Acquired - Special- Acquired x Indie Hackers

0:00They've got new M1 MacBook Air. It's the first episode we're doing on it. Nice. Nice silent recording in the background. No, what do they call it on the pro? The active cooling system. Don't call it a fan. Welcome to this special episode of acquired. The podcast about great technology companies and the stories and playbooks behind them.

0:34I'm Ben Gilbert and I'm the co-founder of Pioneer Square Labs, a start-up studio and venture capital firm in Seattle. And I'm David Rosenpill and I am an angel investor and advisor to start-ups based in San Francisco. And we are your hosts. As regular listeners know, we typically cover some of the biggest companies, those that IPO, see Airbnb and DoorDash last week, and the companies that get some of the splashiest press coverage. But today's episode is quite a bit different.

1:03In our conversation with Cortland 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 three billion internet users open the door for the nichiest of products? And importantly, what was Cortland's lived experience of starting his own string of companies that ultimately led to starting Indie Hackers?

1:31And it's acquisition by what is now the hottest private company in the world stripe. Yeah. And last one left standing after last week. No kidding. And a lot of people cannot wait for it to IPO soon enough. Yeah. That's going to be I got to imagine our biggest episode of next season. Hopefully next season. What is happening season eight season nine. We'll see David. We'll see.

1:58Well, 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 in 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 acquire.fm slash LP. All right, listeners. Now is a great time to talk about a new partner of ours here on acquired LaGora, the agentic operating system that is redefining how the world's best legal teams work.

2:45Yup, 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. Legora took that insight and asked the question, what if you really built something with that power from the ground up for the legal industry? So the founders did exactly what great founders do, operate with obsessive customer focus. They embedded inside a massive law firm.

3:12for months. They sat with the lawyers just watching how the work really gets done. And that's how you get features that customers love, like tabular review, where you drop in a folder of hundreds of contracts, and it pulls every key term into a grid a lawyer can actually work with. Lugora's bed 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.

3:41And they recently launched LaGora agent offering greater intelligence and performance. The agent lets lawyers set an objective. Then it can handle the planning and the execution and delivery of the final product. Legal teams get to maintain full control and transparency since they're still involved where judgment is required. And LaGora works where you already work. You can use it within Microsoft Word while redlining or drafting. The early LaGora numbers essentially speak for themselves when they have a head-to-head pilot with their top competitor they win 70% of the time LaGora now has over a hundred thousand lawyers on the platform from 1200 legal teams in 50 countries and crazily they went from one million to a hundred million in ARR in about 18 months truly insane numbers and that is the real test

4:33Plenty 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 logora.com slash acquired, and just tell them that Ben and David sent you. OK, now on to our crossover episode with Indie Hackers. Cortland Allen, welcome to acquired. Ben.

5:02David, thanks for having me. So great to have you here. Our pleasure. For anyone who has not listened to your voice for the many hours that I have on the IndieHackers podcast, obviously we're going to reference it lots and lots throughout the show, but go check it out. And very excited to be doing a crossover episode with you. Yeah, I'm excited to do this. People have been asking for a while for me to do an episode on myself.

5:25because 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 of my own podcast. So congratulations on being the first people to convince me. Well, look, we are the acquired podcast and you did that mega deal exit to Stripe. So how could we not? Yeah. You know, cover the acquisition of the century. This is great. It's got like all the hallmarks of it. Both of our episodes, you'll see how that goes. Well, David, who is Cortland for listeners who don't listen to Indie Hackers or haven't participated in the community?

5:55Yeah, 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.

6:12Unlike 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, ten, a hundred, a thousand times bigger than the Rockefellers and the Carnegie's could ever imagine. Cortland is all about a different philosophy out there. The Indie philosophy, and of course the company that he started and what he runs within Stripe and the website and the community and the podcast is Indie hackers. And Indie hackers, I think it's really cool. We're going to get into 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. And Indie hackers is not a big splashy go for broke story, David. I don't know. You're going to tell us. I like to think of it as the underdogs. You know, like the internet's been around for decades. And I think.

7:09The world is still kind of slowly waking up to how much it's kind of changed the game for just like regular people. Everybody's connected to everybody, and you can reach literally millions of people if you're clever enough for pretty much zero dollars. And so people are creating these very tiny niche businesses that could never have existed 20 or 30 years ago. And in some cases, not even five or 10 years ago. And I think it's becoming possible to sit down in your living room, wearing your underwear, whatever you're wearing, and just create something that's super valuable to your community and your customers.

7:37And that's really kind of fun and fulfilling and challenging for you to work on as a person and that makes you rich in the process. And I think that's pretty crazy to check all three of those boxes. So thousands of people are doing this today and the question that like I'm asking myself constantly is like, what happens on millions of people are doing this five or 10 years from now? Yeah, I think that's what's so cool is like small business entrepreneurship in the past was a great way to build wealth and do well, you know, for your family and for yourself. But With the same art, 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 or a lot bigger, a lot bigger. Not to foreshadow our sort of playbook too much, but it does remind me that, you know, in a pre-internet era, the local small business owner,

8:28was geographically constrained. And you could have a general store that sold everything, but it could only sell everything to the people in your town. And obviously, the sort of 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. So I continue, like, Cortland, from listening to your show.

8:53Every time I listen to an episode I get smacked in the face with wait that niche is that big and people find these crazy opportunities I just listened to the patio 11 episode and he was talking about bingo card creator and I'm like a bingo card creator could be a business but like These niches are so deep or so wide or however you want to describe them. If your tam is the three billion people with the internet, then every niche within that tam can be on its own big. Hey man, Starlink's coming soon. It's going to be seven billion. Exactly. If you have a business that only appeals to one in a thousand or one in a million people, you need to live in a very big city.

9:29to create a brick and mortar business that's gonna survive, but on the internet, that turns out to be millions of people who can use your underwater bingo card creation. Whatever it is that you're making, which means that pretty much everybody can figure out something really specific that no one else is doing and kind of stake their claim on the internet, which I think is super cool. I hear the real estate is cheap too though. All right, so let's get into your story. Okay, let's start way back. Before MIT, your...

9:56family and your mom specifically was an entrepreneur when you were growing up, right? So I had, I was just talking to Jason and Kyle Conniss 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're very attentive. They're very devoted. We were sort of middle class but very comfortable.

10:25And like you mentioned, my mom was an entrepreneur. She was always doing her own kind of crazy hygiene startup selling computers and stuff in the 90s. And my dad was part of like this elite team of like furniture makers. There was like nine of them. And I each had a different role. And they would make like crazy furniture for like celebrities. So he wasn't making like a ton of money, but he was doing something that he found really fun. He was like the furniture finisher. So he'd take like a you know ugly piece of wood and make it look like amazing. And I grew up like these two people in my lives. You kind of showed me that you can do pretty much whatever you want.

10:54and kind of scratch out a living. Yeah, you can do this and it'll be fine. You can have a good life, right? Yeah, exactly. You can have a good life. You're eating or missing meals. Had a bunch of other advantages too. I was an American. I was born in the late 20th century because of my mom's computer business that she ran for a year or two before it crashed. We had a computer in the internet when I was in the third grade, right after the web came out.

11:15And so, of course, I was addicted to video games and whatever I could play, but from the adult's perspective around me, they're like, oh, this is a computer whist. Whenever I've got a computer issue, Portland spends so much time on his computer, he can just swoop in and fix it. So I was doing all this IT work on the side, and of course, nobody ever paid me. That made zero dollars. Nine-year-old fixing people's computers, but I got a lot of positive encouragement, because...

11:38From my perspective, I was just playing games and fixing bugs and stuff, but from the average adults perspective in the mid-90s, they were looking at the tech boom, and they were looking at Microsoft's stock price, and the fact that Bill Gates was mega rich, and so they would sort of pay me an encouragement. They'd be like, oh yeah, you're going to be the next Bill Gates. Keep it up. What was cool about that was I got to be a little computer nerd, and also see that this...

12:00Really, like, old computer nerd was universally respected by 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 get on that path? In some ways, it's like echoes of the Tim Sweeney story and Epic Games. You know, at him starting out, first of all, it was his older brother, right? Right then, that had a computer hardware business.

12:30and so he 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. No, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no and 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 with their computer crashes or as an error like they know all the keyboard shortcuts they're good at googling stuff and if you have that kind of base layer of skills it makes everything else much easier. So your 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?

13:29Oh 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? That's 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 the 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 and like encouragement and like privilege and a way. And so yeah, by the time I left,

14:27to good college, I felt like pretty ready to take whatever the role was going to throw at me and also pretty far ahead of the curve in terms of knowing what I wanted to do. There's never a question like, what major do I want to have? What do I want to do after I graduate? Like I was always 100% certain what I wanted. And I'm sure that tragic death in the family also forces a lot of early maturity that you have to take on sort of more responsibility or at least think about the broader context around your life than just yourself earlier than you otherwise would have. Totally.

14:56And I think for me, the biggest impact was just like, you kind of get like a floor. You establish like, okay, this is the worst thing that's ever happened to me. And like I survived it. You know, like it was terrible and like all sorts of like bad side effects you wouldn't even think about. But like once you establish a floor, then like a lot of other things just don't look that scary. Like they don't look like that big of a deal. Like, okay, what if I start a company that fails? Like, oh no, you know, like, I'll go get a job. Like, no one died right now. So I think that's kind of what I got out of it.

15:22I assumed that the computer, the level of a computer is knowing what you wanted to do, getting out of the Kenny G phase. That's what probably never happened. The Kenny G phase was a good one to escape. Yeah, so I remember like really wanting to go to MIT. I somehow figured out that that was like kind of the best school you could go to if you wanted to be a computer scientist. I had no idea that Stanford even existed. Like if I had known that and that it was in the Heart of Silicon Valley, I probably would have tried to go there.

15:46And I also didn't know that it was even feasible to just not go to college. If I had known that I could do that, I probably would have just done that and tried to start some stuff. But I remember talking to my mom and asking, okay, how do you get into MIT? And she's like, well, good, good grades, and study, and apply, and hopefully we'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, how frightening that was, I got one shot to do the thing that I wanted to do. And if I got rejected, that I would just be done.

