Bootstrapping a Business as a Single Founder

There's something magical about building a business as a solo founder. Personally, I love the idea of being totally self-sufficient and having something to call my own.

I'm not alone here — I looked at the numbers for the interviews I've done so far, and being a single founder is by far the most popular choice. Out of the 61 businesses I've interviewed, 49 are run by single founders, and only 12 have multiple founders.

Additionally, the path of the single founder is also the most inspiring to read about. Out of the top 10 most popular interviews I've done, 9 were with single founders. Mike Carson of park.io is perhaps the best example:

This is the most popular tweet I've ever sent from @IndieHackers.

Despite all of this, the fact is that running a business on your own is hard. Don't believe me? Here are a couple more statistics from all of the Indie Hackers interviews I've done since launch:

The median solo founder revenue is $2,000 per month.
The median multi founder revenue is $17,400 per month.

Whoa. 😯

I know there are plenty of plausible explanations for that humongous revenue gap that aren't necessarily, "Doing it on your own is harder." But still — it's clearly difficult, and that's something I can personally attest to.

Like many of the founders I've interviewed, I've been running Indie Hackers solo these past few months since launching. I'm a long way away from having it all figured out, but I'd like to share what I see as the biggest obstacles for single founders, and talk about my approaches for overcoming them.

The Power of a Good Sounding Board

Why don't we start on a high note? There's one huge advantage to running a business as a single founder, and that's the total lack of communication overhead and its associated costs. Assuming you're a sane individual, you can't exactly waste time talking to cofounders you don't have. That means there's no opportunity for confusion or disagreement.

But of course there's a downside: You lose your sounding board. There's nobody there to bounce your ideas off of. Nobody to give you feedback, to tell you when you're being crazy, or when you've missed something simple. Elliott Garms of HumanPredictions has his own solution for this:

Personally, I'm really into mentors. I love finding people who have been successful on their own and getting advice from them. Not only do mentors give great advice, but many become fans of what you're working on and go out of their way to help you. Find mentors, buy them coffee/beer/whatever, and get their advice and help.

With Indie Hackers, I try to treat all of you guys like my mentors. I spend a lot of time on Twitter, on the forum, and in my weekly newsletter talking about my plans and asking for feedback. As a result, I've gotten help with everything from optimizing conversion rates to choosing a business model.

For example, even though we'd never met before, I spent an hour on the phone with growth expert Julian Shapiro a couple weeks ago, and he gave me some tips that've nearly doubled the signup rate for my newsletter. And on the forum, marketing expert Annette Wong gave me some great advice that's helped me grow my Twitter audience a lot easier.

I never feel alone in making tough decisions, so it's safe to say this approach is going really well for me. I think there are three keys to making it work:

Be personal and vulnerable. I almost always use "I", "me", and "Courtland" when talking about Indie Hackers, because people want to help other people, not faceless companies.
Be transparent. I'm totally open about my plans, revenue, growth stats, tech, etc. It would be a lot more difficult for people to help me if I didn't embrace transparency.
Engage! Reach out and talk to people on Twitter. Share your business in the Indie Hackers forum. You can't expect to get feedback unless you ask for it a lot!

Lots of people ask each other for feedback on the Indie Hackers forum.

How Constraints Help You Focus

One thing you see often with big, well-funded businesses is a lack of focus. When a business has tons of money and employees, then it lacks constraints, and it trends toward becoming an amorphous blob that's striking out in every direction.

As a solo founder, however, you have plenty of constraints, especially if you're bootstrapping. Having no money and no manpower severely limits what you're able to do. You just can't afford to branch out too far, which is a blessing, because it means you stay focused.

That said, it's not impossible to get off track. I've had more than a few people who I deeply respect tell me that I should shut down the forum, delete the blog, and spend 100% of my time on the interviews and newsletter. As you can tell by the fact that you're reading this, I don't take all the advice I'm given. 😇

I'll talk about why in a future post, but I think the current trifecta (interviews + blog + forum) is worth a lot more than the sum of its parts. Am I stretching myself thin and losing focus? I'm honestly not sure at the moment. Time will tell. But that brings me to my next point.

