Special: Acquired x Indie Hackers

Transcript from https://podmenti.com/t/a6b0d5962b1684fc

I've got new M one MacBook here. This is the first episode we're doing on it.
Nice. Nice silent recording in the background. No uh what do they call it on the pro the uh active cooling system. Don't call it a fan.

Welcome to this special episode of Acquired, the podcast about great technology companies and the stories and playbooks behind them.
I'm Ben Gilbert, and I'm the co-founder of Pioneer Square Labs, a startup studio and venture capital firm in Seattle. And I'm David Rosenthal, and I am an angel investor and advisor to startups based in San Francisco.
And we are your hosts.
As regular listeners know, we typically cover some of the biggest companies, those that IPO, see Airbnb and DoorDash last week.
And the companies that
Get some of the splashiest press coverage.
But today's episode
Is quite a bit different.
In our conversation with Cortland Allen of Indie Hackers, which is the largest community of startup founders, we dive into the stories of the underdogs.
What happens when there are millions of people doing small business entrepreneurship?
How does the globally addressable market of three billion internet users open the door for the nichiest of products? And importantly,
What was Cortland's lived experience of starting his own string of companies that ultimately led to starting indie hackers?
and its acquisition by what is now the hottest private company in the world
Stripe.
Yeah, man. Last one left standing after last week.
No kidding. And uh a lot of people cannot wait for it to IPO soon enough.
Yeah.
I
Gotta imagine our biggest episode of next season. Hopefully next season. When is this thing gonna happen?
Season eight, season nine, we'll see, David.
We'll see.
Well, as always, if you love acquired and you want more
Well, good news. We have the answer for you.
The community of acquired limited partners is now an army in the thousands.
For those of you who aren't already a part of the gang, becoming an LP gets you twice as many episodes, access to live events with us and other LPs is
Even in an all virtual twenty twenty, it's
And most near and dear to David and My Hearts, you have the biggest influence on what we cover in the show.
So if you want to join, you can click the link in the show notes or go to acquire.fm slash LP.
All right listeners.
Now is a great time to talk about a new partner of ours here on Acquired, Lagora.
The agentic operating system that is redefining how the world's best legal teams work.
Yep. It's sort of obvious that AI is gonna completely change the legal industry. I bet most of you listening have dropped a contract into some sort of AI chat bot out there. Lagora took that insight and asked the question, what if you really built something with that power from the ground up for the legal industry?
So the founders did exactly what great founders do.
operate with obsessive customer focus.
They embedded inside a massive law firm for months.
They sat with the lawyers just watching how the work really gets done.
And that's how you get features that customers love, like tabular review, where you drop in a folder of hundreds of contracts and it pulls every key term into a grid a lawyer can actually work with. Legor's Bet Here is interesting, since it lets each lawyer handle more complexity, any given person can increase the quality of their work.
and do higher value work. And this means that the pie can grow even as each individual task takes less time.
And they recently launched Lagora Agent, offering greater intelligence and performance. The agent lets lawyers set an objective. Then it can handle the planning and the execution and delivery of the final product. Legal teams get to maintain full control and transparency since they're still involved where judgment is required.
And Legora works where you already work. You can use it within Microsoft Word while redlining or drafting.
The early Lagora numbers essentially
speak for themselves. When they have a head to head pilot with their top competitor, they win seventy percent of the time. Lagora now has over a hundred thousand lawyers on the platform from twelve hundred legal teams in fifty countries.
And crazily, they went from one million
to a hundred million in ARR.

Eighteen months.

truly insane numbers. And that is the real test.
Plenty of things demo well, but the question is whether a busy associate actually reaches for it during crunch time, or whether a partner trusts it before going into a conversation with a major client.
If your legal team wants to check it out, whether you're a law firm or you're in house at a company.
You can learn more at Lagora.com slash acquired
And just tell'em that Ben and David sent you.
Okay, now on to our crossover episode with indie hackers.
Cortland Allen, welcome to Acquired.
Ben.
David, thanks for having me.
So great to have you here.
Our pleasure.
For anyone who has not listened to uh your voice for the many hours that I have on the Indie Hackers podcast, obviously we're gonna reference it lots and lots throughout the show, but go check it out and very excited to be doing a crossover episode with you. Yeah, I'm excited to do this. People have been asking for a while.
For me to do an episode on myself.
'Cause obviously Andy Hackers is kind of an interview show. I just tell other people's stories.
And I've always been like, as weird as it sounds, like shy to do an episode of my own podcast, so
Congratulations on being the first people to convince me.
Well look, we are the acquired podcast and you did that mega deal exit to Stripe. So how could we not you know cover the acquisition of the century? This is great. It's got like all the hallmarks of uh both of our episodes. We'll see how that goes.
Well, David, who is Cortland for listeners who don't listen to any hackers or haven't participated in the community?
Yeah. So Cortland is a former
Why C found her.
MIT alum
And founder of a company
That has been acquired by Stripe.
All of which
Seems like it would fit very much into the acquired theme.
But there's a twist.
Unlike the big gopher broke we were jabbing before we hit record here about
the typical startup path that we cover all the time on this show is trying to build the new version of you know standard oil out there except you know ten, a hundred, a thousand times bigger is than the Rockefellers and the Carnegie could ever imagine. Cortland is all about a different philosophy out there.
the indie philosophy and of course the company that he started and what he runs within stripe and
The website and the community and the podcast is
Indie hackers. And indie hackers I think is really cool. We're gonna get into it in this episode. It's kinda like if big tech and startups are the Rockefellers, this is the small business entrepreneurship of the twenty first century. And I think it's really, really cool. So we're pumped.
I don't know. You're gonna tell it. I like to think of it as the underdogs.
You know, like the internet's been around for for decades.
And I think
The world is still kinda slowly waking up to how much
it's kinda changed the game for just like regular people. Everybody's connected to everybody.
You can reach literally millions of people if you're clever enough for pretty much zero dollars.
And so people are creating these very tiny niche businesses.
that could never have existed twenty or thirty years ago and in some cases not even five or ten years ago.
And I think it's it's
It's becoming possible to like sit down in your living room.
uh wearing your underwear or whatever you're wearing and just create something that's super valuable to your community and your customers uh and that's really kind of fun and fulfilling and challenging for you to work on as a person
And that makes you rich in the process.
And I think that's pretty crazy to check all three of those boxes. So uh thousands of people are doing this today.
And the question that like I'm asking myself constantly is like what happens when millions of people are doing this five or ten years from now?
Yeah. I think that's what's so cool is like
Small business entrepreneurship in the past was a great way to build wealth and do well.
You know, for your family and for yourself.
But
With the same art honestly, like less amount of effort now on the internet, this path exists.
That the wealth you can build even by taking this path
It's still so much bigger than you could build
you know, building a dry cleaning business in the past or running a restaurant or
A lot bigger. Not to foreshadow our sort of playbook too much, but it does
remind me that, you know, in a pre Internet era, the local small business owner
uh was geographically constrained. And they could that you could have a general store that sold everything, but it could only sell everything to the people in your town. And obviously the the sort of like large scale version of that is Walmart, but that
It's a very different type of business to run. With the internet, you can just do one thing in one niche, but you have a nationally, if not globally, addressable market. And so I I continue like Cortland from listening to your show
Every time I listen to an episode I I get smacked in the face with, wait, that niche is that big and people find these crazy opportunities. I just listened to the Patio Eleven episode and he was talking about Bingo Card Creator. And I'm like, A bing creator could be a business, but like
These niches are so deep or so wide or however you want to describe them. If your TAM is the three billion people uh with the internet, then every niche within that TAM can be on its own big. Hey man, Starlink's coming soon. It's gonna be seven billion. Exactly. If you have like a a business that only appeals to like, you know, one in a thousand or one in a million people
Uh, you need to live in like a very big city.
to create a brick and mortar business that's gonna survive. But on the internet, like that turns out to be millions of people who can use like your underwater bingo card creation, whatever it is that you're you're making, which means that like pretty much everybody can figure out something really specific that no one else is doing.
And kinda stake their claim on the internet, which I think is super cool.
I hear the real estate is cheap too, so all right, well so let's get into your story. Okay, let's start
Way back.
Before MIT.
Your
Family and your mom specifically was an entrepreneur when you were growing up, right? So I had a
I was just talking to um Jason Kalakanas about this on his podcast where he was talking about
Kinda opportunity, you know, can anybody start a company? Does everybody have an equal chance to do this?
I think in a way like
You know, nobody nobody's quite equal. Everybody's got kind of a different starting line.
And when I look at my childhood, like I had a very good
starting line. I had uh two loving parents. They're very attentive. They're very devoted
We were sort of middle class, but very comfortable.
And like you mentioned, my mom was an entrepreneur. She was always doing her own kind of crazy hygiene startups, selling computers and stuff in the nineties.
And my dad was part of like
like this elite team of like furniture makers. There's like nine of them. And like each had a different role. And they would make like crazy furniture for like celebrities.
So he wasn't making like a ton of money, but he was doing something that he found really fun. He was like the furniture finisher. So he'd take like a you know, ugly piece of wood and make it look like amazing.
And I grew up like these two people in my lives who kinda showed me that you can do
Pretty much whatever you want and like kinda scratch out a living.
Yeah, you can do this and
Like it'll be fine.
You can have like a good life, right? Yeah, exactly. You can have a good life, you know, like we were eating, we weren't missing meals.
I had a bunch of other advantages too, you know, like I was an American. I was born in the late twentieth century
Because of my mom's computer business, as she ran for like a year or two before it crashed, like we had a computer and the internet when I was in the third grade, like right after the web came out.
And so of course like I was addicted to video games and like whatever I could play.
But from the adult's perspective around me, they're like oh this is a computer whiz. You know, whenever I've got a computer issue, Cortland spends so much time on his computer.
You can just like swoop in and fix it.
So I was like doing all this IT work on the side and of course nobody ever paid me. I made zero dollars, like I said, nine year old fixing people's computers. But
I got a lot of positive encouragement because
From my perspective, I was just like, you know, playing games and fixing bugs and stuff. But from like the average adult's perspective in the mid nineties, they were looking at like the tech boom and they were looking at Microsoft stock price and the fact that Bill Gates was like, you know, mega rich. And so they would sort of pay me in encouragement. They'd be like, Oh yeah, you're gonna be like the next Bill Gates, like keep it up.
And what was cool about that was
You know, I got to be like a little computer nerd.
And also see that like this
really like old computer nerd was universally respected by like every single person that I ever met. And everybody told me that it would be a cool thing to aspire to kind of be that.
So by the time I was like ten or eleven, I was like, Okay, I wanna be Bill Gates, you know, I wanna start my own company, I wanna go to good college. Like how do I how do I get on that path?
In some ways it's like echoes of uh the Tim Sweeney story and uh and Epic Games, you know, him starting out.
It was his older brother, right? Right, Ben, that uh
had a computer hardware business.
And so he like went out to visit his brother.
Got hooked up with computers, got obsessed, then started like an IT consulting business after the lawnmowing business. He was fixing TVs.
And not at all to put myself in the same category. I was fixing teachers' computers in in middle school as my uh I think I was making like seven bucks an hour quite. So sorry I was uh dwarfing you there. But yeah, that's so many people's entree before they actually get into programming is basically just fixing stuff. Yeah. And I think it's important. Like I've taught people how to code.
In subsequent years.
And there's this kind of base layer that gets ignored of just like computer literacy.
Where the people who learn the fastest are people who just like they're just very comfortable if their computer crashes or has an error, like they know all the keyboard shortcuts, they're good at Googling stuff.
And if you have that kind of base layer of skills, it makes everything else
Much easier.
So you're eleven or twelve at that point
you know that you want to go into a, you know, technical or programming or computer science. Did that ever deviate or was that pretty much like nope laser focus from that point forward?
Oh man, I had this like real embarrassing phase where like I was trying to choose between like do I want to be Bill Gates?
Or do I want to be Kenny G? So I had a saxophone. I was playing like a lot of like just corny contemporary jazz music. Uh and luckily luckily the computer stuff won out at some point.
And after that, like I didn't deviate. Like that was a hundred percent what I wanted to do.
I had a ton of like just a ton of fun just like
doing stuff in the nineties on my computer.
Like a lot of support around me. And
You know, in one way I think I had kind of like the world heavyweight champion of of childhoods, you know, was like really, really good, like really advantageous, but also had some hardship.
Like my dad died when I was pretty young. I was in high school.
And like for me that was just like a huge wake up call, like oh shit.
Sometimes things get real and like no one's gonna kinda swoop in to save you.
You have to kinda learn how to survive.
And make it through tough things on your own.
And so I got like almost like kind of the perfect mix of like hardship.
And like encouragement and like
privilege and a way. And so yeah, by the time I like I I left
uh to go to college. I felt like pretty
ready to take whatever the world's gonna throw at me and also like pretty
far ahead of the curve in terms of like knowing what I wanted to do. Like there's never a question like what major do I want to ha have, you know, what do I wanna do after I graduate? Like I was always a hundred percent certain what I wanted. And I'm I'm sure that tragic
you know, death in the family also forces a lot of early maturity that you have to take on sort of more responsibility or at least think about the broader context around your life than just
yourself earlier than you otherwise would have. Totally.
