Your Whole Goal Is to Not Quit - Courtland Allen of Indie Hackers

by Y Combinator9/22/2017

Courtland Allen is the founder of Indie Hackers, a place where the founders of profitable businesses and side projects can share their stories transparently, and where entrepreneurs can come to read and learn from those examples.

Check out the Indie Hackers podcast here.


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Craig Cannon [00:00:00] – Hey this is Craig Cannon and you’re listening to Y Combinator’s podcast. Today’s episode is with Courtland Allen. He is the founder of Indie Hackers which is now part of Stripe. And for those of you who don’t know it Indie Hackers is a place where the founders of profitable businesses and side projects go to share their stories. Courtland also hosts the Indie Hackers podcast and you can check that out at Two quick announcements before we get going. The first to which is YC is on a fall tour right now and all the locations and dates are at And the second is YC applications for the 2018 batch are open and that link is Alright, here we go. Why did you decide to start doing a podcast after the site was going?

Courtland Allen [00:00:44] – People were asking for it. It seemed, it seemed like a good idea. I mean the number of people who asked me to do a podcast it was so much higher than people asked for any other feature. A part of the text interviews was that you have to show your revenue. Everyone is completely transparent. The number of people that I reached out to we thought would have really good stories for the site that people can learn from, who were willing to share everything but their revenue was pretty high. I kept getting tired of people saying, “You now I’m not going to come on if I have to share my revenue. You need some other way where I can come on and share my story,” so the podcast helped me kill that bird. And also it appeased people who wanted me to do a podcast, but I was terrified of it. Because like I said earlier I’d never done a podcast.

Craig Cannon [00:01:28] – Were there people you admired at the time? You’re like, “Oh I want to make a podcast like x, y, or z.”

Courtland Allen [00:01:32] – No, not at all. I had barely listened to podcasts.

Craig Cannon [00:01:35] – You weren’t even in.

Courtland Allen [00:01:36] – Yeah, I mean I was just like, “You know what? I’ll try this.” I had a very lazy approach to it. I’m not going to do a ton of research. I’m just going to try talking to people and see how it comes out and have my own style. I think it’s worked out. I’ve gotten better over time.

Craig Cannon [00:01:49] – Yeah. Well what are the skills you’ve developed you think?

Courtland Allen [00:01:52] – I think I’ve gotten a lot better at preparing efficiently.

Craig Cannon [00:01:57] – You mean what like reading..?

Courtland Allen [00:01:59] – Knowing what to read and what to listen to, what kind of questions to ask that’ll be engaging and that they’ll give good answers to. How to follow up on a question if you get an unexpected answer. I’m kind of a control freak, I’m like, “Okay, here’s exactly what’s in the beginning. You know I’m going to ask question a, b, c, d, e, f and this is how it’s going to go.” and you know you ask a question and they start giving you answers all over the map and suddenly your perfect plan is thrown into disarray. Just having the composure and the ability to calm down and be like, “Okay, it’s okay.” Just listening to what they’re saying and have a normal conversation was difficult at first. Other things, like I don’t know of you’d call this a skill, but just being comfortable in my own skin. Not cringing at the sound of my own voice.

Craig Cannon [00:02:38] – ‘Cause you edit your own podcast?

Courtland Allen [00:02:39] – Yeah I edit my own podcast. But I would go back and listen. If you hate the sound of your voice…

Craig Cannon [00:02:44] – Yeah, I know the feeling.

Courtland Allen [00:02:44] – But I hated the sound of my voice at first. Now I’m fine with it, but at first I was like, “Man I sound awful, like who’s going to listen to me?” Now it’s not a problem.

Craig Cannon [00:02:50] – Yeah you can only spend so much of your time cringing at yourself after you’re like, “Oh god.” I mean like the amount of hours I’ve seen myself on video and listened to myself on a podcast, whatever. It’s fine. That is one of the things that I thought the fear would remain and it completely goes away. Maybe to a fault. We don’t care. But yeah, the video element has thrown a few people. What was your favorite episode? I haven’t listened to all of them yet.

Courtland Allen [00:03:20] – It’s hard to say if–

Craig Cannon [00:03:21] – Top two.

Courtland Allen [00:03:21] – I’m always like, “I’m going to hurt somebody’s feelings.”

Craig Cannon [00:03:24] – Okay.

Courtland Allen [00:03:24] – And then I forget, too. You know, “Like what happened in that episode?” But some of the coolest ones, I did one with my friend, Julian Shapiro, who’s got a growth consultancy called Bell Curve. And he just like deep dive into like a bunch of different kind of stories of him working with different clients. And he was not afraid to share like times when he just messed up. I thought that was really cool.. I really like the episode I did last week with Wes Boss.

Craig Cannon [00:03:46] – That was a good one.

Courtland Allen [00:03:47] – Yeah, he’s a great guy, I mean he’s, gets an enormous amount of work done to be just a one person. He’s got an email list it’s like 170,000 developers on it that he’s built by himself in like five or six years. A Twitter following of like 100,000 people and he’s just trucking along, he works nine to five, puts his laptop down and then goes to hang out with his wife and his kids. Hhe’s got it together really.

Craig Cannon [00:04:08] – I wondered about that, like is there a list of people that you admire? Like, “Man, that person has it figured out. I want to do exactly what they’re doing.”

Courtland Allen [00:04:18] – Yeah, there’s a lot of people and I always forget I’m like, “Man that person’s got it figured out,” and the next week I’ve totally forgotten about it, moved onto other things. I’m like, “Oh yeah! Wes Boss guy.”

Craig Cannon [00:04:26] – You’re life’s pretty good.

Courtland Allen [00:04:27] – Yeah, it’s okay.

Craig Cannon [00:04:28] – I’ve seen a handful of round-ups of Indie Hacker pro tips from every episode. Are you continuously integrating their great ideas into your daily life? Or do you kind of just go your own way?

Courtland Allen [00:04:44] – It’s funny it’s one of the things I was telling a friend a couple of days ago, I think generally speaking like all of us tend to over weight like novel advice, things that are new or flashy or we haven’t heard before. It’s like so easy to ignore the things that we hear all the time. You know like, “Make something people want.” Or, “Talk to your customers.”

Craig Cannon [00:05:03] – Exercise.

Courtland Allen [00:05:05] – Yeah, yeah, exercise you know, take some time off. “I’ve heard that before I get it.” But I try to have the discipline to when I see that kind of repeated advice to take it to heart and not look at it as something that, “Okay have I heard this before? Yes, does it matter?” As a reminder to myself like, “Am I actually living by this?” You know I internalize, so I like to think I have like, “Am I actually talking to my customers? Am I actually taking time off? Am I actually exercising?” And the answer a lot of the times is no. I think when people do like these round ups and people analyze things and I see this advice repeated I take the time to ask myself if I’m doing it. And you know I think I’ve gotten better at it, just repeated reminders to myself.

Craig Cannon [00:05:45] – Yeah, I think you become conscious of it. But I agree, I don’t need 12 new morning routines in my life. Alright, so we posted a bunch of questiond, or other people posted questions to Twitter for you. You have a lot of fans online. Ryan Hoover, Product Hunt asked, “What do you believe that most others do not?”

Courtland Allen [00:06:05] – It’s a tricky question.

Craig Cannon [00:06:05] – Have you prepared this one? Yeah.

Courtland Allen [00:06:06] – I’m glad I got this question on Twitter, rather than just being asked randomly, ’cause it’s hard to answer unless you’ve thought about it. Kind of a funny story, I think this question originally comes from Peter Thiel who would ask the founders of companies that he was interested in investing in, just as a way to find out if what they’re doing is truly unique and whether they’d be able to have a monopoly and very few competitors. And that’s why he liked it. I liked it when I heard it because it’s kind of a sneaky way to get somebody to say something controversial. When I was in YC five years ago I asked Paul Graham. I think 2011, I was like, “Hey PG, what do you believe?” I think I asked, “What do you believe that other smart people don’t?” And it took him a long time to answer. He was just like, “I don’t know my thoughts, they’re not indexed that way.” But then he ended up coming up with an answer and it worked, it was controversial. I don’t think very many people would agree. I can’t say what it was, out of respect for him.

