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City on the Edge: Technology, Politics, and the Fight for the Soul of San Francisco
An “absorbing” (San Fransico Chronicle) and “fascinating” (Financial Times) account of San Francisco’s meteoric transformation into a global capital of technology, and how the same creative and political forces that gave rise to its boom now threaten to destroy what made it great.
At the dawn of the 1990s, San Francisco was a beautiful if troubled mid-sized metropolis. It was still reeling from the AIDS epidemic and the Lome Prieta earthquake, its economy stuck in a post-industrial slump. Once considered to be the capital of the American West, and later the beating heart of the global counterculture, the mythic, fog-shrouded city at the edge of the continent faced an uncertain future.
But in that very moment, a band of free-thinking technologists, immersed in the creative zeitgeist of the city, were inventing the contemporary internet. San Francisco would undergo an epic political, social, and economic transformation as it claimed the title of tech capital of the world. Local politicians, including Gavin Newsom and Kamala Harris, advanced to the national stage. An unlikely marriage of underground culture and technological optimism gave rise to the annual reverie known as Burning Man.
This should have been a happy story for San Francisco. But as the city’s tech economy roared, a host of urban ills lurked in the homelessness, drug addiction, mental illness, and a crippling lack of new housing. The city’s famously left-wing political establishment struggled to get its arms around the problems. When the pandemic arrived in 2020, it created new crises and laid old ones bare, shattering a “City Family” that had ruled politically for more than thirty years. Key leaders of the once-liberal tech industry turned sharply to the right, embracing President Trump and his war on “San Francisco values” just as the artificial intelligence revolution began to produce yet another massive financial boom.
Jonathan Weber saw it all up close as a reporter and newsroom leader. He offers a sweeping history of a city that rose to dizzying heights in the internet era, only to be battered by the heedlessness of a tech industry it did so much to spawn and politicians who had lost the plot. Drawing on 200 interviews with mayors, CEOs, political leaders, activists, entrepreneurs, and artists, City on the Edge is more than a simple chronicle of a city. It’s the story of a war waged for the heart of San Francisco—one that anticipated the culture wars raging around the world. As the AI boom revs up, with San Francisco as its undisputed capital, the conflicts are playing out yet again, and will have an impact far beyond the city’s famed Golden Gates.
At the dawn of the 1990s, San Francisco was a beautiful if troubled mid-sized metropolis. It was still reeling from the AIDS epidemic and the Lome Prieta earthquake, its economy stuck in a post-industrial slump. Once considered to be the capital of the American West, and later the beating heart of the global counterculture, the mythic, fog-shrouded city at the edge of the continent faced an uncertain future.
But in that very moment, a band of free-thinking technologists, immersed in the creative zeitgeist of the city, were inventing the contemporary internet. San Francisco would undergo an epic political, social, and economic transformation as it claimed the title of tech capital of the world. Local politicians, including Gavin Newsom and Kamala Harris, advanced to the national stage. An unlikely marriage of underground culture and technological optimism gave rise to the annual reverie known as Burning Man.
This should have been a happy story for San Francisco. But as the city’s tech economy roared, a host of urban ills lurked in the homelessness, drug addiction, mental illness, and a crippling lack of new housing. The city’s famously left-wing political establishment struggled to get its arms around the problems. When the pandemic arrived in 2020, it created new crises and laid old ones bare, shattering a “City Family” that had ruled politically for more than thirty years. Key leaders of the once-liberal tech industry turned sharply to the right, embracing President Trump and his war on “San Francisco values” just as the artificial intelligence revolution began to produce yet another massive financial boom.
Jonathan Weber saw it all up close as a reporter and newsroom leader. He offers a sweeping history of a city that rose to dizzying heights in the internet era, only to be battered by the heedlessness of a tech industry it did so much to spawn and politicians who had lost the plot. Drawing on 200 interviews with mayors, CEOs, political leaders, activists, entrepreneurs, and artists, City on the Edge is more than a simple chronicle of a city. It’s the story of a war waged for the heart of San Francisco—one that anticipated the culture wars raging around the world. As the AI boom revs up, with San Francisco as its undisputed capital, the conflicts are playing out yet again, and will have an impact far beyond the city’s famed Golden Gates.
432 pages, Kindle Edition
Published June 9, 2026
About the author
Jonathan Weber
1 book11 followersJonathan has been covering technology and politics for more than thirty years as a reporter, editor, newsroom leader and journalism entrepreneur.
