Acquired - Special: Acquired x Indie Hackers

Episode Date: December 17, 2020

As regular listeners know, we typically cover some of the biggest companies who often receive the most media attention (see Airbnb and DoorDash). But today's episode is a little different. In... our conversation with Courtland Allen of Indie Hackers, the largest community of startup founders, we dive into the stories of underdogs. What happens when there are millions of people doing small business entrepreneurship? How does anyone having access to the globally addressable market of 3 billion internet users open the door for the niche-est of products? We tell the story of Courtland’s own “Indie Hacker” journey, how he came to found Indie Hackers itself, and the lessons learned along the way. Sponsors:ServiceNow: https://bit.ly/acqsnaiagentsHuntress: https://bit.ly/acqhuntressVanta: https://bit.ly/acquiredvantaMore Acquired!:Get email updates with hints on next episode and follow-ups from recent episodesJoin the SlackSubscribe to ACQ2Merch Store!Playbook Themes from this episode are available on our website at https://www.acquired.fm/episodes/special-acquired-x-indie-hackersLinks:Indie Hackers: https://www.indiehackers.com

Transcript
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Starting point is 00:00:00 I've got new M1 MacBook Air. It's the first episode we're doing on it. Nice. Nice silent recording in the background. No, what do they call it on the Pro? The active cooling system. Don't call it a fan. Welcome to this special episode of Acquired, the podcast about great technology companies and the stories and playbooks behind them. I'm Ben Gilbert, and I'm the co-founder of
Starting point is 00:00:35 Pioneer Square Labs, a startup studio and venture capital firm in Seattle. And I'm David Rosenthal, and I am an angel investor and advisor to startups based in San Francisco. And we are your hosts. As regular listeners know, we typically cover some of the biggest companies, those that IPO, see Airbnb and DoorDash last week, and the companies that get some of the splashiest press coverage.
Starting point is 00:01:00 But today's episode is quite a bit different. In 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 3 billion internet users open the door for the nichiest of products? And importantly, what was Cortland's lived experience of starting his own string of companies that ultimately led to starting IndieHackers
Starting point is 00:01:30 and its acquisition by what is now the hottest private company in the world, Stripe? Yeah, man, last one left standing after last week. No kidding. And a lot of people cannot wait for it to IPO soon enough. I can't, that's going to be, I got to imagine our biggest episode of next season, hopefully next season. When is this thing going to happen? Season eight, season nine. We'll see, David. We'll see. Well, as always, if you love acquired and you want more, well, good news. We have the answer
Starting point is 00:02:03 for you. The community of Acquired Limited Partners is now an army in the thousands. For those of you who aren't already a part of the gang, becoming an LP gets you twice as many episodes, access to live events with us and other LPs, even in an all-virtual 2020, and most near and dear to David and my hearts, you have the biggest influence on what we cover in the show. So if you want to join, you can click the link in the show notes or go to acquire.fm slash LP. Okay, listeners, now is a great time to tell you about longtime friend of the show, ServiceNow. Yes, as you know, ServiceNow is the AI platform for business transformation,
Starting point is 00:02:42 and they have some new news to share. ServiceNow is introducing AI agents. So only the ServiceNow platform puts AI agents to work across every corner of your business. Yep. And as you know from listening to us all year, ServiceNow is pretty remarkable about embracing the latest AI developments
Starting point is 00:03:01 and building them into products for their customers. AI agents are the next phase of this. So what are AI agents? AI agents can think, learn, solve problems, and make decisions autonomously. They work on behalf of your teams, elevating their productivity and potential. And while you get incredible productivity enhancements, you also get to stay in full control. Yep. With ServiceNow, AI agents proactively solve challenges from IT to HR, customer service, software development, you name it. These agents collaborate, they learn from each other, and they continuously improve, handling the busy work across your business so that your teams can actually focus on what truly matters. Ultimately, ServiceNow
Starting point is 00:03:42 and Agentic AI is the way to deploy AI across every corner of your enterprise. They boost productivity for employees, enrich customer experiences, and make work better for everyone. Yep. So learn how you can put AI agents to work for your people by clicking the link in the show notes or going to servicenow.com slash AI dash agents. Okay, now on to our crossover episode with IndieHackers. Cortland Allen, welcome to Acquired. Ben, David, thanks for having me. So great to have you here. Our pleasure. For anyone who has not listened to your voice for the many hours that I have on the 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
Starting point is 00:04:29 crossover episode with you. Yeah, I'm excited to do this. People have been asking for a while for me to do an episode on myself, because obviously Indie Hackers is kind of an interview show. I just tell other people's stories. And I've always been like, as weird as it sounds, like shy to do an episode on my own podcast. So congratulations on being the first people to convince me. Well, look, we are the acquired podcast and you did that mega deal exit to Stripe. So how could we not, you know, cover the acquisition of the century? This is great. It's got like all the hallmarks of both of our episodes. We'll see how that goes. Well, David, who is Cortland for listeners who don't listen to any hackers or haven't participated in the community. Yeah. So Cortland is a former YC founder, MIT alum, and founder of a company that has been
Starting point is 00:05:14 acquired by Stripe, all of which seems like it would fit very much into the acquired theme. But there's a twist. Unlike the big gopher broke, 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 standard oil out there, except 10, 100, 1000 times bigger than the Rockefellers and the Carnegie's could ever imagined. Cortland is all about a different philosophy out there, the indie philosophy, and of course, the company that he started and what he runs within Stripe and the website and the community and the podcast is Indie Hackers. And Indie Hackers, I think is really cool. We're going to get into in this
Starting point is 00:05:55 episode. It's kind of like if big tech and startups are the Rockefellers, this is the small business entrepreneurship of the 21st century. And I think it's really, really cool. So we're pumped to do this. Yeah, you said IndieHackers is not a big, splashy, go-for-broke story, David. I don't know. You're going to tell us. No, it's really not. It's really the story of... I like to think of it as the underdogs. The internet's been around for decades. And I think the world is still slowly waking up to how much it's changed the game for just regular people. Everybody's connected to everybody. And you can reach literally millions of people, if you're clever enough, for pretty much $0. And so people are creating these very tiny niche businesses that could never have
Starting point is 00:06:33 existed 20 or 30 years ago. And in some cases, not even 5 or 10 years ago. And I think it's becoming possible to sit down in your living room, wearing your underwear or whatever you're wearing, and just create something that's super valuable to your community and your customers. And that's really kind of fun and fulfilling and challenging for you to work on as a person. And that makes you rich in the process. And I think that's pretty crazy to check all three of those boxes. So thousands of people are doing this today. And the question that I'm asking myself constantly is like, what happens when millions of people are doing this five or 10 years from now?
Starting point is 00:07:02 Yeah, I think that's what's so cool is like, small business entrepreneurship in the past was a great way to build wealth and do well, you know, for your family and for yourself. But with the same or honestly, like less amount of effort now on the internet, this path exists, that the wealth you can build even by taking this path is still so much bigger than you could build, you know, building a dry cleaning business in the past or running a restaurant or a lot bigger, not to foreshadow our sort of playbook too much, but it does remind me that, you know, in a pre internet era, the local small business owner was geographically constrained and they could, you could have a general store that sold everything, but it could only sell everything to the people in your town. And obviously, the sort of like large scale version of that is Walmart.
Starting point is 00:07:49 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. Every time I listen to an episode, I get smacked in the face with, wait, that niche is that big? And people find these crazy opportunities. I just listened to the Patio 11 episode and he was talking about bingo card creator. And I'm like, a bingo card creator could be a business, but these niches are so deep or so wide or however you want to describe them. If your TAM is the 3 billion people with the internet, then every niche within that TAM can be on its own big. Hey man, Starlink's coming soon. It's going to be 7 billion.
Starting point is 00:08:31 Exactly. If you have like a business that only appeals to like, you know, one in a thousand or one in a million people, you need to live in like a very big city to create a brick and mortar business that's going to survive. But on the internet, like that turns out to be millions of people who can use like your underwater bingo card creation, whatever it is that you're making, which means that like pretty much everybody can figure out something really specific that no one else is doing and kind of stake their claim on the internet, which I think is super cool. I hear the real estate is cheap too. All right. So let's get into your story. Okay. Let's start way back before MIT,
Starting point is 00:09:04 your family and your mom specifically was an entrepreneur when you were growing up, right? Yeah. So I had... I was just talking to Jason Kalakonis about this on his podcast, where he was talking about opportunity. Can anybody start a company? Does everybody have an equal chance to do this? I think, in a way, nobody's quite equal. Everybody's got a different starting line. And when I look at my childhood. Everybody's got a different starting line. And when I look at my childhood, I had a very good starting line. I had two loving parents. They were very attentive. They were very devoted. We were middle class, but very comfortable.
Starting point is 00:09:38 And like you mentioned, my mom was an entrepreneur. She was always doing her own crazy hijink startup, selling computers and stuff in the 90s. And my dad was part of this elite team of furniture makers. There's nine of them. And they each had a differents. And my dad was part of like this elite team of like furniture makers. There's like nine of them. And they each had a different role. And they would make like crazy furniture for like celebrities. So he wasn't making like a ton of money, but he was doing something that he found really fun. He was like the furniture finisher. So he'd take like an ugly piece of wood and make it look like amazing. And I grew up like these two people in my lives who kind of showed me that you can do pretty much whatever you want and like kind of scratch out a living. Yeah, you can do this and like it'll be fine. You can have like a good life,
Starting point is 00:10:09 right? Yeah, exactly. You can have a good life. You know, like we were eating, we weren't missing meals. I had a bunch of other advantages too. You know, like I was an American. I was born in the late 20th century because of my mom's computer business that she ran for like a year or two before it crashed. Like we had a computer and the internet when I was in the third grade, like right after the web came out. And so, of course, like I was addicted to video games and like whatever I could play. But from the adult's perspective around me, they're like, oh, this is a computer whiz. You know, whenever I've got a computer issue, Cortland spends so much time on his computer, he can just like swoop in and fix it. So I was like doing all this IT work on the
Starting point is 00:10:39 side. And of course, nobody ever paid me. I made $0 like as a nine-year-old fixing people's computers. But I got a lot of positive encouragement because from my perspective, I was just like, you know, playing games and fixing bugs and stuff. But from like the average adult's perspective in the mid 90s, they were looking at like the tech boom and they were looking at Microsoft's stock price and the fact that Bill Gates was like, you know, mega rich. And so they would sort of pay me an encouragement. They'd be like, oh yeah, you're going to be like the next Bill Gates, like keep it up. And what was cool about that was, you know, I got to be like a little computer nerd and also see that like this really like old computer nerd
Starting point is 00:11:12 was universally respected by like every single person that I ever met. And everybody told me that it would be a cool thing to aspire to kind of be that. So by the time I was like 10 or 11, I was like, okay, I want to be Bill Gates. You know, I want to start my own company. I want to go to a good college. Like how do I, how do I get on that path? In some ways, it's like echoes of the Tim Sweeney story and Epic Games, you know, him starting out first with, it was his older brother, right? Right, Ben, that had a computer hardware business. And so he like went out to visit his brother, got hooked up with computers, got obsessed, then started like an IT consulting business after the lawn mowing business nolan bushnell too i remember when we
Starting point is 00:11:48 asked nolan about starting atari he was fixing tvs and not at all to put myself in the same category i was fixing teachers computers in in middle school as my uh i think i was making like seven bucks an hour currently so sorry i was uh dwarfing you there but yeah that's so many people's entree before they actually get into programming is basically just fixing stuff. Yeah. And I think it's important. Like I've taught people how to code in subsequent years. And there's this kind of base layer that gets ignored of just like computer literacy, where the people who learn the fastest are people who just like, they're just very comfortable if their computer crashes or has an error, like they know all the keyboard shortcuts, they're good at Googling stuff. And if you have that kind of
Starting point is 00:12:22 base layer of skills, it makes everything else much easier. So you're 11 or 12. At that point, you know that you want to go into a technical field or programming or computer science. Did that ever deviate? Or was that pretty much like, nope, laser focus from that point forward? Man, I had this real embarrassing phase where I was trying to choose between, do I want to be Bill Gates or do i want to be kenny g so i had a saxophone i was playing like a lot of like just corny contemporary jazz music uh and luckily luckily the computer stuff won out at some point and after that like i didn't deviate like that was a hundred percent what i wanted to do i had a ton of like just a ton of fun just like doing stuff in the 90s on my computer, like a lot of support around me. And, you know, in one way, I think I had kind
Starting point is 00:13:08 of like the world heavyweight champion of childhoods, you know, it was like really, really good, like really advantageous. But I also had some hardship. Like my dad died when I was pretty young. I was in high school. And like for me, that was just like a huge wake up call. Like, oh, shit, sometimes things get real and like no one's going to kind of swoop in to save you. You have to kind of learn how to survive and make it through tough things on your own. And so I got like almost like kind of the perfect mix of like hardship and like encouragement and like privilege in a way. And so, yeah, by the time I left to go to college, I felt like pretty ready to take whatever the world was going to throw at me.
