this, as usual.] What you’ll learn in this podcast: What mistakes SaaS companies frequently make with regards to user onboarding. How to start preparing users for success pre-signup, using site copy and appropriate expectation setting in marketing. How SaaS companies often botch product tours, and how you can make yours serve the user rather than serving the product team. How to use lifecycle emails to make customers more successful. How organizational issues at SaaS companies often directly cause problems in the artifacts given to customers, and how you can avoid this. Podcast: Customer Onboarding MP3 Download (~75 minutes, ~110MB) : Right-click here and click Save As. Podcast format: either subscribe to https://www.kalzumeus.com/category/podcasts/feed in your podcast reader of choice or you can search for Kalzumeus Podcast in the iTunes Store. [powerpress] Transcript: Customer Onboarding Patrick McKenzie:  Hideho, everybody. This is Patrick McKenzie, here with the ninth episode of the Kalzumeus Podcast. Our guest today is Samuel Hulick, who is behind useronboard.com. My usual co‑host, Keith, couldn’t make it today. I moved down to Tokyo recently [Patrick notes: And will talk about that more some other day.], so it’s a bit of logistical nightmare getting everybody together, but hopefully that’ll work out itself over the next couple episodes. Anyhow, it’s great to have you here, Sam. Samuel Hulick:  It is wonderful to be here. Patrick:  I think today we’re just going to talk a little bit about what you’ve noticed in your experiences as a consultant/author on the topic of user onboarding, what software companies typically do well, do poorly, how they can improve on it. Also, on a meta-level, I’d like to ask about your experiences of building up the reputation as an expert in this emerging field of dev‑related topics, and how that’s worked out for you personally in your career. Sound good? Samuel:  I would be delighted to cover all of that. Patrick:  Awesome. I guess, first question. Sam is one of the few people I trust on the topic of user onboarding.  I trust Sam largely because he’s done maybe 20 public tear‑downs of websites, saying, “Hey, this is a SaaS company. I signed up for their product.” He makes copious screencasts/screenshots of the product during the onboarding phase. If you’re not familiar with that term of art, onboarding... For the full transcript see here.

I recently met Steli Efti, founder of Close.io, in Palo Alto, and did a podcast episode with him.  Transcript and links below as per the usual. Sidenote: I listen to a lot of podcasts and have been using Marco Arment’s Overcast app recently to do so.  It was the best $5 I ever spent.  Give it a whirl. [Patrick notes: The transcript below has my commentary inserted like this, as usual.] What you’ll learn in this podcast: Why engineers speak a different language than sales people. How we can get over our reluctance to do sales to sell more software (without selling our souls). Tactics for getting over the pain of rejection when doing sales calls (and sales generally). How to qualify prospects so you don’t waste time pursuing deals which you’d never, ever close and can instead concentrate on the deals which your personal attention will cause to close quickly. Why Steli shuttered a multi-million dollar consultancy to focus on Close.io’s SaaS product. If You Want To Listen To It MP3 Download (~80 minutes, ~54MB) : Right-click here and click Save As. Podcast format: either subscribe to https://www.kalzumeus.com/category/podcasts/feed in your podcast reader of choice or you can search for Kalzumeus Podcast in the iTunes Store. [powerpress] Transcript: High Touch Software Sales Patrick McKenzie: Hi, everybody. I’m Patrick McKenzie and this is the — I don’t even know what this is – episode of the Kalzumeus podcast. Thanks for staying with us. Keith, unfortunately, can’t make today. He and his wife and daughters are having fun back in Japan, but I am here in sunny Palo Alto, California with a buddy of mine who founded a company. We’ll talk you a little bit about the story later, but he founded a company, which these days, it’s Close.io, a YC funded company. Meet Steli. Steli: Hey, guys. I’m super excited and honored to be on the podcast, a big fan of it. Patrick: Steli, can you tell us a little bit about your background? I’m more from the engineering side of the house and you are… not. Steli: I’m originally from Greece, born and raised in Germany. I’m basically a high school dropout that has no credentials whatsoever, completely unemployable, and never had a real job in my life. I’ve been an entrepreneur my whole life. A lot of times I joke that the entrepreneurial super power that I use to move things forward is the hustle in sales. I love communicating. I love people. I love moving things forward, on the business end of things. I’ve been an entrepreneurial salesperson my whole life. For the first few years, small businesses, boot-strap businesses back in Europe, and then seven and a half years ago sold everything I had, bought a one-way ticket to come to Silicon Valley, follow the legend of becoming a tech entrepreneur with... For the full transcript see here.