Beware of Treading Water

Mike Taber has an excellent post about the biggest threat to your bootstrapped business. In it he writes:

As your business becomes successful, you end up doing a lot of work that is what I like to call "business overhead". It's the work that needs to be done to keep the business running, but none of it moves the business forward... You're doing nothing more than treading water. But it feels like you're working on the business. Let me be clear about something here. You're not. The work is necessary. But it's not important... It's a subtle distinction, but it's an important one. If your business can't live without you, then you haven't created a business. You've created a job. And that's probably not what you want.

This might sound all-too-familiar to those of you running businesses of your own. It's especially relevant if you're a single founder.

The fact is, there will always be hundreds of tasks pulling you in different directions. If you ignore them, then you'll be neglecting some crucial part of your business. But if you attend to every little task as it comes up, then the constant switching between activities will kill your productivity.

For example, at any given time with Indie Hackers I have interviews that I need to edit and publish, comemnts on the forum to reply to, emails to answer, tweets to respond to, blog posts to write, newsletters to send, features to add, fixes to make, copy to change, tests to run, data to analyze, etc. This list is just the tip of a very large iceberg, so I'm sure it's easy for you to imagine how I run the risk of spreading myself thin and getting nothing done at all.

I suspect that the ideal, long-term solution to my problem is automation. For example, Chris Chen's photo-to-painting marketplace, Instapainting, is entirely automated, as is Mike Carson's domain backorders business, park.io:

I have so many automated processes running now that I feel like I have a team of 50 employees working around the clock, constantly and accurately, always in the background. park.io is set to break over $1M in revenue this year and I am the only employee, but only because I am able to leverage all of the automated processes that are able to do the work for me.

Currently, very little of what I do for Indie Hackers is automated, and none of it is outsourced or crowdsourced. This is an area where I plan to (and need to) improve, probably gradually over time.

It's a tough problem to tackle, however, because most of what I do is content-related. I'll probably always have to edit interviews, send tweets, and write blog posts myself, although there are definitely ways that I can streamline the process.

How to Stay Motivated and Ship

Inevitably there will be days where you get down, and working together with others can really help you keep a positive mental state. In my opinion, this isn't talked about enough.

I'm lucky enough to have a really good support network around me. When I started Indie Hackers I was living with my brother and a friend, both of whom worked from home alongside me. And about I month ago I moved in with my girlfriend, who also works from home. They're constantly propping me up, as are all the positive tweets and emails I receive from you guys:

I know that I wouldn't be nearly as healthy and optimistic about what I'm doing if I didn't get this kind of support. It's totally worth it to find people in your lives (or communities online) who you can talk to about what you're working on. Ignore the haters, and stay in touch with your supporters.

Another thing that really keeps me going is my weekly newsletter. Every Thursday morning I email all my subscribers (there are over 3,000 of you now!) about the new interviews I've added and other changes I've made to the site. I never want to send a mediocre newsletter, and I actually get really nervous about it, so I spend every week working hard to make sure I've got new and interesting content to include.

It reminds me of doing Y Combinator back in 2011 and having weekly office hours with the partners there. Nobody wants to look bad in front of people they respect, so I would work my ass off to get as much done as I could. Having some sort of regular "accountability event" is a really good hack for staying motivated and making yourself unusually productive.

Goals

Overall, things aren't too bad! I'm really hoping that I'll be able to write about this topic again in a few months and report back with more insights and better solutions than the ones I have now. 👍

Between now and then, I'd really like to start automating more processes, so I can free up time to focus on important things like growth and marketing. I want to start tracking my time on an hourly basis, so I can actually measure whether or not I'm spending time on the important parts of my business. And I want to source interviews more efficiently and get ahead of schedule, so I don't feel stressed about trying to come up with 4 every week.

In the meantime, I'll keep you updated with how things are going via my newsletter, so subscribe if you'd like to hear more.

And if you have any tips/suggestions, or if you're working on a business of your own and would like some feedback, I'd love to hear from you on the forum!