How Courtland Allen Built Indie Hackers, with Ben and David from Acquired

Courtland Allen 0s

All right. What's up everybody? This is Courtland from IndieHackers.com and you're listening to a crossover episode between the Indie Hackers Podcast and the Acquired Podcast with Ben Gilbert and David Rosenthal. On Acquired, Ben and David deep dive into the stories behind companies that you've heard of and might use every day to try to figure out the strategies and the events that got them to where they are.

It's an excellent show. I listened to it all the time and I can't recommend it enough. So do me a favor, go check out their show. It's called Acquired. In this episode, unlike most other episodes of the Indie Hackers Podcast, Ben and David flipped the script on me and asked me about my story starting Indie Hackers. So, I hope you enjoy it.

Ben Gilbert 47s

Courtland Allen, welcome to Acquired.

Courtland Allen 49s

Ben, David, thanks for having me.

Ben Gilbert 51s

Yeah.

David Rosenthal 51s

So great to have you here.

Ben Gilbert 53s

Our pleasure. For anyone who has not listened to, your voice for the many hours that I have on the Indie Hackers Podcast. Obviously, we're going to reference it lots and lots throughout the show, but go check it out and very excited to be doing a crossover episode with you.

Courtland Allen 1m 8s

Yeah. I'm excited to do this. People have been asking for a while for me to do an episode on myself. Cause obviously Indie Hackers is kind of an interview show. I just tell other people's stories. And I've always been, as weird as it sounds, shy to do an episode on my own podcast. So, congratulations on being the first people to convince me.

Ben Gilbert 1m 24s

Look, we are the Acquired podcast and you did that mega deal exit to Stripe. How could we not cover the acquisition of the century?

David Rosenthal 1m 32s

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

Ben Gilbert 1m 36s

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

David Rosenthal 1m 42s

Yeah. So, Courtland is a former YC founder, MIT alum, and founder of a company that has been acquired by Stripe. All of which seems like it would fit very much into the Acquired theme, but there's a twist, which is. Unlike the big gopher broke we were jabbing before we before we hit record here about like the typical startup path that we cover all the time on this show is like trying to build the new version of standard oil out there except two, 10, a hundred, a thousand times bigger than the Rockefellers and the Carnegies could ever imagined.

Courtland is all about a different philosophy out there, the Indie philosophy. 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. Indie Hackers, I think, is really cool. We're going to get into it in this episode. It's kind of like if big tech and startups are the Rockefellers, this is the small business entrepreneurship of the 21st century. And I think it's really, really cool. So, we're pumped to do this.

Courtland Allen 2m 46s

Yeah. You're saying Indie Hackers is not a big splashy go for broke story, David?

David Rosenthal 2m 50s

I don't know. You're going to tell us.

Courtland Allen 2m 53s

No, it's really not. I like to think of it as the underdogs, you know, the Internet's been around for decades. And I think the world is still kind of slowly waking up to how much it's kind of changed the game for just regular people. Everybody's connected to everybody. You can reach literally millions of people if you're clever enough for pretty much $0.

People are creating these very tiny niche businesses that could never have existed 20 or 30 years ago. In some cases, not even five or 10 years ago, and I think it's becoming possible to sit down in your living room, wearing your underwear or whatever you're wearing and just create something that's super valuable to your community and your customers. 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. I think that's pretty crazy to check all three of those boxes. So thousands of people are doing this today. The question that I'm asking myself constantly is like, what happens when millions of people are doing this five or ten years from now?

David Rosenthal 3m 40s

Yeah, I think that's, what's so cool is small business entrepreneurship in the past was a great way to build wealth and do well for your family and for yourself. But with the same art, I honestly like a less amount of effort now on the internet, this path exists that the wealth you can build, even by taking this path, is still so much bigger than you could build, you know, building a dry cleaning business in the past or running a restaurant or like...

Courtland Allen 4m 6s

A lot bigger.

David Rosenthal 4m 6s

A lot bigger.

Ben Gilbert 4m 8s

Yeah. I'm not to foreshadow our sort of playbook too much, but it does remind me that 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 this sort of large-scale version of that is Walmart, but that is a very different type of business to run. With the internet, you can just do one thing in one niche, but you have a nationally, if not globally, addressable market. And so, I continue, Courtland from listening to your show, every time I listen to an episode, I get smacked in the face with, "Wait, that niches that big?"

And people find these crazy opportunities. I just listened to the Patio11 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, that there really are, if your TAM is the 3 billion people with the internet, then every niche within that TAM can be, on its own, big.

David Rosenthal 5m 9s

Hey, man. Starlink is coming soon. It's going to be 7 billion.

Courtland Allen 5m 12s

Yeah, exactly. If you have a business that only appeals to one in a thousand or one in a million people, you need to live in a very big city to create a brick and mortar business, that's going to survive. But on the internet, that turns out to be millions of people who can use your underwater bingo card creation, whatever it is that you're making, which means that pretty much everybody can figure out something really specific that no one else is doing and kind of stake their claim on the internet, which I think is super cool.

David Rosenthal 5m 37s

I hear the real estate is cheap too. Alright, so let's get into your story.

Courtland Allen 5m 41s

Yeah.

David Rosenthal 5m 42s

Okay. Let's start way back before MIT, your family and your mom specifically was an entrepreneur when you were growing up, right?

Courtland Allen 5m 50s

Yeah. I was just talking to Jason Calacanis about this on his podcast, where he was talking about a kind of opportunity, you know, 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 kind of a different starting line. And when I look at my childhood, I had a very good starting line. I had two loving parents. They're very attentive. They're very devoted. And we were sort of lower middle-class, but very comfortable.

And like you mentioned, my mom was an entrepreneur. She was always doing her own kind of crazy hijinx 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 different role and they would make crazy furniture for celebrities.

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

David Rosenthal 6m 45s

Yeah. You can do this. And it'll be fine. You can have a good life. Right?

Courtland Allen 6m 49s

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

And so of course, I was addicted to video games and whatever I could play, but from the adults perspective around me, they're like, “Oh, this is a computer whiz. You know, whenever I've got a computer issue, Courtland spends so much time on his computer. He can just swoop in and fix it.” Cause I was doing all this IT work on the side and of course nobody ever paid me.

I made $0. Like I said, nine-year-old fixing people's computers, but I got a lot of positive encouragement because from my perspective, I was just playing games and fixing bugs and stuff. But from the average adult's perspective in the mid 90s, they are looking at the tech boom. And they were looking at Microsoft stock price. And the fact that Bill Gates was mega rich. 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. Keep it up." And, what was cool about that was, you know, I got to be a little computer nerd and also see that this really old computer nerd was universally respected by every single person that I ever met.

And everybody told me that it will be a cool thing to aspire to kind of be that. So by the time I was 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. How do I get on that path?"

David Rosenthal 8m 5s

It's funny that in some ways it's like echoes of the Tim Sweeney story and Epic games, you know, had him starting out first with, it was his older brother, right? Right, Ben? That had a computer hardware business. And so he went out to visit his brother, got hooked up with computers, got obsessed, then started an IT consulting business, after the lawn mowing business.

Ben Gilbert 8m 28s

Nolan Bushnell, too. When we asked Nolan about starting Atari, he was fixing TVs. Not at all to put myself in the same category, I was fixing teacher's computers in middle school as my, I think I was making like seven bucks an hour, Courtland. So, sorry I was drawfing you there, but, yeah, that's so many people's entree before they actually get into programming is basically just fixing stuff.

Courtland Allen 8m 49s

Yeah. And I think it's important. I've taught people how to code in subsequent years, and there's this kind of base layer that gets ignored of just computer literacy. Where the people who learn the fastest are people who just, they're just very comfortable if their computer crashes or has an error. They know all the keyboard shortcuts, they're good at Googling stuff. And if you have that kind of base layer of skills, it makes everything else much easier.

Ben Gilbert 9m 9s

Yup.

David Rosenthal 9m 9s

Totally.

Ben Gilbert 9m 9s

So did you, 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?

Courtland Allen 9m 23s

Oh 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? Yes. I had a saxophone, I was playing a lot of just corny, contemporary jazz music. Luckily, the computer stuff won out at some point. And after that I didn't deviate. That was a hundred percent what I wanted to do. Had a ton of, just a ton of fun, just doing stuff in the 90s on my computer. A lot of support around me. You know, in one way, I think I had kind of the world heavyweight champion of childhoods, you know. It was really, really good, really advantageous. But I also had some hardship. My dad died when I was pretty young, I was in high school.

And for me, that was just a huge wake up call. Like, "Oh shit. Sometimes things get real and 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 almost kind of the perfect mix of hardship and encouragement and privilege in a way. And so, yeah, by the time I left to go to college, I felt pretty ready to take whatever the role is gonna throw at me. And also pretty far ahead of the curve in terms of knowing what I wanted to do. There's never a question like what major do I want to have? You know, what do I want to do after I graduate? I was always a hundred percent certain what I wanted.

Ben Gilbert 10m 35s

And I'm sure that tragic death in the family also forces a lot of early maturity, that you have to take on sort of more responsibility or at least think about the broader context around your life than just yourself earlier than you otherwise would have.

Courtland Allen 10m 50s

Totally. And I think for me, the biggest impact was just, you kind of get a floor. You establish, "Okay, this is the worst thing that's ever happened to me, and I survived it." It was terrible and all sorts of bad side effects you didn't even think about, but once you establish a floor, then a lot of other things just don't look that scary. They don't look like they're that big of a deal. Like, "Okay, what if I start a company that fails?” Like, "Oh no, I'll go get a job. Go get a job. And I wouldn't die." You know? So I think that's kinda what I got out of it.

David Rosenthal 11m 16s

I assumed that the computer, the love of computers and knowing what you wanted to do,getting out of the Kenny G phase,that's what brought you to MIT?

Courtland Allen 11m 24s

Yeah, the Kenny G phase was a good one to escape. Yeah,. 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. 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, you know, how do you get into MIT?" And she's like, "Well, get good grades and study and apply. And hopefully, they'll let you in." And I'm like, "Well, what if they don't?" And she's like, "You just go somewhere else." I remember thinking how frightening that was, I got one shot to do the thing that I wanted to do.

If I got rejected that I would just be done. And in a lot of ways, that was a much scarier thing than I think starting companies that have the risk of failure. Cause you can start a company a million times. If it fails, there is no, "Alright. You know, that's it. You have to go somewhere else now." You can just keep doing it over and over again.

Ben Gilbert 12m 18s

How many companies have you started now?

Courtland Allen 12m 20s

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

David Rosenthal 12m 27s

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 regularly.

Courtland Allen 12m 36s

Yeah. I applied a lot.

David Rosenthal 12m 38s

Is this like an every quarter thing? It's like register for classes, put in the YC app?

Courtland Allen 12m 42s

Well, I was a pretty bad student. I just didn't really want to learn. And I thought all this stuff I was learning in my CS classes was boring. And so I spent a lot of time working on my own side projects. 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. I got really hooked and I would spend a lot of time applying. I got rejected at least two or three times.

Ben Gilbert 13m 3s

Had Dropbox already gone through YC at this point and come in at MIT?

