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:

https://www.j-archive.com/showseason.php?season=42

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:

https://www.instagram.com/gregshahade/?hl=en

X: 

https://x.com/GregShahade

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