Special: Acquired x Indie Hackers

As regular listeners know, we typically cover some of the biggest companies who often receive the most media attention (see Airbnb and DoorDash). But today's episode is a little different. In our conversation with Courtland Allen of Indie Hackers, the largest community of startup founders, we dive into the stories of underdogs. What happens when there are millions of people doing small business entrepreneurship? How does anyone having access to the globally addressable market of 3 billion internet users open the door for the niche-est of products? We tell the story of Courtland’s own “Indie Hacker” journey, how he came to found Indie Hackers itself, and the lessons learned along the way. Sponsors: Vanta: https://bit.ly/acquiredvantaServiceNow: https://bit.ly/acquiredservicenow26Legora: https://bit.ly/acquiredlegoraStatsig: https://bit.ly/acquiredstatsig26 More Acquired! Get email updates https://www.acquired.fm/email with hints on next episode and follow-ups from recent episodesJoin the Slack http://acquired.fm/slackSubscribe to ACQ2 https://pod.link/acquiredlpMerch Store https://www.acquired.fm/store! © Copyright 2015-2026 ACQ, LLC Playbook Themes from this episode are available on our website athttps://www.acquired.fm/episodes/special-acquired-x-indie-hackers Links: Indie Hackers: https://www.indiehackers.com https://www.indiehackers.com/

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00David Rosenthal?

  I've got new M1 MacBook Air. It's the first episode we're doing on it. Nice.

• 0:05Ben Gilbert?

  Nice silent recording in the background.

• 0:09David Rosenthal?

  No, what do they call it on the Pro?

• 0:11Ben Gilbert?

  The Active cooling system. Don't call it a fan.

• 0:25Ben Gilbert?

  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.

• 0:39David Rosenthal?

  And I'm David Rosenthal and I am an angel investor and advisor to startups based in San Francisco.

• 0:46Ben Gilbert?

  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 Courtland Allen of Indie Hackers, 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 niche-iest of products? And importantly, what was Cortland's lived experience of starting his own string of companies that ultimately led to starting Indie Hackers?

• 1:30Ben Gilbert?

  And its acquisition by what is now the hottest private company in the world, Stripe.

• 1:37David Rosenthal?

  Yeah, man. Last one left standing after last week.

• 1:42Ben Gilbert?

  No kidding. And a lot of people cannot wait for it to IPO soon enough.

• 1:47David Rosenthal?

  Okay, that's gonna be, I gotta imagine our biggest episode of next season, hopefully next season? When is this thing gonna happen?

• 1:54Ben Gilbert?

  Season eight, season nine. We'll see, David.

• 1:57David Rosenthal?

  We'll see.

• 1:58Ben Gilbert?

  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/lp. All right, listeners, now is a great time to tell you about a longtime friend of the show, Vanta. AI has scrambled the whole security picture.

• 2:41Ben Gilbert?

  It used to be that you proved that you were secure once a year on audit or a static PDF, then everyone would nod and you're done. But in an AI-first world, that doesn't hold up anymore.

• 2:51David Rosenthal?

  Yep. Your risk surface changes every week now. A vendor turns on an AI feature, or someone writes in a new model without telling IT, and your posture is different than it was last week, let alone at your last audit. Vanta's own research found that around 70% of companies have this "shadow AI" running with no security review at all.

• 3:12Ben Gilbert?

  Right. And that's where Vanta comes in. They're the leading agentic trust platform, meaning they've built the thing that closes the gap. And the way that they close that gap is Vanta Agent. Think of it as a GRC engineer, that's Governance, Risk and Compliance, except that it's software and it doesn't sleep. It finds the issues, drafts the fixes, and cuts the time that you'd spend on vendor assessments in half.

• 3:33David Rosenthal?

  In half! Which is exactly why more than 16,000 companies today run on Vanta. Companies like Ramp, Cursor, and Snowflake all stay audit-ready and catch the risks that crop up between audits across every vendor, every AI tool, the whole environment.

• 3:52Ben Gilbert?

  And that's the real value. Trust has to be continuous now, which is why Vanta automates your security, your compliance, and the work to earn and prove trust. We're huge fans of Vanta over here, and literally hundreds of Acquired listeners have become Vanta customers at their companies over the years. So you can get $1,000 off Vanta at vanta.com/acquired. That's V-A-N-T-A dot com slash acquired for $1,000 off, 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.

• 4:26Speaker 02

  Ben, David, thanks for having me.

• 4:29David Rosenthal?

  So great to have you here.

• 4:30Ben Gilbert?

  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.

• 4:45Speaker 02

  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.

• 5:01Ben Gilbert?

  Well, look, we are the Acquired podcast and you did that mega deal exit to Stripe. So how could we not?

• 5:06David Rosenthal?

  Yeah.

• 5:07Ben Gilbert?

  You know, cover the acquisition of the century.

• 5:08David Rosenthal?

  This is great. It's got like all the hallmarks of both of our episodes.

• 5:12Speaker 02

  We'll see how that goes.

• 5:14Ben Gilbert?

  Well, David, who is Cortland for listeners who don't listen to Indie Hackers or haven't participated in the community?

• 5:20David Rosenthal?

  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. 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, 1,000 times bigger than the Rockefellers and the Carnegie's 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

• 6:04David Rosenthal?

  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.

• 6:20Speaker 02

  Indie Hackers is not a, not a big splashy go for broke story, David?

• 6:26David Rosenthal?

  I don't know. You're gonna tell us.

• 6:27Speaker 02

  It's really not. It's really the story of, I like to think of it as the underdogs. You know, like 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, it's becoming possible to like sit down in your living room, uh, wearing your underwear or whatever you're wearing and just create something that's super valuable to your community and your customers. Uh, 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.

