PayPal and the PayPal Mafia

Big data controls our lives like never before, and few people are more responsible than Peter Thiel, the billionaire cofounder of Palantir who made the bulk of his fortune by investing early in Facebook. But it turns out that beyond his obsession with data, Thiel is equally fixated on the end times, the rise of the Antichrist, and the recent trend of declining birth rates in the West. This week, Josh and June try to figure out why Peter Thiel has the worldview he does and how it bears out in his investments in natalist technology.

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EPISODE ART: Peter Thiel in a 2016 address to the Republican National Convention. Born in Germany, Thiel spent the bulk of his childhood in an apartheid settlement in South West Africa. After graduating from Stanford and briefly attempting a career in law, Thiel co-founded PayPal, Palantir and numerous venture capital funds, also making a critical early investment in Facebook that now represents the core of his fortune.

AUDIO CLIPS:

• 59:59 – Peter Thiel talks about the Antichrist in a Mercatus Center interview about political theology
• 1:24:12 – Peter Thiel talks about demographic collapse in an episode of The Joe Rogan Experience

FURTHER READING:

• "The Real Stakes, and Real Story, of Peter Thiel’s Antichrist Obsession" by Laura Bullard (Wired, September 30, 2025)

SOURCES:

• "No Death, No Taxes" by George Packer (The New Yorker, November 20, 2011)
• "How the roots of the ‘PayPal mafia’ extend to apartheid South Africa" by Chris McGreal (The Guardian, January 26, 2025)
• "South‐West Africa City Remains ‘More German Than Germany’" by Henry Kamm (The New York Times, October 30, 1976)
• "Quote of the Day: PayPal Co-Founder on Sullivan & Cromwell Stint" (Bloomberg, May 24, 2016)
• "Peter Thiel is totally gay, people" by Owen Thomas (Gawker, December 19, 2007)
• "What Does Palantir Actually Do?" by Caroline Haskins (Wired, August 11, 2025)
• "‘ELITE’: The Palantir App ICE Uses to Find Neighborhoods to Raid" by Joseph Cox (404 Media, January 15, 2026)
• "Jeffrey Epstein Invested With Peter Thiel, and His Estate Is Reaping Millions" by Matthew Goldstein (The New York Times, June 4, 2025)
• "Concern Grows Around Billionaire Peter Thiel’s Period-Tracking App" by Maggie Harrison Dupré (Futurism, September 11, 2022)
• "Surveillance Titan Peter Thiel Invests Millions in New Anti-Feminist Menstrual Tracking App" by Kylie Cheung (Jezebel, September 6, 2022)
• "Would You Wear a Period-Tracker Funded by Peter Thiel?" by Jessica Valenti & Kylie Cheung (Abortion Every Day, November 11, 2025)
• "With backing from Thiel, Recharge Capital launches $200M women’s health investment vehicle" by Catherine Shu (TechCrunch, June 15, 2023)
• "Rhea reaps $10M more led by Thiel" by Kate Park (TechCrunch, May 30, 2024)

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