16:11and a lot of ways like that was a much scarier thing than I think starting companies that like have the risk of failure because like you can start a company a million times like if it fails like there's no like all right you know that's it you know somewhere else now like you can just keep doing it over and over again well how many companies have you started now seven and yeah I guess it's my seventh attempt to do something that worked and the only one that really really worked so yeah I was gonna say so when you get to MIT you I think if I understand the history you start applying to I see like

16:41Regular. Yeah, I played a lot of times. So is this like a like every quarter thing? It's like register for classes, put in the YC app. Well, I was like a pretty bad student. I didn't understand like the idea of like, I just didn't really want to learn. And I thought all the stuff I was learning in my CS classes was boring. And so I spent a lot of time working on my own side projects. And at some point I discovered that there's this magical entity out there that will like give you a bunch of money to take your projects 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.

17:10I had Dropbox already gone through YC at this point. At some point during when I was in college, Dropbox went through. And Dropbox was also an MIT startup. So everybody on campus had a bunch of free Dropbox codes, and we had a ton of free space, and everybody knew their story. So there's a lot of positive encouragement there as well. You want to apply to YC? Everybody knows what that is, and thinks it's cool to just apply, even if you get rejected. I got rejected once, and I got an email from Paul Graham, where he was like, oh, I think you could have done this better.

17:36I remember just showing that email to my friends, like, so proud, like, look, PG responded to me. This is just a rejection. Basically, that's what were some of the ideas you were applying with. So the very first one was this company called F-Mail, which did for, like, get this Gmail for Facebook. Facebook released their platform sometime when I was, I think, a junior. And at that point, like, I'd never really built a web app.

18:00But a buddy of mine was like super encouraging. He was like, oh, this is so easy, cool. And just go learn PHP. And I'm like, PHP, like, what is that? So I went online and I started learning it. And he's like, look, I'm like, well, how do I extort user and make a Facebook was all PHP? Yeah, yeah, it was all PHP. And I just kept asking, like, oh, how do I do this? He's like, oh, just go learn like SQL. And like after a semester, I learned all this different stuff. And I've been able to build this app from scratch. And I thought it was amazing. Like, oh, I didn't know anything about this stuff. And now I can like make my own web app. And I applied for YC.

18:27And 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 looking for stuff to write about, a bunch of these small tech...

18:37Publications just like wrote about it like oh crazy MIT genius figures out a way to put a Gmail inside of Facebook Like we'd scanned it to like look like Facebook and it barely even worked it was like super crappy But I was like wow, it's like really easy to get like depressed to write about you and like you can do a really simple thing that takes you a semester Even if you're a total beginner and if like it's kind of creative and kind of unique and people haven't seen it before like you'll get attention So that was like a kind of a good experience even though I got rejected And that was an era to 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 years was FMAL. 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 my sequel to be able to like store the stuff in a database and I mean that

19:32That's what everybody did that. And that's even what Facebook was written in, David, as you mentioned, and the web was like, it felt like a small place. Yeah, it really did. And I think to some degree, like it always kind of feels like that in hindsight. You know, I think like 10 years from now people will look back and be like, oh, like the quaint times of 2020, when you could do, when you could do anything, and it would get attention, you know? And like to some degree, like that's true. Like if you spend like very few people have the time to sit down and just like think creatively about ideas.

19:59And one of the easiest ways you want to come up with any creative idea is just to take two or three things and combine them. Because once you do these combinations, you instantly start getting to ranges where no one has ever done that before. If you type the dog into Google, you're going to get 10 billion results. But if you talk the dog left, you're going to get a million results. And if you type the dog left the store with a bone, there's going to be no results. There would be a sentence that no one has ever said before in the history of the world. And the same thing is true with ideas. So I think there's always this.

20:28sort of framework you can use to come up with interesting ideas and like we both found kind of the same one you know like let's take this one thing and put it inside this other and like that was enough to stand out and I think that's still true today yeah okay so you mentioned hacker news which I assume is going to continue to play a big role in this story here. What were you hanging out on hack and news while you're at MIT doing all these YC applications? So back in the day, Paul Graham used to write on his blog all the time about startups and all sorts of different stories. And he was very motivational, inspirational, and positive. And then he had this website he created.

21:00which again, he just seemed like it was very half-hazard. He's like, what if I had a little reddit clone? And of course, it's now millions and millions of visitors or whatever. But if you wanted to apply to YC, you had to be on Hacker News. Yeah, Ben, you know the story, right? It exists because he was dissatisfied with our programming and was asking Alexis to make that better. Alexis and Steve, I think it was either to make it better or maybe to invent it at all because that subreddit didn't exist yet and got frustrated with their slowness and started Hacker News.

21:29Yeah, that's hilarious. So he's like, yeah, this is not good enough even though he's an investor and read it 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 NYC. And like not only did you want to have a Hacker News account, but you wanted to have like a history of like smart like intelligent thoughtful comments because you know Paul Graham and the partners are going to look at what you had posted. So if I look at like my YC account right now, I think it's yeah, created October 8th, 2008.

21:56So I was on YC way back in the day, reading everything, digesting everything, and then trying to leave smart comments that I would be probably embarrassed to go back and look at right now. It's so funny to think about now. Got how many companies, like 300 companies to go through YC-ish about every year. But it was this little corner in community.

22:15I mean, it still is a community, a very large community now in a certain sense, but I mean, I remember being a YC fan first and foremost and using the products like I was proud to be a Dropbox user and abandoned my flash drive because it was a YC company. I suppose that that is even actually a bigger effect today, but it felt at some point like a club. I remember I think it was like senior year in my high school that I felt like I was in some sort of club for even knowing what it was.

22:39Yeah, I kind of had that feeling. And then, like, I eventually ended up doing YC, and I remember, like, distinctly, 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, he's got PG's house. And now, like, it's just this huge and personal thing. 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. Yeah. So, catch us up there. So, what idea did you end up going through YC with? Yeah, so...

23:09And college I ended up meeting up with these two grad students who had this cool idea for this new version of email, and then we tried working on it, and it was pretty cool actually. We got a lot of press, we got a lot of attention, but we didn't charge any money for it. And so after a year of working on that, we ran out of money. We had won some business plan competition, and it was 25K, so I just lived frugally on that for a year, and downtown Boston ran out of money, and I decided I was going to move to SF, and somehow get into YC.

23:37So 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 request for startups, that he would publish. And one of the ideas on there was like kind of related to what I'd already been doing. You know, this whole thesis that like, you know, the email inbox is this like unexploited, you know, domain, and you could have a Trojan horse where you get in there with like some sort of productivity app or something, and then once you get all of the email users off Gmail, like you convert them to your own thing.

24:03And so that was his obsession, like these clever tricks you could use to get a ton of people on your apps. And so I was like, okay, let's just do that. So I met another guy, again, on Hacker News, who had kind of posted, like, hey, I'm looking for a co-founder. Okay, yeah, I was going to sign up. You made your co-founder on Hacker News, right? Yeah, one of my previous competitors in 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 the 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 click. 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 did we get the money? So I can pay my rent this month. Was this what was this? What was it? We did when are 2011 for YC? So this was like in the fall of 2010, like November. This was.

24:55Before the Yuri Milner S.V. Angel deal where you got that happened during our batch that was like the like we are the very first catch for that I remember the the previous YC batch was super jealous because they only got like you know like a 17 K or whatever and so that's what we got it first was like 17 K divided by two me and my co-founder like you know we had like enough for the two of us we ended up moving into this rent controlled apartment and SF and just eating like a lot of like oatmeal and crackers and stuff and then I remember like one day during YC they kind of called us down like on a like a Friday or like

25:24some off day. Like, hey, it's very important everybody come down. And we went down to the YC headquarters and they had like those telepresence robots kind of like walking around, like sort of like a camera, like a screen on wheels. And there's like your email and there's face on it, like this Russian oligarch billionaire, like walking around talking to everybody and like we've got an announcement. And I was like, yeah, we're gonna give everybody like $140,000 of additional money, sort of no strings attached.

25:47as 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 I don't have to worry about where my man's gonna come from. So we structurally understand that. Was that a convertible note that they invested on with that? I couldn't tell you. I can't really remember. I think it probably was a convertible note. And this is before they had like, I mean, this is before they had the safe. I think the safe came around like two or three years later. But it wasn't like literally free money. No, it wasn't literally free money. Like there were strings attached, but I

26:17I think it was uncapped to them. There was a really good deal and none of us questioned it. Like we just signed the papers. So at this point, you're getting like, probably feels like a huge amount of money in funding, right? Like, you know what I mean? Customers, right? Nobody's telling you. No, we're 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...

26:39I think we hadn't built yet. So, the idea we were working on was called Task Force. The idea was, you get all these tasks in your inbox. You know, like, I've got Ben and David from required, like saying, hey, Coral, and if you prepped for the podcast yet, right? And, 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 had it a due day, 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 take over the inbox, and everybody would have it. And eventually we did launch NYC, and we got a decent number of users. By the end of NYC, I think we had 100,000 users. But back in the day, that was nothing. The social network had just come out a few months earlier. A million dollars isn't cool. A billion dollars isn't cool. But that was kind of the mantra. And no one cared that your app had 100,000 users. That was meaningless.

27:30I'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 you 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. Yeah, I think it's still there. Like if you know the right, combination of keyboard shortcuts, like you can get a little task, you could 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 organize my tasks into like a little list of check boxes.

28:14And 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 will do an email. There was like the combination and like that's exactly what the press wrote about like, okay, you've seen a task list. You may have seen a task list in email, but if you've seen one in Gmail, people were like, no, I haven't. Maybe I should sign up. So we kind of combine those things and we got to demo day NYC, like the very end of YC and we like presented and investors just like they weren't interested.

