Special: Acquired x Indie Hackers

I've got new M1 MacBook Air. It's the first episode we're doing on it. Nice. Nice silent recording in the background. No, what do they call it on the pro? The active cooling system. Don't call it a fan. Welcome to this special episode of Acquired, the podcast about great technology companies and the stories and playbooks behind them. I'm Ben Gilbert, and I'm the co-founder of Pioneer Square Labs, a startup studio and venture capital firm in Seattle. And I'm David Rosenthal, and I am an angel investor and advisor to startups based in San Francisco.

And we are your hosts. As regular listeners know, we typically cover some of the biggest companies, those that IPO, see Airbnb and DoorDash last week, and the companies that get some of the splashiest press coverage. But today's episode is quite a bit different. In our conversation with Cortland Allen of IndieHackers, which is the largest community of startup founders, we dive into the stories of the underdogs. What happens when there are millions of people doing small business entrepreneurship?

How does the globally addressable market of 3 billion internet users open the door for the nichiest of products? And importantly, what was Cortland's lived experience of starting his own string of companies that ultimately led to starting IndieHackers and its acquisition by what is now the hottest private company in the world, Stripe? Yeah, man. Last one left standing after last week. No kidding. And a lot of people cannot wait for it to IPO soon enough. I can't.

That's going to be, I got to imagine our biggest episode of next season. Hopefully next season. When is this going to happen? Season eight, season nine. We'll see, David. We'll see. Well, as always, if you love Acquired and you want more, well, good news. We have the answer for you. The community of Acquired Limited Partners is now an army in the thousands. For those of you who aren't already a part of the gang, Becoming an LP gets you twice as many episodes, access to live events with us and other LPs, even in an all virtual 2020.

And most near and dear to David and my hearts, you have the biggest influence on what we cover in the show. So if you want to join, you can click the link in the show notes or go to Acquired.fm slash LP. All right, listeners, now is a great time to talk about a new partner of ours here on Acquired, Lagora, the agentic operating system that is redefining how the world's best legal teams work. Yep. It's sort of obvious that AI is going to completely change the legal industry.

I bet most of you listening have dropped a contract into some sort of AI chatbot out there. Lagora took that insight and asked the question, what if you really built something with that power from the ground up for the legal industry? So the founders did exactly what great founders do, operate with obsessive customer focus. They embedded inside a massive law firm for months. They sat with the lawyers just watching how the work really gets done. And that's how you get features that customers love, like tabular review, where you drop in a folder of hundreds of contracts and it pulls every key term into a grid a lawyer can actually work with.

Lagora's bet here is interesting. Since it lets each lawyer handle more complexity, any given person can increase the quality of their work and do higher value work. And this means that the pie can grow even as each individual task takes less time. And they recently launched Lagora Agent, offering greater intelligence and performance. The agent lets lawyers set an objective. Then it can handle the planning and the execution and delivery of the final product. Legal teams get to maintain full control and transparency since they're still involved where judgment is required.

And Lagora works where you already work. You can use it within Microsoft Word while redlining or drafting. The early Lagora numbers essentially speak for themselves. When they have a head-to-head pilot with their top competitor, they win 70% of the time. Lagora now has over 100,000 lawyers on the platform from 1,200 legal teams in 50 countries. And crazily, they went from 1 million to 100 million in ARR in about 18 months. Truly insane numbers. And that is the real test.

Plenty of things demo well, but the question is whether a busy associate actually reaches for it during crunch time. Or whether a partner trusts it before going into a conversation with a major client. If your legal team wants to check it out, whether you're a law firm or you're in-house at a company, you can learn more at lagora.com slash acquired and just tell them that Ben and David sent you. Okay, now on to our crossover episode with Indie Hackers.

Cortland Allen, welcome to Acquired. Ben, David, thanks for having me. So great to have you here. Our pleasure. For anyone who has not listened to your voice for the many hours that I have on the Indie Hackers podcast, obviously we're going to reference it lots and lots throughout the show, but go check it out. And very excited to be doing a crossover episode with you. Yeah, I'm excited to do this. People have been asking for a while for me to do an episode on myself, because obviously Indie Hackers is kind of an interview show.

I just tell other people's stories. And I've always been like, as weird as it sounds, like shy to do an episode on my own podcast. So congratulations on being the first people to convince me. Well, look, we are the Acquired podcast and you did that mega deal exit to Stripe. So how could we not cover the acquisition of the century? This is great. It's got like all the hallmarks of both of our episodes. We'll see how that goes.

Well, David, who is Cortland for listeners who don't listen to Indie Hackers or haven't participated in the community? Yeah. So Cortland is a former YC founder, MIT alum, and founder of a company that has been acquired by Stripe, all of which seems like it would fit very much into the acquired theme. But there's a twist. Just unlike the big go for broke, you know, we were jamming before we hit record here about the typical startup path that we cover all the time on this show is trying to build the new version of, you know, standard oil out there, except, you know, 10, 100, a thousand times bigger than the Rockefellers and the Carnegies could ever imagined.

Cortland is all about a different philosophy out there. The Indie Philosophy and, of course, the company that he started and what he runs within Stripe and the website and the community and the podcast is Indie Hackers. And Indie Hackers, I think, is really cool. We're going to get into it in this episode. It's kind of like if big tech and startups are the Rockefellers. This is the small business entrepreneurship of the 21st century. And I think it's really, really cool.

So we're pumped to do this. Yeah, you're saying Indie Hackers is not a big, splashy, go for broke story, David? I don't know. You're going to tell us. It's really not. It's really the story of, I like to think of it as the underdogs. You know, the internet's been around for decades. And I think the world is still kind of slowly waking up to how much it's kind of changed the game for just like regular people.

Everybody's connected to everybody. And you can reach literally millions of people, if you're clever enough, for pretty much zero dollars. And so people are creating these very tiny niche businesses that could never have existed 20 or 30 years ago. And in some cases, not even five or 10 years ago. And I think it's becoming possible to sit down in your living room wearing your underwear, whatever you're wearing, and just create something that's super valuable to your community and your customers.

And that's really kind of fun and fulfilling and challenging for you to work on as a person. And that makes you rich in the process. And I think that's pretty crazy to check all three of those boxes. So thousands of people are doing this today. And the question that I'm asking myself constantly is like, what happens when millions of people are doing this five or 10 years from now? Yeah, I think that's what's so cool is like small business entrepreneurship in the past was a great way to build wealth and do well, you know, for your family and for yourself.

But with the same or honestly, like less amount of effort now on the internet, this path exists that the wealth you can build, even by taking this path, is still so much bigger than you could build, you know, building a dry cleaning business in the past or running a restaurant or a lot bigger. Not to foreshadow our sort of playbook too much, but it does remind me that, you know, in a pre-internet era, the local small business owner was geographically constrained and they could, you could have a general store that sold everything, but it could only sell everything to the people in your town.

And obviously the sort of like large scale version of that is Walmart, but that is a very different type of business to run. With the internet, you can just do one thing in one niche, but you have a nationally, if not globally addressable market. And so I continue like Cortland from listening to your show. Every time I listen to an episode, I get smacked in the face with, wait, that niche is that big? And people find these crazy opportunities.

I just listened to the patio 11 episode and he was talking about bingo card creator. And I'm like, a bingo card creator could be a business, but like these niches are so deep or so wide or however you want to describe them. If your TAM is the 3 billion people with the internet, then every niche within that TAM can be on its own big. Hey man, Starlink's coming soon. It's going to be 7 billion. Exactly. If you have like a business that only appeals to like, you know, one in a thousand or one in a million people, you need to live in like a very big city to create a brick and mortar business that's going to survive.

But on the internet, like that turns out to be millions of people who can use, like your underwater bingo card creation, whatever it is that you're making, which means that like pretty much everybody can figure out something really specific that no one else is doing and kind of stake their claim on the internet, which I think is super cool. I hear the real estate is cheap too, though. All right. So let's get into your story. Okay.

Let's start way back before MIT. Your family and your mom specifically was an entrepreneur when you were growing up, right? So I had, I was just talking to Jason Calacanis about this on his podcast where he was talking about kind of opportunity, you know, can anybody start a company? Does everybody have an equal chance to do this? I think in a way like, you know, nobody, nobody's quite equal. Everybody's got kind of a different starting line.

And when I look at my childhood, like I had a very good starting line. I had two loving parents. They were very attentive. They were very devoted. We were sort of middle class, but very comfortable. And like you mentioned, my mom was an entrepreneur. She was always doing her own kind of crazy hijink startup, selling computers and stuff in the nineties. And my dad was part of like, like this elite team of like furniture makers. There's like nine of them.

And they each had a different role and they would make like crazy furniture for like celebrities. So he wasn't making like a ton of money, but he was doing something that he found really fun. He was like the furniture finisher. So he'd take like a, you know, ugly piece of wood and make it look like amazing. And I grew up like these two people in my life who kind of showed me that you can do pretty much whatever you want and like kind of scratch out a living.

Yeah. You can do this and like, it'll be fine. You can have like a good life, right? Yeah, exactly. You can have a good life. You know, like we were eating, we weren't missing meals. I had a bunch of other advantages too. You know, like I was an American. I was born in the late 20th century because of my mom's computer business that she ran for like a year or two before it crashed. Like we had a computer in the internet when I was in the third grade, like right after the web came out.

And so of course, like I was addicted to video games and like whatever I could play. But from the adult's perspective around me, they're like, oh, this is a computer whiz. You know, whenever I've got a computer issue, Cortland spends so much time on his computer, he can just like swoop in and fix it. So I was like doing all this IT work on the side. And of course, nobody ever paid me. I made zero dollars like as a nine-year-old fixing people's computers.

But I got a lot of positive encouragement because from my perspective, I was just like, you know, playing games and fixing bugs and stuff. But from like the average adult's perspective in the mid-90s, they were looking at like the tech boom and they were looking at Microsoft's stock price and the fact that Bill Gates was like, you know, mega rich. And so they would sort of pay me an encouragement. They'd be like, oh, yeah, you're going to be like the next Bill Gates.

Like, keep it up. And what was cool about that was, you know, I got to be like a little computer nerd and also see that like this really like old computer nerd was universally respected by like every single person that I ever met. And everybody told me that it would be a cool thing to aspire to kind of be that. So by the time I was like 10 or 11, I was like, OK, I want to be Bill Gates.

You know, I want to start my own company. I want to go to a good college. Like, how do I how do I get on that path? In some ways, it's like echoes of the Tim Sweeney story and Epic Games, you know, him starting out first with it was his older brother. Right. Right. Ben, that had a computer hardware business. And so he like went out to visit his brother, got hooked up with computers, got obsessed, then started like an IT consulting business after the lawn mowing business.

Nolan Bushnell, too. I remember when we asked Nolan about starting Atari, he was fixing TVs and not at all to put myself in the same category. I was fixing teachers computers in middle school as my I think I was making like seven bucks an hour. So sorry, I was dwarfing you there. But yeah, that's so many people's entree before they actually get into programming is basically just fixing stuff. Yeah. And I think it's important. Like I've taught people how to code in subsequent years.

And there's this kind of base layer that gets ignored of just like computer literacy, where the people who learn the fastest are people who just like they're just very comfortable if their computer crashes or has an error. Like they know all the keyboard shortcuts. They're good at Googling stuff. And if you have that kind of base layer of skills, it makes everything else much easier. So you're 11 or 12. At that point, you know that you want to go into a, you know, technical field or programming or computer science.

Did that ever deviate? Or was that pretty much like nope, laser focus from that point forward? Oh man, I had this like real embarrassing phase where like I was trying to choose between like, do I want to be Bill Gates or do I want to be Kenny G? Yes. So I had a saxophone. I was playing like a lot of like just corny contemporary jazz music. And luckily, luckily, the computer stuff won out at some point.

And after that, like I didn't deviate. Like that was 100% what I wanted to do. I had a ton of like just a ton of fun just like doing stuff in the 90s on my computer. Like a lot of support around me. And, you know, in one way, I think I had kind of like the world heavyweight champion of childhoods. You know, it was like really, really good, like really advantageous. But I also had some hardship.

Like my dad died when I was pretty young. I was in high school. And like for me, that was just like a huge wake up call. Like, oh shit, sometimes things get real. And like no one's going to kind of swoop in to save you. You have to kind of learn how to survive and make it through tough things on your own. And so I got like almost like kind of the perfect mix of like hardship and like encouragement and like privilege in a way.

