The Contrarian

INTRODUCTION

It may seem hard to remember, but there was a time when the world seemed ready to put Silicon Valley in charge of everything. This was 2016—the “Age of Unicorns,” as business magazines called it, referring to tech companies that were growing so quickly, and had become so valuable, that they seemed almost mythical. Jeff Bezos had saved one of America’s great newspapers, Mark Zuckerberg was romancing San Francisco politicos, who’d just named a hospital after him, and transportation activists were showing up in major cities to protest in favor of the disruptions brought on by Uber. President Barack Obama, his term winding down, was musing about relocating to California and becoming a tech investor as his next act. Venture capital, he told to reporters that spring, sounded like it could be “very satisfying.”

But even as the zeitgeist—all the way up to ambitions of the leader of the free world—celebrated the promise and potential of Silicon Valley, one of Silicon Valley’s pioneers had already turned his attention well beyond it. Over the prior two decades, Peter Thiel had accumulated billions of dollars in wealth, backing some of the biggest and most successful tech companies, including Facebook, PayPal, and SpaceX. He’d built a network that gave him access to the best entrepreneurs and the wealthiest investors in the world, and he was idolized by a generation of aspiring startup founders. But Thiel wanted more than sway in Silicon Valley—he wanted real power, political power. He was about to be handed an opportunity to seize it.


It came in the form of what appeared at first to be a minor scandal at Facebook, where Thiel had been an early investor. That May, the tech blog Gizmodo published a report claiming that the opinions of conservatives were being systematically suppressed by the social network. A small team of editors working on a new feature called Trending Topics said they’d been instructed to include stories from mainstream outlets such as CNN and The New York Times, but to leave out stories from right-wing media as well as those about fringe topics popular among conservatives, such as the unverified claim that the IRS had been targeting Tea Party‒affiliated nonprofits.

The scoop was modest—Trending Topics had nothing to do with the regular news feed, which was curated by algorithm and was full of right- wing content—but it enraged conservatives, who saw it as proof that Facebook was biased in a broader way. The Drudge Report, which had been among the banned outlets, led with a giant and unflattering pic- ture of Zuckerberg’s deputy Sheryl Sandberg, the author of the book Lean In. not leaning in . . . leaning left! the headline screamed. facebook under fire was the Fox News chyron.

Facebook denied the allegations, but Zuckerberg sensed that this was a crisis to be managed, and he turned to Thiel to help him. On Wednesday, May 18, a group of sixteen prominent right-wing media personalities were summoned to Menlo Park for a meeting. They included talk show hosts Tucker Carlson, Glenn Beck, and Dana Perino; the presidents of the Tea Party Patriots, the American Enterprise Institute, and the Heritage Foundation; and a handful of others. Officially, they were there to see Zuckerberg and Sandberg, but Thiel was the reason many of them had made the trip.


At forty-eight, he was more than a decade older than the Facebook founder, but the two men had much in common. Like Zuckerberg, Thiel was ruthlessly competitive and awkward in social situations. They’d been close—Thiel had been Zuckerberg’s mentor and his patron, the first out- side investor in his company and the first person in authority to grasp that Zuckerberg actually knew what he was doing.

Years earlier, Thiel had seen in the Facebook founder—an abrasive, socially inept young man whose chief business qualification at the time was that he’d hacked together a way to rate the attractiveness of his female classmates at Harvard—something huge. After investing in Facebook, Thiel had set up Zuckerberg with absolute control over it, helping to transform the kid with the words “I’m CEO . . . Bitch” on his business cards into the fairly polished capitalist he would become. The relationship had made both men spectacularly rich, and though Thiel no longer owned much Facebook stock, he remained on the company’s board and was still very much invested in its influence.

Zuckerberg and Thiel had drifted apart over the previous few years, as Thiel had become more entrenched in the world of conservative politics and Zuckerberg had embraced the spirit of the Obama era, starting a lobbying group aimed at promoting business-friendly immigration reform and pledging billions to the causes of “advancing human potential and promoting equality.”

