The Dungeon Master

A decade ago, a friend of mine attended a party at the SoHo loft of the Facebook cofounder Chris Hughes on the occasion of his relaunch of The New Republic. (Hughes had left Facebook in 2007 and gone shopping for legacy publications; word on the street was that he had first tried, and failed, to purchase this one.) She drifted into the custom-built library and noted two shelves of well-worn titles that, in content and range, struck her as books that had stayed with Hughes since his days as an undergraduate at Harvard. But there was something impersonal about the remainder of the substantial collection, an impression confirmed as she counted, among other glitches in the simulation, multiple copies of Midnight’s Children and The Last Tycoon. It was reminiscent of when Jay Gatsby’s guest Owl Eyes reveals that his host’s whole library is just for show.

At least Hughes tried. His cofounder Mark Zuckerberg perhaps did not “take enough humanities courses” before dropping out of Harvard, the tech reporter Kara Swisher has suggested. Peter Thiel, the first outside investor in Facebook, has proved to be made of more scholarly stuff than either. He cofounded PayPal and has swashbuckled—in his awkward, halting way—through countless profitable ventures. (His current net worth is somewhere between $3 and $10 billion.) Along the way, he has written provocative essays with titles like “The Straussian Moment” and taught courses on entrepreneurship at Stanford, his alma mater. One of those courses served as the basis for Zero to One, an aphoristic business book he published in 2014 that combines philosophical reflection and pithy advice on start-ups; his most recent syllabus included works by authors as various as Joan Didion and the political theorist Carl Schmitt.

In bright and shallow Silicon Valley, Thiel stands apart for having retained the intellectual intensity of a bookish undergraduate, a quality that has made him an object of curiosity, admiration, and mockery. He stands apart amid the orthodoxy of tech-world social progressivism as much for his conservatism as for his business sense. In some ways, he is an old-fashioned libertarian whose skepticism about government is more widely shared in Silicon Valley than his peers would care to admit. But his beliefs are far more varied and in some cases outré, and his recent activity as a political power broker has prompted speculation about his endgame. He was a featured speaker at the 2016 Republican National Convention and an ally of Trump, and he has been an important supporter of various figures on the bewildering new right. His comment that he “would rather be seen as evil than incompetent” referred to his conduct as a businessman but could just as easily describe his growing efforts to help bring about some obscure new order.

Thiel was born in 1967 in Frankfurt. His father, Klaus, was a chemical engineer who worked for mining companies. The family moved around for his job: from Frankfurt to Cleveland, then to apartheid-era South Africa and South West Africa (now Namibia), then briefly back to Cleveland before settling, when Thiel was ten years old, in Foster City, California. He attended seven elementary schools (including a German-speaking school in South West Africa) and mostly kept to himself, reading atlases and playing chess, at first with his parents and, later, competitively.

As a teenager, Thiel read J.R.R. Tolkien’s trilogy ten times and played computer games and Dungeons & Dragons with friends. His parents were conservative evangelical Christians, and Peter never drank or did drugs. They supported Reagan and so did Peter. He leaned toward libertarianism, a philosophy that had the “prestige of abstract logic behind it,” wrote George Packer in his 2013 book The Unwinding, which includes a biographical sketch of Thiel. He was valedictorian of San Mateo High School’s class of 1985 and matriculated at Stanford, just twenty minutes from home.

Among Stanford’s fun-loving freshmen, Thiel was ostentatiously serious. In front of his often hungover dormmates, he swallowed his morning vitamins one by one at a water fountain, and he went home most weekends. Sophomore year, he found his place socially. He stayed up late sparring with Reid Hoffman, a progressive from Berkeley he had met in a philosophy class, but most of his friends were conservatives. They were an “isolated and besieged group,” Packer writes, and they “relished” that status. Thiel cofounded The Stanford Review and served as its editor. The journal, pretentious and sneering, attacked political correctness on campus and leftist ideas broadly.

