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. They want those companies to succeed and make a whole bunch of money because then Stripe makes money. So there's really like perfect alignment. There's no need for Stripe to tell me what to do, or force me to do things that I don't want and vice versa. I'm not really pushing against the Stripe mothership in any way.

James: Do you have any sort of side projects you want to work on or the urge to do indie hacking outside of working on Indie Hackers and for Stripe?

Courtland: Every day I wake up, it's like, well, what am I going to work on today? Am I going to build out a network of podcasts? Am I going to create like a milestones leaderboard that's similar to Product Hunt, but for indie hackers. Am I going to create like a groups interface so indie hackers can create their own communities? And so I already feel like I have a ton of side projects.

James: Let's move on a little bit to indie hacking in general and what advice you can give to current indie hackers. How about those that are at the start of their journey with indie hacking. where should they start?

Courtland: Those are the best indie hackers. In fact, that's most indie hackers. Most people don't know what to work on and they're not sure what to start. And I think the first thing you should do is probably ask yourself what it is you want in the first place.

Like, why do you want to be an indie hacker? Who inspired you? What do you want to accomplish?

Usually, the answer is some form of freedom, but there's lots of different forms of freedom. Do you want the creative freedom to work on whatever you want? Do you want to work from wherever you want? Like how much money do you need to make?

These are all really important questions because I think if you set out to do something without knowing what your goals are and knowing what would help you feel accomplished, then when you eventually hit that goal, it doesn't feel that great because you don't even realize that you hit it and you don't know if you should keep going, you should change directions, et cetera.

So, I always advise people to start off by just like spending an hour or two, just asking yourself what you want, who you are, what kinds of things make you happy in life?

I just think it's really important to know who you are and what's gonna make you happy. Second. I think you've gotta avoid the common pitfalls of idea generation. For example, we all think that starting a company is like having an invention, right?

A real business idea, I think should start. Always from the problem, not from the solution.

People are driven to take actions in the world because they're trying to fulfil their desires because they're trying to solve problems. And if you want people to take action in the direction of the thing that you built, you need to understand their desires and their problems and make sure that the thing that you build solves that.

But if you're trying to come up with an idea, I would say, just get obsessed with the problem and don't fall into the trap of thinking that it needs to be some problem that no one's ever solved before.

James: Yeah, I think it was absolutely sound advice. A lot of indie hackers are solo founders and sometimes it can be isolating when you're a one person team working away in your business. What's your advice about getting stuff done and staying motivated as a one person team?

Courtland: Even though, like I started Indie Hackers as a one person team. Right before I joined Stripe, I brought in my brother to work with me and we talked to each other on the phone every day. I'm a huge fan of social accountability.

We're social creatures. We care a lot about what other people think about us. We don't want to let down our coworkers. We don't want to let down our colleagues. So I think as a founder when you've gone from probably working a job your whole life to suddenly being on your own, and you don't have a boss, you don't have coworkers, you don't have anybody who expects anything and no one even knows what's on your to do list, it can be a bit jarring. And you might think, oh, what I need to do is figure out all these different productivity hacks to really push myself to work harder, but I think, the ultimate productivity hack is just have someone that you're accountable to.

Have a mentor, a partner, a co-founder. It could be your customers. Early on with Indie Hackers I just resolved that every week I was going to send an email to my mailing list and it was going to have a section right at the top where I said; this is what I did this week and here's what I'm going to get done next week.

I can't skip out on it. I can't let this other person down.

James: Yeah, that's something that I've personally found really useful. We're seeing a lot more communities pop up, especially paid communities. And there was a post on Indie Hackers about trends that are coming up, and got a great answer or some thoughts about communities and why they're becoming more and more popular now. Why is it you think that?

Courtland: I think communities are the future. Being social is one of the main things that we do as human beings, we care about being parts of communities. We care about relating to others.

If you look at the 2010s, we always had these huge social networks. We had Twitter, we have Facebook and those are great in their own way, but there's a lot of problems with them that I'm sure everybody can enumerate. And so we're starting to see communities unbundle these huge social networks. We're starting to see people create more niche, interest based or personality based communities around certain topics.

Besides that, I think there's just a flywheel effect that's accelerating things. You have more and more people joining these communities who are realizing that they want some sort of social connection with people online, especially with COVID-19 and everybody stuck at home.

I think that gives people creating communities more incentive to create them. Because now, "Hey, my community is going to grow". There's so many people who want online community, like maybe I should start this. Maybe it's a good business model for me. Maybe it's like a fun way for me to connect or learn from other people.

And then once people start creating more communities and you have other companies that create tools that make it easier to create communities. Cause it's kinda like selling shovels to people during a gold rush, right? Whenever people were doing something you want to make tools for those people and help them do it better.

So there's been an absolute explosion in the past year of people creating community building websites, community building tools, community building blog posts, community building podcasts. And all of that in turn makes it way easier to build a community. So now the whole flywheel repeats, more people build communities, more people join communities, more people build tools for communities, et cetera.

