John Moakley has spent decades building, running, and investing in data-driven companies—long before “data science” had a name. In this conversation, John joins Mike and Corey to pull back the curtain on what private equity really looks for, how companies often miss the value sitting right in front of them, and why the current hype around AI mirrors the early days of data monetization.

From turning a magazine subscription list into a revenue stream, to helping scale a $70M data business, to earning the nickname Dr. No inside a private equity firm, John shares lessons from both the operating and investing sides of the table.

This episode is about more than data. It’s about pattern recognition, strategic pivots, and the often-overlooked cultural cost of change. And yes, we finally go remote for the first time because when the guest is this good, we don’t let geography get in the way.