• 7:10Speaker 02

  So, uh, thousands of people are doing this today. And the question that like I'm asking myself constantly is like, what happens when millions of people are doing this five or 10 years from now?

• 7:17David Rosenthal?

  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 a 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.

• 7:41Speaker 02

  A lot bigger.

• 7:42David Rosenthal?

  A lot bigger.

• 7:44Ben Gilbert?

  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, uh, was geographically constrained and they could, that you could have a general store that sold everything, but it could only sell everything to the people in your town. And obviously the, 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, I continue like Cortland from listening to your show, every time I listen to an episode, I, 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

• 8:27Ben Gilbert?

  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 three billion people, uh, with the internet, then every niche within that TAM can be on its own big.

• 8:44David Rosenthal?

  Hey man, Starlink's coming soon. It's gonna be 7 billion.

• 8:47Speaker 02

  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 gonna 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.

• 9:11David Rosenthal?

  I hear the real estate is cheap too, though. 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?

• 9:25Speaker 02

  So I had, I was just talking to Jason Kalakonis 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 hijinks startup, selling computers and stuff in the 90s. And my dad was part of like, like this elite team of like furniture makers. There was 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

• 10:08Speaker 02

  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 lives who kind of showed me that you can do pretty much whatever you want and like kind of scratch out a living.

• 10:20David Rosenthal?

  Yeah, you can do this and like it'll be fine. You can have like a good life, right?

• 10:24Speaker 02

  Yeah, exactly. You can have a good life, you know, like we were eating, 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 and 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 adults perspective around me, they're like, oh, this is a computer whiz. You know, whenever I've got a computer issue, Courtland 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 I said, 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.

• 11:06Speaker 02

  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, okay, I want to be Bill Gates, you know, I want to start my own company. I want to go to good college. Like, how do I, how do I get on that path?

• 11:41David Rosenthal?

  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.

• 12:02Ben Gilbert?

  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 core. 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.

• 12:21Speaker 02

  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.

• 12:41Ben Gilbert?

  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?

• 12:54Speaker 02

  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?

• 13:04Speaker 02

  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 gonna 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,

• 13:46Speaker 02

  and like encouragement, and like, privilege in a way. And so, yeah, by the time I like, I left, to go to college, I felt like, pretty ready to take whatever the world was gonna 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.

• 14:07Ben Gilbert?

  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.

• 14:20Speaker 02

  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 they're 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, no one died, you know? So I think that's kind of what I got out of it.

• 14:47David Rosenthal?

  I assumed 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 me to MIT.

• 14:54Speaker 02

  The Kenny G phase was, 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'd 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.

• 15:36Speaker 02

  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. Cause 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.

• 15:47Ben Gilbert?

  Well, how many companies have you started now?

• 15:49Speaker 02

  Seven. Andy Hackers is my, my seventh attempt to do something that worked. And the only one that really, that really worked.

• 15:57David Rosenthal?

  So yeah, I was gonna say, so when you get to MIT, you, I think if I understand the history, you start applying to YC like regularly.

• 16:06Speaker 02

  Yeah, yeah, I played a lot of times.

• 16:07David Rosenthal?

  So is this like a, like a every quarter thing? It's like register for classes, put in the YC app.

• 16:13Speaker 02

  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.

• 16:35David Rosenthal?

  Had Dropbox already gone through YC at this point?

• 16:38Speaker 02

  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, no, 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.

• 17:05Ben Gilbert?

  This is just as good as getting in.

• 17:08Speaker 02

  Basically.

• 17:09David Rosenthal?

  Oh, that's what were some of the ideas you were applying with?

• 17:12Speaker 02

  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, cool. And just go learn PHP. I'm like, PHP, like, what is that? So I went online and I started learning it. And he's like, okay, like, well, how do I extort user information?

• 17:34David Rosenthal?

  Facebook was all PHP.

• 17:36Speaker 02

  Yeah, yeah, it was all PHP. And like, I just kept asking like, oh, how do I do this? He's like, oh, just go learn like, MySQL. And like, 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. Uh, 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. They're like, oh, crazy MIT genius, figures out a way to put Gmail inside of Facebook. And like, we'd skinned it to like, look like Facebook. And like, 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.

• 18:19Speaker 02

  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.

• 18:27Ben Gilbert?

  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 flood 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, that's what everybody did then. And that's even what Facebook was written in, David, as you mentioned. And, uh, the web was like, uh, it felt like a small place.

• 19:04Speaker 02

  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 gonna get, like, 10 billion results. But if you talk, like, "the dog left," you're gonna get, like, a million results. And if you're like, type, like, "the dog left the store with a bone," there's gonna 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 then the same thing

• 19:49Speaker 02

  is true with ideas. So I think there's always kind of like this, 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.

• 20:01David Rosenthal?

  Yeah. Okay. So you mentioned Hacker News, which I assume is gonna continue to play a big role in the story here. What, um, were you hanging out on Hacker News while you're at MIT and doing all these YC applications?

• 20:14Speaker 02

  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 was 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.

• 20:35David Rosenthal?

  Yeah. Ben, you know the story, right?

• 20:37Ben Gilbert?

  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 there, that subreddit didn't exist yet and got frustrated with their slowness and started Hacker News on his own.

• 20:54Speaker 02

  Yeah, that's hilarious. So he's like, yeah, this is not good enough. Even though he's an investor and 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 gonna look at what, like, 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.

• 21:29David Rosenthal?

  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.

• 21:43Ben Gilbert?

  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.

• 22:04Speaker 02

  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 impersonal 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.

• 22:28David Rosenthal?

  Yeah.

• 22:29Ben Gilbert?

  So catch us up there. So what, what idea did you end up going through YC with?

• 22:33Speaker 02

  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.

