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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Maria sits down with Bill Perkins, the legendary energy trader, to talk about his approach to risk in business, poker, and life.

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Nate’s election model is back on, and it’s in Kamala Mode. Nate and Maria discuss what the model shows us about Kamala Harris’ chances, and the strange election misinformation that has been going around. Then, they are joined by World Series of Poker Main Event winner Jonathan Tamayo to discuss his win – and the controversy that surrounds it. 

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Biden’s out of the race! Matt Glassman joins Nate to talk about what the consolidation behind Kamala Harris reveals about party politics and who she might pick for a running mate.

Further Reading:

Why Biden Finally Quit from Politico

Can Harris Beat Trump? from New York Magazine

What a Kamala Harris Presidency Might Look Like from Semafor

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Nate and Maria discuss the assassination attempt on Donald Trump and the psychology of conspiracy theorists. They talk about what Trump’s selection of J.D. Vance means for the election. And they parse the latest in the Democrats’ intra-party fight over Biden.

Also on the show: Nate’s day at jury duty is a case study in bad bluffs.

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