Keith and I recorded a new episode of the podcast last year, but we didn’t get around to releasing it. [Patrick notes: The transcript below has my commentary inserted like this, as usual.] What you’ll learn in this podcast: How to pick a small, self-contained product, which is good to cut your teeth on as a dev-turned-entrepreneur. How Keith extracted Summit Evergreen out of his consulting work (improving infoproduct businesses). How to use concierge onboarding to increase conversions and decrease churn of SaaS businesses. That it is possible to build a very successful consultancy without being quote-unquote Internet famous. How to use Standard Operating Procedures documents to have employees do repetitive tasks without needing to actually automate them, while you’re still exploring for the best procedure for completing those repetitive tasks. If You Want To Listen To It MP3 Download (~115 minutes, ~85MB) : Right-click here and click Save As. Podcast format: either subscribe to https://www.kalzumeus.com/category/podcasts/feed in your podcast reader of choice or you can search for Kalzumeus Podcast in the iTunes Store. [powerpress] Transcript: Launching New Products Keith Perhac: We’re started. Patrick McKenzie: Hello everybody and welcome to…What is this? The eighth episode of the Kalzumeus Podcast. [Patrick notes: There was an episode #7 in recording sequence, but due to some issues, we haven’t gotten it ready yet.  It will retroactively become the 8th episode.] Keith: Indeed it is. Patrick: I’m Patrick McKenzie here again with my co‑host, Keith Perhac. Keith: Hello, again. CreditCard.js: A Nice Product, Both For Customers And The Founder Patrick: Let’s see, we’ve got a fun day planned ahead of us. First thing we’re going to be talking about is Creditcard.js and that’s in eponymous creditcardjs.com. Keith: That’s because that came out today, I believe, on Hacker News, which will be about two weeks from when we actually get this up. [laughs]  [Patrick notes: Actually recorded 8+ months ago.  Sorry — life happened.] Patrick: Predictably, just to give you folks an idea of what it is, it’s well executed CSS, JavaScript and HTML which does the standard static credit card form. But it does it well, such that when you start typing in a credit card number with a four, it knows that it’s a VISA and it does error correction and does the Luhn checking in real-time without having to submit it to your servers. This is like every credit card form that you’ve ever coded in the last five years, except it’s done well without you having to work at it for three hours. It makes a very good self‑contained product, I feel. Something that can be built over the course of a few weeks, tuned to within an inch of its life, and then sold to people. Because it’s sitting in the critical path on taking money from every website ever, it’s worth quite a bit of money relative to the amount of time I feel it would take to build, and can be sold to many people in parallel. Keith: If... For the full transcript see here.