• 23:12Speaker 02

  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, 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, let's just do that. So I met another guy, again on Hacker News, who like kind of posted like, hey, I'm looking for a co-founder.

• 23:39David Rosenthal?

  Yeah, I was gonna say, I read that. Like, you met your co-founder on Hacker News, right?

• 23:42Speaker 02

  He was like one of my previous competitors from my earlier email thing. And his app 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?

• 24:08Speaker 02

  So I can pay my rent this month.

• 24:10David Rosenthal?

  Was this, uh, what, was this, what, 2011?

• 24:12Speaker 02

  It was like, uh, like, we did winter 2011 for YC. So this was like, in the fall of 2010. Like, November, December, we were applying.

• 24:19David Rosenthal?

  Before the Yuri Milner, SB Angel deal, where you got...

• 24:24Speaker 02

  That happened during our batch. That was like, the, like, we were the very first batch for that. And 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 in SF and just eating like, a lot of like, oatmeal and crackers and stuff. And then I remember, uh, 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, and 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.

• 25:06Speaker 02

  And I was like, yeah, we're gonna 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, okay, well, I'm gonna start eating, like, I'm gonna upgrade to ramen now. And, uh, not have to worry about where my rent's gonna come from.

• 25:23Ben Gilbert?

  So we structurally understand that. Was that a convertible note that they invested on with that?

• 25:28Speaker 02

  Um, 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.

• 25:38Ben Gilbert?

  But it wasn't like, literally free money?

• 25:39Speaker 02

  No, it wasn't literally free money. Like, there were strings attached, but I...

• 25:42David Rosenthal?

  I think it was uncapped, though.

• 25:43Speaker 02

  It was a really good deal, and none of us questioned it. Like, we just signed, we just signed the papers.

• 25:48David Rosenthal?

  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.

• 25:56Speaker 02

  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 it 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, Cortland, 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, Cortland is this far along in the to-do or Cortland 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

• 26:39Speaker 02

  of IC, I think we had like 100,000 users. But back in the day, like that was nothing. You know, 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.

• 26:55Ben Gilbert?

  I'm also dying over here because after Hacker Follow, my first app was a task list that I launched for iOS 3, which was 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.

• 27:22Speaker 02

  Yeah, I think it's still there. Like, if you know the right combination of keyboard shortcuts, like you could 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...

• 27:44Ben Gilbert?

  But we'll do it in email.

• 27:45Speaker 02

  Yeah, we'll do it in email. 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 are like, no, I haven't. Maybe I should sign up.

• 27:57Speaker 02

  So we kind of combined those things and we got to demo day in YC, 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's this really going? And we've invested in email startups in the past and they're all dead. Like, what's, what's going to make yours different? And we didn't have a good answer to that. So we went to the summer after YC with like, probably still like 120, 130 K 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?

• 28:25David Rosenthal?

  Again, if we have our lore right, one of the talks, maybe like, was it like a Tuesday dinner talk while you're on YC was Kevin Hale from Woofoo?

• 28:33Speaker 02

  Yeah. 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.

• 28:50David Rosenthal?

  Drive up in the Lambos.

• 28:51Speaker 02

  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.

• 29:06Speaker 02

  And then Kevin Hale came in from Woofoo and he was just 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, 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. Cause like Stripe wasn't even in beta at the time.

• 29:36David Rosenthal?

  It wasn't, so like in your cohort, nobody was like, talking about like?

• 29:39Speaker 02

  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, we 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 like 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. You're kind of jealous too, because like, you know, 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 woofy 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?

• 30:24Speaker 02

  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. 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?

• 30:44Speaker 02

  That's so funny.

• 30:45Ben Gilbert?

  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, 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 Cortlands building profitable businesses?

• 31:05Speaker 02

  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 just 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, okay, you gotta go for a billion, you gotta go for a billion, you gotta be a unicorn. They're like, do whatever it takes to survive and get to the next stage.

• 31:47Speaker 02

  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 were 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?

• 32:08Ben Gilbert?

  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?

• 32:35Speaker 02

  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, Indie hackers today is, to my knowledge, like, the biggest online community of startup founders. Indie 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, hey, 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, is 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

• 33:19Speaker 02

  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.

• 33:32Ben Gilbert?

  I love that. And without jumping too far ahead to indie hackers, 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?

• 33:50Speaker 02

  Startup founders.

• 33:51Ben Gilbert?

  Startup founders. That's cool.

• 33:53Speaker 02

  I mean, they're indie hackers. 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 indie hackers I talked to are like, are no longer even indie hackers. They've raised money, they're building bigger companies. And that's like, where their life path took them.

• 34:22David Rosenthal?

  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 indie hacker 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, and sometimes they become indie hackers. And sometimes they become just a business that makes you a couple hundred thousand a year.

• 34:48Speaker 02

  Yeah, exactly. Like, I don't like to juxtapose indie hackers like as a, as a counterargument to like raising money so much as it is a counterargument 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 indie hacker 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 indie hacker is really this like this confidence in yourself that 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.

• 35:25Ben Gilbert?

  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.

• 35:47Speaker 02

  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 that 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.

• 36:06David Rosenthal?

  They're wearing t-shirts instead of seats. But they're doing the same thing.

• 36:09Speaker 02

  Exactly. But 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, 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 and D. And they're making like a hundred 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.

• 36:53Speaker 02

  And it's like, it's not just like your traditional idea of a business, you know? 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? Well, at the same time, he's like, kind of getting rich and making everybody feel great.

• 37:10David Rosenthal?

  I think this is like such a big movement alongside, you know, the traditional startup, raise 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 Rockefeller's of the world.

• 37:36Speaker 02

  Did you guys watch that series Chernobyl? It was on HBO last year.

• 37:39Ben Gilbert?

  Oh, it was so good.