Courtland Allen 13m 6s

{At some point during when I was in college, Dropbox went through. And Dropbox is also an MIT startup. Everybody on campus had a bunch of free Dropbox codes and we have a ton of free space and everybody knew their story. There's a lot of positive encouragement there as well. Like, "Oh, you want to apply to YC?" Everybody knows what that is and thinks it's cool to just apply even if you get rejected.

I got rejected once and I got an email from Paul Graham where he was like, "Oh, I think, you know, you could have done this better." I remember just showing that email to my friends, so proud, “Look, PG responded to me.”

Ben Gilbert 13m 33s

Right. This is just as good as getting in.

Courtland Allen 13m 36s

Yeah.

David Rosenthal 13m 36s

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

Courtland Allen 13m 40s

The very first one was this company called Fmail, which stood for - get this Gmail for Facebook. We, Facebook released their platform sometime when I was, I think, a junior. And at that point, I'd never really built a web app. But a buddy of mine was just super encouraging. He was like, "Oh, this is so easy, Courtland.. Just go learn PHP.” I’m like, “PHP, like, what is that?" So I went online, I started learning it and I was like, okay, how do I store user information?

David Rosenthal 14m 3s

Facebook was all PHP.

Courtland Allen 14m 5s

Yeah, yeah. It was all PHP. And I just kept asking well, how do I do that? So he's like, "Oh, just go learn SQL.” 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 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. Like, "Oh, crazy MIT genius figures out a way to put Gmail inside of Facebook." We've skinned 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. If 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.

Ben Gilbert 14m 56s

It's so true. That was an era too where there were so few web products where when you did one and you made a new website, it could kind of stand out because there just wasn't a lot of noise. I remember, you fled back so many memories there. When I was in college, it's funny, yours was Fmail. Mine was called Hacker Follow and it was Twitter for Hacker News. 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. And that's even what Facebook was written in, David, as you mentioned. And the web was like a, it felt like a small place.

Courtland Allen 15m 34s

Yeah, it really did. And I think to some degree, it always kind of feels like that in hindsight, you know. I think like 10 years from now, people will look back and be like, "Oh, the quaint times of 2020 when you could do, when you could do anything and it would get attention."

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

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

And the same thing is true with ideas. So I think there's always this sort of framework you can use to come up with interesting ideas. And 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 that was enough to stand out. I think that's still true today.

David Rosenthal 16m 31s

Yeah. Okay you mentioned Hacker News, which I assume is going to continue to play a big role in this story here.

Courtland Allen 16m 38s

Yeah.

David Rosenthal 16m 38s

Were you hanging out on Hacker News while you're at MIT doing all these YC applications?

Courtland Allen 16m 43s

So back in the day, Paul Graham used to write on his blog all the time about startups and all sorts of different stories. And it was very motivational, inspirational, and positive. And then he had this website he created, which again, he just seemed like it was very haphazard. He's like, "What if I had a little Reddit clone?" And of course it's now like millions and millions of visitors or whatever. But if you wanted to apply to YC, you had to be on Hacker News.

Ben Gilbert 17m 5s

It exists because he was dissatisfied with R programming and was asking Alexis to make that better. Like Alexis and Steve, I think it was either to make it better or maybe to invent it at all because that subreddit didn't exist yet and got frustrated with their slowness and started Hacker News on his own.

Courtland Allen 17m 23s

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

So if I look at my HN account right now, I think it's, yeah, created October 8, 2008. I was on HN way back in the day, reading everything, digesting everything, and then trying to leave smart comments that I would be probably embarrassed to go back and look at it right now.

David Rosenthal 18m 0s

It's so funny to think about now, God, how many companies, there are like 300 companies that go through YC-ish about every year. But it was this little cornering community of the internet, I mean it still is a community, a very large community now in a certain sense, but...

Ben Gilbert 18m 14s

Yeah, I remember being a YC fan first and foremost, and using the products. I was proud to be a Dropbox user and abandon my flash drive because it was a YC company. I suppose that is even actually a bigger effect today, but it felt at some point like a club. I remember, I think it was senior year in my high school, I felt like I was in some sort of club for even knowing what it was.

Courtland Allen 18m 35s

Yeah. I kind of had that feeling and then I eventually ended up doing YC and I remember distinctly that there were maybe 35 companies in my batch or something. And all of us felt like, "Oh man, YC, it's jumped the shark." It used to be so intimate, and so small back in the day, you'd go to PG's house. And now, it's just this huge, impersonal thing, you only get to see Paul Graham once or twice a week, what even is this? And of course now it's 10 times bigger than it was back then.

Ben Gilbert 18m 59s

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

Courtland Allen 19m 2s

In college, I ended up being linked up with these two grad students who had this cool idea for this new version of email. And then we tried working on it and it was pretty cool actually. We got a lot of press, we got a lot of attention, but we didn't charge any money for it.

And so after a year of working on that, we ran out of money. We'd won some business planning competition, it was like 25K. So I kinda 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 get into YC.

I worked, I got maybe enough money for four months of rent, moved out to SF. I just started reading Paul Graham's RFS, his Requests for Startups that he would publish. One of the ideas on there was kind of related to what I'd already been doing. He had this whole thesis that, you know, the email inbox is just an unexploited domain, and you can have a Trojan horse where you get in there with some sort of productivity app or something.

And then once you get all of the email users off Gmail, you convert them to your own thing. And so that was his obsession, like these clever tricks you could use to get a ton of people on your apps. And so I was like, "Okay, let's just do that." So, I met another guy again on Hacker News who had kind of posted, "Hey, I'm looking for a co-founder."

David Rosenthal 20m 7s

I read that. You met your co-founder on Hacker News, right?

Courtland Allen 20m 9s

Yeah. He is one of my previous competitors to my earlier email thing and his app also wasn't doing that well. So we're like, why don't we join forces? We met in the coffee shop in San Francisco. And I had maybe a month of money in my bank account. I don't know what I would have done, but it's just like, had to somehow find money or get a job immediately. But we applied together and the process was super quick. We got in, PG asks 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 so I can pay my rent this month?"

David Rosenthal 20m 38s

Oh, was this, what year was this? What, 2011-ish?

Courtland Allen 20m 41s

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

David Rosenthal 20m 48s

This was before the Yuri Milner SV Angel deal where you got 150K, right?

Courtland Allen 20m 53s

That happened during our batch. We were the very first batch for that. And I remember the previous YC batch was super jealous cause they only got, you know, 17K or whatever. And so that's what we got at first. It was 17K, divided by two, me and my co-founder, you know, we have enough for the two of us. We ended up moving into this rent controlled apartment in SF and just eating a lot of oatmeal and crackers and stuff.

And then I remember, one day during YC, they kind of called us down, a Friday or some off day. Like, "Hey, it's very important. Everybody come down." We went down to the YC headquarters and they had those telepresence robots kind of walking around, sort of like a camera, like in a screen on wheels. And there's Yuri Milner face on it, this Russian oligarch, billionaire walking around and talking to everybody and we've got an announcement. And it was like, "Yeah, we're going to give everybody $140,000 of additional money, sort of no strings attached as an investment." That was one of the best days of my life. I was like, "Okay, well, I'm going to start eating. I'm going to upgrade to ramen now and not have to worry about where my rent’s going to come from.

Ben Gilbert 21m 52s

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

Courtland Allen 21m 59s

I couldn't tell you. I can't really remember. I think it probably was a convertible note and this is before they had, I mean, this is before they had the safe.

Ben Gilbert 22m 6s

But it wasn't literally free money.

Courtland Allen 22m 9s

No, it wasn't literally free money. Whatever strings attached...

David Rosenthal 22m 11s

I think it was uncapped though, if I remember.

Courtland Allen 22m 13s

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

David Rosenthal 22m 18s

So, at this point you're getting it probably feels like a huge amount of money in funding. Right? Like you don't have any customers, right? Nobody's paying you anything.

Courtland Allen 22m 25s

We had literally nothing. We had a bunch of janky code that I was writing and my co-founder was going around, you know, doing some marketing stuff and trying to generate press and hype for a thing we hadn't built yet.

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

Then, when I worked on that To-Do, if I added a due day or I checked it off, you would get an email that said like, "Hey, Courtland is this far along in the To-Do or Courtland just completed it." It was supposed to be like this viral thing that would take over the inbox and everybody would have it. And eventually we did launch in YC and we got a decent number of users. By the end of YC, I think we had a hundred thousand users. But back in the day, that was nothing. “The Social Network” had just come out a few months earlier, you know, a million dollars isn't cool. A billion dollars is cool. That was kind of the mantra and no one cared that your app had a hundred thousand users, that was meaningless.

Ben Gilbert 23m 24s

I'm also dying over here because after Hacker Follow, my first app was a task list that I launched for iOS 3, which is 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 sort of connectivity for Gmail Tasks that would eventually become, I think they turned it into its own thing, but it was like constrained within Gmail forever.

David Rosenthal 23m 50s

Yeah, it's Tasks.

Courtland Allen 23m 51s

Yeah. I think it's still there, if you know the right combination of the keyboard shortcuts, you can get a little task for you to pop up in Gmail. But yeah, it's not the most inspired idea, like a To-Do list, right? Every entrepreneur, every programmer has a bunch of stuff they want to do. And when you think about solving your own problems, like “If only I could organize my tasks into a little list of checkboxes.” So we did that and it kinda sort of worked, you know. But it wasn't like the home run...

David Rosenthal 24m 11s

But we'll do it in email.

Courtland Allen 24m 13s

Yeah, we'll do it in an email they are up. There it was, like 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 and people were like, "No, I haven't. Maybe I should sign up." So we kind of combine those things.

And when we got to demo day in YC, the very end of YC, and we presented. And investors just, they weren't interested. They're like, "Yeah. You know, you've had okay growth, but where's this really going? And we've invested in email startups in the past and they're all dead. What's gonna make yours different?" And we didn't have a good answer to that. So we went to the summer after YC with probably still like 120K, 130K of this money in the bank trying to figure out what are we going to do with this startup that’s not growing fast enough for us to raise money?

David Rosenthal 24m 54s

And then one of the talks, maybe was it like a Tuesday dinner talk while you're on YC, was Kevin Hale from Wufoo.

Courtland Allen 25m 3s

Yeah. So Kevin Hale was this, I thought he was the coolest guy on planet Earth. We had these, you know, YC dinners every week and people would come in and we had the Heroku founders come in and they just sold for $300 million. And they just bought us, like bought us all the nicest stakes and, you know, they were just super suave. And they were so cool and flashy.

David Rosenthal 25m 20s

Drive up in their Lambos.

Courtland Allen 25m 21s

Yeah. And I think PG brought in the CEO of Yahoo at the time, who was the super extroverted guy who said a lot and it sounded really good, but you can never quite tell what he said afterwards, you know? PG was like, "This is an example of a stereotypical CEO." And then Kevin Hale came in from Wufoo and he was just a cool, calm, and collected character.

And he was just like, "Yeah, we're not raising any money, you know. Like we packed our bags, we moved to Florida, we're making forms, but we're making form sexy. And we do profit sharing with our team. You know, we go to the beach all the time. People work remote. I don't even know when they're working really. We get 10 calls a week from VCs who want to invest and we're like, no, we're making millions of dollars. We're cool." And no one else had said that. No one was making money. I didn't even know how you could make money. Cause Stripe wasn't even a beta at that time.