Starting point is 00:13:41 And also like pretty far ahead of the curve in terms of like knowing what I wanted to do. Like there's never a question like what major do I want to have? You know, what do I want to do after I graduate? Like I was always 100% certain what I wanted. And I'm sure that tragic, you know, death in the family also forces a lot of early maturity that you have to take on sort of more responsibility or at least think about the broader context around your life than just yourself earlier than you otherwise would have. Totally. And like, I think for me, the biggest impact was just like, you kind of get like a floor, you establish like, okay, this is the worst thing that's ever happened to me. And like, I survived it, you know, like it was terrible, 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
Starting point is 00:14:20 of other things just don't look that scary. Like they don't look like that big of a deal. Like, okay, what if I start a company and it fails? Like, oh no, I'll go get a job. Nobody died. So I think that's kind of what I got out of it. I assume that the love of computers and knowing what you wanted to do, getting out of the Kenny G phase, that's what brought you to MIT.
Starting point is 00:14:39 The Kenny G phase was a good one to escape. Yeah, so I remember really wanting to go to MIT. I somehow figured out that that was 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. If I had known that and that it was in the heart of Silicon Valley, I probably would have tried to go there. And I also didn't know that it was even feasible to just not go to college.
Starting point is 00:14:59 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, like, you know, how do you get into MIT? And she's like, well, good, good grades and study and apply. And like, hopefully they'll let you in. I'm like, well, what if they don't? And she's like, you just go somewhere else. And I remember thinking like how frightening that was. Like, I got like one shot to do the thing that I wanted to do. And if I got rejected, that I would just be done. And in a lot of ways, like that was a much scarier thing than I think starting companies that like have the risk of
Starting point is 00:15:24 failure. Cause like you can start a company a million times. Like if it fails, like there's no like, all right, you know, that's it. You gotta go somewhere else now. Like you can just keep doing it over and over again. Well, how many companies have you started now? Seven. Andy Hackers is my seventh attempt to do something that worked. And the only one that really, that really worked. So yeah, I was going to say, so when you get to MIT, you, I think if I understand the history, you start applying to YC like regularly.
Starting point is 00:15:51 Yeah, yeah. I played a lot of times. So is this like a like every quarter thing? It's like register for classes, put in the YC app. Well, I was like a pretty bad student. I didn't understand like the idea of like, I just didn't really want to learn. And I thought all the stuff I was learning in my CS classes was boring. And so I spent a lot of time working on my own side projects.
Starting point is 00:16:07 And at some point, I discovered that there's this magical entity out there that will give you a bunch of money to take your project and try to make a company out of it. So I got really hooked. And I would spend a lot of time applying. I got rejected at least two or three times. Had Dropbox already gone through YC at this point? At some point during when I was in college, Dropbox like went through and Dropbox was also an MIT startup. So everybody on campus had like a bunch of free Dropbox codes and we had like a ton of free space and everybody knew their story. So there's a lot of like positive encouragement there as well. Like, oh, you want to apply to YC? Like everybody knows what that is and thinks it's cool to just apply, even if you get rejected. Like I got rejected once and I got an email from Paul Graham where he was like, Oh, I think, you know, you could have done like this better. I remember just like showing that email to my friends, like so proud, like look, PG responded to me. This is just a rejection. Basically.
Starting point is 00:16:54 Oh, that's what were some of the ideas you're applying with? So the very first one was this company called Fmail, which stood for like, get this Gmail for Facebook. Facebook released like their platform sometime when i was i think a junior and at that point like i'd never really built like a web app but a buddy of mine was just like super encouraging he was like oh this is so easy coral and just go learn php and i'm like php like what is that so i went online i started learning it and he's like okay i'm like well how do i extort user information facebook was all php yeah yeah it was all php and i just kept asking like oh how do i do this? He's like, oh, just go learn SQL.
Starting point is 00:17:26 And after a semester, I learned all this different stuff. And I'd been able to build this app from scratch. And I thought it was amazing. Like, oh, I didn't know anything about this stuff. And now I can make my own web app. And I applied for YC and, 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 publications just wrote about it.
Starting point is 00:17:48 They're like, oh, crazy MIT genius figures out a way to put a Gmail inside of Facebook. We'd scanned it to look like Facebook. And it barely even worked. It was super crappy. But I was like, wow, it's really easy to get the press to write about you. And you can do a really simple thing that takes you a semester, even if you're a total beginner. And it's kind of creative and kind of unique and people haven't seen it before. You'll get attention. So that was a kind of a good experience, even though I got rejected. And that was an era too, where there were so few web products where when you did one and you made a new website, it could kind of stand out because there just wasn't a lot of noise. I remember you flood back so many memories there. When I was in college, it's funny, yours was Fmail. Mine was called Hacker Follow. And it was Twitter for Hacker News.
Starting point is 00:18:29 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, I learned PHP and MySQL to be able to store the stuff in a database. And I mean, that's what everybody did then. 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, like the quaint times of 2020 when you could do anything and it would get attention, you know? And like, to some degree, like that's true. Like if you spend, like very few people have the time to sit down and just like think creatively about ideas and like one of the
Starting point is 00:19:09 easiest ways you want to come up with any creative idea is just to take like two or three things and combine them because like once you do these combinations like you instantly start getting to ranges where like no one has ever done that before like if you type like the dog into google you're going to get like 10 billion results but if you talk like the dog left you're going to get like a million results and if you like type like the dog left the store with a bone, there's going to be like no results. It'll be like a sentence that no one has ever said before in the history of like the world. And then the same thing is true with ideas. So I think there's always kind of like this, this sort of framework you can use to come up with interesting
Starting point is 00:19:39 ideas. And like, we both found kind of the same one, you know, like, Oh, let's take this one thing and put it inside this other. And like, that was enough to stand out. And I think that's still true today. Yeah. Okay. So you mentioned Hacker News, which I assume is going to continue to play a big role in the story here. Were you hanging out on Hacker News while you're at MIT and doing all these YC applications? So back in the day, like Paul Graham used to write on his blog all the time about startups and like all sorts of like different stories. And it was like, he was very motivational, inspirational and positive. And then he had this website he created, which like, again, he just like seemed like it was
Starting point is 00:20:11 very haphazard. He's like, what if I had like a little Reddit clone? And of course, it's like now like millions and millions of visitors or whatever. But if you wanted to apply to YC, like you had to be on Hacker News. Yeah. Ben, you know the story, right? It exists because he was dissatisfied with our programming and was asking alexis to make that better like alexis and steve i think it was either to make it better or maybe to invent it at all because they're that subreddit didn't exist yet and got frustrated with their slowness and started hacker news yeah 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
Starting point is 00:20:44 i'm pretty sure that's against some sort of code of ethics. But you kind of had to have a Hacker News account to apply to be in YC. And like, not only did you want to have a Hacker News account, but you wanted to have like a history of like smart, like intelligent, thoughtful comments, because you know, Paul Graham and the partners are going to look at what you had posted. So if I look at like my YC account right now, I think it's like, yeah, created October 8th, 2008. So I was on YC account right now, I think it's like, yeah, created October 8th, 2008. So I was on YC like way back in the day, reading everything, digesting everything, and then trying to leave smart comments that like, I would be probably embarrassed to go
Starting point is 00:21:12 back and look at right now. It's so funny to think about now, like, God, how many companies, there were like 300 companies that go through YC-ish about every year. And like, but it was this little corner and community of the internet i mean it still is a community a very large community now in a certain sense but i mean yeah i remember being a yc fan first and foremost and using the products like i was proud to be a dropbox user and abandon my flash drive because it was a yc company i suppose that that is even actually a bigger effect today but it felt at some point like a club. I remember, I think it was like senior year of my high school that I felt like I was in some sort of club for even
Starting point is 00:21:48 knowing what it was. Yeah, I kind of had that feeling. And then like, I eventually ended up doing YC. And I remember like, distinctly, 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, PG's house. And now like, it's just this huge and personal thing. And you only get to see like Paul Graham like once or twice a week. Like what even is this? And of course now it's like 10 times bigger than it was back then. Yeah. So catch us up there. So what, what idea did you end up going through YC with? Yeah. So in college, I ended up meeting up with like these two grad students who had this like cool idea for this new version of email. And then we tried working on it it. And it was pretty cool, actually. We got a lot of press. We got
Starting point is 00:22:28 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'd won some business plan competition. It was like $25K. So I just lived frugally on that for a year in downtown Boston. Ran out of money. And I decided I was going to move to SF and somehow like get into YC. So I worked, I got like maybe enough money for like four months of rent, moved out to SF. And I just started reading like Paul Graham's like RFS, his requests for startups that he would publish. And one of the ideas on there was like kind of related to what I'd already been doing. He had this whole thesis that like, you know, the email inbox is this like unexploited,
Starting point is 00:23:03 you know, domain and you could have a Trojan horse where you get in there with like some some sort of productivity app or something and then once you get all of the email users off gmail like you convert them to your own thing and so like that was his obsession like these like clever tricks you could use to like get a ton of people on your apps and so i was like okay let's let's just do that so i met another guy again on hacker news who i kind of posted like hey i'm looking for a co-founder okay yeah i was good i read that like you met your co-founder on Hacker News, right? Yeah. He was one of my previous competitors from my earlier email thing. And his app also wasn't doing that well. So we're like, why don't we join forces? We met in a coffee shop in San
Starting point is 00:23:33 Francisco. And I had maybe a month of money in my bank account. I don't know what I would have done. I would have just had to somehow find money or get a job immediately. But we applied together. And the process was super quick. We got in. PG asked us a few questions. We had the YC partner interview. And they're like, yeah, cool. And I was just like, okay, well, when do we get the money?
Starting point is 00:23:54 So I can pay my rent this month. Was this what, 2011-ish? We had winter 2011 for YC. So this was in the fall of 2010. Like November, December, we were applying. So this was before the Yuri Milnerner SB Angel deal where you got. That happened during our batch. That was like the like we were the very first batch for that. I remember the previous YC batch was super jealous because they only got like, you know,
Starting point is 00:24:15 like a 17K or whatever. And so that's what we got at first. It was like 17K divided by two, me and my co-founder. Like, you know, we had like enough for the two of us. We ended up moving into this rent controlled apartment and SF and just eating like a lot of like oatmeal and crackers and stuff. And then I remember like one day during YC, they kind of called us down like on a, like a Friday or like some off day, like, Hey, it's very important. Everybody come down. And we went down to the YC headquarters and they had like those telepresence
Starting point is 00:24:40 robots kind of like walking around, like sort of like a camera, like in a screen on wheels. And there's like Yuri Milonov's face on it, like this Russian oligarch billionaire, like walking around talking to everybody and like, we've got an announcement. And I was like, yeah, we're going to give everybody like $140,000 of additional money, sort of no strings attached as an investment. So that was like one of the best days of my life. I was like, okay, well, I'm going to start eating, like I'm going to upgrade to ramen now. And not have to worry about where, I'm going to start eating like I'm going to upgrade to ramen now. And not have to worry about where my rent's going to come from.
