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America’s Secret Technofacist Overlord, with Max Chafkin

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Nov 19, 2025

Guest

Max Chafkin

Max Chafkin, a Bloomberg Businessweek reporter and author of 'The Contrarian', dives deep into the enigmatic world of Peter Thiel, a powerful Silicon Valley figure. They explore Thiel's secretive rise, from funding Facebook to influencing political landscapes. Chafkin reveals Thiel's unique blend of libertarian ideology, his controversial funding of Hulk Hogan's lawsuit against Gawker, and his ambitions for a future beyond democracy. The conversation also touches on the surveillance implications of Thiel's Palantir and his desire for regulation-free zones.

01:18:03

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INSIGHT

Hidden Power Behind Tech And Politics

Peter Thiel is a powerful but secretive tech investor who shaped major companies and political figures.
His control extends across tech firms, Palantir, Anduril, and placements in government.

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ANECDOTE

Secret Funding That Toppled Gawker

Thiel secretly funded Hulk Hogan's lawsuit that bankrupted Gawker after they published about his sexuality.
That victory became a conservative rallying card and boosted Thiel's public standing.

insights

INSIGHT

Tech Exceptionalism As An Ideology

Thiel believes tech founders should operate with minimal restraints because rapid technological change equals progress.
That ideology merged with libertarian and Ayn Rand influences to shape Silicon Valley norms.

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Peter Thiel’s Background and Rise in Tech

04:14 • 2min

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Thiel as a Shadowy Puppet Master

06:44 • 56sec

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The Gawker Payback: Funding Hulk Hogan’s Lawsuit

07:40 • 2min

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Thiel’s Ideology: Tech Supremacy and Libertarian Roots

09:39 • 2min

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PayPal Origins and the PayPal Mafia Playbook

11:38 • 4min

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Tech Scaling by Ignoring Rules: From Facebook to Uber

Thiel’s South African Childhood and Political Grievances

28:56 • 6min

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Coded Racism, Gender, and the Tech Inner Circle

35:16 • 4min

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Public vs. Private Power: Thiel Compared to Musk

39:00 • 13min

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What Palantir Does and Surveillance Concerns

51:52 • 7min

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Branding Fear: Selling Powerful Tools to the State

58:46 • 3min

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AI Hype vs. Real Harms

01:01:25 • 3min

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Thiel’s Christianity and Grievance Politics

01:04:07 • 5min

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Seasteading and the Desire to Escape Regulation

01:09:12 • 5min

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Thiel’s Rejection of Democracy and Authoritarian Tendencies

01:13:51 • 5min

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How Much Power Does Thiel Actually Hold?

01:19:08 • 4min

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Thiel’s Weaknesses: Contrarianism and Ego

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The Contrarian

Peter Thiel and Silicon Valley's Pursuit of Power

Max Chafkin

In 'The Contrarian,' Max Chafkin provides a meticulous biography of Peter Thiel, one of Silicon Valley's most influential and controversial figures. The book explores Thiel's singular life and worldview, from his conservative roots at Stanford to his founding of PayPal and Palantir, and his early investments in Facebook and SpaceX. Chafkin also delves into Thiel's political activities, including his support for Donald Trump and his role in the lawsuit that destroyed the blog Gawker. The biography is both a portrait of Thiel and an examination of the broader tech industry, highlighting its explosive growth, power, and the controversies surrounding it.

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• Mentioned in 196 episodes

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You’ve almost certainly heard Peter Thiel’s name. You very likely even have an opinion about him. But how much do you actually know about him? One of the most powerful people in America is also one of the most secretive, because that lack of public visibility gives him much more room to exercise a scary amount of control over our country. This week, Adam gets the in-depth scoop on Peter Thiel with Bloomberg Business Week reporter Max Chafkin, who recently authored the book The Contrarian: Peter Thiel and Silicon Valley's Pursuit of Power.

Find Max’s book at factuallypod.com/books

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