From Vision to Venture Ep. 03: Gregory Koberger, Founder ReadMe.
From Vision to Venture Ep. 03: Gregory Koberger, Founder ReadMe.
Moesif’s Podcast Network: Providing actionable insights for API product managers and other API professionals
Our guest on this episode is Gregory Koberger, founder of ReadMe, an API documentation and developer tools platform. In today’s episode, Greg shares the highs and lows of building ReadMe, from designing developer-centric tools and launching new product lines to handling market shifts and avoiding layoffs during tough times. Greg dives into his approach to scaling sustainably, managing burnout, and the invaluable role of a strong team. Join us for an inspiring conversation on overcoming founder challenges with resilience and purpose.
Matt Tanner, former Head of Developer Relations at Moesif, is your host today.
Listen to the episode on SoundCloud above, watch it on our YouTube Channel or download it on Apple Podcasts, YouTube Music, or wherever you listen to podcasts.
Table of Contents
- 00:00 Introduction
- 02:10 From Engineer to Entrepreneur
- 03:37 The Art of Developer-Centric Design
- 04:45 Building a Developer Hub: The ReadMe Approach
- 09:47 Surviving Market Challenges as a Founder
- 12:30 No Layoffs: A People-First Leadership Choice
- 14:49 The Importance of a Co-Founder
- 17:52 Recommendations for Aspiring Founders
Introduction
Matt Tanner - Hello everyone and welcome back to the Vision to Venture podcast. Today we have Greg Koberger joining us from ReadMe. Very excited to have you, Greg. Thanks for joining us.
Gregory Koberger - Excited to be here.
Matt - Awesome. So yeah, just to give you a bit of a rundown, the first part that we’re gonna tackle is a little bit about you, a little bit about ReadMe. Then we’ll move into some of those typical startup challenge questions and would love to hear some of your input. And then lastly, for aspiring founders or already founders, we’d love to hear some of your tips and tricks to make sure that things are running smoothly, whether that be for developing ideas, scaling out a product or even raising funds. All right, let’s get started then. So first thing we’re gonna tackle is who you are and a little bit about your background.
From Engineer to Entrepreneur
Gregory - Perfect. So like you said, my name’s Greg Koberger. I’m the founder of ReadMe. My background is engineering. I’ve been writing code for decades now at this point, I guess, and had a few jobs at startups and bigger companies as an engineer. At some point, switched a little more to design and kind of really enjoyed both design and engineering. And that’s kind of what got me into dev tools. I like designing for developers a lot. That’s always one of the two things that really excites me. The other is just designing bigger experiences, which is why we do a conference for a lot of reasons and all that, but I like doing stuff like that. So the two things I’m designing for are experiences, but the other one is developers. And I think developers, I mean, you probably get the same thing. And most of them, I think developers are interesting because there’s this concept around usability that everyone gets for apps, but developers never really got the love that they kind of needed and deserved for years, and that’s changed the past like five, six, seven years at this point. But yeah, it’s a weird thing ‘cause like most apps, the goal is to make it as simple as possible, whereas for dev tools, it’s to make it as powerful as possible while also being simple. And that’s kind of a really interesting thing. So that’s me and my background.
The Art of Developer-Centric Design
Matt - Awesome. Yeah, so at Readme, based on that, I mean, we can kind of probably see the prelude to why you’ve dug in at Readme. So maybe give a little bit of background on what Readme does and the main challenge or challenges that you’re tackling over there.
Gregory - Yeah, definitely. So Readme does API documentation for developers. So we sell to companies. So if you have a company, we would be your developer.whatever.com. We do documentation. We do debugging tools for your users. They can look through their logs, API logs, stuff like that. They can play around with it. We generate code snippets and all that. So our goal is to kind of just be a developer hub for anyone who has an API or anything like that.