And so, yeah, by the time I left to go to college, I felt like pretty ready to take whatever the role was going to throw at me. And also like pretty far ahead of the curve in terms of like knowing what I wanted to do. Like there's never a question like what major do I want to have? You know, what do I want to do after I graduate? Like I was always 100% certain what I wanted.

And I'm sure that tragic, you know, death in the family also forces a lot of early maturity that you have to take on sort of more responsibility or at least think about the broader context around your life than just yourself earlier than you otherwise would have. Totally. And like I think for me, the biggest impact was just like you kind of get like a floor. You establish like, okay, this is the worst thing that's ever happened to me.

And like I survived it. You know, like it was terrible and like all sorts of like bad side effects you wouldn't even think about. But like once you establish a floor, then like a lot of other things just don't look that scary. Like they don't look like that big of a deal. Like, okay, what if I start a company and it fails? Like, oh no, you know, like I'll go get a job. I'll go get a job.

Like nobody died, you know? So I think that's kind of what I got out of it. I assume that the computer, the love of computers and knowing what you wanted to do, getting out of the Kenny G phase, that's what brought you to MIT. The Kenny G phase was a good one to escape. Yeah. So I remember like really wanting to go to MIT. I somehow figured out that that was like kind of the best school you could go to if you wanted to be a computer scientist.

I had no idea that Stanford even existed. Like if I had known that and that it was in the heart of Silicon Valley, I probably would have tried to go there. And I also didn't know that like it was even feasible to just not go to college. Like if I had known that I could do that, like I probably would have just done that and tried to start some stuff. But I remember talking to my mom and asking, okay, like, you know, how do you get into MIT?

And she's like, well, good, good grades and study and apply. And like, hopefully they'll let you in. I'm like, well, what if they don't? And she's like, you just go somewhere else. And I remember thinking like how frightening that was. Like I got like one shot to do the thing that I wanted to do. And if I got rejected, that I would just be done. And in a lot of ways, like that was a much scarier thing than I think starting companies that like have the risk of failure.

Because like you can start a company a million times. Like if it fails, like there's no like, all right, you know, that's it. You gotta go somewhere else now. Like you can just keep doing it over and over again. Well, how many companies have you started now? Seven. Andy Hackers is my seventh attempt to do something that worked. And the only one that really worked. So yeah, I was going to say, so when you get to MIT, you, I think if I understand the history, you start applying to YC like regularly.

Yeah, yeah. I played a lot of times. So is this like a like every quarter thing? It's like register for classes, put in the YC app. Well, I was like a pretty bad student. I didn't understand like the idea of like, I just didn't really want to learn. And I thought all the stuff I was learning in my CS classes was boring. And so I spent a lot of time working on my own side projects. And at some point I discovered that there's this magical entity out there that will like give you a bunch of money to take your project and try to make like a company out of it.

So I got really hooked and I would spend a lot of time applying. I got rejected at least like two or three times. Had Dropbox already gone through YC at this point? At some point, at some point during like when I was in college, Dropbox like went through and Dropbox was also an MIT startup. So everybody on campus had like a bunch of free Dropbox codes and we had like a ton of free space and everybody knew their story.

So there's a lot of like positive encouragement there as well. Like, oh, you want to apply to YC? Like everybody knows what that is and thinks it's cool to just apply. Even if you get rejected. Like I got rejected once and I got an email from Paul Graham where he was like, oh, I think you could have done like this better. I remember just like showing that email to my friends like so proud. Like look, PG responded to me.

Right. This is just as good as getting in. Yeah. Basically. Oh, that's what were some of the ideas you're applying with? So the very first one was this company called Fmail, which stood for like get this Gmail for Facebook. Facebook released like their platform sometime when I was, I think, a junior. And at that point, like I'd never really built like a web app, but a buddy of mine was just like super encouraging. He was like, oh, this is so easy.

And just go learn PHP. And I'm like, PHP, like what is that? So I went online and I started learning it. And it's like, okay, I'm like, well, how do I store user information? Facebook was all PHP. Yeah. Yeah. It was all PHP. And I just kept asking like, oh, how do I do this? He's like, oh, just go learn like SQL. And after a semester, I learned all this different stuff. And I'd been able to build this app from scratch.

And I thought it was amazing. Like, oh, I didn't know anything about this stuff. And now I can like make my own web app. And I applied for YC and like, of course, got rejected. But a really cool thing happened where because there weren't that many Facebook apps and because I think people were just like looking for stuff to write about a bunch of like these small tech publications just like wrote about it. Like, oh, crazy MIT genius figures out a way to put a Gmail inside of Facebook.

Like we'd scanned it to like look like Facebook. And it barely even worked. It was like super crappy. But I was like, wow, it's like really easy to get like the press to write about you. And like you can do a really simple thing that takes you a semester, even if you're a total beginner. And if it's kind of creative and kind of unique and people haven't seen it before, like you'll get attention. So that was like a kind of a good experience, even though I got rejected.

And that was an era, too, where there were so few web products where when you did one and you made a new website, it could kind of stand out because there just wasn't a lot of noise. I remember you fled back so many memories there. When I was in college, it's funny, yours was Fmail. Mine was called Hacker Follow and it was Twitter for Hacker News. Like I wanted to be able to follow people on Hacker News and have a timeline view of when they updated.

So my buddy and I built Hacker Follow. And similarly, like I learned PHP and MySQL to be able to like store the stuff in a database. And I mean, that's what everybody did that. And that's even what Facebook was written in, David, as you mentioned. And the web was like, it felt like a small place. Yeah, it really did. And I think to some degree, like it always kind of feels like that in hindsight. You know, I think like 10 years from now, people will look back and be like, oh, like the quaint times of 2020 when you could do when you could do anything and it would get attention, you know.

And like to some degree, like that's true. Like if you spend like very few people have the time to sit down and just like think creatively about ideas. And like one of the easiest ways you want to come up with any creative idea is just to take like two or three things and combine them. Because like once you do these combinations, like you instantly start getting to ranges where like no one has ever done that before.

Like if you type like the dog into Google, you're going to get like 10 billion results. But if you talk like the dog left, you're going to get like a million results. And if you like type like the dog left the store with a bone, there's going to be like no results. It'll be like a sentence that no one has ever said before in the history of like the world. And the same thing is true with ideas.

So I think there's always kind of like this sort of framework you can use to come up with interesting ideas. And like we both found kind of the same one, you know, like, oh, let's take this one thing and put it inside this other. And like that was enough to stand out. And I think that's still true today. Yeah. Okay. So you mentioned Hacker News, which I assume is going to continue to play a big role in the story here.

What were you hanging out on Hacker News while you're at MIT and doing all these YC applications? So back in the day, like Paul Graham used to write on his blog all the time about startups and like all sorts of like different stories. And it was like he's very motivational, inspirational and positive. And then he had this website he created, which like, again, he just like seemed like it was very haphazard. He's like, what if I had like a little Reddit clone?

And of course, it's like now like millions and millions of visitors or whatever. But if you wanted to apply to YC, like you had to be on Hacker News. Yeah. Ben, you know the story, right? It exists because he was dissatisfied with our programming and was asking Alexis to make that better. Like Alexis and Steve, I think it was either to make it better or maybe to invent it at all because that subreddit didn't exist yet and got frustrated with their slowness and started Hacker News on his own.

Yeah, that's hilarious. So he's like, yeah, this is not good enough, even though he's an investor in Reddit and just like made his own competitor. I'm pretty sure that's against some sort of code of ethics. But you kind of had to have a Hacker News account to apply to be in YC. And like not only did you want to have a Hacker News account, but you wanted to have like a history of like smart, like intelligent, thoughtful comments because, you know, Paul Graham and the partners are going to look at what you had posted.

So if I look at like my YC account right now, I think it's like, yeah, created October 8th, 2008. So I was on YC like way back in the day, reading everything, digesting everything, and then trying to leave smart comments that like I would be probably embarrassed to go back and look at right now. It's so funny to think about now, like, God, how many companies, there were like 300 companies that go through YC-ish about every year.

And like, but it was this little corner and community of the internet. I mean, it still is a community, a very large community now in a certain sense. But I mean, I remember being a YC fan first and foremost and using the products. Like I was proud to be a Dropbox user and abandoned my flash drive because it was a YC company. I suppose that that is even actually a bigger effect today. But it felt at some point like a club.

I remember, I think it was like senior year of my high school. I felt like I was in some sort of club for even knowing what it was. Yeah, I kind of had that feeling. And then like, I eventually ended up doing YC. And I remember like distinctly that there were like maybe 35 companies in my batch or something. And all of us felt like, oh man, like YC is like, it's jumped the shark. It used to be so intimate and like so small back in the day.

You go to PG's house. And now like it's just this huge and personal thing. And you only get to see like Paul Graham like once or twice a week. Like what even is this? And of course now it's like 10 times bigger than it was back then. So catch us up there. So what idea did you end up going through YC with? Yeah. So in college, I ended up meeting up with like these two grad students who had this like cool idea for this new version of email.

And then we tried working on it. And like, it was pretty cool, actually. Like we got a lot of press. We got a lot of attention. But we didn't charge any money for it. And so after like a year of working on that, like we ran out of money. We'd won some business plan competition. And like it was like 25K. So I kind of just like lived frugally on that for a year in downtown Boston. Ran out of money.

And I decided like I was going to move to SF and somehow like get into YC. So I worked. I got like maybe enough money for like four months of rent. Moved out to SF. And I just started reading like Paul Graham's like RFS, his requests for startups that he would publish. And one of the ideas on there was like kind of related to what I'd already been doing. He had this whole thesis that like, you know, the email inbox is this like unexploited, you know, domain.

And you could have a Trojan horse where you get in there with like some sort of productivity app or something. And then once you get all of the email users off Gmail, like you convert them to your own thing. And so like that was his obsession. Like these like clever tricks you could use to like get a ton of people on your apps. And so I was like, okay, let's just do that. So I met another guy again on Hacker News who I kind of posted like, hey, I'm looking for a co-founder.

Okay. Yeah. I was good to say that. Like you met your co-founder on Hacker News. He was like one of my previous competitors from my earlier email thing. And his app like also wasn't doing that well. So we're like, why don't we join forces? We met in a coffee shop in San Francisco. And I had like maybe like a month of like money in my bank account. I don't know what I would have done. I would have just like had to somehow find money or like get a job immediately.

But we applied together. And like the process was super quick. We got in. PG asked us a few questions. We had like the YC partner interview and they're like, yeah, cool. And I was just like, okay, well, like when do we get the money? So I can pay my rent this month. Was this what? 2011? This was like we had winter 2011 for YC. So this was like in the fall of 2010, like November, December. We were applying.

So this was before the Yuri Milner SB Angel deal where you got. That happened during our batch. That was like the like we were the very first batch for that. I remember the previous YC batch was super jealous because they only got like, you know, like a 17K or whatever. And so that's what we got at first. It was like 17K divided by two. Me and my co-founder, like, you know, we had like enough for the two of us.

We ended up moving into this rent controlled apartment and SF and just eating like a lot of like oatmeal and crackers and stuff. And then I remember like one day during YC, they kind of called us down like on a like a Friday or like some off day. Like, hey, it's very important. Everybody come down. And we went down to the YC headquarters and they had like those telepresence robots kind of like walking around like sort of like a camera, like a screen on wheels.

And there's like Yuri Milner's face on it, like this Russian oligarch billionaire, like walking around talking to everybody. And like we've got an announcement. And I was like, yeah, we're going to give everybody like $140,000 of additional money, sort of no strings attached as an investment. So that was like one of the best days of my life. I was like, OK, well, I'm going to start eating like I'm going to upgrade to ramen now. And I don't have to worry about where my rent's going to come from.

So we structurally understand that. Was that a convertible note that they invested on with that? I couldn't tell you. I can't really remember. I think it probably was a convertible note. And this is before they had like, I mean, this is before they had the safe. I think the safe came came around like two or three years later. But it wasn't like literally free money. No, it wasn't literally free money. Like there were strings attached. But I think it was uncapped, though.

It was a really good deal. And none of us questioned it. Like we just signed the papers. So at this point, you're getting like probably feels like a huge amount of money in funding, right? Like you don't have any customers, right? Nobody's paying you anything. No, we had literally nothing. We had like a bunch of janky code that I was writing. And my co-founder was going around like, you know, like doing some marketing stuff and trying to generate like press and like hype for like a thing we hadn't built yet.

