Max Chafkin had his work cut out for him when he decided to write a book on the controversial tech mogul Peter Thiel. “He’s spent a lot of energy very successfully crafting an image, and that image is of someone very strong and vaguely Trumpian,” Chafkin said. “Anything that humanizes him undercuts that image.” Chafkin, a Bloomberg Businessweek features editor, recently published The Contrarian: Peter Thiel and Silicon Valley’s Pursuit of Power, a deep dive into the world of the notoriously private billionaire conservative who holds immense political power. Chafkin joined Alta Journal newsletter editor Matt Haber for an Alta Live conversation devoted to the secretive life and extraordinary success of Thiel.
Chafkin and Haber began their conversation with Thiel’s early years, including the venture capitalist’s days as a Stanford University student. There, Thiel launched a conservative student newspaper, the Stanford Review, aimed at “taking a piss on the liberal establishment,” Chafkin explained. The publication connected Thiel with like-minded (and predominantly white and male) students who became his colleagues at PayPal and elsewhere and are prominent libertarians and conservatives across the tech industry today. Silicon Valley, Chafkin noted, “owes a debt to that conservative activist project.” After selling PayPal to eBay for $1.5 billion in 2002, Thiel and the rest of the founding team went on to start a raft of companies, acquiring the nickname the PayPal Mafia, with Thiel as Godfather.
In 2016, Thiel broke ranks with other tech leaders to openly support then–presidential candidate Donald Trump. He worked on President Trump’s transition team and set up meetings for the White House with Silicon Valley’s top executives. Along the way, Thiel’s company Palantir benefited from lucrative government contracts.
Haber asked Chafkin how he managed to humanize Thiel and evaluate both conservatives’ and liberals’ perceptions of the investor. The author explained that while Thiel did not sit for an interview, Chafkin conducted extensive interviews with Thiel’s friends and colleagues and consulted a rich paper trail.
These days—despite Trump’s defeat—Thiel seems to enjoy acting as a right-wing power broker and making headlines for his espousal of Trumpism and reactionary politics. Chafkin described Thiel’s catchphrase “going back to the future” as the “tech version of MAGA.” According to Chafkin, Thiel’s political influence allows him to wield more power than such contemporaries as Facebook cofounder Mark Zuckerburg (who was a mentee of Thiel’s) and Tesla Motors CEO Elon Musk (a member of the PayPal Mafia).
One viewer asked Chafkin whether he’s worried about being sued by the notoriously litigious billionaire, especially considering that Thiel funded the lawsuit that ultimately destroyed one of his media enemies, Gawker.com. Given that precedent, noted an admittedly concerned Chafkin, “any journalist who has to write about any billionaire now has to think about this. I would be just as worried if I was writing about Pierre Omidyar or Reid Hoffman,” two tech billionaires who preach liberal politics.
In the future, Chafkin plans to remain focused on the intersection of billionaires, the tech industry, and political influence. “These questions about the power of the tech industry, the power of Silicon Valley, are not all the way answered,” Chafkin said. “I hope the Thiel book starts and amplifies some of the conversations that are already happening, but I think that the growth of this industry is probably the story of our lifetimes.”•
Alta Live is a weekly event series hosted by Alta Journal’s digital editor, Beth Spotswood. Each week, Alta invites innovators, academics, change makers, and artists to share their work with our readers in this free virtual series. Join us next Wednesday for Alta Live: Farley Elliott’s 10 Guides to the Secret West.