28:40They're like, yeah, you've had okay growth, but where is this really going? And we've invested in email startups in the past, and they're all dead. What's gonna make yours different? And we didn't have a good answer to that. So we went into the summer after YC with probably still 120, 130K of this money in the bank, trying to figure out what are we gonna do with this startup that's not growing fast enough for us to raise money. Again, if we have our lower rate, one of the talks.

29:05Maybe it was like a Tuesday dinner talk while you're at my seat was Kevin Hale for Moose. So Kevin Hale was just, I thought it 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 they were dressed super suave and like it was so cool and flashy. Drive up in the Lambo. 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 PJ was like, this is an example of a stereotypical CEO. And then Kevin Hale came in from Wufu, and he was like, cool, calm and collected character. And he was just like, yeah, like we're not raising any money, you know, like we packed our bags, we moved to Florida, like we're making forms, but we're making form sexy.

29:54And 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 DCs who want to invest and we're like, nah, 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.

30:11It was still in your cohort, nobody was talking about it. There was a few companies that had some sort of revenue model, but all the companies that were celebrated were the ones that had just raised the most money. Who raised from A16Z the earliest? There's one founder in our batch who will not name who raised from A16Z the very first week of YC, and they raised millions. They are putting up Facebook growth numbers.

30:35and everybody worshiped the ground that these founders walked on. The whole, it was obnoxious to the point where it was like, I didn't want to see them. But you're kind of jealous too, because I kind of want that level of success. But at the end of the day, nobody was making money. Nobody wanted to make money. It was all about growth. And so when I heard Kevin Hale talk about how woofoo was just crushing it, I remember running up to PG and like, hey, we're not growing that much. What if we just did this? What if we charged money? And he was like, That's cool, like whatever it takes to stay alive. You know, he was very much like be the cockroach. You know, don't die. You need to make money to survive until you pivot to a better idea. That's what you should do. But like that sort of asterisk was always there. Like what you then do is pivot to a better idea that, you know, can make you a billion dollar unicorn because like who wants to just make a few million dollars a year? It's so funny. It always reminds me that incentives drive behavior and

31:25If you think about YC's incentive here, do you think back on it and say, well, gosh, they sort of, for their portfolio construction, they needed us to be a billion dollar company, or at that point would YC have been happy with a bunch of court lends building profitable businesses. When you interview, they really want to know that you have a shot.

31:43At becoming a billion dollars because that's how the mechanics is 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 bachelors over It was kind of clear that like a few people had given up and they don't really gonna make it and like especially in the summer after a bachelors 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 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 we're happy that you're here. And I think after that, they're less adamant that you gotta go for billing. You gotta go for billing, you gotta be at unicorn, they're like, do whatever it takes to survive and get to the next stage. And a lot of respects, that's the hallmark of being a good entrepreneur. How can you take one small success and parlay that into something bigger? And eventually maybe you get another shot at going for the unicorn company.

32:33I think in the beginning they're very focused on us being big. There's also two questions about how this gets big, which are easy to answer because it was like PG's idea that we were working on. But later on, I was like, how do you not die? How do you not die?

32:43Yeah, 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?

33:10No, I completely agree. I think if you're creative enough and you think about it enough, you could figure out a way to your next hill. Like, Andy Hackers today is, to my knowledge, the biggest online community of startup founders. Andy Hackers in its first month was a blog. There's a lot of blogs out there. You started off with a very tiny hill and I made the blog as big as I think.

33:29I wanted to, maybe it could have been bigger, but it was pretty big. But there's always some way where you can say, okay, now I have this advantage that I didn't have last week or last month or last year. What ways can I use this advantage to parachute over to that slightly bigger hill? Maybe you lose 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 a staircase. A lot of people will want to jump to the top of a staircase. It's very hard to jump to the top of a staircase. Very few people are capable of that feat, but it's pretty easy to walk up a staircase one step at a time.

33:58And so I think a lot of being a founder is just figuring out how you can go one step at a time. Even if you have some grand ambition, how you can start like super small and then kind of work your way there. I love that. And without jumping too far ahead to indie hackers, it just reminds me the threads of your ability to be a community builder and a participant and online community sort of starts with meeting your co-founders on hacker news and being an obsessed participant with that. And like you said, today you run, how do you describe it, the largest online community of startup founders? Start up founders. That's cool.

34:28I mean, they're indie hackers. They don't mostly have billion dollar ambitions. They're the underdogs. But a lot of them, I think, once they get started, realize, oh wow, I'm making some side income. And then a few months later, oh wow, I can quit my job. And then at some point, you're making a lot of money and you're thinking, what do I want to do? Do I want to retire to a beach somewhere? Or maybe what I want to do is build something even bigger. So a lot of indie hackers I talk to are no longer even indie hackers. They've raised money. They're building bigger companies, and that's where their life path is.

34:57took them. Well, that's what I think is so cool about this. Like, unless you 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 sometimes they become indie hackers and sometimes they become just a business that makes you a couple hundred thousand a year. Yeah. Exactly. Like I don't.

35:25like to juxtapose indie hackers as a counterargument to raising money so much as a counterargument to having a boss and working a desk job and wondering what if for the rest of your life. Being an indie hacker is really about the idea that 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 time freedom, so you can work whatever hours and schedule you want. And so being an indie hacker is really this confidence in yourself that you can create something that That'll make your life better, really, and make other people's lives better in the process, and give you that freedom, and maybe that looks like raising a ton of money in the future. Not to mention, it is the ultimate option value preserving activity, where, you know, if you start by saying growth at all costs don't make any money, we're going to raise venture dollars. You're on a path. You're on a very specific path. If you say, I'm going to build something profitable that funds itself, you got all the option value in the world to continue to take it whatever sort of trajectory you want to.

36:22Yeah, exactly. And the kinds of companies that I've seen people build, I almost feel like we need a new word. Because you think about business that has all these connotations. You imagine a bunch of men and suits in a boardroom or something, reading graphs. And then the word startup is not quite right, it's closer. You think about tech and technology and it's like internet-enabled. Like they're wearing T-shirts instead of seats. Yeah, but they're doing the same thing. Yeah, exactly. They need to be some, I don't know what it would be, some third word. I'm just looking at people I interviewed this founder Sam Meaton on the podcast earlier this year, and his sister at some point was like, I want to sell cookies.

36:57And he's like this software engineer who's worked in growth roles at Airbnb, and he's 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 DoorDaps, like they have their own delivery drivers, their own sort of internal mechanism, his sister's like the head of cookie R&D. And they're making like 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%

37:27margins too. They live in a really good life. It's not just your traditional idea of a business. He's trying to make his community better, trying to make his life better, and he's not stressing over how fast can we grow and how much bigger can we make this. He's thinking about what do I like to spend my time doing? At the same time, he's getting rich and making everybody feel great. I think this is such a big movement alongside the traditional startup race venture capital like be something big right off the bat because like the economic You know generation activity generated by this class of entrepreneurs is probably in aggregate going to be equal if not larger than like the Rockefellers of the world

38:11Did you guys watch that series, Chernobyl? I was on HBO last year. Oh, it was so good. Great series. Oh, no, I heard about it. It was freaky. They timed it right after Game of Thrones went off the air. They're like, boom, here's another series. Don't don't subscribe from HBO, but the kind of boiled down the entire story, like the work of this one scientist. And it was an amazing story, it was great. But 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 new clue disaster. And the reason why they did that is because it's just easier

38:41to tell a story about one person. And it's the same in business. It's easier to tell the story of one company. We're all fascinated by how big Apple is and the impact that Apple has. McDonald's is crazy. They have 20,000 restaurants in the United States. That's the easy story to understand and to tell, but I think the much more impactful story is there are 600,000 individuals who have restaurants in the United States. That's way more impactful than McDonald's having 20,000 restaurants, but it's a harder story to wrangle. It's a harder story to tell and to connect the dots.

39:10And I think the way I look at what I'm doing with Andy Hackers is I'm trying to like connect the dots of all these really tiny tech businesses that are never gonna make the news. You know, they're not, you know, Amazon, they don't have a $2 trillion market cap, but like what happens when like a million people are building businesses and make millions of dollars online? You know, what does that look like? When this comes out, we will likely have just done the DoorDash and the Airbnb IPO episodes. There is a narrow set of Practitioners whether you're founder or an employee who can learn from the tactics and the playbooks accomplished with DoorDash and Airbnb But based on all the media coverage that those are the stories that get told because that's the simplest and most interesting narrative But if you're looking to actually learn like let's say indie hackers continues to

39:56grow and expand and you figure out more ways to parallelize it. And at some point there's, you know, a hundred thousand stories of businesses and the playbooks that they ran on your website. Like someone can find an incredibly narrowly applicable business that's just three years ahead of them and run their playbook on their own business in a way that is far more useful than the one story that everyone focuses attention on. Yeah, exactly. That's kind of the goal of like a lot of the things that I'm building on Indie Hackers. How do you see these companies very early days? And then how do you filter down to a very specific niche so you find the company that most matches the profile of what you're trying to build?

40:36And so we have this directory that I kind of have casually built two and a half years ago. And I was like, oh, we should have a directory products. And I haven't touched the code two and a half years. But when I built it, it was like, OK, 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 a little timeline where they're like saying, OK, here's where I launched. And here's what I thought about my launch. And I thought I was being ridiculous saying 100,000, but it shouldn't be long. No, it shouldn't be long. And I think it's just the resource that needs to exist. You need to be able to go out and see how other people are doing it because

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42:58I'm gonna do David's job here. So take us from the light bulb of task force should be making money to the founding of Indie hackers. How did that period of time happen? Yeah, 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. Were they in your batch? Or were they were before you, right? They were before I was, like maybe by year or two. They took a while before they got their product to the point where it was ready.