But even as he cultivated Obama and others on the left, Zuckerberg had continued to rely on Thiel as a liaison to the American right. Thiel, according to Zuckerberg’s allies, was the company’s conservative conscience. “Mark wants to have a balance at Facebook between left and right,” said a former Facebook executive. “He doesn’t think he can have a healthy debate if everyone’s a bleeding-heart Democrat.” Zuckerberg’s critics saw Thiel’s influence on the company as more profound—and more pernicious. He was, in this view, the puppet master: pushing a younger, ideologically uncertain founder toward an alliance with an ex- tremist wing of the Republican party.


As the group of conservative leaders arrived at Facebook’s sprawling Frank Gehry‒designed headquarters, Thiel and Zuckerberg were a study in shifting generational attitudes toward the concept of business casual. The Facebook founder wore his usual uniform, a gray T-shirt and jeans. Thiel wore a dress shirt with the sleeves rolled up and a pair of hempsoled shoes. As usual, he carried himself as if braced for a collision—his shoulders hunched forward, his head tucked ever so slightly.

The group sat down at a large table, and Zuckerberg and Sandberg led them through a dense, technical presentation designed to explain that Facebook’s software, not editors, selected the vast majority of articles that appeared on Facebook. Zuckerberg asked if there were any questions— which the pundits took as an invitation to light into Facebook, the company’s left-leaning employees, and the general sense that Silicon Valley favored liberal causes.

“They were letting him have it,” recalled Glenn Beck, the talk radio personality and former Fox News host known for his histrionic conspiracy theories and goofy on-camera antics. “He deserved some of it.”

Beck was one of a handful of the attendees whom Thiel had been quietly cultivating. After he’d left Fox News under tense circumstances—rumor had it that Wendi Deng, Rupert Murdoch’s wife, had demanded his ouster amid his show’s conspiratorial turn during the Obama administration—it was Thiel who’d convinced him to focus on streaming videos and podcasts. “You just have to decide if you are in the future or are you in the past,” Thiel had told him.

Beck was fond of Thiel and, in the meeting, assumed the role of Zuckerberg’s defender. “You’ve got thirty people who have spent decades defending freedom of speech,” he said, addressing Zuckerberg and gesturing to his colleagues. “And you have this platform that has given hundreds of millions of people the freedom of speech.”

Zuckerberg seemed moved by Beck’s show of empathy. “We built Facebook to be a platform for all ideas,” he wrote on his Facebook page after the group departed. “Our community’s success depends on every- one feeling comfortable sharing anything they want.”


The message to employees, and the outside world, was clear: Facebook intended to allow supporters of Donald Trump, who was by then the de facto Republican nominee, to say more or less whatever they wanted on its platform. Over the next several months, misinformation on Facebook—much of it in Trump’s favor—outperformed real news. The most popular election headline on Facebook during that period, according to one study, was pope francis shocks the world, endorses donald trump for president, which, of course, never happened. Another claimed falsely that Wikileaks emails revealed that Hillary Clinton had sold weapons to Islamic State terrorists.

Zuckerberg would eventually apologize—sort of. “We didn’t take a broad enough view of our responsibility, and that was a big mistake,” he’d later tell Congress when called to answer questions about the ways that Facebook had been used to manipulate the election campaign. But in the moment, the company denied that it was helping to spread misinformation, while downplaying the extent of the Russian government’s involvement.

Two months after the meeting in Menlo Park, Thiel formally endorsed Trump, becoming the star of the Republican National Convention in Cleveland. Then, in mid-October, just days after the release of the Access Hollywood tape, in which Trump bragged about sexual assault, Thiel donated $1 million to Trump’s campaign. The move helped turn a tide of negative press and added to the coffers of a campaign that would buy a barrage of targeted Facebook advertisements as part of a voter suppression strategy designed to discourage potential Clinton supporters.

After the election, Thiel was feted by Trump’s inner circle and given an office in Trump Tower, along with the latitude to install his allies in the new administration. “He was something unique,” recalled Steve Bannon, who became CEO of the campaign in August. He praised Thiel for bringing intellectual credibility and seriousness to a campaign that struggled at times to convey either. To Bannon and others on the Trumpist right, Thiel was a hero, a key enabler of Trump’s unexpected win.


