How do you know an idea is worth pursuing?

Joining me is a listener who has been a part of the Mixergy community since 2008. He is someone who worked for Mozilla and discovered a pain point there.

But when he applied to YC with a solution, he didn’t get in. We’ll talk about what happened that day in this interview. And also about what he changed in his pitch after that painful experience.

Greg Koberger is the founder of ReadMe which gives teams the tools they need to create and manage beautiful documentation with ease, monitor their APIs and connect with their users in more personal ways.

Gregory Koberger

Gregory Koberger


Greg Koberger is the founder of ReadMe which gives teams the tools they need to create and manage beautiful documentation with ease, monitor their APIs and connect with their users in more personal ways.


Full Interview Transcript

Andrew: Hey there, freedom fighters. My name is Andrew Warner. I’m the founder of Mixergy where I interview entrepreneurs about how they built their businesses, and I do it for real entrepreneurs. Joining me is somebody who listened back in 2008 when I was getting started, and he was pointing out how things felt so much smaller back then. It felt like a smaller ecosystem. It felt like a smaller group of people who were starting companies, it felt smaller and it grew and grew to the point where I sometimes . . . I miss those old days too sometimes, you know, Greg. Don’t you?

Gregory: Yeah, I feel like I still love Silicon Valley and San Francisco’s startup culture. But back then it wasn’t cool to be doing startup. It was 2008, the market had just crashed. When I first moved out here, there’s absolutely no funding. There’s a few big companies, but like Google wasn’t . . . they were still the underdog. Facebook, if they exist was so the underdog, or they definitely existed, but they were the underdog and like, I just loved . . . Everyone I knew that worked in Silicon Valley in San Francisco in 2008, just it was kind of crazy and weird and just like wanted to build something. It was a small community and people did it not because they’re going to be billionaires, because they wanted to make something, and I kind of really love that mentality.

Andrew: There’s also the sense of underground to it where just a few people knew about it, not the rest of the world. I do feel though, Greg, that it has gotten back to not being cool. The cool thing now is to be a vlogger, and Instagram star, and influencer, any sports player, right? Let me introduce the person who I’ve been talking to his name is Greg Koberger. He is the founder of a company called ReadMe. They make API documentation look good and be more functional. I want to understand all parts of how . . . Like, frankly, I’m going to go down to the level of what is an API? Why does it even matter? Why does documentation matter? And then don’t worry people, I know that for most people, this is going to seem too basic. So we’re going to definitely go to the story of how he came up with the idea for ReadMe. How he was working at Mozilla, and they encouraged him to pursue his vision, and how the first Y Combinator interview failed, flopped, didn’t work out.

Gregory: Did not go well.

Andrew: No, it seems terrible. How he picked up the pieces. And now the company is going really well. Apparently, it’s even profitable. We’re going to do it all thanks to one phenomenal company. It’s called Toptal. If you’re hiring developers, you got to check out Greg, you are profitable still. Is that right?

Gregory: We weave in and out of profitability at this point but pretty close.

Andrew: That’s shocking to me that you’re even . . . That you were profitable for a while, that you even would care about it. Revenue is where?

Gregory: We are, well, we have about 25 employees give or take and still like I said, pretty much profitable, so you can do the back of the napkin math on that one. But multiple millions of dollars a month or year revenue. Okay.

Andrew: Okay, got it in recurring revenue?

Gregory: Yes, yes.

Andrew: All right. Super basics, I promise people, we’re going to go beyond the basics, but super basics. What’s an API? What does it matter?

Gregory: Definitely. So, if you’re not a programmer, you’ve definitely used an API at some point. I don’t think there’s an entire or a single website that’s been built in the past forever that doesn’t use some sort of API. There’s companies like if you ever get a text message, they’re probably using the Twilio API. If you get some sort of credit card charges, things like that, you’re probably using some API from Braintree or Stripe or anything like that. And there’s thousands more. If you’ve ever logged into website using Facebook and knew who your friends were, that’s an API.

So an API is structured way to get data between two websites. It’s usually accessed to via code. So people who are a technical or semi-technical would use them to either build workflows, build websites, things like that.

My company which is an API company, still a meta but you know, we probably use 40 or 50 different APIs to varying degrees, levels. And the reason I love APIs because I’ve always loved dev tools. And I’ve always loved things that make it easier for people to build startups. Like, I said, there’s not a single company out there that doesn’t use an API. And on top of that, there’s probably not many companies that don’t have some sort of API. Maybe it’s a big public API, like tripe S Twilio. Remember, it’s a smaller API that you know, only two people get access to, but it’s transferring data between to partnerships or things like that.

Andrew: Okay, so I told you, I think the first time that I really got excited about an API was when I put Wufoo forms up on my site, and they happen to say, “If you want to charge people, you can just put in an API key from I forget who it was, PayPal, Stripe, whatever.” Just put it in here. And then we’ll turn your form into a credit card processing form, which seemed like magic at the time. Why would I even need a good documentation in order to do that? Was the documentation coming into play with that?

Gregory: Sure. So documentation is not for you and in this situation. Documentation before the people who worked at Wufoo, who implemented the Stripe API. So, now, traditionally, let’s say, you know, 10, 15 years ago, Wufoo to build this feature out, it would have been incredibly hard for them. They would have had to call MasterCard and Visa and set up deals. Or they, you know, few years later, they would have had to use like a clunky provider that I couldn’t even name anymore because they’re just these gigantic, horrible companies that have all gone away. They have to figure out some way to get your credit card.

Then Stripe came along, what they said is, “Okay, we’re going to make it really easy for developers to charge credit cards.” Basically, an API, this is going to really dumb it down. But it’s almost like a website that you can interact with. It’s a URL that you can like, talk to the computer will talk to, and you would include your API key which you just mentioned, and a bunch of data. You’d say, “You know, I want to charge this credit card number with, you know, this $100, etc.” And you’d write this on code and rather than having to use this like gigantic clunky system or figure it out, you get a really nice API.

So the programmer can write, instead of having to like figure out how to interact with MasterCard and Visa’s like servers, which it’d still be an API, but much more complicated one. What Stripe did was they made it really easy and nice. So that it was just like writing code. You kind of make a call and it calls to a different server. It does all the work in the black box, and it comes back and says, “Yep, the credit card was charged.” So you wouldn’t actually use the documentation. You know, as Andrew who’s using Wufoo, what happens is . . .