• 37:40Speaker 02

  Great series.

• 37:41David Rosenthal?

  Oh, no, I heard about it.

• 37:42Speaker 02

  It was good.

• 37:42Ben Gilbert?

  Freaky.

• 37:42Speaker 02

  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, don't unsubscribe from HBO. But, uh, the, uh, 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. Cause 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.

• 38:27Speaker 02

  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?

• 38:51Ben Gilbert?

  When this comes out, we will likely have just done the DoorDash and 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, 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 100,000 stories of businesses and the playbooks that they ran on your website. Like, someone can find an incredibly narrowly

• 39:34Ben Gilbert?

  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.

• 39:45Speaker 02

  Yeah, exactly. That's kind of the goal of like, a lot of the things that I'm building on Indie Hackers. 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 the profile of what you're trying to build? And so we have, like, this directory that I kind of half-hazardly built, like, two and a half years ago. And I was like, oh, we should have a directory of products. And 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 there's, like, 12,000 products on there. And they all have, like, a little timeline where they're, like, saying, okay, here's where I launched, and here's what I thought about my launch.

• 40:18Ben Gilbert?

  I thought I was being ridiculous, saying 100,000, but it shouldn't be long.

• 40:22Speaker 02

  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.

• 40:35Ben Gilbert?

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• 40:49David Rosenthal?

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• 41:03Ben Gilbert?

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• 41:13David Rosenthal?

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• 41:31Ben Gilbert?

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• 41:47David Rosenthal?

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• 42:03Ben Gilbert?

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• 42:13David Rosenthal?

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• 42:24Ben Gilbert?

  I'm gonna do David's job here. So take us from the light bulb of Taskforce should be making money to the founding of Eddie Hackers. How did that period of time happen?

• 42:34Speaker 02

  Yeah, I'll give you, I'll give you the whirlwind story. So at some point during the summer after YC, Stripe came out of, 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.

• 42:46David Rosenthal?

  Were they in your batch? Or were they, they were before you, right?

• 42:48Speaker 02

  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 gonna make like a hundred dollars 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. It's 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?

• 43:31Speaker 02

  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 pedaled on the metal on my computer every day, coding as much as I possibly could. Like, this is gonna be it. You know, like, I'm gonna succeed. Like, this is gonna be it. Like, it has to work. And like, it never did.

• 44:17Speaker 02

  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 lives, because I was like literally just doing the same thing every single day. And now my, my model that I have for it, kind of framework and the way I think of it, and the way I wish I 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 gonna 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.

• 45:00Speaker 02

  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, 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 Indie Hackers 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 gonna work? Is this gonna be the one?

• 45:38Ben Gilbert?

  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?

• 45:50Speaker 02

  Yeah, like the first one or two were kind of inside the same entity. And then my co-founder 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 like, 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 you 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.

• 46:34Speaker 02

  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'd 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, 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, 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 been 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?

• 47:18Speaker 02

  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 gonna 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.

• 47:39Ben Gilbert?

  Yeah, default alive, or at one point I ran a startup weekend in Seattle and Bo Lu, who actually I think went on to do 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're on the act of succeeding until you call it quits."

• 48:06Speaker 02

  Exactly.

• 48:06Ben Gilbert?

  That's always stuck with me.

• 48:08Speaker 02

  Yeah, 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 gonna eventually get there. Who knows how many startups it's gonna 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.

• 48:24Ben Gilbert?

  All right, so, the genesis of indie hackers.

• 48:27Speaker 02

  The genesis-

• 48:28Ben Gilbert?

  How did that happen?

• 48:29Speaker 02

  So, I just rolled off a contract job, and I had about a year of runway in the bank. So, I was like, "Okay, here we go. Like, take four. I'm gonna, I'm gonna figure out like, something to work on that's gonna work this time. You know, worst-case scenario, it's gonna all fail and I'm gonna 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 ment 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. Like, this is gonna 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 10 grand a month. And like, I hadn't even launched my thing yet. So, I was like, "Okay, this is like a dud. I should scrap this and go back to sort of the drawing board and figure

• 49:14Speaker 02

  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'd 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 indie hackers in exactly three weeks. And it didn't require very much code at all, didn't require like, a lot of marketing or anything. It was just like, super, super easy. And 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?

• 49:58Speaker 02

  And like, the other lever people pull is like, oh, how do I get more time? You know, maybe I'm gonna work nights and weekends and all this stuff. And like, wanna work a three-day work week instead of five-day work week. 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 wanna 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 wanna do next. A ton of other people clearly wanna 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 kinda 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?

• 50:42Speaker 02

  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 kinda my idea, kinda phase one. Like, I didn't have a revenue model. I didn't know where I was gonna 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 gonna eat it up, because they've already been eating up stories like this before.

• 51:20Ben Gilbert?

  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.

• 51:32Speaker 02

  A hundred percent it's going to be a business. I don't know how I'm going to make money yet, but it's a hundred percent. 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.

• 51:54David Rosenthal?

  The revenue aspect, maybe revenue and profit aspect of the stories you were telling. Was that super key? Like, cause I can imagine like, you know, 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 the like, like that feels like so, 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, do, how important was that?

• 52:22Speaker 02

  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, does this and this and this. And like, they don't share their 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 upload the stories that share their revenue numbers. We only want to upload 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.

• 53:06Speaker 02

  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.

• 53:11Ben Gilbert?

  And so Don't train your model on garbage data.

• 53:13Speaker 02

  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, uh, you know, my name's Coraline, I'm starting this website. It's gonna 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, you're, 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.

• 53:57David Rosenthal?

  When you launched, you built the site, right? So like, you didn't go to Squarespace, you didn't go to Webflow. You did, what, what was the thinking behind that?

