Job Description: Inspire People to Start Businesses

Courland Allen Interview

Courtland Allen living life!

Please welcome Courtland Allen to Hacker Noon! Courtland started and runs IndieHackers.com, a great site for the startup community and entrepreneurs of all shapes and sizes. As a bootstrapped startup covering many types of startups, I greatly appreciate how Courtland shines light on the bootstrapped and profitable entrepreneurs. He’s interviewed 320 entrepreneurs, and I hope my interviews can be half as good as his. Indie Hackers is up to 25k community members, 30k email subscribers, 1.1M podcast downloads , and 1.2M monthly pageviews. If you have any additional questions for Courtland, feel free to leave a comment or start a discussion in the Indie Hackers community forum.

When/how did you come up with the name Indie Hackers? Was the domain available? Do you watch a lot of indie movies?

The first thing I did after deciding to work on Indie Hackers was come up with the name. I spent an entire day focused on that task and nothing else, periodically texting my brother and my girlfriend to get their opinions. I still have all of those messages saved:

If you’ve ever spent hours trying to come up with a good name for a website, then you know it can be a grueling process. All I wanted to do was start coding, but I couldn’t, because I didn’t know what to name my repository.

But I figured it was worth spending a full day on it, because if everything worked out I’d be using the name for years. I didn’t want to make any obvious mistakes that I’d come to regret.

Indie Hackers was actually one of the first names I came up with, but the domain name was taken, so I kept looking. Eventually I decided to email the owner to see if he was willing to sell it, and he said yes! It cost me $2,000 — he wouldn’t budge on the price — but I was just happy to get the domain.

The design of Indie Hackers is great. Also really like that you provide full transcripts of podcast episodes. Could you share a bit about the design choices, as well as, what’s under the hood (how you made it), and how the site has evolved?

Thank you! In addition to the name, I put a lot of thought into the design early on. I wanted Indie Hackers to become a community, so it felt important to imbue the site with its own unique personality. It needed to be memorable. It’s a real tragedy if someone visits your site three or four times without remembering that they’ve already been there.

Almost every other media site on the web was white, so I decided to break the rules and make Indie Hackers dark blue. I think doing the opposite of what everyone else is doing is underrated.

The tech behind Indie Hackers is a different matter entirely. I over-engineered it and made it far more complex than it needed to be. And I did it for purely selfish reasons, too. If I was going to spend my days working on a content site, I at least wanted to have some fun tech to play with.

Indie Hackers is built on Ember.js, a framework for creating single-page apps that I absolutely love working with. It’s only gotten better over time. On the back-end, I’m using Ember Fastboot with node for server-side rendering, so you don’t have to wait for the JavaScript to load and render the app before you can start reading. I’m using Firebase for data storage and AWS for hosting.

One thing I’ve had to learn a lot about is caching. It’s no fun if your content site goes down every time it does what it’s supposed to do and attracts a lot of readers. I have a fairly creative caching strategy, and it’s only gotten more complex as Indie Hackers has evolved from a media site into a community site that resembles a social network. I still have a lot of work to go here to get the performance where I want it.

You’ve interviewed A LOT of entrepreneurs. Especially, early-ish into their startup journey. What common traits have you noticed that led to the growth of their businesses?

They try a lot of things, abandon the failures, and pour gas onto the fires. They’re good about leveraging whatever existing advantages they have. They’re hard workers, and they actually enjoy building things. It’s not a chore for them. They don’t need a special trick to get out of bed in the morning and go to work.

The pop culture image of startup founders going out and hitting a grand slam on their first try is usually bullshit.

The most successful people I’ve talked to are the developers who are always working on new side projects and ideas, and who are capable of actually getting these projects released. They’ve taken dozens of swings, most of which were misses, but they kept swinging anyway.

There’s something special about starting new things from scratch, over and over. It gives you a chance to consider what you learned in the past and do things better the next time around. It gives you perspective, so you’re more likely to know when you should double down because you’re actually onto something. And of course it gives luck a much bigger chance to strike.

I think this applies to other things, too.

If you want to learn to be a good designer, go out and design 100 websites. Don’t just iterate on one website forever.