And like I think for me the biggest impact was just like
You kinda get like a floor. You establish like, Okay, this is the worst thing that's ever happened to me. And like I survived it. You know, like it was terrible, like all sorts of like bad side effects you wouldn't even think about, but
Like once you establish a floor
Then like a lot of other things just don't look that scary. Like they don't look like they're that big of a deal. Like, Okay, what if I start a company and it fails? Like, Oh no, you know, like I'll go get a j I'll go get a job. Like nobody, you know.
So I I think that's kinda what I got out of it.
I assume that the computer the the love of computers and knowing what you wanted to do.
Getting out of the Kenny G phase.
That's what probably MIT. The the Kenny G phase was uh a good one to escape. Yeah, so I I remember like um really wanting to go to MIT. I somehow figured out that that was like kinda the best school you could go to if you wanted to be a computer scientist. I had no idea that Stanford even existed. Like if I had known that and that it was in the heart of Silicon Valley, I probably would have tried to go there.
And I also didn't know that like it was even feasible to just not go to college. Like if I had known that I could do that, like I probably would have just done that and tried to start some stuff.
But I remember talking to my mom and asking okay, like
you know, how do you get into M I T? And she's like, Well good good grades and study and uh apply and like 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.
And I remember thinking like how frightening that was. Like I got like one shot to do the thing that I wanted to do. And if I got rejected, then I would just be done.
And in a lot of ways, like that was a much scarier thing than I think starting companies that like have the risk of failure,'cause like you can start a company a million times. Like if it fails, like there's no like all right, you know, that's it. You gotta go somewhere else now. Like you can just keep doing it over and over again. Well, how many companies have you started now?
Seven.
And he hackers is my my seventh attempt to do something that worked. And the only one that really that really worked.
So we yeah, I was gonna say so when you get
To M I T U
Uh I think if I I understand the history, you
Start applying to Y C like
regularly. Yeah, yeah, I played a lot of times. So is this like a like a every quarter thing? It's like register for classes, put in the Y C app, like Well I was like a a pretty bad student. I didn't understand like the idea of like
I just didn't really want to learn and I thought all the stuff I was learning in my CS classes was boring. And so I spent a lot of time working on my own side projects.
And at some point I discover that like there's this magical entity out there that will like give you a bunch of money.
to take your project and try to make like a company out of it. So I got really hooked and I would
Uh spent a lot of time applying. I got rejected at least like two or three times.
Had Dropbox already grough Y C at this point and kind of at some point during like when I was in college, Dropbox like went through. And Dropbox was also an MIT startup. So everybody on campus had like a bunch of free Dropbox codes and we had like a ton of free space and everybody knew their story. So there's a lot of like positive encouragement there as well. Like, Oh, you want to apply to YC? Like everybody knows what that is and thin to just
apply even if you get rejected. Like I got rejected once and I got an email from Paul Graham where he was like, Oh, I think you know you could have done like this better.
I remember just like showing that email to my friends, like so proud, like the PG responded to me. This is a rejection. Basically. Oh, that's what were some of the ideas you're replying with?
So the very first one was this company called F Mail.
Which stood for like get this.
Gmail for Facebook.
Facebook released like their platform sometime when I was I think a junior
And at that point, like I'd never really built.
Like a web app.
But a buddy of mine was just like super encouraging. He was like, Oh, this is so easy, Corland. Just go learn PHP. And I'm like, PHP, like what is that? So I went online and I started learning it and it's like I'm like, Well, how do I extore user information? Facebook was all PHP. Yeah, yeah, it was all PHP. And like I just kept asking like, Oh, how do I do this? He's like, Oh, just go learn like my SQL.
And like after a semester, I learned all this different stuff and I'd like been able to build this app from scratch.
And I thought it was amazing, like oh I didn't know anything about this stuff and now I can like make my own web app.
Uh and I applied for Y C
And like of course got rejected.
But a really cool thing happened where
Because there weren't that many Facebook apps.

people were just like looking for stuff to write about. A bunch of like these small tech
publications just like wrote about it. Like, oh crazy MIT genius figures out a way to put a Gmail inside of Facebook. Like we'd scanned it to like look like Facebook. And like it barely even worked. It was like super crappy, but I was like, wow, it's like really easy to get like the press to write about you. And like you can do a really simple thing that takes you a semester, even if you're a total beginner.
And if I it's kind of creative and kinda unique and people haven't seen it before, like you'll get attention. So that was a like a kind of a good experience, even though uh I got rejected.
And that was an era too where there were so few web products where when you did one and you made a new website, it could kind of stand out'cause there just wasn't a lot of noise. I remember you you fled back so many memories there.
When I was in college, it's funny, yours was F Mail, mine was called Hackerfollow and it was uh Twitter for Hacker News. Like I wanted to be able to follow people on Hacker News and have a timeline view of when they updated. So my buddy and I built Hackerfollow.
And similarly, like I learned PHP and MySQL to be able to like store the stuff in a database and I mean that that's what everybody did then. That's even what Facebook was written in, David, as as you mentioned. And uh
The web was like a it felt like a small place.
Yeah, it really did. And I think
To some degree, like it always
kind of feels like that in hindsight. You know, I think like ten years from now, people will look back and be like, Oh, like the quaint times of twenty twenty when you could do when you could do anything and it would get attention, you know? And like to some degree like that's true. Like if you spend
Like very few people have the time to sit down and just like think creatively about ideas.
And like one of the easiest ways you wanna come up with any creative idea is just to take like
two or three things and combine them because like once you do these combinations, like you instantly start getting to ranges where like no one has ever done that before.
Like if you type like the dog into Google, you're gonna get like ten billion results. But if you talk like the dog left, you're gonna get like a million results. And if you're like
type like the dog left the store with a bone, there's gonna be like no results. It'll be like a sentence that no one has ever said before in the history of like the world. And then the same thing is true with ideas. So I think there's always kind of like this this
sort of framework you can use to come up with interesting ideas. And like we both found kind of the same one, you know, like Oh, let's take this one thing and put it inside this other. And like that was enough to stand out. And I think that's still true today.
Yeah. Okay, so you mentioned hacker news.
Which I assume is gonna continue to play a big role in the story here. What um were you hanging out on hacker news while you're at MIT and doing all these Vicey applications? So back in the day, like Paul Graham used to write on his blog all the time about startups and like all sorts of like different stories. And it was like he was very motivational, inspirational, and positive.
And then he had this website he created.
Which like again, he just like seemed like it was very haphazard. He's like, What if I had like a little Reddit clone? And of course it's like now like millions and millions of visitors or whatever. But if you wanted to apply to Y C like you had to be on hacker news. Yeah. Ben you know the story, right? It exists because he was dissatisfied with our programming.
And was asking Alexis to make that better. Like Alexis and Steve I think is either to make it better or maybe to invent it at all because they're that subreddit didn't exist yet and got frustrated with their slowness and started hacker news.
Yeah. That's hilarious. So he's like, Yeah, this is not good enough. Even though he's an investor and read it and just like made his own competitor. I'm pretty sure that's against some sort of code of of ethics. But you kinda had to have a hacker news account to apply to B NYC. And like not only did you want to have a hacker news account, but you wanted to have like a history of like smart like
intelligent, thoughtful comments because you know Paul Graham and the partners are gonna look at what like what you had posted.
So if I look at like my Y C account.
Right now. I think it's
Yeah, created October eighth.
Two thousand and eight. So I was on Y C like way back in the day, reading everything, digesting everything, and then trying to leave smart comments that like I would be probably embarrassed to go back and look at right now.
It's so funny to think about now, like
Got how many companies there were like three hundred companies that go through Y Cish about every year. And like But it was this little corner and community
of the internet. I mean it still is a community, a very large community now in a certain sense, but uh yeah, I remember being a YC fan first and foremost and using the products. Like I was proud to be a Dropbox user and abandoned my flash drive because it was a Y C company.
I suppose that that is even actually a bigger effect today, but it it felt at some point like a club. I remember I think it was like senior year in my high school, that I felt like I was in some sort of club for even knowing what it was.
Yeah, I kinda had that feeling. And then like I eventually ended up doing Y C and I remember like distinctly that there are like maybe thirty five
companies my batch or something.
And all of us felt like oh man, like Y C is like it's jumped a shark. It used to be so intimate and like so small back in the day. Now like it's just this huge and personal thing, and you only get to see like Paul Graham like once or twice a week. Like what even is this? And of course now it's like ten times bigger than it was back then. Yeah.
So catch us up there. So what what idea did you end up going through Y C with?
Yeah, so
In college I ended up
uh meeting up with like these two grad students who had this like cool idea for this new version of email.
And then we tried working on it.
And like it was pretty cool actually. Like we got a lot of press, we got a lot of attention, but we didn't charge any money for it. And so after like
a year of working on that, like we ran out of money. We had won some business plan competition and like it was like twenty five K. So I kinda just like lived frugally on that for a year in downtown Boston.
Ran out of money.
And I decided like I was gonna move to SF.
and somehow like get into Y C.
So I I worked, I got like a like maybe enough money for like four months of rent.
Moved out to SF.
And I just started reading like Paul Graham's like RFS's request for startups.
That he would publish.
And one of the ideas on there was like kinda related to what I'd already been doing. Yeah, this whole thesis that like
you know, the email inbox is this like unexploited, you know, domain and you can have a Trojan horse where you get in there with like some some sort of productivity app or something. And then once you get all of the email users off Gmail, like you convert them to your own thing.
And so like that was his obsession, like these like clever tricks you could use to like get a ton of people on your apps. And so I was like, Okay, let's just let's just do that.
So I met another guy again on Hacker News.
Who like kind of posted like, hey, I'm looking for a co founder. Okay, yeah, I was gonna say I read that. Like you met your co-founder on that. He was like one of my previous competitors from my earlier email thing. And his his app like also wasn't doing that well. So we're like, why don't we join forces? You met in a coffee shop in San Francisco. And I had like maybe like
a month of like money in my bank account. I don't know what I would have done. I would I would have just like had to somehow find money or like get a job immediately. But we applied together and like the process was super quick. We we got in, PG asked us a few questions. We had like the Y C partner interview
And they're like, Yeah, cool. And I was just like, Okay, well, like when do we get the money? So I can pay my rent this month. Was this uh what year was this what, twenty? Uh like we did winter twenty eleven for Y C, so this was like in the fall of twenty ten.
Like November, December we were possibly
Before the Gary Milner SP Angel deal where you got that happened during our batch. That was like the like we were the very first guest for that. I remember the the previous Y C batch was super jealous because they only got like, you know, like a seventeen K or whatever. And so that's what we got at first. It was like seventeen K divided by two, me and my co founder like you know, we had like enough for the two of us.
We ended up moving into this rent control department and SF and just eating like a lot of like oatmeal and crackers and stuff. And then I remember uh like one day during Y C they kinda called us down like on a like a Friday or like some off day.
Like hey, it's very important, everybody come down.
And we went down to the Y C headquarters.
And they had like those telepresence robots kinda like walking around, like sort of like a a camera, like and a screen on wheels. And there's like Yuri Millanaire's face on it, like this Russian oligarch billionaire like walking around talking to everybody and like we've got an announcement. And I was like, Yeah, we're gonna give everybody like a hundred and forty thousand dollars uh of additional money sort of no strings attached.
as an investment. So uh that was like one of the best days of my life. I was like, Okay, well I'm gonna start eating like I'm gonna upgrade to uh ramen now. And uh not to worry about where my rent's gonna come from.
So we structurally understand that. Was that a convertible note that they invested on with that? Um
I couldn't tell you. I can't really remember.
I think it probably was a convertible note and this is before they had like
I mean, this is before they had the safe.
I think the save came came around like two or three years later. But it wasn't like literally free money. No, it wasn't literally free money. Like there were strings attached, but I I think it was uncapped though. It was a really good deal and none of us questioned it. Like we just signed it. We just signed the papers. So at this point you're getting like
Probably feels like a huge amount of money.
In funding. Right. Like you you don't have any customers, right? Nobody's going to be able to do it. We had literally nothing. We had like a bunch of janky code that I was writing and my co founder was going around like, you know, like doing some marketing stuff and trying to generate like press and like hype for like
A thing we hadn't built yet. So the idea we were working on was this it was called task force. The idea was
Uh you get all these tasks in your inbox, you know, like I've got Ben and David from Acquired like saying, Hey Corland, have you prepped for the podcast yet, right?
And uh no, you didn't really send me that email, but like if you had, I could have used Task Force to convert it into like a little to do and it would add it to a to do list in your inbox. And so then when I worked on that to do, if I added a due date or I checked it off, you would get an email that said, like, hey, Cortland is this far along on the to do, or Cortland just completed it.
So it was supposed to be like this viral thing that would like take over the inbox and everybody would have it.
Uh and eventually we did launch NYC.
And like we got a decent number of users. By the end of Y C I think we had like a hundred thousand users.