• 54:05Speaker 02

  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. I learned how to do front-end development and back-end and like server admin stuff. And here I was, like, going to sort of 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, 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.

• 54:46Speaker 02

  Even though that's gonna 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.

• 54:54David Rosenthal?

  You weren't yet thinking like Stripe Revenue Connect, like, you know, building a community and like, yeah.

• 55:01Speaker 02

  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'd 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 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

• 55:44Speaker 02

  named after kind of a new class of people. Because I was like, well, there's no name for like these people in 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. 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 Medium, it all looked the same. And so I wanted mine to stand out. So that 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. Like, I didn't like the

• 56:29Speaker 02

  platform risk. I'd been kind of burned by that before, building on Gmail. And 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.

• 56:49Ben Gilbert?

  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 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.

• 57:31Speaker 02

  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 there were like indie developers. I was just like, okay, 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, okay, you're a programmer, but you're independent. There's no cap on your salary. You know, there's really no limits. Like, you can do whatever you want.

• 58:06Ben Gilbert?

  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

• 58:49Ben Gilbert?

  you think about how far you should go on eliminating platform risk?

• 58:53Speaker 02

  Yeah, I think everything in business is basically a trade off. And what you really want to do is just be like aware of the trade offs 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 it can give you additional distribution, but then you get the risk that they might shut you down or change things. So 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 could spend more to acquire your customers. It's all trade offs. And so for my particular situation, when I looked at that trade off, 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 were the

• 59:35Speaker 02

  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, and 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 gonna be eating this kind of stuff up on Hacker News,

• 1:00:18Speaker 02

  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.

• 1:00:30David Rosenthal?

  It's kind of funny. I mean, in some ways you maybe ran the Airbnb playbook of exfiltrate Craigslist.

• 1:00:37Speaker 02

  Yeah.

• 1:00:38David Rosenthal?

  You did for this segment of Hacker News.

• 1:00:41Speaker 02

  My buddy Greg Eisenberg has this whole idea of like unbundling Craigslist, unbundling Reddit, unbundling Hacker News. It's a huge community. There's all sorts of sub discussions happening in there that happen regularly.

• 1:00:50David Rosenthal?

  Totally. There's a, it's a pretty big tent.

• 1:00:52Speaker 02

  Exactly.

• 1:00:53David Rosenthal?

  So you build the site. What's 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.

• 1:01:15Speaker 02

  Totally. 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 addicted. Like I'll sit down and just like press T on my keyboard and like blackout 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

• 1:01:59Speaker 02

  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 like 10 grand a month from like their travel startup. And 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

• 1:02:42Speaker 02

  more glances of 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.

• 1:02:51David Rosenthal?

  You gotta have some reason that like you're gonna show up for people. Like, well, 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 I'm pretty sure we've gotten a lot.

• 1:03:22Ben Gilbert?

  Right, we got at the top of an accidental feed.

• 1:03:26David Rosenthal?

  Yeah.

• 1:03:26Speaker 02

  Yeah, it's a hard won 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 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.

• 1:03:57David Rosenthal?

  Well, it's like, and you run into it.

• 1:03:58Speaker 02

  Yeah, and run into it.

• 1:03:59David Rosenthal?

  And run, and it's not just run into it once, it's like run into it like several times.

• 1:04:03Speaker 02

  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.

• 1:04:29Ben Gilbert?

  Okay, so we've talked about like 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?

• 1:04:43Speaker 02

  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 $5 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 was like a wake up call. Like, oh, I can like make money from sponsors.

• 1:05:26Speaker 02

  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 grown to like 10 or 15,000 people on saying, hey, like, you know, here's the email

• 1:06:11Speaker 02

  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

• 1:06:17David Rosenthal?

  Yeah, literally, it's the billboard that you see with the like, your ad could be here.

• 1:06:21Speaker 02

  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 indie hackers were like some of the worst possible customers to buy ads because like these are very fledgling startups. Like, these are people who decided to start something because they read about it on indie hackers like two months ago. And if they were going to spend like 500,000 dollars on an ad, like that ad had better work. Like, that's not, that's like their whole yearly ad budget. And so

• 1:06:54David Rosenthal?

  It's almost like you would want a company that is selling tools to people.

• 1:06:59Speaker 02

  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 at 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 wanna like figures, but I'm like, I want my shit to be good.

• 1:07:30Ben Gilbert?

  Get some warmups in first.

• 1:07:31Speaker 02

  Yeah, I need some warmups, you know? And so I Don't warm up on Broadway. Exactly. You don't wanna like embarrass yourself in front of everybody. So I got some warmups. 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 wanna talk about their kids, talk about their vacations, and they'd 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.

• 1:08:09Ben Gilbert?

  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 gonna 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 gonna be so much easier.

• 1:08:30Speaker 02

  And I think that applies to even coming up with startup ideas and trying to figure out a business model. Like, it's kinda counterintuitive. Like, people repeat this mantra, like, you know, solve an unsolved problem. And it's almost like you wanna do the opposite. Like, you wanna look at problems that people are already paying a lot of money to have solved and kinda 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 kinda 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.

• 1:09:12Speaker 02

  And within like a year of starting her company, she grew her revenue to like a hundred grand a quarter. She was living like a great life. She made it look easy, her first time out of the gate, in part because like she picked a problem where like people had budgets.

• 1:09:24Ben Gilbert?

  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.

• 1:09:47Speaker 02

  Yeah. And education is hard and it's risky because you might educate somebody and then lose because someone else comes along and wins.

• 1:09:53David Rosenthal?

  Yeah. Or more frequently, you educate somebody and they're like, eh, I've got these other things that like I need to solve.

• 1:10:01Ben Gilbert?

  All right. So Broadway comes.

• 1:10:03David Rosenthal?

  Then you get a particular email.

