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#594 Annie Duke On Quitting & Bobby & Eddie Luckiest Moments in Music History

Bobbycast

Thursday, April 9, 2026 - 1 hour

Bobby sits down with Annie Duke to talk about luck, skill, decision-making, and why quitting is not always a bad thing. Annie explains how luck plays a bigger role in life than most people want to admit, why people judge decisions too much by the outcome, and how staying where you are is still a choice. Plus, Bobby and Eddie look at some of the luckiest moments in entertainment history, from Elvis at Sun Studio to Justin Bieber being discovered on YouTube, and the chance breaks that helped launch stars like Harrison Ford, Charlize Theron, Chris Pratt, and Matthew McConaughey. It’s a conversation about timing, opportunity, and the decisions that can change everything.

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