Starting point is 00:25:09 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 no it wasn't literally free money like there were strings
Starting point is 00:25:26 attached but i i think it was uncapped though it was a really good deal and none of us questioned it like we just signed we just signed the papers so at this point you're getting like probably feels like a huge amount of money in funding right like you don't have any customers right nobody's no we had literally nothing we had like a bunch of janky code that i was writing and my co-founder was going around like you know like doing some marketing stuff and trying to generate like press and like hype for like a thing we hadn't built yet so the idea we were working on was it was called task force the idea was uh you get all these tasks in your inbox you know like i've got ben and david from acquired like saying hey corlin have you prepped for the podcast yet
Starting point is 00:25:59 right and uh no you didn't really send me that email but like if you had i could have used task force to convert it into a little to-do, and it would add it to a to-do list in your inbox. And so then when I worked on that to-do, if I added a due date or I checked it off, you would get an email that said, Hey, Cortland is this far along in the to-do, or Cortland just completed it. So it was supposed to be this viral thing that would take over the inbox, and everybody would have it.
Starting point is 00:26:19 And eventually, we did launch NYC. And we got a decent number of users. By the end of YC, 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 is cool. That was kind of the mantra.
Starting point is 00:26:35 No one cared that your app had 100,000 users. That was meaningless. I'm also dying over here because after HackerFollow, my first app was a task list that I launched for iOS 3, which is like right around the same time period. And if I remember right, Gmail tasks was still this really terrible UI that could have had... I mean, you built the missing connectivity for Gmail tasks that would eventually become... I think they turned it into its own thing
Starting point is 00:27:05 but it was like constrained within gmail forever yeah i think it's still there like if you know the right combination of keyboard shortcuts like you can get a little task for you to pop up in gmail but it's not the most inspired idea like a to-do list right every entrepreneur every programmer has like a bunch of stuff they want to do when you think about solving your own problem you're like if only i could you know organize my tasks into like a little list of check boxes uh and so we did that. And it kind of sort of worked. But it wasn't like the home run that you really...
Starting point is 00:27:28 But we'll do it in Gmail. Yeah, we'll do it in email. There it was. The combination. And 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.
Starting point is 00:27:39 Maybe I should sign up. So we kind of combined those things. And we got to demo day in YC, like the very end of YC. And we like presented and investors just like, they weren't interested. They're like, yeah, you know, you've had like, okay, growth, but like, where's this really going? And we've invested in email startups in the past, and they're all dead. Like what's, what's going to make yours different? And we didn't have a good answer to that. So we went into the summer after YC with like, probably still like 120, 130k of this money in the bank, trying to
Starting point is 00:28:05 figure out like, you know, what are we going to do with this startup that's like not growing fast enough for us to raise money? Again, if we have our lower rate, one of the talks, maybe like, was it like a Tuesday dinner talk while you're on YC was Kevin Hale from Mufu? Yeah. So Kevin Hale was this, I thought he was like the coolest guy on planet earth. We had these, you know, YC dinners every week and people would come in and we had like the heroku founders came in and they just sold for like 300 million dollars and they just bought us like bought us all like the nicest steaks and you know they were dressed super suave and like it was so cool and flashy drive up in the lambo yeah yeah and like i think pg brought in like the ceo of uh yahoo at the time who was like the super extroverted guy
Starting point is 00:28:42 who like said a lot and it sounded really good but you can never quite like tell what he said afterwards you know and pg was like this is an example of a stereotypical ceo uh and uh then uh kevin howe 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 uh packed our bags we moved to florida like we're making forms but we're making forms sexy and uh we do profit sharing with our team you know we go to the beach all the time people work remote like i don't even know when they're working really and we get like 10 calls a week from vcs who want to invest and we're like now we're making millions of dollars we're cool and no one else had said that like no one was making money like i don't even know how you could make money because like
Starting point is 00:29:19 stripe wasn't even in beta at the time it wasn't so like in your cohort nobody was like talking about that one i mean there was like there was like a few companies that like had some sort of revenue model but like all the companies that were celebrated were the ones that had just like raised the most money you know who raised from a16z uh the earliest you know like there's one one founder on our batch we will not name who raised from a16z like the very first week of yc and they raised millions and they are like putting up kind of facebook growth numbers and everybody like worshiped the ground like that these founders walked on like the whole way it was obnoxious to the point was like I didn't want to see them but like you're kind of jealous too because like you know I kind of want that level of success you know but at the end of
Starting point is 00:29:54 the day like nobody was making money nobody wanted to make money no one like it was all about growth and so when I heard Kevin Hale talk about like how woofoo was just was just kind of crushing it I remember running up to PG and like hey like you like, you know, we're not growing that much. Like, what if we just did this? Like, what if we charged money? And he was like, that's cool. Like, whatever it takes to stay alive. You know, he was very much like, be the cockroach.
Starting point is 00:30:13 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 dollar unicorn because who wants to just make a few million dollars a year? It's so funny.
Starting point is 00:30:29 David always reminds me that incentives drive behavior. And if you think about YC's incentive here, do you think back on it and say, well, gosh, for their portfolio construction, they needed us to be a billion dollar company? Or at that point, would YC have been happy with a bunch of Cortland's building profitable businesses? When you interview, they really want to know that you have a shot at becoming a billion dollar business. Because that's how the mechanics, it's like the physics of the situation work. They need people to go for the gold. What ends up happening is just a lot of YC companies died. Even before our batch was over, it was kind of clear that like a few people
Starting point is 00:31:05 had given up and they weren't really going to make it. And like, especially in the summer after a batch was over, like just a lot of companies fell off the radar. I remember like talking to PGO over the summer, we signed up for office hours and went in and he was just like happy. We were like alive and still working. He was like, Oh yeah, we don't even know what happens to a lot of these companies after a certain amount of time. So like, we're happy that you're here. And I think after that, it's less, they're less like adamant that, okay, you got to go for a billion. You got to go for a billion. You got to be a unicorn. They're like, do whatever it takes to survive and get to the next stage. I think in a lot of respects, like that's kind of like the
Starting point is 00:31:34 hallmark of being a good entrepreneur. Like how can you take like one, you know, small success and parlay that into something bigger. And eventually maybe you get another shot at going for the unicorn company. So I think in the beginning, they were very focused on us being big. There's all sorts of questions about how this gets big, which are easy to answer because it was like PG's idea that we were working on. But later on, I was like, how do you not die? Yeah, it reminds me, he's got that one essay. I think it might be in Startups Equals Growth about the hill climbing algorithm.
Starting point is 00:31:59 And you basically always try and find the next highest hill. And you would think that you could accidentally find a local maximum and not the global maximum that way. But in practice, whenever you're on a higher hill, that's a better way to get to the next hill. And you can sort of always use that way to find your way to the absolute maximum. It's a little ethereal, but do you sort of agree with that? No, I completely agree. I think if you're creative enough and you think about it enough, you could figure out a way to your next hill. Like, IndieHackers today is, to my knowledge, the biggest online community of startup founders. IndieHackers in its first month was a blog. There's a lot of blogs out there. We started off with a very tiny hill. And I made the blog as big
Starting point is 00:32:37 as I think I wanted to. And maybe it could have been bigger, but it was pretty big. But there's always some way where you can say, now I have this advantage that I didn't have last week or last month or last year. Like what ways can I use this advantage to like, you know, parachute over to that like slightly bigger hill. And maybe you like lose a little altitude on your way there, but then you're on this bigger hill and it's much easier. Uh, the analogy I like to use, maybe not hills, it's like a staircase, right? Like a lot of people want to like jump to the top of a staircase, right? And it's very hard to jump to the top of a staircase. Like very few people are capable of
Starting point is 00:33:04 that feat, but it's pretty easy to walk up a staircase one step at a time. And so I think a lot of being a founder is just figuring out how you can go one step at a time, even if you have some grand ambition, how you can start super small and then 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 in online communities sort of starts with meeting your co-founders on Hacker News and being an obsessed participant with that. And like you said, today you run, how do you describe it? The largest online community of...
Starting point is 00:33:35 Startup founders. Startup founders. That's cool. I 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 like, oh, wow, like, you know, I'm making some side income. And then a few months later, like, oh, wow, like I can quit my job.
Starting point is 00:33:51 And then at some point, like you're making a lot of money and you're thinking, okay, well, like, what do I want to do? Do I want to retire to a beach somewhere? Or maybe like what I want to do is build something even bigger. So a lot of indie hackers I talked to are like are no longer even indie hackers.
Starting point is 00:34:02 They've raised money. They're building bigger companies. And that's like where their life path took them. Well well that's what i think is so cool about this like unless you would disagree you're the authority but i don't think being an indie hacker means like you don't want to raise money or you don't want to build something big right it's like you want to build something that people want and the customers will pay you for and go from there and sometimes those become become notion, right? Or like, and sometimes they become indie hackers. And sometimes they become just a business that makes you a couple hundred thousand a year. Yeah, exactly. Like, I don't like to juxtapose indie hackers, like as a, as a counter
Starting point is 00:34:38 argument to like raising money so much as it is a counter argument to like having a boss and working like a desk job and wondering what if for the rest of your life you know being an indie hacker is really about the idea that like you can achieve your own sort of freedom whatever that means to you maybe that's financial freedom maybe that's creative freedom so you can work on whatever you want maybe that's like time freedom so you can work whatever hours and schedule you want and so being an indie hacker is really this like this confidence in yourself like hey you can create something that that'll make your life better really and make other people's lives better in the process and give you that freedom. And maybe that looks like raising a ton of money in the future.
Starting point is 00:35:09 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 on a path. You're on a very specific path. If you say, I'm going to build something profitable that funds itself, you got all the option value in the world to continue to take it whatever sort of trajectory you want to. Yeah, exactly. And the kinds of companies that I've seen people build, I almost feel like we need a new word. Because you think about business, it has all these connotations. You imagine a bunch of men in suits in a boardroom or something,
Starting point is 00:35:42 reading graphs. And then the word startup is like not quite right it's closer because you think about tech and technology and it's like internet enabled they're wearing t-shirts instead of seats yeah yeah but they're doing the same yeah exactly like there needs to be like some like i don't know what it would be like some third word where i'm just like looking at people like i interviewed this founder sam eaton on the podcast earlier podcast earlier this year. And his sister at some point was like, I want to sell cookies. And he's this software engineer who's working growth roles at Airbnb. And he just got a job offer at Google. And he's like, no, we're not just going to sell cookies. We're going to have a cookie company.
Starting point is 00:36:16 And we're going to be tech-enabled. And we're going to have an app and all sorts, like our own fleet of delivery drivers. And he's just in heaven sitting around coding his own apps. They don't use Uber Eats or Door door dash 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 margins too so like they're living a really good life and it's like it's not just like your traditional idea of a business you know he's like trying to like make his community better he's trying to make his life better.
