We Wanted Flying Cars. Instead We Got Targeted Ads, More Surveillance, Insurrectionists, and Peter Thiel
Bloomberg Businessweek|September 20, 2021
An exclusive excerpt from The Contrarian, a new biography
By Max Chafkin

The meeting started with a thank-you. President-elect Donald Trump was planted at a long table on the 25th floor of his Manhattan tower. Trump sat dead center, per custom, and, also per custom, looked deeply satisfied with himself. He was joined by his usual coterie of lackeys and advisers and, for a change, the heads of the largest technology companies in the world.

“These are monster companies,” Trump declared, beaming at a group that included Apple’s Tim Cook, Amazon’s Jeff Bezos, Microsoft’s Satya Nadella, and the chief executives of Google, Cisco, Oracle, Intel, and IBM. Then he acknowledged the meeting’s organizer, Peter Thiel.

Thiel sat next to Trump with his arms tucked under the table, as if trying to shrink away from the president-elect. “I want to start by thanking Peter,” Trump began. “He saw something very early—maybe before we saw it.” Trump reached below the table groping for Thiel’s hand, found it, and raised it. “He’s been so terrific, so outstanding, and he got just about the biggest applause at the Republican National Convention,” he said, patting Thiel’s fist affectionately. “I want to thank you, man. You’re a very special guy.”

The moment of bro tenderness may have been awkward for Thiel, but it was kind of an achievement. Until the Trump Tower meeting, in December 2016, he’d been known as a wealthy and eccentric venture capitalist—a key figure in Silicon Valley for sure, but hardly someone with political clout. His support of Trump, starting in May 2016, when fellow Davos-goers were mostly bedded down with other candidates, had changed that. He’d gotten a prime-time slot at the Republican National Convention, and then, days after the leak of the Access Hollywood tape, in which Trump bragged about sexual assault, kicked in a donation of $1.25 million. Ignore the sexist language, Thiel advised; voters should take Trump “seriously, not literally.” The argument prevailed, and now Thiel was in an enviable position: a power broker between the unconventional leader-elect of the free world and an industry that was said to hate him.

Much had been made during the campaign about the gulf between Silicon Valley and the Republican Party. The Valley favored immigration and tolerance; Trump wanted to build the wall and roll back rights for LGBT Americans. The Valley prized expertise; Trump used his own coarseness as a credential. Pundits had predicted that these differences would be insurmountable—and indeed early accounts of the meeting, based on the four or so minutes during which media were allowed in the room, suggested that this was what had happened. Business Insider published a photo of Facebook’s Sheryl Sandberg, Google’s Larry Page, and Bezos grimacing under the headline “This Perfectly Captures the First Meeting Between Trump and All the Tech CEOs Who Opposed Him.”

But Silicon Valley also reflected the values of the man who’d organized the meeting, and Thiel—a gay immigrant technologist with two Stanford degrees, who’d somehow found his way to becoming a fervent Trump supporter— seemed to value the expansion of his own wealth above almost all else. After the press left, according to notes from the meeting and the accounts of five people familiar with its details, the tech CEOs followed his lead. They were polite, even solicitous, thanking Trump profusely and repeatedly as he cracked wise at their expense. Trump negged Bezos over his ownership of the Washington Post and Cook over Apple’s balance sheet. “Tim has a problem,” Trump said. “He has too much cash.” The CEOs listened politely.

Trump moved on to mass deportations. “We’re going to do a whole thing on immigration,” he said. “We are going to get the bad people.” These were promises that Thiel supported and the tech CEOs ostensibly opposed. Now, in private, no one objected. They implied that it would be fine to crack down on illegal immigrants as long as Trump would be able to supply their companies with enough skilled foreign workers. “We should separate the border security from the talented people,” Cook said. He suggested the U.S. try to cultivate a “monopoly on talent.” Google former Executive Chairman Eric Schmidt, a longtime friend of Thiel’s despite being a major Democratic Party donor, offered a way to brand Trump’s carrot-and-stick approach to immigration reform in a friendlier way. “Call it the U.S. Jobs Act,” he offered. When conversation shifted to China, none of the CEOs urged restraint; many began offering their own gripes.

Years later, Trump’s advisers would point to this moment, crediting Thiel for convincing Silicon Valley that it could work with a president who’d spent the campaign treating them as a bunch of America-hating globalists. “They were supposed to be the biggest enemies we got, and they’re basically making a nationalistic case,” says Steve Bannon, who attended the meeting and served as chief adviser to the White House. “It was like they finally got invited to lunch with the quarterback of the football team.”

