EP 477- Jennifer Shahade on Cheating, AI, and Thinking Like a Chess Player

Jennifer Shahade is a two-time U.S. Women’s Champion, poker professional, commentator, and acclaimed author. This week, she returns to the pod to discuss her new book Thinking Sideways: How to Think Like a Chess Player and Win at Life. Drawing on chess, poker, and psychology, Jen shares practical tips and memorable stories about decision-making, creativity, and improvement.

We discuss:

• Why she interviewed reformed chess cheaters and what their stories reveal about ambition

• Helpful advice for remembering opening lines

• The “Einstellung Effect” and how to avoid missing better ideas

• How AI is changing the way we learn and think

We also catch up on Jen’s recent travels and upcoming events. There is a lot to learn and plenty of great stories along the way.

0:00- Intro-

Jen Shahade and US Chess announce a settlement:

https://x.com/KenneyBaden/status/2039375140534767852?s=20

0:02- Jen Shahade joins me. How did she find reformed chess cheaters to interview? What did she learn from talking with them for her book?

Mentioned: Netflix Untold Documentary about the Niemann-Carlsen story 

https://www.netflix.com/title/81582391

0:10- What is “MTR”? 

0:14- Working with legendary trainer IM Mark Dvoretsky 

0:18- Lessons learned from interviewing a memory champion 

Mentioned: Yanjaa Wintersoul, GM Sam Shankland 

0:28- Jen’s experiences coding with Claude 

Check out the links to the app she built here:

https://jenshahade.substack.com/p/spin-the-wheel-vibe-a-move

0:36- What is “the Einstellung effect”? 

0:40- Jen’s chess-related conversation with legendary psychologist and author Daniel Kahneman 

0:42- How chess master and Alpha Zero creator Demis Hassabas “thought sideways” to secure funding for his start up. 

0:48- Observations from the recent Sloan sports analytic conference

0:50- What is “the sandwich method”?

0:51- Upcoming book events for Jen

0:52- If you will be in NYC on May 12 and want to support a good cause, come see Jen and I at this event.

You can buy tickets to the Chess in the Schools Poker/Chess Fundraiser here:

https://secure.givelively.org/event/chess-in-the-schools-inc/chess-in-the-schools-3rd-annual-charity-poker-tournament

 0:54- Thanks to Jen for joining me again, here is where to order her book.

https://www.simonandschuster.com/books/Thinking-Sideways/Jennifer-Shahade/9798897100729

https://www.amazon.com/Thinking-Sideways-Think-Chess-Player/dp/B0FCDDB8XV 

Photo in thumbnail by Maria Emelianova

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