Andrew: But Wufoo’s developers would use the documentation to understand how to interact with Stripe and make it easy for end-users like Andrew to use the features. And if it’s not documented well, then Wufoo’s is less likely to either use Stripe in the first place or if they do to not do a good enough integration for me to get excited. As an engineer.

Gregory: I mean, Stripe said, gigantic use case of why API documentation is amazing. Good developer experiences win. Because for a long time, people had this mindset of developers will figure it out, because developers are very good at figuring things out if they have to. But what Stripe kind of figured out in Twilio, and a bunch of these awesome developer tool companies that have come along is that yes, developers can figure things out. But they just much rather a nice experience as well. They’re still writing code and still way more complicated where like, you know, you wouldn’t be able to do it, maybe, but that’s getting easier and easier. Companies like . . . are you familiar with Zapier by any chance?

Andrew: Yeah, of course.

Gregory: Okay, so what Zapier does is Zapier kind of, if you look at the name, it’s Z-A-P-I-E-R and has the word API in it, so the website doesn’t mention APIs at all. But what they do is they sit on top of APIs. So they’ll do something kind of like Wufoo does as well or did as well, which is they’ll look at the API, one of their developers will figure it out. And they turn into like a bunch of forms and connectors and stuff that you can use just kind of an abstraction on top of an API. But APIs don’t really used for just that, like an API would be really useful for you. Yeah.

Andrew: Yes, sorry. Finish that thought and then I want to come up to one more question will go into your story.

Gregory: Definitely. So I think APIs are really good for let’s say that you wanted to reach out and do an interview with anyone who just got funding the past month that’s, you know, your new podcast way of finding awesome new people. You could go to CrunchBase every day and check and just kind of refresh and all that. Or you could use an API. And the API would be a URL you could go to that would have structured formatted data that would be updated every day or whatever CrunchBase does. And then you can kind of build a script that like went through it was like, “Okay, I only want to talk to people that I haven’t talked to yet.” So you can like filter people out and all that. And it’s basically just a way to send data back and forth or have another thing, create actions and things like that. But it’s kind of a programmatic way to let another service running some sort of code or [transfer 00:08:45] some sort of data.

Andrew: Final basic question. Why can’t they just write this in a WordPress set of pages, or a Google Doc? Why do they need to ReadMe? Why do they need your company?

Gregory: Yes. So why use us instead of doing documentation another way? So there’s a lot of ways to do documentation. A lot of people build themselves. The really nice thing that we can do is that we make it much more interactive. We make it so people can see different things based on who they are. So if you were to use WordPress, and you could hack this together a little bit. But we actually show error log, so if something goes wrong, we help you to bug it. You have a support question, you can ask a question. We let you play around the API in line.

So, like, let’s say that you know, Andrew, you want to start picking up programming using the Stripe API, you go to our site, and I’d see a code snippet and you could like modify it around the site and get exactly what you want. And you can copy and paste it over. We show API keys. We help people get started on. So you definitely do a little bit with WordPress or something like that. But we kind of make it interactive and think about documentation very differently than like static WordPress?

Andrew: I got it. So, in fact, I’m on your website right now. By the way, didn’t it used to be

Gregory: Yes.

Andrew: It was.

Gregory: We purchased the .com. When we raised our series A, we did the .com. It was a little bit of negotiation, but it was $170,000 was what the cost was for the .com.

Andrew: That’s a great price.

Gregory: Not cheap, but not bad.

Andrew: It’s a great price. I was going to correct my team and say you guys got it all wrong. It’s got to be .io. And then I realized, oh, now they’re redirecting to .com. So the homepage does say, “Beautiful, personalized,” not documentations, but “interactive developer hubs.” So, now, it’s more than just the API documentation. I see. It’s a whole experience. You are a guy who used to go to Y Combinator events and take notes.

Gregory: Yes.

Andrew: Which events and why did you take notes?

Gregory: Yeah. So first year was out of boredom? So maybe back in 2011, let’s call it they had something called Startup School. And it was a conference where they had a bunch of really awesome tech people. So, like, Mark Zuckerberg used to always speak. You know, Reid Hoffman. There’s a ton of . . . Don’t quote me on that one but there’s a bunch of like really great people each to speak. I saw like the Airbnb founders. I saw just a ton of really amazing people. And I just started doing doodle notes for myself and I published them and they got popular there on Hacker News and kind of became my thing for a few years where I just started doing doodle notes of these like amazing people.

And the thing I really loved about startup school and YC was the thing, that the prompt they gave people was not, you know, cocky and brag or market your product or anything like that. It was going to push people to talk about the lowest points when things seemed really bad. I remember a talk by I live with Brian Chesky from Airbnb, who did a great job talking about kind of the, you know, everyone knows that now the story about like, the cereal boxes where they, you know, we’re almost out of money and they were, you know, selling Obama O’s and Cap’n McCain’s in order to make enough money to scrape by, stuff like that.

And the thing I really loved about it was that I used to go to conferences. Listen, people talk all the time, and some people were very open, but a lot of the most successful people have kind of like gone back and retrofitted their experiences. They go back and they’re like, “Yes, I knew from the beginning that Airbnb was going to be huge.”

And the nicest thing about Y Combinator to me was that most of the companies that talked, they either went through YC or they were friends with someone from YC early on and, you know, the people who put on a conference could kind of call them on their bullshit if they went back and were like, “You know, we knew from the beginning that Airbnb was going to be a trillion-dollar company.” And I kind of always really liked that. I kind of I like that view of startups as opposed like, the very polished like, you know, here’s our origin story type stuff.

Andrew: You know, so I went to the website that you put up, I happened to click on Jessica Livingston just randomly the first page that came up, said most startups are shit shows. And so now you didn’t doodle . . . You didn’t doodle poop. But you did do to like this mess. This disgusting thing next to it, and you continue to do the design. The design of it was really interesting. Did you learn anything by sitting there and taking that notes and doodling and putting them together for other people? These people, didn’t they use to buy them?