But back in the day, like that was nothing. Yeah, the social network had just come out a few months earlier. You know, a million dollars isn't cool, a billion dollars is cool. You know, that was kind of the mantra and like no one cared that your app had a hundred thousand
Users. Like that was meaningless.
I'm also dying over here because after Hackerfollow, my first app was a task list that I launched for iOS three.
Which is like right around the same time period. And uh if I remember right, like
Gmail tasks was still this like really
terrible UI that like could have had uh I mean you built the missing sort of connectivity for Gmail tasks that would eventually become
I think they turned it into its own thing, but it was like constrained within Gmail forever. Yeah, I think it's still there. Like if you know the right combination of keyboard shortcuts, like you could little task for you to pop up in Gmail, but it's not the most inspired idea, like a to do list, right? Every entrepreneur, every programmer has like a bunch of stuff they want to do when you think about solving your own problem, you're like if only I could, you know, organize my tasks into like a little list of checkboxes.
Uh and so we did that and like it kinda sorta worked, you know, but it wasn't like the home run.
That you really there it was, like the combination. And like that's exactly what the press wrote about. Like, Okay, you've seen a task list. You may have seen a task list in email, but if you've Gmail, uh people were like, No, I haven't, maybe I should sign up.
So we kinda combine those things and
And we got to demo day in Y C, like the very end of Y C
And we like presented and investors just like they weren't interested. They're like, Yeah, you know, you've had like okay growth, but like where is this really going? And we've invested in email startups in the past and they're all dead. Like what's what's gonna make yours different?
And we didn't have a good answer to that. So we went to the summer after Y C with like probably still like a hundred and twenty, hundred and thirty K of this money in the bank, trying to figure out like, you know, what are we gonna do?
with this startup it's like not growing fast enough for us to raise money.
Again if we have our lower right.
One of the talks.
Maybe like was it like a Tuesday dinner talk while you're on YC was Kevin Hale from Move. So Kevin Hale was this uh I thought he was like the coolest guy on planet Earth. We had these, you know, YC dinners every week and people would come in and we had like the Heroku founders came in and they just sold for like
three hundred million dollars and they just bought us like bought us all like the the nicest stakes and you know they were dressed in suave and like it was so so cool and flashy. Drive up in the Lambo. Yeah and like I think PG brought in like
the CEO of uh Yahoo at the time, who was like the super extroverted guy who like said a lot and it sounded really good, but you can never quite like tell what he said afterwards. You know, and PG was like, This is an example of a stereotypical CEO. Uh and uh then uh Kevin Hell came in from Woo Foo and he was just like cool, calm and collected character and he was just like yeah.
Like we're not raising any money, you know, like we uh packed our bags, we moved to Florida, like we're making forms, but we're making forms sexy.
And uh we do profit sharing with our team, you know, we go to the beach all the time, people work remote, like I don't even know when they're working really. And we get like ten calls a week from VCs who want to invest and we're like, nah, we're making millions of dollars. We're cool.
And no one else had said that. Like no one was making money. Like I didn't even know you how you could make money.
Like Stripe wasn't even a beta at the time.
It was so like in your cohort nobody was like talking about
There's like a few companies that like had some sort of revenue model, but like all the companies that were celebrated were the ones that had just like raised the most money. You know, who raised from A sixteen Z uh the earliest. You know, like there's one one founder on our batch we will not name.
who raised from A sixteen C like the very first week of Y C and they raised millions.
And they are like putting up kinda like Facebook growth numbers and everybody like worshiped the ground like that these founders walked on. Like the whole it was obnoxious to the point where it was like I didn't want to see them. But like you're kinda jealous too, because you're like, you know, I I kinda want that level of success, you know?
But at the end of the day, like nobody was making money. Nobody wanted to make money. No one like it was all about growth.
And so when I heard Kevin Hale talk
Like how Woofly was just
Was just kinda crushing it.
I remember running up to PG and like, Hey, like you know
We're not growing that much. Like what if we just did this? Like what if we charge money?
And he was like,
That's cool. Like whatever it takes to stay alive. You know, he was very much like be the cockroach, you know, don't die. Uh if you need to make money to survive until you pivot to a better idea.
Uh that's what you should do.
But like that sort of asterisk was always there. Like what you then do is pivot to a better idea that, you know, can make you a billion dollar unicorn because like who wants to just make a few million dollars a year?
It's so funny. David always reminds me that incentives drive behavior and
if you think about sort of Y C's incentive here, do you think back on it and say, Well, gosh, they they sort of for their portfolio construction, they needed us to be a billion dollar company, or at that point would Y C have been happy with a bunch of Cortlands building profitable businesses?
When you interview, they really want to know that you have a shot.
at becoming a billion dollar business because that's how the mechanics that's like the physics of the situation work. Like they need people to go for the gold. What ends up happening is just a lot of Y C companies died. Like even before our batch was over, it was kind of clear that like a few people had given up and they weren't really gonna make it. And like especially in the summer after a batch was over, like just a lot of companies fell off the radar.
I remember like talking to PG over the summer
We signed up for office hours and went in and he was just like happy we were like alive and still working. He was like, Oh yeah, we don't even know what happens to a lot of these companies after a certain amount of time. So like we're happy that you're here. And I think after that it's less they're less like
Adamant that okay, you gotta go for a billion, you gotta go for a billion, you gotta be a unicorn. They're like, Do whatever it takes to survive and get to the next stage.
I think in in a lot of respects like that's kind of like the hallmark of being a good entrepreneur. Like how can you take like one
you know, small success and partly that.
into something bigger. And eventually maybe you get another shot at going for the Unicorn Company. So
I think in the beginning they were very focused on us being big.
There's all sorts of questions about how this gets big, which were easy to answer because it was like P G's idea that we were working on.
But later on I was like, Okay, how do you not how do you not die?
Yeah, it reminds me he's got that one essay. I think it might be in Startups Equals Growth about the hill climbing algorithm, and you basically always try and find the next highest hill, and you would think that you could accidentally find a local maximum and not the global maximum that way, but in practice, whenever you're on a higher hill
that's a better way to get to the next hill. And you can sort of always use that way to find your way to the absolute maximum. Uh it's a little ethereal, but uh do you sort of agree with that?
No, I completely agree. I think if you're creative enough and you think about it enough.
you could figure out a way to your next hill. Like any hackers today
is to my knowledge like the biggest online community of startup founders.
Any hackers in its first month was like a blog. Yeah. There's a lot of blogs out there. You start off with like a very tiny hill, and like I made the blog as big as like I think
you know, I wanted to and like maybe it could have been bigger, but it was pretty big. But like there's always some way where you can say, Okay, now I have this advantage that I didn't have last week or last month or last year. Like what ways can I use this advantage to like, you know, parachute over to that like slightly bigger hill? And maybe you like lose a little altitude on your way there, but then you're on this bigger hill.
And it's much easier
Uh the analogy I like to use, maybe not hills, is like a staircase, right? Like a lot of people wanna like
jump to the top of a staircase, right? And it's very hard to jump to the top of a staircase. Like very few people are capable of that feat, but it's pretty easy to walk up a staircase one step at a time.
And so I think a lot of being a founder is just figuring out how you can go one step at a time.
even if you have some grand ambition, how you can start like super small and then kind of work your way there.
I love that. And 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 Startup Founders.
Startup founders.
That's cool.
I mean they're they're any hackers. Like they don't 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
uh realized like oh wow like my you know I like I'm making some side income and then a few months later like oh wow like
I can quit my job.
And then at some point, like you're making a lot of money and you're thinking, Okay, well, like what do I want to do? Do I want to retire to a beach somewhere? Or maybe like what I want to do is build something even bigger.
So a lot of indie hackers I talk to are like are no longer even indie hackers. They've raised money, they're building bigger companies, uh, and that's like where their life path
Well that's what I think is so cool about this. Like
Unless you would disagree. But
I don't think being an indie hacker means like you don't want to raise money or you don't want to build something big, right? It's like you want to build something that people want and the customers will pay you for.
And
Go from there.
And sometimes those become
Notion. Right? Or like and sometimes they become indie hackers and sometimes
They become
Just a business that makes you a couple hundred thousand a year. Yeah.
Exactly. Like I don't
like to juxtapose indie hackers like as a as a counterargument to like raising money so much as it is a counterargument to like having a boss and working like a desk job
And wondering what if for the rest of your life.
Being an Indy hacker is really about the idea that
Like you can achieve your own sort of freedom, whatever that means to you. Maybe that's financial freedom, maybe that's creative freedom, so you can work on whatever you want. Maybe that's like time freedom, so you can work whatever hours and schedule you want.
And so being an Indy hacker is really this like this confidence in yourself that like, hey, you can create something that
That'll make your life better, really, and make other people's lives better in the process and give you that freedom. And maybe that looks like raising a ton of money in the future. 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 gonna raise venture dollars, you're on a path. You're on a very specific path. If you say, I'm gonna build something profitable that funds itself,
You got all the option value in the world to continue to take it whatever sort of trajectory you want to.
Yeah, exactly. And
The kinds of companies that I've seen people build.
Like I almost feel like we need a new word. Cause you think about business, it has all these connotations. Like you mean you imagine like a bunch of men in like suits and like a boardroom or something, you know, reading like graphs.
Uh and then like the word startup is like
Not quite right, it's closer. And it's like
Internet enabled. Yeah, yeah. But they're still the same thing. Exactly. Like there needs to be like some like I don't know what it would be, like some third word where I'm just like looking at people
Like I interviewed this founder, uh Sam Eaton on the podcast earlier this uh this year.
And like his sister at some point was like, I wanna sell cookies. And he's like this software engineer who's worked in like growth roles at Airbnb and he just gotten a job offer at Google. And he's like, No, we're not just gonna sell cookies. We're gonna have like a cookie company and we're gonna like be tech enabled and we're gonna have an app and like all sorts like our own fleet of delivery drivers. And like he's just in heaven sitting around like coding his own apps.
Like they don't use Uber Eats or DoorDash, like they have their own delivery drivers, their own sort of internal mechanism. His sister's like the head of cookie R D, and they're making like a hundred grand a month selling cookies to their local town and he's doing all this cool tech stuff and they have like fifty percent margins too. So like they're living a really good life.
And it's like
It's not just like
your traditional idea of a business. You know, he's like trying to like make his community better. He's trying to make his life better. And he's not stressing over like how fast can we grow and how much bigger can we make this. He's thinking about
You know, like what do I like to spend my time doing?
Well at the same time he's like kinda getting rich and making everybody feel great.
I think this is like such a
Big
movement alongside
You know, the
traditional startup race venture capital, like be something big right off the bat because like
The economic
you know, generation activity generated by this class of entrepreneurs.
Is probably in aggregate going to be equal, if not larger, than like
The Rockefellers of the world.
Did you guys watch that series, Chernobyl? It was on HBO last year. Oh, it was so good. Great series. Oh no, I heard about it, but it's creaky. They like timed it so like right after Game of Thrones went off the air, they're like, boom, here's another series. Don't unsubscribe from HBO. But uh the uh
They kinda boiled down the entire story, like the work of like this one scientist. And it was like an amazing story. It was great, but like obviously in real life, it was probably dozens or hundreds of scientists and engineers working together.
To try to figure out how to contain this nuclear disaster.
And like the reason why they did that is because it's just easier
to tell a story about like one person. And it's the same in business. Like it's easier to tell the story of like one company. We're all fascinated by like how big Apple is and the impact that Apple has. Or like, you know, McDonald's is crazy. Like they have twenty thousand restaurants.
And the United States.'Cause that's like the easy story to like to understand and to tell. But I think
Like the much more impactful story.
is like there're six hundred thousand individuals who have restaurants
in the United States. And like that's way more impactful than like McDonald's having twenty thousand restaurants, but it's a harder story to wrangle. It's like a harder story to tell and to connect the dots.
And I think the way I look at what I'm doing with any hackers is like I'm trying to like connect the dots of all these really tiny tech businesses that are never gonna make the news. You know, they're not
you know, Amazon, they don't have a two trillion dollar market cap, but like what happens when like a million people
are building businesses and make millions of dollars online. You know, what does that look like?
When this comes out, we will likely have just done the DoorDash and the Airbnb IPO episodes. There is a narrow set of
practitioners, whether you're a founder or an employee, who can learn from the tactics and the playbooks accomplished with DoorDash and Airbnb.
But based on all the media coverage, that those are the stories that get told, because that's the simplest and most interesting narrative. But if you're looking to actually learn,
Like let's say Indie Hackers continues to grow and expand and you figure out more ways to parallelize it, and at some point there's, you know, a hundred thousand stories of businesses and the playbooks that
they ran on your website.
Like
Someone can find an incredibly narrowly applicable
business that's just three years ahead of them and run their playbook on their own business in a way that is far more useful than the one story that everyone focuses attention on.
Yeah.
Exactly. That's kind of the the goal of like a lot of the things that I'm building on indie hackers. Like, oh how do you see like these companies
like very early days, and then how do you like filter down to like a very specific niche so you find the company that most matches the profile
of what you're trying to build.
And so we have like this directory.
But I kinda half hazardly built like two and a half years ago and I was like, Oh, we should have a directory of products.