Thiel stayed at Stanford for law school, clerked for a federal appeals judge in Atlanta (in his free time rereading Ulysses), and became an associate at the white-shoe firm Sullivan & Cromwell in New York, a job he found crushingly boring. He interviewed for clerkships with Justices Anthony Kennedy and Antonin Scalia but wasn’t hired, which plunged him into a “quarter-life crisis” in which he pondered the mimetic theory of the literary theorist René Girard, with whom he had studied as an undergraduate. Girard postulates that human desires are imitative in origin rather than spontaneous or based in need—in short, we want something (a love interest, a Supreme Court clerkship) because others want it. Even when we defeat our rivals, we are not spared disappointment: possessing the object has not changed our being. Resolving to escape the triangle of mediated consciousness, Thiel left the law firm after just seven months and worked as a derivatives trader at Credit Suisse for a year. At the age of twenty-eight, he moved back to the Bay Area to fashion a new career.

In 1995 he published The Diversity Myth, a polemical book about campus multiculturalism, cowritten with his friend David Sacks, who had succeeded him as editor of The Stanford Review—but Thiel wasn’t banking on writing. He started a hedge fund, Thiel Capital Management, with $1 million raised from family and friends, and when the fund fizzled he got interested in tech start-ups. In 1998 he gave a guest lecture at Stanford on currency trading and was approached by a twenty-three-year-old Ukrainian-born computer programmer named Max Levchin, who pitched him on an idea for encrypting handheld devices. Thiel agreed to invest $240,000, and together they founded the company that became known as PayPal. Their technology facilitated transfers of money from one PalmPilot to another or, in what quickly became the more popular option, between the online accounts of anyone who signed up with an e-mail address.

PayPal merged with X.com, a competitor founded by a South African entrepreneur named Elon Musk, who had dropped out of Stanford two days into an engineering Ph.D. After the new company survived the dot-com crash, Thiel resigned, telling employees he was “more of a visionary and less of a manager,” and Musk remained CEO. But some employees were unhappy with Musk’s management: he was dealing poorly with a growing user-fraud problem and dwindling cash reserves, and he foolishly tried to rebrand PayPal (which was already being used as a verb) as X (opaque, porny). While Musk was on his honeymoon, the mutineers approached the chairman of the board, the venture capitalist Mike Moritz, and threatened to quit unless Thiel was reinstalled. Moritz gave in. Thiel took the company public in 2002 and soon after sold it to eBay for $1.5 billion. His stake was worth $55 million and he left the day the deal was announced.

Thiel has said that he got into the start-up world because he “wanted to work with friends,” not the “frenemies” he had found in the hypercompetitive, zero-sum fields of law and finance. At PayPal, he hired several Stanford friends, including Hoffman and Sacks. These and other Thiel associates, now known as the PayPal mafia, went on to build household-name companies including YouTube, Yelp, Hoffman’s LinkedIn, and Musk’s Tesla and SpaceX. In 2007 Fortune ran a photo of the all-male group, with Thiel as don and Levchin his consigliere. Even if the label for this group of geeky pals from university days is a bit silly, it gets at the outsize power accrued by the entrepreneurs and investors who weathered the first dot-com bust.

Shortly after he left PayPal, Thiel began exploring whether its anti-fraud software could help the US government combat terrorism. “The awareness of the West’s vulnerability called for a new compromise, and this new compromise inexorably demanded more security at the expense of less freedom,” he wrote in “The Straussian Moment,” a 2007 essay that explores the work of Locke, Schmitt, Girard, and Leo Strauss. In 2003 he cofounded Palantir Technologies with Alex Karp, a law school classmate who had gone on to complete a doctorate in social theory at Goethe University in Frankfurt. Named after the seeing stones in The Lord of the Rings and initially backed in part by the CIA’s venture fund, Palantir provided data-mining services to government intelligence agencies and commercial clients. Palantir does not itself gather data; it helps clients integrate and analyze disparate data sets. Government agencies have used the software to track down fraudsters, terrorists (Palantir did not deny a dubious claim that it had helped the US military find Osama bin Laden), and, more controversially, undocumented immigrants.