David Rosenthal 26m 5s

It was, so in your cohort, nobody was talking about...

Courtland Allen 26m 9s

No.

David Rosenthal 26m 9s

It was just about raising money.

Courtland Allen 26m 10s

There's a few companies that had some sort of revenue model, but all the companies that were celebrated were the ones that had just raised the most money, you know? Who raised from A16Z the earliest, you know. There's one founder in our batch, who I will not name, who raised from A16Z the very first week of YC.

And they raised millions. And they were putting up kind of Facebook growth numbers and everybody worshiped the ground that these founders walked on, the whole, it was obnoxious to the point it was I didn't want to see them. But you're kind of jealous too, because you and I, I kind of want that level of success, you know? But at the end of the day, nobody was making money.

Nobody wanted to make money. No one, it was all about growth. And so when I heard Kevin Hale talk about how Wufoo was just kind of crushing it. I remember running up to PG and like, "Hey, you know, we're not growing that much. What if we just did this? What if we charged money?" And he was like, "That's cool. Whatever it takes to stay alive." You know, he was very much like, “Be the cockroach, you know, don't die. If you need to make money to survive until you pivot to a better idea, that's what you should do.”

But that sort of asterisk was always there. What you then do is pivot to a better idea that, you know, can make you a billion dollar unicorn because, well, who wants to just make a few million dollars a year?

David Rosenthal 27m 14s

It's so funny.

Ben Gilbert 27m 14s

David always reminds me that incentives drive behavior. And if you think about sort of why seize incentive here, do you think back on it and say, "Well, gosh. They sort of, for their portfolio construction, they needed us to be a billion dollar company." Or at that point, would YC have been happy with a bunch of Courtlands building profitable businesses?

Courtland Allen 27m 34s

When you interview, they really want to know that you have a shot at becoming a billion dollar business. Cause that's how the mechanics, it's 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. Like even before our batch is over, it was kind of clear that a few people had given up and they weren't really gonna make it.

Especially in the summer after our batch was over, just a lot of companies fell off the radar. I remember talking to PG over the summer, we signed up for office hours and went in and he was just happy we were alive and still working. He was like, "Oh yeah, we don't even know what happens to a lot of these companies after a certain amount of time. So, we're happy that you're here."

And I think after that, they're less adamant that you gotta go for a billion. You gotta go for a billion. You gotta be a unicorn. And they're like, do whatever it takes to survive and get to the next stage. I think in a lot of respects, that's kind of the hallmark of being a good entrepreneur. How can you take one, you know, small success and parlay that into something bigger? And eventually maybe you get another shot at going for the unicorn company. 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?

Ben Gilbert 28m 38s

Yeah, it reminds me he's got that one essay. I think it might be in Startups = Growth about the hill climbing algorithm. And you basically always try and find the next highest hill. And you would think that you could accidentally find a local maximum and not the global maximum that way, but in practice, whenever you're on a higher hill, that's a better way to get to the next hill. And you can sort of always use that way to find your way to the absolute maximum. It's a little ethereal, but do you sort of agree with that?

Courtland Allen 29m 6s

No, I completely agree. I think if you're creative enough and you think about it enough, you can figure out a way to your next hill. Indie Hackers today, is to my knowledge, the biggest online community of startup founders. Indie Hackers in its first month was a blog.

David Rosenthal 29m 19s

Yeah.

Courtland Allen 29m 19s

I think there's a lot of blogs out there. You started off with a very tiny hill and I made the blog as big as I think, you know, I want it to, maybe it could have been bigger, but it was pretty big. But there's always some way where you can say, "Hey, now I have this advantage that I didn't have last week or last month or last year. What ways can I use this advantage, you know, parachute over to that slightly bigger hill?"

And maybe you lose a little altitude on your way there, but then you're on this bigger hill and it's much easier. The analogy I like to use, maybe not hills, it's like a staircase, right? A lot of people will want to jump to the top of a staircase, right? It's very hard to jump to the top of a staircase. Very few people are capable of that feat. But it's pretty easy to walk up a staircase one step at a time. 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 kind of work your way there.

Ben Gilbert 30m 3s

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?

Courtland Allen 30m 21s

Startup founders.

Ben Gilbert 30m 22s

Startup founders. That's cool.

Courtland Allen 30m 24s

I mean, they're Indie Hackers. They don't mostly have billion dollar ambitions, you know, they're the underdogs. But a lot of them, I think once they get started, realize like, "Oh, wow! You know, I'm making some side income." And then a few months later, they're like, "Oh wow! I can quit my job."

And then at some point, you're making a lot of money and you're thinking, "Okay, well, what do I want to do? Do I want to retire to a beach somewhere? Or maybe what I want to do is build something even bigger." So a lot of Indie Hackers I talked to are no longer even Indie Hackers. They've raised the money, they're building bigger companies. And that's where their life path took them.

David Rosenthal 30m 52s

Well, that's what I think is so cool about this. I don't, unless you would disagree, you're the authority, but I don't think being an Indie Hacker means 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.

Courtland Allen 31m 6s

Yeah.

David Rosenthal 31m 6s

And go from there. And sometimes those become Notion, right? Or sometimes they become Indie Hackers and sometimes they become just a business that makes you a couple hundred thousand a year.

Courtland Allen 31m 19s

Yeah, exactly. I don't like to juxtapose Indie Hackers as a counter-argument to raising money so much as it is a counter-argument to having a boss and working a desk job and wondering “What if?” for the rest of your life. And being an Indie Hacker is really about the idea that you can achieve your own sort of freedom, whatever that means to you.

Maybe that's financial freedom, maybe that's creative freedom, so you can work on whatever you want. Maybe that's time freedom so you can work whatever hours and schedule you want. And so being an Indie Hacker is really this confidence in yourself like, "Hey, you can create something that'll make your life better 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."

Ben Gilbert 31m 54s

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've got all the option value in the world to continue to take it, whatever sort of trajectory you want to.

Courtland Gilbert 32m 17s

Yeah, exactly. And you know, the kinds of companies that I've seen people build, you think about business, like I almost feel we need a new word. Because you think about business that has all these connotations like you meant, you imagined a bunch of men and suits and a board room or something, you know, reading graphs. And then the word startup is not quite right. It's closer because you think about tech and technology it's like...

David Rosenthal 32m 37s

They’re wearing t-shirts instead of suits.

Courtland Rosenthal 32m 39s

Yeah.

David Rosenthal 32m 39s

But they're still the same thing.

Courtland Rosenthal 32m 41s

Yeah, exactly. There needs to be some, I don't know what it would be, like some third word where I'm just looking at people. I interviewed this founder, Sam Eaton on the 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 worked in growth roles at Airbnb and he just gotten 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. And we're going to be tech-enabled and we're gonna 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 DoorDash, they have their own delivery drivers, their own sort of internal mechanism. His sister's the head of Cookie R&D, and they're making a hundred grand a month selling cookies to their local town and he's doing all this cool tech stuff. And they have 50% margins too.

So they're living a really good life and it's not just your traditional idea of a business, you know? He's trying to make his community better. He's trying to make his life better and he's not stressing over how fast can we grow and how much bigger can we make this? He's thinking about, what do I like to spend my time doing while at the same time, he's kind of getting rich and making everybody feel good.

David Rosenthal 33m 42s

Oh, that's so cool. That's what I think is just so cool about this and why this is like, I think this is such a big movement alongside the traditional startup race venture capital, be something big right off the bat. Because the economic generation, activity generated by this class of entrepreneurs, is probably, in aggregate, going to be equal, if not larger...

Courtland Rosenthal 34m 9s

Totally.

David Rosenthal 34m 9s

...like the Rockefellers of the world.

Courtland Rosenthal 34m 12s

Have you ever, did you guys watch that series “Chernobyl”? It was on HBO last year.

Ben Gilbert 34m 15s

Oh, so good.

Courtland Allen 34m 15s

Great series.

Ben Gilbert 34m 16s

I heard about it, but...

Courtland Allen 34m 17s

It was good. They timed it so like right after “Game of Thrones” went off the air, they're like boom, here's another series. Don't unsubscribe from HBO. But they kind of boiled down the entire story, the work of this one scientist. And it was an amazing story, it was great.But obviously in real life it was probably dozens or hundreds of scientists and engineers working together try to figure out how to contain this nuclear disaster. And the reason why they did that is because it's just easier to tell a story about one person and it's the same in business, it's easier to tell the story of one company.

We're all fascinated by how big Apple is and the impact that Apple has or, you know, McDonald's is crazy. They have 20,000 restaurants in the United States. Cause that's the easy story to understand and to tell. But I think the much more impactful story is there are 600,000 individuals who have restaurants in the United States.

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 Indie Hackers 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 Amazon. They don't have a $2 trillion market cap, but what happens when a million people are building businesses and make millions of dollars online? Now, what does that look like?

Ben Gilbert 35m 25s

Not to mention, you know, 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 Indie Hackers continues to grow and expand and you figure out more ways to parallelize it, and at some point there's, you know, a hundred thousand stories of businesses and the playbooks that they run on your website. 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, you know, the one story that everyone focuses attention on.

Courtland Allen 36m 20s

Yeah, exactly. That's kind of the goal of a lot of the things that I'm building on Indie Hackers. How do you see these companies, like very early days, and then how do you filter down to a very specific niche so you find the company that most matches the profile of what you're trying to build?

And so we have this directory that I kind of haphazardly built two and a half years ago. And I was like, "Oh, we should have a directory of products." And I haven't touched the code in like two and a half years, but when I built it, it was, okay we have 50 people on it. And I checked the other day and it was 12,000 products on there. And they all have a little timeline where they're saying, "Okay, here's what I launched. And here's what I thought about my launch."

Ben Gilbert 36m 54s

I thought I was being ridiculous saying a hundred thousand, but it shouldn't be long.

Courtland Allen 36m 57s

No, it shouldn't be long. 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 not that different from you kind of put their playbook online.

Ben Gilbert 37m 10s

I love that. Take us from the light bulb of Taskforce should be making money to the founding of Indie Hackers. How did that period of time happen?

Courtland Allen 37m 21s

Yeah, I'll give you the whirlwind story. So at some point during the summer after YC, Stripe entered the beta phase. So this was 2011 and Stripe's, like, "Hey, you want to make money with their product, go for it."

David Rosenthal 37m 33s

They were before you, right?

Courtland Allen 37m 34s

They're before I was, maybe by a year or two. They took a while before they got their products to the point where it was ready, understandably, cause there's a lot of regulations dealing with banks and stuff. But, they kind of launched into beta and we got a good first look because we were kind of on the YC mailing list. So we threw up kind of a Stripe subscription and like maybe a day or two, just over a weekend.