Starting point is 00:36:45 And he's not stressing over like how fast can we grow and how much bigger can we make this? He's thinking about, you know, like what do I like to spend my time doing? While at the same time, he's like kind of getting rich and making everybody feel great. I think this is like such a big movement alongside, you know, the traditional startup race venture capital,
Starting point is 00:37:04 like be something big right off the bat because like the economic you know generation activity generated by this class of entrepreneurs is probably in aggregate going to be equal if not larger than like the rockefellers of the world did you guys watch that series chernobyl i was on hbo last year oh it was so good great series oh no i heard about it it was good freaky they like timed it so like right after game of thrones went off the air they're like boom here's another series don't don't unsubscribe from hbo but uh the uh they kind of boiled down the entire story like the work of like this one scientist and it was like an amazing story it was great but like obviously in real life
Starting point is 00:37:41 it was probably dozens or hundreds of scientists and engineers working together to try to figure out how to contain this nuclear disaster. And like, the reason why they did that is because it's just easier to tell a story about like one person. And it's the same in business. Like, it's easier to tell the story of like one company. We're all fascinated by like how big Apple is and the impact that Apple has. Or like, you know, McDonald's is crazy.
Starting point is 00:38:00 Like they have 20,000 restaurants in the United States. Because that's like the easy story 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. And 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. And I think the way I look at what I'm doing with IndieHackers is I'm trying to connect the dots of all these really tiny tech businesses that are never going to make the news. You know, they're not, you know, Amazon, they don't have a $2 trillion market cap. But like, what happens when like a million people
Starting point is 00:38:32 are building businesses and make millions of dollars online? You know, what does that look like? When this comes out, we will likely have just done the DoorDash and the Airbnb IPO episodes. There is a narrow set of practitioners, whether you're a founder or an employee, who can learn from the tactics and the playbooks accomplished with DoorDash and Airbnb. But based on all the media coverage, those are the stories that get told because that's the simplest and most interesting narrative. But if you're looking to actually learn, let's say IndieHackers continues to grow and
Starting point is 00:39:06 expand and you figure out more ways to parallelize it. And at some point, there's, you know, 100,000 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 a lot of the things that I'm building on IndieHackers. How do you see these companies very early days? And then how do you filter
Starting point is 00:39:39 down to a very specific niche so you find the company that most matches the profile of what you're trying to build and so we have like this directory that i kind of half-agilely built like two and a half years ago and i was like oh we should have a directory of products then i haven't touched the code like two and a half years but like when i built it it was like okay we had like 50 people on it and i checked the other day and it's like 12 000 products on there and they all have like a little timeline where they're like saying okay here's where i launched and here's what i thought about my launch and i thought i was being ridiculous saying a hundred thousand, but it shouldn't be
Starting point is 00:40:06 long. No, it shouldn't be long. You know? And I think it's just the resource that needs to exist. Like you need to be able to go out and see how other people are doing it because that gives you, I think the confidence to go do it yourself. When you see that someone who's like not that different from you, like kind of put their playbook online. I'm going to do David's job here. So take us from the light bulb of Task Force should be making money to the founding of IndieHackers. 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,
Starting point is 00:40:39 hey, you want to make money with your product? Go for it. Were they in your batch or were they... They were before you, right? They were before I was, like maybe by a year or two they took a while before they got their product to the point where it was ready understandably because there's like a lot of regulation dealing with banks and stuff but uh 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 like a day or two, just like over a weekend. And the next weekend, I think we made like $3,000 in payments, charging people like five bucks a month for like this crappy to-do list
Starting point is 00:41:10 Chrome extension. Like I thought we were going to make like a hundred dollars or something. And I was like, holy shit, like we can like kind of pay our rent, you know, like we can pay for stuff with this. And so of course we went to the YC partners were like, Hey, look at this. This is cool. Like we're making a few thousand dollars. And they're like, yeah, but what if you were making like way more and you had a different idea that wasn't a tiny Chrome extension, which in some ways is good and bad. In hindsight, if we had stuck with what we were doing, we could have probably grown it to a much more substantial size and iterated. Instead, what we did was we like did what you should never do.
Starting point is 00:41:37 We just completely started over from scratch with an idea that we thought was like bigger and better. And we sort of violated that principle of like taking it one step at a time. And so probably over like the next six or seven years, I started five or six different companies. Each one 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. And I think this is an important thing that I realized. The first couple years, I was just peddled to the metal on my computer
Starting point is 00:42:05 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. And it never did. And not only did I not succeed, but I also just wasted a bunch of time not living a very fun and productive life. I don't even remember one or two of those years in my life because I was 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 thought of it then was that everybody's kind of got like a certain number of companies that you need to start before you succeed. For some people who are exceptionally talented or lucky or both, like that's just one. They're going to succeed right out of the gate.
Starting point is 00:42:40 Some people, maybe it's like 35. For me, it was like like seven and really all you need to do is just to make sure that you like you don't quit before you get to that number like that's really the entire name of the game like just don't quit before you get to the number where you succeed and so you should just structure your life to make it so it's easy for you not to quit and to make it so that like the journey itself is like actually pretty fun and you're learning a lot along the way because like you're not just building a startup in a vacuum like you're meeting people and you're picking up new skills and you're learning new things and like like the startup is kind of like the journey is as important as like the destination at the end of the day and so nowadays and like eventually i kind of figured it out like oh i'm
Starting point is 00:43:17 like learning so much stuff like i should make sure that i'm really enjoying my life while i'm building stuff so the last few years there before i ended up starting indie hackers are actually really pleasant and i feel like i kind of leveled up as a person while i was building stuff. So the last few years there before I ended up starting IndieHackers were actually really pleasant. And I feel like I kind of leveled up as a person while I was building my startups instead of just sort of like, you know, worrying every step of the way, like, am I there yet? You know, is it going to work?
Starting point is 00:43:33 Is this going to be the one? Hmm. That's such a great lesson. And just like a couple of points of clarification, were these all inside the same like entity or was it different co-founders or how did that sort of technically play out? Yeah. Like the first one or two were kind of inside the same entity. And then my co-founder and I split up and we kind of just declared our YC startup dead. Like this is,
Starting point is 00:43:55 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. Part of it was like, I just didn't like the idea of having a boss. Like me working at Stripe today is the first full time job that I've ever had. Like, I just don't like to be told what to do, I guess. And part of it was like this, like, I don't know this pride of like, I don't want to have to interview somewhere like I don't want somebody to be able to reject me like I want to be unrejectable like i don't want to ever put myself in a position where
Starting point is 00:44:26 somebody could say no and so like okay i just want to keep doing this myself so i would just like survive off of kind of my income from some of these apps because i would keep them running and they would make like a few hundred dollars a month or a few thousand dollars a month and then when i got low on income i would just go get a contract job and then like work on the side etc etc and just kind of like make it so i never had to quit, you know? And I think there's a lot said about startup failure. Like, okay, maybe your, maybe your ideas fail because like the market was too small or because, you know, your product took too long to develop or you ran out of money. But my, my take on it is kind of that none of those things actually kill your company, you know, like those are just
Starting point is 00:45:01 obstacles, right? Like, so your market wasn't big enough and then what right like you quit like you didn't have to quit right you could have like that's kind of like if you imagine like a startup journey like being like you walking from like you being an early pioneer walking from the east coast to california right like those are just like obstacles there's like rivers and mountains and like you can kind of like step over those or go around them or you can just be like fuck it i'm just gonna like stop here and just live in kansas you know and like you don't want to stop and just live in kansas like you want to keep going and find a way to keep going and so for me that was just living super frugally and figuring out a way to like start the next thing which meant taking on contract work and building up my savings whenever i needed to yeah default alive or uh at one point
Starting point is 00:45:38 i ran a startup weekend in seattle and bo lu who actually i think went on to yc with this company future advisor and uh and sequoia funded it um He gave this great talk called, You're Alive As Long As You're Not Dead. And he was like, yeah, lots of 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 in 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,
Starting point is 00:46:06 like I've quit lots of different companies, but like as long as you don't quit your overall journey, like you're still on that path, you know, you're still headed to California and you're like, you're going to eventually get there. Who knows how many startups it's going to take, but you'll get there as long as you're sort of learning and you persist. So I think the most important thing you can do is figure out how to keep going.
Starting point is 00:46:20 All right. So the genesis of IndieHackers. The genesis. How did that happen? So I just rolled off a contract job and I had about a year of runway in the bank. So I was like, okay, here we go. Like take four, I'm going to, I'm going to figure out like something to work on that's going to work this time. And you know, worst case scenario, it's going to all fail. And I'm going to go back to working contract jobs. Uh, and so I started working on this one app that I called Knox and it was kind of like this ment clone for your phone that would like buzz you with your finances and like maybe like two or
Starting point is 00:46:49 three months into it i was like this is an endless slog of 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 in hacker news of people who would come up with new ideas and we're already making like five or ten grand a month and like i hadn't even launched my thing yet so i was like okay this is like a dud. I should scrap this and go back to sort of the drawing board and figure out, you know, what can I like, what are all the different lessons that I've learned after years of doing this? Like, let me make sure like I'm systematic in how I approach this. So I'm not just kind of making
Starting point is 00:47:19 the same mistakes again, because I had repeatedly made this mistake that a lot of software engineers make where we just, you know just spend way too much time coding. And I think the biggest lesson at the top of the list was, only work on things that you can build in a few weeks. I went from idea to basically launch with IndieHackers in exactly three weeks. And it didn't require very much code at all. It didn't require a lot of marketing or anything. It was just super, super easy.
Starting point is 00:47:43 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 like, oh, how do I get more time? Maybe I'm going to work nights and weekends and all this stuff. And I'm going to work a three-day workweek instead of five-day workweek. But I think the third lever that's probably the best is like, how do you just start smaller? 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
Starting point is 00:48:12 indie hacker business so I can sort of, you know, pay my rent, pay my bills, and then figure out what I want to do next. A ton of other people clearly want to do this. Like I see them on Hacker News every day asking all these questions to people who've done it and sharing their stories. Maybe what I can do in a very meta sort of way is build a better version of these Hacker News discussions. People are always talking about this, but their stories kind of suck. They're leaving out important details. And everybody in the comments is asking them, well, how'd you come up 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
Starting point is 00:48:44 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. So that was my idea. It's phase one. 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 get their information, put it on a blog and launch it. And I'm 100% sure people
Starting point is 00:49:12 on 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 gonna love it but 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 like i'm gonna start in this really small pool you know i'm gonna build 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 like maybe i'll have an audience maybe i'll have a lot of traffic, maybe I'll have a big mailing list. And then from there,
Starting point is 00:49:46 it should be easier for me to figure out how to make an actual business. The revenue aspect, maybe revenue and profit aspect of the stories you were telling, was that super key? Like, cause I can imagine like, you know, when you're trying to find like, oh yeah, you're talking all this game about like how great it is, all the stuff you did, but like, is it actually working? Like, you know, give me like, like that feels like almost like the like the Zestimate before Zillow, right? Like, you know, it's like, hey, this house looks good, but like, what's it worth?