Thiel is Palantir’s chairman and largest shareholder; after he expressed support for Trump in 2016, the company went from being described as “Alex Karp’s Palantir” to “Peter Thiel’s Palantir.” In 2018 Karp, its CEO and a self-described “progressive warrior,” was confronted by employees concerned about the company’s partnership with Immigration and Customs Enforcement. But he renewed the $42 million contract, arguing that the government, not tech companies, should decide how and when certain technologies be used for surveillance.

Although Thiel and Karp generally disagree on political matters (they “argued like feral animals” in law school, Karp has recalled), they both assert that Silicon Valley has been craven when it comes to national security. After Google ended a contract with the Pentagon under pressure from employees yet continued working with the Chinese government, Thiel called Google “treasonous.” Numerous tech companies since the 1950s have served the military and intelligence establishments, but Palantir has been unapologetic about doing so, and Thiel has embraced doing this work for the state, whether motivated by hawkishness on national security or by dispassionate profiteering.

Thiel is better known as an investor than as an entrepreneur. In 2004 he provided Mark Zuckerberg, whom he met through the Napster cofounder Sean Parker, a $500,000 loan to expand TheFacebook; the loan earned Thiel a 10.2 percent stake, a seat on the board, and a portrayal in the 2010 film The Social Network. (He has since sold most of his Facebook stock but remains on the board.) In 2005 he started the venture capital firm Founders Fund, which has backed Airbnb, Lyft, and Spotify and currently has $6 billion under management. (He has since founded two other venture capital firms.) He was prescient about the real estate crash, but after he fumbled his bets (going long where he should have gone short, and vice versa) his hedge fund Clarium Capital shrank by an order of magnitude from its peak.

Following his PayPal payout, Thiel had begun living large in basic billionaire fashion. He hired assistants, a butler, a cook; he flew on private jets and attended Davos; he bought mansions, a Ferrari, and a nightclub. (An assistant did much of this shopping for him.) Gradually, though, he began to “let his freak flag fly,” as a former Clarium employee put it, and pursued pet interests. He donated to the Seasteading Institute, founded by Patri Friedman (grandson of Milton Friedman) and dedicated to the creation of floating city-states in international waters, and to the Methuselah Foundation, a nonprofit dedicated to curing aging.

His interest in youth is manifold. At PayPal, Thiel offered cryogenics as part of the employee benefits package and declared in a 2009 essay that he stood against “the ideology of the inevitability of the death of every individual.” In 2016 Gawker published a rumor that Thiel “spends $40,000 per quarter to get an infusion of blood from an 18-year-old,” which in turn served as the basis for an episode of the HBO satire Silicon Valley in which a CEO contracts the services of a “blood boy.”

When Thiel clarified in 2018 that he was “not a vampire,” it may not have been entirely about blood: perhaps in an effort to replicate the early dot-com vitality, and almost certainly in an effort to stay intellectually and socially refreshed, Thiel has long surrounded himself with young people of promise, particularly young men. In 2010 he established the controversial Thiel Fellowship, which enticed bright students to skip or drop out of college and pursue their business ideas with a $100,000 stipend.

Thiel has also become involved in electoral politics. In 2008 and 2012 he supported Ron Paul’s Libertarian Party presidential bids, but by 2016 he favored the Republican Ted Cruz, whose 2012 Senate campaign he’d supported. Once he realized that Trump was going to win the Republican primary, Thiel signed up to be a delegate for him at the convention, and donated $1.25 million to his campaign just after the release of the Access Hollywood tape. As a member of Trump’s transition team, he came up with 150 people who could disrupt the “administrative state”; most were too offbeat for Trump, and only a dozen made the cut. (According to Steve Bannon, Thiel arrived at Trump Tower to make his picks in the company of six aides-de-camp who “looked like male models.”)