And the next weekend, I think we made like $3,000 in payments, charging people five bucks a month for this crappy To-Do list Chrome extension. I thought we were going to make a hundred dollars or something. And I was like, "Holy shit. We can kind of pay our rent. We can pay for stuff with this." And so of course we went to the YC partners and were like, "Hey, look at this. This is cool. We're making a few thousand dollars." And they're like, "Yeah, but what if you were making way more and you had a different idea that wasn't a tiny Chrome extension?" Which in some ways, is good and bad, you know. In a 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 did what you should never do. We just completely started over from scratch with an idea that we thought was bigger and better. And we sort of violated that principle of taking it one step at a time. Probably over the next six or seven years, I started five or six different companies.

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

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 of my life, because I was literally just doing the same thing every single day. Now, my model that I have for it kind of frameworked in the way I think of it and the way I wish I had thought of it then was that everybody's kind of got like a certain number of companies that you need to start before you succeed. For some people who are exceptionally talented or lucky or both, that's just one. They're going to succeed right out of the gate. Some people maybe 35. For me, it was seven.

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

Nowadays, and eventually I kind of figured it out like, "Oh, I'm learning so much stuff. I should make sure that I'm really enjoying my life while I'm building stuff." So the last few years here, before I ended up starting Indie Hackers are actually really pleasant. I feel like I kind of leveled up as a person while I was building my startups, instead of just sort of, you know, worrying every step of the way. Like, “Am I there yet? You know, is it going to work? Is this going to be the one?”

Ben Gilbert 40m 25s

That's such a great lesson? And just like a couple of points of clarification. Were these all inside the same entity or is it different co-founders? Or how did that sort of tactically play out?

Courtland Allen 40m 37s

Yeah, 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 cleared up our YC startup debt. This is the end. I think I quit. And he kinda bought me out for my shares. And then I just kind of did my own thing. By that point I realized, what I need to do is figure out how to make this last. I want to spend the rest of my life just working for myself and whatever I like.

I don't want to go get a job. Part of it was I just didn't like the idea of having a boss. Me working at Stripe today is the first full-time job that I've ever had. I just don't like to be told what to do, I guess. And part of it was this, I don't know this pride of I don't want to have to interview somewhere. I don't want somebody to be able to reject me. I want to be unresectable. I don't want to ever put myself in a position where somebody could say, "No." And so, okay, I just want to keep doing this myself. I would just survive off of kind of my income from some of these apps.

Cause I would keep them running and they would make a few hundred dollars a month or a few thousand dollars a month. When I got low on income, I would just go get a contract job and then work on the side, et cetera, et cetera. And just kind of make it so I never had to quit, you know? And I think there's a lot to be said about startup failure. Okay, maybe your ideas fail because the market was too small or because you know, your product took too long to develop or you ran out of money. But my take on it is kind of that, none of those things actually kill your company, you know. Those are just obstacles, right?

So your market wasn't big enough. And then what? Right, like you quit? You didn't have to quit. Right? You could have, that's kind of like, if you imagine a startup journey, you being an early pioneer walking from the east coast to California, right? Those are just like obstacles. There's like rivers and mountains. You can kind of step over those and go around them or you can just be like, fuck it. I'm just gonna stop here and just live in Kansas, you know? And you don't want to stop and just live in Kansas. 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 start the next thing, which meant taking on contract work and building up my savings whenever I needed to.

Ben Gilbert 42m 25s

Yeah, default alive. Or I think at one point I ran a startup weekend in Seattle and Bo Lu, who actually, I think when I did YC with this company, Future Advisor and Sequoia funded it, he gave this great talk called “You're alive as long as you're not dead.” He was like, yeah, lots of things, bad things can happen at your company but as long as you don't shut it down, you have not failed. Your company is still in the act of succeeding. You're not successful yet, but you are on the act of succeeding until you call it quits. That's always stuck with me.

Courtland Allen 42m 53s

Yeah. And even if you do quit a particular company, I've quit lots of different companies, but as long as you don't quit your overall journey, you're still on that path, you know, you're still headed to California and you're going to eventually get there. Who knows how many startups it's going to take, but you'll get there as long as you're sort of learning and you persist. So I think the most important thing you can do is figure out how to keep going.

Ben Gilbert 43m 10s

All right. So the genesis of Indie Hackers, how did that happen?

Courtland Allen 43m 15s

I had 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."Take four. I'm gonna figure out something to work on that's going to work this time. Worst case scenario, it's going to all fail and I'm going to go back to working contract jobs. I started working on this one app that I called Knox, and it was kind of this meant clone for your phone that would buzz you with your finances.

Maybe two or three months into it, I was like, this is an endless slog of coding. This is going to take me forever. I don't see like the end of the rainbow. I need to just call it quits right now. At the time where I was working on that, I saw a couple stories on Hacker News that people who would come up with new ideas and we're already making five or ten grand a month, and 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 the drawing board and figure out what are all the different lessons that I've learned after years of doing this? Let me make sure I'm systematic in how I approach this so I'm not just going to make the same mistakes again.

I had repeatedly made this mistake that a lot of software engineers make where we just spend way too much time coding. I think the biggest lesson at the top of the list was only work on things and you can build in a few weeks. You know, I went from idea to basically launching with Indie Hackers 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. 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, you know, borrow money and go into credit card debt?

And the other lever of people pool is like, "Oh, how do I get more time? You know, maybe I'm gonna work nights and weekends and all this stuff. And I wanna work a 3-day workweek instead of a 5-day workweek. But I think the third lever that's probably the best is how do you just start smaller? How do you figure out what's an easy, even easier thing to do? And for me, my idea was, okay, I want to build kind of an Indie Hacker business so I can sort of, you know, pay my rent, pay my bills, and then figure out what I want to do next. A ton of other people clearly want to do this.

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

That's not necessarily in their stories. If I can compile all of the stories that I found and tell them in a really compelling way, I make sure I always ask for revenue numbers. I always ask for how they come up with their idea. I always ask about technical details and I can put that in one place. Then I'm making life easier for both me and a bunch of people who were like me, who were trying to figure out how to be Indie Hackers themselves. So that was kind of my idea, kind of 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, you know, get their information, put it on a blog and launch it. And I'm a hundred percent sure people are anachronistic and eat it up because they've already been eating up stories like this before.

Ben Gilbert 46m 3s

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 envisioned in my head. I know the scope. I know how to build it. I think people are going to love it, but it's a project.

Courtland Allen 46m 14s

A hundred percent is going to be a business. I don't know how I'm gonna make money yet, but it's a hundred percent, at some point, I'm going to start in this really small pool, you know. I'm going to 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. Maybe we'll have an audience. Maybe we'll have a lot of traffic. Maybe we'll have a big mailing list. And then from there it should be easier for me to figure out how to make an actual business.

David Rosenthal 46m 36s

The revenue aspect, maybe revenue and profit aspect of the stories you were telling, was that super key? Cause I can imagine like, you know, when you're trying to find like, oh yeah, you're just talking all this game about like how great it is, all the stuff he did. But is it actually working? You know, give me, that feels almost like the Zestimate before Zillow, right? Like, you know, it's like, hey, this house looks good, but what's it worth? How important was that?

Courtland Allen 47m 5s

It was extremely important. If I could write a startup book, I would call it “Problems First,” where the first thing you want to do is you want to figure out what are the problems that your potential customers have? So you don't build like some random product that doesn't solve their pain points. And when I was reading all these comments on Hacker News, I was trying to find a business idea. I didn't want to read comments from people who 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's really great, you know. It does this and this and this,” and they don't share their revenue numbers. For all I know they're making like $5 a month, you know, and it's not that great.

I can tell everybody else in the comments, had kind of the same problem. They were like, "Hey, we only want to upvote the stories that share their revenue numbers. We only want to upvote the stories that have some sort of proof or some sort of inspirational thing that we can grasp onto to know this person is legit."

Ben Gilbert 47m 49s

And to have a closed cycle that this advice worked. This advice is trustable.

Courtland Allen 47m 55s

Right. Yeah. Anybody can give you advice and tell you what to do, but if there's no outcome, a result of that advice. You don't know if it's good.

Ben Gilbert 48m 0s

Train your model on garbage data.

Courtland Allen 48m 2s

Exactly. And so, that's a thing where there were a lot of other interview sites on the web that talked to entrepreneurs. They're pretty much none at the time that realized how important it was. You need it to be transparent, you need to include revenue numbers. And so when I went out and I started emailing people and saying like, "Hey. My name is Courtland. I'm starting this website that is going to be called Indie 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 never 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, you know, did the same for me in the past." By the time I launched, I think I had gotten 10 people to agree to share their entire story and their revenue numbers.

David Rosenthal 48m 44s

That's awesome. And so how did you, when you launched, you built the site, right? So you didn't go to Squarespace, didn't go to Webflow. What was the thinking behind that?

Courtland Allen 48m 55s

Yeah, so I had a couple sort of reasons for that. Part of it was, I had a bunch of other ideas that I had come up with in my brainstorming and Indie 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 this software developer, I'm building all these other startups. I learned so much stuff from building startups over the years and failing time and time again. I learned how to design, and learn how to do front end development and backend, and server admin stuff.

And here I was like going to sort of blog. So, I was like, wow, this is such a waste. I want to throw myself some kind of bone to make this fun because starting a company should be fun, you should enjoy the journey, not just the destination. And so I said, "Okay, well, I'll do a blog, but I'll allow myself to just build 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. I'll allow myself just that little bit of fun." And then part of it was kind of a branding and strategy play.

David Rosenthal 49m 45s

So you weren't yet thinking like Stripe revenue connect?

Courtland Allen 49m 49s

No.

David Rosenthal 49m 49s

You know, building a community?

Courtland Allen 49m 52s

That was kind of in the back of my mind, the community stuff. Definitely not the product directory and Stripe revenue stats or like a lot of the stuff that exists today. But I did have kind of a strategic sort of session with myself. So I spent one day just thinking strategy, cause in the beginning of your company, there's a bunch of decisions that you make that are much harder to undo later on. You'll tell yourself like, "Oh, I’ll use a crappy design now and redesign it later."

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

What do I want the color scheme to be? How do I want the site to work? What do I want it to be called? And kind of the three decisions that I came to you where, number one, I want the site to be named after a new class of people. Because I was like, well, there's no name for these people and these discussions. It's really hard for them to find each other even because what are you even searching for? Like the story of a person who bootstrapped a startup and makes 5,000. There's nothing to search and so hard to find. So I was like, I'm going to call it Indie Hackers. I had a bunch of worse names, but Indie Hackers is the best one I came up with.

I decided I wanted to make the site blue. So it's like this very dark blue color that's probably not very accessible and kind of hard to read, but every other site in existence was just like white with black text. Everybody was writing on medium and all looked the same. And so I wanted mine to stand out so that if you ever read two Indie Hacker stories, you would instantly remember that you'd been to this website before. And then I wanted to do it custom because I just didn't want to build on somebody else's platform. I didn't like the platform risk. I've been kind of burned by that before building on Gmail and, you know, they would change their API all the time and kind of break our apps.

I didn't want to deal with 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 were the three decisions I made back then and all of them, I think, turned out to be pretty good in the long run.

Ben Gilbert 51m 40s

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 Hawkin Barry, and a bunch of the icon factory people, they were saying, "Oh, I'm an indie developer, indie you know, iPhone or Apple developer."