Starting point is 00:50:16 Like, you know, how important was that? Extremely important. Like if I could write a startup book, I would call it problems first, where like the first thing you want to do is you want to figure out like, what are the problems that your potential customers have? So you don't build like some random product that like doesn't solve their pain points. And when I was like reading all these comments on Hacker News, like I was trying to find a business idea. And I didn't want to read comments from people who like didn't have proof that their business idea worked. You know, somebody said like, Oh, I've got this great company, I'm working on it,
Starting point is 00:50:42 it's really great, you know, does this and this and this. And like, they don't share the revenue numbers. Like for all I know, they're making like $5 a month, you know, and it's not that great. And I could tell everybody else in the comments, like had kind of the same problem. They're like, hey, we only want to upvote the stories that share their revenue numbers. We only want to upvote the stories that have like some sort of proof or some sort of like inspirational thing that we can like grasp onto to know this person is legit. Anybody can give you advice and tell you what to do. But if there's no like outcome, that's a result of that advice. You don't know if it's good. And so train your model on garbage data. Exactly. And so like, that's a thing where like, there were a lot of
Starting point is 00:51:11 other interview sites on the web that talk to entrepreneurs. There are pretty much none at the time that realized how important it was that you needed to be transparent, like you needed to include revenue numbers. And so when I went out and I started emailing people and saying like, Hey, you know, my name is Coraline. I'm starting this website. It's going to be called Andy Hackers. Will you tell me your company story? And oh, by the way, I need all your revenue numbers. Half of them were just like, fuck off. You're nobody. Why would I give you my revenue numbers? And then half of them didn't respond. And 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
Starting point is 00:51:48 10 people to agree to share their entire story and their revenue numbers. When you launched, you built the site, right? So you didn't go to Squarespace, you didn't go to Webflow. What was the thinking behind that? Yeah. So I had a couple reasons for for that part of it was i had a bunch of other ideas that i had come up with and my brainstorming and any hackers kind of scored the highest on my rubric because it was so quick to build but i felt really bad because like here i am the software developer like from building all these other startups like i learned so much stuff from building startups over the years and like failing time and time again like i learned
Starting point is 00:52:21 how to design i learned how to do front- development and backend and like server admin stuff. And here I was like going to sort of blog. So I was like, wow, it's such a waste. Like I want like to throw myself some kind of bone to make this fun. Because starting a company should be fun. Like you should enjoy the journey, not just the destination. And so I said, okay, well, I'll do a blog, but I'll allow myself to just build like my custom blog from scratch, even though that's going to add like another week and a half to my launch time or whatever. Like I'll allow myself just that little bit of fun. And then part of it was kind of a branding and strategy play. So you weren't yet thinking like Stripe Revenue Connect,
Starting point is 00:52:54 like, you know, building a community. That was like kind of in the back of my mind, the community stuff, definitely not like the product directory and Stripe Revenue stats or like a lot of the stuff that exists today. But like I did have kind of a strategic sort of session with myself so i spent like one day just thinking strategy like because in the beginning of your company there's a bunch
Starting point is 00:53:11 of decisions that you make that are much harder to undo later on like you'll tell yourself like oh i'll use a crappy design now and redesign it later but like really that's a lot of work and you have a lot of more urgent things and you say oh i'll have a crappy name now and have a better name later but like really like it's hard to change your name later on so i've been bitten by like all these issues and so i said okay i'm gonna take one day and make all of these like semi-permanent decisions like what do i want the color scheme to be how do i want the site to work what i want it to be called and kind of the three decisions that i came to were number one i want the site to be named after kind of a new class of people because i was like well there's no name for like these
Starting point is 00:53:44 people and these and these discussions it's like really hard for them to find each other even because like there's like what do you even search for like story of person who bootstrapped startup and makes five thousand like there's nothing to search for so hard to find so it's like i'm gonna call it indie hackers i had a bunch of like worse names but any hackers are the best one i came up with i decided i wanted to make make the site blue. So it's this very dark blue color that's probably not very accessible and kind of hard to read. But every other site in existence is just white with black text. Everybody was writing on Medium. It all looked the same. And so I wanted mine to stand out so that if you ever read two IndieHacker stories,
Starting point is 00:54:17 you would instantly remember that you'd been to this website before. And then I wanted to do it custom because I just didn't want to build on somebody else's platform. I didn't like the platform risk. I've been kind of burned by that before building on Gmail and you know, they would change their API all the time and like kind of break our apps. And so I didn't want to deal with like, you know, putting up a blog on medium and having it look like every other medium blog and then medium changes their business model or something. And now I'm screwed. So those are kind of like the three decisions I made back then. And all of them, I think turned out to be pretty good in the long run.
Starting point is 00:54:47 And the etymology of the name, it's interesting thinking about when you started this, the notion of an indie developer was already a thing. I mean, I remember considering myself an indie developer in 2008 when I started working on my first iPhone app. And I think Craig Hockenberry and a bunch of the like Icon Factory people, they were saying, oh, I'm an indie you know iphone or apple developer and obviously hacker news was sort of like a a thing but those communities were basically non-overlapping like hackers were what people who were technical and wanted to start high growth technology startups refer to themselves as but indies were what the like lifestyle developer community primarily centered around apple platforms kind of called themselves yeah and i wasn't thinking about like honestly any of that indie stuff like it
Starting point is 00:55:30 wasn't even i wasn't even aware that they were like indie developers i was just like okay well like i want like the idea of like an independent programmer because again it wasn't so much a rebellion against raising money it was a rebellion against you know going to work for the man and like you know making google 10 million dollars a year from your code, but you're only getting like 200K of that. Why don't you start your own thing and be kind of your own indie developer? And Hacker News was so-called because hackers are just another word for programmers. So the idea is like, okay, you're a programmer, but you're independent. There's no cap on your salary. There's really no limits. You can do whatever you want.
Starting point is 00:56:02 Yeah. And before we move on from this point, talk to me about platform risk. Because in my mind, you know, we think about this for acquired to we're always trying to get the most direct relationship possible with our listeners with our LPs with our you know, with everybody. And there's always some platform risk, like we've collected email addresses from one out of I don't know, six or seven listeners, you know, from all the various reasons that people join our slack 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
Starting point is 00:56:43 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 of 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 it 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, etc. Maybe you can charge a high amount of revenue per user, but that means you're going to get
Starting point is 00:57:12 maybe fewer users in the door, fewer customers. But then also, you can spend more to require your customers. It's all trade-offs. And so for my particular situation, when I looked at that trade-off, really 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 are 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 hit and miss. And they would also just completely
Starting point is 00:57:42 destroy my ability to have any sort of branding. i knew that kind of step two in this playbook might be to build a mailing list or a community like i wasn't sure but i knew that like if i was going to name it indie hackers like go for something where the brand actually mattered which i think is important if you're going to have something where it's kind of like free and i was just getting like lots of users in the door but i didn't have a business model that i wanted to own my brand and so it wasn't worth it for me to use any of these platforms even though they would help with distribution, if I could instead just like do my own. And I also had like kind of my own distribution strategy. I already knew that people were going to be eating this kind of stuff up on Hacker News because they already were. And I already knew that
Starting point is 00:58:16 Hacker News had like a lot of traffic. So it's like, okay, I don't need Medium. I can do it on my own. So I get like no real benefit from Medium and I get all this additional risk. Like the trade-off just wasn't worth it.'s kind of funny i mean in some ways you maybe ran the uh uh the airbnb playbook of um expulterate craigslist yeah you did for this segment of hacker news my buddy uh greg eisenberg has this whole idea of like you know i'm bundling craigslist i'm bundling reddit i'm bundling hacker news it's a huge community there's all sorts of sub like discussions happening in there that happen regularly totally there's a it's a pretty big tent exactly so you but you build the site it wants to blog on your site as i understand it
Starting point is 00:58:55 pretty quickly you figured out that email was a pretty big unlock kind of on both like for the interviews you were doing call it the supply side of these stories and for readers for the demand side totally you can almost imagine the web is like a collection of like feeds or like destinations and some of them are places where people go like habitually like i habitually check my email i habitually check the notifications on my phone i habitually check twitter i'm just like addicted like i'll sit down and just like press t on my keyboard and like black out for a second like i'm on twitter and then there's other places where like people just don't have a habit like i made indie hackers no one on earth had a habit of regularly visiting indie hackers and they weren't going to have that habit anytime soon
Starting point is 00:59:39 because i was publishing like once or twice a week you know like twitter's got new content every single minute so uh for me it was like okay well how do I hook into like one of these feeds that everybody already habitually looks at? And it was a combination of both Twitter and email. So I made like the Twitter indie hackers account. I tried to tweet every story that I had so that you would sort of incidentally run into them when you check your Twitter and be like, oh yeah, I remember indie hackers. Let me go back there. And then email was a huge one because like I actually own the email addresses when people sign up. I can take that with me anywhere. 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
Starting point is 01:00:13 of every interview, just trying to get people's emails. And I think in the first week, we got like 1,000 or 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 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 and like i'm a developer i could do that too and so they would immediately get on an email because like they want more of these like stories you know they want more um glances like what's possible so that like and when the day comes that they're ready to start their startup like they haven't forgotten where to go to see those examples you gotta have
Starting point is 01:00:48 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?
Starting point is 01:01:15 Like, I don't know, but I'm pretty sure we've gotten a lot. We got at the top of an accidental feed. Yeah. Yeah. It's a hard one lesson for a lot of people who are starting startups. Like if you're an indie hacker, you don't it's a hard one lesson for a lot of people who are starting startups like if you're an indie hacker you don't have like a bunch of investors and
Starting point is 01:01:28 mentors like you probably just kind of by default believe like you know if they build it if i build it they will come you know i'll just build some cool stuff and get a bunch of people like in the door but it turns out that like building stuff is kind of easy even like even if you're not a developer today like you can stitch stuff like i talked to a guy yesterday who built like a whole slack bot without using code at all it doesn't even know how to code and uh the hard part is like getting people to actually care about what you're building and actually find it so that means like you have to actually solve what it's like and you run into it yes and run into it and run and it's not just run into it once it's like run into it like repeatedly and like that's very hard to do but if you think about it like really carefully before you start
Starting point is 01:02:04 then often like you can come up with something like 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 IndieHackers. I was already in Hacker News, and it took days of me reading these threads before it clicked. Like, 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. Okay. 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.
Starting point is 01:02:35 Now let's shift to the indie hacker conversation. How did you start making money? Yeah. So actually what happened is my very first 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
Starting point is 01:03:15 dump it out, you know. So like this company like offering me hundreds of dollars like it was like a wake up call like, oh, I can like make money from sponsors. But I was also like super focused on growth because I was thinking, OK, well, I've got like from sponsors. But I was also super focused on growth because I was thinking, okay, well, I've got maybe six months of runway and I've got six months of savings in my bank account. I've got time. Why don't I just grow the site even bigger? Because there's only one of me. I don't have that much time to try to sell ads and build a site and do all these interviews I'm doing every single week. I'm just going to grow it, not worry about money, and I'll worry about it later. So I did that for three months. I just kept going to grow it, not worry about money. And I'll worry about it later. So I did that for like three months. I just kept trying to grow the site. I didn't figure out how
Starting point is 01:03:47 to grow the site at all. I did like never found something that was bigger and better than getting on the front page of Hacker News, go figure. And so by December, I launched in August. By December, I was like, okay, screw this. I'm going to start trying to make money. And so I started like basically emailing my list, which at that point had probably been grown to like 10 or 15,000 people and saying, hey, like, you know, here's the email with the new, like this week's interviews. But also by the way, here's an empty ad slot. Like your company could be here. And I was very lucky that it's the billboard that you see with the, like your ad could be exactly that, but an email form. And I put that on the website too. And like, it turns out when you have a company
Starting point is 01:04:21 that targets people who are starting companies, you have a lot of potential advertisers on your mailing list who all want to basically advertise with you. And it also turned out, which I didn't realize at the time, that indie hackers were some of the worst possible customers to buy ads. Because these are very fledgling startups. These are people who decided to start something because they read about it on indie hackers two months ago. And if they were going to spend like $500,000 on an ad, like that ad had better work. Like that's not, that's like their whole yearly ad budget. And so I...
Starting point is 01:04:50 It's almost like you would want a company that is selling tools to people. Almost like that. So I went through like a lot of these awkward conversations where I'd run ads for people. Like I just wanted to do right by them, but like the ads didn't always get enough clicks. And sometimes like I would refund people. And it was just like very stressful. I didn't like doing it. And so I created kind of like a dream list of companies. Like, okay, which companies actually
Starting point is 01:05:10 have a lot of money that would be good sponsors? Like I've no, I've no experience doing sales, but like I'm going to have to figure out how to do this. And I had the very bottom of my list, like my number one dream company who should be sponsoring indie hackers was Stripe. I'm like, okay, I'll eventually get to them. But like, I like figure i'm like i want my shit to be good some warm-ups in first yeah i need some warm-ups you know and so i don't warm up on broadway exactly you don't want to like embarrass yourself in front of everybody so i got some warm-ups i sent a lot of cold emails i found like the heads of marketing on linkedin my buddy jeff who ran a podcast i was on gave me kind of his list of leads for who was advertising on his podcast.