And I like I haven't touched the code in like two and a half years. But like when I built it, it was like okay, we had like fifty people on it and I checked the other day and there's like twelve thousand products on there.
And they all have like a little timeline where they're like saying, Okay, here's what I launched and here's what I thought about my launch and I thought I was being ridiculous saying a hundred thousand, but it shouldn't be long. No, it shouldn't be long, you know, and I I think
It's just a resource that needs to exist. Like you need to be able to go out and see how other people are doing it because
That gives you I think the confidence.
To go do it yourself.
When you see that someone who's like not that different from you, like kind of put their playbook online.
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I'm gonna do David's job here. So uh take us from the light bulb of task force should be making money to the founding of Eddie Hackers. How did that period of time happen? Yeah, I'll give you I'll give you the whirlwind story. So
At some point during the summer after Y C
Stripe came out of Stripe entered the beta phase. So this is like two thousand eleven and Stripe's like, Hey, uh you want to make money with your product, go for it.
Were they in your batch or were they they were before you, right? They were before I was, like maybe by a year or two. They took a a while before they got their patch for the point where it was ready, understandably,'cause there's like a lot of regulation dealing with banks and stuff. But uh they kinda launched into beta
And we got like a good first look because we were kinda on the Y C mailing list. So like we
threw up kind of a stripe subscription in like maybe like a day or two, just like over a weekend.
And the next weekend, I think we made like three thousand dollars in payments, charging people like five bucks a month for like this crappy to do list Chrome extension. Like I thought we were gonna make like a hundred dollars or something. And I was like, Holy shit, like we can like kinda pay our rent. You know, like we can pay for stuff with this.
And so of course we went to the Y C partners were like, Hey, look at this, this is cool. Like we're making a few thousand dollars and they're like
Yeah, but what if you were making like way more and a different idea that wasn't a tiny Chrome extension? Which in some ways is good and bad. In hindsight, if we had stuck with what we were doing.
We could have
probably grown it to a much more substantial size and iterated. Uh instead what we did is we like did what you should never do. We just completely sort of over from scratch with an idea that we thought was like bigger and better. And we sort of violated that principle of like taking it one step at a time.
And so probably over like the next six or seven years
I started
Five or six different companies.
Each one, you know, got to a point where it made like a few thousand dollars in revenue, but it was never really a big deal. It was never like the success that I really wanted.
And I think this is kind of an important
thing that I realized. Like the first couple of years
I was just like
Paddle to the metal.
on my computer every day, coding as much as I possibly could. Like this is gonna be it, you know, like
I'm gonna succeed. Like this is gonna be it, like it has to work. And like it never did.
And not only did I not succeed, but I also just like wasted a bunch of time, like not living a very fun and productive life. Like I don't even remember
like one or two of those years in my lives'cause I was like literally just doing the same thing.
Every single day.
And now my my model that I have for it, kind of frameworking the way I think of it.
And the way I wish I had thought of it then.
was that
Everybody's kinda got like
Like a certain number of companies that you need to start before you succeed.
For some people who are exceptionally talented or lucky or both, like that's just one. They're gonna succeed right out of the gate. Some people maybe it's like thirty five. For me, it was like seven.
And
Really all you need to do is just to make sure that you like you don't quit before you get to that number. Like that's really the entire name of the game. Like just don't quit before you get to the number where you succeed.
And so you should just structure your life to make it so it's easy for you not to quit.
And to make it so that like the journey itself is like actually pretty fun.
And you're learning a lot along the way because like you're not just building a startup in a vacuum, like you're meeting people and you're picking up new skills and you're learning new things. And like like it the startup is kind of like
The journey is as important as like the destination at the end of the day.
And so n nowadays and like eventually I kinda figured it out, like oh I'm like learning so much stuff, like I should make sure that like I'm really enjoying my life while I'm building stuff. So
The last few years there before I ended up starting any hackers are actually really pleasant.
And I feel like I I kind of leveled up as a person while I was building my startups instead of just sort of like
You know, worrying every step of the way, like Am I there yet? You know, is it gonna work? Is this gonna be the one?
Hm. That's such a great lesson.
And just like a couple of points of clarification, were these all inside the same like entity or or was it different co founders or how how did that sort of technically play out?
Yeah.
First one or two were kind of inside the same entity.
And then my co friend and I split up.
And we kinda just declared our Y C startup dead. Like this is you know, this is the end. I think I quit.
And he kinda like bought me out.
For my shares.
And then I just kinda did my own thing.
Yeah, like
By that point I realized okay, what I need to do is figure out how to like make this last. Like I wanna spend the rest of my life
just working for myself on whatever I like. Like I don't want to go get a job.
Part of it was like I just didn't like the idea of having a boss.
Like me working at Stripe today is the first full time job that I've ever had. Like I just don't like to be told what to do, I guess. And and part of it was like this like I don't know, this pride of like I don't want to have to interview somewhere. Like I don't want somebody to be able to reject me. Like I'm I wanna be unrejectable. Like I don't wanna ever put myself in a position where somebody could say, No.
And so like, okay, I just want to keep doing this myself. So I would just like
survive off of kind of my income from some of these apps because I would keep them running and they would make like a few hundred dollars a month or a few thousand dollars a month. And then when I got low on income, I would just go get a contract job.
And then like work on the side.
Et cetera, et cetera. And just kinda like make it so I never had
to quit.
Yeah, but I think
There's a lot said about startup failure, like okay, maybe your maybe your ideas fail because like the market was too small or because you know your product took too long to develop or you ran out of money.
But my my take on it is kinda that
None of those things actually kill your company, you know. Like those are just obstacles, right? Like so your market wasn't big enough and then what, right? Like you quit. Like you didn't have to quit, right? You could have like that's kind of like
If you imagine like a startup journey like being like you walking from like you being an early pioneer walking from the east coast to California.
Right. Like those are just like obstacles. There's like rivers and mountains. And like you can kinda like step over those or go around them, or you can just be like, Fuck it, I'm just gonna like stop here and just live in Kansas.
You know, and like you don't wanna stop and just live in Kansas, like you wanna keep going and find a way to keep going. And so for me that was just living super frugally and figuring out a way to like start the next thing, which meant taking on contract work.
And and building up my savings whenever I needed to.
Yeah.
default alive or uh
At one point I ran a startup weekend in Seattle and Bo Lou, who actually I think went on to do Y C with his company future advisor and uh and Sequoia funded it. Um, he gave this great talk called You're Alive as long as you're not dead. And he was like, Yeah, lots of things bad things can happen at your company, but as long as you don't shut it down
You have not failed. Like your company is still in the act of succeeding. You're not successful yet, but you're in the act of succeeding until you call it quits. Exactly. Yeah. And even if you do quit a particular company, like I've quit lots of different companies, but like as long as you don't quit your overall journey, like you're still on that path. You know, you're still headed to California and you like you're gonna eventually get there. Who knows how many startups it's gonna take.
But you'll get there as long as there's sort of learning and you persist. So
Uh, I think the most important thing you can do is figure out how to keep going.
All right. So
The genesis of indie hackers.
Genesis. How did that happen? So I just rolled off a contract job.
And I had about a year of runway in the bank.
So it's like okay, here we go, like take four. I'm gonna I'm gonna figure out like something to work on that's gonna work this time. And you know, worst case scenario, it's gonna all fail and um I'm gonna go back to working contract jobs.
Uh and so I started working on this one app that I called Knox.
And it was kinda like this ment clone for your phone that would like buzz you with your finances.
And like maybe like
Two or three months into it, I was like, This is an endless slog.
of coding. Like this is gonna take me forever. I don't see like the end of the rainbow. Like I need to just call it quits right now. Like in the time where I was working on that, I saw a couple stories in hacker news of people who would come up with new ideas and were already making like five or ten grand a month and like I hadn't even launched my thing yet. So I was like, okay, this is like a dud. I should scrap this and go back to sort of the drawing board and figure out
You know, what can I like?
What are all the different lessons that I've learned after years of doing this? Like let me make sure like I'm systematic in how I approach this. So I'm not just kind of making the same mistakes again. Cause I'd repeatedly made this mistake that a lot of software engineers make where we just, you know, spend way too much time coding.
And like I think the biggest lesson at the top of the list was like
Only work on things that you can build in like a few weeks.
Yeah, like I went from idea
to basically launch with any hackers and exactly
three weeks. And it didn't require very much code at all. It didn't require like a lot of marketing or anything. It was just like super, super
Easy.
I think this is one of the levers that a lot of founders like don't realize that they can pull. Like everybody's trying to figure out like how do I get enough money to work on my idea? Like do I need to fundraise? Do I need to, you know, borrow money and go into credit card debt.
And like the other lever people pull is like, Oh, how do I get more time? You know, maybe I'm gonna work nights and weekends and all this stuff and like I'm gonna work a three day work week instead of five day work week.
But I think like the third level that's probably the best is like how do you just start smaller? Like how do you figure out like what's an easy even easier thing to do? And for me
My idea was kind of like okay.
I wanna build kind of an anti hacker business so I can sort of, you know, pay my rent, pay my bills, and then figure out what I want to do next.
A ton of other people clearly want to do this. Like I see them on hacker news every day asking all these questions to people who've done it and sharing their stories.
Maybe what I can do in a very meta sort of way is build
a better version of these hacker news discussions. People are always talking about this, but their stories kind of suck. You know, they're like leaving out important details and like everybody in the comments is asking them, like, well how'd you come up with your idea or how much money are you making? And like that's not necessarily in their stories.
If I can compile all of the stories
That I found.
And tell them in like a really compelling way. I make sure I always ask for revenue numbers. I always ask for how they come up with their idea. I always ask about technical details.
And I can put that in one place.
Then I'm making life easier for like both me and a bunch of people who are like me.
who are trying to figure out how to be indie hackers themselves. So that was kind of my idea.
kind of phase one. Like I didn't have a revenue model. I didn't know where I was gonna go from there. But I was like, that's a really easy place to start. All I have to do is email some people
and you know, get their information, put it on a blog and launch it and like I'm a hundred percent sure.
people are not gonna use are gonna eat it up because they've already been eating up stories like this before.
And is the idea that this is gonna become a business for you at this point, or is the idea really like this is a project, I I have it
envision in my head, I know the scope, I know how to build it, I think people are gonna love it.
But it's a project. Hundred percent is gonna be a business. I don't know how I'm gonna make money yet, but it's a hundred percent like at some point, like I'm gonna start in this really small pool, you know, I'm gonna build I'm gonna take the first step on the staircase and do something that works.
And then from there.
I'll have some advantage that I don't have today, like maybe I'll have an audience, maybe I'll have a lot of traffic.
maybe have a big mailing list, and then from there it should be easier for me to figure out how to make an actual business.
The
Revenue aspect.
maybe revenue and profit aspect of
The stories you were telling.
Was that super key? Like I'cause I can imagine, like you know, when you're trying to find like oh yeah, you're s talking all this game about like how great it is, all the stuff you did, but like
Is it actually working? Like, you know, give me the like like that feels like s almost like the like the zest imit before Zillow, right? Like, you know, it's like, hey, this house looks good, but like what's it worth? Like you know, do you uh how important? Extremely important. Like if I could write a startup book, I would call it uh problems first, where like the first thing you want to do is you wanna figure out like
What are the problems that your potential customers have? So you don't build like some random
product that like doesn't solve their pain points.
And when I was like reading all these comments on hacker news, like I was trying to find a business idea. And I didn't want to read comments from people who like didn't have proof that their business idea worked.
You know, somebody said, Like, Oh, I've got this great company I'm working on and it's really great, you know, it does this and this and this, and like they don't share the revenue numbers. Like for all I know, they're making like five dollars a month, you know, and it's not that great.
And I could tell everybody else in the comments like had kinda the same problem. They're like, Hey, we only want to upvote the stories that share their revenue numbers. We only want to upvote the stories that have like some sort of proof or some sort of like inspirational thing that we can like grasp onto to know this person.
Is legit.
Anybody can give you advice and tell you what to do, but if there's no like outcome that's a result of that advice, you don't know if it's good.
And so train your model on garbage data. Exactly. And so like that's a a thing where like there were a lot of other interview sites on the web.
that talk to entrepreneurs, there are pretty much none at the time that realized how important it was that like you needed to be transparent. Like you needed to include
revenue numbers. And so when I went out and I started emailing people and saying like hey
Uh you know, w
My name's Corland. I'm starting this website. It's gonna be called Endy Hackers. Like, will you tell me your company story? And oh, by the way, like I need like all your revenue numbers. Half of them were just like, fuck off. Like, why like you're you're you're nobody. Like, why would I give you my revenue numbers? And then like half of them didn't respond, and like a tiny percentage were like, Hey, you know what? I think this is super cool. I'm happy to pay it forward. Somebody, you know, did the same for me.
and the past. And so by the time I launched I think I had I'd gotten like ten people
To agree.
to share their entire story and their revenue numbers.
When you launch it.
You built the site, right? So like
You didn't go to Squarespace, you didn't go to Webflow, you did what what was the thinking behind that? Yeah. So I had a couple
sort of reasons for that. Part of it was I had a bunch of other ideas that I had come up with.
and my brainstorming and any hackers kinda scored the highest on my rubric because it was so quick to build.
