From Apps to Business: Finding My Post-Exit Calling

I’ve recently read Bill Gurley’s Runnin’ Down A Dream. The book’s main argument is that most people are stuck in a career they don’t love. How do you quickly identify that you are? Bill asks you to imagine yourself doing the same thing in 30 years. If that doesn’t excite you, you probably aren’t in the right place.

What is the right place? Gurley puts a spin on the wisdom of “follow your passion”. The spin is “follow your fascination”. While it might initially seem like splitting hairs, the reason for this distinction is that to rise to the top and have a successful career, you need to be a learning machine. It’s not enough to have a passion for something; you need to be so fascinated by it that you read the history, the biographies, you study the footnotes for clues, plan vacations around it, and you do that for years and years.

A personal counter-example is my passion for playing chess, but I am lacking the fascination part. I’m not trying to go super deep into every crevice. I haven’t memorized the bishop and knight checkmate. But boy, do I like to play chess. Unfortunately, I am missing the fascination and the deep learning that compounds through the years, helping you achieve staying power in your chosen area. Using Bill’s filter, I know chess shouldn’t be a career for me.

Bill also dispenses other advice, such as seeking out and landing mentors. He also talks about finding your peers and even moving to where the action is. All important ingredients many successful people share.

As some of you know, four years ago I sold most of JRT Studio’s app portfolio. I spent 11 years immersed in Android apps and loved it. It was a fascination, and I absorbed myself in it. I have no regrets for those 11 years, and I am also grateful to have gotten an exit. The Android apps had me in golden handcuffs. When anything broke, or Google said jump, it was all hands on deck. And Google’s sword of Damocles hung over me all 11 years, even swung and nicked me in 2014. Living with that sword above my head was exhausting.

Selling the Android apps gave me a few years’ earnings all at once. My wife and I decided that there would be no celebrations, no lavish purchases. In fact, we tightened our belt because what we wanted to purchase was freedom, and that we have (so far). Freedom has been great. I’ve followed several interesting areas, I’ve built AI models, websites, read books, been amazed by Claude Code, listened to earnings calls, and generally enjoyed myself.

But circling back to Runnin’ Down A Dream, I ask myself, “What is my fascination?” The answer to that is business, and it isn’t close. Maybe that was part of the JRT Studio story all along. I have no business education, but I got an exciting crash course by running and building one. The early days were absolutely thrilling, but as time passed, the learnings within JRT Studio grew more and more stale.

What to do with the fascination with business? Unfortunately, Bill can’t answer this one for me. Long before reading his book, I’d tried reaching out to some famous investors. For instance, I offered to work for Mohnish Pabrai for free. He lives a few miles from me, and I’ve even seen him at my grocery store (but I didn’t bother him). Whatever question I would have had for Pabrai would most likely have been about whatever I was trying to learn about at that moment. Whether it was coal companies or car dealerships that particular day, I don’t know.

The book got me thinking, and I came back to this Substack. I believe this is a great outlet for my fascination. However, I don’t feel that I want to limit this Substack to “fintechs with a market cap under $1B” just yet. My motivation to publish is to share what I find fascinating, meet peers, find mentors, maybe find a job, and be more social than reading books.

And while not a physical location, this is where other people fascinated by business are hanging out. Whether it’s talking about labor rights, or writing about how exponentials are impacting society, Substack seems like a great place to be.

So that’s what I am going to do. While I am not much of a writer, I’m going to use this space to write about business and engage with the community.