And obviously Hacker News was sort of a thing, but those communities were basically non-overlapping. Hackers were what people who were technical and wanted to start high growth technology startups refer to themselves as, but indies were what the lifestyle developer community primarily centered around Apple platforms kind of called themselves.

Courtland Allen 52m 23s

Yeah. And I wasn't thinking about honestly any of that, anyway. I wasn't even aware that they were indie developers. I was just like, "Okay, well, I want the idea of an independent programmer." Because again, it wasn't so much a rebellion against raising money. It was a rebellion against going to work for the man, and making Google $10 million a year from your code, but you're only getting like 200K of that, you know. Why don't you start your own thing and be kind of your own Indie developer?

Hacker News was so-called because hackers are just another word for programmers. So the idea is, okay, you're a programmer, but you're independent. There's no cap on your salary. You know, there's really no limits, you can do whatever you want.

Ben Gilbert 52m 57s

Yep. And before we move on from this point, talk to me about platform risk. Because in my mind, you know, we think about this for Acquired too. We're always trying to get the most direct relationship possible with our listeners, with our LPs, with our, you know, with everybody and there's always some platform risk.

We've collected email addresses from one outta, I don't know, six or seven listeners, you know, from all the various reasons that people join our Slack or they sign up for the emails, which, you know, now have the playbook, so there's even a further incentive to sign up for the emails. But at the end of the day, even if you have someone's email, you know, you could go to their promotions tab. You never, it's not like you can call that person, you know? It's not like, there's always some amount of indirection between you and your end customer. So, how do you think about how far you should go on eliminating platform risk?

Courtland Allen 53m 50s

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, like never built on a platform, right? If you're building a platform, maybe they can give you additional distribution, but then you get the risk that they might shut you down or change things so you might lose out on the branding or ability to differentiate yourself, et cetera.

Maybe you can charge a high amount of revenue per user, but that means you're going to get, you know, maybe fewer users in the door, fewer customers, but then also you can spend more to acquire 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, 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 kind of 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, like how much did Medium really helped at distribution? It was kind of hit and miss. They would also just completely 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. I wasn't sure, but I knew that if I was going to name it Indie Hackers, go for something where the brand actually mattered, which I think is important, if you're going to have something where it's kind of free and I'm just getting lots of users in the door, but I didn't have a business model that I wanted to own my brand. So it wasn't worth it for me to use any of these platforms, even though they would help at distribution, if I could instead just do my own.

I also had kind of my own distribution strategy. I already knew that people were going to be eating this kind of stuff up on Hacker News because they already were. And I already knew that Hacker News had a lot of traffic, so it's like, okay, I don't need Medium. I can do it on my own. So, I get no real benefit from Medium and I get all this additional risk, the trade off just wasn't worth it.

David Rosenthal 55m 26s

Yeah, it's got to put it in some ways you maybe ran the Airbnb playbook of exfiltrate Craigslist did for this segment of Hacker News.

Courtland Allen 55m 37s

Yeah, my buddy, Greg Eisenberg has this whole idea of, you know, unbundling Craigslist, unbundling Reddit...

David Rosenthal 55m 43s

Yeah.

Courtland Allen 55m 43s

Unbundling Hacker News. It's a huge community. There's all sorts of sub discussions happening in there that happen regularly.

David Rosenthal 55m 48s

Totally. It's a pretty big tent.

Courtland Allen 55m 50s

Exactly.

David Rosenthal 55m 51s

Okay, so you launched, you built the site, launched the blog on your site. As I understand it, pretty quickly you figured out that email was a pretty big unlock kind of both for the interviews you were doing, call it the supply side of these stories, and for readers for the demand side, too.

Courtland Allen 56m 13s

Totally. You can almost imagine the web is like this collection of feeds or like destinations, and some of them are places where people go habitually. I habitually check my email. I habitually check the notifications on my phone. I habitually check Twitter. I'm just addicted, I'll sit down and just press T on my keyboard and blackout for a second I'm on Twitter.

And then there's other places where people just don't have a habit. 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. I was publishing once or twice a week, you know. Twitter has got new content every single minute.

So, for me it was, okay, well, how do I hook into one of these feeds that everybody already habitually looks at? And it was a combination of both Twitter and email. I made the Twitter Indie Hackers account, I tried to tweet every story that I had so that you would sort of accidentally run into them when you check your Twitter and be like, "Oh yeah, I remember Indie Hackers. Let me go back there."

Email was a huge one cause 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 of every interview, just trying to get people's emails. And I think in the first week we got 1,015 hundred emails and it kind of continued on that pace for a while, a thousand emails a week from people from Hacker News and all over the web who just loved these success stories. They would come and read them and they would be so inspired to hear that, you know, so-and-so is making 10 grand a month from their travel startup and I'm a developer. I could do that too.

And so they would immediately get on the email because they want more of these stories, you know, they want more glances, like what's possible. So that when the day comes that they're ready to start their startup, they haven't forgotten where to go to see those examples.

David Rosenthal 57m 49s

You got to have some reason that you're going to show up for people.

Courtland Allen 57m 55s

Totally.

David Rosenthal 57m 55s

Well, one of the things, you know, I kind of joke about it. I don't know. There's no way to scientifically know, and we didn't plan it this way, but the fact that, you know, this podcast, our podcast name is ACQ, in almost everybody's podcast feed we are at the very top because for whatever reason, I guess, feeds are organized alphabetically. And how much benefit have we gotten from that? I don't know, but I'm pretty sure...

Courtland Allen 58m 19s

Probably a lot.

David Rosenthal 58m 19s

We get a lot.

Ben Gilbert 58m 21s

We get at the top of an accidental feed, which is the podcast player.

David Rosenthal 58m 25s

Yeah. If we were farther down below, yeah. I don't know.

Courtland Allen 58m 30s

Yeah. And it's a hard one lesson for a lot of people who are starting startups. If you're an Indie Hacker, you don't have a bunch of investors and mentors. You probably just kind of by default believe , you know, 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 building stuff is kind of easy, even if you're not a developer today, you can stitch stuff. I talked to a guy yesterday who built a whole Slack bot without using code at all. Didn't even know how to code. The hard part is getting people to actually care about what you're building and actually find it. So that means you have to actually...

David Rosenthal 58m 59s

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

Courtland Allen 59m 0s

Yes, I'd ran into it.

David Rosenthal 59m 1s

And it's not just running through it once, it's running into it several times.

Courtland Allen 59m 5s

Repeatedly and that's very hard to do. But if you think about it really carefully before you start, then often you can come up with something. What I found is helpful is you just go to one of the places where people find things and you just look at what they're sharing. You know, that's kind of accidentally what I did with Indie Hackers. I was already in Hacker News and it took like days of me reading these threads before it clicked like, "Wow, everybody is here sharing this thing. Why don't I just make my thing better than what they're sharing here and then share it in the exact same place."

Ben Gilbert 59m 31s

Okay. So we've talked about this insight that you had that enabled growth. So, you know, we sound like a circa 2011 YC, you know. Tell me about your growth rates. Now let's shift to the Indie Hacker conversation. How did you start making money?

Courtland Allen 59m 46s

Yeah, so actually what happened is my very first sort of head of revenue was completely unexpected. It was 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 how much traffic do you have?" And I told them, "Sure, we'll give you like 750 bucks a month." And that to me was insane because everything that I had ever built was some rinky-dink consumer app where I was begging people to pay me five bucks a month. Yeah, pennies. And people were, “Well, no, it doesn't have this feature. I can't possibly afford $5 a month,” and then they'll go buy a bad coffee and dump it out. You know?

So this company offering me hundreds of dollars, it was a wake up call like, "Oh, I can make money from sponsors." But I was also super focused on growth. Cause 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 and not worry about money and I'll worry about it later. So I did that for three months. I just kept trying to grow the site. I didn't figure out how to grow the site at all. I never found something that was bigger and better than getting on the front page of Hacker News, go figure.

By December, I launched in August, and by December I was like, "Okay, screw this. I'm going to start trying to make money." I started basically emailing my list, which at that point had probably been grown to 10 or 15 thousand people and saying, "Hey, you know, here's the email with 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...

David Rosenthal 1h 1m 20s

Literally, it's the billboard that you see with the your ad could be here?

Courtland Allen 1h 1m 23s

Yeah. It was exactly that, but in email form. And I put that on the website too. It turns out when you have a company that targets people who are starting companies, you have a lot of potential advertisers on your mailing list, who all want to basically advertise with you. 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. If they were going to spend like $500,000 on an ad, that added better work. That's like their whole yearly ad budget.

David Rosenthal 1h 1m 56s

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

Courtland Allen 1h 2m 1s

Almost like that. So I went through a lot of these awkward conversations where I'd run ads for people. And I just wanted to do right by them. But the ads didn't always get enough clicks and sometimes I would refund people. It was just very stressful. I didn't like doing it. And so I created a kind of a dream list of companies like, okay, which companies actually have a lot of money that would be good sponsors?

I've no experience doing sales, but I'm going to have to figure out how to do this. And I had at the very bottom of my list, my number one dream company who should be sponsoring Indie Hackers was Stripe. I'm like, okay, I'll eventually get to them, but I want to figure, I want my shit to get good.

Ben Gilbert 1h 2m 33s

Get some warm ups in first.

Courtland Allen 1h 2m 34s

Yeah. I need some warmups, you know? And so I...

David Rosenthal 1h 2m 36s

Done warm up on Broadway.

Courtland Allen 1h 2m 37s

Exactly. You don't want to embarrass yourself in front of everybody. So I got some warmups. I sent a lot of cold emails. I found the heads of marketing on LinkedIn. My buddy, Jeff, who ran a podcast I was on, gave me kind of his list of leads, where he was advertising on his podcast.

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. They would just want to talk about their kids, talk about their vacations, and they'd be like, "Oh yeah, you're cool, here's a check for five grand. And I'll be like, "Holy shit. This is a thousand times easier than selling to people who were broke."

Ben Gilbert 1h 3m 10s

Yeah. And not to mention, you know, one of my key startup lessons learned over the years has been to 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.

Courtland Allen 1h 3m 33s

And I think that applies to even coming up with startup ideas and trying to figure out a business model. It's kind of counter-intuitive because people repeat this mantra, you know, 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 kind of insert yourself there.

My friend started a company called Key Values. She's been one of my best friends for years. Her name is Lynne and her company, it helps startups hire engineers. And you know what, startups are hiring engineers just fine well before her company came along. But we kind of picked that idea because we looked at where a company is spending money, you know? Where do they spend a lot of their money?

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 into a hundred grand a quarter. She was living a great life. It just actually, she made it look easy her first time out of the gate and part because she picked a problem where people had budgets.

Ben Gilbert 1h 4m 28s

Right. I think the insight here is if you really want to overly simplify the sales process, there's educate and then win. Educate people that their need is real, and then once they are convinced that they want to solve this problem, then go win and be the way that you solve that problem for them. 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.

Courtland Allen 1h 4m 51s

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

David Rosenthal 1h 4m 58s

Or more frequently you educate somebody and they're like, "Eeh, still don't get it."

Courtland Allen 1h 5m 1s

Yeah, right.

David Rosenthal 1h 5m 1s

"I've got these other things that I need to solve."

Ben Gilbert 1h 5m 4s

All right. So Broadway comes...