Building a Developer Hub: The ReadMe Approach
Matt - Awesome, yeah. And I can imagine that that’s getting a lot of traction right now because as you mentioned, developer tools, developer websites, all these types of things are getting a lot more attention now, especially with the advancements that we’ve seen in a lot of different areas where kind of everyone has their hands on APIs these days. So yeah, so moving on past the company and a little bit more towards some of the challenges that you face as a founder, whether that’s at Readme or a previous company, let’s hear a bit about a challenge that you’ve encountered. And I don’t mean to sound too much like an interview, but a challenge that you encountered and kind of some ways that you were able to get around that problem. So how did you solve it?
Gregory - Yeah, definitely. I thought a lot about what to say for this ‘cause I knew this question was coming. And the thing that kept coming back was just this past year. There’s a lot of things over the past seven or eight years I’ve been doing this that I could have talked about, but luckily it’s been pretty easy. It’s been incredibly hard, but there’s not been any gigantic things that have shown up and been truly horrible except for this past year. This past year was tough for everyone, not just at Readme. The marketing distance changed. We got really lucky that we didn’t raise money the past year or sorry, the past like the 2000, 2001 when things were like really, really great. So we didn’t have like a gigantic valuation to worry about or anything like that. But that being said, it was kind of like going, like last summer we’re coming off years of COVID and I think people were like tired and a little depressed. And then there was market issues and I don’t tend to spend much time thinking about the market in general because there’s really no point. But I don’t know what it was like for you guys at Moesif, but it was people were scared, like churn was going up ‘cause companies were showing up at business. And again, it wasn’t like crazy or anything, but it was like, oh, this could go really badly over the next year. And it was the first time, ‘cause I said before, there’s been problems, a lot of problems over the past like eight years or so, but the problems were very like fixable or whatever, whereas this felt like it could be like an existential crisis that we had very little control over. And like there’s a lot of like talk about like, well, other companies were definitely doing layoffs and I had a hard rule where I was like, we’re not even talking about this. And that kind of takes a big thing off the table when you say no layoffs. And the reason I didn’t wanna do layoffs was because I just want Riemann to be a place that people enjoy working at and I think layoffs are just really, really tough. They’re really good at solving the money issue. Like you do the math and you’re like, okay, well, if we lay off five people, then all of a sudden like this happens or whatever and it’s a good thing. But like, for me, that’s such like a callous way to look at things ‘cause what I care about is not money or building a billion dollar company or anything like that, but like building a good place to work and it just undermines it to do that. So I took layoffs off the table like easily and pretty quickly, but that still meant that, okay, we have to fix these problems. And it was hard. So what I did, and I’m gonna talk from my perspective, there’s a lot of people in my company and everyone did a lot. So this is just my version of the story, not the whole story. But for me, I was like, okay, like we have to do things differently. And I canceled all my meetings and like started writing code again. A bunch of people around me started like getting and building new features and stuff like that ‘cause we’re like, okay, we have to fix the churn issue. We’re not gonna get these companies to stay in business. That’s outside of the realm. So we just started launching new products. So we launched three new products that had price tags on them. Before that we had one line of products like that we charged for and now we have four. So the original one plus three new ones. And we just, it was kind of tough ‘cause it felt like after COVID, like things were finally kind of getting better and like people were like a little happier and stuff like that, then all of a sudden we get hit with this like, oh, like, it’s kind of like, now we gotta work, now we gotta build. And yeah, like we didn’t have to do layoffs. Like everyone on the team worked really hard and did great work. No one was pressured in a bad way. Like no one was working nights and weekends. Like luckily we were able to keep it where it was like, you know, it was still, my big belief is like, unless there’s the sites down or something like that, like no one should work nights or weekends. But people still like worked really hard and like, you know, things kind of like flipped internally and yeah, it wasn’t fun. It was probably the worst year, well, definitely the worst year of my life as a CEO. But we got through it without any big negatives. You know, it was, I think it could have gone either way, obviously, and I saw a lot of my friends’ companies kind of go different directions and all that. And it wasn’t fun, but I am proud of everything we built, everything we did, and that we, you know, never considered layoffs or anything like that. And we got to a cashflow positive, which again, we were pretty close, so it wasn’t a big deal. I’ve always been kind of thoughtful about that, but yeah, it’s nice. It was nice to kind of like control our own destiny and not have to do anything bad. We kind of like fought this downside with like, by doing good things, by shipping more and exciting stuff, as opposed to like, you know, desperately like finding ways to even out the balance sheet.