Gregory: Can I . . . Yeah. So we did sell them back in . . . I . . . So there’s a talk by a guy named who I . . . he started a company called Watsi. And Watsi for people who don’t know is a nonprofit that does . . . it was the first nonprofit at Y Combinator and it’s a high impact, low-cost health care for people in third world countries. So, basically, it’s not to belittle it. It’s kind of a Kickstarter for health care and not in the U.S. but people with like cleft chins and things like that where, you know, they could . . . it’s for $100 you can change someone’s lives.

And I just fell in love with the story. Like he talked about how he was in Costa Rica working for I believe it was the Peace Corps or something like that, and I building houses and he’s kind of like, just wanted to help and came back and started the company and I just absolutely loved the story. So I started selling the book because I wanted to you give the money to Watsi. So I didn’t make any money off it. I sold it and I and donated the money to Watsi and that’s how I met Chase. I end up working at Watsi for a few months.

And I got a kind of fired because ReadMe was starting take off and like you can’t do, you know, burn the candle at both ends anymore. And I was like, I just love Watsi so much I didn’t want to leave, but they’re amazing people and they kind of really inspired me to turn into a book and all that. And that’s what I got out of it. Maybe not advice as much but I met some amazing people through it. Some of my closest friends.

When I raise money, people had bought the book already. It was the best thing I’ve ever done early in my career was . . . I didn’t do it for any reason other than I was just kind of bored and you start doodling it, but . . .

Andrew: Name some people. Who are some of the people who ended up investing in or supporting ReadMe because of that?

Gregory: Yeah, so I . . . well, to go through the kind of like Y Combinator stuff, when I interviewed, I knew a few people from that book that we interviewed in the same day. And SV Angel invested because I mean, at the end of the day, they invested not because I wrote a book but, you know, one of the partners there I happened to know because of the book and they reached out.

Andrew: Which partner?

Gregory: It was Abram Dawson if you know him. So he’s an associate there when I met him through SV Angel and all that and I met through him through that and that was perfect. And like, again, they didn’t invest because of that. But they that was how I kind of like, you know, got my feet in the door.

Andrew: Created familiarity that allowed you to get in. You were telling our producer, I was looking for my trillion dollar idea in a bazillion dollar . . . like you were really looking for something really big. Can you give me a sense of what you were looking for before you realized the power of ReadMe?

Gregory: Yeah, I am . . . so what happened was I didn’t really think that way. I loved dev tools. I wanted to build this product that would help make APIs easier to use.

Andrew: But I mean before. It seemed like for a long time and you were thinking, I need to find a giant idea and have these small tinkering projects. At least that’s what I’m getting from my team.

Gregory: Yeah. So what happened was I applied to Y Combinator with it. I did not get in.

Andrew: With what?

Gregory: Because one of the reasons was market size and things like that. I was like, “Okay now, I need to like go for a bigger idea.” Something so I tried a bunch of random things in construction and stuff like that, because I kind of had in the back of my mind like, “This is not going to work this. This dev tools company is not going to be able to be a big company.”

Andrew: It was always a thing that you were . . . it was a thing that thinking of for years before you officially launched it. You just didn’t think this is big enough. Am I right?

Gregory: Yeah, exactly.

Andrew: Oh got it. Am I coming through clearly, by the way? It feels like maybe my audio is not coming through as clean as it should.

Gregory: I think I can hear you. Can you hear me?

Andrew: Yeah, I can. Okay. So you went after the construction industry because you said this is a huge space. I think I could find a big idea. Y Combinator will love it. I’ll be able to grow this.

Gregory: Yeah. And I just kind of got worried about like, product-market fit. And just like, you know, finding a gigantic industry that I could conquer and all that. And because I want to build something. I didn’t want to like toil away at it. I didn’t want to be like a very small thing. I wanted to build something cool. And I think kind of what happened was, after a while, I started to realize I just didn’t care about construction, for example, and a lot of people really, really do.

There’s a company in my YC batch that does construction stuff, and they’re doing phenomenally well. But I never could have built that company because I just didn’t care, it didn’t excite me, like I, you know, I was bored after like a week or two of thinking about it. Whereas I kept going back to this other thing. And like, I think what I realized was product-founder fit is way more important than product-market fit. It doesn’t matter how gigantic or how small a market is, like people can build really great companies in very small markets and create markets. And then people can build tons of companies that fail and go miserably and it doesn’t matter that you know, the market’s gigantic.

Andrew: And the reason you came up with this idea was you had a need back in 2008. What was that?

Gregory: Yes. So I worked at a startup called Offbeat Guides, which doesn’t exist anymore. But I’m the founder was a guy named Dave Sifry. He had started Technorati if you know them, and a few other cool companies. And we were building an API, and it just felt so obvious that this should exist. APIs have been around for, you know, probably 30,40 years. But at this point, they’ve been pretty popular back in 2008. And nowhere near as popular as they are now but still pretty popular.

And I ended up doing something you said WordPress was kind of crappy, and I hacked it together in like two days and it wasn’t very good. And it’s kind of got behind . . . So think about something about how there’s so much we could have done had we put a little more time and effort into the developer experience.

Now, Offbeat Guides, this company that I worked at, never would have succeeded if the API was good or not. Like it didn’t matter for them. But around the time, I was starting to see like other companies like Twilio and Stripe that came out and they built these beautiful, amazing developer experiences and kind of showed that, you know, the most valuable thing is developer love. And kind of whole saying around, like, I’m sure you’ve heard it a bunch of times, like the whole, like, you know, on a gold rush, sell pickaxes type thing.

APIs were starting to be really big because, you know, there’s hundreds and hundreds and hundreds of people starting companies and they do the same thing over and over again. They set up, you know, text messages and they set up emails, they set up, like sending emails, they set up charging credit cards, they set up authentication, they set up, you know, there’s dozens . . . you know, when you get an email address, and you turn it into someone’s name, things like that. Like there’s, there’s thousands of companies out there all doing the same thing over and over again. And it’s kind of where an API comes in. APIs kind of come in and start to replace developers writing the same code over and over again. So rather me sitting there and writing the code that, you know, a thousand other people have done, I pay $5, $10 a month, or one cent per call, or whatever happens to be and I don’t think about it anymore.

