EP 481- IM Greg Shahade: Inside His Incredible Jeopardy Run

IM Greg Shahade has long been well known in the chess world as a three-time national scholastic champion and the founder of the Pro Chess League and the US Chess School. Recently, however, he reached a much broader audience with an impressive run on the syndicated trivia show Jeopardy!. Greg amassed over $75,000 in winnings, dethroning 31-time champion Jamie Ding along the way. He joined me after what he described as “the craziest week of his life” to discuss: The approach to adult learning that helped him go from trivia novice to Jeopardy! champion in just a few years Behind-the-scenes insights from the recording process, plus his reflections on his controversial on-stage mannerisms How his background in chess (and poker) shaped his strategy and decision-making under pressure There isn’t a ton of chess discussion in this episode, but Greg’s approach to learning and performance has clear applications across many domains. 00:00 Introduction Check out our sponsors, Chessiverse.com , and you can use code Perpetual30 to save 30% on premium feature and/or IM John Bartholomew’s Complete Scandinavian Course. Chessiverse.com 03:00- Greg Shahade joins the show, we begin by discussing adult learning and Greg’s late start to trivia. Mentioned: Learned League Thinking Sideways by Jennifer Shahade Ducksters 07:43 Building Knowledge Structures 10:03 The Role of Intense Study 12:54 Flashcards and Review Techniques 15:43 Betting Strategies on Jeopardy 18:45 Reflections on the Jeopardy Experience You can review questions Greg faced here: 25:00- Patreon mailbag question- Why does Greg know so little about current events? What is his approach to daily double hunting? 30:44 Daily Double Strategies and Insights 36:57 Patreon mailbag question- Why is Greg so expressive when playing Jeopardy? 42:16 Physicality and Focus in Jeopardy 49:25 Behind the Scenes of Jeopardy 52:40 Facing the Champion: Mental Strategies 55:11 The Weight of Anticipation: Media and Public Perception 57:02 Navigating Fame: Love, Hate, and Public Reaction 59:50 Preparing for the Tournament of Champions 01:03:51 Chess and Jeopardy: Cross-Disciplinary Insights 01:07:20 Reflections on Study Techniques and Memory 01:11:20 Final Thoughts: The Game and Its Emotional Toll Thanks to Greg for joining me at a busy time. Follow him here: Instagram: X: Learn more about your ad choices. Visit podcastchoices.com/adchoices

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EP 481- IM Greg Shahade: Inside His Incredible Jeopardy Run is an episode from Perpetual Chess Podcast by Perpetual Chess LLC .

This episode is 80:56 long.

This episode was published on May 5, 2026.

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