Surviving Market Challenges as a Founder
Matt - Right, so I mean, really, instead of trimming the fat in terms of getting rid of resources to free up cash, you trim the fat probably around the productivity type of stuff where you’re like, okay, let’s double down on making our product better to hopefully increase the cashflow versus increasing the cashflow kind of from a less optimal way of, okay, we don’t, we can’t bring in new cashflow, so let’s kind of drop our expenses down. Instead, you were like, hey, let’s double down, let’s make something that we can sell even more of so that we can bump it up that way. Is that kind of the approach that you were thinking of when you made that decision?
Gregory - Yeah, I think it’s really hard to build the good things when you have like a excess of resources. By resources, I mean people, I mean like money. Like, even if we weren’t raising money, there’s always that thing in the back of your head which is like, oh yeah, I could walk out tomorrow to like, you know, Sand Hill Road, I guess that’s an outdated reference, but like to, you know, San Francisco and just like, you know, raise a big round probably at a, you know, gigantic valuation. And it’s, when you have that kind of like backstop that you know, like, okay, if things go badly, like we always have that and raising money, by the way, is incredibly hard even when the market’s good. But like just kind of knowing that like that was possible, it makes it really hard to think about things as in like, ‘cause you’re always like, you have like abundant resources, so you’re like, well, let’s put a little more time, a little more effort into this, like let’s, you know, do it right or do like, you know, you don’t have like pressure and then the past year we had a lot of pressure and you know, sometimes that goes really badly and sometimes, and for the record, as much as I’m happy now, I don’t think, you know, I don’t think it was a fun year, I don’t think, if I could go back in time, I would prefer, it didn’t happen, but you know, it’s all the year later from then, this is probably the best case scenario. But then like, it wasn’t like, it was a big toll though, like I was so depressed and miserable and overwhelmed after the year, so I, you know, I was so out of it. So I took a six week soft right at like, a few months, or about two months ago, because like about a year after this happened, because I was just a year of just like working nonstop and I was exhausted, so I was lucky that I could do that, ‘cause I have a great team that made it so it didn’t even seem like I was gone, but yeah, I definitely needed some time off after all that.
No Layoffs: A People-First Leadership Choice
Matt - That’s actually, that’s a good point. So I mean, one of the things that a lot of founders and even, you know, people who are early into a company, stepping away for a little bit in order to really amplify what your productivity is later is tough to do. So kind of what were some of those steps like, did you just decide like, hey, I’m gonna take a bit of time off, kind of cut everything out, do what you need it to do, or was it a little bit more methodical like, hey, three weeks from now, I’m gonna take off six weeks or whatever? Yeah, kind of, how did you get to that point? ‘Cause that’s a really interesting one, is I see a lot of founders who burn out or just are just generally unhappy because they don’t get to take that time off.