The Trump administration, of course, ended badly for many of the participants in the meeting. Bannon was fired the following year, indicted in 2020, and pardoned just hours before Trump himself left the White House, having become the 11th president in U.S. history to lose reelection. He would depart for Mar-a-Lago in disgrace, his legacy tarnished by a pandemic that has killed hundreds of thousands, his political future linked to a violent insurrection at the U.S. Capitol.

But Trump’s presidency would not end badly for Thiel, who didn’t comment for this article, adapted from my forthcoming book, The Contrarian. Thiel’s companies would win government contracts, and his net worth would soar— and it would, crucially, remain in the legal tax shelter that he’s spent half his career trying to protect. As a venture capitalist, Thiel had made it his business to find up-and-comers, invest in their success and then sell his stock when it was financially advantageous to do so. Now he was doing the same with a U.S. president.

Thiel is sometimes portrayed as the Tech industry’s token conservative, a view that wildly understates his power. More than any other living Silicon Valley investor or entrepreneur—more so even than Bezos, or Page, or Facebook co-founder and Thiel protégé Mark Zuckerberg—he has been responsible for creating the ideology that has come to define Silicon Valley today: 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, but he has been, in many ways, the most influential.

His first company, PayPal, pioneered online payments and is now worth more than $300 billion. The data-mining firm Palantir Technologies, his second company, paved the way for what its critics call surveillance capitalism. Later, Palantir became a key player in Trump’s immigration and defense projects. The company is worth around $50 billion; Thiel has been selling stock, but he is still its biggest shareholder.

As impressive as this entrepreneurial résumé might be, Thiel has been even more influential as an investor and backroom dealmaker. He leads the so-called PayPal Mafia, an informal network of interlocking financial and personal relationships that dates to the late 1990s. This group includes Elon Musk, plus the founders of YouTube, Yelp, and LinkedIn; the members would provide startup capital to Airbnb, Lyft, Stripe, and Facebook.

The ambitions of these men have often gone hand in hand with Thiel’s extremist libertarian political project: a reorganization of civilization that would shift power from traditional institutions—e.g., mainstream media, democratically elected legislatures—toward startups and the billionaires who control them. Thiel secretly funded the lawsuit that destroyed Gawker Media in 2016. He has also made the case for his political vision in college lectures, in speeches, and in his book Zero to One, which recounts his own personal journey from corporate law washout to dot-com billionaire. The success manual argues that monopolies are good, monarchies efficient, and tech founders godlike. It has sold around 3 million copies worldwide.

For the young people who buy his books, watch and rewatch his talks, and write social media odes to his genius, Thiel is like Ayn Rand crossed with one of her fictional characters. He’s a libertarian philosopher and a builder—Howard Roark with a YouTube following. His most avid acolytes become Thiel Fellows, accepting $100,000 to drop out of school; others take jobs within his circle of advisers, whom he supports financially and who promote and defend him and his ideas.

On election night in 2016, a group of 20 or so of these loyalists, including entrepreneurs and investors, joined Thiel at his enormous home in San Francisco to watch the returns come in. “You’re never totally sure,” Thiel declaimed to his courtiers, as Fox News showed returns from Wisconsin and Michigan. “But he had all these elements.” Trump “was silly enough to get all this attention,” Thiel continued. “He was just serious enough to actually do it.”

Thiel’s phone was already ringing, and his aides were discussing their prospects. Thiel was going to be named as a member of the transition’s executive committee in a matter of days, they figured, and Trump would give him a substantial portfolio. “The conversation,” says someone who attended the party, “was basically, ‘Where do you want to work?’ ”

A week later, Thiel reported to Trump Tower with a half-dozen aides. They were Thiel’s type: young, smart, and attractive. “They looked like male models,” Bannon recalls. The group, led by Blake Masters, a longtime aide who’d served as Thiel’s Zero to One co-writer, was given the job of suggesting appointees who could drastically limit the scope of “the administrative state.”

As a political animal, Thiel possessed instincts that could seem almost comically bad. His list of 150 names for senior level jobs included numerous figures who were too extreme even for the most extreme members of Trump’s inner circle. Many were ultra-libertarians or reactionaries; others were more difficult to categorize. “Peter’s idea of disrupting government is out there,” Bannon says. “People thought Trump was a disrupter. They had no earthly idea.”

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