Being weird is underrated. I mentioned this earlier, but it’s worth reiterating. People genuinely enjoy novelty. When we see the same things over and over, they become etched into our brains, which makes them predictable, which makes them boring, so we lose interest. If you read the same books as everyone else, eat at the same restaurants, work the same jobs, and travel to the same places, then you’ll come up with the same boring ideas.

A lot of the more successful founders I’ve interviewed are weirdos. They’ve got a different set of inputs that they’re working with, which leads to different outputs. They’ve also removed the filter on their output that tells them to conform and not take risks. They make weather apps that curse at you. They tweet about the contents of their bank accounts. They think everyone should be subscribing to candy. Etc. It really stands out.

And when they get that initial burst of attention, they run with it. They don’t just let it fizzle out. It’s tempting to believe that you just need one lucky break upfront, or one successful launch at the beginning, but that’s rarely enough. Decline sets in. Entropy doesn’t want you to succeed. The success stories often involve the founders figuring out how to parlay small temporary advantages into big lasting victories.

Indie Hackers sold to Stripe in April 2017. Could you tell us a bit about how that acquisition came to be? Why did it make business sense to sell at that time, and how have the business goals changed since joining Stripe?

The Stripe acquisition offer came out of nowhere. It was perhaps the luckiest in a long string of lucky things that have happened to me since I started Indie Hackers. Patrick Collison, Stripe’s CEO, sent me an email with the subject line “Acquire Indie Hackers,” and my first thought was that he must be talking about some other Indie Hackers somewhere.

At the time, I was at a turning point with the site. I’d grown the revenue to close to $6,000/month, which was enough to cover the costs and pay my rent in San Francisco. That felt great! But I was making that money by selling ads, which felt like a never-ending treadmill that was taking up a ton of time every week, and the result of my efforts was actually making the site worse. I was in the midst of searching for a new business model when Patrick emailed me.

By the way, I do not recommend bootstrapping a company from an expensive city like San Francisco.

The first code I wrote after joining Stripe was to remove all the advertising from the site. Today, Indie Hackers makes $0. Otherwise, I didn’t change very much at all. Stripe’s strategic goals in acquiring Indie Hackers mirrored my own non-monetary goals in running it — to inspire more people to start businesses, and to help more of those businesses succeed.

How does Stripe measure the success of Indie Hackers? Conversions to using Stripe and Atlas? What are the current KPIs of Indie Hackers?

Indie Hackers is a total moonshot for Stripe. It needs to be a couple orders of magnitude larger than its current size to actually move the needle, and it needs to see similar improvements in how helpful and meaningful it is to entrepreneurs. In the future, it would be great if Indie Hackers was so useful that a substantial portion of new founders start there.

This is all very ambitious, so I’ve got my work cut out for me.

The most important metrics I track: How many people are starting companies because they were inspired by Indie Hackers? How many founders are making different decisions based on things they learned on Indie Hackers?

Of course these numbers are difficult to measure precisely. But the right targets are more important than easy measurements. I’d rather do a good job heading in the right direction than a great job going the wrong way.

You’ve grown your podcast to over 30k listens per episode. Props. What strategic and tactical advice do you have for others growing a podcast in the startup space?

What was it that Elon Musk said? “Running a podcast is like eating glass and staring into the abyss”? It was something like that. The podcast is really hard work for me. I want it to be great, but I’m never happy with it.

My advice? Find interesting guests, be consistent, do your homework, and prep good questions in advance. If you’re going to ask someone to take time out of their day to come on your show, you owe it to them to spend at least a few hours on research and brainstorming questions. You owe it to your listeners, too.

Take advantage of the fact that you’re producing recordings, not live performances. Don’t be afraid to edit and re-record things. Don’t be afraid to throw away bad episodes. You can avoid most of this work by being picky with your guests and preparing well.

As for growth, it helps if you have an audience. I doubt the Indie Hackers podcast would be getting so many downloads if I didn’t have a community and a mailing list to send it out to every week. Always be parlaying.

What does the Indie Hackers community look like long-term?

People can accomplish a lot when they help each other. The internet has obviously enabled us to collaborate on an unprecedented scale, but it still seems like most people working on their business ideas are toiling away all alone. Maybe it’s in our nature to be secretive about capitalistic pursuits, but I don’t think so.

