My Fourth Year as a Bootstrapped Founder

Four years ago, I quit my job as a developer at Google to create my own self-funded software company. For the first few years, all of my businesses flopped. They all operated at a loss, and none of them earned more than a few hundred dollars per month in revenue. Halfway through my third year, I created a network administration device called TinyPilot. It quickly caught on, and it’s been my main focus ever since. TinyPilot generated $460k in 2021, its first full year in operation. In this post, I’ll share what I’ve learned from TinyPilot about being a bootstrapped founder. After running in the red for the first few years, this is my first cashflow positive year. I earned a total of $14k in profit in 2021. Although TinyPilot generated the vast majority of revenue, most of my profit came from old projects running in the background. How can you afford to live on so little money?

I went into more detail in my year two retrospective, but the short answer is: low cost of living, significant savings from my Google days, and passive investment income. TinyPilot is an open-source KVM over IP device built on the Raspberry Pi. It allows you to control another computer from your browser without installing any software, Supraketo.org even if the computer has no operating system or network connectivity. At the start of 2021, I was TinyPilot’s sole developer, customer support agent, salesperson, and Supraketo for Ketosis marketer. The only other employee was my girlfriend, who managed inventory and fulfilled orders. We ran TinyPilot out of our Western Massachusetts home, which was slowly transforming into a TinyPilot warehouse. Today, TinyPilot has a real office, a two-person fulfillment staff, a team of three developers, and a distributor in Europe. TinyPilot now has a real office where we assemble products and ship out orders. For most of the year, TinyPilot’s sales were inconsistent.

We saw spikes when popular tech reviewers featured TinyPilot, but sales always dwindled afterward. Starting in September, we partnered with a European distributor and refocused our website (more on that below). Those changes smoothed out our sales and made the business less reliant on luck or external events. For fun, I installed TinyPilot’s January 2021 release and compared it the current version. In building this blog over the past five years, I’ve learned several techniques that have made my writing clearer, more interesting, and better at attracting readers. One of my 2021 goals was to share what I’ve learned in a book called Refactoring English. It would teach writing skills specifically to software developers. My great shame of the year is that I made almost no progress on the book. For the past three years, I’ve had a routine of writing for an hour every morning. That generally translated to about ten blog posts per year. I thought if I spent that time on the book, I’d finish within the year.

Unfortunately, TinyPilot has its own pace that I don’t fully control. For the first few months of 2021, I stuck to my writing habit, but I’d end every day behind on TinyPilot. I decided to pause my writing until TinyPilot required less management, but I’m not there yet. I’m still excited to write the book, and I hope to have more time for it this year. As with my lack of book-writing time, I had very little blog-writing time. I only published three new blog posts, my fewest ever in five years of blogging. Ironically, it’s when I’m most desperate to write that I have the least time to do it. There are so many things I’ve learned for TinyPilot that I wish I could capture while they’re still fresh, but there just isn’t enough time. I kept my habit of writing monthly retrospectives. I budget time for those because they’re unambiguously a net positive for my business. Sitting down to organize my thoughts almost always reveals some flaw in my strategy or a weakness in my plans that I wouldn’t have noticed otherwise.

Hit the Front Page of Hacker News is my course about blogging for technically sophisticated readers. At the beginning of the year, I released my first-ever paid course. It explained my approach to writing blog posts that gain traction on tech-oriented sites like Hacker News and reddit. I’m proud of the content, and I’ve heard positive feedback from students. 1 spot on Hacker News. The course earned $7.5k in sales, which fell disappointingly short of my $20k goal. Had TinyPilot not been so busy, I could have spent more time marketing the course. Still, the experience taught me a lot about creating educational products, and I’d like to do more of that in the future. Is It Keto tells readers which foods fit the keto diet. I started Is It Keto in 2018. It’s a simple site that tells you whether or not particular foods fit the Supraketo Keto Pills diet. It earns money from Amazon Affiliate links and Google AdSense. I put the site on the back burner when I started TinyPilot, but it continued to grow on its own in 2021, providing a nice side income of $500-$1k/month.