Andrew: You let them do it.

Gregory: Exactly. And APIs have become the building blocks of startups over a few years. Like I said, there’s not a single company out there that’s not using, you know, at least 15 APIs I would imagine.

Andrew: So, right now, you’re incredibly eloquent about it. I’m actually literally, like, trying to stop you for a moment to do a sponsorship message. But you can’t because you’re so passionate, and you’re speaking clearly about a complicated topic. I wonder why you weren’t able to convince Y Combinator that this made sense. And let me pause there for a moment. I’ll talk about my first sponsor, and then we’ll come back in and understand what happened the first time you applied to get funding and support from Y Combinator.

First, I want to talk about my first sponsor and only sponsor in this interview, it’s a company called Toptal. Greg, why don’t I ask you since Toptal is a place to go and hire developers, what advice do you have for someone about how to find developers? What technique do you use to figure out who the right developer is to work with?

Gregory: I thought you were going to say fire developers. That was going to take a weird turn. So I think the way that I look for people is I look for people with curiosity. That’s the number one thing I care about, are they curious. Can they get excited about something? You know, I always ask people, what’s the coolest thing you’ve ever built? A lot of people will give me a programming thing, something like that. But like people will say stuff like I built a table or things like that. And if someone can get excited about something, that means they can probably get excited about my startup. So that’s where I look first, curiosity.

Andrew: All right. One of the best things to think about when you’re looking to talk to a Toptal developer is curiosity. Actually, here’s the way it works with Toptal, Greg. You go to them, and you say, “Here’s the problem I have. Here’s what we’re working on. Do you have somebody who’s dealt with a problem like this before?” They will put you in with three different people, or sometimes even as few as two and say, “Here they are.” And it will often be the perfect match because they’ve spent a lot of time getting to know you. You’re saying at that moment, we want to know what have they gotten curious about on their own and excited about?

Gregory: Yeah, I think so. That’s kind of how I end up at every one of my jobs. I was way woefully under-qualified for every single one of them, except that I showed excitement and I just cared and curiosity and all that. And I think that’s how I you know kept getting jobs that were way out of my league and found amazing people that were way, I don’t say under qualified but you know, I wasn’t hiring from these amazing places. I just found amazing people who were just sitting right there in front of me and I look for curiosity.

Andrew: All right, bring that over to Toptal if you go to that’s to Wait, you’re going to get 80 hours of Toptal developer credit when you pay for your first 80 hours in addition to a no risk trial period. Go check them out All right. What happened with Y Combinator?

Gregory: Okay, so that’s a great question. I think that what happened was, I was not nearly as articulate. I think that there was a issue where I didn’t understand why I was building it. I was a programmer and a designer and I liked both those things. I knew there’s something there. But I was talking about it from the perspective of someone who didn’t really know the market well, didn’t really know what was going on. But that all being said, I don’t think that was why we didn’t get in. I think the reason was that we didn’t have customers.

And I think that any VC, most VCs will feel very similarly is that they might say, that’s a bad idea, or it’s not going to work. But if you say, cool, but we have, you know, this many customers, it changes their minds pretty quickly. So I think the only real . . . well, there’s two real differences. One was that I, you know, I did have a little understanding by the time we actually launched, but I think the biggest difference was, by the time we applied the second time, I had customers and it kind of changed the conversation.

Because, you know, let’s say you’re asking me a question. You’re saying, “Why will people pay for this?” And I say, “Well, I think they’ll pay for it. Because I think they’ll, like . . . ” If I say that, then you’re like, “Well, I don’t think they will,” and it gets shut down.” And then all of a sudden we spend 10 minutes arguing and you believe one thing, I believe something else, and that’s where . . .

But if you say you know someone paid for that, I say, “Well, you know, our first customer was, you know, Box and they paid for it because they really liked that they didn’t have . . . ” And I go into that then it just changes the conversation so completely that it’s not here’s what I believe, it’s who cares what I believe. People are already paying us for it. So I think that was the biggest thing. I applied because I was a little burnt out at Mozilla. And I just wanted to like get into building a startup. And we applied with just an idea and didn’t have any money or anything like that. At the end of the day, kind of a little bit of money goes a long way and as far as kind of proving yourself out, I think.

Andrew: The final interview with the head of engineering at Mozilla, he asked you an interesting question. Do you remember what that was?

Gregory: Yeah. It’s a pretty standard question. I think it was less the question and more the follow-up that meant something to me. The guy who interviewed me, Mike Morgan, who’s now Director of Engineering at Etsy, he asked me where I wanted to be in five years. It’s a pretty standard interview question. I’m sure everyone here has been asked that. But the difference was, you know, he pushed me, and I said, “I’d love to start a startup someday,” and I talked about that. And he was like, “What do you want to do?” He pushed me and I was like, “I don’t have an idea.” And he kept pushing me, and then I start talking about, like, how I just thought that there was something about API documentation that really, I could do something awesome with it.

And I started going on about it, and at this point I called it live docs. I made up the name on the spot and all that. And I was talking about it and, you know, that was the end of the conversation. And then he called me back a few days later, whatever and offered me the job. And it was no small part due to that, due to the kind of just me having this kind of weird ambition and interest in something.

And I think most people, when they answer that question, they’ll say, like, “Oh, I want to be an engineering manager, or I’m not sure, or I want to improve my skills or whatever, and that’s something I really want to do in five years, or within five years, or around five years.” And they kept checking in for a few years while I was at Mozilla. You know, one of the things he said to me that I say to every one of my employees is that he knew I wasn’t going to be at Mozilla for the rest of my life. I know that, you know, none of my employees are going to be at my company for the rest of their lives. I want to make sure they leave closer to their goal than when they came in. And that’s a huge thing that I look forward and try to make sure that not only are these people someone that, you know, I want to work for me, but that ReadMe can help them kind of grow in the right directions.

And I just really appreciated that.

Andrew: Did it help you?

Gregory: And it was kind of really the first time I had an amazing manager that, you know, really cared about career growth and all that. And it’s why I end up working at Mozilla because I had a few other options. And I picked Mozilla because it felt like the right fit because of that, and they were true their word. And that was exactly five years after that, like, to the day, one day off. We got our first TechCrunch article about ReadMe so it wasn’t the most important milestone we’ve ever had, but it was pretty good, you know, box that in.