Gregory - Yeah, and I think I’m incredibly lucky that I was able to. I think, you know, I’ve been doing this for eight years and this is my first actual break. I might take time off a lot, but like, it’s hard to, it’s, there’s, the stress for my job isn’t the day-to-day work, it’s the like, the worrying about things or thinking about things or like, you know, and that seeps into weekends, even if I, you know, even in hours that I’m not working, like I’m still, I think about it. So this was the first time I could like, actually like, just not think about anything. ‘Cause it was six weeks and I was like, I’m just completely gone for six weeks. I wasn’t actually, I got bored a little bit and came back and did stuff here and there. But it was, I got really lucky because, so the reason was I knew I was gonna do it for a few months before, just because I was just so burnt out. But we needed a few hires to kind of, you know, fill in some gaps. So we hired some people and they’ve been great and that’s why I was able to do it, luckily. So it wasn’t, we didn’t hire them so I could take break, but like, we hired them ‘cause we were gonna hire them anyway and like, once all the puzzle pieces were in place, then I could sneak away and no one would really notice. So it was super nice, but it’s not something you can do, especially early on. I remember early, early on at ReadMe, I got so burnt out. This was like, maybe like three or four years in, maybe less than that. And like, I just wanted to quit and I couldn’t figure out who to quit to ‘cause I didn’t have a boss or anything. So I was like, I don’t know how to quit. And so, obviously I didn’t and I’m glad I didn’t. But yeah, but I felt, so I couldn’t take a break then because we were small and like, if I left for a week, like, so it was, it’s tough. Like, it took eight years before I could take time off and like, I can’t do this every year. So it’ll probably be a few more years so I can do it again. So it’s hard.
The Importance of a Co-Founder
Matt - So with that lesson, you know, we’ll move to this last piece here, which is those kind of tips that we can give to other founders or aspiring founders. And one that I would love to hear on is, if you were to do it again, okay? So thinking about kind of being able to separate the work life and the personal life, which is really hard to do as a founder, but would you, instead of taking, let’s say eight years to get to the point where you’re able to do that, do you think that there’s a couple of things that you could put in place if you were to start another company in another universe, that you would put it in place kind of right away to make it so that being able to distance yourself from the business to kind of get your equilibrium back, would you, what would those be?
Gregory - Yeah, I don’t think there is an answer. I know a lot of founders and I think there’s always a grass is always greener type thing where it’s like, I should have raised more money. I should have raised less money. I should have hired this role sooner. I should have hired this role later. Like I should have not done enterprise this role. I should have done enterprise. Like I think there’s so many different like things and I’m not saying that I did things perfectly at all, but I can’t really think of anything huge that I would be like, oh, this is what I do differently. There is one big one. I don’t want to undercut what I just said, but I think the big one that I didn’t have was a really good co-founder from the beginning and one who understood businesses really well. I understand product well. I understand like a lot of things. One thing that doesn’t make sense to me just intrinsically is how to run a company. How do I think about money? How do I think about cash flow, stuff like that? And I’m not saying I would have wanted it sooner. I guess I would because like especially early on, like none of it really mattered because you’re just trying to make something work. So the spreadsheets are less predictable and all that, but I have a CEO Pat now and he just understands how it all works and like I can learn stuff and I can understand it to a certain amount, but like it’s never come naturally to me. So I do wish I had a co-founder from the beginning. Just someone who’s like in it with you. There’s a lot of people who have worked at ReadMe for many, many, many years that are absolutely phenomenal and like I love, but it’s different when you like, ‘cause the buck still stops with me and it’s still like, it’s a little bit different not to have a co-founder no matter how loyal and great employees are. So I would go back and if I go back I would probably, I wouldn’t do it again without a like, not just a co-founder ‘cause you just, you don’t want just someone there. You want someone who like really fills in the gaps, but I didn’t know what my gaps were at the time. Because at the time I didn’t have gaps early in the company that are the same gaps I have now if that makes sense. Like early on it was like desperately trying to just get a product that someone kind of wanted. And now like the gaps are very different. So and you just need, yeah, so it’s tough, but I think that’s the one that I would do differently.
Recommendations for Aspiring Founders
Matt - Okay, okay. Any other kind of tips maybe? I mean, when you were developing the idea for Readme, kind of how did that come about? Because I think a lot of folks, especially aspiring founders go, I really wanna found a company. I just don’t know what I wanna build.
Gregory - Yeah.
Matt - Do you have a little bit of maybe some guidance there on how they can do that?