So the idea we were working on was called Task Force. The idea was you get all these tasks in your inbox. You know, like I've got Ben and David from Acquired like saying, hey, Coralyn, have you prepped for the podcast yet? Right. And no, you didn't really send me that email. But like if you had, I could have used Task Force to convert it into like a little to-do and it would add it to a to-do list in your inbox.

And so then when I worked on that to-do, if I added a due date or I checked it off, you would get an email that said like, hey, Coralyn is this far along in the to-do or Coralyn just completed it. So it was supposed to be like this viral thing that would like take over the inbox and everybody would have it. And eventually we did launch NYC. And like we got a decent number of users. By the end of YC, I think we had like 100,000 users.

But back in the day, like that was nothing. The social network had just come out a few months earlier. You know, a million dollars isn't cool. A billion dollars is cool. You know, that was kind of the mantra. And like no one cared that your app had 100,000 users. Like that was meaningless. I'm also dying over here because after Hacker Follow, my first app was a task list that I launched for iOS 3, which is like right around the same time period.

And if I remember right, like Gmail tasks was still this like really terrible UI that like could have had. I mean, you built the missing sort of connectivity for Gmail tasks that would eventually become. I think they turned it into its own thing, but it was like constrained within Gmail forever. Yeah, I think it's still there. Like if you know the right combination of keyboard shortcuts, like you can get a little task for you to pop up in Gmail.

But it's not the most inspired idea, like a to-do list, right? Every entrepreneur, every programmer has like a bunch of stuff they want to do when you think about solving your own problem. You're like, if only I could, you know, organize my tasks into like a little list of checkboxes. And so we did that and like it kind of sort of worked, you know, but it wasn't like the home run that you really... But we'll do it in Gmail.

Yeah, we'll do it in Gmail. There it was, like the combination. And like that's exactly what the press wrote about. Like, okay, you've seen a task list. You may have seen a task list in email, but if you've seen one in Gmail, people were like, no, I haven't. Maybe I should sign up. So we kind of combined those things. And we got to Demo Day NYC. Like the very end of YC. And we like presented. And investors just like, they weren't interested.

They're like, yeah, you know, you've had like okay growth. But like, where is this really going? And we've invested in email startups in the past. And they're all dead. Like, what's going to make yours different? And we didn't have a good answer to that. So we went into the summer after YC with like probably still like 120, 130K of this money in the bank. Trying to figure out like, you know, what are we going to do with this startup that's like not growing fast enough for us to raise money?

Again, if we have our lower rate. One of the talks, maybe like was it like a Tuesday dinner talk while you're on YC was Kevin Hale for Move Food? So Kevin Hale was this, I thought he was like the coolest guy on planet Earth. We had these, you know, YC dinners every week and people would come in and we had like the Heroku founders came in and they just sold for like $300 million. And they just bought us, like bought us all like the nicest steaks and, you know, they were dressed super suave.

And like it was so cool and flashy. Drive up in the Lambos. Yeah, yeah. And like I think PG brought in like the CEO of Yahoo at the time who was like the super extroverted guy who like said a lot and it sounded really good. But you can never quite like tell what he said afterwards. You know, and PG was like, this is an example of a stereotypical CEO. And then Kevin Hale came in from Wufu and he was like cool, calm and collected character.

And he was just like, yeah, like we're not raising any money. You know, like we packed our bags. We moved to Florida. Like we're making forms, but we're making forms sexy. And we do profit sharing with our team. You know, we go to the beach all the time. People work remote. Like I don't even know when they're working really. And we get like 10 calls a week from VCs who want to invest. And we're like, no, we're making millions of dollars.

We're cool. And no one else had said that. Like no one was making money. Like I didn't even know how you could make money because like Stripe wasn't even in beta at the time. It wasn't. So like in your cohort, nobody was like talking about that one. I mean, there was like there was like a few companies that like had some sort of revenue model. But like all the companies that were celebrated were the ones that had just like raised the most money.

You know, who raised from A16Z the earliest? You know, like there's one one founder on our batch who will not name who raised from A16Z like the very first week of YC. And they raised millions. And they are like putting up kind of Facebook growth numbers. And everybody like worshipped the ground like that these founders walked on. Like the whole it was obnoxious to the point where it was like I didn't want to see them. But like you're kind of jealous, too, because like I kind of want that level of success, you know.

But at the end of the day, like nobody was making money. Nobody wanted to make money. No one like it was all about growth. And so when I heard Kevin Hale talk about like how Wufu was just was just kind of crushing it. I remember running up to PG and like, hey, like, you know, we're not growing that much. Like what if we just did this? Like what if we charged money? And he was like, that's cool.

Like whatever it takes to stay alive. You know, he was very much like be the cockroach. You know, don't die. If you need to make money to survive until you pivot to a better idea, that's what you should do. But like that sort of asterisk was always there. Like what you then do is pivot to a better idea that, you know, can make you a billion dollar unicorn because like who wants to just make a few million dollars a year?

It's so funny. David always reminds me that incentives drive behavior. And if you think about sort of YC's incentive here, do you think back on it and say, well, gosh, they sort of for their portfolio construction, they needed us to be a billion dollar company. Or at that point, would YC have been happy with a bunch of Cortland's building profitable businesses? When you interview, they really want to know that you have a shot at becoming a billion dollar business because that's how the mechanics, it's like the physics of the situation work.

Like they need people to go for the gold. What ends up happening is a lot of YC companies died. Like even before our batch was over, it was kind of clear that like a few people had given up and they weren't really going to make it. And like especially in the summer after our batch was over, like just a lot of companies fell off the radar. I remember like talking to PG over the summer. We signed up for office hours and went in and he was just like happy we were like alive and still working.

He was like, oh, yeah, we don't even know what happens to a lot of these companies after a certain amount of time. So like we're happy that you're here. And I think after that, it's less they're less like adamant that, OK, you got to go for a billion. You got to go for a billion. You got to be a unicorn. They're like, do whatever it takes to survive and get to the next stage. I think in a lot of respects, like that's kind of like the hallmark of being a good entrepreneur.

Like how can you take like one, you know, small success and parlay that into something bigger? And eventually maybe you get another shot at going for the unicorn company. So I think in the beginning, they were very focused on us being big. There's all sorts of questions about how this gets big, which are easy to answer because it was like PG's idea that we were working on. But later on, I was like, how do you not how do you not die?

Yeah, it reminds me he's got that one essay. I think it might be in startups equals growth about the hill climbing algorithm. And you basically always try and find the next highest hill. And you would think that you could accidentally find a local maximum and not the global maximum that way. But in practice, whenever you're on a higher hill, that's a better way to get to the next hill. And you can sort of always use that way to find your way to the absolute maximum.

It's a little ethereal. But do you sort of agree with that? No, I completely agree. I think if you're creative enough and you think about it enough, you could figure out a way to your next hill. Like Andy Hackers today is, to my knowledge, like the biggest online community of startup founders. Andy Hackers in its first month was like a blog. You know, like there's a lot of blogs out there. You started off with like a very tiny hill.

And like I made the blog as big as like I think, you know, I wanted to. And like maybe it could have been bigger, but it was pretty big. But like there's always some way where you can say, OK, now I have this advantage that I didn't have last week or last month or last year. Like what ways can I use this advantage to like, you know, parachute over to that like slightly bigger hill? And maybe you like lose a little altitude on your way there.

But then you're on this bigger hill and it's much easier. The analogy I like to use, maybe not hills, it's like a staircase, right? Like a lot of people want to like jump to the top of a staircase, right? And it's very hard to jump to the top of a staircase. Like very few people are capable of that feat. But it's pretty easy to walk up a staircase one step at a time. And so I think a lot of being a founder is just figuring out how you can go one step at a time.

Even if you have some grand ambition, how you can start like super small and then kind of work your way there. I love that. And without jumping too far ahead to IndieHackers, it just reminds me, the threads of your ability to be a community builder and a participant in online communities sort of starts with meeting your co-founders on Hacker News and being an obsessed participant with that. And like you said, today you run, how do you describe it?

The largest online community of... Startup founders. Startup founders. Startup founders. That's cool. I mean, they're IndieHackers. Like they don't mostly have billion dollar ambitions. You know, they're the underdogs. But a lot of them, I think once they get started, realize like, oh, wow, like, you know, like I'm making some side income. And then a few months later, like, oh, wow, like I can quit my job. And then at some point, like you're making a lot of money and you're thinking, okay, well, like what do I want to do?

Do I want to retire to a beach somewhere? Or maybe like what I want to do is build something even bigger. So a lot of IndieHackers I talk to are like are no longer even IndieHackers. They've raised money. They're building bigger companies. And that's like where their life path took them. Well, that's what I think is so cool about this. Like unless you would disagree, you're the authority. But I don't think being an IndieHacker means like you don't want to raise money or you don't want to build something big.

Right. It's like you want to build something that people want and the customers will pay you for and go from there. And sometimes those become Notion. Right. Or like sometimes they become IndieHackers. And sometimes they become just a business that makes you a couple hundred thousand a year. Yeah, exactly. Like I don't like to juxtapose IndieHackers like as a counter argument to like raising money so much as it is a counter argument to like having a boss and working like a desk job and wondering what if for the rest of your life.

You know, being an IndieHacker is really about the idea that like you can achieve your own sort of freedom, whatever that means to you. Maybe that's financial freedom. Maybe that's creative freedom. So you can work on whatever you want. Maybe that's like time freedom. So you can work whatever hours and schedule you want. And so being an IndieHacker is really just like this confidence in yourself. Like, hey, you can create something that that'll make your life better, really, and make other people's lives better in the process and give you that freedom.

And maybe that looks like raising a ton of money in the future. Not to mention it is the ultimate option value preserving activity where, you know, if you start by saying growth at all costs, don't make any money, we're going to raise venture dollars. You're on a path. You're on a very specific path. If you say, I'm going to build something profitable that funds itself, you got all the option value in the world to continue to take it whatever sort of trajectory you want to.

Yeah, exactly. And the kinds of companies that I've seen people build, like I almost feel like we need a new word. Because you think about business, it has all these connotations. Like you imagine like a bunch of men in like suits and like a boardroom or something, you know, reading like graphs. And then like the word startup is like not quite right. It's closer. Because you think about tech and technology and it's like internet enabled. They're wearing t-shirts instead of seats.

Yeah, yeah. But they're doing the same thing. Yeah, exactly. Like there needs to be like some like, I don't know what it would be, like some third word where I'm just like looking at people. Like I interviewed this founder, Sam Eaton, on the podcast earlier this year. And like his sister at some point was like, I want to sell cookies. And he's like this software engineer who's worked in like growth roles at Airbnb. And he just got a job offer at Google.

And he's like, no, we're not just going to sell cookies. We're going to have like a cookie company. And we're going to like be tech enabled. And we're going to have an app and like all sorts, like our own fleet of delivery drivers. And like he's just in heaven sitting around like coding his own apps. Like they don't use Uber Eats or DoorDash. Like they have their own delivery drivers, their own sort of internal mechanism. His sister's like the head of cookie R&D.

And they're making like 100 grand a month selling cookies to their local town. And he's doing all this cool tech stuff. And they have like 50% margins too. So like they're living a really good life. And it's like, it's not just like your traditional idea of a business. He's like trying to like make his community better, trying to make his life better. And he's not stressing over like how fast can we grow and how much bigger can we make this?

He's thinking about, you know, like what do I like to spend my time doing? While at the same time, he's like kind of getting rich and making everybody feel great. I think this is like such a big movement alongside, you know, the traditional startup, race venture capital, like be something big right off the bat. Because like the economic, you know, generation activity generated by this class of entrepreneurs is probably in aggregate going to be equal, if not larger than like the Rockefellers of the world.

Did you guys watch that series Chernobyl? I was on HBO last year. Oh, so good. Great series. I heard about it. It was freaky. They like timed it. So like right after Game of Thrones went off the air, they're like, boom, here's another series. Don't unsubscribe from HBO. But they kind of boiled down the entire story, like the work of like this one scientist. And it was like an amazing story. It was great. But like obviously in real life, it was probably dozens or hundreds of scientists and engineers working together to try to figure out how to contain this nuclear disaster.

And like the reason why they did that is because it's just easier to tell a story about like one person. And it's the same in business. Like it's easier to tell the story of like one company. We're all fascinated by like how big Apple is and the impact that Apple has. Or like, you know, McDonald's is crazy. Like they have 20,000 restaurants in the United States because that's like the easy story to like to understand and to tell.

