Unpacking Everything I’ve Learned (and Unlearned) About Entrepreneurship

I’ve had a bit of a wild ride through startups. I’ve helped build companies from a napkin to $10m+ in revenue, been around the table for acquisitions, and been solely responsible for the failure of a once-promising adtech company. I’m naturally curious, and I like unpacking what worked, what didn’t, and what I think differently about now.

A lot of that comes down to the practical stuff: AI and how companies get discovered through it, go-to-market, digital discovery, customer acquisition, and getting those first couple hundred customers or users. I’ve worked across SEO, ASO, e-commerce, sales, media, and startup operations, so I tend to talk about the work as it actually felt while it was happening.

One framework that came out of my own failure, and out of studying comparable stories, is The Patterns of Startup Failure. It looks at six ways founders get in their own way: Identity, Distraction, Vanity, Fear, Hubris, and Isolation. They usually show up together, which is where the conversation gets interesting.

I most often join trade conferences and university classrooms, in person or virtually. I like the room more than the podium: guest lectures, fireside conversations, discussions built around a case, and Q&A that goes wherever the audience wants to take it. Sessions typically run 45 to 90 minutes.