David Rosenthal 1h 5m 6s

Then you get a particular email.

Courtland Allen 1h 5m 9s

Yeah. I don't know, I'm selling ads for a few months. I'm just happy to be honest. Cause I got to the point, I think in February of 2016 where Indie Hackers is going to pay off my bills and I was like, "Wow, in less than a year, I've gone from, you know, nothing to finally one of the ideas I've done works, you know?"

David Rosenthal 1h 5m 25s

So none of the other companies you'd worked on you'd gotten to this point where it's like...

Courtland Allen 1h 5m 28s

No.

David Rosenthal 1h 5m 29s

...revenue is covering my personal expenses.

Courtland Allen 1h 5m 31s

No. And it was better in literally every single way. Eventually, I had added a community and so people were sort of talking to each other. So I began to see kind of a path where like, "Oh, I can do less work. Maybe people can interview each other and I don't have to do anything."

And people really liked it. You know, it was very, I wasn't making to-do list software where all I got were angry customer emails cause I don't have the right feature. Every email I got was something positive, people talking about how inspired they were by an energy that they heard. It was just 100% good for my life in every single way. I was just blown away and super happy and just high on life. Then to make things even better, I get this email out of the blue. And so, I hadn't gotten to Stripe yet on my sort of list of sponsors to reach out to.

David Rosenthal 1h 6m 9s

And you weren't in the same batch, you didn't know them.

Courtland Allen 1h 6m 12s

No, I think during the Stripe beta maybe gone in there, look a little Stripe chat room and, you know, pointed out some bugs and ask some questions. But I had never really talked to the founders outside of that. And the email, I just stepped off a plane, actually. I was going to a buddy's bachelor party in Mexico. I stepped off the plane, I was checking my emails and the very top of the inbox was "Acquire Indie Hackers?" from Patrick at Stripe. And I was just like, "Holy shit. There's no way this email is real. I mean, it's completely..."

David Rosenthal 1h 6m 38s

You're getting trolled.

Courtland Allen 1h 6m 39s

Yeah. I'm definitely getting trolled. But I read it and it was real. And he was just kind of like, "Hey, Courtland, really admiring what you're doing at Indie Hackers, you know, is there any way it would be open to Stripe potentially acquiring it?" And so the first thing I did was I forwarded it to my mom, sent to my brother, sent to my friends.

Ben Gilbert 1h 6m 55s

It's the Paul Graham email all over again.

Courtland Allen 1h 6m 57s

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

Ben Gilbert 1h 7m 9s

All right. So 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."

Courtland Allen 1h 7m 37s

I think it was a combination of both. It's been funny looking at just acquisitions over the years, talking to friends and also seeing like a little bit of stuff internally at Stripe. It's just so idiosyncratic and almost random how these acquisitions happen in many cases where it was just depending on how a particular person feels, this seems the thing to buy. I think in my case, Stripe has this kind of cool project internally, collecting the crazy ideas list. It's, "Hey, everybody, write down the craziest ideas, if it's a reasonable idea, it's not allowed on this list. You need to write down just crazy things that we could potentially do that might win big."

I think some version of Indie Hackers had been on that list for many years. You know, what if we have a community for early stage startup founders. Just because we're a company like Stripe that wins a lot of business from early startups, these startups grow and they might be making a thousand dollars a month now, but five years from now, they could be Lyft.

And so like winning, the hearts and minds of early stage startups matters a lot. And so that idea was on there and they just never did it. Cause there's maybe a thousand ideas on that list. And then I started Indie Hackers, it just worked, it worked really well. It just happened to very luckily, perfectly align with what they wanted it to do.

Where it's like, okay, well it's like empowering people to get started and inspiring them. Stripe is a company that cares a lot about it's reputation. It's not an accident that Stripe hasn't had, you know, any sort of major scandals, like almost every other huge unicorn company. It's because the founders care a lot. We have a lot of good, well among founders and developers and make a lot of decisions at the company that are or, you know, have that in mind, it's to do best by people. Indie Hackers was also a huge check in that direction where people just really liked Indie Hackers.

They liked the positivity, liked the optimism. It was all about how you can do it, you know, how you can kinda stick it to the man and start your own business, it was very empowering. 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 Stripe that clearly wants more businesses to exist and more businesses to succeed.

Ben Gilbert 1h 9m 37s

What were some of your concerns once you started, after you got out of the initial wave of, "Oh my God!" Then you're like, "Wow, would I sell this? Should I sell this?" How did you think about some of the trade-offs and tensions there?

Courtland Allen 1h 9m 50s

One of the things that was weighing heaviest on my mind was I just really didn't like selling ads. I was really not having a great time. I mean, I was making money. It was fun to get checks. But I wanted to make Indie Hackers bigger and better. I wanted to spend a lot more time coding the community. At that time, the community only had maybe 40, 50 conversations a week. Now it's got tens of thousands and I just wanted the time to do that. And so I was thinking, "Okay, well, if I go to Stripe, what are they going to have me working on? You know, how much say are they going to have in what I'm doing? And how much does their vision align with what my vision is for the company?"

If it's off by even a small amount maybe that's not a big deal today, but four or five years from now, that could be a huge deal. A small gap can turn into a really big gap. And so I really wanted to know like, okay, are we going to be aligned? I wanted to know, cause that's kind of for the betterment of the community, the people at Indie Hackers, is this going to be good for them? You know, if you have a community and you have something where all your users are quite vocal, especially if they come from Hacker News, which most Indie Hackers did, these are opinionated people.

They don't tend to look kindly on acquisitions that go wrong and watching their favorite products die. So I wanted to know, okay, is Indie Hackers going to be better off for this? I wanted to know if I was going to be better off from this. You know, how much money is this acquisition going to make me, right?

David Rosenthal 1h 10m 59s

That's the whole point of Indie Hackers, right?

Courtland Allen 1h 11m 2s

Exactly. If I'm gonna no longer be sort of technically indie, you know, what is the trade off I'm making? And how indie will I be? I have this whole point that I make to friends. It always gets a mixed reception, but I think everybody's kind of a business, even if you're an employee. You should think of yourself as a business.

Ben Gilbert 1h 11m 20s

Totally.

David Rosenthal 1h 11m 20s

100%

Courtland Allen 1h 11m 20s

Anytime money changes hands, you should think of yourself as a business. If you want to learn how to improve your career, read a business book and think about yourself as a business. And so, you know, as an employee, yeah, you might seem like you have no power, but I learned from contracting you have a lot of power.

If you can make the value or the service or product you provide to your employer really unique, it's harder to fire you. You're more valuable. You can get paid more. You can get paid what you're worth rather than being paid very little because you have so many competitors of the exact same job title as you. And, you know, some of the other parts of the employee experience relate to being a business. You know, everybody has marketing experience. If you've ever made a resume, that's basically an ad. And when you've shipped it out to, you know, potential employers, that's basically marketing.

If you've done an interview, you've done sales cause you're trying to sell yourself. So I thought about myself in that light. Okay, well, how much freedom and independence am I going to have as an employee of Stripe? Who am I going to report to? What are they going to be telling me to do, if anything? And I think the kind of...

David Rosenthal 1h 12m 13s

I’ve gotta imagine, even though this idea was on the Stripe crazy ideas list for a long time, probably the reason nobody ever did it is you got to focus on it until you do it. You can't be pulled in like, "Oh yeah. I know you're doing this thing. Right? But, hey, we've got this bug. Can you just jump in and fix it or, you know, we gotta do this thing. You know, you can get back to doing that thing, but we gotta do this thing.” That's probably on your mind, right?

Courtland Allen 1h 12m 35s

It's also like a completely different type thing. The average sort of engineer, a bigger startup is not someone with a lot of startup experience. You know, there isn't a roadmap for here's how you start a large community of founders. There's no step-by-step process. It hasn't really been done before. For some reason, there just aren't large communities of founders that have really thrived online. And so it's kind of easier to wait for somebody else to do it than it is to pick a random employee and be like, "Good luck!"

David Rosenthal 1h 13m 0s

We're going to go make you a star.

Courtland Allen 1h 13m 2s

Yeah, good luck! I mean, some people can do it, but that's not why people typically apply to jobs. Cause that's, you know, if they want it 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 a normal Stripe employee or not? And then sort of the third box besides just like me and the community was what does Stripe want to get out of this?

I really wanted to know what Stripe wanted to get out of it because it's hard to predict, you know, if we're going to align, if I don't know why you're even doing this. And to Patrick and the leadership team's like credit, they're just very open-minded folks, you know. They don't necessarily need a ton of proof that something's going to work.

If something is directionally pointing in the right direction and it can work, they're more than happy to take a chance. With Indie Hackers and Stripe, it's kind of Indie Hackers doesn't really capture a lot of the value that it creates. You know, if people start companies and their companies succeed because of Indie Hackers, or because of a story they heard, and because somebody helped them on the community, how do I make money from that? It turned out I didn't.

But other companies do this that can capture that value, including Stripe, because Stripe is the best product in the market, what are they going to use for their new companies? They're going to use Stripe. Patrick really just trusted like, "Hey, we think that you can make Indie Hackers really big and really meaningful. You've done a great job so far." It's hard to even measure it. Even if you do make it big, we'll never really know exactly how much it's contributed and sort of added wind to our sails, but that's fine.

Ben Gilbert 1h 14m 18s

And so a couple of questions here and I'll ask them together so, you know, both are coming. The first one, 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 things really 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?

Courtland Allen 1h 14m 52s

Yeah, these are tricky questions. And I never feel the most qualified to answer acquisition questions. Even though this is Acquired, people call me all the time like, "Hey, I'm going through an acquisition and you went through one, what happened with you?" And I'm like, "It's so specific to my situation..."

David Rosenthal 1h 15m 4s

I had no employee.

Courtland Allen 1h 15m 6s

Yeah. I was a solo founder with no employees, I hadn't been incorporated. But there's some little tricks and things that helped me. The first thing that happened was that Patrick suggested that we communicate over text. So we got on WhatsApp, which instantly I was like, "Oh, this is so smart." Because I had been sitting there, I think it was a Sunday, typing out an email, this sort of acquisition numbers negotiation.

And it was such a high pressure thing. What am I going to say in this email? Versus texts, it's just so casual, it just kind of fires off messages and it just lowers sort of the stress and almost the adversarial nature of it in the long run, in a strong way. So that was kind of the first tip. But then I thought about, okay, well, how do I value what Indie Hackers is worth? What am I going to be happy with here?

And I think your first question was also how much does trust come into it? So the first thing I started doing was trying to answer both of these questions actually through 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.

And I'm like, "Hey, what kind of person am I dealing with?" And I got a lot of really positive stories. This is a person who cares deeply about what's good for people, et cetera, very ethical, et cetera. I think you need that level of trust because in a contract, as I soon found out, there's just so many random loopholes and edge cases that you haven't considered and just really easy ways to get kind of screwed over.

At some point, I was talking to Patrick and we were hammering things out and at one point I got an email that, it wasn't from Patrick, it was from Stripe general counsel. And I'm like, "Oh shit. Maybe I should have a lawyer because I don't know what these guys are talking about." So then I went and hired a lawyer and her name was Metalla. She was great, but she was just the most paranoid person ever.