But I think like the much more impactful story is like there are 600,000 individuals who have restaurants in the United States. And like that's way more impactful than like McDonald's having 20,000 restaurants. But it's a harder story to wrangle. It's like a harder story to tell and to connect the dots. And I think the way I look at what I'm doing with indie hackers is like I'm trying to like connect the dots of all these really tiny tech businesses that are never going to make the news.

You know, they're not, you know, Amazon. They don't have a $2 trillion market cap. But like what happens when like a million people are building businesses and make millions of dollars online? You know, what does that look like? When this comes out, we will likely have just done the DoorDash and the Airbnb IPO episodes. There is a narrow set of practitioners, whether you're a founder or an employee, who can learn from the tactics and the playbooks accomplished with DoorDash and Airbnb.

But based on all the media coverage that those are the stories that get told because that's the simplest and most interesting narrative. But if you're looking to actually learn, like let's say indie hackers continues to grow and expand and you figure out more ways to parallelize it. And at some point there's, you know, a hundred thousand stories of businesses and the playbooks that they ran on your website. Like someone can find an incredibly narrowly applicable business that's just three years ahead of them and run their playbook on their own business in a way that is far more useful than the one story that everyone focuses attention on.

Yeah, exactly. That's kind of the goal of like a lot of the things that I'm building on indie hackers. So like, how do you see like these companies like very early days? And then how do you like filter down to like a very specific niche? So you find the company that most matches their profile of what you're trying to build. And so we have like this directory that I kind of haphazardly built like two and a half years ago.

And I was like, oh, we should have a directory of products. Then I haven't touched the code in like two and a half years. But like when I built it, it was like, okay, we had like 50 people on it. And I checked the other day and it was like 12,000 products on there. And they all have like a little timeline where they're like saying, okay, here's where I launch and here's what I thought about my launch.

And I thought I was being ridiculous saying a hundred thousand, but it shouldn't be long. No, it shouldn't be long. You know, and I think it's just a resource that needs to exist. Like you need to be able to go out and see how other people are doing it because that gives you, I think, the confidence to go do it yourself. When you see that someone who's like not that different from you, like kind of put their playbook online.

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Yeah, I'll give you the whirlwind story. So at some point during the summer after YC, Stripe entered the beta phase. So this is like 2011 and Stripe's like, hey, you want to make money with your product? Go for it. Were they in your batch or they were before you, right? They were before I was, like maybe by a year or two. They took a while before they got their product to the point where it was ready, understandably, because there's like a lot of regulation dealing with banks and stuff.

But they kind of launched into beta and we got like a good first look because we were on the YC mailing list. So like we threw up kind of a Stripe subscription and like maybe like a day or two, just like over a weekend. And the next weekend, I think we made like $3,000 in payments, charging people like five bucks a month for like this crappy to-do list Chrome extension. Like I thought we were going to make like $100 or something.

And I was like, holy shit, like we can like kind of pay our rent, you know, like we can pay for stuff with this. And so of course we went to the YC partners like, hey, look at this. This is cool. Like we're making a few thousand dollars. And they're like, yeah, but what if you were making like way more and you had a different idea that wasn't a tiny Chrome extension, which in some ways is good and bad.

In hindsight, if we had stuck with what we were doing, we could have probably grown it to a much more substantial size and iterated. Instead, what we did was we like did what you should never do. We just completely started over from scratch with an idea that we thought was like bigger and better. And we sort of violated that principle of like taking it one step at a time. And so probably over like the next six or seven years, I started five or six different companies.

Each one, you know, got to a point where it made like a few thousand dollars in revenue, but it was never really a big deal. It was never like the success that I really wanted. And I think this is kind of an important thing that I realized. Like the first couple of years, I was just like peddled in the metal on my computer every day coding as much as I possibly could. Like this is going to be it, you know, like I'm going to succeed.

Like this is going to be it. Like it has to work. And like it never did. And not only did I not succeed, but I also just like wasted a bunch of time, like not living a very fun and productive life. Like I don't even remember like one or two of those years of my life because I was like literally just doing the same thing every single day. And now my model that I have for it, kind of framework in the way I think of it and the way I wish I had thought of it then was that everybody's kind of got like a certain number of companies that you need to start before you succeed.

For some people who are exceptionally talented or lucky or both, like that's just one. They're going to succeed right out of the gate. Some people, maybe it's like 35. For me, it was like seven. And really, all you need to do is just to make sure that you like you don't quit before you get to that number. Like that's really the entire name of the game. Like just don't quit before you get to the number where you succeed.

And so you should just structure your life to make it so it's easy for you not to quit and to make it so that like the journey itself is like actually pretty fun. And you're learning a lot along the way because like you're not just building a startup in a vacuum. Like you're meeting people and you're picking up new skills and you're learning new things. And like the startup is kind of like the journey is as important as like the destination at the end of the day.

And so nowadays and like eventually I kind of figured it out like, oh, I'm like learning so much stuff. Like I should make sure that like I'm really enjoying my life while I'm building stuff. So the last few years there before I ended up starting IndieHackers are actually really pleasant. And I feel like I kind of leveled up as a person while I was building my startups instead of just sort of like, you know, worrying every step of the way.

Like, am I there yet? You know, is it going to work? Is this going to be the one? Hmm. That's such a great lesson. And just like a couple of points of clarification. Were these all inside the same like entity or was it different co-founders or how did that sort of technically play out? Yeah. Like the first one or two were kind of inside the same entity. And then my co-friend and I split up and we kind of just declared our YC startup dead.

Like this is, you know, this is the end. I think I quit and he kind of like bought me out for my shares. And then I just kind of did my own thing. And like by that point, I realized, okay, what I need to do is figure out how to like make this last. Like I want to spend the rest of my life just working for myself on whatever I like. Like I don't want to go get a job.

Part of it was like I just didn't like the idea of having a boss. Like me working at Stripe today is the first full-time job that I've ever had. Like I just don't like to be told what to do, I guess. And part of it was like this, like, I don't know, this pride. Of like, I don't want to have to interview somewhere. Like I don't want somebody to be able to reject me. Like I want to be unrejectable.

Like I don't want to ever put myself in a position where somebody could say no. And so like, okay, I just want to keep doing this myself. So I would just like survive off of kind of my income from some of these apps because I would keep them running and they would make like a few hundred dollars a month or a few thousand dollars a month. And then when I got low on income, I would just go get a contract job and then like work on the side, et cetera, et cetera.

And just kind of like make it so I never had to quit, you know? And I think there's a lot said about startup failure. Like, okay, maybe your ideas fail because like the market was too small or because, you know, your product took too long to develop or you ran out of money. But my take on it is kind of that none of those things actually kill your company. You know, like those are just obstacles, right?

Like so your market wasn't big enough and then what? Right? Like you quit. Like you didn't have to quit, right? You could have like, that's kind of like if you imagine like a startup journey, like being like you walking from like you being an early pioneer walking from the East coast to California, right? Like those are just like obstacles. There's like rivers and mountains and like you can kind of like step over those or go around them or you can just be like, fuck it.

I'm just going to like stop here and just live in Kansas, you know? And like you don't want to stop and just live in Kansas. Like you want to keep going and find a way to keep going. And so for me, that was just living super frugally and figuring out a way to like start the next thing, which meant taking on contract work and building up my savings whenever I needed to. Yeah. Default alive or at one point I ran a startup weekend in Seattle and Bo Liu, who actually I think went on to YC with this company, Future Advisor and Sequoia funded it.

He gave this great talk called You're Alive As Long As You're Not Dead. And he was like, yeah, lots of things, bad things can happen at your company. But as long as you don't shut it down, you have not failed. Like your company is still in the act of succeeding. You're not successful yet, but you are in the act of succeeding until you call it quits. Exactly. That's always stuck with me. And even if you do quit a particular company, like I've quit lots of different companies, but like as long as you don't quit your overall journey, like you're still on that path, you know, you're still headed to California and you like you're going to eventually get there.

Who knows how many startups it's going to take, but you'll get there as long as you're sort of learning and you persist. So I think the most important thing you can do is figure out how to keep going. All right. So the genesis of Indie Hackers. The genesis. How did that happen? So I just rolled off a contract job and I had about a year of runway in the bank. So I was like, OK, here we go.

Like take four. I'm going to I'm going to figure out something to work on that's going to work this time. And, you know, worst case scenario, it's going to all fail and I'm going to go back to working contract jobs. And so I started working on this one app that I called Knox. And it was kind of like this meant clone for your phone that would like buzz you with your finances. And like maybe like two or three months into it, I was like, this is an endless slog of coding.

This is going to take me forever. I don't see like the end of the rainbow. Like I need to just call it quits right now. Like in the time where I was working on that, I saw a couple stories in Hacker News of people who would come up with new ideas and were already making like five or ten grand a month. And like I hadn't even launched my thing yet. So I was like, OK, this is like a dud.

I should scrap this and go back to sort of the drawing board and figure out, you know, what can I like, what are all the different lessons that I've learned after years of doing this? Like, let me make sure like I'm systematic in how I approach this. So I'm not just kind of making the same mistakes again, because I had repeatedly made this mistake that a lot of software engineers make where we just, you know, spend way too much time coding.

And like, I think the biggest lesson at the top of the list was like only work on things that you can build in like a few weeks. You know, like I went from idea to basically launch with any hackers in exactly three weeks. And it didn't require very much code at all. It didn't require like a lot of marketing or anything. It was just like super, super easy. I think this is one of the levers that a lot of founders like don't realize that they can pull.

Like everybody's trying to figure out like, how do I get enough money to work on my idea? Like, do I need to fundraise? Do I need to, you know, borrow money and go into credit card debt? And like the other lever people pull is like, oh, how do I get more time? You know, maybe I'm going to work nights and weekends and all this stuff. And like, I want to work a three day work week instead of five day work.

But I think like the third lever that's probably the best is like, how do you just start smaller? Like, how do you figure out like what's an easy, even easier thing to do? And for me, my idea was kind of like, okay, I want to build kind of an indie hacker business so I can sort of, you know, pay my rent, pay my bills, and then figure out what I want to do next. A ton of other people clearly want to do this.

Like I see them on Hacker News every day asking all these questions to people who've done it and sharing their stories. Maybe what I can do in a very meta sort of way is build a better version of these Hacker News discussions. People are always talking about this, but their stories kind of suck. You know, they're like leaving out important details. And like everybody in the comments is asking them like, well, how'd you come up with your idea or how much money are you making?

And like, that's not necessarily in their stories. If I can compile all of the stories that I found and tell them in like a really compelling way, I make sure I always ask for revenue numbers. I always ask for how they come up with their idea. I always ask about technical details. And I can put that in one place. Then I'm making life easier for like both me and a bunch of people who are like me who are trying to figure out how to be indie hackers themselves.

So that was kind of my idea. Kind of phase one. Like I didn't have a revenue model. I didn't know where I was going to go from there. But I was like, that's a really easy place to start. All I have to do is email some people and, you know, get their information, put it on a blog and launch it. And like, I'm 100% sure people in Hacker News are going to eat it up because they've already been eating up stories like this before.

And is the idea that this is going to become a business for you at this point? Or is the idea really like, this is a project. I have it envisioned in my head. I know the scope. I know how to build it. I think people are going to love it. But it's a project. 100% is going to be a business. I don't know how I'm going to make money yet. But it's 100% like at some point, like I'm going to start in this really small pool.

You know, I'm going to build, I'm going to take the first step on the staircase and do something that works. And then from there, I'll have some advantage that I don't have today. Like maybe I'll have an audience. Maybe I'll have a lot of traffic. Maybe I'll have a big mailing list. And then from there, it should be easier for me to figure out how to make an actual business. The revenue aspect, maybe revenue and profit aspect of the stories you were telling.

Was that super key? Like, because I can imagine like, you know, and you're trying to find like, oh, yeah, you're talking all this game about like how great it is, all the stuff you did. But like, is it actually working? Like, you know, give me like, like that feels like almost like the, like the Zestimate before Zillow, right? Like, you know, it's like, hey, this house looks good. But like, what's it worth? Like, you know, how important was that?

Extremely important. Like if I could write a startup book, I would call it Problems First, where like the first thing you want to do is you want to figure out like, what are the problems that your potential customers have? So you don't build like some random product that like doesn't solve their pain points. And when I was like reading all these comments on Hacker News, like I was trying to find a business idea. And I didn't want to read comments from people who like didn't have proof that their business idea worked.

You know, somebody said like, oh, I've got this great company. I'm working on it. It's really great. You know, it does this and this and this. And like, they don't share the revenue numbers. Like for all I know, they're making like $5 a month, you know, and it's not that great. And I could tell everybody else in the comments, like had kind of the same problem. They're like, hey, we only want to upvote the stories that share their revenue numbers.

