I recently joined John Stanton, Founding Partner and Managing Director of Trilogy Equity Partners, on the CLOUDBREAK podcast. John has been a mentor to me for many years. Trilogy has also backed Kiril Savino and me twice: first at GameChanger and now at Rollout.

In the episode, we talk about how I went from minor league baseball to founding GameChanger, and what I learned along the way. That includes meeting Kiril, hearing "no" from hundreds of investors, and working through the structural challenges every youth sports business faces: fragmentation, seasonality and churn.

We then turn to Rollout. I explain how a cold LinkedIn message from a deputy police chief, followed by ride-alongs with patrol officers, showed us how much of an officer's shift goes to paperwork. That became the starting point for the company. John and I also discuss building products with AI, staying close to customers, and why understanding the problem has to come before building the solution.

We close with the people who have shaped us, including our shared admiration for Nextel co-founder Morgan O'Brien.

Thank you to John and the CLOUDBREAK team for having me.

Listen to the full episode on Spotify →