Starting point is 01:05:49 And 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 are broke. Yeah. And not to mention, one 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. And I think that applies to even coming up with startup ideas and trying to figure out
Starting point is 01:06:30 a business model. It's kind of counterintuitive. People repeat this mantra, solve an unsolved problem. And it's almost like you want to do the opposite. You want to look at problems that people are already paying a lot of money to have solved and insert yourself there. My friend started a company called Key Values. She's like been one of my best friends for years. Her name is Lynn. And like her company helps startups hire engineers. And you know what? Like startups are hiring engineers just fine, like well before her company came along. But like we kind of picked that idea because we looked at like where a company is spending money, you know, like where they spend a lot of their money. And
Starting point is 01:07:01 it turned out like hiring engineers, hiring recruiters was like a huge, huge cost center for companies. And like they were just willing to spend a lot of money money? And it turned out hiring engineers, hiring recruiters was a huge, huge cost center for companies. And they were just willing to spend a lot of money on it. And within a year of starting her company, she grew her revenue to $100,000 a quarter. She was living a great life. She made it look easy, her first time out of the gate, in part because she picked a problem where people had budgets. Right.
Starting point is 01:07:21 And I think the insight here is if you really want to overly simplify the sales process, there's educate and then win. Like educate people that their need is real. And then once they're convinced that they want to solve this problem, then go win and be the way that you solve that problem for them. And if you're selling into people with budgets, you don't really need to educate because they're totally bought in on solving that problem already. Yeah. And education is hard and it's risky because you might educate somebody and then lose because someone else comes along and wins yeah or more frequently you educate somebody and they're like yeah right yeah i don't know i've got these other things that like i need to solve all right so broadway comes then you get a particular email yeah so i don't know i'm selling ads for like a few months. I'm just
Starting point is 01:08:05 happy to be honest. Cause I got to the point, I think in February, 2016, where like any hackers are going to pay all of my bills. And I was like, wow, like, and less than a year I've gone from like, you know, nothing to finally like one of the ideas I've done works, you know? So I'm like, so no, none of the other companies you'd worked on, you'd gotten to this point where it's like, revenue is covering my personal. And it was better in like literally every single way. Like I eventually, like I had added a community and so people were sort of talking to each other. So I began to see kind of a path where like, Oh, I can do less work. Like maybe people can interview each other. And like, I don't have to do anything. People really liked it. You know, it was like a very, like I
Starting point is 01:08:37 wasn't making to-do list software where like all I got were like angry customer emails. Cause I don't have the right feature. Like every email I got was something positive. people talking about how inspired they were by an interview that they heard like it was just like a hundred percent good for my life in every single way so i was just like blown away and super happy and just high on life and then to make things even better i get this email out of the blue and so like i hadn't gotten to stripe yet on my my sort of like list of sponsors to reach out to us maybe halfway down you weren't in the same batch like you didn't know that no like i think during the stripe beta i'd like maybe like gone in there like a little stripe chat room and like you know pointed out some bugs and ask some questions but like i never
Starting point is 01:09:11 really talked to the founders outside of that uh and the email like i just stepped off a plane actually i was going to a buddy's bachelor party in mexico and so i stepped off the plane i was checking my emails and like the very top of the inbox was like acquire indie hackers question mark from like patrick at stripe and i was just like holy shit there's like there's no way this email's real like this is completely you're getting trolled i'm definitely getting trolled but i read it and it was real and he was just kind of like hey courtland like really like admiring what you're doing at indie hackers you know is there any way you'd be open to stripe you know potentially acquiring it and so the first thing i did was like i forwarded to my mom
Starting point is 01:09:44 sent to my brother sent to my friends it's It's the Paul Graham email all over again. Yeah. Yeah. It was like the coolest thing ever. And we ended up meeting and talking and kind of feeling each other out, uh, at brunch the next Saturday. And, uh, over the course of a month, like worked out kind of a deal. And I joined Stripe in April, 2017. All right, listeners, our next sponsor is a new friend of the show, Huntress. Huntress is one of the fastest growing and most loved cybersecurity companies today. It's purpose built for small to mid-sized businesses
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Starting point is 01:12:02 24-7 team of experts who monitor, investigate, and respond to threats with unmatched precision, head on over to huntress.com slash acquired or click the link in the show notes. Our huge thanks to Huntress. Lots to unpack here. Before we get too far into it, I want to understand, let's relate it to our previous conversation on educating and then winning. Had Stripe and or Patrick decided that they wanted to own an asset that was sort of a community of people talking about building stuff on the internet that very likely would need Stripe to monetize and then you were the pick? Or was it like, hey, wow, that guy's really got something cool?
Starting point is 01:12:41 I think it's a combination of both. It's been funny looking at just acquisitions over the years 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 the Crazy Ideas List. And it's like, hey, everybody, write down the craziest ideas. If it's a reasonable idea, it's not allowed on this list.
Starting point is 01:13:12 You need to write down just crazy things that we could potentially do that might win big. I think some version of indie hackers have 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 like a lot of uh business from early startups like these startups grow you know they might be making a thousand dollars a month now but like five years from now they could be lift and so like winning like the hearts and minds of early stage startups matters a lot and so that idea was on there and they just like never did it right because there's like maybe a thousand ideas on that list and then then I started Andy Hackers. It just worked. It worked really well. And it just happened to very luckily, perfectly align
Starting point is 01:13:48 with what they wanted to do. Or it's like, okay, well, it's empowering people to get started and inspiring them. And Stripe is a company that cares a lot about its reputation. It's not an accident that Stripe hasn't had any sort of major scandals like almost every other huge unicorn company. It's because the founders care a lot. And we have a lot of good will among founders and developers and make a lot of decisions at the company that have that in mind, to do best by people. And so, NDHackers was also a huge check in that direction, where people just really liked NDHackers. They liked the positivity, they liked the optimism. It was all about how you can do it, how you can stick it to the man, start your own business. It was very empowering.
Starting point is 01:14:27 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 that clearly wants more businesses to exist and more businesses to succeed. And what were some of your concerns once you started after you got out of the initial wave of Oh, my God, then you're like, Wow, what would I sell this? Should I sell this? Like, how did you think about some of the trade offs intentions there?
Starting point is 01:14:54 Yeah, so a lot of my concern at the time, like one of the things I was weighing heaviest on my mind was like, I just really didn't like selling ads. I was really not having a great time. I mean, I was making money, it was like fun, fun to get checks, but like, I wanted to make indie hackers bigger and better. I wanted to spend a lot more time coding the community. Like at that time, the community only had like, maybe like 40, 50 conversations a week. Now it's got like tens of thousands. And I just wanted the time to do that. And so I was thinking, okay, well, like if I go to Stripe, like, what are they going to have me working on? You know, how much say are they going to have and what I'm doing and like, how much does their vision align with what my vision is for the
Starting point is 01:15:26 company and if it's off by even like a small amount like maybe that's not a big deal today but like four or five years from now like that could be a huge deal like a small gap can turn into a really big gap and so i really wanted to know like okay are we going to be aligned i wanted to know because that's kind of like for the like the betterment of the community like the people at indie hackers like is this going to be good for them you know if you have a community and you have something where like all your users are quite vocal, especially if they come from Hacker News,
Starting point is 01:15:48 which most IndieHackers did, these are opinionated people. These are opinionated people and they don't like tend to look kindly on acquisitions that go wrong and watching their favorite products die. So I wanted to know, okay, like is IndieHackers going to be better off for this?
Starting point is 01:16:01 I wanted to know if I was going to be better off from this, you know, how much money is this acquisition going to like make me, right like uh how does it compare the whole point of indie hackers right is like exactly yeah this is gonna like i'm gonna no longer be sort of like technically indie you know like what is the trade-off i'm making and like how indie will i be i have this whole point that i make to to friends and like they it always gets like a mixed reception but like i think everybody's kind of a business even if you're an employee you should think of yourself as a business anytime money changes hands
Starting point is 01:16:28 you should think of yourself as a business uh if you want to learn how to improve your career like read a business book and think about yourself as a business and so you know as an employee like yeah you might seem like you you have no power but like i learned from contracting like you have a lot of power if you can make like the value or the service or product you provide to your employer really unique like it's harder to fire you and it's like you're more valuable you can get paid more you can get paid what you're worth rather than being or the service or product you provide to your employer really unique, like it's harder to fire you. And it's like, you're more valuable. You can get paid more. You can get paid what you're worth rather than being paid like very little because you
Starting point is 01:16:49 have so many competitors of the exact same job title as you. And like, you know, so many other parts of like the employee experience relate to being a business. You know, like everybody has marketing experience. If you've ever made a resume, like that's basically an ad. And when you've like shipped it out to, you know, potential employers, like that's like basically marketing. And if you've done an interview, like you've like shipped it out to you know potential employers like that's like basically marketing and if you've done an interview like you've done sales because you're trying to sell yourself so i thought about myself in that light like okay well how much
Starting point is 01:17:11 freedom and independence am i going to have as an employee of stripe like who am i going to report to you know what are they going to be telling me to do if anything and i got to imagine even though this idea was on the stripe crazy ideas list for a long time probably the reason nobody ever did it is like you got to focus on like do it you can't be like pulled in like oh yeah like i know you're doing this thing right but like hey we've got this bug like can you just like jump in and like fix it or like you know we got to do this thing like you know you can get back to doing that thing but you got to do this thing like you know it's also completely different and it's also like a completely different type thing like the average sort of engineer like a bigger startup is not like someone with a lot of startup experience. You know,
Starting point is 01:17:46 there isn't like a roadmap for like, here's how you start a large community of founders. You know, there's no like step-by-step process. Like it hasn't really been done before for some reason, like there just aren't large communities of founders that have like really thrived online. And so, uh, it's kind of easier to wait for somebody else to do it than it is to like pick a random employee and be like, good luck. You know you know you're gonna be able to go make you a star yeah good luck you're gonna be able i mean some people can do it but like that's not why people typically apply to jobs because that's you know if they wanted to do that they would go start their own thing so i was kind of worried you know like okay what is my responsibility going to be like am i going to be like a normal
Starting point is 01:18:17 stripe employee or not and then like sort of the third box besides just like me and the community was like what does stripe want to get out of this i really wanted to know like what stripe wanted to get out of it because it's hard to predict you know if we're 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 right if something's like directionally pointing in the right direction and it can work like they're more than happy to take a chance. And with indie hackers and Stripe, it's kind of like indie hackers doesn't really capture a lot of the value that it creates.
Starting point is 01:18:51 If people start companies and their companies succeed because of indie hackers or because of a story they heard or because somebody helped them on the community, how do I make money from that? It turned out I didn't. But other companies exist 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. And so Patrick really just trusted like, hey, we think that you can make indie hackers really big, really meaningful. You've done a great job so far. It's hard to even measure. Even if you do make it big, we'll never really know exactly how much has contributed and added when to our sales. But that's fine. And so a couple of questions here and i'll ask them together so you know both
Starting point is 01:19:26 are coming you don't have to give me numbers or clauses but i'm looking for broad strokes what do you need to put into a legal contract in order to allay those concerns and what do you just leave to trust because ultimately these these things really are come down to do you trust me do i trust you and are we aligned so that's the first one the second one 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 never feel like the most qualified to answer acquisition questions. People, even though this is acquired, people call me all the time like, hey, I'm going through an acquisition. You went through one. What happened with you?