We only want to upvote the stories that have like some sort of proof or some sort of like inspirational thing that we can like grasp onto to know this person is legit. Anybody can give you advice and tell you what to do. But if there's no like outcome that's a result of that advice, you don't know if it's good. And so train your model on garbage data. Exactly. And so like that's a thing where like there were a lot of other interview sites on the web that talked to entrepreneurs.

There are pretty much none at the time that realized how important it was that like you needed to be transparent, like you needed to include revenue numbers. And so when I went out and I started emailing people and saying like, hey, you know, my name is Coraline. I'm starting this website. It's going to be called Andy Hackers. Like, will you tell me your company story? And oh, by the way, like I need like all your revenue numbers.

Half of them were just like, fuck off. Like, why? Like you're nobody. Like, why would I give you my revenue numbers? And then like half of them didn't respond. And like a tiny percentage were like, hey, you know what? I think this is super cool. I'm happy to pay it forward. Somebody, you know, did the same for me in the past. And so by the time I launched, I think I had I'd gotten like 10 people to agree to share their entire story and their revenue numbers.

When you launched, you built the site, right? So like you didn't go to Squarespace and go to Webflow. You did. What was the thinking behind that? Yeah. So I had a couple sort of reasons for that. Part of it was I had a bunch of other ideas that I had come up with and my brainstorming and Andy Hackers kind of scored the highest on my rubric because it was so quick to build. But I felt really bad because like here I am the software developer, like from building all these other startups.

Like I learned so much stuff from building startups over the years and like failing time and time again. Like I learned how to design and learn how to do front end development and back end and like server admin stuff. And here I was like going to start a blog. So I was like, wow, it's such a waste. Like I want like to throw myself some kind of bone to make this fun because starting a company should be fun.

Like you should enjoy the journey, not just the destination. And so I said, okay, well, I'll do a blog, but I'll allow myself to just build like my custom blog from scratch, even though that's going to add like another week and a half to my launch time or whatever. Like I'll allow myself just that little bit of fun. And then part of it was kind of a branding and strategy play. So you weren't yet thinking like Stripe Revenue Connect, like, you know, building a community and like...

That was like kind of in the back of my mind, the community stuff. Definitely not like the product directory and Stripe Revenue stats or like a lot of the stuff that exists today. But like I did have kind of a strategic sort of session with myself. So I spent like one day just thinking strategy. Like because in the beginning of your company, there's a bunch of decisions that you make that are much harder to undo later on.

Like you'll tell yourself like, oh, I'll use a crappy design now and redesign it later. But like really, that's a lot of work and you have a lot of more urgent things. And you say, oh, I'll have a crappy name now and have a better name later. But like really, like it's hard to change your name later on. So I had been bitten by like all these issues. And so I said, okay, I'm gonna take one day and make all of these like semi-permanent decisions.

Like what do I want the color scheme to be? How do I want the site to work? What do I want it to be called? And kind of the three decisions that I came to were, number one, I want the site to be named after kind of a new class of people. Because I was like, well, there's no name for like these people and these discussions. It's like really hard for them to find each other even.

Because like there's like, what do you even search for? Like story of person who bootstrapped startup and makes 5,000. I'm like, there's nothing to search for. It's so hard to find. So I was like, I'm gonna call it Indie Hackers. I had a bunch of like worse names. But Indie Hackers was the best one I came up with. I decided I wanted to make the site like blue. So it's like this very dark blue color that's like probably not very accessible and kind of hard to read.

But every other site in existence was just like white with black text. Everybody was writing on, you know, medium. It all looked the same. And so I wanted mine to stand out. So if you ever read two Indie Hacker stories, you would instantly remember that you'd been to this website before. And then I wanted to do it custom. Because I just didn't want to build on somebody else's platform. I didn't like the platform risk. I've been kind of burned by that before building on Gmail.

And, you know, they would change their API all the time and like kind of break our apps. And so I didn't want to deal with like, you know, putting up a blog on medium and having it look like every other medium blog. And then medium changes their business model or something. And now I'm screwed. So those are kind of like the three decisions I made back then. And all of them, I think, turned out to be pretty good in the long run.

And the etymology of the name, it's interesting thinking about when you started this, the notion of an Indie developer was already a thing. I mean, I remember considering myself an Indie developer in 2008 when I started working on my first iPhone app. And I think Craig Hockenberry and a bunch of the like Icon Factory people, they were saying, oh, I'm an Indie developer, Indie, you know, iPhone or Apple developer. And obviously, Hacker News was sort of like a thing.

But those communities were basically non-overlapping. Like hackers were what people who were technical and wanted to start high growth technology startups refer to themselves as. But Indies were what the like lifestyle developer community primarily centered around Apple platforms kind of called themselves. Yeah. And I wasn't thinking about like, honestly, any of that Indie stuff. Like it wasn't even I wasn't even aware that they were like Indie developers. I was just like, OK, well, like I want like the idea of like an independent programmer because again, it wasn't so much a rebellion against raising money.

It was a rebellion against, you know, going to work for the man and like, you know, making Google $10 million a year from your code. But you're only getting like 200K of that, you know, like why don't you start your own thing and be like kind of your own Indie developer? And Hacker News was so called because like hackers are just another word for programmers. So the idea is like, OK, you're a programmer, but you're independent.

There's no cap on your salary. You know, there's there's really no limits like you can do whatever you want. Yep. And before we move on from this point, talk to me about platform risk, because in my mind, you know, we think about this for acquired, too. We're always trying to get the most direct relationship possible with our listeners, with our LPs, with our, you know, with everybody. And there's always some platform risk. Like we've collected email addresses from one out of, I don't know, six or seven listeners, you know, from all the various reasons that people join our Slack or they sign up for the emails, which, you know, now have the playbook.

So there's even a further incentive to sign up for the emails. But at the end of the day, even if you have someone's email, you know, you could go to their promotions tab like you never it's not like you can call that person. There's always some amount of indirection between you and and your end customer. So how do you think about how far you should go on eliminating platform risk? Yeah, I think everything in business is basically a tradeoff.

And what you really want to do is just be like aware of the tradeoffs that you're making. Like there are no hard and fast rules like never build on a platform, right? Like if you build on a platform, maybe you can give you additional distribution, but then you get the risk that they might shut you down or change things or you might like lose out on the branding or the ability to differentiate yourself, etc. Like maybe you can charge a high amount of revenue per user, but that means you're going to get, you know, maybe fewer users in the door, fewer customers.

But then also you can spend more to require your customers. It's all tradeoffs. And so for my particular situation, when I looked at that tradeoff, like really the only contender was like, okay, I can like maybe try to build a big Twitter account where I share these stories. I can repeatedly, you know, post on like Reddit or Hacker News or like I could have a kind of a Medium blog. Like those are the big platforms that I considered.

And every one of them I thought would give me either very limited distribution, like how much did Medium really help with distribution? It was kind of hit and miss. And they would also just like completely destroy my ability to have any sort of branding. And I knew that kind of step two in this playbook might be to build a mailing list or a community. Like I wasn't sure, but I knew that like if I was going to name it in the hackers, like go for something where the brand actually mattered, which I think is important if you're going to have something where it's kind of like free and I was just getting like lots of users in the door, but I didn't have a business model that I wanted to own my brand.

And so it wasn't worth it for me to use any of these platforms, even though they would help with distribution, if I could instead just like do my own. And I also had like kind of my own distribution strategy. I already knew that people were going to be eating this kind of stuff up on Hacker News because they already were. And I already knew that Hacker News had like a lot of traffic. So it's like, okay, I don't need Medium, you know, I can do it on my own.

So like I get like no real benefit from Medium and I get all this additional risk. Like the trade-off just wasn't worth it. It's kind of funny. I mean, in some ways you maybe ran the Airbnb playbook of Exfiltrate Craigslist. Yeah. You did for this segment of Hacker News. My buddy Greg Eisenberg has this whole idea of like, you know, unbundling Craigslist, unbundling Reddit, unbundling Hacker News. It's a huge community. There's all sorts of sub like discussions happening in there that happen regularly.

Totally. There's a, it's a pretty big tent. Exactly. So you build the site, watch the blog on your site. As I understand it, pretty quickly you figured out that email was a pretty big unlock, kind of on both like for the interviews you were doing, call it the supply side of these stories and for readers for the demand side. You can almost imagine the web is like a collection of like feeds or like destinations. And some of them are places where people go like habitually.

Like I habitually check my email. I habitually check the notifications on my phone. I habitually check Twitter. I'm just like addicted. Like I'll sit down and just like press T on my keyboard and like black out for a second. Like I'm on Twitter. And then there's other places where like people just don't have a habit. Like I made Indie Hackers. No one on earth had a habit of regularly visiting Indie Hackers. And they weren't going to have that habit anytime soon.

So I was publishing like once or twice a week. You know, like Twitter's got new content every single minute. So for me, it was like, okay, well, how do I hook into like one of these feeds that everybody already habitually looks at? And it was a combination of both Twitter and email. So I made like the Twitter Indie Hackers account. I tried to tweet every story that I had so that you would sort of incidentally run into them when you check your Twitter and be like, oh yeah, I remember Indie Hackers.

Let me go back there. And then email was a huge one because like I actually own the email addresses when people sign up. Like I can take that with me anywhere. Like you can't shut down my email list. And so from day one, like I had kind of a email collection box at the very top and like at the bottom of every interview, just trying to get people's emails. And I think in the first week we got like a thousand or 1500 emails and it was like kind of continued on that pace for a while, like a thousand emails a week from people from Hacker News and all over the web who just like loved these success stories.

Like they would come and read them and they would be like so inspired to hear that like, you know, so-and-so was making a 10 grand a month from like their travel startup. I'm like, I'm a developer. I could do that too. And so they would immediately get on an email because like they want more of these like stories, you know, they want more, um, glances at like what's possible so that like, and when the day comes that they're ready to start their startup, like they haven't forgotten where to go to see those examples.

You gotta have some reason that like you're going to show up for people. Like one of the things, you know, I kind of joke about it. I don't know. There's no way to scientifically know, but like, and we didn't plan it this way, but the fact that our podcast name is ACQ, like in almost everybody's podcast feed, we are at the very top because for whatever reason, podcast feeds are organized alphabetically. And like how much benefit have we gotten from that?

Like, I don't know, but probably a lot. I'm pretty sure we've gotten a lot. We got at the top of an accidental feed. Yeah. Yeah. I think it's a hard one lesson for a lot of people who are starting startups. Like if you're an indie hacker, you don't have like a bunch of investors and mentors. like you probably just kind of by default believe like you know if they build it if i build it they will come you know i'll just build some cool stuff and get a bunch of people like in the door but it turns out that like building stuff is kind of easy even like even if you're not a developer today like you can stitch stuff like i talked to a guy yesterday who built like a whole slack bot without

using code at all it doesn't even know how to code and uh the hard part is like getting people to actually care about what you're building and actually find it so that means like you have to actually solve what it's like and you run into it yes and run into it and run and it's not just run into it once it's like run into it like repeatedly repeatedly and like that's very hard to do but if you think about it like really carefully before you start then often like you can come up with something like what i found is helpful is like you just go to one of the places where people find things and you just look at what they're sharing you know that that's kind of accidentally what i did

with indie hackers like i was already in hacker news and it took like days of me reading these threads before it clicked like wow everybody is here sharing this thing like why don't i just like make my thing better than what they're sharing here and then share it in the exact same place okay so we've talked about like the this insight that you had that enabled growth so you know we sound like circa 2011 yc you know like tell me about your growth rates like now let's now let's shift to the indie hacker conversation how did you start making money yeah so actually what happened is like my very first sort of hit of revenue was completely unexpected it was like maybe two weeks after i launched

and some company was like hey can we sponsor you and i was like sure uh how much do you want to pay and they're like how much traffic do you have and i told them like sure we'll give you like 750 bucks a month and that to me was insane because everything that i had ever built was like some like rinky dink consumer app where i was like begging people to pay me like five bucks a month yeah pennies and people were like well no it doesn't have this feature i can't possibly afford five dollars a month and then they'll go like buy like a bad coffee and like dump it out you know so like this company like offering