To the left, Thiel was uniquely villainous—a Silicon Valley power broker who’d helped hook Americans on a collection of tech services, then used his influence over those services to elect a candidate who promised to ban Muslims from entering the United States and to deport millions of undocumented immigrants. For years, activist groups had been warning of exactly this kind of thing—of the power that Silicon Valley had been accumulating and of the nationalist undercurrents swelling just below a sheen of left-of-center idealism. The far-right ideas had been there for as long as the tech industry had existed—all the way back to the founding of Stanford University. But it had taken Peter Thiel to bring those ideas above the surface, and then to weaponize them.
 
Thiel is sometimes portrayed as the tech industry’s token conservative—a view that wildly understates his influence. More than any other Silicon Valley investor or entrepreneur—more so even than Jeff Bezos, or Google founders Larry Page and Sergey Brin, or Zuckerberg himself—he 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 isn’t the richest tech mogul—though he’s almost certainly better at shielding his assets than the average Valley billionaire, having arranged to pay little in taxes on an investment portfolio worth something like $10 billion—but he has been, in many ways, the most influential. His first company, PayPal, pioneered ecommerce and—after being spun out of the company to which Thiel sold it, eBay—is worth nearly $300 billion, as of early 2021. Palantir, his second company, popularized the concept of data mining after 9/11 and paved the way for what critics of the technology industry call surveillance capitalism. More recently, it became a key player in the Trump administration’s immigration and defense projects. The company is worth around $50 billion; Thiel controls it and is its biggest shareholder.


As impressive as this entrepreneurial resume might be, Thiel has been even more influential as an investor and backroom deal maker. He leads the so-called PayPal Mafia, an informal network of interlocking financial and personal relationships that dates back to the late 1990s. This group includes Elon Musk, plus the founders of YouTube, Yelp, and LinkedIn. They would provide the capital to Airbnb, Lyft, Spotify, Stripe, DeepMind—now better known as Google’s world-leading artificial intelligence project—and, of course, to Facebook.

In doing so, Thiel and his friends helped transform what was once a regional business hub—on par with Boston and a few other midsized American metro areas—into the undisputed engine of America’s economy and culture. In 1996, there were no tech companies among the five most valuable traded on U.S. exchanges; in 2021 the entire top five consisted of U.S. tech companies. Today, the most prolific Hollywood studio is Netflix. More Americans get their news from social media, primarily Facebook, than from cable television.

This growth hasn’t been entirely benign. The tech industry, which is still seen by many as a cultural backwater full of socially clumsy but well-meaning nerds, is now an acquisitive and seemingly amoral force, one capable of producing new forms of entertainment, new mediums of communication, and a better way to hail a taxi, but one that is also indifferent to the addiction, radicalization, and economic privation that have come with these advances. The Ubers and Airbnbs America embraced in 2016 had costs. They replaced salaried jobs of taxi drivers and hotel workers with lower-wage, lower-security gigs, and then aggressively thwarted efforts by governments to rein them in.

This shift was part and parcel with Thiel’s other project: an attempt to impose a brand of extreme libertarianism that shifts power from traditional institutions toward startup companies and the billionaires who control them. The Thiel ideology is complicated and, in parts, self-contradictory, and will take many of the pages that follow to explore, but it combines an obsession with technological progress with nationalist politics—a politics that at times has seemingly flirted with white supremacy. Sweetening what might otherwise be a rather sour concoction is Thiel’s personal story—a journey from washout corporate lawyer to dot-com billionaire that he has recounted many times in college lectures, speeches, and in his book, Zero to One. The libertarian success manual also argues that monopolies are good, that monarchies are the most efficient form of government, and that tech founders are godlike. It has sold more than 1.25 million copies worldwide.

