Silicon Valley is not a milieu known for glamour and charisma. Still, Peter Thiel has cultivated a mystique. A billionaire several times over, Thiel was the first outside investor in Facebook; he went on to co-found PayPal, the digital-payment service, and Palantir, the data-intelligence company that has worked with the U.S. government. He has co-written a business best-seller, “Zero to One,” and launched a hedge fund; he now runs three venture-capital firms. But Thiel’s aura emanates not so much from these achievements as from a more general fish-out-of-water quality. In 2018, citing a regional intolerance of conservative perspectives, he moved from Silicon Valley to Los Angeles; he recently purchased a mansion in Miami Beach. He served on Donald Trump’s transition team and, in an address before the Republican National Convention, declared, “I am proud to be gay.” He has invested in efforts to “cure” aging, and also in libertarian organizations that hope to create floating cities in international waters. He publishes long, winding essays on politics, globalization, economics, and the nature of humanity that often contain Biblical epigraphs and references to the philosophy of his late mentor and friend, the anthropological theorist René Girard. Thiel also has side projects: Frisson, a now shuttered lounge and restaurant in San Francisco; American Thunder, a short-lived conservative publication geared toward Nascar fans; and the bankrolling of a lawsuit launched on behalf of the wrestler Hulk Hogan, which culminated in the 2016 bankruptcy of Gawker Media.

Thiel has fans who follow him in his peregrinations. He has become a center of gravity in the culture of Silicon Valley, and his infrequent talks and essays are circulated and analyzed by both admirers and critics. In “The Contrarian: Peter Thiel and Silicon Valley’s Pursuit of Power,” the Bloomberg journalist Max Chafkin argues that Thiel “has been responsible for creating the ideology that has come to define Silicon Valley: that technological progress should be pursued relentlessly—with little, if any, regard for potential costs or dangers to society.” Thiel’s devotees see him differently—as a techno-libertarian who associates technological advancement with personal freedom, scientific progress, and even salvation.

Fascination with the rich is pervasive and inevitable, and, as a conservative in a superficially progressive industry, Thiel naturally attracts adherents. Still, he is an odd entry in the Silicon Valley pantheon. He is not a technologist or a product visionary; he does not helm a company that obviously shapes everyday life. Steve Jobs, Bill Gates, Jeff Bezos, and even Mark Zuckerberg have their own fan clubs, but there are no equivalents to Thielian exegesis; few people seem to bother speculating on the intellectual roots of Mark Zuckerberg’s business philosophy. How has a tech investor with esoteric interests captured the imaginations of so many? What is it about Peter Thiel?

Thiel was born in Frankfurt, Germany, in 1967, and first came to the United States as an infant. The family moved to Cleveland in 1968, but later relocated to what was then South West Africa, where Thiel’s father, a chemical engineer, oversaw the development of a uranium mine near Swakopmund. They returned to the U.S. when Thiel was still a young child, settling in Foster City, a middle-class suburb in the Bay Area. Chafkin describes Thiel’s upbringing as Christian and writes that his parents were eventual “fanatical Republicans.” (Thiel denies claims that his parents were Evangelical or Republican.) Thiel, meanwhile, became an archetypal nineteen-eighties geek—a talented student, chess player, and science-fiction enthusiast who was bullied by his peers.

Thiel arrived at Stanford in 1985. He played speed chess, discovered Ayn Rand, and gravitated toward the work of Girard, a professor at the school. Thiel was particularly taken with Girard’s concept of mimetic desire. “Man is the creature who does not know what to desire, and he turns to others in order to make up his mind,” Girard wrote. “We desire what others desire because we imitate their desires.” Mimetic desire involves a surrender of agency—it means allowing others to dictate one’s wants—and, the theory goes, can foster envy, rivalry, infighting, and resentment. It also, Girard wrote, leads to acts of violent scapegoating, which serve to preclude further mass conflicts by unifying persecutors against a group or an individual. Thiel would later use this framework to develop his own theories about politics, tech investing, and culture.

In 1987, Thiel launched a campus monthly, the Stanford Review, with Norman Book, a high-school friend. At a time when other politically active Stanford students were petitioning for South African divestment and protesting the university’s plan to house the Reagan Library, the Review was avowedly conservative. Early issues, Chafkin notes, included a front-page story on liberal professors who were “closet Marxists”; an op-ed casting aspersions on the inclusion of nonwhite authors in a Western Culture course; and a strange, satirical sex column, “Confessions of a Sexual Deviant,” about a straight young man who was celibate by choice. As the aids crisis raged in the Bay Area, the monthly printed treatises against “unnatural forms of sex” and “homophobia-phobia.” Chafkin writes that, when a Stanford senior was charged with sexual assault, the Review published an ardent defense of the rapist.

After law school, Thiel clerked for a conservative judge in Atlanta, then became a first-year associate at a corporate-law firm. He quit his law job after seven months, worked for a while as a derivatives trader, and co-authored a book about campus politics, “The Diversity Myth,” with David Sacks, a friend from the Review. He started a hedge fund, Thiel Capital, with money raised from family and friends, and then, in 1998, met a young cryptographer, Max Levchin, and invested in his startup. Within a year, Thiel was the C.E.O. of Levchin’s company, Confinity, which offered a money-transfer service called PayPal. For Thiel, the service had revolutionary potential: a digital wallet, he said, could lead to “the erosion of the nation-state.” Confinity went on to hire four former Review editors, and half a dozen former staffers.

For a time, PayPal shared a floor with another digital-payment company, X.com, founded by Elon Musk. Like X.com, PayPal began to offer incentives to new customers—ten dollars to every new user, and ten dollars for every new user referred. PayPal was not registered as a bank, and did not collect information about its users; as a result, Chafkin writes, it could be used for illicit transactions that many banks and credit-card companies did not tend to support (porn, gambling), and which the company later banned. Meanwhile, Levchin created an eBay bot that contacted sellers, expressed interest in their wares, and then asked that they implement PayPal in order to be paid. (The company donated the items that it bid for and won to the Red Cross.) Thanks to these ethically dubious techniques—which might now be referred to as “growth hacking”—PayPal’s user base boomed.

By early 2000, PayPal and X had roughly the same market share, and both were losing money After some discussion, the two companies merged under the X name, with Thiel as the executive vice-president and Musk as the C.E.O. According to Chafkin, Thiel disappeared from the company after the 2000 market crash. (Thiel denies quitting at this time.) But, months later, while Musk was on his honeymoon, a group of senior PayPal employees launched a coup, ousting Musk by threatening to resign, and having Thiel instated as the C.E.O. Citing sources close to the negotiation, Chafkin writes that, a year after the takeover, as PayPal prepared to go public, Thiel offered the company’s board an ultimatum: he wanted more equity or he would quit. (Thiel denies any ultimatum.) The board granted him the equity. Shortly after PayPal began trading, in 2002, Thiel flipped the company, selling it to eBay for one and a half billion dollars. As soon as the acquisition closed, he issued a press release announcing his resignation. Rather than continuing to lead PayPal, Thiel planned to start another hedge fund.

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