me hundreds of dollars like it was like a wake-up call like oh i can like make money from sponsors but i was also like super focused on growth because i was thinking okay well i've got like maybe six months of runway and i've got six months of savings in my bank account i've got time like why don't i just grow the site even bigger because there's only one of me like i don't have that much time to try to sell ads and build a site and do all these interviews i'm doing every single week i'm just going to grow it not worry about money and i'll worry about it later so i did that for like three months i just kept trying to grow the site i didn't figure out how to grow the site at all

i did like never found something that was bigger and better than getting on the front page of hacker news go figure and so by december i launched in august by december i was like okay screw this i'm going to start trying to make money and so i started like basically emailing my list which at that point had probably been going to like 10 or 15 000 people and saying hey like you know here's the email with the new like this week's interviews but also by the way here's an empty ad slot like your company could be here and i was very lucky that literally it's the billboard that you see with the like your ad could be yeah it was exactly that but an email form and i put that on the website too

and like it turns out when you have a company that targets people who are starting companies you have a lot of potential advertisers on your mailing list who all want to basically advertise with you and it also turned out which i didn't realize at the time that nd hackers were like some of the worst possible customers to buy ads because like these are very fledgling startups like these are people who had decided to start something because they read about it on nd hackers like two months ago and if they were going to spend like 500 000 on an ad like that ad it better work like that's not that's like their whole yearly ad budget and so i it's almost like you would want a company that is

selling tools to people almost like that so i went through like a lot of these awkward conversations where i'd run ads for people like i just wanted to do right by them but like the ads didn't always get enough clicks and sometimes like i would refund people and it was just like very stressful i didn't like doing it and so i created kind of like a dream list of companies like okay which companies actually have a lot of money that would be good sponsors like i've no i've no experience doing sales but like i'm gonna have to figure out how to do this and i had the very bottom of my list like my number one dream company who should be sponsoring indie hackers was stripe i'm like okay i'll eventually

get to them but like i want to like figures but i'm like i want my shit to be good some warm-ups in first yeah i need some warm-ups you know and so i don't warm up on broadway exactly you don't want to like embarrass yourself in front of everybody so i got some warm-ups i sent a lot of cold emails i found like the heads of marketing on linkedin my buddy jeff who ran a podcast i was on gave me kind of his list of leads for who was advertising on his podcast and like to my surprise it was like way more pleasant selling to big companies than it was selling to small ones like i would get someone whose entire job it was to spend a marketing budget and they would just want to talk about their kids

talk about their vacations and be like oh yeah you're cool like here's a check for five grand and i'd be like holy shit this is a thousand times easier than selling to people who are broke yeah not to mention like one of my key startup lessons learned over the years has been sell to things that have budgets like don't try and create budget fit into a budget and sure there's emerging markets where like the budget line item is not going to exist for your thing but you're so right that if if there's somebody whose job it is and they have a budget to spend like your life is just going to be so much easier and i think that applies to even coming up with startup ideas and trying to figure out

a business model like it's kind of counterintuitive like people repeat this mantra like you know solve an unsolved problem and it's almost like you want to do the opposite like you want to look at problems that people are already paying a lot of money to have solved and kind of like insert yourself there like my friend started a company called key values she's like been one of my best friends for years her name is lynn and like her company helps startups hire engineers and you know what like startups are hiring engineers just fine like well before her company came along but like we kind of picked that idea because we looked at like where are companies spending money you know like where do they spend a lot of their money and it turned out like hiring engineers

hiring recruiters was like a huge huge cost center for companies and like they were just willing to spend a lot of money on it and within like a year of starting her company she grew her revenue to like 100 grand a quarter she was living like a great life it just actually made it look easy her first time out of the gate in part because like she picked a problem where like people had budgets right and i think the insight here is like if you really want to overly simplify the sales process there's educate and then win like educate people that their need is real and then once they're convinced that they want to solve this problem then go win and be the way that you solve that problem for them and if you're selling

into people with budgets you don't really need to educate because they're totally bought in on solving that problem already yeah and education is hard and it's risky because you might educate somebody and then lose because someone else comes along and wins yeah or more frequently you educate somebody and they're like yeah i don't know i've got these other things that like i need to solve all right so broadway comes then you get a particular email yeah so i don't know i'm selling ads for like a few months i'm just happy to be honest because i got to the point i think in february 2016 where like any hackers is going to pay all of my bills and i was like wow like in less than a year i've gone

from like you know nothing to finally like one of the ideas i've done works you know so i'm like so no none of the other companies you'd worked on you'd gotten to this point where it's like no revenue is covering my personal no and it was better in like literally every single way like i eventually like i had added a community and so people were sort of talking to each other so i began to see kind of a path where like oh i can do less work like maybe people can interview each other and like i don't have to do anything people really liked it you know it was like a very like i wasn't making to-do list software where like all i got were like angry customer emails because i don't have

the right feature like every email i got was something positive people talking about how inspired they were by an interview that they heard like it was just like a hundred percent good for my life in every single way so i was just like blown away and super happy and just high on life and then to make things even better i get this email out of the blue and so like i hadn't gotten to stripe yet on my my sort of like list of sponsors to reach out to it's maybe halfway down you weren't in the same batch like you didn't know that no like i think during the stripe beta i'd like maybe like gone in there like a little stripe chat room and like you know pointed out some bugs and asked

some questions but like i never really talked to the founders outside of that uh and the email like i just stepped off a plane actually i was going to a buddy's bachelor party in mexico and so i stepped off the plane i was checking my emails and like the very top of the inbox was like acquire indie hackers question mark from like patrick at stripe and i was just like holy shit there's like there's no way this email's real like this is completely you're getting trolled i'm definitely getting trolled but i read it and it was real and he was just kind of like hey corlan like really like admiring what you're doing at indie hackers you know is there any way you'd be open to

stripe you know potentially acquiring it and so the first thing i did was like i forwarded it to my mom sent to my brother sent to my friends it's the paul graham email all over again yeah yeah it was like the coolest thing ever and we ended up meeting and talking and kind of feeling each other out uh at brunch the next saturday and uh over the course of a month like worked out kind of a deal and i joined stripe in april 2017 all right listeners now is a great time to thank our long-time friend of the show service now if you are running a large enterprise ai agents are likely spread across every team and deploying them is uh no longer the hard part yeah the hard part is knowing what

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go check out service now.com acquired and tell them that ben and david sent you lots to unpack here before we get too far into it i want to understand let's let's relate it to our previous conversation on educating and then winning had stripe or and or patrick decided that they wanted to own an asset that was sort of a community of people talking about building stuff on the internet that very likely would need stripe to monetize and then you were the pick or was it like hey wow that guy's really got something cool i think it's a combination of both it's been funny like looking at uh just acquisitions over the years talking to friends and also seeing like a little bit of stuff internally at stripe where like it's just

like so like idiosyncratic and like almost random how these acquisitions happen in many cases where it's like just like depending on how a particular person feels like this seems like the thing to buy and i think in my case stripe has this kind of cool project internally called like the crazy ideas list and it's like hey everybody write down like the craziest ideas like if it's a reasonable idea it's not allowed on this list like you need to write down like just crazy things that we could potentially do that you know might win big i think like some version of nd hackers have been on that list for many years you know like what if we have like a community for early stage startup founders just

because we're a company like stripe that wins like a lot of uh business from early startups like these startups grow you know they might be making a thousand dollars a month now but like five years from now they could be lift and so like winning like the hearts and minds of early stage startups matters a lot and so that idea was on there and they just like never did it right because there's like maybe a thousand ideas on that list and then i started nd hackers it just worked it worked really well and it just like happened to very luckily perfectly align with what they wanted to do or it's like okay well it's like empowering people to get started and inspiring them and stripe is a

company that cares like a lot about its reputation it's not an accident like that stripe hasn't had you know any sort of major scandals like almost every other huge unicorn company it's because the founders care a lot and we like have a lot of good like well among founders and developers and like make a lot of decisions at the company that like are you know have that in mind like to do best by people and so nd hackers was like also a huge check in that direction where like people just really liked nd hackers like they liked the positivity like the optimism it was all about like how you can do it you know how you can kind of stick it to the man like start your own

business was very empowering and i think crucially it did two things it inspired people to start businesses who previously might not have had the confidence to do it and it also helped people with businesses succeed and like both of those things are very good for a company like stripe that clearly wants more businesses to exist and more businesses to succeed and what were some of your concerns once you started after you got out of the initial wave of oh my god then you're like wow what would i sell this should i sell this like how did you think about some of the trade-offs intentions there yeah so a lot of my concern at the time like one of the things i was weighing heaviest on my mind was

like i just really didn't like selling ads i was really not having a great time i mean i was making money it was like fun fun to get checks but like i wanted to make nd hackers bigger and better i wanted to spend a lot more time coding the community like at that time the community only had like maybe like 40 50 conversations a week now it's got like tens of thousands and i just wanted the time to do that and so i was thinking okay well like if i go to stripe like what are they gonna have me working on you know how much say are they gonna have and what i'm doing and like how much does their vision align with what my vision is for the company and if it's off by even like a small amount

like maybe that's not a big deal today but like four or five years from now like that could be a huge deal like a small gap can turn into a really big gap and so i really wanted to know like okay are we going to be aligned i wanted to know because that's kind of like for the like the betterment of the community like the people at any hackers like is this going to be good for them you know if you have a community and you have something where like all your users are quite vocal especially if they come from hacker news which most indy hackers did uh these are opinionated people these are opinionated people and they don't like tend to look kindly on acquisitions that go wrong and watching

their favorite products die so i wanted to know okay like is indy hack is going to be better off for this i wanted to know if i was going to be better off from this you know how much money is this acquisition going to like make me right like uh how does it compare the whole point of the indy hackers right is like exactly yeah this is kind of like i'm gonna no longer be sort of like technically indy you know like what is the trade-off i'm making and like how indy will i be i have this whole point that i make to to friends and like they it always gets like a mixed reception but like i think everybody's kind of a business even if you're an employee you should think of yourself as a business

anytime money changes hands you should think of yourself as a business uh if you want to learn how to improve your career like read a business book and think about yourself as a business and so you know as an employee like yeah you might seem like you you have no power but like i learned from contracting like you have a lot of power if you can make like the value or the service or product you provide to your employer really unique like it's harder to fire you and it's like you're more valuable you can get paid more you can get paid what you're worth rather than being paid like very little because you have so many competitors have the exact same job title as you and like you know

so many other parts of like the employee experience relate to being a business you know like everybody has marketing experience if you've ever made a resume like that's basically an ad and when you've like shipped it out to you know potential employers like that's like basically marketing and if you've done an interview like you've done sales because you're trying to sell yourself so i thought about myself in that light like okay well how much freedom and independence am i going to have as an employee of stripe like who am i going to report to you know what are they going to be telling me to do if anything and i got to imagine even though this idea was on the stripe crazy ideas list for a long

time probably the reason nobody ever did it is like you got to focus on like do it you can't be like pulled in like oh yeah like i know you're doing this thing right but like hey we've got this bug like can you just like jump in and like fix it or like you know we got to do this thing like you know you can get back to doing that thing but you got to do this thing like it's also completely different and it's also like a completely different type thing like the average sort of engineer like a bigger startup is not like someone with a lot of startup experience you know there isn't like a roadmap for like here's how you start a large community of founders you know there's no like step-by-step process like

it hasn't really been done before for some reason like there just aren't large communities of founders that have like really thrived online and so uh it's kind of easier to wait for somebody else to do it than it is like pick a random employee and be like good luck you know you're gonna be able to go make you a star yeah good luck you're gonna be able i mean some people can do it but like that's not why people typically apply to jobs because that's you know if they wanted to do that they would go start their own thing so i was kind of worried you know like okay what is my responsibility going to be like am i going to be

like a normal stripe employee or not and then like sort of the third box besides just like me and the community was like what does stripe want to get out of this i really wanted to know like what stripe wanted to get out of it because it's hard to predict you know if we're going to align if i don't know like why you're even doing this and like to patrick and the leadership teams like credit like they're just very open-minded folks you know like they don't necessarily need a ton of proof that something's going to work right if something is like directionally pointing in the right direction and it can work like they're more than happy to take a chance and with like any hackers and stripe it's kind of like

nd hackers doesn't really capture a lot of the value that it creates you know if people start companies and their companies succeed because of any hackers because of a story they heard um because somebody helped them on the community like how do i make money from that like it turned out like i didn't but like other companies just that can capture that value including stripe because if stripe is the best product on the market like what are they going to use for their new companies they're going to use stripe and so patrick like really just trusted like hey we think that you can make nd hackers really big really meaningful you've done a great job so far it's hard to even measure like even if you do make it big like we'll never really know exactly