43:28Understandably because there's like a lot of regulation with banks and stuff but they kind of launched into beta and we got like a good first look because we were you know 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 three thousand dollars 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

43:56And so, of course, we went to the YC partners, we were like, hey, look at this, this is cool. We're making a few thousand dollars. And they're like, yeah, but what if you were making way more than a different idea that wasn't a tiny Chrome extension? Which in some ways is good and bad. And 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 that we should never do. We just completely started over from scratch with an idea that we thought was bigger and better. And we sort of violated that principle of taking it one step at a time. And so probably over the next six or seven years,

44:25I started five or six different companies. Each one got to a point where it made a few thousand dollars in revenue, but it was never really a big deal. It was never the success that I really wanted. I think this is kind of an important thing that I realized. The first couple of years, I was just paddled in the metal on my computer every day, coding as much as I possibly could. This is going to be it. I'm going to succeed. This is going to be it. It has to work. It never did. Not only did I not succeed, but I also wasted a bunch of time.

44:55not living a very fun and productive life. Like I don't even remember like one or two of those years in my lives because I was like literally just doing the same thing every single day. And now my model that I have for it kind of framework in the way I think of it and the way I wish I had thought of it then was that everybody's kind of got like a certain number of companies that you need to start before you succeed. For some people who are exceptionally talented or lucky or both, like that's just one. They're gonna succeed right out of the gate. Some people maybe it's like 35. For me it was like seven and

45:23Really all you need to do is just to make sure that you don't quit before you get to that number. That's really the entire name of the game. Just don't quit before you get to the number where you succeed. So you should just structure your life to make it so it's easy for you not to quit and to make it so that the journey itself is actually pretty fun and you're learning a lot along the way because you're not just building a startup in a vacuum. You're meeting people and you're picking up new skills and you're learning new things. The startup is the journey is as important as the destination at the end of the day.

45:52And so now days and like eventually I kind of figured it out like oh, I'm like learning so much stuff like I should make sure that I can really enjoy my life while I'm building stuff So the last few years there before I ended up starting into 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, it's gonna work. It's just gonna be the one Hmm, that's such a great lesson and just like a couple points of clarification where these all inside the same

46:19like entity or was it different co-founders or how did that sort of technically play out? Yeah, like the first one or two were kind of inside the same entity. And then my co-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, 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.

46:48Part of it was like I just didn't like the idea of having a boss. Like me working at Stripe today is the first full-time job that I've ever had. Like I just don't like to be told what to do, I guess. And part of it was like this like, I don't know this pride of like, I don't want to have to interview somewhere. Like I don't want somebody to be able to reject me. Like I want to be unrejectable. Like I don't want to ever put myself into a position where somebody could say no. And so like, okay, I just want to keep doing this myself. So I would just like survive off of kind of my income from some of these apps because I would keep them running and they would make like a few hundred dollars a month or a few thousand dollars a month. And then when I got low on income I would just go get

47:18a contract job, and then work on the side, et cetera, et cetera, and just make it so I never had to quit. And I think there's a lot said about startup failure. Maybe your ideas fail because the market was too small or because your product took too long to develop or you ran out of money. But my take on it is kind of that none of those things actually kill your company. Those are just obstacles. So your market wasn't big enough and then what? You quit? You didn't have to quit. If you imagine a startup journey, being like you walking from like you being an early pioneer walking from the East Coast to California, right? Like those are just like obstacles. There's like rivers and mountains and like you can kind of like step over those and 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 in just living Kansas. Like you want to keep going and find a way to keep going. And so for me, that was just living super frugally and figuring out a way to like start the next thing, which meant taking on contract work and building up my savings whenever I needed to. Yeah.

48:14Default alive or at one point I ran a startup weekend in Seattle and Bolu who actually I think went on to YC with this company future advisor and Sequoia funded it He gave this great talk called you're alive as long as you're not dead and he was like yeah lots of things bad things can happen at your company, but as long as you don't shut it down You have not failed. 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. Exactly. That's always stuck with me. Yeah, and even if you do quit a particular company, I've quit lots of different companies, but as long as you don't quit your overall journey, you're still on that path. You're still headed to California, and you're going to eventually get there. Who knows how many startups it's going to take, but you'll get there as long as you're learning and you persist. I think the most important thing you can do is figure out how to keep going. All right, so the genesis of indie hackers.

49:02But, Genesis, how did that happen? So, I just rolled off a contract job, and I had about a year of runway in the bank. So, it's like, okay, here we go. Take four. I'm going to figure out something to work on that's going to work this time. You know, worst case scenario, it's going to all fail. I'm going to go back to working contract jobs. And so, I started working on this one app that I called NOX. And it was kind of like this meant clone for your phone that would like buzz you with your finances. And maybe like two or three months into it, I was like, this is an endless slog.

49:30of coding 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 and hack news of people who come up with new ideas and we're already making like five or ten grand a month and like I haven't even launched my thing yet so it's like okay this is like a dud I should scrap this and go back to sort of the drawing board and figure out you know what can I like What are all the different lessons that I've learned after years of doing this? Like, let me make sure I'm systematic in how I approach this so I'm not just making the same mistakes again. Because I repeatedly made this mistake that a lot of software engineers make where we just, you know, it's been way too much time coding. And 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 and exactly

50:15three weeks. And it didn't require very much code at all. It didn't require a lot of marketing or anything. It was super, super easy. And I think this is one of the levers that a lot of founders don't realize that they can pull. Everybody's trying to figure out, how do I get enough money to work on my idea? Do I need to fundraise? Do I need to borrow money and go into credit card debt? And the other lever people pull is, how do I get more time? Maybe I'm going to work nights and weekends and all this stuff. I'm going to work at three-day work week instead of five-day work week.

50:40But I think like the third lever that's probably the best is like, how do you just start smaller? Like how do you figure out like what's an easy, even easier thing to do? And for me, my idea was kind of like, okay, I want to build kind of an indie hacker business so I can sort of, you know, pay my rent, pay my bills and then figure out what I want to do next. A ton of other people clearly want to do this. Like I see them on hacker news every day asking all these questions to people who've done it and sharing their stories. Maybe what I can do in a very meta sort of way is build a better version of these hacker news discussions.

51:08People are always talking about this, but their story's kind of suck. They're like leaving out important details. And everybody in the comments is asking them, like, well, how'd you cope with your idea or how much money are you making? And that's not necessarily in their stories. If I can compile all of the stories that I found and tell them in 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 both me and a bunch of people who are like me who are trying to figure out how to be indie hackers themselves.

51:37So that was kind of my idea. Kind of phase one. Like, I didn't have a revenue model. I didn't know where I was going to go from there. But I was like, that's a really easy place to start. All I have to do is email some people and, you know, get their information, put it on a blog and launch it. And like, I'm 100% sure people in Hacker News are going to eat it up because they've already been eating up stories like this before. And is the idea that this is going to become a business for you at this point or is the idea really like, this is a project. I have it envisioned in my head. I know the scope. I know how to build it. I think people are going to love it.

52:06but it's a project. 100% is gonna be a business. I don't know how I'm gonna make money yet, but it's 100% like at some point, I'm gonna start in this really small pool. I'm gonna 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. Maybe I'll have an audience, maybe I'll have a lot of traffic, maybe I'll have a big mailing list, and then from there, it should be easier for me to figure out how to make an actual business. The revenue aspect, maybe revenue and profit aspect of the stories you were telling. Was that super key? Because I can imagine, when you're trying to feel like, oh yeah, you're talking all this game about how great it is, all the stuff you did, but is it actually working? Give me the, that feels almost like the zest of it before Zilla, right? It's like, hey, this house looks good, but what's it worth? How is it extremely important? If I could write a startup book, I would call it Problems First, where the first thing you want to do is you want to figure out,

53:03what are the problems that your potential customers have? So you don't build some random product that doesn't solve their pain points. And when I was reading all these comments on hacker news, I was trying to find a business idea. And I didn't want to read comments from people who didn't have proof that their business idea worked. Somebody said, I've got this great company I'm working on and it's really great. It does this and this and this. And they don't share their revenue numbers. For all I know, they're making $5 a month. And it's not that great.

53:27And I could tell everybody else in the comments, kind of the same problem. They're like, hey, we only want to upvote the stories that share their revenue numbers. We only want to upvote the stories that have some sort of proof or some sort of inspirational thing that we can grasp on to to know this person is legit. Anybody can give you advice and tell you what to do, but if there's an outcome that's a result of that advice, you don't know if it's good. Don't train your model on garbage data. Exactly. And so that's a thing where there were a lot of other interview sites on the web that talked to entrepreneurs.

53:53pretty much not at the time that realized how important it was that you needed to be transparent. You needed to include revenue numbers. And so when I went out and I started emailing people and saying, hey, my name's Corlan, I'm starting this website. It's going to be called Andy Hackers. Will you tell me your company's story? And oh, by the way, I need all your revenue numbers. Half of them were just like, fuck off. Why would I give you my revenue numbers?

54:16and 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 did the same for me in the past. And so by the time I launched, I think I had gotten like 10 people to agree to share their entire story and their revenue numbers. When you launched, you built the site, right? So like, didn't go to Squarespace, didn't go to Webflow. What was the thinking behind that? Yeah. So I had a couple sort of reasons for that. Part of it was, I had a bunch of other ideas that I had come up with.

54:46and 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 here I am the software developer from building all these other startups. I learned so much stuff from building startups over the years and failing time and time again. I learned how to design and how to do front end development and back end and server admin stuff. And here I was going to sort of blog. I was like, wow, it's such a waste. I want to throw myself some kind of bone to make this fun. Because starting a company should be fun. You should enjoy the journey, not just the destination. And so I said, okay, well, I'll do a blog, but I'll allow myself to just build my custom blog from scratch, even though that's gonna add another week and a half to my large 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 stuff. So you weren't thinking, like, Stripe Revenue Connect, building a community, yeah. That was kind of in the back of my mind, the community stuff. Definitely not like the product directory and Stripe Revenue stats, so a lot of the stuff that exists today.

55:43But like, I did have kind of a strategic sort of session with myself, so I spent like one day just thinking strategy. Like, 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 have a crappy name now and I have a better name later. But like, really, like, it's hard to change your name later on.

56:05So I had been bitten by all these issues, and so I said, okay, I'm gonna take one day and make all of these semi-permanent decisions. 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 named after kind of a new class of people.