Gregory - Yeah, so when I started Readme, I knew I wanted to start a company, which is the worst reason to start a company. And I was like, I just thought that like, this idea was not the best idea. And frankly, it’s not the best idea. Like it’s, there’s much better ideas out there. And I like tried different things, but like I would procrastinate by working on Readme because it was just what excited me. And I couldn’t get it out of my head. And I just like, that’s all I wanted to work on. And I kept like being like, ah, it’s just not a good, I don’t know, like I don’t know if it’s a good business. Like there weren’t many dev tools that were big back then. It was just GitHub and that’s it. And there was a few others, but like it felt like a really tough path. And I think like just that that product, that founder product fit is really important where it’s like something that you like, ‘cause this becomes your absolute, like every minute of every day. And like if you end up hating it or not loving it, like it’s brutal, it’s brutal when you love it. And it’s real brutal when you don’t. And the second thing is like, I think you have to be, it’s hard to be honest with yourself because everyone’s gonna be nice to you and be like, oh yeah, it’s a great idea. And for me, I got a lot of those, oh, it’s a great idea. Not for Readme, but like I was trying to find like the very, like I have the same idea, but it was like, where do I draw the line? Like what do I do? What don’t I do? What’s the, like how do you like? I knew there’s something there, but I wasn’t quite there yet. And then like I kept like putting off like launching ‘cause I kept like working with people and it wasn’t quite there and I could just see that people weren’t that excited about it. And then like I finally hit something and people were like, like you just tell that it flipped. They’re like, oh, like can I sign up for it now? And I’m like, no, it’s not ready yet. They’re like, well, when’s it ready? And like it just changed so quickly the way people were responding to me. And I was like, okay, like I’m so glad that I like kind of like took a beat and like try to understand like what people wanted and waited because it’s, you can just tell when people like are just being nice or trying it out or whatever. Or maybe you can’t tell, I don’t know. But like you definitely tell when they’re like, they love it and like that’s kind of the important part you have to wait for.
Matt - Awesome, that’s great. I think that’s a great answer to a question that so many people kind of ask themselves of what should I build? How should I build it? What do I look for in something that I’m passionate about? So thank you so much for answering that.
Gregory - Definitely.
Matt - With that being said, I’d love to wrap things up but I always ask one last question. I think this is kind of like across the board every podcast asks this. But if you had to recommend a book, a podcast maybe even some type of publication that founders should be reading or maybe you should take a look at, what would you recommend?
Gregory - Can I do a weird one? Or I’m gonna do a weird one I guess.
Matt - Absolutely, absolutely do a weird one.
Gregory - Okay, I want to take it some weird direction. So there’s a show called Mythic Quest. I’m not sure if you’ve heard of it. It’s by some of the people who do Always Sunny. It’s on Apple TV. It’s a sitcom TV show, workplace sitcom. It’s okay, it’s not a great show. It’s fine, like it’s fine. But the fifth I think episode of the first season is like this like micro story. It’s called A Quiet Dark Place or Quiet Dark Death, something like that. And it’s this episode with like completely different characters, completely different actors, like completely different storyline. It’s just like a completely different vibe. And it’s, this is, I’m recommending this for founders. It’s so good. He’s, the characters in there are starting a game. And so not a company, but like they are starting a company, but it’s a game, not a startup. And it’s, to me it just like kind of like mapped a lot of my experiences and stuff. And I think it’s such a fascinating, like everyone I’ve shown it to like has like a different takeaway and like felt something different from it. Some people just liked it. But some were like, oh my God, like that’s, you know, what I’ve been struggling with and stuff like this. And it’s a really great episode. You don’t have to watch the whole show to understand it. You just need to watch that one episode. There’s a few little things that maybe won’t make sense, but like it’s a standalone thing completely. So that’s my weird answer.
Matt - Awesome, no, thank you so much. That’s great. With that, I want to thank you again for joining. It’s been absolutely great chatting with you. And yeah, hopefully we’ll chat again sometime soon.
Gregory - Perfect, always happy to do that. Thanks so much for having me on.
Matt - Awesome, thanks so much, Greg.
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