Thiel has donated more than $22 million to the political campaigns of a cohort whom the journalist Benjamin Wallace-Wells has dubbed “the Thielists” for their shared contempt of the American elite—of which they are, of course, members: Blake Masters (Stanford, Stanford Law, Thiel Capital), J.D. Vance (Yale Law, Thiel’s Mithril Capital), Kris Kobach (Harvard, Marshall Scholar, Yale Law, Justice Department), Josh Hawley (Stanford legacy, Yale Law, clerkship for Chief Justice John Roberts, Missouri attorney general).

The year 2016 also marked the culmination of a much stranger project. In 2007 Valleywag, Gawker’s tech blog, published an item titled “Peter Thiel Is Totally Gay, People.” The post was not mean-spirited by Gawker’s standards—it actually praised Thiel and tied his sexuality to his “quest to overturn established rules”—nor did it get much attention. But Thiel was apoplectic. He called Valleywag “the Silicon Valley equivalent of Al Qaeda” and complained about Gawker’s style of journalism to anyone who would listen, including an Oxford law student named Aron D’Souza. In 2011 D’Souza pitched Thiel an idea over dinner in Berlin: to anonymously fund lawsuits against Gawker until one broke its back. Working through D’Souza, whom everyone involved called simply “Mr. A.,” Thiel hired the entertainment lawyer Charles Harder to identify possible plaintiffs among Gawker’s many enemies.

Harder, who later represented Harvey Weinstein and the Trumps in tangles with the media, brought several suits against Gawker, the strongest one an invasion-of-privacy case on behalf of Terry Bollea, better known as the 1980s World Wrestling Federation star Hulk Hogan. In 2012 Gawker had published a clip from a video, made by Bollea’s best friend, a radio personality named Bubba the Love Sponge Clem, of Bollea having sex with Clem’s wife. Bollea claimed the muddy grayscale surveillance-camera footage had been recorded without his knowledge or consent. In 2016 a Florida jury awarded Bollea $140 million in damages (reduced to $31 million in a settlement). The case ruined Gawker, which filed for bankruptcy and ceased operations. Thiel announced that he had contributed $10 million to the lawsuit, remarking to The New York Times that it was “one of my greater philanthropic things that I’ve done.”

No one really knows why he did it. His sexuality hadn’t been a secret: he had come out to friends in the early 2000s; he stopped bringing women as dates to events and started throwing parties at which male servers wore assless chaps or just aprons. When Thiel revealed his role in the campaign, he told the Times that Gawker was “a singularly terrible bully” and that his objective was “less about revenge and more about specific deterrence.” He told the writer Ryan Holiday that it wasn’t the article itself that bothered him; it was a comment below the post by Gawker’s publisher, Nick Denton, who is himself gay: “The only thing that’s strange about Thiel’s sexuality: why on earth was he so paranoid about its discovery for so long?”

It is often remarked that Thiel is full of contradictions. He’s a libertarian who founded a company that helps governments conduct surveillance. He’s a critic of big tech who has supported Facebook on its mission of world domination. He’s a defender of free speech—in The Diversity Myth, he and Sacks celebrate a stunt in which a law student (and future PayPal executive) named Keith Rabois shouted, “Faggot! Hope you die of AIDS!” outside the residence of a Stanford instructor—who worked to kill a media outlet. But even if asserting tort claims over harmful speech constitutes a betrayal of free-speech absolutism that makes Thiel’s proxy war against Gawker unambiguously hypocritical, it’s still not what makes it interesting. It was unhinged, almost Neronian, yet at the same time disciplined. It was neither profit-motivated nor idealistic, and it makes Thiel as much a cipher as a cartoon villain.