56:22Because I was like, well, there's no name for these people and these discussions. It's like really hard for them to find each other even because there's like, what are you even search for? Like, story of a person who bootstrapped, start up, and makes 5,000. There's nothing to search for. So hard to find. So I was like, I'm going to call it any hackers. I had a bunch of worse names. But any hackers are the best one I came up with. I decided I wanted to make the site blue. So it's like this very dark blue color that's probably not very accessible and kind of hard to read. But every other site and existence is just like white with black text.

56:50Everybody was writing on, you know, 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. I didn't like the platform risk. I've been kind of burned by that before building on Gmail. And, you know, they would change their API all the time and like kind of break our apps. And so I didn't want to deal with like, you know, putting up a blog on medium and having it look like every other medium blog and then medium changes their business model or something. And now I'm screwed.

57:18So those are kind of like the three decisions I made back then, and all of them I think turned out to be pretty good in the long run. And the etymology of the name, it's interesting thinking about when you started this, the notion of an indie developer was already a thing. I mean, I remember considering myself an indie developer in 2000.

57:34eight when I started working on my first iPhone app. And I think Craig Hawkenberry and a bunch of the like icon factory people, they, they were saying, oh, I'm an indie developer, indie, you know, iPhone or Apple developer. And obviously hacker news was sort of like a thing. But those communities were basically not overlapping. Like hackers were what people who were technical and wanted to start high growth technology startups refer to themselves as, but Indies were what the like lifestyle developer community, primarily centered around Apple platforms, kind of called themselves. Yeah, and I wasn't thinking about like honestly any of that Andy stuff. It wasn't even aware that they're really Andy developers. I was just like, okay, well, I want the idea of an independent programmer. Because again, it wasn't so much a rebellion against raising money. It was a rebellion against going to work for the man and making Google $10 million a year from your code, but you're only getting 200K of that. Why don't you start your own thing and be kind of your own Andy developer?

58:29and Hacker News was so called because Hacker is 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. There's really no limits. You can do whatever you want. Before we move on from this point, talk to me about platform risk because in my mind, 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 everybody.

58:55There's always some platform risk, like we've collected email addresses from one at a, 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 your end customer. So, How do you think about how far you should go on eliminating platform risk? Yeah, I think everything in business is basically a trade-off. And what you really want to do is just be aware.

59:34of the trade-offs that you're making. There are no hard and fast rules. Never build on a platform. If you build on a platform, maybe you can give you additional distribution, but then you get the risk that they might shut you down or change things, or you might lose out on the branding or the ability to differentiate yourself, et cetera. Maybe you can charge a high amount of revenue per user, but that means you're going to get fewer users in the door, fewer customers, but then also you can spend more to require costs. It's all trade-offs. For my particular situation, when I looked at that trade-off,

59:59Really, the only contender was like, okay, I can maybe try to build a big Twitter account where I share these stories. I can repeatedly post on Reddit or hacker news, or I could have a medium blog. Those were the big platforms that I considered, and every one of them I thought would give me either very limited distribution. How much did medium really help with distribution? It was kind of hit and miss, and they would also just completely destroy my ability to have any sort of branding.

1:00:23And 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 if I was going to name it in the hackers, 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 free and I'm just getting lots of users in the door, but I didn't have a business model, then 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 do my own.

1:00:47And I also had kind of my own distribution strategy. I already knew that people were going to be eating this kind of stuff up on hack anews because they already were. And I already knew that hack anews have a lot of traffic. So it's like, okay, I don't need medium. I can do it on my own. So I get no real benefit from medium and I get all this additional risk. The trade-off just wasn't worth it. It's kind of fun having it in some ways. You maybe ran the Airbnb playbook of...

1:01:11ExploTray Craigslist. Yeah. You did for this segment of Hackenews. Yeah. My buddy Greg Eisenberg, that's this whole idea of like, you know, unbundling Craigslist, unbundling Reddit, unbundling Hackenews. It's a huge community. There's all sorts of sub like discussions happening in there that happen regularly. Totally. There's a, it's a pretty big tent. Exactly. So you build the site, you want us to blog on your site. As I understand it, pretty quickly, you figured out that email was a pretty big unlock.

1:01:39kind 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 too. You can almost imagine the web is, like, a collection of, like, feeds or, like, destinations and some of them are places where people go, like, habitually. Like, I habitually check my email. I habitually check the notifications on my phone. I habitually check Twitter. I'm just, like, addicted. Like, I'll sit down and just, like, press T on my keyboard and, like, black out for a second, like, I'm on Twitter. And then there's other places where people just don't have a habit. I made Andy Hackers, no one on Earth had a habit of regularly visiting Andy Hackers. And they weren't gonna have that habit any time soon, so I was publishing once or twice a week. Twitter's got new content every single minute. So for me, it was like, okay, well, how do I hook into one of these feeds that everybody already habitually looks at? And it was a combination of both Twitter and email.

1:02:31So I made the Twitter IndieHackers account. I tried to tweet every story that I had so that you would sort of incidentally run into them when you check your Twitter and be like, oh yeah, I remember IndieHackers, I'm gonna go back there. And then email is a huge one because I actually own the email addresses when people sign up. I can take that with me anyway. You can't shut down my email list. And so from day one, I had kind of an email collection box at the very top and at the bottom of every interview, just trying to get people's emails. And I think in the first week, We got like 1,500 emails and it was like kind of continued on that pace for a while. Like 1,000 emails a week from people from hacker news and all over the web who just like loved these success stories. Like they would come and read them and they would be like so inspired to hear that like, you know, so and so was making a 10 grand a month from like their travel startup. I'm like, I'm a developer, I could do that too. And so they would immediately get on an email because like they want more of these like stories. You know, they want more glances like what's possible so that like when the day comes that they're ready to start their startup, like they haven't forgotten where to go to see those examples.

1:03:26You gotta have some reason that like you're gonna show up for people like one of the things you know, I kind of joke about it I don't know there's no way to scientifically know but like and we didn't plan it this way but the fact that our podcast name is ACQ like in almost everybody's podcast feed we are at the very top because for whatever reason, podcast feeds are organized alphabetically. And like, how much benefit have we gotten from that? Like, I don't know, but probably sure we've gotten it. We get at the top of an accidental feed. Yeah. Yeah. I think it's a hard one lesson for a lot of people who are starting startups. Like if you're an anti 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.

1:04:15and the door, but it turns out that building stuff is kind of easy. Even if you're not a developer today, you can stitch stuff. I talked to a guy yesterday who built a whole slack bot without using code at all. I just even know how to code. And the hard part is getting people to actually care about what you're building and actually find it. So that means you have to actually solve... Well, it's like, and you run into it. Yeah, and run into it. Yeah, and it's not just run into it once. It's like, run into it. Repeat it all the time. Repeat it. That's very hard to do, but if you think about it, really carefully before you start.

1:04:43then often, you can come up with something. What I found is helpful is you just go to one of the places where people find things and you just look at what they're sharing. That's kind of accidentally what I did with Indie hackers. I was already in hacker news and it took days of me reading these threads before it clicked. Wow, everybody is here sharing this thing. Why don't I just make my thing better than what they're sharing here and then share it in the exact same place?

1:05:03Okay, so we've talked about this insight that you had that enabled growth. So we sound like circa 2011 YC. Tell me about your growth rates. Now let's shift to the indie hacker conversation. How did you start making money? Yeah, so actually what happened is 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. How much do you want to pay? And they're like, how much traffic do you have? And I told them like, sure, we'll give you like 750 bucks a month. And that to me was insane because everything that I had ever built was like some like rinky dink consumer app where I was like begging people to pay me like five bucks a month. Yeah, pennies and people were like, well, no, it doesn't have this feature. I can't possibly afford five dollars a month and then they'll go like buy like a bad coffee and like dump it out, you know?

1:05:55So, like, this company, like, offering me hundreds of dollars, like it was like a wake-up call. Like, oh, I can, like, make money from sponsors. But I was also, like, super focused on growth, because I was thinking, okay, well, I've got, like, maybe six months of runway. And I've got six months of savings in my bank account. I've got time. Like, why don't I just grow the site even bigger, because there's only one of me. Like, I don't have that much time to try to sell ads and build a site and do all these interviews I'm doing every single week. I'm just gonna grow it, not worry about money, and I'll worry about it later.

1:06:22So 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 HatGernews go figure. And so by December, I launched in August, by December, I was like, okay, screw this, I'm gonna start trying to make money. And so I started like basically emailing my list, which at that point I'd probably been growing to like 10 or 15,000 people and saying, hey, like, you know, here's the email with the new like this week's interviews, but also by the way, here's an empty ads lot, like your company could be here.

1:06:51And I was very lucky that it's the billboard that you see with the like your ad could be. Yeah, there's 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 any hackers are like some of the worst possible customers to buy ads.

1:07:14because these are very fledgling startups. These are people who had decided to start something because they read about it on Indie Hackers two months ago. And if they were going to spend $500,000 on an ad, that ad had better work. That's their whole yearly ad budget. It's almost like you would want a company that is selling tools to people like that.

1:07:35So I went through a lot of these awkward conversations where I'd run ads or people. I just wanted to do right by them, but the ads didn't always get enough clicks. And sometimes I would refund people. And I was just very stressful. I didn't like doing it. And so I created a dream list of companies. Which companies actually have a lot of money that would be good sponsors? I've no experience doing sales, but I'm going to have to figure out how to do this. And I had the very bottom of my list. My number one dream company, who should be sponsoring Andy Hackers, was Stripe.

1:08:01I'm like, okay, I'll eventually get to them, but I want to figure, I want my shit to be good. It's a warm-ups and it's a warm-ups. Don't warm-up on Broadway. Exactly. You don't want to embarrass yourself in front of everybody. I got some warm-ups. I sent a lot of cold emails. I found the heads of marketing on LinkedIn. My buddy, Jeff, who ran a podcast that was on, gave me his list of leads for who was advertising on his podcast.

1:08:23And to my surprise, it was way more pleasant selling to big companies than it was selling to small ones. I would get someone whose entire job it was to spend a marketing budget. And they would just want to talk about their kids, talk about their vacations, and be like, oh, yeah, you're cool. 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 were broke. Yeah, not to mention...

