Nate Silver on the Art of Risking Everything

Honestly with Bari Weiss

Most humans are cautious by nature. We naturally like to do what’s comfortable and safe. But comfortable and safe don’t usually lead to. . . well, success. In fact, the most successful people in the world share something in common: They love risk.

That’s true of the best poker players, hedge fund managers, venture capitalists, and crypto traders. All of these people consider statistics; they embrace uncertainty; and they make bold predictions that ultimately pay off for themselves—and sometimes for humanity.

How do they do it?

Our guest today, Nate Silver, has a theory on what drives successful people, how they think, and how they achieve enormous success—or, at times, catastrophic failure.

He just wrote an entire book about it. On the Edge: The Art of Risking Everything analyzes these types of people and the principles that guide their risky decision-making—which, he argues, is key to understanding what drives technology and the global economy.

Nate, one of the most sophisticated thinkers on risk and uncertainty, is a statistician, sports analyst, professional poker player, and the founder of FiveThirtyEight, a website that revolutionized political reporting with its data-driven election predictions.

Today, Nate discusses why it’s important to take more risks, and how he sees the current election playing out.

If you hear statistics and data and probability and analytics and roll your eyes, we get it. But this is a conversation that goes beyond all that. Nate explains what frustrates him about his critics, why he is happy to no longer be affiliated with FiveThirtyEight, and how his biggest passion—poker—helped him become one of the world’s most famous prognosticators.

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