In The Contrarian: Peter Thiel and Silicon Valley’s Pursuit of Power, Max Chafkin, a Bloomberg Businessweek reporter, relies heavily on biographical details from George Packer’s 2011 New Yorker profile and an expanded version that appeared in The Unwinding. This borrowing was a necessity: whereas Packer enjoyed full access to his subject, Chafkin got only two interviews, off the record, separated by a decade. Thiel might have sensed a hatchet job.

In Chafkin’s telling, Thiel was a controlling, haughty kid who developed a persecution complex. In Dungeons & Dragons he consistently chose the role of dungeon master, responsible for steering the course of a given adventure, and his chess set displayed a sticker that said, “Born to win.” He reportedly offered to take the SAT for high school juniors at $500 per test, a singularly mercenary piece of nerdery (though no evidence that he carried out the scheme is presented). He was also bullied, and Chafkin explains his contrarianism as a psychological defense mechanism, a way of “reject[ing] those who’d rejected him.” As an undergraduate Thiel imagined a “pernicious liberal plot” against campus conservatives and gathered a crew of “angry young college men” to fight this spectral foe.

A rival chess player told Chafkin that the only time Thiel broke concentration during his regular dorm-room chess matches was to dispute the lyric “No one, no one, no one ever is to blame,” from a song by Howard Jones, to which Thiel countered, “There’s always someone to blame.” When he discovered during his stint working in New York that “the highbrow East Coast establishment might not want him,” he set out on a path of destruction that culminated in his support of Trump—“he wanted to watch Rome burn,” a Thiel associate told Chafkin. Regarding Thiel’s sexuality, Chafkin speculates that being closeted during and after college made him “uncomfortable in his own skin” and prone to combativeness.

Cheap psychologizing can be the mark of an unsteady biographer. Here it may also indicate an ungenerous one. Chafkin withholds credit and finds fault, starting early and small with the omission of Thiel’s being ranked seventh nationally in chess in middle school, which appears in both Packer’s book and Chafkin’s prior reporting. Or consider Thiel’s return to PayPal: Chafkin describes the replacement of Musk—a plan hatched by cofounder Max Levchin and other senior employees who preferred their previous boss, asked him to come back, and persuaded the board to reinstate him—as “Thiel’s coup,” which in turn serves as evidence of “Machiavellian tendencies.”

Thiel, around whom floats the nebulous “Thielverse,” invites a kind of associationist scrutiny. To mention that a venture is “Thiel-backed” is to suggest there’s something untoward about it, regardless of how little money he gave or how uncontroversial the company’s activities are. Whether Thiel is directly responsible for any given transgression can be tough to sort out, especially when critics describe him in such meaningless terms as “a node between several networks.”^* Chafkin spends several pages on James Damore, a Google engineer who became an anti-PC cause célèbre after he was fired for writing an internal memo alleging that the company had been discriminating against men. When Thiel was asked by Charles Johnson, a far-right political activist, to back Damore’s lawsuit against Google, he declined—yet Chafkin speculates that he likely would have done it had he not been occupied with other diabolical schemes. Chafkin refers to the Cambridge Analytica scandal as “one of the most curious chapters in Thiel’s rise to power,” then describes nothing more than a rogue Palantir employee’s giving the UK firm the idea to develop an app that could scrape data from Facebook. Thiel was not implicated.

Some connections are stronger. Chafkin adds to prior reporting that Thiel, Zuckerberg, and their spouses had dinner with Donald and Melania Trump, as well as Ivanka Trump and Jared Kushner, at the White House in October 2019, when Zuckerberg was in Washington for a congressional hearing on cryptocurrency. At the time, there was conjecture about whether Zuckerberg and Trump had struck some kind of deal, and Chafkin firms up the rumor with a seemingly well-sourced claim:

Thiel later told a confidant that Zuckerberg had come to an understanding with Kushner during the meal. Facebook, he promised, would avoid fact-checking political speech—thus allowing the Trump campaign to claim whatever it wanted. If it followed through on that promise, the Trump administration would lay off on any heavy-handed regulations.