1:08:46One of my key startup lessons learned over the years has been sell to things that have budgets. Don't try and create budget, fit into a budget, and sure, there's emerging markets where the budget line item is not going to exist for your thing, but you're so right that if there's somebody whose job it is and they have a budget to spend, your life is just going to be so much easier. I think that applies to even coming up with startup ideas and trying to figure out a business model. It's kind of counterintuitive. People repeat this mantra, solve an unsolved problem.

1:09:14And it's almost like you want to do the opposite. Like you want to look at problems that people are already paying a lot of money to have solved and kind of like insert yourself there. Like my friend started a company called KeyValues. She's like been one of my best friends for years and name is Lynn. And like her company helps.

1:09:28Startups hire engineers and you know what like startups are hiring engineers just fine like well before her company came along But like we kind of picked that idea because we looked at like where are companies spending money? You know like where they spend a lot of money and it turned out like hiring engineers hiring recruiters was like a huge huge cost in every companies and like they were just willing to spend a lot of money on it and within like a year of starting her company She grew her revenues 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 and part because like she picked a problem where like people had

1:09:58budgets. Right. And I think the insight here is like, if you really want to overly simplify the sales process, there's educate and then win. like educate people that their need is real and then once they're convinced that they want to solve this problem, then go win and be the way that you solve that problem for them. And if you're selling into people with budgets, you don't really need to educate because they're totally bought in on solving that problem already. Yeah. And education is hard and it's risky because you might educate somebody and then lose because someone else comes alive and wins. Yeah.

1:10:29Or more frequently you educate somebody and they're like, hey, I don't know, I've got these other things that I need to solve. All right, so Broadway comes. So then you get a particular email. Yeah, so I don't know. I'm selling ads for a few months. I'm just happy to be honest, because I got to the point I think in February 2016 where Indie Hackers is going to pay all my bills. And I was like, wow, and less than a year I've gone from nothing to finally one of the ideas I've done works.

1:10:56You know, so I'm like... And so no, none of the other companies you'd worked on, you'd gotten to this point where it's like... No. Revenue is covering my personal sense. No, and it was better in literally every single way. I had added a community and so people were talking to each other. So I began to see a path where like, oh, I can do less work. Maybe people can interview each other and I don't have to do anything. People really liked it. I wasn't making to do this software where all I got were angry customer emails because I don't have the right feature. Every email I got was something positive. People talking about how inspired they were by an interview that they heard. It was just 100% good for my life.

1:11:28in every single way. So I was just 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 I hadn't gotten to Stripe yet on my list of sponsors to reach out to you. So maybe halfway down. And you went in the same batch, you didn't know them. I think during the Stripe beta, I'd maybe gone in there, looked a little Stripe chat room and pointed out some bugs and asked some questions. But I never really talked to the founders outside of that. And the email, I just stepped off of playing actually. I was going to a buddy's Batch the 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 a choir indie hackers question mark from like Patrick at Stripe. And I was like holy shit, there's like, there's no way this email's real. Like this is completely, like you're getting trolled. I'm definitely getting trolled. But I read it and it was real. And he was just kind of like, Hey, Portland, 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?

1:12:21And so the first thing I did was like, I forwarded to my mom, sent to my brother, sent to my friends. It's the hologram email over again. Yeah, yeah. It was like the coolest thing ever. And we ended up meeting and talking and kind of feeling each other out 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 of 2017. All right, listeners.

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1:14:18So if you're trying to turn AI ambition into real business outcomes and make it work safely, securely at scale, go check out servicenow.com slash acquired and tell them that Ben and David sent you lots to unpack here. Before we get too far into it, I want to understand. Let's let's relate it to our previous conversation on educating and then winning had stripe or end or Patrick decided.

1:14:41that they wanted to own an asset that was sort of a community of people talking about building stuff on the internet that very likely would need stripe to monetize and then you were the pick or was it like, hey, wow, that guys really got something cool. I think it's a combination of both.

1:14:56It'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 like idiosyncratic and like almost random how these acquisitions happen in many cases where it's like just like depending on how a particular person feels like this seems like the thing to buy and I think in my case Stripe has this kind of cool project internally called like the crazy ideas list and it's like hey everybody write down like the craziest ideas like If it's a reasonable idea, it's not allowed on this list. You need to write down just crazy things that we could potentially do that might win big. I think some version of Indie Hackers had been on that list for many years. What if we have a community for early stage startup founders? Just because we're a company like Stripe that wins a lot of business from early startups, these startups grow. They might be making $1,000 a month now, but like five years from now, they could be lift. And so winning the hearts and minds of early stage startups matters a lot. And so that idea was on there, and they just never did it.

1:15:53Right, because there's like maybe a thousand ideas on that list. And then I started Andy Hackers. It just worked. It worked really well. And it just like happened to very luckily perfectly align with what they wanted to do. Or it's like, okay, well, it's like empowering people to get started and inspiring them. And Stripe is a company that cares like a lot about its reputation. It's not an accident. Like that Stripe hasn't had, you know, any sort of major scandals like almost every other huge unicorn company. It's because the founders care a lot. And we like have a lot of good like well among founders and developers and like make a lot of decisions at the company that like are

1:16:22have that in mind. It's like to do best by people. And so, Andy Hackers was also a huge check in that direction where people just really liked Andy Hackers. They liked the positivity, they liked the optimism. It was all about how you can do it, how you can kind of stick it to the man and start your own business, it 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 both of those things are very good for a company like Stripe.

1:16:50that clearly wants more businesses to exist and more businesses to succeed. And what were some of your concerns once you started after you got out of the initial wave of, oh, my God, then you're like, wow, what would I sell this? Should I sell this? Like, how did you think about some of the trade-offs intentions there? Yeah, so a lot of my concern at the time, like, one of the things I was weighing heaviest on my mind was like, I just really didn't like selling ads.

1:17:14I was really not having a great time. I mean, I was making money. It was fun to get checks. But I wanted to make Indie Hacker's bigger and better. I wanted to spend a lot more time coding the community. At that time, the community only had maybe 40, 50 conversations a week. Now it's got tens of thousands. And I just wanted the time to do that. And so I was thinking, OK, if I go to Stripe, what are they going to have me working on? How much say are they going to have and what I'm doing? And how much does their vision align with what my vision is for the company? And if it's off by even a small amount, maybe that's not a big deal today.

1:17:44four or five years from now, that could be a huge deal. A small gap can turn into a really big gap. And so I really wanted to know, are we gonna be aligned? I wanted to know.

1:17:52because that's the betterment of the community. The people at IndieHack are like, is this going to be good for them? If you have a community and you have something where all your users are quite vocal, especially if they come from Hacker News, which most IndieHackers did, these are opinionated people. And they don't tend to look kindly on acquisitions that go wrong and watching their favorite products die. So I wanted to know, is IndieHack going to be better off for this?

1:18:14I wanted to know if I was going to be better off from this, how much money is this actually going to make me? How does it compare? The whole point of the indie hackers is exactly. If I'm going to no longer be technically indie, what is the trade-off I'm making? How indie will I be? I have this whole point that I make to friends. It always gets a mixed reception, but I think everybody's 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.

1:18:43If you want to learn how to improve your career, read a business book and think about yourself as a business. As an employee, you might seem like you have no power, but I learned from contracting. You have a lot of power. If you can make the value or the service or product you provide to your employer really unique, it's harder to fire you. It's more valuable. You can get paid more. You can get paid worth rather than being paid very little because you have so many competitors of the exact same job title as you. Some of the other parts of the employee experience relate to being a business. Everybody has marketing experience if you've ever made a resume, that's basically an ad. When you've shipped it out to potential employers, that's basically marketing. If you've done an interview, you've done sales because you're trying to sell yourself. I thought about myself in that light. How much freedom and independence am I going to have as an employee of Stripe? Who am I going to report to? What are they going to be telling me to do if anything? 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

1:19:38You gotta focus on doing it. You can't be pulling like, oh yeah, I know you're doing this thing, right? But we've got this bug. Can you just jump in and fix it? We've got to do this thing. You can get back to doing that thing, but we've got to do this thing. It's also completely different. It's also a completely different type thing. The average engineer, a bigger startup, is not...

1:19:58someone with a lot of startup experience. There isn't a road map for like, here's how you start a large community of founders. There's no step-by-step process. It hasn't really been done before. For some reason, there just aren't large communities of founders that have really thrived online. It's kind of easier to wait for somebody else to do it than it is to pick a random employee and be like, good luck, you're going to be able to do it. Where do you go make you a star? I mean, some people can do it but that's not why people typically apply to jobs because that's...

1:20:24you 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 gonna be? Like, am I gonna be like a normal striping player or not? And then, like, sort of the third box besides just like me and the community was like, what a stripe wanna 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 gonna 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 gonna work.

1:20:53If something is directionally pointing in the right direction and it can work, they're more than happy to take a chance. And with ND hackers and Stripe, it's kind of like, ND hackers doesn't really capture a lot of the value that it creates. If people start companies and their companies succeed because of ND hackers, because of a story they heard, because somebody helped them on the community, how do I make money from that? It turned out I didn't. But other companies do this that can capture that value, including Stripe. Because if Stripe is the best product on the market, what are they going to use for their new companies? They're going to use Stripe.

1:21:20And so Patrick, like, really just trusted like, hey, we think that you can make Andy Hackler's really big and 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 this contributed and sort of added when to our sales. But like, that's fine. And so a couple of questions here. I'll ask them together. You see no, 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 LA those concerns and what do you just leave to trust because ultimately these these things really are come down to do you trust me do I trust you and are we aligned so that's the first one the second one is how on earth do you go about figuring out what a fair deal looks like based on what your business was before it was acquired yeah these are tricky questions and I know I never feel like the most qualified to answer acquisition questions like people even though this is acquired people call me all the time like hey I'm going through an acquisition you went through one like

1:22:16What happened with you? I'm like, it's so specific to my situation. I had no employee. That was a solo founder, no employees. I hadn't even incorporated. But there's some little tricks and things that helped me. So the first thing that happened was that Patrick suggested that we communicate over text. So we got on WhatsApp, which instantly, I was like, oh, this is so smart. Because I had been sitting there, I think it was a Sunday, typing out an email, this acquisition numbers negotiation. And it was such a high pressure thing. What am I going to say in this email?