Happily, there are many ways to productize your relationships with customers or your expertise as a consultant. [Patrick notes: The transcript below has my commentary inserted like this, as usual.] What you’ll learn in this podcast: Why vegetarians do not give great advice on pricing hotdogs, and Hacker News comments about the inadviability of selling information very rarely come from people with actual budget to buy information Why having multiple packaging options (for example, at an X / 2X / 5X ratio) increases total revenue from products Why you don’t have to be “Internet famous” to build an audience via teaching, and perhaps use that to sell things down the road If You Want To Listen To It MP3 Download (~90 minutes, ~82MB) : Right-click here and click Save As. Podcast format: either subscribe to https://www.kalzumeus.com/category/podcasts/feed in your podcast reader of choice or you can search for Kalzumeus Podcast in the iTunes Store. [powerpress] Transcript: Teaching As Marketing Patrick McKenzie:  Hi to everybody. This is Patrick McKenzie, perhaps better known as better known as Patio11 on the Internets. Welcome to the, I think, seventh edition of the Kalzumeus podcast. [Patrick notes: 6th!] I’m joined here by special guest Nathan Barry, author of “Authority,” founder of ConvertKit, and a guy who has a few other things in his expanding product empire. [Patrick notes: If you sell software, information, or consulting services, take a look at ConvertKit.  I started using it recently for one of my businesses.  It bakes a lot of acquired smarts into an email marketing workflow tool.] Nathan Barry:  Thanks for having me. Patrick:  Thanks very much for being here. I think we’re probably going to be talking about info products today, primarily. Let’s ask the obvious question first. Do you like the term “info product”? Nathan:  I think it’s a little degrading. I tend to just refer them as courses or books. “Info product” always brings up the scammy Internet marketer. Patrick:  Right. The whole “make money online” niche. Nathan:  Right, exactly. I just try to write things and teach things that provide value. “Info product” doesn’t demonstrate that very well. Patrick:  That’s something I totally agree with. I try to call mine “productized consulting” because the book was like a consulting engagement except delivered with less of my hours of unique attention attached to each delivery. I think you were also a consultant before you got into being a publisher, right? How did the arc of that transition go for you? Nathan:  I did some freelancing in college, and then after I left college, I did a year freelancing full time. That worked pretty well for me, but then I went on an extended five or six week international trip. Didn’t do any work. Came back. It was the beginning of 2009, and there was a recession going on in the US, so nobody wanted to work with me then. I ended up taking a job leading the design team at a local startup, and... For the full transcript see here.

Keith Perhac and I are back with the 5th epsiode of the Kalzumeus podcast. Keith and I both have experience working as consultants in software development and online marketing.  People often ask us how to transition away from the feast-or-famine nature of freelancing, where you do very well when you’re delivering engagements and getting them paid quickly, and then do very poorly when work dries up or you have invoice collection issues.  One way to improve on this is building recurring revenue for your consultancy, via products.  A lot of folks think that the only way to do this is spinning a SaaS out of your consultancy.  While I have an abiding love for SaaS, building SaaS businesses takes a metric truckload of time and largely is not a good option if you have e.g. a personal burn rate of $6,000 which you need to cover next month. Happily, there are many ways to productize your relationships with customers or your expertise as a consultant. [Patrick notes: The transcript below has my commentary inserted like this, as usual.] What you’ll learn in this podcast: Why I wound down my consulting business recently, even though it was pretty successful How to sell consulting clients retainer agreements, long term support contracts, and software licenses to become less dependent on revenue from new engagements How “productized consulting” (it’s like infoproducts, except with a less obnoxious name) can make tapering down consulting viable for people who need predictable revenue Examples of non-software products that technically-oriented folks could be creating How Keith and I have applied content marketing (God, another word I hate) and effective use of email to sell these sorts of products Our advice on pricing/packaging, and a few pointers at successful implementations of it to copy liberally be inspired by If You Want To Listen To It MP3 Download (~75 minutes, ~68MB) : Right-click here and click Save As. Podcast format: either subscribe to https://www.kalzumeus.com/category/podcasts/feed in your podcast reader of choice or you can search for Kalzumeus Podcast in the iTunes Store. [powerpress] Transcript: Quitting Consulting Via Productization Patrick McKenzie:  Hideho everybody and thanks for tuning into, what is this, the fifth episode of the Kalzumeus Podcast. I’m Patrick McKenzie, better known as Patio11 on the Internets and I’m here with my co‑host Keith Perhac. Keith Perhac:  Hi, I’m Keith Perhac, not known on the Internet. Patrick:  Yeah, it’s been an absurd amount of months since we did the last version of the podcast together. What’s new and exciting with you, Keith? Keith:  Oh my God, so much. I have a new daughter, which is fun, takes a ton of time out of my life but the main thing that I’ve been working on, non‑family related, is new productization. I’m sure you have a lot to talk about that, as well. I’ve been doing consulting about two years now, going on three. It’s gotten to the point where I want to start that whole productization thing. I think that’s what we’re going to... For the full transcript see here.