Craig Cannon [00:06:54] – Okay.

Courtland Allen [00:06:55] – And I don’t mean to be a tease, but luckily I’ve had some time to think about it. Probably the most obvious one is I think that it’s probably a bad bet to start a VC funded company for the vast majority of people. You should not go that route. But there’s other things that I believe, too. I think that, in the value of kind of this culture of always talking about, you know like what mission drives you and we kind of are not honest about the fact that a lot of us are motivated by money and financial things. I think it’s probably better for the world if people can just be up front and honest about that. I’ve got a few others, but let’s start with those two.

Craig Cannon [00:07:30] – Yeah. No, I completely agree. Everyone’s ability to rationalize is unbelievably powerful.

Courtland Allen [00:07:37] – Yeah!

Craig Cannon [00:07:38] – And you can be into anything and if you’re good at it, like just being good at the game is often enough to drive people. So you see like folks criticizing anyone who works in anything. And they’re like, “Oh why do they care about this? Why do thy do that?” Well like, ’cause they’re really good at it.

Courtland Allen [00:07:53] – Yeah!

Craig Cannon [00:07:53] – And they’re into it.

Courtland Allen [00:07:55] – It’s fun to do things that you’re good at. It stimulates your brain.

Craig Cannon [00:07:57] – Yeah, absolutely. Was there a point at which you kind of turned on the interests in VC backed companies? Did something happen?

Courtland Allen [00:08:07] – It was before I even got into YC, funnily enough. I went to Startup School 2009 and Jason Fried was there from 37signals as they called it at the time. He stood out like a sore thumb. He was completely different than everybody else who talked. Everybody else was kind of a VC, or they were a founder of a VC backed company. And he got on stage and basically said, “Everybody else’s lying to you, don’t believe a word they say.” A credit to YC for inviting the opposite opinion there. I was very taken by what he had to say because no one else was saying it at the time. It didn’t really change my approach at that time, then I got into YC and we had the weekly Tuesday dinners, where founders would come in. The same thing happened. We had a lot of VCs come in, we had a lot of founders of well funded companies come in. And then Kevin Hale came in from Wufoo. And he was the only person, he was kind of an Indie Hacker at the time. He was just like, “Yeah. I packed up my company, we moved to Florida. Investors call us every day. We just politely say no. And we’re just happy making money.” You know they’re making millions of dollars a year. I was intrigued by that, “Huh.” But it wasn’t until recently, basically last year I really decided that’s what I wanted to do for myself.

Craig Cannon [00:09:11] – Yeah.

Courtland Allen [00:09:11] – But I wasn’t really, in the mood or really inclined to do the whole fund raising thing and I’d rather just make money from an idea online that I enjoy doing.

Craig Cannon [00:09:21] – And that idea, was that Indie Hackers?

Courtland Allen [00:09:25] – Yeah.

Craig Cannon [00:09:25] – Or was that, okay.

Courtland Allen [00:09:26] – The company that I did YC with, the Taskforce, it’s still exists, it’s still out there. It still actually makes money, passively. I kind of worked on that for a little bit, but I didn’t think it was really going to go anywhere, I wasn’t enthused about the idea. And so I sat around for like a couple days thinking, “Okay what am I going to work on?” And, PG wrote us…

Craig Cannon [00:09:44] – Must have been two days.

Courtland Allen [00:09:47] – It was like three solid days.

Craig Cannon [00:09:48] – Okay.

Courtland Allen [00:09:48] – PG wrote about this like 12 years ago or something. A lot of people when they come to the idea phase they think that it’s something that you naturally have to be good at. You know you just get a good idea or you don’t, right. Whereas the reality is it’s like any other creative endeavor. If you practice for long enough you’ll create a good idea, you know you don’t try to like paint the Mona Lisa in like 15 minutes and if you don’t get it you give up. So I was like, “All right, I’m going to push through this. I’m going to spend like two days coming up with ideas.” Most of the were absolutely horrible. You know I just deleted them immediately. But by the end of two days I realized I was consistently coming up with like much better ideas than I had before. And I was just reading through Hacker News threads. ‘Cause people would ask like every month. Ask HN, “What’s you’re profitable side project?” Or Ask HN, “How much money are you making from your business?” And people would share all the details, so I figured, “Okay there’s like hundreds of stories here. If I read through enough of them maybe I’ll glean some insights, I’ll see some patterns that I can apply that’ll help me come up with an idea.” And that’s literally exactly what happened. I mean the idea for Indie Hackers was based off of the realization that, “Hey I’m not the only person who’s researching all this stuff.” The reason these threads are so popular is because everybody else is really interested. I could probably do a better version of these threads. And that’s what Indie Hackers is.

Craig Cannon [00:10:53] – I was wondering is it because there’s been a rise in the popularity if Indie Hackers, right. But I think there’s also a rise in just the number of those threads all over the internet.

Courtland Allen [00:11:03] – Yeah.

Craig Cannon [00:11:03] – Is that because more people are now thinking about small business or just non VC backed businesses or there’s more people in the software development space right now?

Courtland Allen [00:11:14] – I think it, probably a combination. I read the book Sapiens earlier this year, it’s kind of a history of all of humanity from the beginning of evolution. And my takeaway from Sapiens was that human societies tell stories. And it’s tricky because it’s difficult to determine whether or not something you believe is just like an arbitrary story that your society happens to tell, or if it’s like some immutable fact of the universe. And for the longest time like the story around tech companies has been that if you start a tech company you have to raise a lot of money and prioritize growth over funding. You know that’s the story. And so it’s amazing how much everyone just believes that and doesn’t even consider the possibility that you can start a profitable company that doesn’t have to be that big. And you don’t need any sort of investors or gatekeepers to tell you what to do. The story has started to change a lot. And once people hear this alternative version of the story and once they see examples of it, people will kind of wake up out this zombie like state and like, “Oh I guess I can do that.” You know they’ve sort of been given permission. But there are other practical factors and reasons why the story has changed. A good one if I look at the Indie Hackers traffic stats something like 60% of the traffic is from not in the United States, let alone Silicon Valley. People are all over the world starting these companies. And it just from a practical standpoint it’s hard to raise money if you live in like Bucharest. You know it’s difficult. You don’t live in Silicon Valley you don’t have access to investors and so your options are either you suck it up and try to raise money locally, you move to a tech hub and raise money there or you just prioritize profitability. Which is kind of like the easiest of those three options. There’s a lot of natural pressure, as more people over the world get interested in tech to start profitable businesses and to care less about growth over all else.

Craig Cannon [00:12:55] – Have you seen that there’s, there’s a common trend in folks just getting started, starting similar kinds of software businesses?

Courtland Allen [00:13:03] – Yeah, for sure. The other thing is like if you look at the companies that VC tend to invest in they’re generally in winner take all markets. ‘Cause venture capitalists want a massive return, you really want to be number one. You want to destroy the competition. It’s a social thing like Facebook or search applications like Google, versus things that are profitable. Like you don’t want to be in a winner take all market right, you don’t want to be fighting for your life every second of the day. And you don’t want to be, you know in a zero sum game where everyone else has to lose for you to win. And so people end up starting businesses that are very related. How many profitable analytics companies do you know? Like email marketing companies, there’s a ton!

Craig Cannon [00:13:37] – Mm-hm.