1:22:45versus text, it's just like so casual. You're just kind of firing off messages and it just lowers the stress and almost the adversarial nature of it in a strong way. So that was kind of the first tip. But then I thought about, okay, well, how do I value what indie hackers' worth? What am I going to be happy with here? And I think your first question was also how much does trust come into it? So the first thing I started doing was trying to answer both of these questions actually through back-channeling. So I just emailed as many people as I knew who were worth it striped.

1:23:13had dealings with Stripe or had dealings with Patrick and the past. I'm like, hey, what kind of person am I dealing with? And I got a lot of really positive stories. This is a person who cares deeply about what's good for people, et cetera, very ethical, et cetera. And I think you need that level of trust because in a contract, as I soon found out, there's so many random loopholes and edge cases that you haven't considered and just really easy ways to get screwed over. At some point, I was talking to Patrick and we were hammering things out.

1:23:42and at one point, I got an email that wasn't from Patrick, it was from Stripe General Counsel, and I'm like, oh shit. 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 her name was Mattal, she was great, but she was just the most paranoid person ever. She was like, here 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 every single contract that came, she found some way to tighten up the language or just go to bat for me, and ways were like, because I had a lot of trust. Perhaps an Iively, I just would have been like, ah, that's fine. They have the best intentions here. And so it's kind of like trust, but verify. I had a lot of trust, and I don't think I would have done the deal if I didn't trust that everybody involved was being sincere with what they said, that they're thoughts aligned with their actions and their words, but also having someone in my corner to make sure that these things wouldn't happen was important in gaming a lot of security. Well, the thing about these situations like this is

1:24:40the documents and the clauses and all that. They exist for when things go sour. Anytime you are looking at those documents, things are on a bad path. You don't ever want to look at them. But if you have to look at them, what is written in those documents is what is going to happen. Exactly. They're important. They matter. In my situation, what kind of happen is that we agreed on numbers?

1:25:07But at a very high-level, non-specific, this is what would make us all happy way. And that happened pretty quickly. It didn't take that long. And part of that was also doing research. How much did engineers strive to get paid? And by that point, I was pretty good at getting people to reveal numbers to me from working on any hackers. So I got a lot of numbers. And I was like, OK, this is what I want. And I was like, try to be a firm negotiator. But you kind of agree on these numbers. And then you go to drop a document. And it turns out there's just a million little edge cases.

1:25:34For example, if you're talking about stock, what kind of stock do you want? What class, when is it fast? What period is it fast? How long? How to refresh this work? All sorts of different things that I think if you're a typical employee, you might not consider. But if you're coming in through an acquisition, the sky is a limit. You can ask for a demand 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.

1:25:56For me, it wasn't just worst-case scenarios. Now it's this whole phase two of negotiations where we're talking about all these little details that we hadn't even considered. What mechanics did you put in place? Obviously, it wasn't like, okay, here's a bunch of cash. Welcome to Stripe. 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. How did you structure the way that there would be incentives over time for both sides?

1:26:26I don't know how much I'm legally allowed to say. Don't even get close. I think that what we're interested is how should people, if they're going into a situation like this, think about that? I think the first thing to be aware of is just all the different options that you have. I think it's very easy when you think about an acquisition to just think number. This company sold for X amount. But in my experience, rarely how it happens, it's rarely that simple.

1:26:51And some of the other options are just much more advantageous. Often companies will give you more equity than they will give you cash. And if you can evaluate the company, if it's Stripe, For love, I'm kind of like take that. Take the stock. If it's a group on, then I don't know. Maybe you want the cash. And this is the exercise. Well, this is the difference, I think, between sales force by Slack. It's about the number, right? Because it's a company bank. It's an entity bank, a corporate entity bank, a corporate entity with an indie hacker business. No, it's you. I don't know what Elon Musk's situation is, but he has all these weird earn out bonuses where he gets more money if the stock

1:27:30So even like those big company situations, there's all sorts of ways to sort of figure things out. If Salesforce buys Slack, what does that mean for Stewart Butterfield? Perhaps you could say, I want more money if we have these extra targets, et cetera. And perhaps Mark Benayoff would be like, sure, that's fine. And so I think if you can think about these creative ways.

1:27:48to align your incentives, it can result in a happier process. And maybe on both sides, maybe your acquire wants to pay you more if you hit performance targets, because the risk for them isn't the initial cash outlay, it's not going to pay off in the future. And so if they know you're incentivized to actually do a good job, then I think that can be one win, even though they're on the hook for more money in the future. In my particular case, it's funny because Andy Hackers is very much...

1:28:12and Andy Hacker Business. I was just making money from advertisers. I had some affiliate links on the site. I think I was making $7.5, $8,000 a month. by the time Stripe acquired the company, where it's like, today I feel much more like a high growth startup. We're 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. And we have kind of a budget, which is almost like funding to help us grow. And so it was like, we're 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.

1:28:47You know, the comp at that point is more to entrepreneurship, 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 a stripe Atlas. Yeah, I mean, I think branding is the by far the biggest difference because it's pretty obvious to most most people who are aware of Indie hackers know that Indie hackers started before stripe.

1:29:27And they know that it's kind of like my thing. I'm very transparent. They're going to listen to this podcast and clearly Quirlin is running this on its own. It's not like a super heavy-handed striped initiative. Plus, a lot of people don't even know Andy Hackers is owned by Stripe. There's like a very small little logo that says at Stripe at the very bottom of the website that you kind of have to search to find, which is freeing it away because it gives me the ability to make my own decisions that don't necessarily reflect on the Stripe brand.

1:29:52I remember a buddy of mine at Stripe, kind of ran the Stripe Atlas community, got an email from IndieHackers. He's like, oh my god, you said fucking an email, like a Stripe email. And I'm like, I said fucking, like, I'm probably like, I don't know. There's no one at Stripe who's that kind of monitoring that. There's a lot of trust that goes both ways. I trust Stripe and they trust me. And it's weird in a way. I feel like a lot of the positive things and feelings to people have about IndieHackers sort of get accrued to Stripe.

1:30:19but some of the more riskier decisions don't weigh on Stripe at all. So it's almost best of both worlds where I think if I started some Stripe product internally, like Stripe Press, that has Stripe's name literally in the name, which means it's a certain level of quality that it has to rise to. There's a certain standard that it has to rise to. It's harder to get things off the ground when you do that. You need to match certain accessibility standards and have a certain reach of people in different countries and have all these different languages.

1:30:45And I think it's just harder to iterate on any sort of like startup type initiative that's trying to find product market fit. If you have all of these expectations on you. This is why I think it's smart for like Google when they're doing their innovations to like try to like Spend things out of the Google brand and just have them be like dissociated So like people don't have these expectations because you just kind of need to start with something embarrassing and rough and what I've been doing for the last YouTube's a great example right like when Google bought YouTube There was still like the black homeloss who was going on like there was all sorts of you know people were up in arms. There's crazy stuff happening They're still as crazy stuff happening on YouTube but now it's like Google video was a failing product

1:31:24Like it was trying to do the exact same thing but was going through Google. Yeah, they weren't gonna just put movies there that were filmed with you know, camcorder and a theater like you could take bigger risks through an acquisition, especially of like an established brand on its own. That's really cool. All right, so tell us now why has it made sense for Stripe and.

1:31:47I 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 striped divinity hackers? What have you built to do in the integrations, if you have? Yeah, so I mean, it's worth like noting sort of my working style at Stripe is that I reported to Patrick since I got here. We don't meet all that often. You know, there have been years when we met like twice, either years away, I've sent them 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 meeting Patrick maybe nine months after the acquisition, and he was like, oh, this looks really good. I was kind of worried that for you to grow.

1:32:29You 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. We were doing nothing but putting out these interviews. And we had this very fledgling community forum, but you had to click a link to get to it, and it was only a small number of people. Whereas today, the bulk of what happens on Indie Hackers is sort of usurpoured. It's more of an actual platform where I'm not doing...

1:32:52The vast majority of the value that Andy Hackers creates to the world does not come from me. You did it. You shifted from media company to software product. Exactly, which I always wanted to do, but it took Jesus to take a long time. Probably I would say the biggest accomplishment since joining Stripe was just the growth of the community forum, which is now on the homepage. If you go to AndyHackers.com, you just see dozens of conversations where hundreds of people are helping each other out, asking questions, and helping each other start companies, meeting co-founders, without me really doing anything.

1:33:21The company profiles you create through interviews and that people create themselves, they're all mixed together. Yeah, kind of. And I've been trying to consolidate things and not quite consolidate it yet. So there's kind of a separate section on the website where you can go and you can read and then we've done about 500 interviews now.

1:33:36All the different interviews from indie hackers who've kind of shared their stories. And like you can kind of sort and filter those. You can also go to sort of the product directory, which I mentioned earlier, where it's just more like self-serve. Like anybody can add a product there. You can share how much money you're making, share your milestones along the way, and everybody's sort of there, competes to have like the best milestone every day. So with this leaderboard that kind of resets and ever post 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.

1:34:05which has a side effect that everybody else can go read the timelines and learn how to build a company from these examples. So that's grown to like 12,000 products. We've got 500 interviews. We have a podcast that went from, I think just maybe like a thousand downloads total when Stripe acquired Indie hackers to now millions of downloads. And the community forum has gone from just a few dozen conversations a week to the point where there's like a thousand comments a day, over 250 posts every single day in the community forum. And just like tens of thousands of people helping each other out. So, you know,

1:34:34Based on the numbers, Andy Hackers has grown tremendously since we've joined Stripe. One of the things that we like to measure is a rough estimate of how many people have started companies as a result of Andy Hackers. We send out a survey to people maybe six months or so after they join. We ask them true or false of different questions. One of them is, would you have started your company if not for Andy Hackers?