Andrew: And it helped you, for them to check in on you, for him to say, for Mike Morgan to come in and say, “How are you doing?” It pushed you to continue?

Gregory: Yeah.

Andrew: To do what?

Gregory: I don’t think it’s . . .

Andrew: Were you actually building?

Gregory: So I think it was less about, you know, pushing me just kind of making sure I was doing it. But, you know, at one point, a few years into being at Mozilla to [inaudible 00:27:14] product management, that’s something I never done before and wanted more experience in. And so I think it was less the checking in and just bugging me, and more the giving opportunities that fit what I wanted to do. And while I was at Mozilla, I worked on a lot of developer tools, which is very similar to what I’m currently doing. They did a really good job kind of helping me find a bunch of things that will kind of help me level up over the next few months.

Andrew: Okay. And so Y Combinator first round, you don’t have anything. They reject you. This is stunning. You remembered the rejection letter by heart.

Gregory: I don’t know if I remember it exactly by heart, but I definitely remember a lot of the words I use and all that. So, yeah, I definitely remember it because it was big. I think that’s another problem, was that . . . This is some pretty obvious advice in hindsight. But the difference between the first and second time I applied to YC was the first time I did it, I needed YC to succeed. If YC didn’t come through and invest in us, you know, there was nothing to do and I just was going to walk away, which I did do.

The second time, though, by the time we got in the room . . . So I put up, like, a huge amount of way too much emphasis on this YC thing because I was like, these are the people who are going to make or break me. The second time I went back it didn’t really matter. If we didn’t get to YC, it would’ve been fine because we had customers, things were going well. I didn’t expect them to make my company for me. It already existed.

And I think, you know, this is true about any VC or any relationship to a certain extent is that, you know, the more you need it, the less likely you are to get it. So I think that was, you know, why the first time mattered so much to me is because it was a make or break thing for us when it shouldn’t have been, because as we got bigger and we started, you know, making money and all that, YC kind of melted away as far as its importance goes. And I still do YC and I love it and I have nothing negative to say about it. It just was less of a deal-breaker for the company when we actually did it.

Andrew: Do you remember your first customer?

Gregory: Yes, I do. I saw him at a bar about, in San Francisco at a press club, maybe about a month ago. His name is Derek. He worked at a company called Notify, which got bought by a company called Kissmetrics if you’re familiar with them. And he’s still there. And, yeah, he started using us before . . . he had Stripe set up and we couldn’t charge him. So he started using it and he’s like, “How much does it cost?” I was like, “I don’t know.” And, like, don’t worry about it and he bankrolled me money or PayPaled me money, I guess, so that was our first paying customer.

Andrew: Why? What attracted him to you? What did you have at the time and why did he want it?

Gregory: Yeah. So I think that’s why I kind of really got into building renews. It’s because I started talking to a bunch of people about it and I talked to a lot of people about a lot of ideas on both sides of the equation. And I think there’s a gigantic difference between someone saying, “Oh, it’s a really good idea,” and, like, oh, that’s a really good idea. Like, if you do it enough, you start to realize that sometimes a lot of times people are bullshitting you or they think it’s a good idea but they’ll never actually use it. It’s when people started being like, “Well, can I use it now?” that I was like, “Oh, okay. I’m onto something here.”

And the general idea, like the high-level idea, which is that APIs are really important. An API should be easier to use. That has been from the day I first had the idea in 2008, that’s been, you know, the mantra. But what’s changed a lot is kind of the approach to it. Like, should it be a marketplace for APIs where, you know, you go to something like GitHub, and it’s all APIs, or should it be more, like, a WordPress type thing where it’s installed. But, like, there’s a lot of different, like, ways to approach this. And there’s a lot of companies that do API tools.

And it was . . . I kind of like . . . Every time I talk about it, like, people would be kind of excited. They, like, understand the idea. They go, “It’s cool.” But, like, once I kind of hit this, like, perfect little, finding the place in the market where I should be, people started getting really excited about it. People started to say like, “Can I use it now? Like, how do I sign up for it?” We just had this problem last week that we wish we could solve that exact way and the feedback started changing a lot for me. The things I was hearing from people was very different than it had been before and that’s why I knew that we’re kind of on to something and started pushing down the stretch a little bit more.

Andrew: And then how did they even find out about it?

Gregory: So I did a lot of freelancing around that time. I worked for some, you know, big places like I worked for Greylock for a while. I worked for the Warriors for a while, like a bunch of random places, a lot of startups you never heard of. And I just kind of had a gigantic network of people that I would just talk to about it. And I tried to find developer or freelancing jobs that were very similar to this, so I could kind of like get a little experience. And I talked to people and see what they needed. And it was a combination of that. It was a combination of I learned from these jobs. And also I kind of used these jobs as a way to be like, you know . . . I would never say, “Should I do this?” But it was kind of talk about it, and if they got excited, then I kind of knew to go further on that.

Andrew: And it was your testing and in one of those conversations . . . So one of those conversations led to your first customer. Do you know who this guy Daniel [Phone 00:32:16] is on “Hacker News”?

Gregory: I don’t think so.

Andrew: He’s the first person to post anything about as far as I know. I think he even scooped you on it.

Gregory: I do not know him. No. I do also know that Product Hunt, we also got a scoop down as well. And that was not fun getting a text message being like, you know, Product Hunt and we want to launch, you know, many months later. And I freaked out about it, and it worked out fine. I was scared, and I was like, “There’s, like, 1,000 features we haven’t done yet.” And it’s the best thing that’s ever happened to us. So that was the guy, Jack Smith, was one who kind of stole that and posted that before we’re ready, but it worked perfectly, so no complaints.

Andrew: Jack Smith was huge. I don’t know if he still is on Product Hunt. He’s the founder of Vungle and, like, a bunch of other companies, super-smart guy. Do you know him or did he happen just to come across your stuff?