She was like, here are all the ways they're gonna screw you over. They're going to do this. They're going to do that. They're gonna do this. Every single contract that came, she found some way to tighten up the language or just go to bat for me in ways where, because I had a lot of trust, perhaps naively, I just would have been like, "Oh, that's fine. They have the best intentions here."

And so it's kinda, you know, trust but verify. I had a lot of trust and I don't think I would have done the deal if I didn't trust that everybody involved was being sincere with what they said, that their sort of thoughts align with their actions and their words. But also having someone in my corner to make sure that these things wouldn't happen was I think important and gave me a lot of security.

David Rosenthal 1h 17m 21s

Well, the thing about this, situations like this is the documents and the clauses and all that, they exist for when things go sour, you know. Anytime you are looking at those documents, things are on a bad path, you know. You don't ever want to look at them.

Courtland Allen 1h 17m 40s

Yeah.

David Rosenthal 1h 17m 41s

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

Courtland Allen 1h 17m 48s

Exactly. So they're important and they matter. And I think in my situation, what kind of happened is that we agreed on numbers, but in a very high level, non-specific, this is what would make us all happy way. And that happened pretty quickly, it didn't take that long. And part of that was also doing research, how much the engineers at Stripe get paid. Can I, you know, by that point I was pretty good at getting people to reveal numbers to me from working on Indie Hackers, so I got a lot of numbers.

I was like, "Okay, look, this is what I want." And I was trying to be a firm negotiator. But you kind of agree on these numbers and then you go to drop a document and it turns out there's just a million little edge cases, you know? For example, if we're talking about stock, what kind of stock do you want? What class, when does it vest? What period does it vest? Like how long? I had to refresh this work, all sorts of different things that I think if you're kind of a typical employee, you might not consider, but if we're coming in through an acquisition, the sky's the limit.

You can ask for or demand literally whatever you want and put it in a contract, that's going to be your special contract that no one else at the company has anything that's even that. So, for me, it wasn't just a kind of worst case scenario. It was, okay, well now is this whole phase two of negotiations. Or, talking about all these little details that we hadn't even considered.

Ben Gilbert 1h 18m 53s

Yeah. I'm curious. What mechanics did you put in place? Obviously it wasn't like, okay, here's a bunch of cash. Welcome to Stripe. Like it's either stock or it's vesting, or it's tied to incentive-based targets for Indie Hackers, or it's tied to Stripe as a company rather than Indie Hackers. How did you sort of structure the way that there would be incentives over time for both sides?

Courtland Allen 1h 19m 18s

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

Ben Gilbert 1h 19m 21s

And 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.

Courtland Allen 1h 19m 30s

Yeah. 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 of numbers, you know, this company sold for X amount. But in my experience, rarely how it happens. It's rarely that simple. Some of the other options are just much more advantageous.

Often companies will give you more equity than they will give you cash. If you can sort of evaluate the company, if it's Stripe, for the love of God, take the equity, you know. If it's Groupon and I don't know, you know, maybe you want the cash and this is an exercise.

David Rosenthal 1h 20m 5s

This is the difference, I think, between, you know, like Salesforce buys Slack, it's about the number, right? Because it's a company bank, it's a corporate entity buying a corporate entity. With an Indie Hacker business, no, it's you, you know.

Courtland Allen 1h 20m 17s

It's literally you. I don't know what, like Elon Musk's situation is, but he has all these weird earn-out bonuses where he gets more money if the stock price goes up. So even in those big companies situations, there's all sorts of ways to sort of figure things out. If Salesforce buys Slack, what does that mean for Stewart Butterfield? Perhaps he can say like, "I want more money if we hit these extra targets, et cetera." And perhaps Marc Benioff would be like, "Sure, that's fine."

And so I think if you can think about kind of these creative ways to sort of 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, cause 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, you know, they're sort of on the hook for more money in the future. In my particular case, it's funny because Indie Hackers is very much an Indie Hacker business. You know, I was just making money from advertisers. I have some affiliate links on the site.

I think it was making seven and a half, $8,000 a month by the time Stripe acquired the company. Whereas like today, I feel much more like a high growth startup, where Stripe owns Indie Hackers, but they're almost kind of an investor. And my goal is to grow as much as possible. And I don't make any money, Indie Hackers doesn't have any sort of revenue we bring in and we have kind of a budget, which is almost like funding to help us grow. And so it represented kind of a complete change in how I viewed growing my own business. I kind of went to this, almost to the exact opposite of what the stereotypical and Indie Hacker company is trying to do.

Ben Gilbert 1h 21m 40s

It's an interesting, 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, you know, changed it to sound like an English word to get the point across. Anyway, what differences do you notice between Indie Hackers, which is a wholly-owned subsidiary of Stripe, and I'm sure that 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.

Courtland Allen 1h 22m 14s

Yeah. I mean, I think branding is by far the biggest difference, because it's pretty obvious to most, most people who are aware of Indie Hackers know that Indie Hackers started before Stripe. And they know that it's kind of my thing, I'm very transparent. They're gonna listen to this podcast and be like, clearly Courtland is running this on its own.

You know, this is not like a super heavy-handed Stripe initiative. Plus like a lot of people don't even know Indie Hackers is owned by Stripe. There's a very small, little logo that says, etched 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 kind of ran the Stripe Atlas community, got an email from Indie Hackers. He's like, "Oh my God, you send fuck in an email, like a Stripe email." And I'm like, "I’ve said fuck in probably a dozen of these emails."

There's no way that Stripe is kind of monitoring that, you know, there's a lot of trust that goes both ways. I trust Stripe and they trust me and it doesn't, you know, it's weird in a way, I feel a lot of the positive things and feelings people have about Indie Hackers sort of get accrued to Stripe, but some of the riskier decisions like don't weigh on Stripe at all.

So it's almost the best of both worlds, whereas I think if I started some Stripe product internally, like Stripe Press, that has Stripe's name, literally in the name, which means it's a certain level of quality that it has to rise to. There's a certain standard that has to rise too. It's harder to get things off the ground when you do that, you need to match certain accessibility standards and have a certain reach of people in different countries and have all these other languages.

I think it's just harder to iterate on any sort of startup-type initiative that is trying to find product market fit if you have all of these expectations on you. This is why I think it's smart for Google when they're doing their innovations to try to spend things out of the Google brand and just have them be dissociated so people don't have these expectations cause you just kind of need to start with something embarrassing and rough.

David Rosenthal 1h 24m 1s

YouTube's a great example, right? When Google bought YouTube, there was still, the Viacom lawsuit was going on, there was all sorts of, you know, people were up in arms. There's crazy stuff happening. There still is crazy stuff happening on YouTube. Although now it's like...

Ben Gilbert 1h 24m 16s

Google video was a failing product. It was trying to do the exact same thing, but was going through Google standard.

David Rosenthal 1h 24m 23s

Yeah, they weren't going to just put movies up on there that were filmed with a camcorder in a theater.

Courtland Allen 1h 24m 31s

You can take bigger risks through an acquisition, especially if you have an established brand on its own.

Ben Gilbert 1h 24m 35s

That's really cool. All right. So tell us now why has it made sense for Stripe and I mean, this is a little bit of a softball question, but how's it going? How has it gone? Was it a good idea for Stripe to buy Indie Hackers? What have you built to do any integrations if you have?

Courtland Allen 1h 24m 53s

Yeah. So, I mean it's worth noting sort of my working style at Stripe is that I reported to Patrick since I got here. We don't meet all that often, you know. There've been years we met twice, or years 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 Indie Hackers, literally everything that I've done has been 100% my choice. There's not been a single request from Stripe saying, "Hey, can you do this?" that’s happened. So a couple of things have happened since we joined Stripe. I remember meeting Patrick maybe nine months after the acquisition.

And he was like, "Oh, this looks really good. I was kind of worried that for you to grow, you sort of have to just kind of run faster and faster." Because when Stripe acquired Indie Hackers, it was still primarily just kind of a media company. We're doing nothing but putting out these interviews. We had this very fledgling community forum, but it was like you have to click a link to get to it and it was only a small number of people. Whereas today the bulk of what happens on Indie Hackers is sort of user powered. It's more of an actual platform where I'm not doing, the vast majority of value that Indie Hackers creates in the world does not come from me.

Ben Gilbert 1h 25m 53s

And you did it. You shifted from a media company to software product.

Courtland Allen 1h 25m 56s

Exactly. Which I always wanted to do, but it took, Jesus, did it take a long time. Probably I would say the biggest accomplishment since joining Stripe was just the growth of the community forum, which is now on the homepage. If you go to IndieHackers.com, you just see dozens of conversations where hundreds of people were sort of helping each other out, asking questions, and helping each other start companies, meeting co-founders without me really doing anything.

David Rosenthal 1h 26m 19s

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

Courtland Allen 1h 26m 26s

Yeah, kind of. And I've been trying to consolidate things and not quite consolidated it yet. 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 kind of shared their stories and you can sort and filter those.

You can also go to sort of the product directory, which I mentioned earlier where it's just more self-serve, anybody can add a product there. You can share how much money you're making, share your milestones along the way. Everybody there sort of competes to have the best milestone every day. We have this leaderboard that kind of resets and over posts the best update for that day in terms of upvotes, it 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 12,000 products. We got 500 interviews. We have a podcast that, you know, went from, I think just maybe a thousand downloads total when Stripe acquired Indie Hackers to now millions of downloads. The community forum has gone from just a few dozen conversations a week to the point where there's like a thousand comments a day, over 250 posts every single day in the community forum. Just tens of thousands of people helping each other out. Based on the numbers Indie Hackers has grown tremendously since we've joined Stripe.

David Rosenthal 1h 27m 38s

So awesome.

Courtland Allen 1h 27m 38s

And one of the things that we like to measure is kind of a rough estimate of how many people have started companies as a result of Indie Hackers. We kind of send out a survey to people maybe six months or so after they joined. We ask them to just say like true or false or different questions. And one of them is, you know, "Would you have started your company, if not for Indie Hackers?" And most people like," Oh yeah, I would've started it anyway” or "I haven't started yet." But a good 15-20% 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. If you multiply that by 140,000, you know, different people who've joined the community forum, that's I think a very substantial number of companies. Yeah. That's a lot of tiny companies and some of them have gotten bigger, gotten acquired. A lot of them are on Stripe.

Sort of the way that Patrick explained to me earlier, when I first joined Stripe was like, "Hey, it's your job to, you know, get people to start companies. It's our job to have a product that's good enough to win them over." I'm not sitting here trying to like hawk Stripe and convert people to Stripe. That's something that Stripe does on its own.

Ben Gilbert 1h 28m 36s

I'm also curious, approximately what percent of Indie Hackers use Stripe for their company.

Courtland Allen 1h 28m 44s

We don't really have a process, we don't measure. It's a lot of just trust. Right, okay. We know that Stripe is pretty damn good as a product, it comes up on the community forum all the time. I think it was the most referenced company and all of the interviews that I did even before joining Stripe.

David Rosenthal 1h 28m 58s

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. That's what Glow is like. Well, I don't even know if there is another alternative.