• 1:10:05Speaker 02

  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 indie hackers are 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,

• 1:10:22David Rosenthal?

  So none of the other companies you'd worked on, you'd gotten to this point where it's like, revenue is covering my personal expenses.

• 1:10:28Speaker 02

  And it was better in like, literally every single way. Like, I eventually, 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 100% 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 was maybe halfway down.

• 1:11:06David Rosenthal?

  You went in the same batch? Like, you didn't know them?

• 1:11:08Speaker 02

  Like, I think during the Stripe beta, I'd like, maybe like gone in their like little Stripe chat room and like, you know, pointed out some bugs and asked some questions. But like, I'd never really talked to the founders outside of that. 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? 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,

• 1:11:34David Rosenthal?

  Getting trolled.

• 1:11:35Speaker 02

  Yeah, I'm definitely getting trolled. But I read it and it was real. And he was just kind of like, hey, Cortland, 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 it to my brother, sent it to my friends.

• 1:11:51Ben Gilbert?

  It's the Paul Graham email all over again.

• 1:11:52Speaker 02

  Yeah, yeah, it was like the coolest thing ever. And we ended up meeting and talking and kind of feeling each other out at brunch the next Saturday. And over the course of a month, like worked out kind of a deal and I joined Stripe in April 2017.

• 1:12:06Ben Gilbert?

  All right, listeners. Now is a great time to talk about a new partner of ours here on Acquired, Logora, the agentic operating system that is redefining how the world's best legal teams work.

• 1:12:19David Rosenthal?

  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. Logora took that insight and asked the question, what if you really built something with that power from the ground up for the legal industry?

• 1:12:36Ben Gilbert?

  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.

• 1:12:51David Rosenthal?

  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. Logora'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.

• 1:13:15Ben Gilbert?

  And they recently launched Logora 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.

• 1:13:34David Rosenthal?

  And Logora works where you already work. You can use it within Microsoft Word while redlining or drafting. The early Logora numbers essentially speak for themselves. When they have a head-to-head pilot with their top competitor, they win 70% of the time. Logora 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.

• 1:14:04Ben Gilbert?

  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/acquired and just 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?

• 1:14:49Ben Gilbert?

  And then you were the pick? Or was it like, hey, wow, that guy's really got something cool?

• 1:14:54Speaker 02

  I think it's a combination of both. It's been funny, like, looking at 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 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 Indie Hackers have been on that list for many years. You know, like, what if we have like a community for early-stage startup founders?

• 1:15:37Speaker 02

  Just because we're a company like Stripe that wins like a lot of business from early startups, like these startups grow. And 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 Indie 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

• 1:16:20Speaker 02

  a lot of decisions at the company that like are, you know, have that in mind, like to do best by people. And so Indie Hackers was like also a huge check in that. Direction where like people just really liked indie 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 to 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.

• 1:16:55Ben Gilbert?

  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, would I sell this? Should I sell this? Like, how did you think about some of the trade offs and tensions there?

• 1:17:07Speaker 02

  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 indie 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, 10s 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 going to have me working on? You know, how much say are they going to 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

• 1:17:49Speaker 02

  going to be aligned? I wanted to know, because that's kind of like for the betterment of the community, like, the people at indie 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 indie hackers did. 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 indie hackers 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, how does it compare?

• 1:18:20David Rosenthal?

  The whole point of indie hackers, right, is like,

• 1:18:22Speaker 02

  Exactly.

• 1:18:22David Rosenthal?

  Yeah, this is kind of like,

• 1:18:23Speaker 02

  If I'm going to no longer be sort of like technically indie, you know, like, what is the trade off I'm making? And like, how indie will I be? I have this whole point that I make 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. 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 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 of the exact same job title as you.

• 1:19:05Speaker 02

  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?

• 1:19:30David Rosenthal?

  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 gotta do this thing, like.

• 1:19:50Speaker 02

  And 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 it's kind of easier to wait for somebody else to do it than it is to like pick a random employee and be like, good luck, you know, you're going to be able to do it.

• 1:20:18David Rosenthal?

  We're going to make you a star.

• 1:20:19Speaker 02

  Good luck, you're going to be able to do it. I mean, some people can do it, but like, that's not why people typically apply to jobs. Cause 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 indie hackers and Stripe, it's kind of like. Indie hackers doesn't really capture a lot of the value that it creates.

• 1:21:03Speaker 02

  You know, if people start companies and their companies succeed because of indie hackers or because of a story they heard, or 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 exist that can capture that value, including Stripe. Because if Stripe is the best product on the market, like, what are they gonna use for their new companies? They're gonna use Stripe. And so Patrick, like, really just trusted, like, hey, we think that you can make indie 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 it's contributed and sort of added went to our sales, but, like, that's fine.

• 1:21:35Ben Gilbert?

  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?

• 1:22:06Speaker 02

  Yeah. These are tricky questions, and I never feel like the most qualified to answer acquisition questions. Like, people, even though this is acquired, people call me all the time, like, hey, I'm going through an acquisition, you went through one, like, what happened with you? And I'm like, it's so specific to my situation. I had no employees. Yeah, I was like a solo founder with no employees, like, I hadn't even incorporated. But like, there's some, like, little tricks and things that helped me. So, 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 gonna 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

• 1:22:49Speaker 02

  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 indie hackers is worth? Like, what am I gonna 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, et cetera, very ethical, et cetera. And like, I think you need that level of trust because like in a contract, as I soon found out,

• 1:23:30Speaker 02

  like, there's just so many random 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, her name was Metal, 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. And ways were like, because I had a lot of trust, perhaps naively, like I just would have been like, ah, it's fine. Like they have like the best intentions here.

• 1:24:16Speaker 02

  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 their 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.

• 1:24:33David Rosenthal?

