Caroline Ellison, the second most important person who worked at FTX, was sentenced to prison this week. Nate and Maria talk about how she and Sam Bankman-Fried thought about making +EV bets (with other people’s money). They discuss her role – victim? villain? – and how she played out her real-life prisoner’s dilemma. Then, Nate gives an election update, and he and Maria discuss what people can do to influence the election in the final weeks. (Hint: It’s not donating to a presidential campaign.) Plus, Nate and Maria say farewell to two degenerate gamblers who passed away this week.

Further Reading:

Charity Navigator

More on Betsy Paluck’s research

Willy Nelson’s discography

Dana Carvey’s Biden impression from SNL

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Nate and Maria discuss Anna Sorokin’s (AKA Anna Delvey) spin on Dancing with the Stars. Then, they debate the merits and limits of voting in your self interest, and Nate explains why Nebraska has his attention on the election map.

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Kalshi, a company that offers prediction markets, sued the US government in an effort to legalize betting on elections. Nate and Maria discuss the pros and cons of election prediction markets. Plus, Nate gives an election update and Maria learns what to do when there’s no plus-EV move.

Further Reading:

Ready Your Bets: Election gambling is going mainstream in the US from Politico

Election Betting Halted After Appeals Court Agrees to Hit the Breaks from WSJ

Betting On Elections Can Tell Us A Lot. Why Is It Mostly Illegal? from the New Yorker

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Nate and Maria discuss the Harris-Trump debate. Then, Nate gives an update on his election model, and Maria shares the outcome of her irrational move at a poker tournament in Barcelona.

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Maria sits down with the great Brian Koppelman (Rounders, Billions, The Bear) to learn about how he navigates risk in Hollywood and beyond. They discuss his methods of determining when a risk is worth taking, how to offset risk with hard work, and the time he bet big on Billions.

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Nate and Maria briefly discuss the latest election news. Then Tim Harford, author and host of Cautionary Tales, joins to discuss two of history’s most compelling con artists: Sam Israel III and John Law. Risk-related lessons are learned.

Further Reading:

A Con Man Who Lives Between Truth and Fiction from the New York Times

The Murderer, The Boy King, and The Invention of Modern Finance from NPR (featuring our EP Jacob Goldstein!)

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This week Nate and Maria discuss the state of Kamala Harris’ presidential bid, including taking a look at her first policy proposals on price gouging and taxes on tips.

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Nate’s book “On the Edge” is out this week! (Get your copy here.) Maria interviews Nate about the origins of the book, what extreme risk takers get right and wrong, and the year Nate bet a million dollars on sports.

Check out the Risky Business YouTube channel here: https://www.youtube.com/@RiskyBusinessShow

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