Courtland Allen [00:13:38] – You know how many different ways are there to teach somebody something? I tell people all the time if you want to start a business, just teach people. People like learning in like a thousand different ways. Right, some people want to go to college, some people want a like, you know classroom settings, some people want to read, some people want video courses. Some people want email newsletters. Some people want to learn through games. There’s no reason why you have to, you know,

Craig Cannon [00:13:56] – Right.

Courtland Allen [00:13:57] – completely differentiate from everyone in the market. You can do something that’s similar and people will like your own unique style. So people for sure start related businesses and I think it’s a good thing because then it, it kind of fosters a sense of camaraderie. You don’t have to compete with everybody, you don’t have to be mistrustful of everybody. And you can get advice from people who are similar and doing things that, kind of tread that path before you.

Craig Cannon [00:14:18] – Well I’ve been wondering that with all the guests you get. Because they’re divulging most of their information.

Courtland Allen [00:14:23] – Yeah.

Craig Cannon [00:14:24] – Usually how much money they’re making, all these kind of metrics. Are they worried about copycats? Or is this something now that you have some traction they kind of like know the deal and it’s easier to get people?

Courtland Allen [00:14:35] – Yeah, I mean people that I’ve talked to are generally not that worried. I’ve had some people who refuse to come on because they say, “What’s the benefit of me revealing my secrets? You know someone going to copy me?”

Craig Cannon [00:14:43] – Yeah.

Courtland Allen [00:14:44] – And then I’ve had people who revealed their secrets that have actually been copied and it’s always hilarious. If you think about the kind of person out there who’s going to like just listen to your podcast and read your interview and just waiting for someone to reveal all the details. And then they clone everything that you’ve done and make some crappy version of your website. But that’s different and no way at all, except that it’s two years later. That’s not the most competent person that you should you be afraid of. Generally it’s a nonissue. Especially if you’re not in some sort of winner take all market.

Craig Cannon [00:15:14] – Even more questions from Twitter. There is a David Otomoo asked this question to both you and Ryan, which is part of the YC application. It is, “Tell us about a time you successfully hacked a non-computer system to your advantage.”

Courtland Allen [00:15:30] – I do remember doing this in the YC application. My answer now I think would be more interesting if I related it to Indie Hackers. Early on in Indie Hackers history I was kind of running myself ragged. I really wanted to put out a lot of content. I wanted to do three or four or five early on, interviews per week. And these are not small interviews. Sometimes a thousand, two thousand words. Sometimes very poorly written, I have to edit, I have to follow up with the person. So they took hours and hours.

Craig Cannon [00:15:57] – You did this solo.

Courtland Allen [00:15:58] – Yeah I did it solo. And I was sending a newsletter and I was trying to grow the business as well and so my trick early on was, “I’m just going to work 80 hours a week.” It was not much of a trick. Yeah, but eventually I realized like, “Okay, this is not going to work.” It’s okay to do things that don’t scale, but you can’t do that forever. You have to figure out a way to make it work. And so what I wanted to do is increase or at least maintain a level, like the quantity of content that I was putting out without having a drop in quality. And so I wanted to like, the ultimate would be to have some sort of interview system that like worked for everyone, that was generally applicable and yet still got interesting answers and didn’t take me very long to do. And the answer that I hit on, I kind of stumbled into it, I just started doing it naturally and it ended up working out was, every time I would do a text based interview, I did these interviews over email, I would ask pretty much the same questions. And then I would look at the responses and ask follow up questions. And then I would take a note, “Okay why did I have to ask that follow up question? What did they leave out that they probably should have included?” You know, “How could their answer have been better? Why did I goad them into getting a better answer?” And after a few months of interviewing companies from all sorts of different industries and verticals, I had a gigantic list of ways that people commonly gave uninteresting interviews and so I just factored that into my interview questions. I’ll have like a question followed by like 10 or 11 bullet points for like here’s how you should answer, here’s what you should avoid in your answer. Here are things that people like listening to and I started sending that to people and you know, instantly the interviews that I got back were much more entertaining and they were required less effort ’cause I can send the same packet of questions to everybody. It’s kind of, I guess it qualifies as a hack where I no longer have to do as much work.

Craig Cannon [00:17:29] – But they’re handwriting, they’re typing these answers in?

Courtland Allen [00:17:31] – Yeah, they’re typing these answers over email and every now and then I’ll send a follow up question, but it was optimized to be as little work as possible on my part so I could do other things like start the podcast. I was selling ads at the time, that took up like half of my time, etc.

Craig Cannon [00:17:46] – I found that the best hack for me, we did a bunch of interviews with the first employees at tech companies and the thing that worked was just doing audio interviews, transcribing them, and then doing insane amounts of editing. Because I found that there were just issues that you have trouble going back and forth to get deeper and deeper and deeper. Maybe you’ve figured this out through repetition, but giving someone one chance at an answer and then they painstakingly write the perfect answer often times it comes out kind of flat.

Courtland Allen [00:18:18] – Doesn’t work very well.

Craig Cannon [00:18:19] – No.

Courtland Allen [00:18:20] – It didn’t work for me early on which is why I had to do crazy amounts of follow up emails. I was just resistant to doing the call. I didn’t want to get on the phone with people. That’s why I was so scared to do a podcast. I don’t want to talk to people. I just like the whole behind the computer, type on my keyboard, and that’s it. But it worked out. When we launched Indie Hackers when we launched it last August, it was like 10 interviews and it took me three weeks. I sent hundreds of emails to get 10 people to agree to do an interview and one of them was me, so it was really only nine people. And now we’ve got 200, I think we just hit 200 this week interviews, 30 podcast episodes, and I’m working on that part of the business less than I ever have, so….

Craig Cannon [00:19:00] – What are the other parts that you’re working on?

Courtland Allen [00:19:02] – I’m working on the community right now. Indie Hackers started off as a content site, really a showcase for these types of profitable internet businesses, but today I would describe it more as a community of founders and inspiring entrepreneurs who are like sharing knowledge with each other and helping each other to build successful businesses. The real core of the site is the community forum. It’s just a bunch of people asking each other practical questions. How do I market my site? What do you think about my landing page? Should I change this? What do you think about my idea? How do you people find time to work on your projects when you have a family or a full time job, etc? And just helping each other out. That takes a lot of time to grow and I’m thinking about kind of harnessing the power the community to build tools to help these makers and these Indie Hackers to actually do better. What can they all work together on to make their lives easier? It could be something as simple as, you know, maybe a crowd sourced list of like the best podcast episodes for this month. I don’t want to dig through all the podcast episodes to find out what’s worth listening to, right? I want these other people to tell me, or all sorts of tools like that I think would be interesting for this community. I’m spending almost all of my time coding and talking to people and trying to figure out what to do there. Whereas my brother, who was brought on as part of the Stripe acquisition, is handling almost all of the editing for the interviews, and correlating with interviewees, and handling like the articles and finding people to write for Indie Hackers.

Craig Cannon [00:20:24] – Okay, so that now is like growth tactics to get people into the forum.

Courtland Allen [00:20:28] – Yup, exactly. And it’s kind of automatic. I mean I’m not doing very many tactical things. Things get submitted to Hacker News. I think that’s probably our number one growth channel, people on Hacker News reading interviews which is how the site got launched so it’s not particularly…nothing’s changed very much in the last year. It’s more about product. What’s the right decision, what’s worth building and what’s not? It’s a tricky decision because obviously you know as a one or two person team building something is a humongous investment and you don’t want to spend three months building the wrong thing.

Craig Cannon [00:20:58] – We have a handful of people coming up. One guy runs a site called Bigger Pockets. Have you seen this before?

Courtland Allen [00:21:05] – No.

Craig Cannon [00:21:06] – It’s basically like a giant real estate forum and they’ve created tons of educational content and I think they also have a bunch of, I might be mistaking this, but a bunch of calculators and stuff. Basically these tools that folks are interested in real estate investing need. And they’ve figured it out, after someone asked the same question 400 times in the forum, you’re like maybe there’s some amount of interest here.

