Nate Silver’s 2024 bestseller On the Edge: Risking it All is a deep-dive into the philosophical and cultural underpinnings of our modern-day gambling-obsessed America. In nearly six hundred pages he examines everything from poker to cryptocurrency to AI, and presents an ontology that divides American elites into “The River” and “The Village”: risk-takers and risk-averse. Joining me to discuss it is the chess and poker player Jennifer Shahade, author of the new book Thinking Sideways: How to Think Like a Chess Player and Win at Life.
On the Edge with Jennifer Shahade
Probability and its discontents
May 25, 2026
Cross-posted by American Gambler
"New conversation with David Hill, where we discuss the overlap between Thinking Sideways and On the Edge, covering all sorts of great topics on the way, including: decision paralysis, fear of winning, and cracking down on cheating, in chess and in writing. "
American Gambler Book Club
Each week I invite friends and guests to discuss a gambling-themed book (however loosely-defined) and whatever else may come up. Writers, entertainers, bon vivants and other smart and interesting people help me figure out what all belongs in the canon of books about gamblers as I work on my own contribution to whatever that is. Presented by InGame.com.
Each week I invite friends and guests to discuss a gambling-themed book (however loosely-defined) and whatever else may come up. Writers, entertainers, bon vivants and other smart and interesting people help me figure out what all belongs in the canon of books about gamblers as I work on my own contribution to whatever that is. Presented by InGame.com. Listen on
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