My goal is for Indie Hackers to become the largest and most impactful community of entrepreneurs that exists. I want to get these people talking to each other.

I want successful founders to visit Indie Hackers to share their stories and learn from their peers. Aspiring and early-stage founders should come to learn from their role models, and to support each other in starting new businesses and overcoming specific challenges. Sometimes that’s as simple as asking for a second opinion on an engineering decision, or for feedback on a new design. Other times, it’s finding encouragement when things seem bleak and you’re on the verge of quitting.

Enlisting the aid of other founders in your journey to build a successful company should be a natural and obvious behavior.

In terms of solo founders and bootstrapped operations, what type of industry/product do you think it’s easier to make money online than say last year or even 5 years ago?

Almost all of them. There’s never before been so much high-quality information available to guide you through the process of making money online. It’s never been easier to connect with other people who are doing it. There’ve never been as many tools to help you build, and these tools have never been as powerful or affordable. And of course there have never been as many potential customers as there are now. Not only is the number of people online increasing, but so is their savviness. (My mom asked me a question about GitHub last week. I never imagined that would happen.)

Generally, the ethos in Startupland has been to raise a bunch of money, then attempt to dominate a winner-take-all market and become a unicorn. That’s not going away, but I suspect that targeting a niche and bootstrapping a business to $10–20k/month will become an increasingly attractive path to many founders.

Obviously, I’m big on community-building. It’s hard to imagine a world 10 years from now where people are less connected around the things they enjoy.

Also, education is always in demand. People learn in a myriad of ways, so you rarely see one particular teacher, institution, style, or company owning the market. That makes it great for new entrants. There are many millions of combinations of things you can teach and ways you can teach them.

In fact, building technically complex products is overrated. Simply finding people who need help and helping them is underrated. Indie Hackers started as a small collection of interviews. You couldn’t even call that a product.

What do you think tech blogs, like Hacker Noon, should be putting more priority toward?

I know a lot of entrepreneurs with a strong vision for the world who would do anything to build an audience to help make their vision happen. And I see a lot of publications that attract massive audiences, but don’t do anything beyond showing them ads.

It would be great to see blogs and content sites doing more to build communities, start movements, and experiment with other creative paths forward. Of course it’s risky to step outside your circle of competence, but you’ve built your own distribution platform, so you have a massive advantage when trying new things that most entrepreneurs can only dream of.

I think we’re all constrained in our thinking about what types of businesses can even exist, about what a media company is “supposed” to look like. We follow in the exact footsteps of the bigger companies that came before. But if instead of doing that, we repeatedly run an algorithm to use our existing advantages to build the next step toward a larger vision, we can end up in really interesting places and maybe create things that nobody’s ever seen before.

If you could change the approach and practice of entrepreneurship today, what would it be?

I’m trying to change it now, actually. Entrepreneurs shouldn’t be trying to do it all alone. Instead, they should spend more time opening up to their colleagues, teaching, learning, and asking for advice.

I find the barriers to doing this are largely psychological. Many founders — especially the more experienced ones — want to look like they know what they’re doing, like they’re crushing it and they have all the answers. Last year a friend told me his business was doing great, when I’d just heard from an employee that they were days from bankruptcy.

This is a ridiculous state of affairs.

The best CEOs all have mentors. None of us know everything, and we shouldn’t pretend we do.

But plenty of us know some things, so we can all help each other out. That’s why I’m building Indie Hackers. Go get some help, and try to offer some, too.

What advice do you have maker in front of their computer with startup idea right now?

Good advice is rarely one-size-fits-all. Understand who you are and where you’re at, so you know what advice to follow and what to ignore. For example, if you don’t want to raise money, stop reading blog posts written by venture capitalists.

One of the things I’m trying to do with Indie Hackers is to collect as many stories as possible about how people are turning their ideas and side projects into profitable businesses. The variety is astounding.

If you know 20, 50, or 100 stories about how people got started instead of just 1 or 2, then the chances are much higher that you’ll find an approach that resonates with you.

Keep up to date with Courtland Allen on Twitter & by visiting IndieHackers.com.