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Peter Thiel is a protean powerbroker

September 28, 2021, 12:38 AM UTC

Few Silicon Valley power brokers are as enigmatic as Peter Thiel.

The man eludes categorization. He is a gay Christian-sympathizing conservative who has long loved to needle the politically correct crowd. He is an early Facebook investor who decries the effects of social media and calls for antitrust investigations of Big Tech. He is strident libertarian and privacy advocate who sells data-mining software to the government. He is a free speech defender who helped sue an unfriendly blog, Gawker, into oblivion. And he is an immigrant Internet-pioneer, who effectively bought his way into New Zealand citizenship, all the while pushing for closed borders at home. 

In writing a biography of Thiel, the deck was stacked against Max Chafkin, the Bloomberg Businessweek writer and editor who daringly took to the task. His new book, The Contrarian: Peter Thiel and Silicon Valley’s Pursuit of Power, charts the billionaire’s rise from his early days as a precocious chess champion who never quite fit in to a world-conquering tech visionary and political firebrand. Thiel is a contrarian, as the title makes clear, one who eschews mainstream thought. He is also a basket of contradictions—and understanding the inner workings of his mind is frequently an exercise in futility. (Chafkin and Thiel’s interactions were limited, and Thiel refused to respond to fact-checking questions.)

Thiel is a man everyone should more intimately know—though a person can only get so far, given how fiercely guarded he is about his private life and how his mind and motivations appear opaque even to those closest to him. The book is full of tales of back-room intrigue. In his earliest business foray, Thiel helped lead a savage coup to depose Elon Musk as CEO of PayPal. Then at the helm, he somehow managed to weather the dot-com bust and sell the business to eBay CEO Meg Whitman, who apparently despised him. Thiel then reinvented himself variously as a nightclub owner, a hedge fund manager (betting big on Canadian tar sands), a tech investor (writing one of the earliest checks in Facebook), a public intellectual (railing against academia), and a political megadonor (backing far-right ideologues).

If Thiel has an overriding philosophy, it appears to be a will to power coupled with an intense disregard for what other people think. The traits have served Thiel well. He has accomplished more in his 54 years of life than many people ever will hope to. (Of course, if he gets his way—he is an avid life extension research-enthusiast—he will live well past 120-years old.)

Thiel’s morality can be hard to pin down. In Chafkin’s telling, Thiel frequently comes across in the style of a Bond villain. He holds court with unsavory leaders of the alt-right movement. His writings have denigrated democracy and women’s rights. And he takes an interest in seasteading—a Ayn Randian fever dream to evade government by escaping to floating, regulation-free city-states. 

Other times Thiel’s unconventionality makes him strangely endearing. One salient moment involved Thiel delivering what was intended to be a pep-talk at Facebook headquarters after the company’s flop of an IPO in 2012. The speech turned out to be insulting and demotivating, and he was no longer invited back to speak. (“My generation was promised colonies on the Moon,” he said. “Instead, we got Facebook.”)

Then there are more troubling descriptions—the uncomfortable, coldly transactional, and uncaring Thiel. He is described by some people in his orbit as a “sociopath,” as “Nazi-curious” (a descriptor one source later walked back), and, somewhat darkly, as “Shadow President” after the election of Trump. (After becoming Trump’s most prominent Silicon Valley supporter, he forged a close relationship with the transition team. However Thiel’s own team’s suggestions for Trump cabinet positions were apparently considered too wackadoo even for Trump’s then-campaign advisor Steve Bannon to appoint.)

All these tensions tangle Thiel into a Gordian knot of inscrutability; Chafkin tugs the yarn anyway. Thiel has “created companies that have defined our culture and economy over the past quarter century…. He has been the rare futurist who actually managed to accelerate the future,” Chafkin says. “And yet this is only half the story because Thiel has also contributed to a reactionary turn in our politics and society that has left the United States in a much more uncertain place than he found it in when he went into business for himself in the mid-1990s.”

Whether one judges Thiel to be fearless, quirky, or destructively nihilistic, his influence is undeniable. The man has a knack for hedging his bets, transforming otherwise crippling eccentricities into strengths, and scoring unlikely victories.

Even after 336-pages devoted to demystifying the man, Thiel remains as inscrutable as ever. Maybe there is no answer—maybe there is only power, and the pursuit thereof. That is the impression Chafkin imparts.

At the end of the day, Thiel is a grandmaster. He never stopped playing chess.

Robert Hackett
@rhhackett
robert.hackett@fortune.com

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FOOD FOR THOUGHT

America's Internet problem. In an ideal world, fiber-optic cable would be rolled out across the country to provide reliable broadband Internet to the tens of millions of Americans who are estimated to live without it today. But, in the cornfields of Arkansas, the head of Aristotle Unified CommunicationsElizabeth Bowles, says that's bound to be far more costly than anyone in Washington, D.C. expects, Bloomberg Businessweek reports. Installing such a cable in the state's rockiest parts could cost as much as $250,000 per mile. So, Aristotle is using a fixed wireless system like the one the U.S. Navy has used to relay transmutations to its aircraft carriers to try and bring Internet to the masses. 

From the article:

The messy reality on the ground in places such as Arkansas suggests that a mix of physical and wireless networks would be cheaper and more practical than some one-size-fits-all solution. Now states are looking at the feasibility of everything from CBRS to Elon Musk’s Starlink satellites to 5G home internet depending on their geographic challenges. Like Bowles, Vickie Robinson, general manager of Microsoft’s Airband Initiative, a philanthropic program to bring 3 million more rural Americans online by next July, says her team advocates making use of whatever technology is on offer. “What’s going to give you the most bang for your buck? That should be the guiding principle,” says Robinson, who’s provided Airband grant money to Aristotle for several wireless deployments.

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BEFORE YOU GO

"We are in the Pets.com-puppet-mascot era of climate." In the latest issue of Wired, Paul Ford, a writer and cofounder of Postlight, equates the current moment of climate with Web. 1.0. "We have new strategies for recycling, new ways of keeping the sun out of the house, electricity from kites, analytics firms that use machine learning to fix insurance, companies that want to connect millennials with ecological brands. And every one seems sure that they are the solution, that they will help us cross the threshold into degrowth. They know the answer," Ford writes. The potential issue? Well, a bubble, of course. "And then what? It's not like we can just wait for the market to recover and see what happens."

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