  Yeah. Well, the thing about these situations like this is like,

• 1:24:40David Rosenthal?

  the documents and the clauses and all 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 don't ever want to look at them.

• 1:24:52Speaker 02

  Yeah.

• 1:24:53David Rosenthal?

  But if you have to look at them, you know, what is written in those documents is what is gonna happen. So.

• 1:25:00Speaker 02

  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 at 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 do engineers at Stripe 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 indie hackers. So I got a lot of numbers. I was like, okay, like this is what I want. And I was like, I tried 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 best? What period is it best? Like, how long? I had a refresh as well, like all sorts of different things that I think if you're kind of like a typical employee, you might not consider.

• 1:25:45Speaker 02

  But if we're coming in through an acquisition, like the sky's the limit, like you can ask for or demand like literally whatever you want and put it in a contract. It'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. We're like, you know, talking about all these little details that we hadn't even considered, you know?

• 1:26:05Ben Gilbert?

  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?

• 1:26:26Speaker 02

  I don't know how much I'm legally allowed to say.

• 1:26:28Ben Gilbert?

  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?

• 1:26:36Speaker 02

  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 than 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. You know, if it's like, if it's Groupon and like, I don't know, you know, maybe you want the cash. And like, this is like an exercise that.

• 1:27:10David Rosenthal?

  Well, this is the difference, I think, between, you know, like Salesforce buys 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.

• 1:27:22Speaker 02

  It's literally you. And I think they're, 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 off. 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 Salesforce buys Slack, like, what does that mean for Stuart Butterfield? Like, perhaps he could say, like, I want more money if we hit these extra targets, et cetera. And perhaps Mark Benioff 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 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,

• 1:28:03Speaker 02

  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, $8,000 a month by the time Stripe acquired the company. Whereas like today, I feel much more like a high growth 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, almost to this, like the exact opposite of what like the stereotypical indie hacker company is trying to do.

• 1:28:47Ben Gilbert?

  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?

• 1:29:18Speaker 02

  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 going to listen to this podcast and be like, clearly Corlin 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.

• 1:30:00Speaker 02

  And I'm like, I said fucking like a dozen of these emails. 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 both worlds. Whereas I think if like I, started some Stripe product internally, like Stripe Press, like that has Stripe's 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

• 1:30:43Speaker 02

  languages. And 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 renovations 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-

• 1:31:07David Rosenthal?

  YouTube's a great example, right? Like when Google bought YouTube, there was still like the Viacom lawsuit was going on. Like there was all sorts of, you know, people were up in arms. There's crazy stuff happening. Maybe say there's still this crazy stuff happening on YouTube all the time. Now it's like-

• 1:31:22Ben Gilbert?

  Google Video was a failing product. Like it was trying to do the exact same thing, but was going through Google's standard process.

• 1:31:27David Rosenthal?

  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.

• 1:31:35Speaker 02

  You can take bigger risks through an acquisition, especially of like an established brand on its own.

• 1:31:40Ben Gilbert?

  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 indie hackers? What have you built to do any integrations if you have?

• 1:31:56Speaker 02

  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 where we met like twice. Years where 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 of 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.

• 1:32:37Speaker 02

  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 to the world is like, does not come from me.

• 1:32:55Ben Gilbert?

  You did it. You shifted from media company to software product.

• 1:32:58Speaker 02

  Exactly. Which I always wanted to do, but it took, Jesus, did it take a long time? 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 homepage. If you go to indiehackers.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.

• 1:33:21David Rosenthal?

  The company profiles you create through interviews and that people create themselves, they're all mixed together.

• 1:33:26Speaker 02

  Yeah, yeah, kind of. And I've been trying to like consolidate things. They're not quite consolidated yet. So there is 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, 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, which is 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 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, et cetera. 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.

• 1:34:10Speaker 02

  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 IndieHackers 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, you know, based on the numbers, IndieHackers 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 IndieHackers? 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.

• 1:34:54Speaker 02

  And one of them is, you know, would you have started your company if not for IndieHackers? 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% 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 IndieHackers. 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. That's a lot of companies. It's 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.

• 1:35:36Ben Gilbert?

  And what was that 140,000 user number when you were acquired?

• 1:35:43Ben Gilbert?

  Ish.

• 1:35:43Speaker 02

  Let me look it up.

• 1:35:46Ben Gilbert?

  I'm also curious, 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?

• 1:35:58Speaker 02

  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 that Stripe is pretty damn good as a product. Comes up on the community forum all the time. I think it was the most referenced company and all of the interviews that I did even before joining Stripe.

• 1:36:16David Rosenthal?

  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.

• 1:36:25Speaker 02

  Yeah.

• 1:36:26David Rosenthal?

  Like, I don't even know if there is another alternative.

• 1:36:28Speaker 02

  It's, it's a really good product.

• 1:36:31Ben Gilbert?

  Yes, David, there are alternatives. It is also a very, very, very good product.

• 1:36:36David Rosenthal?

  So for me to, alternative's worth using. Let's put it that way.

• 1:36:39Speaker 02

  So for me to answer your question on exactly how many users there were when I joined Stripe, I have to run like kind of a query. It'll probably take me like a couple of minutes. So like, is it worth it?

• 1:36:47Ben Gilbert?

  On air sequel writing? Well, do you have any mental ballpark of like on the order of a thousand, 10,000?

• 1:36:55Speaker 02

  It was on the order of like certainly fewer than 5,000, probably more than a few hundred.

• 1:37:01Ben Gilbert?

  All right. That helps us understand, I think, the, the scale and it's been what, three and a half years?

• 1:37:08Speaker 02

  Yeah, it's been three and a half years. I joined in April 2017. So indie hackers have been at Stripe for much, much longer than it existed before Stripe.

