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.

Thanks to Netgalley and Penguin Press for the ebook. Peter Thiel is one of the most influential, and enigmatic, leaders to come out of Silicon Valley. Secretive, but craving respect. Insightful enough to make PayPal a success and to put early money into Facebook, but not investing more funds into the company when given the chance (losing out on billions) and too petty to invest in Tesla because of past disagreements with Musk. Politically naive backing Ron Paul for president, but later seeing Trump for what he could do and backing him. This book gives you glimpses into this complicated man who seems like he wants all the money in the world and then recklessly mismanages it. Who seems to want to change the political system, but at other times wants to tear it all down. He seems to want to abolish college, but wants all these schools to respect him. Such an interesting book about a very angry and dangerous man.

The Contrarian” is easily the most controversial book I have read thus far, this year. Racy, rambunctious and reverberating, Max Chafkin’s bold and no-holds barred portrayal of the billionaire investor Peter Thiel, is part polemical and part biographical. Whether or not the reader agrees with all that Chafkin has to say, she sure will remember the book long after she is done with it. The nub of the book is an unraveling of a complex and conflicting persona who seems to be a bundle of contradictions. A man at odds with his own philosophy, an opulent character not thinking twice before associating himself with odious characters, and a vengeful human being hell bent on destroying those who offend him deeply, Peter Thiel is one of Silicon Valley’s most iconoclastic and enigmatic protagonists. An open and overt critic of Big tech who has in great measure contributed to its growth, an avowed proponent of privacy who is responsible for the most dominating intrusion of privacy in the West, courtesy his surveillance company Palantir, and a vociferous advocate of free and democratic speech, who singularly buried the media outlet Gawker for amongst others ‘outing’ him, Chafkin’s Thiel is a hypocritic, high flying colossus inhabiting the rarified yet delicate atmosphere of power and politics.

Thiel is most popularly and prominently known as the leader of the “PayPal Mafia”, a group of former PayPal employees and founders who have since gone on to incorporate technology companies that include Tesla Inc. LinkedIn, Palantir Technologies, SpaceX, Affirm, Slide, Kiva, YouTube, Yelp, and Yammer. The Mafia coterie reads like a who is who of the phalanx of technological innovation and incubation – Elon Musk, Max Levchin, Steve Chen, Reid Hoffman, Ken Howrey, Chad Hurley, Joe Lonsdale, Dave McClure, Luke Nosek, Russel Simmons, amongst others. An acolyte of Ayn Rand and her libertarian ideals, Thiel even started a “Thiel Fellows” scheme – his foundation would churn out $100,000 each to aspiring young boys and girls who would drop out of college and start their own companies. As Chafkin chillingly illustrates in his book, the “Thiel Fellows” was a hastily and haphazardly concocted scheme that did more harm than help. Many of the fellows either dropped out or became slaves to vices such as addiction and alcoholism.

Peter Thiel, even though reviled by many is a man who commands a maniacal degree of reverence. As Chafkin informs his readers, his acolytes are collectively known by the phrase – ‘Thielverse’ – a separate Universe that is home to a pulsating, teeming and throbbing hotbed of fangirls and fanboys. A Stanford alumni, Thiel, scowled at the culture that was permeating and pervading the residence halls at the University. “Shirtless men and bikini-clad women, and music blasted from speakers during what should have been study hours. They drank; they smoked pot; they hooked up. Needless to say, Thiel did not partake of any of it.” It was at Stanford that Thiel honed, fine tuned and perfected his Conservatism. Joining the College Republicans, he discovered Ayn Rand, and Rene Girard. Girard’s concept of “mimetic desire” would go onto greatly influence Thiel in both his personal life as well as professional career. It was also at Stanford that Thiel first became obsessed about the concept of besting death by defeating the notion of aging. Introduced to the concept of ‘extropianism’ (“the idea that burgeoning technological advances would enable humans to live forever and the use of cryonics to freeze human brains for subsequent ‘reanimation’ using computers) by Barney Pell, a computer geek, Thiel went on to invest in companies experimenting with the science of aging.

