Taylor Lorenz’s Power User
Taylor Lorenz’s Power User

Why Timothée Chalamet Is Shilling Kalshi: Inside The Plan To Monetize Everything

June 17, 2026

AI Summary

5 min read

Why Timothée Chalamet Is Shilling Kalshi: Inside The Plan To Monetize Everything

Taylor Lorenz’s Power User

There is literally a market on what color Donald Trump’s tie will be tomorrow during his Oval Office appearance. What’s the value there? How is this benefiting society? That’s the question Taylor Lorenz and NPR reporter Bobby Allen grapple with in this episode, which traces how prediction markets—once a niche regulatory experiment—have become an inescapable force in sports, media, politics, and celebrity culture.

From Goldman Sachs to the Golden Goose

The story of Kalshi begins with its CEO, Tarek Mansour, a former Goldman Sachs trader who noticed something strange ahead of the 2016 election. Investors kept calling the trading desk asking how they could bet on or against Trump winning. Mansour discovered there was no direct way to do it—you could short the stock market or execute complicated currency swaps, but not simply put money on a political outcome. That was his "aha moment."

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What you'll learn

  • 1 (02:30) **Kalshi's explosive visibility** - Discussion opens with the flood of Kalshi ads and Timothée Chalamet’s recent post
  • 2 (03:19) **Guest introduction** - Bobby Allen of NPR joins to explain the prediction-market boom
  • 3 (03:47) **Founding story of Kalshi** - Tariq Mansoor’s Goldman background and motivation to create direct event betting
  • 4 (05:00) **Early regulatory battles** - Kalshi’s struggle for approval versus the “move fast” approach taken by competitors
  • 5 (06:08) **Polymarket’s rise** - Shane’s crypto-native, offshore strategy and its early traction
  • 6 (07:48) **Kalshi’s 2023–2024 pivot** - Shift from niche commodities markets to high-profile political contracts
  • 7 (08:58) **Lawsuit against the CFTC** - Kalshi sues its regulator and wins the right to host election markets

+ Full timestamped outline available in the app

Guests on this episode

Taylor Lorenz Bobby Allen

Show Notes

Why is Kalshi suddenly everywhere? 

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Prediction markets like Kalshi and Polymarket have become one of the most powerful forces in American media, politics, and culture. In this episode of Power User, I sit down with NPR's Bobby Allyn, the country's top prediction-markets reporter, to break down how Kalshi went from a tiny startup that 50 lawyers refused to represent to an inescapable cultural juggernaut backed by the Trump family, celebrities, and major news organizations.

We dig into how Kalshi exploited a legal loophole to bring sports betting and election betting to every state, why Donald Trump Jr. became an advisor to both Kalshi and Polymarket, and how the companies called the 2024 election for Trump before the mainstream media would, cementing their place in the MAGA universe. Bobby explains the rise of Kalshi CEO Tarek Mansour, Polymarket's offshore "crypto bad boy" founder Shane Coplan, and the regulatory war happening right now inside the CFTC.

We also cover the dark side nobody is talking about: undisclosed influencer marketing flooding your feed, the Timothée Chalamet Kalshi deal, secret ads during the NBA playoffs, the Mr. Beast video editor insider trading scandal, betting markets on wildfires and war, and the casinoification of the entire economy. We dig into the lawsuits, the looming Supreme Court showdown, and whether this whole gambling empire could vanish overnight! 

We cover:

  • How Kalshi went from a rejected idea to a multi-billion dollar empire.

  • The shocking court ruling that changed everything in 2024.

  • Why MAGA influencers embraced prediction markets early.

  • The Mr. Beast video editor insider trading scandal.

  • How sports gambling bans were bypassed with a loophole.

  • Timothée Chalamet's controversial Kalshi ad.

  • The media's role in normalizing this "gambling for everything".

  • Why Democrats and Republicans are fighting over regulation.

  • The lawsuits that could end Kalshi.

  • What happens when you can bet on wildfires, wars, and more.


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