• 1:37:16Ben Gilbert?

  That's really cool.

• 1:37:17David Rosenthal?

  Even just like super ballpark numbers, let's say 100,000 companies added since the Stripe acquisition, 15 to 20% 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.

• 1:37:40Ben Gilbert?

  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 then we've done a lot of playbook as well, but we can specifically call that out. You know, if Stripe hadn't acquired IndieHackers, it's not like all the companies that have been created wouldn't have used Stripe. Like, I don't think you'd influence 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 IndieHackers and the exact same outcome happened for Stripe.

• 1:38:26Speaker 02

  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. And 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 IndieHackers podcast, when they go on the forum and they see somebody who's like, like, I met a YC founder at this Stripe event a couple of years ago. And I was just kind of talking to him and he's like, yeah, I love IndieHackers. 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 onto YC and now I don't go to IndieHackers anymore. And like, that's, that's pretty, that's pretty common. Like, I meet a lot of people like that. He was just like, inspired. Like, they literally started because they just read that it was possible. And when I think about

• 1:39:10Speaker 02

  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.

• 1:39:26Ben Gilbert?

  All right. So it looked like you were, you were writing some sequel there in the background while I was pontificating. What'd you come up with?

• 1:39:32Speaker 02

  So we've got, we had exactly 1,403 users on the day that we got acquired by Stripe. So we're 100x bigger today.

• 1:39:41Ben Gilbert?

  Almost exactly 100x bigger.

• 1:39:43Speaker 02

  Yeah, almost exactly 100x. Which is pretty cool. It's cool to see how that, I mean, wow, that's, yeah, 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 the 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.

• 1:40:04Ben Gilbert?

  It's awesome. I mean, 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.

• 1:40:12Speaker 02

  Did you see these stats that came out last quarter about like new business creation? Where it's like, yeah, like 600,000 people a quarter in the United States were creating businesses like 10 years ago. And then last year was like 800,000 people a quarter. And this year, it's like 1.6 million people created a business or filed to start a business in like Q3 2020, which is insane.

• 1:40:33Ben Gilbert?

  Whoa.

• 1:40:33Speaker 02

  Like, so cool.

• 1:40:35Ben Gilbert?

  Like, aren't there more and more winner take all opportunities? Like, are we seeing, now we're well into playbook, but 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?

• 1:40:53Speaker 02

  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 and get started off the back of that. So like, I think as an indie hacker, you don't have to worry too much about the winner take all companies. And then we have all these like platforms, you know, YouTube, Substack, OnlyFans, arguably, 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.

• 1:41:38Speaker 02

  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 that 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 indie 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 5 million Americans a month are creating an online business.

• 1:42:12David Rosenthal?

  Yeah, that's what I was thinking on that is like, you know, you've got the platforms like say, let's load Stripe or Shopify like, 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're a business that provides us 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,

• 1:42:56David Rosenthal?

  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, business.

• 1:43:05Speaker 02

  And 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, and 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 8am, his son was gonna be awake, he's gonna 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 they're use 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.

• 1:43:49Speaker 02

  He's like, there's not gonna 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.

• 1:44:11Ben Gilbert?

  Magic of software.

• 1:44:12Speaker 02

  It's pretty crazy.

• 1:44:14David Rosenthal?

  All right, listeners, now is a great time to talk about one of our favorite companies, Statsig.

• 1:44:20Ben Gilbert?

  Yes, there is a reason why the best product teams rely on Statsig, whether they are iterating on their core product features or shipping AI-powered experiences at scale.

• 1:44:31David Rosenthal?

  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.

• 1:44:51Ben Gilbert?

  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.

• 1:45:03David Rosenthal?

  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.

• 1:45:14Ben Gilbert?

  All right, well, I'm going to start bringing us home here. Cortland, answer this question however you see fit, but how would you grade the IndieHackers acquisition by Stripe in terms of was that a good use of capital and resources for Stripe?

• 1:45:27Speaker 02

  Oh, A+. I think it's, I'm slightly biased here.

• 1:45:33Speaker 02

  Like Stripe is a company, as you may know, that has lots and lots of money. And the IndieHackers 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 IndieHackers, 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 that they aren't happy that it happened. So it's hard to imagine it having gone better.

• 1:45:59Ben Gilbert?

  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 more companies do that?

• 1:46:14Speaker 02

  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? And they go, oh, it's going to be like so much work, I have to do this, have to do that. And they don't like make these acquisitions, whereas I think at Stripe, they're very much like, no, Cortland'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 indie

• 1:46:57Speaker 02

  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-esque, 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.

• 1:47:27David Rosenthal?

  Has Stripe done any, anything else like this since you've been bought?

• 1:47:31Speaker 02

  Or? Yeah, Stripe has a magazine called Increment Magazine, 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 gets 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,

• 1:48:15Speaker 02

  I put it in a very similar category to indie 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 trusts like, okay, well, what if we put out like these books that like help people become better founders, make better decisions, or 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. Cause like we know that's how inspiration works. And like it'll increase Stripe's bottom line.

• 1:48:39Ben Gilbert?

  Yep, makes total sense. For Acquired listeners, because I know we're releasing this in both feeds, where can people find you? What should they check out first of the various indie hackers and Cortland properties?

• 1:48:51Speaker 02

  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. Check out any of the episodes. They're all pretty good. They're all different stories of founders and how they succeeded. And so I just recommend listening to a few of them and really absorbing like, you know, what is this path like? 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 who don't want to grow anymore. So check out the podcast and you can find me on Twitter at C S Allen.

• 1:49:25Ben Gilbert?

  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.

• 1:49:34David Rosenthal?

  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 indie community. Can't wait for next year.

• 1:49:50Ben Gilbert?

  See you in 2021, everyone.