But I felt really bad'cause like here I am the software developer, like
From building all these other startups, like I learned so much stuff from building startups over the years and like failing time and time again. Like I learned how to design and learned how to do front end development and back end and like server admin stuff. And
Here I was like going to start a blog. So uh I was like wow, this is such a waste. Like I want like to throw myself some kind of bone to make this fun. Ca starting a company should be fun. Like you should enjoy the the journey, not just the destination. And so I said, Okay, well, I'll do a blog, but I'll allow myself to just build like my custom blog from scratch.
Even though that's gonna add like another week and a half to my launch time or whatever, like I'll allow myself just that little bit of fun.
And then part of it was
kind of a branding and thinking like
Stripe revenue connect. Building a community and like that was like kind of in the back of my mind the community stuff, definitely not like the product directory and stripe revenue stats or like a lot of the stuff that exists today.
But like I did have kind of a strategic
sort of session with myself. So I spent like one day just thinking strategy. Like'cause in the beginning of your company, there's a bunch of decisions that you make that are much harder to undo.
later on like you'll tell yourself, like oh I'll use a crappy now and redesign it later, but like
Really that's a lot of work and you have a lot of more urgent things. You know, you say, Oh, I'll have a crappy name now and have a a better name later, but like really like it's hard to change your name later on.
So I'd been bitten by like all these issues. And so I said, Okay, I'm gonna take one day and make all of these like semi-permanent decisions. Like what do I want the color scheme to be? How do I want the site to work?

And kinda the three decisions that I came to were
Number one, I want the site to be named after
kind of a new class of people. Because I was like, Well, there's no name for like these people and these
in these discussions. It's like really hard for them to find each other even because like there's like what do you even search for? Like story of person who bootstrapped startup and makes five thousand like there's nothing to search for. So hard to find. So it's like I'm gonna call it any hackers.
I had a bunch of like worse names, but Andy Hackers was the best one I came up with.
I decided I wanted to make the site like
Blue. So it's like this very dark blue that's like probably not very accessible and kind of hard to read. But every other site in in existence is just like white with black text.
Everybody was writing on you know medium it all looked the same and so I I wanted mine to stand out.
But if you ever read
two Ny hacker stories, you would instantly remember that you'd been to this website before.
And then I wanted to do it custom.
Because
I just didn't want to build on somebody else's platform. Like I didn't like the platform risk.
I've been kinda burned by that before, building on Gmail and
you know, they would change their API all the time and like kinda break our apps. And so I didn't want to deal with like, you know
putting up a blog on medium and having it look like every other medium blog and then
medium changes their business model or something and now I'm screwed.
So those are kinda like the three decisions I made back then, and all of them I think turned out to be pretty good in the long run.
And the etymology of the name, it's interesting thinking about when you started this, the notion of an indie developer was already a thing. I mean, I remember
considering myself an indie developer in two thousand and eight when I started working on my first iPhone app.
And I think Craig Hawk and Berry and a bunch of the like icon factory people, they they were saying, Oh, I'm an indie developer, indie, you know, iPhone or Apple developer. And obviously hacker news was sort of like a a thing, but those communities were basically non overlapping. Like hackers were
what people who were technical and wanted to start high growth technology startups refer to themselves as, but indie's were what the like
Lifestyle.
developer community primarily center centered around Apple platforms kind of called themselves. Yeah. And I wasn't thinking about like honestly any of that Ny stuff. Like it wasn't even I wasn't even aware that they're like Ny developers. I was just like, okay, well like I want like the idea of like an independent programmer. Because again, it wasn't so much a rebellion against raising money. It was a rebellion against
You know, going to work for the man.
And like, you know, making Google ten million dollars a year from your code, but you're only getting like two hundred K of that, you know? Like why don't you start your own thing and be like kind of your own N D developer?
And hacker news was so called because like hackers are just another word for programmers. So the idea is like okay, you're a programmer, but you're independent. There's no cap on your salary, you know, there's there's really no limits, like you can do whatever you want.
Yep. And before we move on from this point, talk to me about platform risk, because in my mind
you know, we think about this for acquired too. We're we're always trying to get the most direct relationship possible with our listeners, with our LPs, with our, you know, with everybody. And
there's always some platform risk. Like we've collected email addresses from one out of, I don't know, six or seven listeners, you know, all from all the various reasons that people join our Slack or they sign up for the emails, which, you know, now have the playbook, so there's even a further incentive to sign up for the emails. But at the end of the day
Even if you have someone's email, you know, you could go to their promotions tab. Like you never it's not like you can call that person. Th there's always some amount of indirection between you and and your end customer. So
How do you think about how far you should go on
Eliminating platform risk.
Yeah.
I think
everything in business is basically a trade off. And what you really want to do is just be like aware
of the trade offs that you're making. Like there are no hard and fast rules like never build on a platform, right? Like if you build on a platform maybe can give you additional distribution, but then you get the risk that they might shut you down or change things, or you might like lose out on the branding or the ability to differentiate yourself, et cetera. Like maybe you can charge a high amount of revenue per user.
But that means you're gonna get, you know, maybe fewer users in the door, fewer customers. But then also you can spend more to acquire your custom it's all trade offs.
And so for
My particular situation when I looked at that trade off.
Like really the only contender was like okay, I can like maybe try to build a big Twitter account where I share these stories.
I can repeatedly, you know
post on like Reddit or Hacker News.
Or like I could have a kind of a medium blog. Like those are the big platforms that I considered.
And every one of them I thought would give me
Either very limited distribution. Like how much did medium really help with distribution? It was kinda hit and miss.
Um and they would also just like
completely destroy my ability to have any sort of branding.
And I knew that kind of step two in this playbook might be to build a mailing list or a community. Like I wasn't sure, but I knew that like if I was gonna name it and be hackers and like go for something where the brand actually mattered, which I think is important if you're gonna have something where it's kinda like free and I was just getting like lots of users in the door, but I didn't have a business model, then I wanted to own my brand. And so it wasn't worth it for me
to use any of these platforms, even though they would help with distribution.
If I could instead just like do my own.
And I also had like kind of my own distribution strategy. I already knew that people
we're gonna be eating this kind of stuff up on Hacker News because they already were.
And I already knew that Hacker News had like a lot of traffic. So it's like, okay, I don't need medium, you know, I can do it on my own. So like I get like no real benefit from medium and I get all this additional risk. Like the trade off just wasn't worth it.
It's kinda funny. I mean in some ways you maybe ran the uh uh the Airbnb playbook of um
Exfiltrate Craigslist. Yeah. You did for this segment of Hacker News. My buddy uh Greg Eisenberg has this whole idea of like, you know, unbundling Craigslist, unbundling Reddit, unbundling hacker news. It's a huge community. There's all sorts of sub like discussions happening in there that happen regularly. Totally. There's a
It's a pretty big tent. Exactly. So
You but you build the site.
What's the block on your site?

As I understand it.
Pretty quickly you figured out that email
was a pretty big unlock.
Kinda on both like four.
The interviews you were doing.
Call it the
supply side of these stories.
And for
Readers for the demand side. You can almost imagine the web is like
It's collection of like
feeds or like destinations and some of them
are places where people go like habitually. Like I habitually check my email. I habitually check the notifications on my phone. I habitually check Twitter. I'm just like addicted. Like I'll sit down and just like press T on my keyboard and like black out for a second like I'm on Twitter. And then there's other places where like people just don't have a habit. Like I made any hackers. No one on earth had a habit
of regularly visiting ND hackers. And they weren't gonna have that habit anytime soon because I was publishing like once or twice a week, you know? Like Twitter's got new content every single minute. So uh for me it was like okay, well how do I hook into like one of these feeds that everybody already habitually looks at.
And it it was a combination of both Twitter and email.
So I made like the Twitter Andy Hackers account.
I tried to tweet every story that I had so that you would sort of incidentally run into them when you check your Twitter and be like, Oh, yeah, I remember Andy Hackers, let me go back there. And then email was a huge one,'cause like I actually own
the email addresses when people sign up. Like I can take that with me anywhere. Like like you can't shut down my email list.
And so from day one, like I had kind of a email collection box at the very top and like at the bottom of every interview, just trying to get people's emails.
And I think in the first week.
We got like a thousand or fifteen hundred emails and it was like kinda continued on that pace for a while, like a thousand emails a week.
From people from Hacker News and all over the web who just like loved these success stories. Like they would come and read them and they would be like so inspired to hear that like
You know, so and so was making a ten grand a month from like their travel startup and like I'm a developer, I could do that too.
And so they would immediately get on the email'cause like they want more of these like stories, you know, they want more
um glances at like what's possible so that like in when the day comes that they're ready to start their startup, like they haven't forgotten where to go to see those examples.
You gotta have some reason
That like you're gonna show up for
people. Like w one of the things you know
I kinda joke about it. I don't know. There's no way to scientifically know, but like and we didn't plan it this way, but the fact that our podcast name is ACQ, like in almost everybody's podcast feed.
We are at the very top'cause for whatever reason, podcast feeds are organized alphabetically. And like
How much benefit have we gotten from that? Like I don't know. But probably pretty sure we've gotten a a
Yeah. Yeah. It's a hard one lesson for a lot of people who are starting startups. Like if you're an ND hacker, you don't have like a bunch of investors and mentors, like you probably just kind of by default believe like a you know, if they build it.
If I build it, they will come. You know, I'll just build some cool stuff.
and get a bunch of people like in the door. But it turns out that like
Building stuff is kinda easy. Even like even if you're not a developer today, like you can stitch stuff. Like I talked to a guy yesterday who built like a whole Slack bot without using code at all. He doesn't even know how to code.
And uh the hard part is like getting people to actually care about what you're building and actually find it. So that means like you have to actually solve it. Well, it's like and then run into it. Yes, and run into it. And run and it's not just run into it once. It's like run into it like repeatedly all time. Repeatedly. And like that's very hard to do. But if you think about it like really carefully before you start.
then often like you can come up with something. Like what I found is helpful is like you just go to
one of the places where people find things and you just look at what they're sharing.
You know, that that's kind of accidentally what I did with indie hackers. Like I was already in hacker news and it took like days of me reading these threads before it clicked like, Wow, everybody is here sharing this thing. Like why don't I just like make my thing better than what they're sharing here and then share it in the exact same place.
Okay, so we've talked about like the this insight that you had that enabled growth. So you know, we sound like uh
circa twenty eleven Y C, you know, like tell me about your growth rates. Like now let's now let's shift to the indie hacker conversation. How did you start making money? Yeah. So
Actually what happened is like my very first
sort of hit of revenue was completely unexpected. It was like maybe two weeks after I launched
And some company was like, Hey, can we sponsor you?
And I was like
Sure. Uh how much do you want to pay? And they're like, how much traffic do you have?
And I told him like sure we well we'll give you like seven hundred and fifty bucks a month.
And that to me was insane because everything that I had ever built was like some like rinky dink consumer app where I was like begging people to pay me like five bucks a month. Yeah, pennies. And people were like, Well, no, it doesn't have this feature. I can't possibly afford five dollars a month and then they'll go like buy like a bat coffee and like dump it out, you know.
So like this company like offering me hundreds of dollars like was like a wake up call, like oh I can like make money from sponsors.
But I was also like super focused on growth because I was thinking, okay, well, I've got like maybe six months of runway, and I've got six months of savings in my bank account.
I've got time. Like why don't I just grow the site even bigger?
Because there's only one of me. Like I don't have that much time to try to sell ads and build a site and do all these interviews I'm doing every single week.
I'm just gonna grow it, not worry about money.
And I'll worry about it later.
So I did that for like three months. I just kept trying to grow the site. I didn't figure out how to grow the site at all. I did like never found something that was bigger and better than getting on the front page of Hacker News go figure. And so by December, I launched in August. By December I was like, Okay, screw this, I'm gonna start trying to make money.
So I started like basically emailing my list.
Which at that point had probably been growing to like ten or fifteen thousand people.
Uh and saying, Hey, like, you know
Here's the email with the new like this week's interviews, but also by the way, here's an empty ad slot. Like your company could be here.
And I was very lucky that literally it's the billboard that you see with the like your ad could be. Yeah, it was exactly that, but in an email form. And I put that on the website too. And like it turns out when you have a company that targets people who are starting companies, you have a lot of potential advertisers on your mailing list who all want to basically advertise with you.
And it also turned out
Which I didn't realize at the time, that indie hackers were like some of the worst possible customers to buy ads. Because like these are very fledgling startups. Like these are people who had decided to start something because they read about it on Ny Hackers like two months ago. And if they were gonna spend like five hundred or thousand dollars on an ad, like that ad had better work. Like that's not
That's like their whole yearly ad budget. And so I it's almost like you would want a company that is selling tools to people. I almost like that. So I went through like a lot of these awkward conversations where I'd run ads where people like I just wanted to do right by them, but like the ads didn't always get enough clicks and sometimes like I would refund people.
And it was just like very stressful. I didn't like doing it. And so I created kind of like a dream list of companies. Like, okay, which companies actually have a lot of money that would be good sponsors. Like I've no I've no experience doing sales, but like I'm gonna have to figure out how to do this.