After the dinner, Zuckerberg took a hands-off approach to conservative sites.

If the story—which Zuckerberg has denied—is true, it speaks to the discomfiting de facto power conferred on social media platforms to regulate speech and their slippery policies when doing so. But even in this less tenuous instance of Thiel’s nodality, it’s not clear if he had anything to do with the alleged deal—whereas Chafkin claimed in an interview (though not in the book) that Thiel “brokered” the meeting, the Times had reported that Kushner “pulled together the dinner”—or what he thought about it.

These ambiguities make it hard to trust Chafkin as a judge of Thiel’s influence in the worlds he inhabits. Thiel, we are told, is “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.” Chafkin points to Thiel’s rule-breaking streak at PayPal—where he pursued aggressive growth strategies, some of which he picked up from Musk, and dodged banking-industry regulations—and to his general ruthlessness. His early influence on Zuckerberg is well established: he advised him on cutting out his partner Eduardo Saverin (Thiel apparently didn’t consider Saverin a real founder), though Sean Parker told Zuckerberg in 2004 that Thiel had probably learned such “dirty tricks” from Mike Moritz.

More recent examples are less convincing. Chafkin suggests that the bad behavior of companies including Uber and Juul is “an extension of PayPal,” which is somehow synonymous with Thiel himself. He also points to “a generation of techno-contrarians” who “readily deploy (or hint at) sexism and racism to showcase their independence of thought”—something more easily traced to the organic anarchy of 4chan and 8chan than to a Gen X éminence grise who is, all things considered, extremely offline.

Chafkin seems to be groping toward something more interesting than the notion that Thiel is singularly powerful and maleficent—the idea that Thiel lays bare Silicon Valley’s alarming vision of self-rule, that this story is less one of influence than one of hidden affinity. Chafkin writes that Thiel has tried to “impose a brand of extreme libertarianism that shifts power from traditional institutions toward startup companies and the billionaires who control them.” The heedlessness of the tech industry—“Move fast and break things,” as the former Facebook motto went—is scarcely concealed by the social progressivism of its most prominent figures. (And it certainly predates Thiel.) A 2017 survey by political scientists at Stanford found that tech entrepreneurs are among the nation’s most left-leaning Democrats, except on one issue: government regulation, particularly of the tech industry. The political scientists who conducted the survey call this unusual mix “liberaltarianism.”

An analysis of the ideological leanings of tech figures beyond Thiel could easily slip into an indictment of the self-serving, mix-and-match politics of liberaltarians and of corporate liberal America more broadly (such as the cheap and pervasive “identity washing” of bloodthirsty market capitalism, as when the defense contractor Raytheon celebrates Pride Month). These tech figures serve as acute examples; Zuckerberg bristles at the regulatory state (though strategically embraces it when expedient) and waffles over Facebook’s responsibilities to society generally, all while brandishing progressive values. Perhaps this is why Chafkin’s plotting of Thiel’s ideology feels overdetermined, fecklessly connecting recent developments to some distant precursor (he calls Thiel’s support of Trump “no different from the growth hacking at PayPal”), placing Thiel at the center of broad trends (he claims that Thiel somehow brought the gospel of Ayn Rand to Silicon Valley), and casting every aspect of Thiel’s conservatism as uniformly scandalous.

The Contrarian is most successful in sketching Thiel’s quest, over the past decade, for “real power, political power.” It’s unfortunate, then, that the more exotic aspects of Thiel’s politics become just another part of the broadside, with insufficient delineation between his libertarianism (taxation is theft, except when your company depends on government spending), his common cause with the post-2015 GOP (Trump, nationalism, immigration restrictions), and his truly radical positions, such as his Schmittian distaste for the deliberative premise of liberal democracy. These had been gathering steam for years; Thiel declared in a 2009 essay that he no longer believed “freedom and democracy are compatible” and complained of the “unthinking demos.”

