I was interviewed about entrepreneurship

A few months ago Michael Carruthers asked if I'd like to do an interview for his podcast, Imperfect Creatives. We talked about my time as a solo entrepreneur and my general thoughts on that whole space (I have a few opinions). I especially enjoyed doing this interview because it's really hard to break through the noise when you're writing about such a broad topic. If I write a technical article, I just post it in the Clojure community and it's easy to have good discussions. Post an article to Hacker News about your startup journey, and well... there are a lot of those. So hopefully you'll find some fresh takes in this interview.

Listen on Spotify | Listen on Apple Podcasts

Michael's site has a better description of the episode than I could probably write, as well as links to resources:

”Recovering Entrepreneur” Jacob O’Bryant on Building Products Full-Time, Why He Got a Job Again, and Invention as a Career Path

What happens when you chase your entrepreneurial dream for four and a half years and then realize it’s not actually what you want?

In this episode, I sit down with Jacob O’Bryant, creator of The Sample (now Yakread), to talk about his journey from quitting his job in his early twenties to going all-in on building his own products, only to discover that entrepreneurship wasn’t the path he thought it would be. Jacob is refreshingly honest about the psychological toll, the gradual realization that he valued invention over business-building, and why going back to a full-time job wasn’t defeat, it was clarity.

We also explore the framework that sits between pure research and entrepreneurship: invention. It’s a way of thinking about your work that doesn’t require monetization or academic rigor, just meaningful exploration. Plus, we dig into unbundling social media: what it means, why it matters, and practical steps you can take as an everyday person to support a more open internet. If you’ve ever wondered whether the “quit your job and start a company” narrative is really for you, this conversation might give you a different perspective.

We also had a nice conversation about Biff right after we stopped recording.