And I had at the very bottom of my list, like my number one dream company who should be sponsoring any hackers was Stripe.
I'm like, okay, I'll eventually get to them. But like I wanna like figure my I'm like I want my shit to be good. Yeah, I need some warmups, you know? And so I don't warm up on Broadway. Exactly. You don't want to like embarrass yourself in front of everybody. So I got some warm ups. I sent a lot of cold emails.
I found like the heads of marketing on LinkedIn.
Uh my buddy Jeff, who ran a podcast I was on, uh gave me kind of his list of leads for he was advertising it on his podcast.
And like to my surprise, it was like way more pleasant selling to big companies than it was selling to small ones. Like I would get someone whose entire job it was
to spend a marketing budget. And they would just want to talk about their kids, talk about their vacations, and then be like, Oh yeah, you're cool. Like here's a check for five grand.
And I would be like, Holy shit, this is a thousand times easier than selling the people who are broke.
Yeah, and not to mention like
one of my key startup lessons learned over the years has been sell to things that have budgets. Like don't try and create budget fit into a budget. And sure, there's emerging markets where like the budget line item is not going to exist for your thing, but
You're so right that if if there's somebody whose job it is and they have a budget to spend, like your life is just gonna be so much easier.
I think that applies to even
coming up with startup ideas and trying to figure out a business model.
Like it's kinda counterintuitive.
Like people repeat this mantra, like, you know, solve an unsolved problem.
And it's almost like you want to do the opposite. Like you want to look at problems that people are already paying a lot of money to have solved and kinda like
Insert yourself there.
Like my friend started a company called Key Values. She's like been one of my best friends for years. Her name is Lynn.
And like her company helps
Startups hire engineers.
And you know what? Like startups are hiring engineers just fine, like well before her company came along. But like we kinda picked that idea because we looked at like well, where are companies spending money? You know, like where do they spend a lot of their money? And it turned out like hiring engineers, hiring recruiters was like a huge
huge cost in it for companies and like they were just willing to spend a lot of money on it.
And within like a year of starting her company
She grew her revenue to like a hundred grand a quarter. She was living like a great life. She made it look easy her first time out of the gate. In part because like she picked a problem where like people had budgets.
Right. And and and I think the insight here is like if you really want to overly simplify the sales process, there's educate.
And then win.
Like educate people that their need is real. And then once they're convinced that they want to solve this problem, then go win and be the way that you solve that problem for them. And if you're selling into people with budgets,
You don't really need to educate'cause they're totally bought in on solving that problem already. Yeah. And education is hard and it's risky,'cause you might educate somebody and then lose because someone else comes along and wins.
Yeah.
Or more frequently you educate somebody and they're like eh. Yeah, then I've got these other things that like I need to solve. All right. So
Broadway comments. Yeah. So I I don't know, I'm selling ads for like a few months.
I'm just happy to be honest,'cause I got to the point I think in
February twenty sixteen where like any hacker's gonna pay you all of my bills. And I was like, Wow like
And less than a year I've gone from like, you know, nothing to finally like one of the ideas I've done works.
And so no none of the other companies you'd worked on you'd gotten to this point where it's like
Revenue is covering my personal expense. And it was better in like literally every single way. Like I eventually like I had added a community and so people were sort of talking to each other.
So I began to see kind of a path where like, oh, I can do less work. Like maybe people can interview each other and like I don't have to do anything. People really liked it. You know, it was like a a very like I wasn't making to do list software where like all I got were like angry customer emails because I don't have the right feature. Like every email I got was something positive, people talking about how inspired they were by an interview that they heard. Like it was just like a hundred percent good for my life.
in every single way. So I was just like blown away and super happy and just high in life.
And then to make things even better, I get this email out of the blue.
And so like I hadn't gotten to Stripe yet on my on my sort of like list of sponsors to reach out to us, maybe halfway. No, like I think during the stripe beta I had like maybe like gone in their like little stripe chat room and like, you know.
pointed out some bugs and asked some questions. But like I never really talked to the founders outside of that.
Uh and the email like
I just stepped off a plane actually. I was going to a buddy's
Bachelor party in Mexico.
And so I stepped off the plane, I was checking my emails, and like the very top of the inbox was like uh acquire any hackers question mark from like Patrick at Stripe.
And I was just like, holy shit there's like there's no way this email's real. Like this is completely You're getting trolled. I'm definitely getting trolled. But I read it and it was real. And he was just kinda like, Hey Cortland, like really like admiring what you're doing at ND Hackers.
You know, is there any way you'd be open to stripe, you know, potentially
Acquiring it.
And so the first thing I did was like I forwarded it to my mom, sent it to my brother, sent it to my friends. It's the polygram email all over again. Yeah, yeah. It was like the coolest thing ever.
And we ended up meeting and talking and kind of feeling each other out.
Uh at brunch the next Saturday.
And uh over the course of a month like worked out kind of a deal and I joined Stripe in April twenty seventeen.
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Lots to unpack here. Before we get too far into it, I wanna understand let's let's relate it to our previous conversation on educating and then winning. Had
Stripe or and or Patrick?
Decided.
that they wanted to own an asset that was sort of a community of people talking about building stuff on the internet that very likely would need stripe to monetize and then you were the pick? Or was it like
Hey, wow, that guy's really got something cool. Uh I think it's a combination of both.
It's been funny like looking at uh just acquisitions over the years, talking to friends, and also seeing like a little bit of stuff internally at Stripe where like it's just like so like idiosyncratic and like almost random how these acquisition happen in many cases, where it's like just like depending on how a particular person feels, like this seems like the thing to buy.
And I think in my case
Stripe has this kind of cool project internally called like the Crazy Ideas List. And it's like, hey everybody, write down like the craziest ideas. Like
If it's a reasonable idea, it's not allowed on this list. Like you need to write down like just crazy things that we could potentially do that, you know, might win big.
I think like some version of Indy Hackers has been on that list for many years. You know, like what if we have like a community for early stage startup founders?
Just because for a company like Stripe that wins like a lot of
uh business from early startups, like these startups grow. They might be making a thousand dollars a month now, but like
Five years from now they could be lift.
And so like winning like the hearts and minds of early state stars matters a lot. And so that idea was on there and they just like never did it.
Right,'cause there's like maybe a thousand ideas on that list.
And then I started any hackers.
It just worked. It worked really well. And it just like happened to very luckily perfectly align
with what they want it to do. Where it's like, okay, well it's like empowering people to get started and inspiring them. And Stripe is a company that cares like a lot about its reputation. It's not an accident like that Stripe hasn't had, you know, any sort of major scandals like almost every other huge unicorn company. It's because the founders care a lot.
And we like have a lot of good, like, well among founders and developers and like make a lot of decisions at the company that like
or you know, have that in mind. It's like to do best by people. And so anti hackers was like also a huge check in that.
direction where like people just really liked Andy Hackers. Like they liked the positivity, like the optimism. It was all about like how you can do it.
you know how you can kinda stick it to the man and like start your own business was very empowering.
And I think crucially it did two things. It
Inspired people to start businesses.
who previously might not have had the confidence to do it.
And it also helped people with businesses succeed.
And like both of those things are very good for a company like Stripe.
That clearly wants more businesses to exist and more businesses to succeed.
And what were some of your concerns once you started after you got out of the initial wave of Oh my God, then you're like, wow
W would I sell this? Should I sell this? Like how how did you think about some of the trade offs and tensions there?
Yeah, so
A lot of my concern at the time, like one of the things that was weighing heaviest on my mind was like I just really didn't like selling ads.
I was really not having a great time. I mean I was making money, it was like fun fun to get checks.
But like I wanted to make endie hackers bigger and better. I wanted to spend a lot more time
coding the community. Like at that time the community only had like maybe like 40, 50 conversations a week. Now it's got like tens of thousands. And I just wanted the time to do that.
And so I was thinking, okay, well, if I go to Stripe, like what are they gonna have me working on? You know, how much say are they gonna have
and what I'm doing and like how much does their vision align with what my vision is for the company.
And if it's off by even like a small amount.
Like maybe that's not a big deal today, but like four or five years from now, like that could be a huge deal. Like a small gap can turn into a really big gap. And so I really wanted to know, like, okay, are we gonna be aligned?
I wanted to know.
'Cause that's kinda like for the like the betterment of the community. Like the people at Indy Hackers, like it's just gonna be good for them. You know, if you have a community and you have something where like all your users are quite vocal.
Especially if they if they come from hacker news, which most indie hackers did. These are opennated people. These are and they don't like tend to look kindly on acquisitions that go wrong and and watching their favorite products die. So I wanted to know, okay, like is Indie Hackers gonna be better off for this?
I wanted to know if I was gonna be better off from this, you know, how much money is a sacrosancy gonna like make me, right? Like uh how does it compare the whole point of indie hackers, right? Is like exactly if I'm gonna no longer be sort of like technically indie, you know, like what is the trade off I'm making and like how indie will I be?
I had this whole
point that I make to to friends and like they
It always gets like a mixed perception, but like I think everybody's kind of a business. Even if you're an employee, you should think of yourself as a business. Anytime changes hands, you should think of yourself as a business. Uh if you want to learn how to improve your career, like read a business book and think about yourself as a business. And so, you know, as an employee, like, yeah, you might seem like you you have no power.
But like I learned from contracting, like you have a lot of power. If you can make like the value or the the service or product you provide to your employer really unique, like it's harder to fire you. And it's like you're more valuable. You can get paid more, you can get paid what you're worth rather than being paid like very little because you have so many competitors who have the exact same job title as you.
and like you know, that so many other parts of like the employee experience.
relate to being a business. You know, like everybody has marketing experience. If you've ever made a resume, like that's basically an ad.
And when you've like s shipped it out to
You know, potential employers, like that's like basically marketing. And if you've done an interview, like you've done sales'cause you're trying to sell yourself.
So I thought about myself in that light, like okay, well, how much freedom and independence am I gonna have?
as an employee of Stripe, like who am I going to report to? You know, what are they going to be telling me to do? If anything. And I 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 like
You gotta focus on like do it. You can't be like pulled in like Oh yeah, like I know you're doing this thing, right? But like hey, we've got this bug, like can you just like jump in and like fix it or like you know, we gotta do this thing. Like, you know, you can get back to doing that thing, but you we gotta do this thing, like you know. That's also completely different.
And it's it's also like a completely different type thing. Like the average sort of engineer, like a bigger startup, is not like
Someone with a lot of startup experience. You know, there isn't like a roadmap for like here's how you start a large community of founders. You know, there's no like step by step process. Like it hasn't really been done before for some reason. Like there just aren't large communities of founders that have like really thrived online.
And so uh it's kinda easier to wait for somebody else to do it.
Than it is to like pick a random employee and be like
Good luck, you know, you're gonna be able to go make you a star. Yeah, good luck you're gonna be able to I mean, some people can do it, but like that's not why people typically apply to jobs, because that's
And if they wanted to do that, they would go start their own thing. So I was kinda worried, you know, like, okay, what is my responsibility gonna be like? Am I gonna be like a normal stripe employee or not?
And then like sort of the third box besides just like me and the community was like what does Stripe want to get out of this?
I I really wanted to know like what strike wanted to get out of it because it's hard to predict, you know, if we're gonna align if I don't know like why you're even doing this.
And like to Patrick and the leadership teams like credit, like they're just very open minded
Fox.
You know, like they don't necessarily need a ton of proof that something's gonna work.
Right. If something is like directionally pointing in the right direction, then it can work.
Like they're more than happy to take a chance.
And with like any hackers and stripe, it's kinda like
Ny hackers doesn't really capture
a lot of the value that it creates. You know, if people start companies and their companies succeed
Because of any hackers, but because of a story they heard.
Um because somebody helped them on the community, like how do I make money from that? Like it turned out like I didn't.
But like other companies exist that can capture that value, including Stripe, because if Stripe is the best product on the market, like what are they gonna use for their new companies? They're gonna use Stripe. And so Patrick really just trusted like hey
We think that you can make
Andy Hacker is really big, really meaningful. You've done a great job so far.
It's hard to even measure. Like even if you do make it big, like we'll never really know exactly how much has contributed and sort of added when to our sales. But
Like that's fine.
And so
Couple of questions here and I'll ask them together so you know both are coming. Uh you don't have to give me numbers or clauses, but I'm looking for
Yeah.
What do you need to put into
a legal contract in order to allay those concerns and what do you just leave to trust? Because ultimately these these things really are come down to do you trust me, do I trust you and are we aligned? So that's the first one. The second one is how on earth do you go about figuring out what a fair deal looks like based on what your business was before it was acquired.
Yeah.
These are tricky questions and I don't I never feel like the most qualified to answer acquisition questions. Like people even though this is acquired, uh people call me all the time, like, Hey, I'm going through an acquisition, you went through one, like
What happened with you? And like it's so specific to my situation. Yeah. I was like a solo founder with no employees, like I haven't even incorporated. But like there's some like little tricks and and things that help me. So
Uh, the first thing that happened was that Patrick suggested that we communicate over text.