“Peter’s idea of disrupting government is out there,” Bannon told Chafkin, referring to some of the names Thiel had put forth during Trump’s transition. Thiel proposed William Happer, a prominent climate change skeptic, to be Trump’s science adviser; his top pick to lead the US Food and Drug Administration was Balaji Srinivasan, a tech investor who once suggested that people would be better served by a database where doctors and patients rated medications—a “Yelp for Drugs”—than by the agency. According to Bannon, these attempts to dismantle the Beltway alphabet bureaucracy (the “very unelected, technocratic agencies,” as Thiel has described them) failed because “Trump turned out not to be a revolutionary.” “He just hired some Swamp Thing instead,” one of Thiel’s suggested nominees said of his own unsuccessful candidacy.

Thiel’s image as a quixotic libertarian—a Swiss bank account in everyone’s pocket, floating city-states, living forever, Ron Paul for president—is fading as he becomes ever more deeply and instrumentally engaged with the political process. His backing of Trump—“It was my least contrarian bet,” he has said—seems to have been a halfway point on his evolution from idealism to a kind of trollish realpolitik. He wants a big change, and his preferred agents of that change are turning out to be politicians like Masters, Vance, Kobach, and Hawley—the “Thielists,” who like their patron are sharp, fancily educated, bored, and destructive. (Thiel donated to Representative Justin Amash, a young, legendarily sincere libertarian from Michigan, in 2013, but not once Amash became a vocal critic of Trump.)

The Thielists are among those who have, with varying degrees of directness, questioned the legitimacy of the 2020 election results. Chafkin provides scant support for his claim that Thiel “planted many of the seeds that led to the failed insurrection” on January 6, 2021, but Thiel does seem happy enough to reap the benefits. This year he and Donald Trump Jr. are cohosting fundraisers for a challenger to Representative Liz Cheney, who voted to impeach Trump over his encouragement of the Capitol rioters. This insurrectionist entente may be the clearest indication that Thiel is not just a businessman seeking tax breaks and deregulation but is trying to make something happen. To put it in Dungeons & Dragons terms, his agenda might be seen as “chaotic neutral,” a commitment, above all else, to ferment.

An aspect of Thiel’s thinking that gets short shrift in The Contrarian is his argument that technological innovation has stagnated in the past fifty years, notwithstanding the digital revolution. “You have dizzying change where there’s no progress,” he told Packer in 2011. Thiel has taken aim at Twitter (the Founders Fund tagline is “We wanted flying cars, instead we got 140 characters”) and even at the social media company that made his career (“My generation was promised colonies on the moon; instead, we got Facebook,” he said, to Facebook employees, in 2012). Most people, including Thiel’s techno-optimist peers in Silicon Valley, are satisfied with mere gadgetry and imagine more of the same for the future. But this stagnation, he told Francis Fukuyama, is not just a problem for tech; it’s linked to “increasing cynicism and pessimism about politics and economics.”

Thiel sees opportunity in all of this, as both a tech investor and a political donor, but he rarely waxes hopeful, perhaps because he speaks firsthand, and perhaps strategically, of that increasing cynicism and pessimism. In 2011 Thiel had breakfast with Mitt Romney and offered some advice on his presidential run: “The most pessimistic candidate is going to win, because if you are too optimistic it suggests you are out of touch.” Romney didn’t listen. Wallace-Wells observed of the Thielists that their “conservatism seems to be experiencing less of a policy turn than a change in mood, one characterized by anger and retrenchment but perhaps especially by a bleak view of what is to come.” And he credits Thiel with teaching today’s conservative leaders “that the future could no longer be counted on.”

It’s a mistake to call this nihilism, as Chafkin toys with doing. It’s spoiling for a fight, and in Thiel’s case, waiting for some brave new world to emerge. He knows that a true disruption of the American liberal-democratic order as we know it could pay huge rewards or be the end of everything, or both. And like any far-sighted billionaire villain, he has an escape plan, having acquired New Zealand citizenship a decade ago.