how much has contributed and sort of added when to our sales but like that's fine and so a couple of questions here and i'll ask them together so you know both are coming you don't have to give me numbers or clauses but i'm looking for broad strokes what do you need to put into a legal contract in order to allay those concerns and what do you just leave to trust because ultimately these these things really are come down to do you trust me do i trust you and are we aligned so that's the first one the second one is how on earth do you go about figuring out what a fair deal looks like based on what your business was before it was acquired yeah these

are tricky questions and i know i never feel like the most qualified to answer acquisition questions like people even though this is acquired uh people call me all the time like hey i'm going through an acquisition you went through one like what happened with you i'm like it's so specific to my situation no employees yeah i was like a solo founder with no employees like hadn't even incorporated but like there's some like little tricks and things that helped me so uh the first thing that happened was that patrick suggested that we communicate over text so we like got on whatsapp which instantly like i was like oh this is so smart because like i had been sitting there like i think it was a sunday like typing out an email like this like sort of acquisition numbers

negotiation and it was like such a high pressure thing like what am i going to say in this email like versus text it's just like so casual you're just kind of firing off like messages and like it just like lowers sort of the stress and like almost the adversarial nature of it in a strong way so that was kind of like the first tip but then i thought about okay well how do i value you know what nd hackers is worth like what am i going to be happy with here and i think your first question was also like how much does trust come into it so like the first thing i started doing was trying to answer both of these questions actually through kind of back channeling so i just emailed as

many people as i knew who either worked at stripe had dealings with stripe or had dealings with patrick in the past i'm like hey what kind of person am i dealing with and i got like a lot of really positive stories like this is a person who cares deeply about like what's good for people etc very ethical etc and like i think you need that level of trust because like in a contract as i soon found out like there's just so many random like loopholes and like edge cases that you haven't considered and just like really easy ways to get kind of screwed over like at some point i was talking to patrick and we were hammering things out and at like one point i got an email

that wasn't from patrick it was from like stripe general counsel and i'm like oh shit like maybe i should have a lawyer because i don't know what this guy's talking about so then i went and hired a lawyer and like uh her name was matal she was great but she was just like the most paranoid person ever she was like here are all the ways they're gonna screw you over they're gonna do this they're gonna do that they're gonna do this and like every single contract that like came she like found some way to tighten up the language or just like go to bat for me in ways where like because i had a lot of trust uh perhaps naively like i just would have been like ah it's fine like they have like the best

intentions here uh and so it's kind of like you know trust but verify like i had a lot of trust and i don't think i would have done the deal if i didn't trust that like everybody involved was being sincere with what they said that they're like sort of thoughts aligned with their actions and their words but also having someone in my corner to like make sure that these things wouldn't happen was i think important and gave me a lot of security yeah well the thing about these situations like this is like the documents and the clauses and all that that they exist for when things go sour you know like anytime you are looking at those documents like things are on a bad path

you know you don't ever want to look at them yeah but if you have to look at them you know what is written in those documents is what is going to happen so exactly so they're important and they matter and i think in my situation like what kind of happened is that we like agreed on numbers but like in a very like high level non-specific like this is what would make us all happy way and that happened like pretty quickly it didn't take that long and like part of that was also doing research like how much the engineers at strife get paid like can i you know by that point i was pretty good at getting people to reveal like numbers to me from working on any hackers so i got a

lot of numbers i was like okay like this is what i want and i was like try to be a firm negotiator but like you kind of agree on these numbers and then you go to like draw up a document and it turns out there's like just a million little edge cases you know like okay like if you like for example if you're talking about stock like what kind of stock do you want what like what class like when is it fast what period is it fast like how long i had a refreshes work like all sorts of different things that i think if you're kind of like a typical employee you might not consider but if you're coming in

through an acquisition like the sky's the limit like you can ask for our demand like literally whatever you want and put it in a contract that's going to be your special contract that no one else at the company has anything that's even like that so for me like it wasn't just like kind of worst case scenario it was like okay well like now it's this whole like phase two of negotiations where we're like you know talking about all these little details that we hadn't even considered you know what mechanics did you put in place obviously it wasn't like okay here's a bunch of cash welcome to stripe like it's either stock or it's vesting or it's tied to incentive based targets for indie

hackers or it's tied to stripe as a company rather than indie hackers like how did you sort of structure the way that there would be incentives over time for both sides i don't know how much i'm legally allowed to say don't even get close like i think that what we're interested is like how should people if they're going into a situation like this think about that i think the first thing to be aware of is just like all the different options that you have i think it's very easy when you think about an acquisition to just think like number you know this company sold for x amount right but like that's like from my in my experience rarely how it happens it's rarely that simple and like some of the other

options are just much more advantageous like often companies will like give you more equity then they will give you cash and if you can sort of like evaluate the company like if it's stripe like for love of god like take the equity you know yeah take the stock uh you know if it's like if it's a groupon then like i don't know you know maybe you want the cash and like this is like an exercise that well this is the difference i think between you know like like salesforce by slack it's about the number right like that's because it's a company buying it's an entity buying a corporate entity buying corporate entity with an indie hacker business like no it's you it's literally like that's

and i think they're like i don't know what like elon musk's situation is but he has like all these like weird like earn out bonuses where he gets like more money if like the stock price goes up so even like those big company situations like there's all sorts of ways to sort of like figure things out like you know if if salesforce buys slack like what does that mean for stewart butterfield like perhaps he could say like i want more money if we hit these extra targets etc and uh perhaps mark benayoff would be like sure that's fine and so i think if you can like think about kind of these creative ways to sort of like align your incentives it can you know result in like a happier process and maybe

on both sides like maybe your acquirer wants to pay you more if you hit performance targets because like the risk for them uh isn't the initial cash outlay it's that it's not going to pay off in the future and so if they know you're incentivized to like to actually do a good job then i think that that can be kind of a win-win even though like you know they're sort of on the hook for more money in the future in my particular case like it's funny because indie hackers is very much an indie hacker business you know i was just like making money from advertisers i had like some affiliate links on the site i think i was making like seven and a half eight thousand dollars a month by the time stripe acquired

the company where it's like today i feel much more like a high gross startup where like stripe owns indie hackers but they're like almost kind of like an investor and like my goal is to like grow as much as possible and like i don't make any money like indie hackers doesn't like have any sort of revenue we bring in we have kind of a budget which is almost like funding to help us grow and so it was like represented kind of like a complete change in how i viewed growing my own business and i kind of went to this uh almost to this like the exact opposite of what like the stereotypical indie hacker company is trying to do you know the comp at that point is more to intrapreneurship which is such

a funny word because it's like they took a french word and then changed it to sound like an english word to get the point across anyway what differences do you notice between indie hackers which is a wholly owned subsidiary of stripe and i'm sure that that may not exactly be technically correct but it's sort of its own brand it just has a by stripe thing on it's run by you versus the things that start within stripe but are their own self-contained thing like stripe press or like stripe atlas yeah i mean i think branding is the by far the biggest difference because it's pretty obvious to most most people who are aware of indie hackers know that indie hackers started before stripe and they know that

it's kind of like my thing i'm very transparent like they're gonna listen to this podcast and be like clearly corlan is running this on its own you know this is not like a super heavy-handed stripe initiative plus like a lot of people don't even know indie hackers is owned by stripe like there's like a very small like little logo that says like at stripe at the very bottom of the website that you kind of have to search to find which is freeing in a way because it gives me the ability to make my own decisions that don't necessarily reflect on the stripe brand like i remember a buddy of mine at stripe who kind of ran like the stripe atlas community like got an email

from indie hackers he's like oh my god you said fucking an email like a stripe email and i'm like i said fucking like i have probably like two or a dozen of these emails uh there's no one at stripe is like kind of monitoring that you know there's a lot of trust that goes both ways like i trust stripe and they trust me and like it doesn't you know it's weird in a way like i feel like a lot of the positive things and feelings people have about indie hackers sort of get accrued to stripe but like some of the riskier decisions like don't weigh on stripe at all and so it's almost best of of both worlds right whereas i think if like i you know started some stripe product internally like stripe

press like that has stripes name like literally in the name which means it's a certain like level of quality that it has to rise to there's a certain standard that has to rise to it's harder to get things off the ground when you do that like you need to match like certain accessibility standards and have like a certain reach of people in different countries and have all these different languages i think it's just harder to iterate on any sort of like startup type initiative that's trying to find product market fit if you have all of these expectations on you this is why i think it's smart for like google when they're doing their innovations to like try to like spend things out of

the google brand and just have them be like dissociated so like people don't have these expectations because you just kind of need to start with something embarrassing and rough and what i've been doing for the last youtube's a great example right like when google bought youtube there was still like the biocom lawsuit was going on like there was all sorts of you know people were up in arms there's crazy stuff happening you can maybe say there's still this crazy stuff happening on youtube although now it's like google video was a failing product like it was trying to do the exact same thing but it was going through google's standard process you know yeah they weren't gonna just you know put movies up on there that were filmed with a you know camcorder in a theater like you can take

bigger risks through an acquisition especially of like an established brand on its own that's really cool all right so tell us now why has it made sense for stripe and i mean this is a little bit of a softball question but like how's it going how's it gone was it a good idea for stripe to buy any hackers what have you built to do any integrations if you have yeah so i mean it's worth like noting sort of my working style at stripe is that i've reported to patrick since i got here we don't meet all that often you know there have been years we met like twice years where you i've sent him like weekly updates not on his request but on my request because i just wanted him to know what's going on

everything i've added to indie hackers literally everything that i've done has been 100 my choice there's not been a single request from stripe saying hey can you do this that's happened so a couple things have happened since we joined stripe i remember like meeting patrick maybe nine months after the acquisition and he was like oh this looks really good like i was kind of worried that for you to grow you would sort of have to just kind of run faster and faster because when stripe acquired indie hackers it was still primarily just kind of a media company like we were doing nothing but putting out these interviews and we had this like very fledgling community forum but like it was like you had to

like click a link to get to it and it was only like a small number of people whereas today the bulk of what happens on indie hackers is sort of user powered it's more of like an actual platform where like i'm not doing like the vast majority of the value that indie hackers creates the world is like it does not come from me you did it you shifted from media company to software product exactly which i always wanted to do but it took jesus did it take a long time um so probably i would say like the biggest accomplishment since joining stripe was just the growth of the community forum which is now on the home page if you go to indie hackers.com you just see dozens of conversations where hundreds of people are sort of

helping each other out asking questions and like helping each other start companies meeting co-founders without me really doing anything the company profiles you create through interviews and that people create themselves they're all mixed together yeah yeah kind of and i've been trying to like consolidate things they're not quite consolidated yet so there's kind of a separate section on the website where you can go and you can read and then we've done about 500 interviews now uh all the different interviews from indie hackers who've kind of shared their stories and like you can kind of sort and filter those you can also go to sort of the product directory which i mentioned earlier where it's just more like self-serve like anybody can add a product there you can share how much

money you're making share your milestones along the way and everybody's sort of there competes to have like the best milestone every day so we have this leaderboard that kind of resets and whoever posts like the best update for that day in terms of upvotes gets to the top of the leaderboard and they get more traffic etc and so it's kind of a mechanism to incentivize people to fill out these little timelines which has a side effect that everybody else can go read the timelines and learn how to build a company from these examples so that's grown to like 12 000 products we've got 500 interviews we have a podcast that you know went from i think just maybe like a thousand downloads total

when stripe acquired indie hackers to now millions of downloads and the community forum has gone from just a few dozen conversations a week to the point where there's like a thousand comments a day over 250 posts every single day in the community forum and just like tens of thousands of people helping each other out so uh you know based on the numbers indie hackers has grown like tremendously since we've joined stripe so awesome and one of the things like we like to measure is kind of like a rough estimate of like how many people have started companies as a result of indie hackers so we kind of send out like a survey to people maybe six months or so after they join and you know we ask

them to say like true or false to different questions and one of them is you know you know would you have started your company if not for indie hackers and most people are like oh yeah i would have started it anyway or i haven't started yet but a good 15 to 20 percent of people depending on the month say they would not have started their company if they didn't encounter some story or some person on indie hackers and if you multiply that by like 140 000 you know different people who've joined the community forum like that's that's a very substantial number of companies a lot of companies a lot of tiny companies and some of them have like gotten bigger gotten acquired a lot of them are on stripe