After a stint in the technology trade press that included a posting in Paris, in 1990 he was named the first Silicon Valley correspondent for the Los Angeles. He subsequently served as co-founder and editor in chief of The Industry Standard, a weekly news magazine that became a symbol of the dot-com boom of the late 1990s. In 2005, as independent online media was beginning to take shape, he launched a local and regional online magazine called New West, serving the Rocky Mountain West. He then returned to San Francisco as the founding editor of The Bay Citizen, a non-profit news organization devoted to Bay Area news.
Later he served as West Coast Bureau chief and Global Technology editor for Reuters News, and then was the founding editor of another local news organization, the San Francisco Standard. He holds a BA in Philosophy from Wesleyan University.
After a stint in the technology trade press that included a posting in Paris, in 1990 he was named the first Silicon Valley correspondent for the Los Angeles. He subsequently served as co-founder and editor in chief of The Industry Standard, a weekly news magazine that became a symbol of the dot-com boom of the late 1990s. In 2005, as independent online media was beginning to take shape, he launched a local and regional online magazine called New West, serving the Rocky Mountain West. He then returned to San Francisco as the founding editor of The Bay Citizen, a non-profit news organization devoted to Bay Area news.
Later he served as West Coast Bureau chief and Global Technology editor for Reuters News, and then was the founding editor of another local news organization, the San Francisco Standard. He holds a BA in Philosophy from Wesleyan University.
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Displaying 1 - 15 of 15 reviews
July 27, 2026
Jonathan Weber has written an interesting book on aspects of the political history of San Francisco from 1990 to 2024 with a focus on the technology industry. He has been involved as a technology reporter and editor for various publications during this period.
While the rise of the technology industry has been centered to the south of San Francisco in what is now called “Silicon Valley,” the city has played a significant role. At first, it was essentially a bedroom community for tech workers who commuted to their companies down the peninsula. This gave rise to much reported unhappiness of some San Francisco residents with the luxury buses the tech companies hired to ease the commute of their workers. Subsequently, some tech companies came to the city or increased their presence there. Weber singles out Twitter, which was given a tax break to locate in an area near the San Francisco Civic Center (it has since vacated that property after it became “X”).
San Francisco’s downtown suffered from Covid-19 and its aftermath, as tech workers enjoyed the convenience of working from anywhere. Notably, San Francisco’s downtown has been slower to recover from the pandemic than the business districts of other major U.S. cities. Now the AI boom has been giving an economic boost to the city, and I am told that downtown is in the process of recovering.
There is much more to the book than I have summarized here, and for those interested in the San Francisco tech story and its reverberations on the politics of the city, which are much more complicated than simply liberal politics, this book provides a lot of information, some of which is based on the author’s direct experiences. However, if one is looking for an informed discussion of the “soul of San Francisco,” this book may be a start but it is limited.
The limitation is made obvious by the map at the beginning of the book, which is only of a slice of the city in the northeast, including the downtown area. San Francisco is small in land area, but there is much more to the city than this.
Amazingly, the book, which at times digresses from the tech story, does not even cover some significant history of the downtown area. For example, there is no mention of Chevron, once a large employer in San Francisco, moving its headquarters from the city to San Ramon, which is about 40 miles away and inland from the southeast portion of the Bay. (Since then, Chevron moved its headquarters out of California entirely, to Houston in 2024.) Also, missing from the book is the move of Bechtel’s headquarters out of San Francisco to Reston, Virginia, in 2024. (Bechtel, a large, privately-held engineering firm once headed by George Shultz, also moved its operations in Houston to Reston.)
These companies’ departure from the city and their effective replacement by the tech industry is an important part of the story that is missing. In addition, while the largest employer in San Francisco, the city and county itself, is discussed, the next largest current employer, the University of California, San Francisco, is not. UCSF is a medical school and owner of several hospitals and affiliated medical services. It is only mentioned in passing for its expansion into the new Mission Bay development. Also, Dr. Bob Wachter, the head of UCSF’s Department of Medicine, who was a prominent user of Twitter and webcasts during the pandemic, is quoted about Covid.
In discussing the business environment of San Francisco, the author also does not mention the significant financial industry. While NationsBank bought BankAmerica in 1998 and the headquarters of the combined company now called Bank of America went to Charlotte, North Carolina, there remains a significant financial industry presence in San Francisco along with the Federal Reserve Bank of San Francisco (where I briefly worked a long time ago).
