In San Francisco, the crown jewel of Silicon Valley, there are no poor neighborhoods, just poor people. Squeezed between million-dollar apartments and Michelin-starred restaurants is a rising tide of homelessness: vagrants begging for scraps from the tech zillionaires on Market Street, families who couldn’t afford the rent after the latest IPO, Uber drivers sleeping in their cars in the Safeway parking lot. The nouveau wealth capital of America is a land of decadence and irony, where Juul (banned from selling e-cigarettes in the county) just bought a $400 million office tower and Vinod Khosla thinks he owns the beach. Further down the 101 in Menlo Park and Sunnyvale, Facebook and Google employees are raising their kids tech-free.

This is the world the smartphone has built. In 1994, Vanity Fair inaugurated the New Establishment list to celebrate the rise of a new entrepreneurial class that promised—how young we were then!—to “make the world a better place.” They were digital-age whiz kids challenging the old boys club, rebels and hackers getting their first taste of real power. Twenty-five years later, the upstarts are now the establishment, the undisputed titans of America’s second gilded age.

How quickly it all changed. Twitter, which aided the Arab Spring, now abets America’s culture civil war, and its cofounder Jack Dorsey is more concerned with going on silent retreats than silencing Nazis. Mark Zuckerberg, who dreamed of bringing free internet to Africa, spends his days dodging questions about the genocide in Myanmar. Dara Khosrowshahi has righted the amoral culture of Uber but is struggling to squeeze profits from its gig-economy workforce. (For SoftBank leader Masayoshi Son, self-driving cars can’t come soon enough.) WeWork, another of SoftBank’s crown jewels, is struggling to right the ship after the exit of CEO Adam Neumann, whose questionable business stratagems prompted investors to turn skittish and ultimately helped sink the company’s IPO. Even Slack, which was going to save us from the drudgery of work, has merely insinuated drudgery deeper into the fiber of our lives.

Unwinding the problems these entrepreneurs have wrought is difficult, as anyone on the 2019 New Establishment list can attest. YouTube’s Susan Wojcicki has spoken passionately of “trying to strike a balance” between removing hate speech and cultivating free expression but is quick with excuses when pressed on the specifics (“If we were to take down every video…”). Poor Zuckerberg couldn’t for the life of him figure out how to rid Facebook of anti-vaxxers or Russian bots—at least until regulators began threatening multibillion-dollar fines and high-profile tech insiders (including Tristan Harris and Roger McNamee) began speaking publicly about breaking up the company. “Fish don’t see water,” one tech investor explained when I asked how Silicon Valley sees itself in this age of cultural backlash. Another senior-level tech employee, who has worked in the industry for more than a decade, wasn’t so kind. “I don’t think they smell their own shit,” she said.

There is still a sense of wonder: Elon Musk is planning a Mars colony; Satya Nadella is pouring money into artificial intelligence; Larry Page has invested in flying cars. Wojcicki’s younger sister, Anne, is building a genetic database that is already being used to design new drugs (with a $300 million investment from Glaxo­SmithKline) and fuel cutting-edge academic research. Jeff Bezos has teamed up with titans of the financial industry to lower health care costs, while Brian Armstrong’s cryptocurrency exchange, Coinbase, aims to disrupt the financial industry altogether. In Hollywood, technology has forced the studios to compete with Netflix and Amazon, fueling another golden age of video.