So we like got on WhatsApp, which
instantly like I was like, Oh, this is so smart because like I had been sitting there, like I think it was a Sunday, like typing out an email, like this like sort of acquisition numbers negotiation. And it was like such a high pressure thing, like what am I gonna say in this email? Like
versus text just like so casual. You're just kinda firing off like messages and like it just like lowers sort of the stress
And like almost the adversarial nature of it.
in a strong way. So that was kinda like the first tip. But then I thought about okay, well how do I value
You know
what Indy Hackers is worth. Like what am I gonna be happy with here? And I think your first question was also
Like how much does trust come into it?
So like
The first thing I started doing was trying to answer both of these questions actually through
kind of back channeling. So I just emailed
As many people as I knew
Who either worked at Stripe
had dealings with Stripe or had dealings with Patrick.
in the past. I'm like, hey, what what kind of person am I dealing with?
And I got like
a lot of really positive stories. Like this is a person who cares.
deeply about like what's good for people, et cetera, very ethical, et cetera.
And like I think you need that level of trust because like in a contract
uh as I soon found out, like there's just so many random like loopholes and like edge cases that you haven't considered and just like really easy ways to get kind of screwed over.
Like at some point
Uh, I was talking to Patrick and we were hammering things out.
And at like one point
I got an email that wasn't from Patrick, it was from like Stripe General Counsel. And I'm like, oh shit. Like maybe I should have a lawyer because I don't know what this guy's talking about. So then I went and hired a lawyer and like uh her name was Mattelle, she was great, but she was just like the most paranoid person ever. She was like, Here are all the ways they're gonna screw you up, they're gonna do this, they're gonna do that, they're gonna do this.
And like every single contract that like came, she like found some way to tighten up the language or just like go to bat for me in ways where like
Because I had a lot of trust.
Uh, perhaps naively, like I just would have been like, Ah, it's fine. Like they have like the best intentions here.
Uh and so it's kinda like, you know, trust but verify. Like I had a lot of trust.
And I don't think I would have done the deal if I didn't trust that like
everybody involved was being sincere with what they said, that their like sort of thoughts aligned with their actions and their words.
But also having someone in my corner to like make sure
That these things wouldn't happen was I think important and gave me a lot of security.
Oh.
Well the thing about this
Situations like this is like
Yeah.
The documents and the clauses and all that.
Th they exist for when things go sour. You know, like any time you are looking at those documents, like
Things are on a bad path. You don't ever want to look at them. Yeah. But
If you have to look at them
You know, what is written in those documents is what is gonna happen. So Exactly. So they're important and they they matter. And I think
In my situation, like what kinda happened is that we like agreed on numbers.
But at like in a very like high level, non specific, like this is what would make us all happy way.
And that happened like pretty quickly. It didn't take that long. And like part of that was also doing research, like how much do engineers at Strife get paid? Like can I you know, by that point I was pretty good at getting people to reveal like numbers to me from working on any hackers. So I got a lot of numbers. I was like, Okay, look, this is what I want.
And I was like try to be a firm negotiator. But like you kind of agree on these numbers and then you go to like draw up a document, and it turns out there's like just a million little edge cases, you know, like okay.
I
If you like for example, if you're talking about stock, like what kind of stock do you want? What like what class, like when does it fast, what period is it fast, like how long, uh how to refresh this work, like all sorts of different things that
I think if you're kinda like a typical employee, you might not consider. But if you're coming in through an acquisition
Like the sky's the limit. Like you can
Ask for our demand, like literally whatever you want and put it in a contract. It's gonna be your special contract that no one else at the company has anything that's even like that. So
For me, like it wasn't just like kind of worst case scenario. It was like, okay, well, like now it's this whole like phase two of negotiations where like, you know, talking about all these little details that we hadn't even considered.
You know?
What mechanics did you put in place? Obviously it wasn't like, okay, here's a bunch of cash. Welcome to Stripe. Like it's either stock or it's Vesting or it's tied to incentive based targets for indie hackers, or it's tied to Stripe as a company rather than indie hackers. Like how did you sort of structure the way that
there would be incentives over time for both sides.
I don't know how much I'm legally allowed to say.
Don't even get close. Like I think that what we're interested is like how should people, if they're going into a situation like this, think about that.
I think the first thing to be w aware of is just like all the different options that you have. I think it's very easy when you think about an acquisition to just think like number, you know, this company sold for X amount.
But like that's like
from my in my experience, rarely how it happens. It's rarely that simple. And like some of the other options are just much more advantageous. Like often companies will like give you more equity than they will give you cash.
And if you can sort of like evaluate the company, like if it's stripe
Like for the love of God, like take faculty. You know? Yeah, take the stock. Uh you know, if it's like if it's group on, then like I don't know, you know, maybe you want the cash. And like this is like an exercise I Well, this is the difference I think between you know, like like Salesforce by Slack, it's about the number, right? Like that's what the'cause it's a company buying it's an entity buying an entity. Yeah, corporate entity buying corporate entity.
With an indie hacker business like
No, it's you. It's literally that that's and I think I I don't know what like Elon Musk's situation is, but he has like all these like weird like earn out bonuses where he gets like more money if like the stock price goes up. So even like those big company situations, like there's all sorts of ways to sort of like figure things out. Like, you know, if if Salesforce buys Slack, like what does that mean for Stuart Butterfield? Like perhaps he could say, like I want more money if we hit these extra targets.
et cetera. And uh perhaps Mark Bennyoff would be like sure, that's fine.
And so I think if you can like think about kind of these creative ways
to sort of like align your incentives.
it can, you know, result in like a happier process. And and maybe on both sides. Like maybe your acquire wants to pay you more if you hit performance targets because like the risk for them uh isn't the initial cash outlay. It's that it's not going to pay off in the future. And so if they know you're incentivized to like
to actually do a good job.
then I think that that can be kind of a win win, even though like you know, they're sort of on the hook for more money in the future.
In my particular case, like it's funny because Indy Hackers is very much
an anti hacker business. You know, I was just like making money from advertisers. I had like some affiliate links on the site.
I think it was making like seven and a half, eight thousand dollars a month.
by the time Stripe acquired the company, whereas like today I feel much more like a high growth startup.
We're like Stripe owns any hackers, but they're like almost kind of like an investor. And like my goal is to like grow as much as possible and like I don't make any money, like any hackers doesn't like have any sort of revenue we bring in. We have kind of a budget, which is almost like funding to help us grow. And so it was like it represented kind of like a complete change in how I viewed growing my own business. And I kinda went to this
Uh almost to this like the exact opposite of what like the stereotypical indie hacker company is trying to do.
You know, the comp at that point is more to intrapreneurship, which is such a funny word'cause it's like they took a French word and then changed it to sound like an English word.
Anyway.
What differences do you notice between Indie Hackers, which is a wholled subsidiary of Stripe? And I'm sure that that may not exactly be technically correct, but it's sort of its own brand. It just has a buy Stripe thing on. It's run by you, versus the things that start
Within Stripe, but are there owned.
self contained thing like Stripe Press or like Stripe Atlas.
Yeah, I mean I think branding is the
by far the biggest difference because it's pretty obvious to most most people who are aware of Ny Hackers know that ND Hackers started
before Stripe. And they know that it's kind of like my thing. I'm very transparent. Like they're gonna listen to this podcast and be like clear Quirlin 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 Indy Hackers is owned by Stripe. Like there's like a very small like little logo that says like at like Stripe at the very bottom of the website that you kinda have to search to find.
Which is freeing in a way because it gives me the ability to make my own decisions that don't necessarily reflect
on the stripe brand.
Like I remember a buddy of mine at Stripe who kind of ran like the Stripe Atlas community, like got an email from any hackers. He's like, Oh my God, you said fucking an email, like a Stripe email. And I'm like, I've said fucking like a probably like two dozen of these emails. Uh there's no one at Stripe is like kinda monitoring that. You know, there's a lot of trust that goes both ways. Like I trust Stripe and they trust me. And like it doesn't
You know, it's weird in a way, like a lot of the positive things
And feelings people have about N hackers sort of get accrued to stripe.
But like some of the little riskier decisions like don't weigh on stripe at all.
And so it's almost best of of of both worlds, right?
Whereas I I think if like I you know started some stripe product internally
Like Stripe Press. Like that has Stripe's name, like literally in the name. Which means it's a certain like level of quality that it has to rise to. There's a certain standard that has to rise to. It's harder to get things off the ground when you do that. Like you need to match like certain accessibility standards and have like a certain reach of people in different countries and have all these different languages. And I think it's just harder to iterate on any sort of like
startup type initiative that's trying to find product market fit.
If you have all of these.
Expectations on you.
This is why I think it's smart for like Google.
when they're doing their enervations to like try to like
spin things out of the Google brand and just have them be like dissociated. And so like you d people don't have these expectations. Because you just kinda need to start with something embarrassing and rough. And what I've been doing for the last yeah YouTube's a great example. Right. Like when Google bought YouTube
There was still like the Viacom lawsuit was going on, like there was all sorts of
You know, people were up in arms, there's crazy stuff happening.
Maybe say there's still this crazy stuff happening on YouTube out there now. It's like Google Video was a failing product.
Like it was trying to do the exact same thing, but was going through Google's standard process.
Yeah, they weren't gonna
Just
You know, put movies up on there that were filmed with a you know, camcorder in a theater. Like you can take bigger risks through an acquisition, especially of of like an established brand on its own.
That's really cool.
Alright, so tell us now why has it made sense for Stripe and
I mean, this is a little bit of a softball question, but like how's it going? How's it gone? Was it a good idea for stride to ID hackers? What have you built to do any integrations if you have?
Yeah. So I mean it's worth like
Noting sort of my working style at Stripe is that
I've reported to Patrick since I got here. We don't meet all that often. You know, there have been years where we met like twice. There are years where we I've sent him like weekly updates, not on his request, but on my request, because I just wanted him to know what's going on. Everything I've added to anti hackers, literally everything that I've done has been one hundred percent my choice. There's not been a single request from Stripe saying, Hey, can you do this?
That's happened.
So a couple of things have happened since we joined Stripe.
I remember like meeting Patrick maybe nine months after the acquisition and he was like Oh, this looks really good. Like I was kinda worried that for you to grow
you would sort of have to just kinda run faster and faster. Because when Stripe acquired indie hackers
It was still primarily just kind of a media company. Like we were doing nothing but putting out these interviews.
And we had this like very fledgling community forum, but like it was like you had to like click a link to get to it and it was only like a like a small number of people
Whereas today the bulk of what happens
on any hackers is sort of user powered. It's more of like a an actual platform where like I'm not doing
Like the vast majority of the value that NDHackers creates to the world is like does not come from me. You did it. You shifted from media company to software product. Exactly, which I always wanted to do, but it took Jesus did it take a long time.
Probably I would say like the biggest accomplishment since joining Stripe was just the growth of the community forum, which is now on the homepage. If you go to ndhackers.com, you just see
dozens of conversations where hundreds of people are sort of helping each other out, asking questions.
And like helping each other start companies, meeting co founders, without me really doing anything.
The company profiles you create through interviews.
And that
people create themselves. They're all mixed together. Yeah, yeah, kind of. And I've I've been trying to like
consolidate things are not quite consolidated yet. So there is kind of a separate section on the website where you can go and you can read
I think we've done about five hundred interviews now.
Uh all the different interviews from endy hackers who've s kind of shared their stories. And like you can kinda sort and filter those. You can also go to sort of the product directory, which I mentioned earlier.
Where it's just more like self serve. Like anybody can add a product there. You can share how much money you're making, share your milestones along the way, and everybody sort of there competes to have like the best milestone every day. So we have this loaderboard that kind of resets.
And whoever posts like the best update for that day in terms of upvotes gets to the top of the leaderboard and they get more traffic, et cetera. And so it's kind of a mechanism to incentivise people to fill out these little timelines.
Which has a side effect that everybody else can go read the timelines and learn how to build a company from these examples.
So that's grown to like twelve thousand products. We've got five hundred interviews.
We have a podcast that
you know, went from I think just maybe like a thousand downloads total when Stripe acquired ND hackers to now millions of downloads.
And the community forum has gone from
Just a few dozen conversations a week.
to the point where there's like a thousand comments a day.
Over two hundred and fifty posts every single day in the community forum and just like tens of thousands of people helping each other out. So uh, you know.
Based on the numbers, any hackers has grown like tremendously since we've joined Stripe. So awesome. And one of the things like we like to measure is kinda like
A rough estimate of like how many people have started
Companies.
as a result of endy hackers.
So we kinda send out like a survey to people
Maybe six months or so after they join.
You know, we ask them to say like true or false of different questions and one of them is, you know
Yeah, would you have started your company if not for any hackers?
And most people are like, Oh yeah, I would've started it anyway, or I haven't started yet.
But a good fifteen to twenty percent of people, depending on the month, say they would not have started their company if they didn't encounter some story or some person
on N D Hackers. And if you multiply that by like a hundred and forty thousand
you know, different people who've joined the community forum, like that's that's a very substantial number of companies. A lot of tiny companies and some of them have like gotten bigger.
Gotten acquired. A lot of them are on stripe.