James: We've also seen a growth in newsletters and paid newsletters. Why have we seen that?

Courtland: I think when it comes to newsletters and writing and especially podcasting, I put them all in one bucket. A lot of them are cults of personality. A lot of them are people realizing that they don't necessarily want to read the mainstream news.

And I think this has been true on the internet for quite some time, but I think that the growth of social media has really allowed people who have been writing on their own blogs and writing on their own newsletters to distribute what they've been doing to a wider audience. And then the growth of tools like Stripe and Patreon and just the acceptance of people making online payments has led these creators to realize; "okay, I can charge money for this".

I think we're at an inflection point where people are tremendously inspired by seeing some of the numbers that a few individuals have been putting up. You start to think;

" Hey, maybe I should have a blog where I write about tech topics three or four days a week and see what I can do."

It's just this formula of inspiration, which I think about a lot at indie hackers, which is, you show a story of someone doing something just amazing and making a ton of money, something that people can relate to you, they can imagine how it would change their lives. Then you break down how they're doing it and you make it approachable, and you talk about the person's background and you show how they're approachable too.

In other words, you relay the message. Hey, you could do this too. And that's like the trifecta formula for inspiring people to do things.

James: Why is it that indie hackers are so open with sharing numbers? What's the benefit of that?

Courtland: I think it's just a, consequence of the infinite distribution provided by the internet. Anyone can put up any sort of website, whether it's true, whether it's fake news, whether it's credible or whether it's good, whether it's bad. If you write something that engages people and you figure it out, how to distribute it, then you can get the eyeballs.

It means that there's just more information out there for people to learn from, if you go to indiehackers.com/interviews, there's like 500 stories there where people say:

Here's how I came up with my idea. Here's exactly how much money I'm making today. Here's what I was thinking I wrote the first few lines of code. It's an immensely useful resource for learning how to do things cause everybody's so transparent. And then when you go out there, you want to pay it forward because you learn from all these transparent people and so you're more likely to be transparent yourself.

James: Yeah, absolutely. And you mentioned that you've got over 500 interviews on the site you're 173 episodes of the podcast - you speak to a lot of indie hackers. What is your view on the current state of bootstrapping, where there are so many people now starting businesses and seeing this as an opportunity where they've got a little bit extra time?

Courtland: Yeah, I think Indie Hackers is bigger than ever. You mentioned bootstrapping in particular, it's funny, I've seen the erosion of the line between bootstrapping and fundraising in the last four or five years. People, when I started Indie Hackers were so religious and dogmatic about bootstrapping, and I kind of was too. But now we're seeing more investors who are figuring out models that allow them to fund these smaller indie hacker type projects and still make a return on their investment.

If you're an indie hacker and now there are options where you don't even have to quit your job or take a leap or, work on the side of your job and you can actually just get some funding. That's just another force that's gonna spur people to start more and more businesses.

James: Definitely. Courtland, we'll end on a few quick fire questions.

First of all, who's an indie hacker you admire or who should people follow?

Courtland: Lynne Tye. One of my best friends is just absolutely crushing it with her website, Key Values. Rosie Sherry, obviously. She's one of the first people that I interviewed for Indie Hackers. But it's hard to pick like a favorite indie hacker.

James: What about your favorite book for indie hackers to read?

Courtland: uh, the books that have helped me the most are books, like Thinking Fast and Slow. Sapiens. And then maybe particularly for indie hackers, there's a book called Hooked, which talks all about habit formation and what goes into the products and devices and apps and websites that allow us to form habits that we have positive associations within our life.

So I think that's a really good book and it's really influenced my thinking and how I build Indie Hackers.

James: A great list of books. What about podcasts?

Courtland: My favorite podcast is. Conversations with Tyler, which has nothing to do with indie hackers. But again, I think it's good to listen broadly. I've recently become a big fan of the Indie Bites podcast with James McKinven. But there's just such a growing and vibrant ecosystem of podcasts out there. It's hard to pick a favorite.

James: Some more great options. And then finally, what are you most excited about for the future? Both in personal life and business. I know you're on a trip away from San Francisco at the moment.

Courtland: Yeah, I'm really excited about just getting older. A lot of people hate getting older, but I've recently become more at peace with it. My friend said:

"Getting older as a privileged, denied to many" and looking at it through that lens. I think I've really just appreciated getting older and wiser and calmer.

James: Awesome. Courtland again, thank you so much for coming on fantastic as ever.

Courtland: Thanks, James.

James: Thank you so much for listening to this episode of Indie Bites. I hope you feel as inspired as I do after listening to this conversation with Courtland.

If you'd like to hear more, there's actually a 45 minute extended version of this episode available to my mailing list subscribers. So if you'd like to listen head over to indiebites.co pop your email into the subscribe field, and I'll send you the extended conversation.

If you find this episode useful what i'd love you to share it with just one other indie hacker that will also find it useful. It really does help the podcast grow.

As always you'll find links to everything we discussed in the show notes. That's all from me. Enjoy the rest of your day.