In this episode, we’re joined by writer, thinker, and Substack author Bob Seawright for a wide-ranging and deeply human conversation about what sports, fandom, and Moneyball can teach us about markets, behavior, and decision-making.

We explore why live shared experiences matter, how fandom evolves across generations, and where investors misunderstand data-driven models like Moneyball. Bob also shares personal stories about his family, his love for soccer, and the nuanced differences between playing a “loser’s game” and a “winner’s game”—in sports, investing, and life.

Topics covered include:

• Why shared live experiences like sports are increasingly rare and valuable

• How fandom forms across generations—and what it reveals about identity

• The limits of Moneyball thinking in both markets and life

• The difference between normal and extraordinary performance models

• Why some systems reward optimization while others require breakthrough creativity

• Promotion and relegation, cultural accountability, and the flaws in American sports ownership

• How to think clearly in a world full of comforting delusions

Bob’s blend of insight, humor, and storytelling makes this a must-listen for anyone who cares about markets, meaning, and the messy beauty of being human.