And sort of the way that
Patrick explained to me earlier when I first joined Stripe was like, Hey, it's your job to, you know, get people to start companies. It's our job to have a product that's good enough.
To win them over. You know, I'm not like sitting here trying to like hawk stripe and convert people to stripe like
That's something that Stripe does on its own.
And what was that hundred and forty thousand user number when you were acquired?
Yeah. Let me look it up.
I'm also curious, I'm this is the third time I've done this to you, I'm queuing up two questions. Approximately what percent of indie hackers use Stripe?
as their uh f for their company.
So the second one I d I don't know the answer to.
We don't really have like a process, like we don't measure.
You know, like there's like it's a lot of just
Trust, right? Okay, like we know that Stripe is pretty damn good as a product. Uh comes up on the community forum all the time. I think it was the most referenced company and
all the interviews that I did even before Stripe.
I mean honestly I don't even know what else you would use if you want to take payments on the internet. You could use a ton of other stuff, but they're just like custom services that are white labeling stripe.
Underneath. Like that's what glow is like. Yeah. Like I don't even know if there is another alternative. It's it's a really good product. Yes, David, there are alternatives. Uh it is also a very, very, very good product.
So for me to alternatives worth using. Let's put it that way. So for me to answer your question on exactly how many users there were right when I join Stripe, I have to run like kind of a query. It'll probably take me like
A couple of minutes, so like is it worth it?
On air SQL writing.
Well, do you have any uh mental ballpark award
Like w on the order of a thousand? Ten thousand? It was on the order of like
Mm.
Certain fewer than five thousand, probably more than a few hundred.
All right.
That helps us understand, I think the
the scale and it's been what three and a half years?
Yeah, it's been three and a half years I joined in April twenty seventeen, so
And the actors have been a stripe for much, much longer than it
It existed before Stripe.
That's really cool.
Even just like super ballpark numbers, let's say
Hundred thousand companies.
added since the stripe acquisition, fifteen to twenty percent.
Indie hackers played a major role in that company being started.
Fifteen to twenty
Thousand.
Companies.
Presumably a large portion of them are using stripe, like
That seems like a great
outcome for stripe.
The really interesting thing to me, and now we're in so for people who listen to more acquired episodes, we've been through history and facts a little bit right now, we're in what would have happened otherwise, and and then we we've done a lot of playbook as well, but we can specifically call that out.
You know, if Stripe hadn't acquired indie hackers
It's not like
All the companies.
that have been created wouldn't have used stripe. Like I don't think you influence their any of their decision on what, you know, who who to use for payments. So
What they were really doing is saying like
Man, this thing is really good for our business that it exists. Let's make sure it can thrive as much as possible. It's interesting to me trying to think through the scenario where Stripe didn't acquire indie hackers and the exact same outcome happened for Stripe.
Yeah.
Again, like I don't measure
You know, would you have used Stripe? It's not even my goal really to like make people use Stripe. It's my goal to like make people start companies.
I want people who like would never have started a company because they didn't think it was possible. They hadn't seen anyone like them start a company. They didn't see a path. Like when they hear a story on the Indy Hackers podcast, or when they go on the forum and they see somebody who's like
Like I met a Y C 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
Uh, you know, what's your experience with it? It's like, Oh, I read the story you did with this guy who started this like review site, and I'm like, I'm way smarter than this guy, I can start a company. So I did. Then I got onto YC, and now I don't go to Indy hackers anymore. And like that's that's pretty that's pretty common. Like I meet a lot of people like that. He were just like inspired and like they literally started because they just read that it was possible. And when I think about like me, like
I started my career because like people told me it was possible, you know, and I think spreading those stories helps people get started. And like that's literally all I care about. Like I don't care.
how many of these people end up using Stripe. Like that's the job of Stripe engineers and product managers to like make Stripe the best product.
Alright, so it looked like you were uh you were writing some sequel there in the background while I was pontificating. What'd you come up with? So we've got we had exactly
Fourteen hundred and three users.
on the day that we got acquired by strike.
So we're a hundred X bigger today.
Almost exactly a hundred X bigger. Yeah, almost exactly a hundred X.
Just pretty cool. It's cool to see how that I mean. Wow, that's eerie. There's a lot of stuff to to look into, too. It's like okay, well, how much bigger is the podcast? Like how many more conversations are people having? Because it's not just about having more people, but it's about engaging them more. Uh how many like return visits do people have? And we track a lot of random stuff, but like the number of users straightforwardly
A hundred X bigger in three years.

It's awesome. I mean it's it's a it's a bet on the internet. It's a bet on the internet being able to enable people to create far more companies than they otherwise could have.
Did you see these these stats that came out um last quarter about like new business creation?
Where it's like six hundred people or six hundred thousand people a quarter in the United States were creating businesses like ten years ago. And then last year it was like eight hundred thousand people a quarter. And this year it's like one in a one point six million people.
created a business or filed to start a business in like Q three
twenty twenty.
Which is insane. Like
Like aren't there more and more winner take all opportunities? Like I are we seeing now we're well into playbook, but uh are we seeing basically like a barbellification where the big startups
consolidate to only a few big winners in each market, but then there's like massive, massive opportunity to go after long tail.
Yeah, I think number one, there's a lot of these winner take all startups, but almost all of them create
sort of niche business opportunities for other founders.
And so it's not like this exclusive thing, like oh, they took the Facebook took the social networking market, now there's no business opportunities. Well it's like turns out a ton of media companies get started off the back of that, and a ton of like app companies get started off the back of that. And like there's companies that like teach you how to build a Facebook page and get started off the back of that. So like
I think as an ND hacker, you don't have to worry too much about the winner take all companies. Uh and then we have all these like platforms, you know, YouTube, Substack, OnlyFans, uh arguably, you know, Twitter, where people are just like building audiences and businesses off the back of all those things. And so what's kinda cool is
It's kinda like never gonna be, you know, all the niches are taken, there's no ideas left. And also, I think what people underestimate is just the number of people adopting technology for the first time. Because just because like Zoom exists doesn't mean everybody uses it. Like we've seen very clearly this year, way more people are using Zoom because they've been forced to adopt this thing that they've been kind of ignoring in the past because they just like didn't want to.
And so as more and more people get on the internet and create businesses
And like you use these products, it's more opportunities.
And then like most successful indie hacker businesses sell to other businesses. So it's kinda like the self fulfilling sort of chain reaction where the more businesses there are, the more like products they need.
And so it's kinda cool to see it accelerating and I wouldn't be surprised if that number
you know, in a few years it's like five million Americans a month are creating an online business.
Yeah, that's what I was thinking on. That is like
You know, you've got the platforms.
Like say let's look Stripe or Shopify. Like say and then you've got people that like start Shopify stores or start businesses on the internet and use Stripe.
But then there's this whole other category that I think is like perfect for indie hackers of like
Oh, well, there's actually stuff that you can build
To help
the people that are using Shopify that are using Stripe that like, you know, there's so many businesses that have been started around Shopify that are like and and Stripe too, that are like not a business on Shopify.
They are a business that provides us a a custom set of tools for a certain set of users.
that need like hobby businesses. Like you're a hobby game store and you are both buying and selling from your customers. Like your customers come and they trade in stuff. Like you can run on Shopify. Great.
But like you also need some custom functionality to buy stuff from your customers.
Boom. Business. And I think like a lot of the smarter like founders are figuring out ways to kind of escape the competition because it's like okay, you can build like a Shopify plugin, but there's like a lot of other Shopify plugins. So it's a cool opportunity, but then you get kind of crowded out.
Like I I'm talking to a uh a guy tomorrow, his name's Jordan O'Connor.
He's got like a really cool story where he's like
you know, a father, a husband, he had a full time job, and he would like eke out time every morning to kind of work on his business because he knew that like
after like eight AM, his son is gonna be awake and he's gonna have no time at all to do anything.
And so what he ended up doing was kind of escaping the competition
And he built a bot for this app called Poshmark.
Which is huge. Like a lot of people buy and sell like their used clothing on Poshmark, but they don't have a marketplace. Like they have no like they don't even have an official API. So he just sort of like reverse engineered things. He's like, there's not gonna be any competition here, but it's kind of the same playbook, like build, you know, for this an ancillary tool for this bigger platform.
And he built like kind of a bot that helps you like do well on Poshmark.
And I think he got to like twenty grand a month. And now he's just kinda like he quit his job. He's just kind of set. And he's just like doing other fun projects now that like
you know, interest him from year to year while that bot just kinda makes money for him in the background.
Magic of software. It's pretty crazy.
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All right, well I'm gonna start bringing us home here.
Cortland, answer this question however you see fit, but how would you grade the indie hacker's acquisition by Stripe in terms of was that a good use of capital and resources for Stripe?
Oh, A plus. I think it's uh I'm slightly biased here. Yeah. Like Stripe is a company, as you may know, that has uh lots and lots of money on the Indyactors acquisition. Did not cost billions of dollars. I think it's generated only
goodwill towards Stripe, more customers, more users towards Stripe, and I think it's done well for literally everybody involved. I think Stripe's happy to have it. I'm happy to be a part of Stripe, and I think
For the people who use indie hackers, they're very concerned early on. You know, they're very worried.
And I don't think I've met a single person who said like they aren't happy that it happened. So it's hard to imagine it having gone better.
Yeah.
Should more people do this?
I mean the way that I'm sort of categorizing this in my head is
they made an investment to ensure the continuity of this thing that was creating new customers for them. And like, do other companies do that? Should other more companies do that?
I think they should be a lot more creative and imaginative. I think like there's like as humans we have this impulse to just like
Just like mess with things. It's really hard to buy something.
And then not touch it. You know, it's really hard to do that. And I think when people think about like, Okay, if I buy this, like what am I gonna do with it? They think, Oh, it's gonna be like so much work, have to do this, have to do that, and they don't like make these acquisitions, whereas I think it's striped they're very much like no, Courtland's doing a good job.
And we don't have to do anything.
And like if we can just ensure that it keeps going, like you said, like that's a huge win by itself.
But there's other wins too. You know, I think one of the the trends we're gonna see going forward is like
tech companies basically owning like
Some kind of media company.
Which I think is super powerful because like media companies are what connects
with actual people on the ground.
And in a way, like Andy Hackers is still very much a media company. Like I still spend a lot of time on the podcast.
Spent a lot of time in our newsletter.
but out a ton of content and we're sort of like becoming a platform almost like Substack ask.
Or enabling other people to sort of build newsletters.
and grow their audiences on indie hackers. So I think like even without just like having indie hackers continue to exist, and even without it like driving excess
additional customers to stripe.
It's just a good way for Stripe to be able to communicate in the future if it wants to, you know, we're launching this thing or like, you know, we're we think this about the world.
And like now they have a place that's not just hacker news or Twitter to do that.
Has Stripe done any?
Anything else like this since you've been bought? Or
Yeah, Stripe has
A magazine.
Called Increment Magazine.
Uh just increment.com. It's kinda like the best sort of magazine.
for all sorts of basically work that gets done. So they've done like issues on like software engineering and APIs and the cloud and being on call
And like people love this magazine. It's really well produced. It was created by kind of initially Susan Fowler.
Who's the engineer who kinda blew the whistle?
on Uber back in the day. Now she works, I think, at the New York Times.
Uh so that's like a a really cool
like Stripe Project that I don't think it's enough press and attention. There's also like Stripe Press, which is kind of like an in house thing. It wasn't like exactly acquired.
But all these sort of initiatives.
I think, you know, involve often people who are like come in from outside the company and help.
They're all like kinda moonshots. You know, I put it in a very similar category to endy hackers, even though it's like
you know, different. But it's something that most companies like wouldn't do. But like Stripe kind of trust, like, okay, well what if we put out like these books
uh that like help people become better founders, make better decisions, and start more companies. It's hard to measure like how many people actually read this book and made a decision because of it. But like we can kinda trust that like
they well do that.'Cause like we know that's how inspiration works.
And like it'll increase stripes bottom line.
Yeah.
Makes total sense.
For acquired listeners,'cause I know we're releasing this in in both feeds, where can people find you? What should they check out first of of the various indie hackers and Cortland properties?
Yeah, I mean the easiest way to really get into Indy hackers is the podcast. So if you just go to
Your podcast player and search for N D hackers, it will come right up top for you.
Uh check out any of the episodes. They're all pretty good. They're all different stories of founders and how they've succeeded. And so I just recommend listening to a few of them.
And really absorbing like, you know, what is this path like?
How can you start off maybe as an ND hacker and then eventually grow to to uh start a much bigger company? I've I've interviewed like lots of founders of like Y C funded companies and V C funded companies, but also tiny and hackers who don't want to grow anymore. So check out the podcast.
And you can find me on Twitter.
At C S Allen.
Awesome.
Well listeners
We hope you have a happy holidays. It has been one of the best parts of our twenty twenty being with you all.
And we will see you next time.
We will see you.
Next year.
Can I not wait for twenty twenty one. But seriously, like
The best part of twenty twenty.
Hanging out with you all.
Virtually.
It's been a great year.
The world aside. It's been a great year for acquired in the community.
Can't wait for next year.
See you in twenty twenty one, everyone.