The master manipulator that Thiel is, he also knew exactly when, where and upon whom he could hedge his fortunes on. Initially backing the candidacy of Carly Fiorina for the Republican nomination, in the run up to the elections of 2016, he slowly but surely shifted his allegiance towards Donald Trump. He even gave a stirring talk at the Republican National Convention. He in fact managed to win Trump’s confidence to such a degree that he was made an integral part of the Trump transition team. During the Trump era, companies formed by Thiel devotees and backed by him in the form of a shareholding, made absolute hay. While Palantir made mega bucks from defense contracts floated by the US Armed Forces, Anduril, a start-up backed by Thiel landed a $5 million contract to provide equipment as part of a ‘virtual wall’ involving inexpensive cameras and other sensors, paired with Artificial Intelligence. When Mark Zuckerberg was accused of filtering away posts put up by conservatives on his Facebook Platform, he requested Thiel to help organise a meeting involving the most prominent amongst all “Tea Party Proponents” to help resolve the issue and to explain the motto and business ethos of Facebook. Thiel, by the way also happens to be one of the earliest backers of Facebook. No small testimony to the power and influence wielded by Thiel in both Silicon Valley and amongst politicians. It was such a political clout that egged on Thiel to audaciously propose the name of Balaji Srinivasan as the top pick to lead the FDA during the Trump regime. Srinivasan happens to be a cryptocurrency entrepreneur, a Stanford University lecturer and also a co-investor along with Thiel in a company formed by Curtis Yarvin (an American far-right blogger purveying extraordinarily radical views under the pen name Mencius Moldbug, once argued in a blog titles “Unqualified Reservations” that democracy in America represented a failed endeavour and hence must be replaced by oligarchy). Even Steve Bannon, the ultimate alt-right proponent, found Thiel’s pick of Srinivasan, inconceivable and inappropriate.

Thiel also comes across in Chafkin’s work as a paranoid believer in the coming of an apocalypse. Owning a gargantuan property in New Zealand, popularly known as the “Plasma Screen House” overlooking the spectacular landscape surrounding Lake Wakatipu, Thiel secured a citizenship by subverting all the necessary rules and regulations. By making ‘strategic investments’ in a New Zealand based company, Thiel satisfied a rule which allowed anyone with more than $7 million in investment capital to stay on indefinitely in the country. But getting a citizenship also meant displaying a concrete intent to relocate to New Zealand and a lengthy stay. Using the weapon of contacts and lobbying, Thiel hobnobbed with the then Prime Minister of New Zealand and managed to get the citizenship despite the fact that he had resided within the territory of New Zealand for all of 12 days as against the mandatory tenure of 1,350 days.

Thiel was also fascinated by the concept of “sea steading”. Patri Friedman, a self-styled anarcho-capitalist and the grandson of the most rabid free market economist of all time, Milton Friedman) founded the Sea steading Institute in San Francisco in 2008. Friedman managed to procure funding from Thiel for his endeavour. The Institute’s founding document articulated its vision in the following words, “to establish permanent, autonomous ocean communities to enable experimentation and innovation with diverse social, political, and legal systems”. Thiel was so enamoured with this concept that he was optimistic about “the nature of government is to change at a very fundamental level”. Thiel however, strategically exited Friedman’s venture by telling the latter that it would “have to stand on its own”. Thiel’s contrarianism could also be gathered and gleaned by his choice of literature. One of his favourite books was an abstract work, or a political screed rather penned by Venture Capitalist, James Dale Davidson, along with journalist William Rees-Mogg. Titled ‘The Sovereign Individual’, this book represented, in the words of Chafkin, “a cyber-libertarian manifesto that predicts the end of the nation state. An uncanny resemblance to the concept of sea steading.

Chafkin’s book is full of astonishing revelations and jaw dropping tales of deceit and deception. It is the chronicle of a man whom the world finds it difficult to both deify and demonise. A man who has cleaved a chasm of opposites in terms of both thought and deed. A nihilist for some and a natty investor for the others, Thiel is a conundrum in himself, However Chafkin ends his book on a more mellow and optimistic note. At the time of its writing, Thiel and his partner Danzeisen are proud parents of two children. Maybe parenthood would induce a paradigm shift in the otherwise ruthless thought process of Peter Thiel.

(The Contrarian – Peter Thiel and Silicon Valley’s Pursuit of Power by Max Chafkin is published by The Penguin Group and will be on sale from the 21st of September 2021)