Gregory: I’ve never met him. So the reason we got popular before . . . because we got a little popular before the product was launched, which was back in 2015. I was messing around and I designed this owl mascot. And he’s our mascot. His name is Albert now. And I thought it’d be really clever on the login page, when you type out your username, he just like appears to the side. But then when you tap the password field and start typing, he covers his eyes so we can see what you’re typing. And it’s been on Twitter a few times since then where people kind of, like, copied and all that. But I thought it was, like, this really cool idea and I built it before we even launched. And someone saw that and posted on Twitter. It kind of went viral. And I think that is how Jack must have found it because there’s no reason why anyone should have found the site otherwise. But, like, pretty much every designer I knew was tweeting about it, and I think that’s kind of how we got a little viral earlier on.

Andrew: Help me get in your head, Greg. What does it say about you, that for a login screen, you have to take your owl and have his eyes kind of cutely cover. I mean, have his hands, his wings, I guess, covers his eyes cutely while people are typing the password? Why go the effort to do that? What does it say about you?

Gregory: I love these, like, little big details. And that’s actually where this thing got popular. It was a website called Little Big Details, but I just love adding whimsy and little bits of detail to the smallest things. One of my favorite . . . so a lot of people love Steve Jobs, for example. My person is Walt Disney. He’s always been since, you know, I was really young. It’s not that I loved Disney movies. It’s not that I love Disney rides. Like, I love Disney World and Disneyland. I just love the little details. I don’t care . . . So I don’t love, you know, Space Mountain or anything like that. I love things and one of the things I really loved about it is how much effort and work they put into kind of the onboarding flow. So, basically by that, I mean, you know, either walking down Main Street or getting onto a ride, for a while, I got really obsessed with Main Street in Disneyland and Disney World because there’s just so many little details that you don’t notice but . . .

Andrew: But I’ve never been to Disneyland. And even when I went to Disney World as a kid, I didn’t really notice anything.

Gregory: Yeah. And it’s subconscious, and that’s the whole point. This is a little more in your face, obviously, an owl that looks at you and everything. But, like, I think the biggest thing that Disney do is realize how important the little details are that whether they’re conscious or subconscious that really get to you.

Andrew: Do you have an example of one that stood out? Yeah, like what?

Gregory: Yeah. So, when you walk down Main Street going into Disneyland or Disney World, there’s a lot of little details that if you go now and look at it, you’ll be like, “Oh, it’s really obvious,” but it’s supposed to be, like, the rolling beginning credits of a movie. So you can’t see anything. You start walking down it on the sides. There are windows. And the windows have things, like, you know, John’s flower store and things like that. But all the names are people who built Disneyland and Disney World early on. So it’s kind of, like, opening credits that roll as you walk down Main Street.

There’s no way to drive up to Disney and just walk in. You have to drive, park, and it take some sort of transportation, either a boat, a monorail, train, and something like that. There’s thousands of these little details that go into it. As you kind of cross into different parks, they have . . . You know, they use different . . . They change the flooring, so your floors lookup. And they have something called a weenie, which is, like, in front of you, which is that gigantic thing that draws the eye and kind of, like, makes it really obvious you’ve entered something different.

There’s a ton of little details like this. And there’s a show on Netflix, or on Disney Plus that I haven’t watched yet but called “Imaginary Story,” which I think, you know, it goes through a lot of this if anyone’s looking to learn more about it. But it was just that. I just didn’t want a login form that was drab because I wanted someone from the beginning, from the first second they logged into ReadMe to know that someone cared. Someone thought about every little detail. And you’re not going to go and be like, “Oh, ReadMe is amazing because it has an owl.” But you might think, “Oh, if they care about the login page, they probably care about every little detail going forward as well.” So that was a big reason why it’s important to me to do that kind of stuff.

Andrew: How did Vox find you?

Gregory: That’s a good question. I think just “Hacker News.” I think I posted on “Hacker News,” and I think they just reached out to do a comment on it.

Andrew: I have to be honest, I was actually kind of setting it up because I thought the way they found you was that they saw your logo on someone else’s documentation. They looked at someone’s documentation. They said, “This makes sense to us. Hey, ReadMe. Let’s go check it out,” and then they signed up.

Gregory: Of the thousands and thousands of companies that use us, you picked the one that did not find us that way because everyone else after that found us that way. Box using us led to Yammer, which led to a bunch of companies like Lyft and Trello and all these big companies. And almost 100% of our growth comes from that. It comes from people seeing our logo.

Andrew: Oh, got it. So, because people saw it on Box, then they started using it. Got it. Now, I see how it works.

Gregory: You can still picked patient zero. Yep, you picked the one company that was the . . . and not going to be the answer for.

Andrew: And that gets you a lot of virality. What else do you do to get people to find out about ReadMe?

Gregory: That’s really it. I mean, we do . . . We just hired somebody to do marketing. We’ve always done some ads and stuff like that. We do content a little bit. And we’ll have to do more of that as time goes on but it’s always kind of paled compared to how many people see us because we sell to developers, and then those developers that we sell to they also have used a ton of APIs. And because we do the documentation for so many APIs, that it’s a pretty easy sale. It’s kind of like how GitHub’s a little viral in that sense. You’re not going to see many Google ads for or, you know, Facebook ads or anything like that for GitHub because we’re already kind of where the developers are.

So that was something I didn’t realize early on, but I’m still ecstatic about was that we’re selling to the same people that our customers are selling to sell. So most people have . . . they’ve never heard of us. They’ve at least used an API that’s hosted on us. And what happens is it comes down . . . Let’s say that, you know, Andrew, you’re building an API for Mixergy of, like, a list of all your, you know, people that have been on the show. And, you know, you’re like, “Okay. I want to document this somehow. I could write it myself. I want to see what other companies do.” And you just pick a few your favorite APIs in the back of your head, and you just go to them, you’re like, “How did they build this?” And you’re a developer, so you kind of dig into stuff. So, even if the logo is not on the site, you know, you can, like, view source or something like that and it.

Andrew: Yep. I do that all the time.

Gregory: Yep. And then you start seeing, like, in theory, if we do our job right, you start seeing like, oh, the ones I really like are all hosted on ReadMe. So pretty much everyone who uses us is kind of just word of mouth.

