The Challenges and Benefits of Building an Indie Hacker's Business

Courtland Allen founded Indie Hackers in 2016, grew the business $8k MRR with sponsors, and then sold to Stripe 9 months later. An inspirational story that doesn't end there. Courtland has now been working from within Stripe for the past 4 years, where he continues to build on the platform and produce the excellent Indie Hackers podcast. He's a fountain of knowledge and I think you'll love this episode.

What we covered in this episode:

On Indie Hackers:

• Why did Courtland start IH?
• What is an 'indie hacker'?
• What are the pros and cons of building within Stripe?
• Does he have goals for IH set by Stripe?
• Does he have any other side projects, aside from IH?

On indie hacking:

• Where should new indie hackers start?
• How do you stay motivated as a one-person team?
• The growth of communities
• The growth of paid newsletters
• The current state of bootstrapping

Quick fire

• Favourite indie hackers are; Lynne Tye, Rosie Sherry, Amy Hoy, Natalie Nagele.
• Best book for indie hackers; Thinking, Fast and Slow, Sapiens, Hooked.
• Favourite podcast; Conversations with Tyler.

Follow Courtland

• Twitter

Follow Me

• Twitter
• Indie Bites Twitter
• Personal Website

Thanks to Weekend Club for sponsoring Indie Bites.

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Full Transcript

James: Courtland has inspired so many of us to build our profitable internet businesses. Let's talk to him to find out what's important as an indie hacker in 2020. Courtland, welcome to the podcast. How are you?

Courtland: Excellent James. Thanks for having me.

James:  To set the scene and for those that might not know, tell me a little bit more about what Indie Hackers is and why you started the website?

Courtland: Yeah. So I moved to the Bay Area when I was like 23. I wanted to start a very stereotypical high growth tech startup. I wanted to be a unicorn company. I wanted to make billions and be world famous. After seven or so years of that struggle, I was just tired of it. I got tired of the VC funded software world.

And so I took time off work. I was doing a lot of contract development and I just started searching for other examples of people who've done the same thing. And it turns out there wasn't really a good way to learn how to do this. Everybody online was doing the same thing I was doing; just like looking for comments left by Pieter Levels or like tweets where some people would share some tidbit of their story, but like we couldn't find anything great. And so I kind of just solved my own problem and said, you know, I should build the thing that helps people do this. I was surprised it didn't exist. And here we are 4 years later, somewhat ironically, I decided that I wanted to be a bootstrapper. I decided that I wanted to get out of the high growth startup game.

And within a year, starting Indie Hackers, it was acquired by Stripe and fulfilled one of the goals of a lot of people in the high growth startup game want to. So that's how we got to where we are today.

James:  What is your definition of an indie hacker?

Courtland: I think Tyler Tringas actually put it well recently. He said that "the new American dream is to build a profitable, sustainable, remote software business that you can run from home ". You can run from wherever you want work with wherever you want, that scales nicely, and that prints money for you. And I think an indie hacker is somebody who's trying to achieve that. Someone who doesn't like the status quo, someone who doesn't want to work for the man for the rest of their life.

There's no problem with doing that. I think jobs provide a lot of stability for people, a lot of predictability, but if you're like me, you just don't want to have a boss. You don't want there to be a cap on your salary. You don't want somebody else telling you what to work on. You want to control your own life and you're an indie hacker.

James:  What are the challenges and benefits of building Indie Hackers from within Stripe?

Courtland: I don't have to get on the phone with advertisers anymore. Indie Hackers makes $0. It's a hundred percent just me focusing on making the community good and helping it grow. I think probably the one challenge is that I'm someone who puts a lot of pressure on my shoulders to, I think, perform well for others. And at Stripe, Patrick Collison is my boss. He went out on a limb and acquired Indie Hackers, and I feel a lot of pressure to make sure that any hackers, is a success.

And at Stripe, like I'm extremely autonomous.  I talk to Patrick and the team there once every three months, once every six months, sometimes,  and it's almost always just check-ins; how are you doing? Do you need anything? What can we help with et cetera? It's like the ideal working situation. I can't imagine having a job under any other kind of framework.

James: Are you tied to any goals within  Stripe? Do they set any targets for you that you have to reach, such as traffic numbers or engagement? 

Courtland: There isn't any sort of like you have to reach X number or the axe will fall. I think what's cool about the fact that I joined Stripe is that my goals are very much aligned with theirs. And I think if you ever work with any sort of partner or you acquire anyone or you get acquired, you should always try to make sure your goals are aligned because if there's even a one degree difference between where you want to go and where they go, at first that's very small, but after a number of years, that gap has widened into something that's like very hard to fix.

 And so I just want Indie Hackers to be like as big and as meaningful and useful as possible. I think about that religiously every single day. And that's what Stripe wants to ultimately they want more people starting companies...