The problem is that the author has lived and breathed tech, and ignored much of what else has been happening in San Francisco. The large Asian population (primarily Chinese), with concentrations in Chinatown, the large Sunset area which borders Golden Gate Park to the north and ends at the Pacific Ocean on the west, and also to an extent in the Richmond, which parallels the Sunset on the north of Golden Gate Park, is not much discussed. This group is important and has become an important political force. The diversity of the population, including Hispanics, and those with Russian, Italian, Irish, and other backgrounds, as well as the declining population of African-Americans, is absent from the book. Also not much discussed is the significant influence of the gay community on San Francisco politics and culture. The southern sections of the city, much of which are not the pretty version which figure in postcards, are also not mentioned. In other words, San Francisco, a relatively small city (the fourth largest in population in California) though effectively the center of the much larger Bay Area, is a complicated place with a diverse population and a colorful history. While the tech industry is important, you need to look beyond the tech industry and the book’s much discussed Burning Man festivals, to understand San Francisco, not to mention its soul.
While the rise of the technology industry has been centered to the south of San Francisco in what is now called “Silicon Valley,” the city has played a significant role. At first, it was essentially a bedroom community for tech workers who commuted to their companies down the peninsula. This gave rise to much reported unhappiness of some San Francisco residents with the luxury buses the tech companies hired to ease the commute of their workers. Subsequently, some tech companies came to the city or increased their presence there. Weber singles out Twitter, which was given a tax break to locate in an area near the San Francisco Civic Center (it has since vacated that property after it became “X”).
San Francisco’s downtown suffered from Covid-19 and its aftermath, as tech workers enjoyed the convenience of working from anywhere. Notably, San Francisco’s downtown has been slower to recover from the pandemic than the business districts of other major U.S. cities. Now the AI boom has been giving an economic boost to the city, and I am told that downtown is in the process of recovering.
There is much more to the book than I have summarized here, and for those interested in the San Francisco tech story and its reverberations on the politics of the city, which are much more complicated than simply liberal politics, this book provides a lot of information, some of which is based on the author’s direct experiences. However, if one is looking for an informed discussion of the “soul of San Francisco,” this book may be a start but it is limited.
The limitation is made obvious by the map at the beginning of the book, which is only of a slice of the city in the northeast, including the downtown area. San Francisco is small in land area, but there is much more to the city than this.
Amazingly, the book, which at times digresses from the tech story, does not even cover some significant history of the downtown area. For example, there is no mention of Chevron, once a large employer in San Francisco, moving its headquarters from the city to San Ramon, which is about 40 miles away and inland from the southeast portion of the Bay. (Since then, Chevron moved its headquarters out of California entirely, to Houston in 2024.) Also, missing from the book is the move of Bechtel’s headquarters out of San Francisco to Reston, Virginia, in 2024. (Bechtel, a large, privately-held engineering firm once headed by George Shultz, also moved its operations in Houston to Reston.)
These companies’ departure from the city and their effective replacement by the tech industry is an important part of the story that is missing. In addition, while the largest employer in San Francisco, the city and county itself, is discussed, the next largest current employer, the University of California, San Francisco, is not. UCSF is a medical school and owner of several hospitals and affiliated medical services. It is only mentioned in passing for its expansion into the new Mission Bay development. Also, Dr. Bob Wachter, the head of UCSF’s Department of Medicine, who was a prominent user of Twitter and webcasts during the pandemic, is quoted about Covid.
In discussing the business environment of San Francisco, the author also does not mention the significant financial industry. While NationsBank bought BankAmerica in 1998 and the headquarters of the combined company now called Bank of America went to Charlotte, North Carolina, there remains a significant financial industry presence in San Francisco along with the Federal Reserve Bank of San Francisco (where I briefly worked a long time ago).
The problem is that the author has lived and breathed tech, and ignored much of what else has been happening in San Francisco. The large Asian population (primarily Chinese), with concentrations in Chinatown, the large Sunset area which borders Golden Gate Park to the north and ends at the Pacific Ocean on the west, and also to an extent in the Richmond, which parallels the Sunset on the north of Golden Gate Park, is not much discussed. This group is important and has become an important political force. The diversity of the population, including Hispanics, and those with Russian, Italian, Irish, and other backgrounds, as well as the declining population of African-Americans, is absent from the book. Also not much discussed is the significant influence of the gay community on San Francisco politics and culture. The southern sections of the city, much of which are not the pretty version which figure in postcards, are also not mentioned. In other words, San Francisco, a relatively small city (the fourth largest in population in California) though effectively the center of the much larger Bay Area, is a complicated place with a diverse population and a colorful history. While the tech industry is important, you need to look beyond the tech industry and the book’s much discussed Burning Man festivals, to understand San Francisco, not to mention its soul.