Courtland Allen [00:21:29] – Exactly. I think that’s a cool model, too. When I was scouring Hacker News trying to come up with an idea, the company that I saw that inspired me the most and actually the first person that I reached out to for an interview afterwards was a company called Nomad List. Started by this guy Pieter Levels who’s always on HN, he’s like a crazy personality on Twitter as well, but what he did was built a resource for digital nomads, basically a list of all the cities in the world that you might want to travel to, and then just common stats that you would like to research. How fast is the internet, how safe is it, how expensive it? And so people who are digital nomads were like, of course. They want to do this research, they’re going to go to this site rather than scouring the web. And once he got them all in one place, he built a community and he’s sort of building tools for that community that are just for digital nomads like himself. I think that’s a pretty cool model. It sounds like this real estate site’s the same, Indie Hacker’s very similar.

Craig Cannon [00:22:14] – Same deal. A handful of people on Twitter asked this question so, you know Tom for instance. You know Pratheke, I’m getting their name wrong. Basically, how do you grow a forum is the question. Had you built a forum before? No idea?

Courtland Allen [00:22:31] – I had no idea. I just kind of winged it. I knew I wanted to have a forum so the day that I launched Indie Hackers I had a link on the site that said forum, but the forum wasn’t built yet. It just had like a sign up list, sign up forum.

Craig Cannon [00:22:44] – It would just go to a MailChimp list or something?

Courtland Allen [00:22:45] – Yeah, it’d just go to my MailChimp list and I wanted to see, okay how many people sign up from the mailing list from this page? It’s some sort of rough indicator whether or not people want there to be a forum or a community which I wasn’t sure of. You get people already talking on Reddit, they’re already talking on Hacker News, like maybe…

Craig Cannon [00:22:58] – This is a big question for a lot of people. Why would I build a forum when I could get discussion you know, even with my own Facebook group. What motivated you to do it?

Courtland Allen [00:23:08] – Yeah, I did a lot of things early on that a lot of people found unintuitive. They’re like, “Why would you do that? Why are you building your own website rather than using WordPress?” Or, “Why didn’t you just use a Medium blog? Why is Indie Hackers this dark blue website? It looks ridiculous. Why are you building your own forum? Why don’t you use Discourse? Why don’t you just use Facebook?” And my thinking from the very beginning was like your product, whatever you do, you should probably take, if you’re going to be invested in it for a number of years, you should take the time to make it stand out and be different and be yours. And I knew going into it also that I’m a computer programmer, the other ideas on my list before I chose Indie Hackers were all like kind of SaaS businesses that people have a lot more development and I begrudgingly chose the idea that was blog. Indie Hackers was a blog. Okay if I’m a programmer and I really want to do these other things but I’m going to do a blog, I’m going to allow myself to like to do some fun stuff and make some stuff to keep myself interested. And I also thought about what I didn’t like about blogs. You know the worst thing about blogs is when you go to something, a blog, and you read something good on it and then you come back a month later and you don’t even remember that you were there. There’s no way that you’re going to go to Indie Hackers and not remember that you’ve already been there because it’s a quirky, dark blue website that looks like nothing else on the internet. You might as well stand out, so I decided early on that I didn’t want to do the standard thing that other people were doing. I didn’t want to use Facebook for my community groups. I wanted to do it all in house and do it myself.

Craig Cannon [00:24:26] – If someone were to start a community, what would be your advice on getting a forum going?

Courtland Allen [00:24:35] – Okay so number one, I think you need to organize your forum around a topic that people can actually talk about and they actually enjoy talking about. It seems obvious, but people do it all the time where they start a community I think around something that people don’t really like talking about and they wonder why it’s empty.

Craig Cannon [00:24:50] – Like what?

Courtland Allen [00:24:51] – Just one off things. Let’s start a community about, I don’t know like something super specific like how do I incorporate? Well you can’t really have a community around how you incorporate because people will ask that question, it’s answered, and they’re out. Not only do people need to enjoy talking about it, but it needs to be substantive enough where they can come back and they can continue talking about it. Starting a business obviously qualifies because there’s endless challenges.

Craig Cannon [00:25:13] – Right.

Courtland Allen [00:25:14] – Number two I think you need to have some sort of strategy to continually drive traffic to it. It can’t be you launch your community on Product Hunt and then after that you’ve got no strategy. And this applies to any product, not just a forum. With Indie Hackers, if you were to think about the forum as the core product of Indie Hackers and the interviews as content marketing, I think that’d be a good model for how it works. I’m constantly doing these interviews every week. The interviews themselves are really entertaining. It proved early on that people on Hacker News, and Reddit, and other websites and Twitter enjoyed sharing them. I could do the interviews, get people on my mailing list, and then send out links to the community on my mailing list and continually drive traffic and kind of kickstart it over and over and over and over again for weeks. If you’re starting a community from scratch and you don’t have any way to consistently drive traffic to it, you’re at a tremendous disadvantage and you’re going to be sort of just having to pedal faster every single time you want to get more traffic. I didn’t have to do that. It was easier because I started with my content marketing strategy first.

Craig Cannon [00:26:10] – Yeah.

Courtland Allen [00:26:11] – And I think finally, you got to ensure that there’s good content and discussions going on early on. Like I, the first week created a bunch of fake accounts which I heard other people doing. I was like, “All right, this seems cheesy, but I’ll try it.” And I would have conversations with myself, I would have conversations with other people and never let anyone make a thread that I didn’t respond to and try to give them like a valuable response ’cause otherwise they’re not going to come back. No one wants to see an empty forum.

Craig Cannon [00:26:34] – No. It helps to think of interesting discussion topics, etc. As long as people like talking about what you’re doing, as long as you have a way to drive traffic there consistently, as long as you ensure that the conversations there are interesting I think over time the forum that you start will grow. To boil it down, there were no crazy growth like hack type things. It’s just you figured out a market where people are interested in reading a bunch of content about and made a bunch of content. Then they just ended up on your site and following you.

Courtland Allen [00:27:06] – Exactly. Yhe idea of the crazy growth hack is so overrated. Even when I sometimes do an Indie Hackers interview, people who read it on Hacker News will say, “Oh, just boil it down to this one trick that this person did.” And that’s never the case, you know? I think we all want it to always be like, oh it’s this one thing that they did that’s responsible, but it’s not. It’s almost always like they got the basics right, they made something that people actually wanted which is deceptively simple advice. It sounds simple but people always subtly do other things that aren’t making something that people want and wonder why no one uses their product. The tricks I think are overrated. Make sure that you build something that people want that’s good and then make sure that you’re actually thinking about how to get people in the door, that you’re not obsessed with the product itself.

Craig Cannon [00:27:47] – Right, yeah I mean it’s the, I mean people call it what, leaky bucket, all this stuff. It’s continually a piece of advice that when we’re talking about content or content marketing with any YC startup, make something that you’re going to want to read.

Courtland Allen [00:28:00] – Right.

Craig Cannon [00:28:01] – You know doing these listicles that no one really cares about and your site looks like Medium so no one remembers what it is is kind of just wasting time.

Courtland Allen [00:28:09] – Yeah I know. I did the same thing too with my YC company, we just slapped a blog on our website. It was so boring. We would like announce new features every now and then.

Craig Cannon [00:28:15] – Totally.

Courtland Allen [00:28:16] – It would be empty for like six months. Whereas some of the most interesting content online is treated as if it is the product, right? Indie Hackers, the content was the only thing on the site for months. I think you need to put that level of detail and thought into it and like we were just talking about, be creative. Content doesn’t even have to necessarily look like content. The content on Nomad List was like a database of cities with information about them. That’s not traditional content, but it’s interesting. How many interviews do you cut?

