Few things have transformed San Francisco in a more dramatic fashion than the rise of the internet. Over the past four decades, the city has spawned some of the world’s most powerful and influential tech companies, from Salesforce and Uber to Airbnb and X. Simultaneously, the area has contended with soaring housing prices, increased gentrification, and an alarming exodus of artists and creative types—matters compounded, and in many ways exacerbated, by all those tech companies setting up shop in the region in the first place.
Jonathan Weber has had a front-row seat to much of this history. In 1990, he was posted in the San Francisco bureau of the Los Angeles Times as the paper’s first Silicon Valley correspondent; eight years later, he became editor in chief of the Industry Standard, one of the most influential and profitable magazines about the internet age before it went belly-up after the dot-com bust of 2000.
Three years ago, Weber began thinking there might be a book in all of this. But the veteran editor and journalist didn’t want to write a memoir, and he thought that a history of the rise of the internet would be “too sprawling.” San Francisco seemed like the perfect frame. In City on the Edge: Technology, Politics, and the Fight for the Soul of San Francisco, Weber takes readers on a compelling ride through the rise and fall and sort-of rise again of the city and its tech industry, intermixing improbable tales of startup successes (a “dank office” in SoMa becomes the birthplace of the hookup juggernaut Match.com; a group of nerds meeting up at the Exploratorium begets Craigslist) with stories of now-forgotten bombs (a dog-walking app; a “roving massage service”). Despite his closeness to the topic, Weber is, by his own admission, a lousy predictor of which tech hopefuls might be the next unicorn or dud. “I’m uniformly terrible at it,” he admits to me over Zoom.
For younger readers, one of the book’s most surprising insights might be just how optimistic people were about the internet in those early days. As Weber reminds us, many of its founders truly believed that it would be a force for positive change. Twitter was going to give power to the people; knowledge on the web would be free and freeing. “There was a sense that you could do well, and also do good,” Weber says.
Weber charts how the city eventually soured on the worst aspects of tech, from the toxic bro culture at Uber, personified in its disgraced CEO Travis Kalanick (who resigned in 2017 after revelations came to light that he ignored rampant sexual harassment at the company), to the controversial Twitter tax break of 2011, which exempted the social media giant from paying millions in payroll taxes to the city. And then there were the infamous Google buses, the employee-only luxury shuttles that became a visible symbol of the city’s expanding gentrification. “They were big, and you’d see the people standing in line for them every day,” Weber says. “And then you might notice, Oh, those people were evicted from that house so some tech guy could renovate that four-unit apartment building into his own mansion.”
The book also reveals the warming ties between the tech companies and city leaders, and how social media platforms like Facebook and Twitter devolved from places supposedly meant to unite humanity to ones that appealed to all the worst impulses of human nature. “I don’t think there’s anything evil per se about social media,” Weber elaborates. “But the way that it has grown up, especially in the case of Facebook, is that it’s been tuned to be a moneymaking engine, and that has led to the creation of mechanisms that encourage bad behavior.”
One of the challenges for readers will be determining who comes off worst: the tech moguls with their billions or the city leaders, many of whom spent much of their careers dogged by accusations of corruption and ethics violations, from Willie Brown to Ed Lee to London Breed. “I would say the heroes of the book are the early internet pioneers,” Weber says. “I have a high regard personally for what those guys accomplished.”
“I don’t think the politicians come off super well,” he adds.
The book ends with the arrival of the COVID-19 pandemic, the collapse of downtown San Francisco’s retail economy, and a wave of layoffs across the city’s biggest tech companies. Much of the worst of it is laid out in a chapter aptly titled “Doom Loop.” So, is San Francisco doomed?
Weber doesn’t think so. “The AI industry has kind of bailed out the city for a moment,” he observes.
But even if AI revives the tech industry’s fortunes, one has to wonder at what cost. Weber expresses concern. “San Francisco is a special place,” he says. “Its identity is built around tolerance and being welcoming to misfits and creative renegades. If you just prioritize the needs of the moneyed and their business, you squeeze out that creative element.”•
CITY ON THE EDGE: TECHNOLOGY, POLITICS, AND THE FIGHT FOR THE SOUL OF SAN FRANCISCO, BY JONATHAN WEBER
CITY ON THE EDGE: TECHNOLOGY, POLITICS, AND THE FIGHT FOR THE SOUL OF SAN FRANCISCO, BY JONATHAN WEBER
Robert Ito is a journalist based in Los Angeles. He writes about film, television, and theater for the New York Times.