Andrew: You know what strikes me. You’re a guy who got really well-known in the startup world, in the Y Combinator world. And still, even though you met all these potential co-founders, even though in a lot of your doodles, I saw references to co-founders. You didn’t decide, “I’m going to get a co-founder, somebody to help me out with this.” Why not?

Gregory: Ignorance, I guess. So I did have a co-founder going through YC and it was . . .

Andrew: You did?

Gregory: . . . the biggest mistake I had. It was a kind of, like, a shotgun wedding. And he’s a really good guy but we just had never worked together. And it was tough. And that’s my biggest regret. Like, I don’t give startup advice often because, you know, I’m still figuring things out and all that. But the one advice I do give people is try to find someone to work on stuff with because it’s tough.

So my mindset was a little bit more because I started the company without him by myself. I launched by myself. We had our first customers by myself. And I actually got a co-founder because I knew that it was probably a good idea, but I didn’t . . . If I had known how important it was, I would have spent way more time on that because my mindset was, “Oh, I can do the programming. I can do the design. I can do everything.” And it was such a naive way to look at it.

What I didn’t know how to do is how to build a company, how to do sales. And since then, I found amazing partners and all these, you know, things I just mentioned, that aren’t co-founders, they’re employees. But, you know, I treat them, like, co-founders, and, you know, I trust them that way. But I really wish I realized that when you’re building something like this, you’re building two things at the same time. You’re building a company and you’re building a product. And they are very intertwined, and you can’t . . . There’s very few amazing products out there that have a shitty company and there’s very few, like, amazing companies that have a shitty product. They’re very intertwined. And I always joke that I could, like . . . if you blindfolded me and dropped me off at two competitors like Lyft versus Uber, I could probably guess which one I’m at just by the office and the people and talking [inaudible 00:41:42].

And that’s not saying that I like one or the other more. It’s saying that I just think that the company and the product are very intertwined, but they’re two very different things at the same time. And I wish I’d realized that sooner that I spent all my time building the company as opposed to the product form most product’s point and I love it. But I didn’t think that was going to be the case when I started company. I kind of always thought it was like, we’re building a product and building a company is a lot harder than building a product, I think.

Andrew: You know what, Jason Fried the founder of Basecamp has been on Mixergy a bunch of times with interviews. He did this one, what we call a master class here that it’s called “How to create a calm culture.” And what he’s basically saying is, I’m going to show you how to create a company because what you want to do is create a product and you don’t think more about, like, the internal structure. You think about iterating your payment page and you think about iterating your landing page, you don’t iterate your company. And that’s what he focused on. He was just brilliant. For anyone out there wants to check it out, you should go to I think that’ll lead to it. I think it’ll lead to all the programs together.

Gregory: Oh, I’m sorry to interrupt on but every new employee, I give a copy of one of his books. I think he’s phenomenal, so I definitely endorse anything he’s ever written.

Andrew: I do too. And they’ve got their company culture document or there, what is it called? The operating manual to working at the company they’ve got a publicly, which is just phenomenal. I just love his writing. It’s so basic, so simple, so clear-headed.

Gregory: He reminds me a lot of, completely different messages, but of Paul Graham as well. Like, some of my favorite people are just very clear concise writers. And I wish I was more like that. They do such a good job of . . . Like, you actually watch them think and they say something in so few words, like all those books “Rework,” you know, “Getting Real,” they’re very easy reads. You can read them in an hour, probably an hour-and-a-half, but they’re just so thoughtful and clear, and have no cruft on them, and I highly recommend anything from Basecamp.

Andrew: Can we talk a little bit about the difficulty that you had? Like, you went through some personal issues. Was it last year and how that affected your work or what was going on? What can you say about that?

Gregory: Yeah. I would say that it was anything big. It wasn’t like, you know, anything gigantic happened. It’s just the ebbs and flows of starting companies is really, really, really tough. There’s really good times, and there’s really bad times where it’s very kind of lonely and you don’t know what you’re doing. And you don’t . . . Sometimes it’s really nice to just have a boss to tell you what to do. And you can just, you know, check out, whereas when you’re in a company, if you’re a little more checked out or a little sadder or a little just stressed out, it’s tough because it reverberates in the company. So, if you show up and, you know, you’re in a bad mood, kind of everyone just trickles down pretty quickly.

And the problem with that is, then it becomes like reverberating effect where it’s hard to get out of it. But the counter-argument is that you come in and you’re always excited. But then there’s like a difference between a delta between how you’re actually feeling and how you have to feel day to day and stuff like that. And I think a lot of founders, almost every founder, I know goes to this. I don’t think I know many founders who haven’t had some sort of, like, low point. And it’s usually a low point triggered by something bad. Sometimes an acquisition falls through or funding doesn’t happen or anything like that.

Andrew: What was it for you What was going on?

Gregory: I think we’re hitting this weird like, middle ground with a company where we were profitable and things were going well, and we were growing steadily and I was happy. I loved all my employees, but we just weren’t moving as fast not financially, but just product-wise as I wanted to be. Like some of the stuff I find myself talking about over and over again, for like two or three years and like, at some point I was like, “Shit, we haven’t built this yet.”

And that’s what kind of prompted me amongst other things to do a few things. One thing I did was because there’s a lot of depression that comes out of your metric for success being what’s called lines of code or, you know, designs made. Like it’s very tangible stuff I used to do for a job. And then when I started the company, have anything tangible. So one thing I did to rectify that was I love . . . I took a week off from work and I had gotten really into startup or into escape rooms. And I you know, I kept bringing my team to escape rooms.

We kept doing it over and over again, so built an escape room that was a San Francisco theme, so it’s called Startup Escape, it’s still running, and you have one hour to launch your startup. And it was great because actually got to do stuff. I got to write a code. I got to build something with my . . . I got to build like IKEA furniture. I got to like, wire together all these games. I got to create a ton of games some were logic-based, some were over the map and it’s this really cool tribute to startup culture. That’s also an hour-long game that companies can go to, so I was really nice kind of like, give myself something tangible to do.

Andrew: It’s an actual place?

Gregory: Oh, yeah.

Andrew: I’m on It’s an actual place that you created with real escape room and everything, here in San Francisco?