For the young people who admire him, watch and rewatch his talks, write social media odes to his genius, and buy his books, Thiel is like Ayn Rand crossed with one of her fictional characters. He is both libertarian philosopher and a build r—Howard Roark with a YouTube following. The most avid acolytes among these fanboys and fangirls become Thiel Fellows; his foundation pays them $100,000 each to drop out of college and start companies. Others have taken jobs within his coterie of advisers, whom he supports financially and who promote and defend him, his friends, and his ideas. These people sometimes talk about a “Thielverse,” a world with its own laws, its own morality, and, always, a gravitational pull toward the patron. As Thiel has become more powerful, those laws have become the laws of Silicon Valley itself. They increasingly seem to have purchase well beyond it.

Thiel’s worldview has become so influential that it shows up even among his adversaries. Google’s former chair, Eric Schmidt, whom Thiel has skewered as a monopolist and a “minister of propaganda,” proclaimed himself “a big fan” of Thiel, praising in particular his campaign of revenge against Gawker Media. That campaign, in which Thiel secretly financed a lawsuit brought by the wrestler Hulk Hogan against the company, drove Gawker out of business in 2016. Thiel’s efforts combined financial pressure and deception—an approach that free-speech advocates have criticized sharply but that Schmidt said left him “very impressed.” “We need people who can challenge orthodoxy, and he is willing and delighted to do so,” he said. Schmidt, a liberal who served as an adviser to Hillary Clinton’s campaign, told me he considers Thiel’s support of Trump admirable and “part of his contrarian view of the world.”


This has been the consensus view on Thiel—that he is a consummate freethinker, a man constitutionally incapable of following the herd. It’s one that Thiel himself has endorsed at times. “Maybe I do always have this background program running where I’m trying to think of, ‘O.K., what’s the opposite of what you’re saying?’ and then I’ll try that,” he said shortly after the 2016 election. “It works surprisingly often.”

Even so, Thiel’s role in Trump’s rise to power stunned members of the tech press, as well as some of Thiel’s friends. How, they wondered, could a bookish, gay immigrant from the most liberal part of California, who’d gotten rich in the world’s most globalized industry, who seemed so profoundly committed to the promise of a better future, come to support a reactionary would-be authoritarian? I was transfixed by another question: How had Thiel, who’d arrived in Silicon Valley in the mid-’90s as an unknown, failed financier, come to wield so much power? He was a contrarian, yes, but contrarianism is a methodology, not an ideology. What exactly, I wondered, did Thiel actually believe? And how deeply embedded were those beliefs in Silicon Valley itself?
 
In 2007, when I was a junior reporter with Inc., a small business magazine, I’d sat in Elon Musk’s cubicle at what was then the very modest headquarters of SpaceX, his rocket company. Musk was on the phone, half-listening to a conference call and checking his email at the same time. While I waited for him, I stared at a poster for the movie Thank You for Smoking, based on the novel by Christopher Buckley, son of William F. Buckley and a former speechwriter for George H. W. Bush.


The credits listed on the poster included Musk’s name, along with those of several other PayPal Mafiosi: Mark Woolway, a PayPal vice president, and David Sacks, the company’s COO. Thiel’s name was there, too. By then, he already had a reputation as a bomb thrower, which made the movie, a satire in which the hero is a tobacco industry lobbyist, seem appropriate. Peter Thiel would be a fan of Big Tobacco—or, at least, he’d be totally fine being seen that way.

Later that day, Musk told me the story of his firing from PayPal. He’d been the victim of a secret boardroom plot, masterminded by Thiel while he was on his honeymoon. Musk forgave Thiel eventually. “I buried their hatchet,” he said, referring to Thiel and his coconspirators. He reached behind his back, miming the removal of a blade from his left scapula. During the interview—and in another much more recent one for this book—Musk managed to affect grace while also making it clear that he does not entirely trust Silicon Valley’s most important venture capitalist.

From that point on, Thiel seemed to hang behind or above or somewhere in the middle of almos every story I reported about the tech industry, and increasingly, many stories beyond it. In 2011, years before progressives started talking about free college, Thiel was warning about rising tuition prices, calling the higher education industry a bubble more troubling than the one in real estate. He helped to jumpstart the backlash against big tech in 2014 when he called Google a monopoly—years before Elizabeth Warren or Bernie Sanders would. And then, of course, came his destruction of Gawker and the election of Trump.

