“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 The ordinary folks of San Francisco have been replaced by a new class of tech bros.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%. In 1992: 2% of SF workers in tech. By 2019: 35%. Economically troubled city, post-earthquake, post-AIDS. A group of free-thinking technologists immersed in the counterculture invented the contemporary internet. One of the most rapid urban transformations in American history.

• The Cacophony Society and Burning Man. Before the boom: extraordinary underground culture. The Cacophony Society — anarchic free spirits, Situationist pranks, urban exploration — effectively founded Burning Man. That anarchic spirit was the soul of the city too.

• The City of Nostalgia. People arrive with a fixed idea of what San Francisco is. It inevitably becomes something different. The gap generates permanent mourning. Intensified here by the height of the hopes people bring. The city means something bigger than itself.

• The AI Boom and the Coming IPO Earthquake. OpenAI and Anthropic both based in the city. When those IPOs happen, real estate goes really, really crazy again. The city is gradually becoming uniformly wealthy. The cycles are not over.

• Burning Man and the Future of Cities. The internet arrived on the playa and Burning Man lost the sense of being a separate world. Cities 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?

About the Guest

Jonathan Weber is a veteran technology journalist and the author of City on the Edge (Atria Books, June 9, 2026). Former editor-in-chief of The Industry Standard and the San Francisco Standard. He lives in San Francisco.

References

City on the Edge by Jonathan Weber (Atria Books, June 9, 2026): simonandschuster.com/books/City-on-the-Edge/Jonathan-Weber/9781668074916
David Talbot, Season of the Witch
Ezra Klein and Derek Thompson, Abundance

About Keen On America

Nobody asks more awkward questions than the Anglo-American writer and filmmaker Andrew Keen.

Website: https://keenon.tv/ Substack: https://keenon.substack.com/ YouTube: https://youtube.com/@KeenOnShow

Chapters:

00:00:30 Andrew at Mount Olympus, San Francisco
00:02:36 Does San Francisco have a soul?
00:03:29 Vertigo and the city of nostalgia
00:05:11 2% to 35%
00:05:33 What SF was like before tech
00:07:35 The Cacophony Society and Burning Man
00:57:10 The AI boom and the IPO earthquake
00:59:24 Could SF become a human-less city?
01:00:52 Burning Man and the future of c