A fortuitous decade as an indie software developer

A fortuitous decade as an indie software developer

August 10 2026

Ten years and one day ago, on August 9, 2016, I abruptly quit my job. I mark this occasion as the beginning of my indie software developer career. Happy anniversary to me and to my customers!

I didn’t formulate a plan until after I quit. I decided that I could afford to indulge a dream, express myself, design and build my own app from scratch. I could be my own boss for once. My journey as an indie developer mirrored an enduring aphorism: it takes five years to become an overnight success. That night was September 19, 2021. At the time, I was about a month away from going broke, having burned through all of the savings I had accumulated before I quit my job. On the morning of September 20, however, Apple released iOS version 15, which added web browser extensions for mobile Safari. This deus ex machina, a miraculous software update, changed my career, and my life. Suddenly I was running a viable business. Since then I’ve rebuilt my savings to a level higher than before. Don’t worry, though, I’m not retirement planning. On the contrary, I’m a weirdo workaholic who gets bored without a purpose.

My inclination is to refrain from giving business advice, because it would consist largely of survivorship bias. I got lucky, eventually. For five years, I struggled. I failed financially. It was demoralizing, depressing. I felt hopeless. The only thing that kept me in business was my inability to find a new job. It turns out that the industry is not especially interested in hiring a long-experienced software engineer, at least not if that software engineer is middled-aged, lacks a computer science degree (my two philosophy degrees are apparently unimpressive), and possesses outmoded skills such as native Mac app development with AppKit and Objective-C. I had a number of job interviews but no offers. The last time I received an offer of full-time permanent employment was in 2008. Perhaps I wouldn’t have quit that job if I had known it would be my last. Oh well, ignorance is bliss! So who am I to advise others on their careers?

My first app as an indie developer was Underpass, the eponym of my business website underpassapp.com. Underpass provided peer-to-peer, end-to-end encrypted chat and file transfer. You might ask, reasonably, what business a lone developer had building a chat app. In retrospect, I had no business at all. Nonetheless, my inspiration was a personal use case, transferring sensitive data between my own devices. I released Underpass for Mac in January 2017 and Underpass for iOS in April 2017. Sadly, Underpass was a flop, its lifetime revenue under $3000. I finally removed Underpass from the App Store in 2021, because Apple kept breaking features in OS updates and customers kept requesting features that I was never going to implement. The minuscule App Store revenue was insufficient to justify ongoing maintenance of the app. Underpass still mostly works, though, and to this day I still use Underpass myself for its original use case, transferring data and files between my own devices. (I’m not a fan of cloud sync and refuse to sign my iPhone into iCloud.)

You might also reasonably ask why a vehement critic of the App Store decided to distribute software exclusively from the App Store. I had two main reasons, one fairly obvious, the other I was reluctant to share but feel comfortable admitting now. The obvious reason is that an iOS version of Underpass was essential to my vision for the app, and the App Store was the only way to distribute software on iOS, unfortunately. The other reason is that I had no confidence my software business would succeed. I figured that I would give indie development a try, make my own app, and if my business happened to fail, I could put my App Store app on my résumé for potential employers to see when I applied for jobs. (Of course I’ve already noted how this strategy was fruitless.) The prospect of low sales and wasted effort deterred me from developing my own independent store outside the Mac App Store. Such an investment can pay off for longtime indie Mac developers, but I was far from certain that I would become one.

My second app was StopTheMadness, a Safari extension. I don’t think I’ve ever mentioned this anecdote, but I was inspired to create the app by an offhand tweet from Tom Harrington (no longer on Twitter) complaining about some website annoyance. Thank you, Tom! I developed StopTheMadness very quickly, and after its release in April 2018, StopTheMadness became somewhat popular very quickly, popular enough to be promising. The problem was, StopTheMadness did not achieve enough popularity to pay for all of my living expenses, so I was still depleting my savings. Unbeknownst to me, the next three years of StopTheMadness, the difficult years, were setting the stage for my moment in the spotlight. I continued to improve the app, added many...