In 2018, I started interviewing former employees, business partners, and other associates—in Silicon Valley, Washington, D.C., and elsewhere—to try to understand how this had happened. Thiel had come to the tech industry with little in the way of money and no engineering ability to speak of. He had no special social graces, and rarely seems to enjoy himself. He speaks haltingly. He is not charismatic, at least not in any traditional sense.

What I learned was eye-opening: Thiel, according to his friends, is brilliant—capable of visionary insights and with an uncanny ability to know exactly how to win. He has the special ability to see life like a chess game—using his friends, his business partners, and his portfolio companies as means to an end. There was a less appealing side to this, of course. The Machiavellian tendencies could make him coldly transactional, to the point, sometimes, of cruelty.

I’d expected Thiel’s close friends to blandly sing his praises. Some did. But the more common reaction to my questions, from Thiel’s friends—people in positions of political power; businesspeople worth many, many millions of dollars; investors able to command the attention of billionaires—was not admiration, exactly. It was fear. They told me they were scared of him. He was that powerful, and he was that vindictive.

During one of these early interviews, a person who has known Thiel for many years, with a successful career in Silicon Valley built in part thanks to associations with Thiel’s network, told me to stop my digital audio recorder. “I’m paranoid,” he said. Then he proceeded to share a series of anecdotes that portrayed his patron as an incredible investor, with a knack for identifying and nurturing young talent, but who had a ruthlessness that made him uncomfortable.

Then he got personal. “Why do you want to write this book?” he asked. “I mean, aren’t you worried he’ll, like, come after you?”

As I write this, a cohort of the Valley’s investors and entrepreneurs—nearly all of them with strong financial and social ties to Thiel—have decided that even the act of reporting critically on Thiel and his friends is no longer acceptable. Balaji Srinivasan, an investor who was one of Thiel’s picks to lead the FDA under Trump—has argued that the media deserves to be destroyed and replaced by something he calls “full stack narrative”—public relations, in other words. “Builders must critique the critiques,” he tweeted, using the Randian word for entrepreneur that is favored by Thiel and his friends. “Stop the people standing athwart the future yelling stop. It’s your duty.”
In certain circles, Thiel’s name itself is a verb. To “Peter Thiel” a media outlet or a journalist is to bankrupt them, à la Gawker. The suit, which led to a $140 million verdict against a media company that had published a series of unflattering posts that suggested that Thiel was a “so-called visionary” and disclosed that he is gay, sent an unmistakable message to critics: those who publicly criticize Thiel, or any of his friends, do so at their peril.

Because of his track record for trying to hurt those who’ve attempted to uncover his secrets, many of the more than 150 former employees, business partners, friends, and others with whom I spoke over the course of hundreds of hours of interviews for this book insisted on anonymity. Thiel’s most powerful allies fear him and so, naturally, do some of his former middle-school classmates. I was in communication with Thiel throughout all this—mostly through intermediaries. I’d met him once in 2011, and we met again, in person, in 2019. He insisted that the meeting be off the record. He declined to respond to a lengthy list of fact-checking questions.

My goal, in the pages that follow, is to try to understand a man who has made billions of dollars in part by being inscrutable. I wanted to understand how he’d managed to build such a devoted following and how he’d been able to so consistently make the right bets, even when they seemed crazy. I wanted to und rstand how somebody so respected and beloved could have gotten that way while also acting ruthlessly. Was Thiel a genius worthy of admiration and study, or a sociopathic nihilist? Could he be both?

These questions matter because they are the same ones we are asking of the big tech companies that the Thielverse gave us. In part because he was instrumental in building it, and in part because so many powerful people came to admire and copy him, much of Silicon Valley is today a reflection of Thiel’s worldview, for better or worse. If we want to understand Zuckerberg or the new monopoly capitalism—or for that matter the Trumpian far-right, which Thiel nurtured secretly too—we need to understand him.