The Death of Shared Experiences | Bob Seawright on Sports, Family & Connection

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 valuableHow fandom forms across generations—and what it reveals about identityThe limits of Moneyball thinking in both markets and lifeThe difference between normal and extraordinary performance modelsWhy some systems reward optimization while others require breakthrough creativityPromotion and relegation, cultural accountability, and the flaws in American sports ownershipHow to think clearly in a world full of comforting delusionsBob’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.