Craig Cannon [00:28:49] – Text interviews or podcast? Oof.

Courtland Allen [00:28:52] – I mean the answer is zero, actually.

Craig Cannon [00:28:54] – Oh zero, they all go to print or publish or whatever?

Courtland Allen [00:28:57] – I don’t think I’ve ever conducted a text interview that I didn’t end up putting up. There might have been like one or two where someone was just a complete jokester and gave like one sentence responses and I sent it back to them and they just never responded. I mean that wasn’t me cutting, that was them never responding.

Craig Cannon [00:29:11] – Okay.

Courtland Allen [00:29:13] – I think a good interview you can really coax out of anybody if you’re willing to put in the time and the effort.

Craig Cannon [00:29:18] – Well, so that’s the text thing is what kind of strikes me because in person you get the vibe, okay they’re going to be a little bit difficult but you kind of warm up the room and they’re good. When someone’s not responsive over email or not specific or not as interesting as you think they could be, how do you get better answers out of them?

Courtland Allen [00:29:41] – Follow up endlessly until they either quit or they give you a good answer. I mean what we also do sometimes is we’ll put their interview on the site as a draft with some inline comments. Like, “Oh this is a really interesting answer.”

Craig Cannon [00:29:54] – Oh really?

Courtland Allen [00:29:54] – “Care to give us some details besides what you gave us? It would be awesome if you added a chart or graph here in your interview.” From the outside looking in maybe it looks like people are magically just giving good answers, but sometimes you just have to coax them. Like you said, in person you do that by feeling out the room and just vibing off the other person. Over text, you just take the tedious time to just point out what’s wrong and how it could be better.

Craig Cannon [00:30:17] – Okay, fair enough. Question from Tom… The question is what was the hardest with Indie Hackers but I think what he means is what was the hardest thing about building Indie Hackers?

Courtland Allen [00:30:29] – Managing my time early on, but I already kind of talked about that. What else was difficult building Indie Hackers. I think doing it alone is difficult and I’m super lucky because the site itself in a very meta way is about building startups, it’s about starting companies. The way that I look at it, my mental model for building a startup is essentially your whole goal is not to quit. I saw a really good tweet the other day that was, “Here’s the secret to success: Pick any idea, work on it for 10 years, you will succeed. Just don’t quit.” The way I look at a startup or any sort of company is imagine a race or a marathon where if you get to the finish line, you win. Depending on how skilled you are and how much you learn, and how good your product is the finish line might be further away or closer, but all you have to do is keep running and not quit. When you are a solo founder, it’s really easy to quit. Every time you run into a hurdle, you’re like I can quit here. I don’t know how to get past this. And a lot of people end up quitting way too early just because they’re not prepared for that. They think that the typical startup story is you just succeed after a couple weeks.

Craig Cannon [00:31:32] – You launch and then you’re like set.

Courtland Allen [00:31:33] – And it’s set from there. I failed enough times to know that’s not the case. You don’t win by quitting. You don’t win by succeeding overnight. It’s a slog.

Craig Cannon [00:31:43] – But the content thing, it’s new for you right? You hadn’t done a content thing before.

Courtland Allen [00:31:47] – No, never.

Craig Cannon [00:31:48] – Right, and so content can feel like a treadmill.

Courtland Allen [00:31:50] – Yeah, it totally feels like a treadmill. That’s what I was talking about earlier with having that kind of rubric that I send out. It really helped with that, but it never felt like as long as I got the content under control, it never felt like I was on a treadmill. I felt like, “Okay that’s fine I just need to have enough time per week to work on pushing the business forward so I would have three or four days a week to work on advertising.” And that was a huge hurdle. I almost quit when I had no idea how to do ad sales because I’m not a salesperson. I’ve never done any sales before. But after two months of trying I’m like, “Hey I’m pretty good at this.” I’m sending cold emails to people and getting them on the phone and like making friends and people are buying adds on my website, it’s working out. Same with the podcast. Never done it before and it ended up going pretty well, but back to what was hard about it… Any time where I let myself dwell you know in solitude for way too long was when I would think about, this is hard. When I would open up to the community and send an email saying, “Here’s what I’m working on, here’s what’s hard,” and get support, and it suddenly was much easier. To go back to the marathon analogy, if you’re sort of running this marathon by yourself and you look around and no one else is running, of course you’re going to quit if it’s hard. But if like a whole bunch of other people went running with you, then suddenly the social proof of that just helps you continuous…

Craig Cannon [00:33:05] – By kind of forcing yourself to work in public, you could stay motivated?

Courtland Allen [00:33:09] – Yup, exactly. I think that’s a good reason why I push people to be transparent, come on the site. You have very little to lose, you have a lot to gain because people will identify with you, you’ll make friends, people like your personal story, they want to know what’s going on behind the scenes. And this whole corporate veil of always saying “we” and never sharing any numbers, it’s just so boring. Who connects with that, you know? Nobody wants to read that kind of stuff.

Craig Cannon [00:33:31] – Yeah, especially when you’re on your own and just working at your little tiny bedroom office.

Courtland Allen [00:33:35] – Exactly. Unless you live in some sort of tech hub, most people around you don’t know what you’re doing. The internet’s pervasive, but starting an internet business is still a pretty rare thing to do and so I think being able to rely on some sort of online community, whether it’s on Indie Hackers or another site. If you can go somewhere and people are also doing what you’re doing and you can tell them what you’re up to and they can give you feedback and really just identify with you, then you’re much less likely to quit.

Craig Cannon [00:34:00] – How do you maintain a positive community?

Courtland Allen [00:34:04] – I do very little actually. I was worried about it because I’ve been a member of Hacker News for like eight or nine years and I have mixed feelings about it. I love it because the content there is good. People surface really good links. The discussion is very interesting, there’s a lot of smart people in the comments, but it’s also super negative. The vibe is who can say the most contrarian, negative thing first? That’s going to get all the upvotes to almost everything that gets submitted. I was worried about the same thing with Indie Hackers especially since so many people on Indie Hackers came from Hacker News. But I think it’s naturally a little bit self-policing because these are all people who are very serious about building businesses. There are people who have done it before, who’ve perhaps shared their project on Hacker News or Product Hunt or something and got negative comments so they know what it feels like, so they’re the last people who are going to’ like bash what other people post. They’re not going to be negative assholes because they know what it feels like to be on the other side of it. They have if not the emotional intelligence, at least the experience to be like, oh that sucks, maybe I should be careful just give positive feedback or like constructive criticism. I’ve luckily not had to do very much at all to prevent people from being negative. And I also think that the community, it’s not a link posting community. You don’t go on Indie Hackers and just share a link to something and then say nothing else. You actually have to have a discussion. And so you’re actually, from a personal perspective saying, here’s what I built, here’s what I did. And I think it’s a little bit harder to be an asshole when the person who wrote the post is also the person who submitted it.

Craig Cannon [00:35:25] – Yeah I think that it de-arms people even on HN. When you get into the thread, I advise people this all the time, just like get into the comments. People respond much more positively when they know you’re in there and you sincerely want to engage. But it’s weird. They’re like, “Oh this person made it onto the internet. What do I do?” Uh, delete account. Someone asked an interesting question which is, would you advise starting indie hackers, meaning like a person who’s getting started to join an accelerator?

