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   regret it.” In all, Airbnb spent eight million dollars on the campaign,   
   roughly ten times as much as all of Proposition F’s supporters   
   combined. “It was the most ridiculous campaign I’ve ever worked on,”   
   the staffer told me. “It was so over the top, so extreme. You shouldn’t   
   be able to spend that much on a municipal election.” That said, the   
   staffer loved her time at Airbnb: “It was the most money I’d ever   
   earned working in politics.”   
      
   The third aspect of Lehane’s strategy was upending the debate over   
   Proposition F by proposing alternative solutions. Otherwise, Lehane and   
   Airbnb’s chief executive, Brian Chesky, believed, the company would   
   face similar proposals in other cities. “You can’t just be against   
   everything,” Lehane told the Airbnb board. “You have to be for   
   something.” As a compromise gesture, Airbnb had voluntarily begun   
   paying taxes on short-term stays within the city. It also offered to   
   share some internal company data—such as the number of guests visiting   
   the city each month—that would help local officials monitor the   
   service’s impact on the community. What’s more, Airbnb eventually   
   offered to build a Web interface that San Francisco officials could use   
   to register hosts and track rental patterns. The solution was self-   
   serving, in that it made the city dependent on Airbnb for monitoring   
   Airbnb’s activities. But the proposals addressed many of the complaints   
   that had prompted Proposition F. More important, they guaranteed San   
   Francisco tens of millions of tax dollars annually. When Proposition F   
   finally came to a vote, it was resoundingly defeated.   
      
   Airbnb’s approach to political conflict was in stark contrast with that   
   of Uber, which had just become the most valuable startup in the   
   world—and which, owing to its resistance to various taxi regulations,   
   was soon under fire from multiple cities and nations. Airbnb’s tactics   
   were designed to appeal to politicians’ higher ideals. After the   
   Proposition F campaign, Lehane began working on a partnership with the   
   S.E.I.U., one of the nation’s largest labor unions, to unionize the   
   workers who cleaned Airbnb rentals. The plan never came together, but   
   labor-friendly politicians in San Francisco and New York began viewing   
   Airbnb as a potential ally.   
      
   To other political operatives, Lehane’s tactics hardly seemed   
   groundbreaking. But within Silicon Valley his approach was a   
   revelation. “It was a huge bang for a relatively small outlay,” a tech   
   executive told me. “It turns out the R.O.I.”—return on investment—“on   
   politics is way better than anyone suspected.”   
      
   After the defeat of Proposition F, San Francisco’s Board of Supervisors   
   eventually agreed to many of Airbnb’s suggestions. By then, Lehane had   
   moved on to other locations. He began similar Airbnb campaigns in   
   dozens of other cities, including Barcelona, Berlin, New York, and   
   Mexico City. When the U.S. Conference of Mayors convened in Washington,   
   D.C., in 2016, Lehane was invited to speak after Michelle Obama. “Read   
   my lips,” he told the gathering. “We want to pay taxes.” Airbnb soon   
   had agreements with more than a hundred cities, and when local   
   politicians proved intransigent—leaders in Austin, for instance, seemed   
   immune to Airbnb’s overtures—the company simply went over their heads.   
   In Texas, it persuaded the state legislature to make it hard for any   
   municipality to ban short-term rentals. Today, Airbnb has agreements   
   with thousands of cities.   
      
   A few years after Lehane joined Airbnb, a venture capitalist pulled him   
   aside at a party and said, “It used to be, hiring the right C.F.O. was   
   the most important thing to make sure a company goes public. But you’ve   
   proved a political person is just as important.” Lehane, however, had   
   had an even bigger insight. These campaigns had revealed that tech   
   companies—particularly firms, like Airbnb, with platforms that connect   
   people who might otherwise have trouble finding one another—were now   
   potentially the most powerful cohort in politics. “At one point,   
   organizations like labor or political parties had the ability to   
   organize and really turn out large numbers of voters,” Lehane told me.   
   Today, Internet platforms have the bigger reach; a tech company can   
   communicate with hundreds of millions of people by pushing a button.   
   “If Airbnb can engage fifteen thousand hosts in a city, that can have   
   an impact on who wins a city-council race or the mayoralty,” Lehane   
   told me. “In a congressional or Senate race, fifty thousand votes can   
   make all the difference.” Of course, simply having a huge user base   
   doesn’t guarantee that Airbnb can get everything it wants. Voters   
   respond only to enticements that they find persuasive. But companies   
   like Airbnb, Lehane understood, could make arguments faster, and more   
   efficiently, than nearly any political party or other special-interest   
   group, and this was a source of considerable power. “The platforms are   
   really the only ones who can speak to everyone now,” Lehane said.   
      
   For the tech industry, the Trump years were a bewildering mess. The   
   President attacked tech platforms for being biased against   
   conservatives, and liberals railed against Silicon Valley’s social-   
   media companies for propelling Trump into the White House. Tech   
   executives declared their support for the industry’s many immigrants in   
   the face of Trump’s Muslim ban and border separations; they also   
   contended with walkouts and protests from employees over racial   
   injustice, sexual harassment, and all-gender bathrooms—subjects that   
   neither an engineering degree nor business school had prepared them   
   for. When Joe Biden won the Presidency, in 2020, the Valley’s leaders   
   were relieved. The Biden Administration seemed like a return to the Pax   
   Obama, an era when tech was considered cool and politicians boasted of   
   knowing Mark Zuckerberg. Biden’s victory also meant that Lehane, with   
   his deep roots in the Democratic Party, was unquestionably Silicon   
   Valley’s top political guru. Companies sought him out; employees loved   
   that he was generous with credit and made politics fun. (Many former   
   colleagues talk proudly about the nicknames that he bestowed upon   
   them.) Most of all, he made the people he worked with feel like they   
   were on a righteous quest. Peter Ragone, a prominent adviser to   
   numerous Democratic politicians, told me that, among the handful of   
   political consultants transforming Silicon Valley, “Chris is the tip of   
   the spear. His capacity for processing information at speed is   
   breathtaking.”   
      
   The Valley’s enthusiasm for Biden, however, was short-lived. The   
   President quickly appointed three prominent tech skeptics—Gary Gensler,   
   Lina Khan, and Jonathan Kanter—to oversee the Securities and Exchange   
   Commission, the Federal Trade Commission, and the antitrust division of   
   the Department of Justice, respectively. Soon the government was suing   
   or investigating Google, Apple, Amazon, Meta, Tesla, and dozens of   
   other companies. Some of those suits and inquiries had been initiated   
   under Trump, but Biden’s S.E.C. found a particular target in the   
   cryptocurrency industry. Gensler, an ally of Elizabeth Warren, filed   
   more than eighty legal actions arguing that crypto firms or promoters   
   had violated the law, most often by selling unregistered securities.   
   Some of the executives being sued by the S.E.C. had contributed   
   lavishly to the Democrats. Brad Garlinghouse, the C.E.O. of the crypto   
   firm Ripple, who had been a fund-raising bundler for Obama, was among   
      
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