Gregory: Yep, I rented out an art gallery and [inaudible 00:46:48]. Yep. So not too far from you. You should do it sometime if you’re around. So, yeah.

Andrew: This just blows my mind. So you’re running this thing while you’re running ReadMe?

Gregory: So I hired a general manager pretty quickly after. So, luckily, the only thing I do now is or and for long, for a few years now has been I’ll pop in when somethings, you know, broken or I want to build . . . I have a new idea for like a new clue or a new puzzle or something. But yeah, and I tried to make it very like Silicon Valley, very San Francisco. So like, there’s five different tracks programming, design, marketing it and DevOps. And you know, when you doing the programming one, you have to program, it kind of feels like you’re programming.

With the marketing one, there’s a bunch of swag t-shirts, and there’s a clue that involves a Snapchat filter, and I have to upload stuff on Product Hunt and Twitter and things like that. For the product management one, there’s a bunch of books like “Zero to One” and like all the cliché startup books, and you just like use clues in those books and stuff like that. The goal is to make kind of a tribute to San Francisco . . . I’m sorry. The internal goal for me was I wanted to do something tangible. I want to actually build something unique, something because my job had been a little divorced from like this day to day actually make something.

And then a higher level, I wanted to do something that I thought people could kind of . . . because, you know, we’re talking about like startups are really, really fun. And it’s what I’ve always wanted to do. And I love the culture. And I think that they’ve gotten a lot of, rightfully so, but a lot of bad rap over the past few years. And I always want them to be better. And I don’t want to just kind of be like, “Don’t worry about it. Startups are fun. We shouldn’t care about stuff.” But I think they become . . . I miss the kind of like . . . I think sometimes we forget that we’re able . . . we’re going to get a ton of money to build exactly we want and like it’s fun, and I kind of want to build something that’s a little tribute to that.

Andrew: This is such a great idea. You get your team has $1 million in one hour. You need to work together to launch your startup or you know, to escape to get out of the escape room before your time runs out and your money runs out. You’re trying to do justice to this nice design on the page that when my mouse moves changes the criteria, but people should just go check it out at, really well done. You designed that homepage?

Gregory: Kind of. I did all the design except for I have an artist I’ve been working with, so I did the original owl on ReadMe, and then I started realize that there’s better people out there. So I found an artist named Paul Cox. I shouldn’t say his name because I don’t want people to hire him because want to get so much more from him. He’s amazing and so he does our . . . he took over our mascot at ReadMe. He did the artwork there. He’s such a phenomenal artist, and I use him for all my stuff now. Because he adds like whimsy and fun to everything I do.

Andrew: What’s the best part of having done this? I mean, you’re a guy who going back to when you were a kid in upstate New York. You were designing websites like that Disney fan site back in the ’90s. You wanted to build a company. You struggled. You failed. Y Combinator booted you or said no to you?

Gregory: That wasn’t that traumatically but, yeah, exactly?

Andrew: It was pretty bad. You ended up procrastinating for a little bit because of it from what I understand, right? It’s not easy to . . . you were part of the team in some ways. You wrote the notes that everyone was talking about. I found tons of references to that on “Hacker News.” And here you are. You did it. You’re doing the thing that you dreamt of doing. What’s great about it? Let’s close on a high note.

Gregory: So my five year anniversary of like getting a paycheck from ReadMe was last week. So that’s not five years from having an idea. It’s not five years from the first line of code. It’s, you know, five years from the first paycheck. And it’s been way longer than that, and I am more excited now than I was 5, 10 years ago. I get to work with every day more increasingly amazing people, whether it be employees, I get to work with name like a startup, I know someone there are many people they’re probably the CEO.

I get to . . . I’m friends with people that I used to idolize five years ago. And like that’s insane to me. Like if you told me that I’d be friends with you know blank, I won’t name drop, but like I’d be like . . . if you told me I could meet this person, I’d be like that would be insane someday and now I’m friends with them.

And I get to build. I just show up and there’s negatives, of course. There’s a lot of negatives but I get to show up and like build what we want to build, make what I want to make. Have people that believe in us whether it be investors, employees, customers, etc. and you know all the stuff that I talked about like Disney. I get to like, you know, I’m not making animated movies or I’m not making anything else and you know, I’m not doing entertainment, but I can kind of like bring those ideals to the job.

I have employees I love. Over the summer I went to one of my employee’s weddings and things like that. That was exciting. Like, it’s there’s so many amazing opportunities you get and then there’s like negatives too, but I would, you know, I got to build Startup Escape, it’s like a real-life escape room. I never done that otherwise, like, I’ve been incredibly lucky. And I think, you know, I go back, you know, I first had the idea of wanting to startup back in like 2008. And then 2010 in my Mozilla interview. Like I think it’s very, very different than what I thought it would be like. It’s nothing like what I expected, but it’s been way more fulfilling way better and yeah, no complaints.

Andrew: Usually, at this point, I tell people to go check out the website, people can go see if they want, but I’m going to suggest instead, if they really want to get to know you as a follow-up to this interview, they go check out your personal site, They’re going to have trouble with the spelling, but they can see it obviously in the show notes. Look at how the fricking guy where he shows you how he lived, the thing animates. Like the little fricking details. My favorite page on it is My Projects where I get to see all the things that you’ve done. I didn’t realize that you created the San Francisco subreddit on Reddit and you’re still actively moderating it. Are you done with that?

Gregory: I wouldn’t say it’s my proudest moment. But yeah, still the lead moderator of it. I did very little early on other than just kind of saw that Reddit was going to be big and registered it. But, yeah, I’ve been the moderator of that, the head moderator that for about 10 years.

Andrew: So a bunch of interesting projects, but it’s the little details. Now, that I know you, I understand why these details are the way they are. All right. I want . . . And you know what I found what I was talking about with Basecamp. It’s their company handbook, and people can see it at And I’m incredibly grateful to my sponsor, Toptal for making this interview possible. If you’re hiring developers, if you’re thinking about, if you know somebody who wants to hire a developer, do all of you a favor and go check out, Greg, I think we said it all. Did I miss anything?

Gregory: I think we got it. Thank you so much for having me on.

Andrew: Thanks for being on.

Gregory: Bye.

Andrew: Bye, everyone.

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