Courtland Allen [00:35:58] – Yes, I would. I think, okay so I’ve only done YC. I can only really vouch for YC and the boring answer is obviously depends on the accelerator. If it’s Y Combinator, undoubtedly yes the advantages outweigh the disadvantages tenfold. It really goes back to what is it that kill startups? People quitting. What do people very rarely do? Quit out of an accelerator when they’re surrounded by other people doing this and investors are pushing you along. For no other reason than that I think it makes sense to join an accelerator. But also, the mentorship that you’re going to get, the advice that you’re going to get. I’m really big on founders joining any sort of community. If you can find a way to position yourself around other people doing what you’re doing then you’re going to increase the chances of your business succeeding. The caveat is usually accelerators come with investment terms and investors and you need to go in that with both eyes open. I spent some time doing contract work and I worked for a lot of VC funded startups for a few years and it was so interesting in talking to the other employees there or sometimes the founders there because they would build a very good product that maybe 20, 100 thousand people are using, people were paying for and then sometimes just crash and burn because you know the level of success they needed to reach in order to meet their investors expectations was so high. I think if you go into any sort of accelerator, if you accept money from investors, you need to be aware that, yes the money might help you succeed and grow faster, but at the same time it’s also raising the minimum bar for success. And if that bar gets raised too high to a degree that’s unrealistic for your product to hit, if you’re building a to-do list app and you know, you need to be a billion dollar valuation, like good luck. There aren’t very many billion dollar to-do list apps, you know? I think you should be aware of that if you’re going to join an accelerator.

Craig Cannon [00:37:45] – Yes that is a protip from Silicon Valley. Just know the terms of the deal. Know the expectations. It’s not crazy, but I think it’s one of those themes that people are really attracted to with Indie Hackers ’cause it’s this unsaid… I don’t think VCs are ever trying to be in the gotcha position because it doesn’t work out for anyone if the company doesn’t work. But when you set your expectations in life to build this billion dollar company and you’re raising money and then you realize that you’re making a to-do list app.

Courtland Allen [00:38:15] – You’re not going to’ hit that. I think like a lot of it is, like I said earlier, people just hear one story. They don’t really think about what kind of deal they’re making, or why they’re going that route, or why they feel the need to build a billion dollar company. I agree with you as well, the VCs aren’t super nefarious. They’re not like I want to trick everyone, right? But at the same time, their incentives are such that 90% of the time, they would rather have a whole bunch of people fail and a few people make it big then to have everybody have kind of a middling result.

Craig Cannon [00:38:46] – Right.

Courtland Allen [00:38:47] – If you’re a founder, you have to ask yourself do I want to have a high risk of failure to have that one shot at the top? Or do I want to maybe make 10 or 20 thousand dollars a month or a small exit or something and then maybe go for the big shot, which I think is probably the more rational decision for most people.

Craig Cannon [00:39:02] – I’d imagine so. There’s another question from Burt. Are there other recipes for folks growing a side hustle or small business, whatever you want to call it, in Europe compared to the US?

Courtland Allen [00:39:18] – I don’t think so. The reason is because if you compare working on a side hustle to building more of like a high growth startup, if you’re trying to hit a billion dollar valuation, what do you care about? You care about, really what you need is this potent confluence of factors all pushing in the same direction. You need the best idea ever. You need the best team ever. You need a growing market that for some reason has like no real competitors or a bunch of bumbling competitors. You need the best investors, the most money, a little bit of luck. You need everything to help you. Whereas if you’re building a side hustle, if you’re building a smaller business that still might be life changing but doesn’t need all the luck in the world and every factor to line up, then really all you need are solid business fundamentals that’s eminently learnable. And those are going to be the same no matter where you are. Whether you’re in Europe or the US, you still need to build something that people want, you still need to have some sort of marketing and distribution strategy. You still need to be able to manage your time and not run out of money, etc. That doesn’t change from place to place. The only thing that really changes is the number of people in your community who understand what you’re doing, your access to capital if you want to raise money, legal things and taxes, but everywhere I’ve been, I mean I went to South Africa, I talked to some Indie Hackers there. You’re building a business for the internet. Your customers are everywhere. It doesn’t matter where you live.

Craig Cannon [00:40:37] – Are you only interviewing SaaS companies?

Courtland Allen [00:40:40] – No, I interview the most random variety of companies. I tried early on to have some sort of rubric and generally if somebody emails me and they’re like, “Hey I have a consultancy.” I say, “You know that’s not the best fit ’cause you’re really just trading dollars for hours.” However, I think SaaS companies are kind of the most interesting. They’re kind of the dream of people who want passive income and people who want the freedom that comes with that lifestyle. But there’s lessons to be learned from other companies too. A good one is Scott’s Cheap Flights who did one of the coolest text interviews on Indie Hackers. It’s basically this guy Scott who found super cheap flights for himself and all of his friends were like, hey I want cheap flights too. How did you go roundtrip to whatever for like $200?

Craig Cannon [00:41:21] – Dude, like the Venn diagram of nerds and airline hacking things, you would believe how many YC applications. We’re going to blow your mind with this new mileage plan.

Courtland Allen [00:41:27] – People really like saving money on flights. It’s a little insane. Like people will spend way more money saving money and like time saving money on flights than they could earn if they just worked. But anyways, Scott was super good at it. He built this email list of friends and colleagues and sending the flight deals that he was finding for himself and it turned from that tiny side project into this massive business that’s doing four million dollars a year. It’s not SaaS at all, right? It’s Scott and his friends now, and the people he’s hired scouring the internet manually sending people.

Craig Cannon [00:42:00] – That’s it, there’s no bot.

Courtland Allen [00:42:01] – There’s no, that’s it. And people pay to be a part of this mailing list. They pay to be frequently sent cheap flights so they can go and it’s totally worth it for them. That’s not a SaaS company. One of the coolest interviews ever. And again, it’s all the same business fundamentals. Make something that people want, you need to find a way to actually advertise this mailing list and get people on it. His marketing site is super slick, super streamlined, like the conversion rates are extremely high. Super transparent about everything. And it makes his emails fun ’cause it’s like, “Hey, it’s Scott here.”

Craig Cannon [00:42:30] – Oh, that’s cool.

Courtland Allen [00:42:30] – It’s like you’re getting an email from a person that you know who’s trying to help you out.

Craig Cannon [00:42:34] – That is really cool. You spoke about the Nomad List guy before. Were there other role models for you when you were… I completely agree that it’s so important. We’re having Pete Adeney, Mr. Money Mustache, on the podcast.

Courtland Allen [00:42:48] – Oh cool.

Craig Cannon [00:42:49] – And he’s awesome, but I think his whole deal was so influential with people in that he’s just like software engineer for 10 years, saved up like six or seven hundred K and was like, “I’m out.” Index fund, rely on the income from that. But I think he’s just another example of showing people the way. Were there other people that were kind of showing you the way?

Courtland Allen [00:43:11] – Yeah, David Heinemeier Hansson from Basecamp was a big one and Jason Fried. So I went to Startup School in ’09 and saw Jason Fried talk, but my favorite talk was DHH’s talk the year before. It was just super entertaining if you haven’t seen it, you should watch it. But he completely just dissed everybody there and he was just saying common sense things like you can build a business and telling people things they hadn’t heard before. Whenever I felt low, I would watch it. I’ve probably seen that talk like 50 times just ’cause it’s so inspirational.

Craig Cannon [00:43:38] – I never watched that one.

Courtland Allen [00:43:39] – It’s a really good one. Who else? I think Pieter Levels was a big one, I mentioned. I didn’t have that many influences. When I was reading through the Hacker News threads to find examples, I found a lot of really cool examples. And people are always like, what they’re doing is awesome and that inspired me to know that it was possible and keep going, but there isn’t any one person.

Craig Cannon [00:43:58] – What about the idea of just the idea of making a content site? You were reading some, cause HN is an aggregator, right? Was there one site that stood out and like, oh this is cool?