Courtland Allen 1h 29m 12s

It's a really good product.

Ben Gilbert 1h 29m 14s

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

David Rosenthal 1h 29m 19s

So alternatives worth using, let's put it that way.

Ben Gilbert 1h 29m 22s

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

Courtland Allen 1h 29m 28s

We had exactly 1,403 users on the day that we got acquired by Stripe. So we're a hundred X bigger today.

Ben Gilbert 1h 29m 36s

Almost exactly a hundred X bigger.

Courtland Allen 1h 29m 38s

Yeah. Almost exactly a hundred X.

Ben Gilbert 1h 29m 39s

Wow.

Courtland Allen 1h 29m 39s

That's pretty cool. It's cool to see that...

David Rosenthal 1h 29m 41s

That's cool.

Courtland Allen 1h 29m 42s

Yeah. There's a lot of stuff to look into too. It's okay, well, how much bigger is the podcast? How many more conversations are people having? Because it's not just about having more people, but it's about engaging them more. How many return visits do people have? And we track a lot of random stuff, but the number of users is straightforwardly a hundred X bigger in three years.

Ben Gilbert 1h 29m 58s

If Stripe hadn't acquired Indie Hackers, it's not like all the companies that have been created wouldn't have used Stripe. I don't think you influenced any of their decisions on what, you know, who to use for payments. What they were really doing is saying, "Man, this thing is really good for our business that it exists. Let's make sure it can thrive as much as possible." But 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.

Courtland Allen 1h 30m 30s

Again, I don't measure, you know, would you have used Stripe? It's not even my goal really to make people use Stripe. It's my goal to make people start companies. But I want people who would never have started a company cause they didn't think it was possible, they hadn't seen anyone like them start a company, they didn't see a path.

When they hear a story on the Indie Hackers Podcast, when they go on the forum and they see somebody who's like, I met a YC founder at the Stripe event a couple years ago and I was just kinda talking to him and he's like, "Yeah, I love Indie Hackers." I'm like, you know, "What's your experience with it?" He's like, "Oh, I read the story you did with this guy who started this like review site. And I'm like, I'm way smarter than this guy, I could start a company. So I did, then I got into YC and I wouldn't go to Indie Hackers anymore." That's pretty common. I meet a lot of people like that who were just inspired and they literally started cause they just read that it was possible.

When I think about me, I started my career because people told me it was possible, you know? And I think spreading those stories helps people get started and that's literally all I care about. I don't care how many of these people end up using Stripe, that's the job of Stripe engineers and product managers like make Stripe the best product

Ben Gilbert 1h 31m 29s

It's a bet on the internet being able to enable people to create far more companies than they otherwise could have.

Courtland Allen 1h 31m 36s

Did you see the stats that came out last quarter about new business creation or it's like...

David Rosenthal 1h 31m 40s

Yes.

Courtland Allen 1h 31m 40s

Yeah. 600,000 people a quarter in the United States are creating businesses like 10 years ago. And then last year was 800,000 people a quarter. And this year it's 1.6 million people created a business or filed to start a business in Q3 2020, which is insane cause it's doubled.

David Rosenthal 1h 31m 57s

So cool.

Ben Gilbert 1h 31m 57s

What does that say for, aren't there more and more winner take all opportunities? Are we seeing, now we're well into the playbook, but are we seeing basically a barbell-ifcation where the big startups consolidate to only a few big winners in each market, but then there's massive, massive opportunity to go after a long tail.

Courtland Allen 1h 32m 16s

Yeah, I think number one, there's a lot of these winner take all startups, but almost all of them create niche business opportunities for other founders. And so it's not like this exclusive thing like, Oh, Facebook took the social networking market, now there's no business opportunities. It turns out a ton of media companies get started off the back of that.

A ton of app companies get started off the back of that. There's companies that teach you how to build a Facebook page to get started off the back of that. I think as an Indie Hacker, you don't have to worry too much about the winner take all companies. Then we have all these platforms, you know, YouTube, Substack, OnlyFans, arguably Twitter, where people are just building audiences and businesses off the back of all those things.

And so what's kind of cool is it's kind of never going to be, you know, all the niches are taken, there's no ideas left. I think what people underestimate is just the number of people adopting technology for the first time. Just because Zoom exists doesn't mean everybody uses it. We've seen very clearly this year, way more people are using Zoom, because they've been forced to adopt this thing they’ve been kind of ignoring in the past because they just 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.

And then most successful Indie Hacker businesses sell to other businesses. So it's kind of this self-fulfilling sort of chain reaction where the more businesses there are, the more products they need. It's kind of cool to see it accelerating. And I wouldn't be surprised if that number, you know, in a few years it was 5 million Americans a month are creating an online business.

David Rosenthal 1h 33m 36s

Yeah, that's what I was thinking on that is, you know, you've got the platforms say, let's look at Stripe or Shopify, and then you've got people that start Shopify stores or start businesses on the internet and use Stripe. But then there's this whole other category that I think is perfect for Indie Hackers of, oh, well there's actually stuff that you can build to help the people that are using Shopify, that are using Stripe.

Courtland Allen 1h 34m 0s

Totally.

David Rosenthal 1h 34m 2s

There's so many businesses that have been started around Shopify and Stripe too, that are not a business on Shopify. They're a business that provides a custom set of tools for a certain set of users that need hobby businesses, like you're a hobby game store and you are both buying and selling from your customers. Your customers come in, they trade in and stuff. You can run on Shopify. Great. But you also need some custom functionality to buy stuff from your customers.

Courtland Allen 1h 34m 29s

Right.

David Rosenthal 1h 34m 29s

Boom, businesses.

Courtland Allen 1h 34m 30s

Exactly. And I think a lot of smarter founders are figuring out ways to kind of escape the competition because okay you can build a Shopify plugin, but there's a lot of other Shopify plugins. So it's a cool opportunity. But then you get kind of crowded out. I'm talking to a guy tomorrow, his name's Jordan O'Connor. And he's got a really cool story where he's a father, a husband, he had a full-time job and he would eke out time every morning to kind of work on his business because he knew that after 8:00 AM, his son was going to be awake and he's gonna have no time at all to do anything.

And so what he ended up doing was kind of escaping the competition and he built a bot for this app called Poshmark, which is huge. A lot of people buy and sell their used clothing on Poshmark, but they don't have a marketplace. They have no, they don't even have an official API. So he just sort of reverse engineered things.

He's like, there's not going to be any competition here, but it's kind of the same playbook, build an ancillary tool for this bigger platform. And he bought a bot that helps you do well on Poshmark. I think you got to 20 grand a month and now he's just kind of quit his job. He's just kinda set. And he's just doing other fun projects now that, you know, interest him from year to year while that bot just kind of makes money for him in the background.

Ben Gilbert 1h 35m 36s

Magic of software.

Courtland Allen 1h 35m 37s

Pretty crazy.

Ben Rosenthal 1h 35m 38s

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

Courtland Allen 1h 35m 51s

Oh, A+. I think it's, I'm slightly biased here. Stripe is a company, as you may know that has lots and lots of money and the Indie Hackers acquisition did not cost billions of dollars. I think it's generated only goodwill toward Stripe, more customers, more users for 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 part of Stripe. I think for the people who use Indie Hackers, they're very concerned early on, you know, they're very worried. And I don't think I've met a single person who said that they aren't happy that it happened. It's hard to imagine it having gone better.

Ben Gilbert 1h 36m 24s

Yeah. Should more people do this? Basically bet on, I mean, the way that I'm sort of categorizing this in my head is they made an investment to ensure the continuity of this thing that was creating new customers for them. Do other companies do that? Should've more companies do that?

Courtland Allen 1h 36m 42s

I think they should be a lot more creative and imaginative. I think there's, as humans we have this impulse to just mess with things. It's really hard to buy something and then not touch it. It's really hard to do that. And I think when people think about like, "Okay, if I buy this, what am I going to do with it? Oh, it's going to be like so much work. I have to do this. I do that." And they don't make these acquisitions. Whereas I think at Stripe they're very much like, "No, Courtland's doing a good job and we don't have to do anything."

And if we can just ensure that it keeps going, like you said, that's a huge win by itself. But there's other ones too, you know, I think one of the trends we're going to see going forward is tech companies basically owning like some kind of media company, which I think is super powerful because media companies are what connects with actual people on the ground.

And in a way, Indie Hackers is still very much a media company. I still spend a lot of time on the podcast. I spend a lot of time on our newsletter, put out a ton of content. We're sort of becoming a platform almost like Substack ask or enabling other people to sort of build newsletters and grow their audiences on Indie Hackers.

I think even without just having Indie Hackers continue to exist and even without it like driving additional customers for Stripe, it's just a good way for Stripe to be able to communicate in the future if it wants to, you know, we're launching this thing or, you know, we think this about the world and now they have a place that's not just Hacker News or Twitter to do that, right?

Ben Gilbert 1h 37m 55s

Yeah.

David Rosenthal 1h 37m 55s

Has Stripe had anything else like this since you've been bought or…

Courtland Allen 1h 38m 0s

Yeah, Stripe has a magazine called Increment Magazine, just increment.com. It's kind of the best sort of magazine for all sorts of basically work that gets done. So they've done issues on software engineering and APIs and cloud and being on call and people love this magazine. It's really well-produced. It was created by Susan Fowler, who's the engineer who kind of blew the whistle on Uber back in the day. And now she works, I think at the New York Times. That's a really cool Stripe project that I don't think gets enough press and attention.

There’s also Stripe Press, which is kind of an in-house thing. It wasn't exactly acquired, but all these sort of initiatives, I think, you know, involve often people who are like come in from outside the company and help. And they're all kind of moonshots, you know, I put it in a very similar category to Indie Hackers, even though it's, you know, 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 how many people actually read this book and made a decision because of it, but we can kind of trust that they will do that because we know that's how inspiration works. It'll increase Stripes bottom line.

Ben Gilbert 1h 39m 9s

Yep. Makes total sense. All right. Well for Acquired listeners, cause I know we're releasing this in both feeds. Where can people find you? What should they check out first of the various Indie Hackers and Courtland properties?

Courtland Allen 1h 39m 25s

Yeah, I mean the easiest way to really get into Indie Hackers is the podcast. So if you just go to your podcast player and search for Indie Hackers, it will come right up top for you. Check out any of the episodes. They're all pretty good. They're all different stories of founders and how they succeeded.

I just recommend listening to a few of them and really absorbing, you know, what is this path like? How can you start off maybe as an Indie Hacker and then eventually start a much bigger company. I've interviewed lots of founders of YC-funded companies and VC-funded companies, but also tiny Indie Hackers that don't want to grow anymore. So check out the podcast. And you can find me on Twitter, @csallen.

Ben Gilbert 1h 39m 59s

Awesome.

David Rosenthal 1h 39m 59s

Love it.

Courtland Allen 1h 40m 0s

Listeners, if you enjoyed this episode and you want an easy way to support the podcast, you should leave a review for us on iTunes or Apple podcasts. Probably the fastest way to get there if you're on a Mac is to visit IndieHackers.com/reviews. I really appreciate your support and I read pretty much all the reviews you leave over there.

Thank you so much for listening and as always, I will see you next time.