1:34:58And 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 Indy Hackers. And if you multiply that by like 140,000, you know, different people who joined the community forum, like that's, that's a very substantial number of company companies. A lot of tiny companies. And some of them have like gotten bigger, gotten acquired. A lot of them are on strike. And sort of the way that, Patrick explained to me earlier when I first joined Stripe was like, Hey, it's your job to, you know, get people to start companies. It's our job to have a product that's good enough to win them over. You know, I'm not like sitting here trying to like hawk Stripe and convert people to Stripe. Like that's something that Stripe does on its own. And what was that 140,000 user number when you were acquired? Yes. Let me look it up. I'm also curious. I'm, this is the third time I've done this to you. I'm queuing up two questions. Approximately what percent of indie hackers use Stripe?

1:35:55as there for their company. So the second one, I don't know the answer to. We don't really have a process. We don't measure. It's a lot of just trust. We know that Stripe is pretty damn good. It's a product. It comes up on the community forum all the time. I think it was the most reference company and all the interviews that I did even before joining Stripe. I mean, honestly, I don't even know what else you would use if you want to take payments on the internet. You could use a ton of other stuff, but they're just custom services that are way labeling Stripe.

1:36:24Underneath like that's what glow is like. Yeah, like I don't even know if there is another alternative. It's it's it's a really good product. Yes, David. There are alternatives. It is also a very very very good product. So for me to alternatives worth using. Yeah, let's put it down. Yeah. So for me to answer your question on exactly how many users are wearing a joint stripe after running like kind of a query. It'll probably take me like a couple minutes. So like is it worth it? On air SQL writing. Well, do you have any mental ballpark of what?

1:36:52Like on the order of 1,000, 10,000? It was on the order of like, certainly fewer than 5,000, probably more than a few hundred. All right. That helps us understand, I think, the scale. And it's been what, three and a half years? Yeah. It's been three and a half years. I joined in April, 2017. So any actors has been a striped for much, much longer than it existed before striped. That's really cool. 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. That seems like a great outcome for Stripe. They're 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, and what would have happened otherwise.

1:37:50We've done a lot of playbook as well, but we can specifically call that out. If Stripe hadn't acquired indie hackers, it's not like all the companies that have been created wouldn't have used Stripe. I don't think you'd influence any of their decision on who to use for payments. What they were really doing is saying, Man, this thing is really good for our business that it exists. Let's make sure it can thrive as much as possible. It's interesting to me trying to think through the scenario where Stripe didn't acquire indie hackers and the exact same outcome happened for Stripe. Yeah. Again, I don't measure, you know, would you have used Stripe? It's not even my goal, really, to make people use Stripe. It's my goal to make people start companies.

1:38:35I want people who 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. When they hear a story on the anti-hackers podcast, when they go on the forum, they see somebody who's like, I'm at 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 anti-hackers.

1:38:53You know what's your experience with it? It's like oh I read the story you did with this guy you started this like review site and I'm like I'm way smarter than this guy. I could start a company So I did then I got into YC and now I don't go to any hackers anymore And like that's pretty it's pretty common like I meet a lot of people like that He was just like inspired like they literally started because he just read that it was possible and when I think about like me like I started my career because like people told me it was possible You know and I think spreading those stories helps people get started and like that's literally all I care about like I don't care

1:39:20How many of these people end up using Stripe? That's the job of Stripe engineers and product managers. It makes Stripe the best product. It looked like you were writing some SQL there in the background while I was pontificating. Where'd you come up with? We had exactly 1,400 and three users on the day that we got acquired by Stripe. We're a 100x bigger today. Almost exactly 100x bigger. Almost exactly 100x.

1:39:44Just pretty cool. It's cool to see how that- Wow, that's cool. There's a lot of stuff to look into too. It's like, okay, well, how much bigger is the podcast? How many more conversations are people having? Because it's not just about having more people, but it's about engaging them more. How many return visits do people have? And we track a lot of random stuff, but number of users straightforwardly 100x bigger in three years. 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.

1:40:12Did you see these stats that came out last quarter about like new business creation? Or it's like like 600,000 people a quarter in the United States for 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. So it's doubled.

1:40:35Aren't there more and more winner-take-all opportunities? Are we seeing, now we're well into playbook, but are we seeing basically a barbellification where the big startups consolidate to only a few big winners in each market, but then there's massive, massive opportunity to go after a long tail? Yeah, I think number one, there's a lot of these winner-take-all startups, but almost all of them create niche business opportunities for other founders.

1:41:01And 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 turns out a ton of media companies get started off the back of that. And a ton of app companies get started off the back of that. And there's companies that teach you how to build a Facebook page and get started off the back of that. So I think as an Andy Hacker, you don't have to worry too much about the winner take all companies.

1:41:20And then we have all these platforms, you know, YouTube, sub-stack, only fans, arguably, you know, Twitter, where people are just like building audiences and businesses off the back of all those things. And so what's kind of cool is, it's kind of like never gonna be, you know, all the niches are taken, there's no ideas left. And also, I think when people underestimate, it's just the number of people adopting technology for the first time. Because just because like Zoom exists doesn't mean everybody uses it. Like we've seen very clearly this year, way more people are using Zoom, because they've been forced to adopt this thing that's been kind of ignoring in the past, because they just like didn't want to.

1:41:49And so as more and more people get on the internet and create businesses and 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 the self-fulfilling sort of chain reaction where there are more businesses that are the more like products they need. And so it's kind of cool to see it accelerating. And I wouldn't be surprised if that number, you know, in a few years, it's like five million Americans a month are creating an online business. Yeah, that's what I was thinking on. That is like, you know, you've got the platforms.

1:42:16Like, say, let's involve a stripe or Shopify. And then you've got people that start Shopify stores or start businesses on the internet and you stripe. But then there's this whole other category that I think is perfect for any 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.

1:42:45they're a business that provides a custom set of tools for a certain set of users that need like hobby businesses like your hobby game store and you are both buying and selling from your customers like your customers come and they trade in stuff like you can run on Shopify great but like you also need some custom functionality to buy stuff from your customers.

1:43:04Boom, business. Exactly. And I think a lot of the smarter founders are figuring out ways to kind of escape the competition because it's like, okay, you can build a Shopify plugin, but there's a lot of other Shopify plugins. So it's a cool opportunity, but then you get kind of crowded out. I'm talking to a guy tomorrow whose name is Jordan O'Connor. And he's got a really cool story where he's a father, a husband, he had a full-time job, and he would eat out time every morning to kind of work on his business because he knew that...

1:43:31after like 8 a.m., his son was gonna be awake and 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.

1:43:39for this app called Poshmark, which is huge. A lot of people buy and sell, they're used clothing on Poshmark, but they don't have a marketplace. They don't even have an official API. So you just sort of reverse engineered things. He's like, there's not gonna be any competition here, but it's kind of the same playbook, like build for this, an ancillary tool for this bigger platform, and he built a bot that helps you do well on Poshmark. And I think he got to 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 doing other fun projects now that like,

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1:45:15All right, well, I'm gonna start bringing us home here. Cortland, answer this question, however you see fit, but how would you grade the indie hackers acquisition by Stripe in terms of was that a good use of capital and resources for Stripe?

1:45:27Oh, a plus. I think it's, I'm slightly biased here. 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 good well 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 they aren't happy that it happened.

1:45:57It's hard to imagine it having gone better. Yeah. Should more people do this? I mean, the way that I'm sort of categorizing this in my head is they made an investment to ensure the continuity of this thing that was creating new customers for them. And like, do other companies do that? Should more companies do that? I think there should be a lot more creative and imaginative. I think like there's, like as humans, we have this impulse to just like mess with things. It's really hard to buy something.

1:46:23and 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 gonna do with it? I think, oh, that's gonna be like so much work, I have to do this, I have to do that. And they don't like make these acquisitions whereas I think it striped very very much like, no, Portland'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 gonna see going forward is like tech companies basically owning like some kind of media company.

1:46:51which I think is super powerful because like media companies are what connects with actual people on the ground. And in a way like IndieHackers is still very much a media company. Like I still spend a lot of time in the podcast. I spent a lot of time in our newsletter, put out a ton of content, and we're sort of like becoming a platform, almost like sub-stack-ask, or we're enabling other people to sort of build newsletters.

1:47:09and grow their audiences on Indie hackers. So I think even without just having Indie hackers continue to exist, and even without it driving access additional customers to Stripe, it's just a good way for Stripe to be able to communicate in the future if it wants to. We're launching this thing, we think this is about the world, and now they have a place that's not just hacker news or Twitter to do that. Has Stripe done anything else like this since you've been bought? Yeah, Stripe has a magazine called Increment Magazine.

1:47:36just 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 I should work 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 involve often people who are like come in from outside the company and help. They're all like kind of moonshots. I put it in a very similar category to Andy Hackers, even though it's like...

1:48:18You know, different. But it's something that most companies wouldn't do. But like Stripe kind of trust, like, okay, well, what if we put out like these books that like help people become better founders, make better decisions, start more companies. It's hard to measure like how many people actually read this book and made a decision because of it. But like we can kind of trust that like they will do that because like we know that's how inspiration works. And like it will increase Stripe's bottom line. Yeah, it makes total sense.

1:48:41For 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 Portland properties? Yeah, I mean, the easiest way to really get into indie hackers is the podcast. So if you just go to your podcast player and search for indie hackers, it'll 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?

1:49:10How can you start off maybe as an anti-hacker, then eventually grow to start a much bigger company? I've interviewed lots of founders of YC funded companies and VC funded companies, but also tiny anti-hackers you don't want to grow anymore. So check out the podcast, and you can find me on Twitter at CS Allen. Awesome. Well, listeners, we hope you have a happy holidays. It has been one of the best parts of our 2020 being with you all, and we will see you next time. We will see you next year, cannot wait for 2021. But seriously, I'm in the best part of 2020 hanging out with you all virtually. It's been a great year. The world is sad. It's been a great year for acquired community. Can't wait for next year. See you in 2021 everyone.