Starting point is 01:20:04 I'm like, it's so specific to my situation no employees yeah i was like a solo founder with no employees like i hadn't even incorporated but like there's some like little tricks and things that helped me so uh the first thing that happened was that patrick suggested that we communicate over text so we like got on whatsapp which instantly like i was like oh this is so smart because like i had been sitting there like i think it was a sunday like typing out an email, this acquisition numbers negotiation. And it was such a high pressure thing.
Starting point is 01:20:30 What am I going to say in this email? Versus text, it's just so casual. You're just firing off messages. And it just lowers the stress and almost the adversarial nature of it in a strong way. So that was the first tip. But then I thought about, okay, well, how do I value what Ind know, what indie hackers is worth? Like, what am I going to be happy with here? And I think your first question was also like, how much does trust come into it? So like, the first thing I started doing was trying to answer both of these questions,
Starting point is 01:20:54 actually, through kind of back channeling. So I just emailed as many people as I knew, who either worked at Stripe, had dealings with Stripe, or had dealings with Patrick in the past. I'm like, hey, what kind of person am I dealing with? And I got like a lot of really positive stories. Like this is a person who cares deeply about like what's good for people, et cetera, very ethical, et cetera. And like, I think you need that level of trust because like in a contract, as I soon found out, like there's just so many random like loopholes and like edge cases that you haven't considered and just like really easy ways to get kind of screwed over like at some point uh i was talking to patrick and we were hammering things out and at like one point i got an email that wasn't from patrick it was from like stripe general
Starting point is 01:21:33 counsel and i'm like oh shit like maybe i should have a lawyer because i don't know what this guy's talking about so then i went and hired a lawyer and like uh her name was metall she was great but she was just like the most paranoid person ever she was like here all the ways they're gonna screw you up they're gonna do this they're gonna do that they're gonna do this and like every single contract that like came she like found some way to tighten up the language or just like go to bat for me in ways where like because I had a lot of trust perhaps naively like I just would have been like ah it's fine like they have like the best intentions here and so it's kind of like you know trust but verify like i had a lot of trust and i don't think i would have done the deal if i didn't trust that like everybody involved was being
Starting point is 01:22:10 sincere with what they said that they're like sort of thoughts aligned with their actions and their words but also having someone in my corner to like make sure that these things wouldn't happen was i think important and gave me a lot of security yeah well the thing about these situations like this is like the documents and the clauses and all that that they exist for when things go sour you know like anytime you are looking at those documents like things are on a bad path you know you don't ever want to look at them yeah but if you have to look at them know, what is written in those documents is what is going to happen. So exactly. So they're important and they matter. And I think in my situation, like what kind of happened is that we like agreed on numbers, but at like in a very like high level,
Starting point is 01:22:55 non-specific, like this is what would make us all happy way. And that happened like pretty quickly. It didn't take that long. And like part of that was also doing research, like how much to engineers at Stripe get paid. Like, can I, you you know by that point i was pretty good at getting people to reveal like numbers to me from working on any hackers so i got a lot of numbers i was like okay like this is what i want and i was like i tried to be a firm negotiator but like you kind of agree on these numbers and then you go to like draw up a document and it turns out there's like just a million little edge cases you know like okay like if you like for example if you're talking about stock like what kind of stock do you want what like what class like when is it fast what period is it fast like how long i had a refresh
Starting point is 01:23:28 this work like all sorts of different things that i think if you're kind of like a typical employee you might not consider but if you're coming in through an acquisition like the sky's the limit like you can ask for or demand like literally whatever you want and put it in a contract it's going to be your special contract that no one else at the company has anything that's even like that so for me like it wasn't just like kind of worst case scenario. It was like, okay, well, 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
Starting point is 01:24:02 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? I don't know how much I'm legally allowed to say. Don't even get close. I think that what we're interested in 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 like, number. This company sold for X amount. But that's, in my experience, rarely how it happens.
Starting point is 01:24:37 It's rarely that simple. And 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 Stri stripe like for the love of god like take the equity you know yeah take the stock uh you know if it's like if it's a group on then like i don't know you know maybe you want the cash and like this is like an exercise well this is the difference i think between you know like like salesforce by slack it's about the number right like that's because it's a company buying, it's an entity buying, a corporate entity buying a corporate entity. With an indie hacker business, like no, it's you.
Starting point is 01:25:09 It's literally you. And I think, I don't know what like Elon Musk's situation is, but he has like all these like weird like earn out bonuses where he gets like more money if like the stock price goes up. So even like those big company situations, like there's all sorts of ways to sort of like figure things out.
Starting point is 01:25:22 Like, you know, if Salesforce by Slack, like what does that mean for Stuart Butterfield? Perhaps he could say, I want more money if we hit these extra targets, etc. And perhaps Marc Benioff would be like, sure, that's fine. And so I think if you can think about these creative ways to align your incentives, it can result in a happier process. And maybe on both sides. Maybe your acquirer wants to pay you more if you hit performance targets,
Starting point is 01:25:43 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 kind of a win-win, even though they're sort of on the hook for more money in the future. In my particular case, it's funny because IndieHackers is very much an IndieHacker business. I was just making money from advertisers. I had some affiliate links on the site. I think I was making like $7, and a half eight thousand dollars a month by the time stripe acquired the company whereas like today i feel much more like a high growth startup where like stripe owns any hackers but they're like almost kind of like an investor and like
Starting point is 01:26:14 my goal is to like grow as much as possible and like i don't make any money like any hackers doesn't like have any sort of revenue we bring in we have kind of a budget which is almost like funding to help us grow and so it, it 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. You know, the comp at that point is more to intrapreneurship, which is such a funny word because it's like they took a French word and then changed it to sound like an English word to get the point across. Anyway, what differences do you notice between indie hackers, which is a wholly owned subsidiary of Stripe? And I'm sure
Starting point is 01:26:51 that may not exactly be technically correct, but it's sort of its own brand. It just has a by Stripe thing on it's run by you versus the things that start within Stripe, but are their own self-contained thing like Stripe Press or like Stripe Atlas. Yeah. I mean, I think branding is by far the biggest difference because it's pretty obvious to most people who are aware of IndieHackers know that IndieHackers started before Stripe. And they know that it's kind of like my thing. I'm very transparent. They're going to listen to this podcast and be like, clearly, Corlin is running this on his own. This is not like a super heavy-handed Stripe initiative. Plus, a lot of people don't even know IndieHackers is owned by Stripe. There's a very small little logo that says
Starting point is 01:27:28 Stripe at the very bottom of the website that you kind of have to search to find, which is freeing in a way because it gives me the ability to make my own decisions that don't necessarily reflect on the Stripe brand. I remember a buddy of mine at Stripe who kind of ran the Stripe Atlas community got an email from IndieHackers.
Starting point is 01:27:48 He's like, oh my God, you said fucking an email, like stripe email and i'm like i said fucking like i thought i have probably like a dozen of these emails uh there's no one at stripe is that kind of monitoring that you know there's a lot of trust that goes both ways like i trust stripe and they trust me and like it doesn't you know it's weird in a way like i feel like a lot of the positive things and feelings people have about indie hackers sort of get accrued to stripe but like some of the riskier decisions like don't weigh on stripe at all and so it's almost best of of both worlds right whereas i think if like i you know started some stripe product internally like stripe press like that has stripes name like literally in the name which means it's a certain like level of quality that has to rise to there's a certain standard that has to rise to it's harder to get things off the ground when you do that like you need to match like certain accessibility
Starting point is 01:28:28 standards and have like a certain reach of people in different countries and have all these different languages i think it's just harder to iterate on any sort of like startup type initiative that's trying to find product market fit if you have all of these expectations on you this is why i think it's smart for like google when they're doing their innovation so like try to like spin 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 viacom lawsuit was going on like there was all sorts of you know people were up in arms there's crazy
Starting point is 01:29:05 stuff happening you can maybe say there's still this crazy stuff happening on youtube now it's like google video was a failing product like it was trying to do the exact same thing but was going through google's standard process you know yeah they weren't gonna just you know put movies up on there that were filmed with a you know camcorder in a theater like you can take bigger risks through an acquisition especially of like an established brand on its own. That's really cool. All right, so tell us now why has it made sense for Stripe? And I mean, this is a little bit of a softball question,
Starting point is 01:29:35 but like, how's it going? How's it gone? Was it a good idea for Stripe to buy indie hackers? What have you built to do any integrations if you have? 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. There have been years where we met like twice. There are years where I've sent him 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
Starting point is 01:30:00 IndieHackers, 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 worried that for you to grow, you would have to just run faster and faster. Because when Stripe acquired IndieHackers, it was still primarily just a media company. We were doing nothing but putting out these interviews. And we had this very fledgling community forum but like it was like you had to like click a link to get to it and it was only like a small number of people
Starting point is 01:30:31 whereas today the bulk of what happens on indie hackers is sort of user powered it's more of like an actual platform where like i'm not doing like the vast majority of the value that indie hackers creates the world is like it does not come from me you did it You shifted from media company to software product. Exactly. Which I always wanted to do, but it took Jesus that it take a long time. Um, so probably I would say like the biggest accomplishment since joining Stripe was just the growth of the community forum, which is now on the homepage. If you go to indiehackers.com, you just see dozens of conversations where hundreds of people are sort of helping each other out, asking questions and and helping each other start companies, meeting co-founders, without me really doing anything.
Starting point is 01:31:08 The company profiles you create through interviews and that people create themselves, they're all mixed together. Yeah. Yeah. Kind of. And I've been trying to consolidate things. They're not quite consolidated yet. So there is kind of a separate section on the website where you can go and you can read. And then we've done about 500 interviews now. All the different interviews from indie hackers who've kind of shared their stories and like you can kind of sort and filter those you can also go to sort of the product directory which i mentioned earlier where it's just more like self-serve like anybody can add a product there you can share how much
Starting point is 01:31:35 money you're making share your milestones along the way and everybody's sort of there competes to have like the best milestone every day so we have this leaderboard that kind of resets and whoever posts like the best update for that day in terms of upvotes gets to the top of the leaderboard and they get more traffic, et cetera. And so it's kind of a mechanism to incentivize people to fill out these little timelines, which has a side effect that everybody else can go read the timelines and learn how to build a company from these examples. So that's grown to like 12,000 products. We've got 500 interviews. We have a podcast that went from, I think, just maybe like 1,000 downloads total when Stripe acquired IndieHackers to to now millions of downloads and the community forum has gone from just a few
Starting point is 01:32:10 dozen conversations a week to the point where there's like a thousand comments a day over 250 posts every single day in the community forum and just like tens of thousands of people helping each other out so uh you know based on the numbers indie hackers has grown like tremendously since we've joined Stripe. So awesome. And one of the things we like to measure is kind of like a rough estimate of how many people have started companies
Starting point is 01:32:31 as a result of IndieHackers. So we kind of send out a survey to people maybe six months or so after they join. And we ask them, we say true or false to different questions. And one of them is, would you have started your company if not for IndieHackers? And most people are like, you know, would you have started your company if not for any hackers?
Starting point is 01:32:45 And most people are like, Oh yeah, I would have started it anyway, or I haven't started yet, but a good 15 to 20% of people, depending on the month, say they would not have started their company if they didn't encounter some story or some person on indie hackers.