Courtland Allen [00:44:09] – No, I mean, I think. This is a big thing that I tell people all the time. Your products, you shouldn’t start by thinking about what your product is going to be and then making that. Where you should start is by figuring out what people want and then based on what people want, you find the best possible way to give them that. What people wanted in the situation was really two things. They wanted to do what I was doing and like have some sort of easy way to research ideas for products, and number two, I think people just found it entertaining to read these stories. The conclusion I came to after seeing that was like okay, if I really want to provide what people want it’s going to be some sort of content site. Whether it’s interviews, whether it’s a podcast, whether it’s videos, it’s completely up in the air. All of those are valid solutions to that problem, but I for sure need to include some transparent revenue stats. I for sure need to get some behind the scenes details. There are things that if I really wanted to give people what they wanted were absolutely required and so I make sure to just do those things. Like I said, I’m a developer. Starting a content site sounded so boring to me and I was so upset that that was the best idea that I came up with, but I was also excited about it.

Craig Cannon [00:45:14] – Is the back end of the site user friendly at all? Are you like publishing from the terminal?

Courtland Allen [00:45:19] – It’s not user friendly at all. There’s the whole bus factor, if you get hit by a bus, how can your product stand up, can someone else come in? At Indie Hackers…. I look both ways when I cross the street.

Craig Cannon [00:45:33] – Exactly, yeah we’re WordPress now for that exact reason. Alright, are there common failures with a lot of these Indie Hacker founders that they describe as maybe something in the early days that they struggled with that’s common between many of them?

Courtland Allen [00:45:52] – Yeah, you hear the stats all the time. You know 90% of businesses fail, but I think the earlier and earlier you go in the funnel the more failures you see. The ultimate top of the funnel, most failures you see is people who are interested in starting a business but never get started. Not for lack of motivation or care, but because they don’t know what the first step is, right? They are grossly misinformed about what the first step is. For example like I said earlier, spend five or 10 minutes thinking up an idea every now and then, it doesn’t come to them, and they conclude that they just can’t do it. Whereas actually you should probably dedicated three or four days to come up with an idea ’cause it’s this inflection point that’s going to control the next few years of your life and it’s not easy to come up with one off the top of your head. People get kind of frustrated by that and stop. Or they won’t be able to figure out the legal situation early on, so they’ll stop. Which is why Stripe has Atlas for example to help people out and make it super easy. Not having traction in the early days, super frustrating to people and they quit. Consistently, I sound like a broken record here, but it’s like the more times I say it hopefully the more it’ll sink in. People quit way too early, way before they should quit. Some people think their ideas are terrible. They’re like, “Guys, my idea was so flawed.” And they’ll tell me their idea and I’m like, that’s a great idea, you just have to execute on it. I think that hurts. The other thing is, I don’t think people read enough and I get the opposite of this often. Oh stop reading and just start doing. That’s true, but I think if you’re the kind of person who is going to have the determination and the grit to actually start a successful startup, then you’re probably not going to quit because you spent too much time reading upfront. That’s not going to’ be what stops you if you’re that type of person. But the benefits of reading are massive because starting a startup is not intuitive. If it was intuitive then there wouldn’t be so many guides and books to doing it and everything you did that felt right would just work. But anytime you see an industry that’s populated with intelligent people, yet most of them are still failing, it’s probably worth taking a step back to say, there’s something going on here that people don’t realize and I should read and learn from other people’s mistakes instead of repeating their mistakes and learning from my own horrible experiences. And that’s not to say that experience is not a good teacher.

Craig Cannon [00:48:04] – I’m really good at that. What do you tell someone when they’re like, okay, I’m in. I’m subscribed to your workout plan. I’m going to spend four days and get my idea. What do you tell them to read?

Courtland Allen [00:48:17] – I tell them to read the Indie Hackers interviews which are just a better version of the same HN posts that I was reading. I tell them to post on the forum, share what you’re doing. Don’t go into a blackhole and emerge two months later and be like, I never did find an idea. Why don’t you just keep a list of what you were saying, coming up with, and post them on the forum and people are happy to tell you what they think, what you should do next, etc. I think there’s this kind of overwhelming assumption that we’re just alone and you can’t share. Because there’s not that many communities where people do this. I get it, it’s not a common thing. People just aren’t used to it. I’m trying to reverse that. Someone said on the Indie Hackers forum earlier that they would like it if I made the forum a little bit more structured and created a specific way to ask for feedback because he felt spammy. I don’t like spamming people and asking, that’s the entire point of this forum is for you to ask these questions and it feels spammy. I think I’ve underestimated a little bit how much it can be scary or feel like not, just not normal to ask people for transparent advice on what’s going on. That’s my advice to people. As long as you have mentors and people who know what they’re talking about who can help you out and as long as you don’t quit, even if you do things wrong. You’re going to get some good advice and you’ll be able to correct.

Craig Cannon [00:49:28] – Okay, were there any books that guided you?

Courtland Allen [00:49:31] – I love all of the most popular startup books. The Lean Startup is great by Eric Ries. I like Crossing the Chasm, it’s a little bit older, it was kind of The Lean Startup of the 90s I think, but still great advice there. It talks about the early adopters and all the way through the mainstream and late adopters and the difference between appealing to those different segments which I think is extremely important for people to know. I like Peter Thiel’s Zero to One. I think the thing that trips a lot of people up while I’m talking about these books is that not every book is going to tell you who it’s written for. If you read Zero to One, that book is written for high growth startups. It’s got a lot of advice in there that’s terrible if you’re trying to bootstrap your way to success. People will come in and say, you know like I did this thing and it’s not working. Why’s it not working? ‘Cause that’s advise that does not apply to you. But I think if you’re careful and you understand who was this written for and what nuggets can I take away then almost all these books have some nugget of advise that’s useful. Hooked by Nir Eyal, really cool book. Talks all about the psychology of habit forming products and what gets people coming back, why do we form all our habits, etc. Totally unaware of that until I had him on my podcast and I read the book. Ryan Hoover helped like edit it as well.

Craig Cannon [00:50:45] – Oh cool.

Courtland Allen [00:50:46] – That’s probably why Product Hunt is so addictive. But really cool book, definitely worth a read for everybody. And also, just books outside of the startup echo chamber. I have so many people who say, “Courtland I have this idea for an app that will let you place an order at your local coffee shop before you get there,” and I hear this idea like seven times a week. And the reason is because everybody’s reading the exact same books and the exact same blog posts and living in the exact same place. And so if you all have the same inputs, you’re going to have like the same ideas as everybody else.

Craig Cannon [00:51:14] – Totally.

Courtland Allen [00:51:15] – If you really want to come up with something creative, like not only should you invest the time to think about it but travel, go visit a different culture, read some fiction or some sci-fi or something to get your creative juices flowing. Don’t only read startup books.

Craig Cannon [00:51:28] – Yeah, I think you have to have an opinion outside of the norm.

Courtland Allen [00:51:32] – You do.

Craig Cannon [00:51:33] – Because it’s true, just hang out here long enough and it’s the same ideas circulate.

Courtland Allen [00:51:37] – Exactly.

Craig Cannon [00:51:37] – Yeah. Do any of the, so this is a Cameron Reynoldson, how often do you see Indie Hacker projects transition from lifestyle businesses to startups, or do they ever?

Courtland Allen [00:51:49] – Yeah, all the time. Scott’s Cheap Flights, great example. It depends on your definition of lifestyle business. If you mean lifestyle business as any business that makes money and a startup is someone who’s raised money from venture capitalists, actually you don’t see that very often. Very rarely does somebody who is killing it and making millions of dollars decides that they’re going to raise a ton of capital. And I think most of those cases are pretty famous. But I see the opposite actually often, which is companies will raise one round and they won’t raise any more money. They’re like, yeah we’re killin’ it, we don’t need to raise any more money. We understand what level our investors expect us to get to and we’re comfortable with that. Zapier is a good example, we had Wade on the podcast. They’re doing extremely well, he doesn’t need to raise any money. Kevin Hale at Wufoo did the same thing back in the day. And I also see a lot of side projects that start off as I just want to supplement my income and make a few thousand bucks a month that turn into, I’m quitting my job, this is it full time. This guy Mike Perham created an app called Sidekiq, it’s basically like a background job processor for developers so they can run tasks in the background of their server and make their websites faster. He was doing it on the side of his business. Then he was kind of mixing it with his business, then he quit his job and was like I’m not going to work my full time job while this is taking off, right? And that’s kind of the dream ’cause now he has the freedom to work on whatever he wants from wherever he wants for whatever hours he wants and there’s no upside on his income. He’s making something like a million something dollars a year as a solo developer just doing what he likes. Not a typical story, not everybody makes a million dollars a year. But that definitely went from like side project and hobby into like more than a full time career.