and sort of the way that patrick explained to me earlier when i first joined stripe was like hey it's your job to you know get people to start companies it's our job to have a product that's good enough to win them over you know i'm not like sitting here trying to like hawk stripe and convert people to stripe like that's something that stripe does on its own and what was that 140 000 user number when you were acquired ish let me look it up i'm also curious i'm this is the third time i've done this to you i'm queuing up two questions approximately what percent of indie hackers use stripe as their for their company so the second one i don't know the answer to we don't really have like a process like we don't measure

you know like there's like it's a lot of just trust right okay like we know this stripe is pretty damn good as a product uh comes up on the community forum all the time i think it was the most referenced company and all the interviews that i did even before joining stripe i mean honestly i don't even know what else you would use if you want to take payments on the internet you could use a ton of other stuff but they're just like custom services that are white labeling stripe underneath like that's what glow is like yeah like i don't even know if there is another alternative it's it's it's a really good product yes david there are alternatives it is also a very very very good product

so for me to alternatives worth using let's put it that way so for me to answer your question on exactly how many users are right when i joined stripe i have to run like kind of a query it'll probably take me like a couple minutes so like is it worth it on air sequel writing well do you have any mental ballpark of like on the order of a thousand ten thousand it was on the order of like certainly fewer than five thousand probably more than a few hundred all right that helps us understand i think the the scale and it's been what three and a half years yeah it's been three and a half years i joined in april 2017 so and the hackers has been a stripe for much much longer than

it existed before stripe that's really cool even just like super ballpark numbers let's say 100 000 companies added since the stripe acquisition 15 to 20 percent indie hackers played a major role in that company being started it's 15 to 20 000 companies presumably a large portion of them are using stripe like that seems like a great outcome for stripe the really interesting thing to me and now we're in so for people who listen to more acquired episodes we've been through history and facts a little bit right now we're in what would have happened otherwise and and then we we've done a lot of playbook as well but we can specifically call that out you know if stripe hadn't acquired indie hackers it's not like all the companies that have been created wouldn't have used stripe

like i don't think you'd influence their any of their decision on what you know who to use for payments so what they were really doing is saying like man this thing is really good for our business that it exists let's make sure it can thrive as much as possible it's interesting to me trying to think through the scenario where stripe didn't acquire indie hackers and the exact same outcome happened for stripe yeah again like i don't measure you know would you have used stripe it's not even my goal really to like make people use stripe it's my goal to like make people start companies right i want people who like would never have started a company because they didn't think it was possible they

hadn't seen anyone like them start a company they didn't see a path like when they hear a story on the indie hackers podcast when they go on the forum and they see somebody who's like like i met a yc founder at the stripe event a couple years ago and i was just kind of talking to him and he's like yeah i love indie hackers i'm like uh you know what's your experience with it he's like oh i read the story you did with this guy who started this like review site and i'm like i'm way smarter than this guy i could start a company so i did then i got into yc and now i don't go to indie hackers anymore

and like that's that's pretty that's pretty common like i meet a lot of people like that who were just like inspired like they literally started because they just read that it was possible and when i think about like me like i started my career because like people told me it was possible you know and i think spreading those stories helps people get started and like that's literally all i care about like i don't care how many of these people end up using stripe like that's the job of stripe engineers and product managers like make stripe the best product all right so it looked like you were uh you were writing some sequel there in the background while i was pontificating what'd you come

up with so we've got we had exactly 1403 users on the day that we got acquired by stripe so we're 100x bigger today almost exactly 100x bigger yeah almost exactly 100x just pretty cool it's cool to see how that i mean wow that's that's cool there's a lot of stuff to look into too it's like okay well how much bigger is the podcast like how many more conversations are people having because it's not just about having more people but it's about engaging them more uh how many like return visits to people have and we track a lot of random stuff but like number of users straightforwardly 100x bigger in three years it's awesome i mean it's it's a it's a bet on the internet it's a bet on the internet

being able to enable people to create far more companies than they otherwise could have did you see these these stats that came out um last quarter about like new business creation where it's like like yeah like 600 people or 600 000 people a quarter in the united states were creating businesses like 10 years ago and then last year it was like 800 000 people a quarter and this year it's like one and 1.6 million people created a business or filed to start a business in like q3 2020 which is insane like so it's doubled like aren't there more and more winner take all opportunities like are we seeing now we're well into playbook but uh are we seeing basically like a barbellification where

the big startups consolidate to only a few big winners in each market but then there's like massive massive opportunity to go after a long tail yeah i think number one there's a lot of these winner take all startups but almost all of them create sort of niche business opportunities for other founders and so it's not like this exclusive thing like oh they took the facebook took the social networking market now there's no business opportunities well it's like turns out a ton of media companies get started off the back of that and a ton of like app companies get started off the back of that and like there's companies that like teach you how to build a facebook page it gets

started off the back of that so like i think as an nd hacker you don't have to worry too much about the winner take all companies uh and then we have all these like platforms you know youtube substack only fans arguably you know twitter where people are just like building audiences and businesses off the back of all those things and so what's kind of cool is it's kind of like never going to be you know all the niches are taken there's no ideas left and also i think what people underestimate is just the number of people adopting technology for the first time because just because like zoom exists doesn't mean everybody uses it like we've seen very clearly this year way more

people are using zoom because they've been forced to adopt this thing they've been kind of ignoring in the past because they just like didn't want to and so as more and more people get on the internet and create businesses and like use these products it's more opportunities and then like most successful nd hacker businesses sell to other businesses so it's kind of like this self-fulfilling sort of chain reaction where the more businesses there are the more like products they need and so it's kind of cool to see it accelerating and i wouldn't be surprised if that number you know in a few years it's like five million americans a month are creating an online business yeah that's what i was thinking on

that is like you know you've got the platforms like say let's look about stripe or shopify like say and then you've got people that like start shopify stores or start businesses on the internet and you stripe but then there's this whole other category that i think is like perfect for indie hackers of like oh well there's actually stuff that you can build to help the people that are using shopify that are using stripe that like you know there's so many businesses that have been started around shopify that are like and stripe too that are like not a business on shopify they are a business that provides a custom set of tools for a certain set of users that need like hobby businesses like you're a hobby

game store and you are both buying and selling from your customers like your customers come and they trade in stuff like you can run on shopify great but like you also need some custom functionality to buy stuff from your customers boom businesses like i think like a lot of the smarter like founders are figuring out ways to kind of escape the competition because it's like okay you can build like a shopify plugin but there's like a lot of other shopify plugins so it's a cool opportunity but then you get kind of crowded out like i'm talking to a guy tomorrow his name is jordan o'connor he's got like a really cool story where he's like you know a father a husband he had a full-time job and he would like eke out

time every morning to kind of work on his business because he knew that like after like 8 a.m his son was going to be awake he's going to have no time at all to do anything and so what he ended up doing was kind of escaping the competition and he built a bot for this app called poshmark which is huge like a lot of people buy and sell like their used clothing on poshmark but they don't have a marketplace like they have no like they don't even have an official api so he just sort of like reverse engineered things he's like there's not going to be any competition here but it's kind of the same playbook like build you know for this an ancillary tool for this bigger platform and he built like

kind of a bot that helps you like do well on poshmark and i think he got to like 20 grand a month and now he's just kind of like he quit his job he's just kind of set and he's just like doing other fun projects now that like you know interest him from year to year while that bot just kind of makes money for him in the background magic of software it's pretty crazy all right listeners now is a great time to talk about one of our favorite companies statsig yes long time acquired partner there is a reason why the best product teams at companies like open ai and notion atlassian figma rippling bricks and more rely on statsig whether they are iterating on their core product features

or shipping ai powered experiences at scale yep in the crazy speed of today's ai world shipping fast is just table stakes now it's basically trivial to build and deploy your app constantly the real advantage is how quickly you learn what changes actually created value for customers and how fast you can use that signal to guide what you ship next whether it's a feature tweak a pricing change a performance improvement or an ai update like a model change or prompt adjustment they're not relying on instinct they're measuring what actually moved engagement retention and ultimately revenue and as more teams build with ai that learning loop becomes even more important building with llms introduces non-determinism into your product experience the same input doesn't always produce the same output

and behavior can shift in subtle ways in real world use so doing offline evals will give you part of the picture but you can really only understand the impact once your product is live with real users and then you can measure how their behavior actually changes it's very different than the way that you would ship features in a pre-ai world where you knew exactly what the software was going to do in production yeah exactly so this is where statsig comes in it brings experimentation feature flags and product analytics into one unified system so teams can ship safely test rigorously and directly link what they changed to how users actually behaved the result is a tighter feedback loop and learning that compounds

over time so you don't just ship more you ship better so if you want to make learning your competitive advantage whether you're building new ai experiences or just evolving your existing core product go to statsig.com acquired to get started all right well i'm going to start bringing us home here courtland answer this question however you see fit but how would you grade the indie hackers acquisition by stripe in terms of was that a good use of capital and resources for stripe oh a plus i think it's uh i'm slightly biased here you know like stripe is a company as you may know that has lots and lots of money and the indie hackers acquisition did not cost billions of dollars i think it's generated only

goodwill towards stripe more customers more users towards stripe and i think it's done well for literally everybody involved i think stripe's happy to have it i'm happy to be a part of stripe and i think for the people who use indie hackers they're very concerned early on you know they're very worried and i don't think i've met a single person who said like they aren't happy that it happened so it's hard to imagine it having gone better yeah should more people do this i mean the way that i'm sort of categorizing this in my head is they made an investment to ensure the continuity of this thing that was creating new customers for them and like do other companies do that should have more companies do

that i think they should be a lot more creative and imaginative i think like there's like as humans we have this impulse to just like to just like mess with things it's really hard to buy something and then not touch it you know it's really hard to do that and i think when people think about like okay if i buy this like what am i going to do with it i think oh it's going to be like so much work i have to do this i have to do that and they don't like make these acquisitions whereas i think it's stripe they're very much like no cordon's doing a good job and we don't have to do anything and like if we

can just ensure that it keeps going like you said like that's a huge win by itself but there's other wins too you know i think one of the trends we're going to see going forward is like tech companies basically owning like some kind of media company which i think is super powerful because like media companies are what connects with actual people on the ground and in a way like any hackers is still very much a media company like i still spend a lot of time on the podcast we spend a lot of time on our newsletter put out a ton of content and we're sort of like becoming a platform almost like substack ask where we're enabling other people to sort of build newsletters and grow their audiences on

indie hackers so i think like even without just like having indie hackers continue to exist and even without it like driving excess additional customers to stripe it's just a good way for stripe to be able to communicate in the future if it wants to you know we're launching this thing or like you know we're we think this about the world and like now they have a place that's not just hacker news or twitter to do that has stripe done any anything else like this since you've been bought or yeah stripe has a magazine called increment magazine uh just increment.com it's kind of like the best sort of magazine for all sorts of basically work that gets done so they've done like issues on like

software engineering and apis and the cloud and being on call and like people love this magazine it's really well produced it was created by kind of initially susan fowler who's the engineer who kind of blew the whistle on uber back in the day and now she works i think at the new york times so that's like a really cool like stripe project that i don't think it's enough press and attention there's also like stripe press which is kind of like an in-house thing it wasn't like exactly acquired but all these sort of initiatives i think you know involve often people who are like come in from outside the company and help they're all like kind of moonshots you know i put it in a

very similar category to nd hackers even though it's like you know different but it's something that most companies like wouldn't do but like stripe kind of trust like okay well what if we put out like these books uh that like help people become better founders make better decisions to start more companies it's hard to measure like how many people actually read this book and made a decision because of it but like we can kind of trust that like they will do that because like we know that's how inspiration works and like it'll increase stripes bottom line yep makes total sense for acquired listeners because i know we're releasing this in in both feeds where can people find you what should

they check out first of of the various indie hackers and courtland properties yeah i mean the easiest way to really get into indie hackers is the podcast so if you just go to your podcast player and search for indie hackers it will come right up top for you uh check out any of the episodes they're all pretty good they're all different stories of founders and how they've succeeded and so i just recommend listening to a few of them and really absorbing like you know what is this path like you know how can you start off maybe as an indie hacker and then eventually grow to start a much bigger company i've interviewed like lots of founders of like yc funded companies and vc funded companies but also

tiny indie hackers you don't want to grow anymore so check out the podcast and you can find me on twitter at cs allen awesome well listeners we hope you have a happy holidays it has been one of the best parts of our 2020 being with you all and we will see you next time we will see you next year cannot wait for 2021 but seriously like it's been the best part of 2020 hanging out with you all virtually it's just been a great year the world aside it's been a great year for acquired community can't wait for next year see you in 2021 everyone you