Starting point is 01:32:56 And if you multiply that by like 140,000, you know, different people who've joined the community forum, like that's, that's a very substantial number of companies, a lot of tiny companies and some of them have like gotten bigger gotten acquired a lot of them are on stripe and sort of the way that patrick explained to me earlier when i first joined stripe was like hey
Starting point is 01:33:14 it's your job to you know get people to start companies it's our job to have a product that's good enough to win them over you know i'm not like sitting here trying to like hawk stripe and convert people to stripe like that's something that stripe does on its own and what was that 140 000 user number when you were acquired ish let me look it up i'm also curious i'm this is the third time i've done this to you i'm queuing up two questions approximately what percent of indie hackers use stripe as their for their company so the second one i don't know the answer to we don't really have like a process like we don't measure you know like there's like it's a lot of just trust right okay like we know this stripe is pretty damn good as a product uh
Starting point is 01:33:56 comes up on the community forum all the time i think it was the most referenced company and all the interviews that i did even before joining stripe i mean honestly i don't even know what else you would use if you want to take payments on the internet. You could use a ton of other stuff, but they're just like custom services that are white labeling Stripe underneath. Like that's what Glow is.
Starting point is 01:34:13 Like I don't even know if there is another alternative. It's a really good product. Yes, David, there are alternatives. It is also a very, very, very good product. Alternatives worth using. let's put it that way so for me to answer your question on exactly how many users are right when i joined stripe i have to run like kind of a query it'll probably take me like a couple minutes so like is it worth it on air sequel writing well do you have any mental ballpark of like on the order of a thousand
Starting point is 01:34:41 ten thousand 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, the scale and it's been what three and a half years. Yeah. It's been three and a half years.
Starting point is 01:34:57 I joined in April, 2017. So, and the accuracy has been a stripe for much, much longer than it existed before stripe. That's really cool. Even just like super ballpark numbers, let's say 100,000 companies added
Starting point is 01:35:10 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. The really interesting thing to me, and now we're in, so for people who listen to more acquired episodes, we've been through history and facts a little bit right now.
Starting point is 01:35:35 We're in what would have happened otherwise. And then we, we've done a lot of playbook as well, but we can specifically call that out. You know, if Stripe hadn't acquired IndieHackers, it's not like all the companies that have been created wouldn't have used Stripe. Like, I don't think you'd influence any of their decision on what, you know, who to use for payments. So what they were really doing is saying like, man, this thing is really good for our business that it exists. Let's make sure it can thrive as much as possible. It's interesting to me trying to think through the scenario where Stripe didn't acquire indie hackers and the exact same outcome happened for Stripe. Yeah. Again, I don't measure, would you have used Stripe? It's not even my goal really to
Starting point is 01:36:18 make people use Stripe. It's my goal to make people start companies. I 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 like when they hear a story on the indie hackers podcast when they go on the forum and they see somebody who's like like i met a yc founder at the stripe event a couple years ago and i was just kind of talking to him and he's like yeah i love indie hackers i'm like uh you know what's your experience with it it's like oh i read the story you did with this guy who started this like review site and i'm like i'm way smarter than this guy i could start a company so i did then i got into yc and now i don't go to indie hackers anymore and like that's
Starting point is 01:36:51 that's pretty that's pretty common like i meet a lot of people like that who were just like inspired like they literally started because they just read that it was possible and when i think about like me like i started my career because like people told me it was possible you know and i think spreading those stories helps people get started and like that's literally all i care about like i don't care how many of these people end up using stripe like that's the job of stripe engineers and product managers like make stripe the best product all right so it looked like you were uh you were writing some sequel there in the background while i was pontificating where'd you come up with so we've got we had exactly 1403 users on the day that we got acquired by Stripe.
Starting point is 01:37:26 So we're 100x bigger today. Almost exactly 100x bigger. Yeah, almost exactly 100x. Which is 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?
Starting point is 01:37:37 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. Did you see these stats that came out last quarter about new business creation?
Starting point is 01:38:03 Where it's like, like, yeah, like 600 people or 600,000 people a quarter in the United States are creating businesses like 10 years ago. And then last year it was like 800,000 people a quarter. And this year it's like one and 1.6 million people created a business or filed to start a business in like Q3, 2020, which is insane.
Starting point is 01:38:20 Like, so cool. Like, aren't there more and more winner take all opportunities like are we seeing now we're well into playbook but uh are we seeing basically like a barbell effication where the big startups consolidate to only a few big winners in each market but then there's like massive massive opportunity to go after a long tail yeah i think number one there's a lot of these winner take all startups but almost all of them create sort of niche business opportunities for other founders. And so it's not like this exclusive thing like, oh, 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 that get started off the back of that. So like, I think as an indie hacker, you don't have to worry too much about the winner take all companies. And then we have
Starting point is 01:39:07 all these like platforms, you know, YouTube, Substack, OnlyFans, arguably, you know, Twitter, where people are just like building audiences and businesses off the back of all those things. And so what's kind of cool is, it's kind of like never going to be, you know, all the niches are taken, there's no ideas left. And also, I think what people underestimate is just the number of people adopting technology for the first time. Because just because Zoom exists doesn't mean everybody uses it.
Starting point is 01:39:29 We've seen very clearly this year, way more people are using Zoom because they've been forced to adopt this thing that they've been kind of ignoring in the past because they just didn't want to. And so as more and more people get on the internet and create businesses and use these products, it's more opportunities.
Starting point is 01:39:42 And then most successful indie hacker businesses sell to other businesses. So it's kind of like this self-fulfilling sort of chain reaction where the more businesses there are, the more products they need. And so it's kind of cool to see it accelerating. And I wouldn't be surprised if that number in a few years is like 5 million Americans a month are creating an online business. Yeah, that's what I was thinking on that.
Starting point is 01:40:00 You've got the platforms like Stripe or Shopify. And know you've got the platforms like say let's well stripe or shopify like say and then you've got people that like start shopify stores or start businesses on the internet and you stripe but then there's this whole other category that i think is like perfect for indie hackers of like oh well there's actually stuff that you can build to help the people that are using shopify that are using stripe that like using Stripe that like, you know, there's so many businesses that have been started around Shopify that are like, and Stripe too, that are like not a business on Shopify. They are a business that provides us a custom set of tools for a certain set of users that need like hobby businesses. Like you're a hobby game store and you are both
Starting point is 01:40:42 buying and selling from your customers. Like your customers come and they trade in stuff like you can run on shopify great but like you also need some custom functionality to buy stuff from your customers boom business exactly i think like a lot of the smarter like founders are figuring out ways to kind of escape the competition because it's like okay you can build like a shopify plugin but there's like a lot of other shopify plugins so it's a cool opportunity but then you get kind of crowded out like i'm talking to a guy tomorrow his name is jordan oConnor. And he's got like a really cool story where he's like, you know, a father, a husband, he had a full-time job and he would like eke out time every morning to kind of work on his business because he knew that like after like 8am,
Starting point is 01:41:19 his son was going to be awake and he's going to have no time at all to do anything. And so what he ended up doing was kind of escaping the competition and he built a bot for this app called poshmark which is huge like a lot of people buy and sell like their used clothing on poshmark but they don't have a marketplace like they have no like they don't even have an official api so he just sort of like reverse engineered things he's like there's not gonna be any competition here but it's kind of the same playbook like build you know for this an ancillary tool for this bigger platform and he built like kind of a bot that helps you like do well on poshmark and i think he got to like 20 grand a month and now he's just kind of like he quit his job he's just kind of set and he's just like doing other
Starting point is 01:41:51 fun projects now that like you know interest him from year to year while that bot just kind of makes money for him in the background magic of software it's pretty crazy we want to thank our longtime friend of the show vantaanta, the leading trust management platform. Vanta, of course, automates your security reviews and compliance efforts. So frameworks like SOC 2, ISO 27001, GDPR, and HIPAA compliance and monitoring, Vanta takes care of these otherwise incredibly time and resource draining efforts for your organization and makes them fast and simple. Yep. Vanta is the perfect example of the quote that we talk about all the time here on Acquired, Jeff Bezos, his idea that a company should only focus on what actually makes your beer
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Starting point is 01:43:30 and your company is ready to automate compliance and streamline security reviews like Vanta's 7,000 customers around the globe, and go back to making your beer taste better, head on over to vanta.com slash acquired and just tell them that Ben and David sent you. And thanks to friend of the show, Christina, Vanta's CEO, all acquired listeners get $1,000 of free credit. Vanta.com slash acquired. All right, well, I'm gonna start bringing us home here. Cortland, answer this question however you see fit, but how would you grade the IndieHackers acquisition by Stripe in terms of was that a good use of capital and resources for Stripe?
Starting point is 01:44:06 Oh, A+. 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 goodwill towards Stripe,
Starting point is 01:44:20 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 were very concerned early on. You know, they're very worried. And I don't think I've met a single person who said like they aren't happy that it happened. So it's hard to imagine it having gone better. Yeah. Should more people do this? I mean, the way that I'm sort of categorizing this in my head is they made an investment to
Starting point is 01:44:45 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 they should be a lot more creative and imaginative. I think like there's, like as humans, we have this impulse to just like, to just like mess with things. It's really hard to buy something and then not touch it. You know, it's really hard to do that. And I think when people think about like, okay, if I buy this, like what am I going to do with it? I think, oh, it's going to be like so much work. I have to do this, I have to do that. And they don't like make these acquisitions. Whereas I think at Stripe, they're very much
Starting point is 01:45:14 like, no, Coraline's doing a good job and we don't have to do anything. And like, if we can just ensure that it keeps going, like you said, like that's a huge win by itself. But there's other wins too. You know, I think one of the trends we're going to see going forward is like tech companies basically owning like some kind of media company which i think is super powerful because like media companies are what connects with actual people on the ground and in a way like indie hackers is still very much a media company like i still spend a lot of time on the podcast we spend a lot of time on our newsletter put out a ton of content and we're sort of like becoming a platform almost like Substack-esque, where we're enabling other people to build newsletters and grow their audiences on IndieHackers. So I think even without just having IndieHackers continue to exist,
Starting point is 01:45:52 and even without it driving excess additional customers to Stripe, it's just a good way for Stripe to be able to communicate in the future if it wants to. We're launching this thing, or we think this about the world, and now they have a place that's not just hacker news or Twitter to do that. Has Stripe done any, anything else like this since you've been bought or? Yeah. Stripe has a magazine called increment magazine, uh, just increment.com. It's kind of like the best sort of magazine for all sorts of basically work that gets done. So they've done like issues on like software engineering and APIs and the cloud and being on call. And like people love this magazine. It's really well produced. It was created by kind of initially Susan Fowler, who's the engineer who
Starting point is 01:46:33 kind of blew the whistle on Uber back in the day. And now she works, I think, at the New York Times. So that's like a really cool like Stripe project that I don't think gets enough press and attention. There's also like Stripe Press, which is kind of like an in-house thing. It wasn't exactly acquired. But all these sort of initiatives involve often people who come in from outside the company and help. They're all kind of moonshots. I put it in a very similar category to ND Hackers, even though it's different. But it's something that most companies wouldn't do. But Stripe kind of trusts, like, okay, well, what if we put out these books that help people become better founders make better decisions or start more companies it's hard to measure like how many people actually read this book and made a decision because of it but like
Starting point is 01:47:11 we can kind of trust that like they will do that because like we know that's how inspiration works and like it'll increase stripes bottom line yep makes total sense for acquired listeners because i know we're releasing this in in both feeds where can people find you? What should they check out first of the various indie hackers and Cortland 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've succeeded. And so I just recommend listening to a few of them and really absorbing like,
Starting point is 01:47:47 you know, what is this path like? You know, how can you start off maybe as an indie hacker and then eventually grow to start a much bigger company? I've interviewed like lots of founders of like YC funded companies and VC funded companies, but also tiny indie hackers who 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.
Starting point is 01:48:11 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. Can I wait for 2021? But seriously, like I'm in the best part of 2020 hanging out with you all virtually. So it's been a great year. The world aside, it's been a great year. The world aside,
Starting point is 01:48:28 it's been a great year for Acquired in the community. Can't wait for next year. See you in 2021, everyone.

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