Craig Cannon [00:53:25] – But that’s a real struggle. I know a bunch of software developers that have their cushy internet job and have a side thing and they struggle to figure out at what point do you really switch. Is there an advise section in the forum that people like struggle with this question? Or is this actually more rare than I think?

Courtland Allen [00:53:46] – Oh, it’s very common. Indie Hackers as it exists right now is not very prescriptive. It’s not organized into an answer to every specific question you might have, it’s more free flowing. And so every now and then a topic might pop up about that and people will get all sorts of good responses. But my personal advise would be it really depends on the level of risk that you want and it’s harder once you’re a developer or even a non-developer in some job where it’s cushy and you’re making money. When I first moved out here, I was the stereotypical you know, 22 year old eating ramen noodles. I didn’t care what kind of apartment I lived in. And then I started shopping at Whole Foods and moved into a better apartment. Now it’s, okay I can’t, I can’t quit my job or do something unless I have a really good idea that’s really working out. And I empathize with people who are in that situation. I really think that you should have some form of product market fit. You should be confident that your product can work. If you’ve launched a side project and there’s no one using it yet and you’re just excited to code on it, that’s probably premature for you to leave your job, right? Every software engineer really likes coding their own thing, it’s fun. But you really need to get to the point where you found a way to get people to your app. You found a way to actually grow your revenue and you can say, okay at this rate it’s a matter of time. I think that’s helpful. And I realize it’s kind of intimidating if you’re not a person who would describe yourself as a business person, right? If you’re like, I write code, I have no idea what it means to do business. Really there’s no such thing. It’s just a collection of individual tasks like finding people to come to your app, right? Which if you read enough examples, you’ll start to see the patterns, you’ll start to see what options are available to you. And so I would encourage people not to be worried that they don’t have experience here, just make sure to read and learn from what other people are doing, make sure that you’re persistent, that you don’t quit at the first sign of distress, and then if things start working, it’ll be pretty obvious. With Mike Perham it was like, hey I’m making 50K a year from my app. 100K now, wow it’s only been two months. Or you know, with Scott’s Cheap Flights, suddenly I’m making thousands of dollars, I can hire somebody. Why do I need to work my job?

Craig Cannon [00:55:51] – Also, if you’re a talented developer the downside’s pretty low, right? Ideally it’s make enough money to sustain you, you spend six months on it and if it doesn’t work out you can get another job.

Courtland Allen [00:56:03] – Exactly. I mean that’s what I did. I was contracting, I quit and I had enough savings to live for like a year or two in San Francisco which could’ve got me much further in any other city. I do not recommend trying to bootstrap in San Francisco paying ridiculous rent here. But ultimately it’s, okay I’m confident that if things don’t go well like I’ll have a backup plan. It’s much harder if you’re in a different situation.

Craig Cannon [00:56:24] – Yeah, for sure. How are things going now that you’re at Stripe?

Courtland Allen [00:56:28] – Awesome.

Craig Cannon [00:56:31] – They’re not watching.

Courtland Allen [00:56:34] – Stripe is a great company. It’s so funny because the acquisition happened completely out of the blue. People ask me, “How did you set up for the acquisition and blah, blah, blah.” I’m like, “I started a blog.” No one starts a blog to get acquired, you know? The email came completely out of the blue from Patrick, but it’s really the perfect union. I think some people every now and then will be skeptical especially on Hacker News about any sort of acquisition, like what’s the real play here? I think it was obviously good for me, it’s good for Stripe, and it’s good for the Indie Hackers community, for Indie Hackers to be under Stripe. Specifically if you look at Stripe’s goals and incentives here, I mean Patrick Collison came in on the Hacker News thread that announced the acquisition and made the top comment where he just said flat out here’s why we’re acquiring Indie Hackers. And it was super straightforward which is Stripe does better if more people are starting companies and those companies are more successful. Indie Hackers’ mission is to help more people start companies and be more successful. There’s no man behind the curtain there, there’s no secret thing going on, you know? And also, just examining a world… Indie Hackers without Stripe versus Indie Hackers at Stripe. What I was doing back in February, March is spending an inordinate amount of my time finding advertisers, putting ads in my newsletter, putting ads on the website, putting ads on the forum. Ads as much as they might fund a site, they don’t make it better. No one is happy to get a newsletter that’s got ads in it. It doesn’t help anyone, right? It didn’t help me to do anything other than pick up the ability to–

Craig Cannon [00:58:00] – Pay rent.

Courtland Allen [00:58:01] – Yeah pay rent, right? But ultimately at Stripe I’ve got a salary, I don’t have to worry about paying rent. I’m not like worried that Indie Hackers is going to go under. They’re not going to shut the website down. They did not buy it to shut it down. They did not buy it to become some sort of super profitable thing in the next six months or anything, so the long term is pretty much set and now I can just focus 100% on my original mission which is just helping people start companies and showing that there’s another way to do it that’s not the story that we’ve all heard. Stripe’s been super fun, they’re really hands off. I think I’ve met with Patrick like three times since I’ve joined in the last six months and he’s a super smart guy. We just brainstorm together and think about how to make the site impactful. It’s really the perfect acquire and the incentives are aligned perfectly. There’s nothing that I want to do that they don’t also want to do.

Craig Cannon [00:58:41] – That’s great. Do you have any side projects going on right now?

Courtland Allen [00:58:43] – No.

Craig Cannon [00:58:47] – If you could start any side project which one would you be jumping on?

Courtland Allen [00:58:49] – What would I start?

Craig Cannon [00:58:51] – Tell me it’s going to be a coin. It needs to be…

Courtland Allen [00:58:54] – Indie Hackers ICO, really. I don’t know actually. You know what, I think I would, my side project would be, I would follow the same formula that I followed last time. I need to spend four days, get my brain into that mode where it’s actually good at this. It’s like riding a bicycle, if you haven’t ridden in a while and you’re going to suck, but after you pedal for a while you get good. Coming up with an idea, you need to take the time to do it. That being said, I think if you run a business for a while you start to see opportunities for things where if that existed you would pay for it for sure. I’m trying to manage my Twitter account, it’s just a hassle to do that and also do all the other things. I really want better tools for social media. A lot of tools for social media already exist and a lot of them are wildly popular and profitable. I’ve got some ideas in that area. It’s hard to say, but I think maybe the day will come where I work on a side project on the side of Indie Hackers. We’ll see, I’ve way too much to do now. And a lot of the stuff I’m doing for Indie Hackers is almost side projectish. My life hasn’t changed very much at all. I’m still working at home on Indie Hackers. Still working my own schedule.

Craig Cannon [00:59:55] – Solo operation.

Courtland Allen [00:59:56] – Yeah, exactly. It’s not too different.

Craig Cannon [00:59:58] – Cool all right, I don’t have any more questions.

Courtland Allen [01:00:00] – Cool.

Craig Cannon [01:00:01] – Thanks for coming in.

Courtland Allen [01:00:02] – Yeah it was fun.

Craig Cannon [01:00:03] – Alright, thanks for listening. As always, the transcript and video are at If you’d like to apply to the winter 2018 batch, that is at


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