“The same creative and political forces that gave rise to [San Francisco’s] boom nearly engineered its collapse.” — Jonathan Weber
In Hitchcock’s Vertigo, the quintessential San Francisco movie, the villain points to an old painting of the city and tells Jimmy Stewart that San Francisco has changed. The real city has been lost, he says. Somebody has stolen San Francisco’s soul.
The veteran tech journalist Jonathan Weber is the latest writer to search for that soul. In City on the Edge: Technology, Politics, and the Fight for the Soul of San Francisco, Weber bemoans the disappearance of the real San Francisco — the city not just of the Beats and the Counterculture but also of ordinary teachers and policemen. We’ve had thirty years of boom, bust, and Big Tech. The ordinary folks of San Francisco have been replaced by a new class of tech bros.
In 1992, just 2% of San Franciscans worked in tech. By 2019 it was 35%. As a longtime San Franciscan, Weber had a front-row seat on the dot-com mania, the rise of social media, Uber and Airbnb, the pandemic’s great emptying of downtown, and now the AI boom driven by the San Francisco-based Anthropic and OpenAI. In City on the Edge, Weber argues that the same creative and political forces that gave rise to the boom — the counterculture’s anarchic spirit, the city’s love affair with eccentricity, the tech industry’s utopian self-belief — also engineered its near-collapse. Digital vertigo, so to speak. Once again somebody has stolen San Francisco’s soul.
Five Takeaways
• From 2% to 35%: The Numbers Behind the Transformation: In 1992, just 2% of San Francisco workers were in tech. By 2019 it was 35%. The book traces how this happened: a city economically troubled in the early 1990s, still reeling from AIDS and the 1989 Loma Prieta earthquake, with its manufacturing base gone and its corporate headquarters thinning out. Into this vacuum came a group of free-thinking technologists immersed in the city’s creative counterculture. They invented the contemporary internet. What followed was one of the most rapid urban transformations in American history.
• The Cacophony Society and the Founding of Burning Man: Before the tech boom, San Francisco in the early 1990s had a remarkable underground culture. Weber writes about the Cacophony Society — the group of anarchic free spirits who effectively founded the Burning Man festival. The Cacophony Society emerged from the counterculture of the 1960s through various evolutions — Situationist pranks, urban exploration, radical creativity. Burning Man began as their annual trip to the Black Rock Desert. The spirit of that founding: go somewhere, build something, be someone different, leave no trace. That spirit was the soul of the city too.
• The City of Nostalgia: Always Believing Yesterday Was Better: Weber takes his Vertigo reference seriously. San Francisco is structurally a city of nostalgia — people arrive with a fixed idea of what the city is, and it inevitably becomes something different. The gap between the idea and the reality generates permanent mourning. This is not unique to San Francisco — Trump has built a presidency on the idea that things were better in the 1950s — but it is intensified here by the height of the hopes people bring. The city means something bigger than itself. That is both its greatest asset and its permanent wound.
• The AI Boom and the Coming IPO Earthquake: The current AI boom is, in Weber’s reading, likely to be the largest yet. OpenAI and Anthropic are both based in the city. When those IPOs happen, San Francisco real estate — already rising 25–50% in some neighbourhoods, Andrew notes — will go, in Weber’s words, “really, really crazy again.” Hundreds of thousands of millionaires will be created overnight. The city is gradually becoming uniformly wealthy. Some of the old tensions may be less intense for that reason. But Weber does not think the cycles are over. The current boom will bust, as all booms do. What comes next is the question.
• Burning Man, the Internet, and the Future of Cities: Weber ends the book at Burning Man. His closing observation: when the internet arrived on the playa, Burning Man lost the sense that it was a separate world — a place where you could be a different person, because nothing from your regular life could reach you. Now everyone has a phone. The privacy is gone. The sense of separation is gone. For cities: part of the power of cities is that they bring people together, and good things arise from that friction. But if technology no longer requires you to be in the same place, cities become less essential. What is the future of the city in the age of technology? Weber doesn’t have a tidy answer. Neither does anyone else.
About the Guest
Jonathan Weber is a veteran technology journalist and the author of City on the Edge: Technology, Politics, and the Fight for the Soul of San Francisco (Atria Books, June 9, 2026). He was the founding editor-in-chief of The Industry Standard, former editor-in-chief of the San Francisco Standard, and covered the technology industry for the Los Angeles Times. He lives in San Francisco.
References:
• City on the Edge: Technology, Politics, and the Fight for the Soul of San Francisco by Jonathan Weber (Atria Books, June 9, 2026).
• David Talbot, Season of the Witch: Enchantment, Terror, and Deliverance in the City of Love — referenced in the conversation; Weber’s recommended companion read on 1970s San Francisco.
• Ezra Klein and Derek Thompson, Abundance — referenced in the closing exchange.
• Joan Didion, Slouching Towards Bethlehem — the opening epigraph to Weber’s book, referenced in the conversation.
• Alfred Hitchcock, Vertigo (1958) — Andrew’s reference; the film’s own meditation on San Francisco as a city of nostalgia.
About Keen On America
Nobody asks more awkward questions than the Anglo-American writer and filmmaker Andrew Keen. In Keen On America, Andrew brings his pointed Transatlantic wit to making sense of the United States — hosting daily interviews about the history and future of this now venerable Republic. With nearly 2,900 episodes since the show launched on TechCrunch in 2010, Keen On America is the most prolific intellectual interview show in the history of podcasting.
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