The Venture-Capital Populist

Illustrations by Mike McQuade The courtship between Silicon Valley and MAGA was consummated on June 6, 2024, in San Francisco’s Pacific Heights neighborhood, on a street known as “Billionaires’ Row,” at the 22,000-square-foot, $45 million French-limestone mansion of a venture capitalist named David Sacks. Along with Chamath Palihapitiya, a fellow venture capitalist and a colleague on the All-In podcast, Sacks hosted a fundraiser for Donald Trump. He knew that other technology titans were coming around to the ex-president but remained in the closet. “And I think that this event is going to break the ice on that,” Sacks said on the podcast the week before the fundraiser. “And maybe it’ll create a preference cascade, where all of a sudden it becomes acceptable to acknowledge the truth.” A few years earlier, Sacks had described the January 6, 2021, riot at the U.S. Capitol as an “insurrection” and pronounced Trump “disqualified” from ever again holding national office. “What Trump did was absolutely outrageous, and I think it brought him to an ignominious end in American politics,” he said on the podcast a few days after the event. “He will pay for it in the history books, if not in a court of law.” Palihapitiya was more colloquial, calling Trump “a complete piece-of-shit fucking scumbag.” These might seem like tricky positions to climb down from—but the path that leads from scathing denunciation through gradual accommodation to sycophantic embrace of Trump is a well-worn pilgrimage trail. The journey is less wearisome for self-mortifiers who never considered democracy (a word seldom spoken on the podcast) all that important in the first place. One prominent traveler who had already shown the way was a guest at the fundraiser—Senator J. D. Vance, whose attendance helped close the deal on his selection as Trump’s running mate. Any lingering awkwardness between the hosts and their guest of honor was dispelled by the fundraiser’s $12 million haul, much of it from cryptocurrency moguls. Opportunist doesn’t really describe Sacks. He doesn’t come across as slippery or two-faced. There’s no evasive glance or roguish smile. He can argue at great length, in a steady sinal drone, with an aggressive debater’s ability to make an evidence-based case for any position he holds—but the position always happens to coincide with his benefit. The only consistent principle of his career is a ruthless devotion to self-interest. Sacks has identified as a “libertarian conservative” all of his adult life, but he has sought government intervention on behalf of his investments when it’s suited him. In 2023, when Silicon Valley Bank collapsed, Sacks demanded that the federal government bail out the uninsured deposits of start-up companies, much of the money from crypto firms. “Some libertarians care about the freedom of only one person,” Peter Thiel, the entrepreneur, investor, and right-wing provocateur, once said of his friend Sacks. [From the May 2026 issue: What Noah Hawley learned about billionaires at Jeff Bezos’s private retreat] In this sense, though Trump is impulsive and narcissistic while Sacks is cold-eyed and logical, they are well matched. “Sacks is a spirit animal for part of the president’s brain,” a former Biden-administration official told me. “The plutocratic part.” After the election, the new president appointed Sacks as his special adviser, or “czar,” for AI and crypto. After decades of keeping as far from Washington as possible, Silicon Valley would finally have its own man in the White House. But Sacks has always taken a dim view of politics. At 25, appearing on a C‑SPAN talk show while still in law school, he expressed a preference for “the ethos of Wall Street” over “the ethos of Washington” and quoted Calvin Coolidge on the business of America being business, avowing: “I’d probably rather live in a greedy country where people don’t share than in an envious country where people are stealing from each other.” Sacks went to Washington on behalf of business, including his own. But business and politics demand different, sometimes opposing talents. “Sacks’s policies are misaligned with his own party,” a congressional aide with a close view of how Sacks operates in Washington told me. “He doesn’t really understand how D.C. works.” His efforts in government on behalf of the tech industry have exposed the president to the charge that Trump is selling out his populist base on behalf of the country’s richest men, driving a wedge through the MAGA coalition. Sacks once called a rare victory over Thiel in a game of chess one of the greatest moments of his life. In a photo, his arms are raised skyward, ecstatic disbelief on his face. He spent the early years of his career as a kind of junior partner in Thiel’s shadow. Sacks was born in 1972 in South Africa, and moved to the United States at age 5. He grew up in Memphis and attended an elite boys’ prep school before going on to Stanford University. As a sophomore with right-wing views he inevitably gravitated toward Thiel, who was by then in law school, and joined The Stanford Review, the conservative campus publication that Thiel had started as an undergrad. It took aim at the politically correct orthodoxy and anti-Western ideology that swept over American higher education in the late ’80s and early ’90s and never really left. But the outnumbered young conservatives’ mockery almost always overshot the target. An entire issue was devoted to making light of rape, including a contribution from Sacks that challenged whether statutory rape should be a crime. (He has since expressed regret for some of his youthful writings.) Thiel was determined to be a public intellectual like his hero William F. Buckley, so he began writing a book on left-wing campus extremism. When he found the work too onerous, he turned the research over to Sacks, and they co-authored The Diversity Myth: Multiculturalism and Political Intolerance on Campus, published in 1995 by a libertarian think tank. Sacks attended the University of Chicago Law School, but law was too much like the detested public sector, and in 1999, when Thiel co-founded an online-payments company in Palo Alto that was soon to be called PayPal, Sacks left a consulting job to lead the company’s product team. He made important contributions to PayPal’s success; by various accounts, including Sacks’s own, he was also known for telling co-workers in blunt terms that they were wrong. A former colleague told me that with Sacks, “there’s masters and there’s slaves. He doesn’t have partners: ‘You do what I tell you to do, or you’re one of the few people that tell me what you want me to do.’ ” The former colleague added, “Part of his drive is that he believes he is one of the small number of elite people who really get it and are capable.” (The former colleague and some other Silicon Valley sources requested anonymity to discuss a figure who has power over their businesses; some government officials requested anonymity to speak about White House conversations, because they were not authorized to talk about them. Sacks declined to be interviewed.) PayPal became famous for surviving the dot-com crash in 2000, and for producing a spawn of Silicon Valley stars known as the PayPal Mafia, including Sacks. Roger McNamee, a longtime tech investor, watched its success with admiration and apprehension. The PayPal Mafia saw before anyone else that the cost of starting an internet company was going to drop significantly. “They realized that the limits on processing power were going to go away,” McNamee told me. But these 20- and 30-somethings were not inspired in the same way that the founders of earlier Silicon Valley companies were: “They didn’t follow the vision of Steve Jobs, that tech can democratize power. They came to get rich.” McNamee added, “If their value system had been different, we would have a completely different country today.” I met Sacks in 2011, at a dinner at Thiel’s house in San…