July 23, 2026
What a phenomenal book. It’s incredibly thorough and well documented. The author manages to remain neutral even when confronting highly charged political subjects that are divisive in the city. Having lived the Twitter story I thought he did a phenomenal job at capturing Del Harvey’s tenure and the Public Policy team’s efforts in the Tenderloin (not to mention the complex leadership dynamics). This book should be a mandatory read for civic minded San Franciscans. Absolutely fantastic.
July 30, 2026
I picked an advance reader copy of this up for free in the library and glad I did. It initially appealed to my interests in urban studies but it delivered a whole lot more. This is essentially a close up look at the last 35 years or so (the Internet era) of San Francisco history, a history that includes architectural and infrastructure development, politics, economics and cultural trends. The author is a journalist who covered the city’s development over that time span and he does a great job presenting many angles on the issues. Though many of the book’s characters are still very much in the news today, the narrative gives a historic context to the city’s many recent ups and downs.
August 4, 2026
This book is an engaging and readable but narrow journalistic account of the ups and downs of San Francisco since 1990. The author spends a lot of time on his own journalistic career, which is not that interesting, as well as the media industry in SF. But the two main focuses are business, especially tech, and city politics. Some good coverage of culture as well, including an account of the Burning Man phenomenon and how it fits into the story of the city.
September 4, 2026
Having lived in San Francisco and worked in Silicon Valley since 1987, the material in this book should have been old news, and a lot of it was. But there was enough new to me to make the book worthwhile, and for a non-techie, most of it would be illuminating. What it is not (why I took away a star) is depth--the author makes a quick connection between business and politics and then quickly moves on to the next big thing without giving us a deeper understanding of the relationships between those systems. The focus is on technology and the tech culture in SF and the reaction of the political and cultural system to it, but it doesn't look much at things like neighborhood transitions, serious political battles, and the deeper corruption and ineptitude of San Francisco governance (whether by actual government or by the systems that actually make things work, such as drug dealing, gentrification/development, and cultural conflict. What is clear by the end of the book is that San Francisco is changing. But he emphasizes the conservative shift too much. Casting Willy Brown as a "progressive" for example, and seeing him as the behind-the-scenes power behind the throne up to the present--not true. The only even possibly progressive mayor during this period was Art Agnos, and, well, yeah. He's much too kind to the homelessness nonprofit world, which I've found totally counterproductive as a homeowner in SF. Serial fail. That said, traveling to other cities, the homelessness is widespread across America, and saying SF is qualitatively different just doesn't work for me. Here is where the superficial approach of the book breaks down, because it doesn't really give a clear picture of the awful complexity of the problems involved. The conclusion is not earned by his evidence. I'll leave Burning Man as a phenomenon alone, having seen the Smithsonian exhibition. How much that's a part of San Francisco is for someone else to say, I'm not a burner. And he only mentions Phil Ginsburg's park contribution once, for the skateboard park in UN plaza--inspired, but only one of many stunning park improvements made by the man. Most effective city employee ever, in my opinion. Nothing I've read in the book shakes the basic conclusion I've held since moving here in 1967 as a teenager--SF is a city that constantly changes in fundamental ways, and being a NIMBY, progressive or conservative, is to guarantee the City will break your heart. Get used to it, SF.
September 23, 2026
This book offers a lot of detail and insights into San Francisco and the growing influence of the tech industry on the city, and vice versa. It cover major events and personalities from the rise of the Internet and its impact on the economy and society up until the beginning of the AI era. I lived in San Francisco for part of this time period, 1997-2007. Overall, this is a solid background read to get some idea of what was going on in/around the City during this time period as it relates to SF culture and tech, as well as politics. As the author points out, they are all entwined. Weber has a clear take on how the counterculture that's native to San Francisco influenced the growth of the tech industry, and its wayward turn to the right as the AI era dawned. Only in SF and the surrounding communities could tech have developed the way it did. I did find that the author jumped around quite a bit and there are so many personalities that come and go throughout the book that it was a little hard to keep them all straight. But this is an informed and solid take on the topics he covers.
November 10, 2026
Solid chronicling of recent San Francisco history. I appreciated the focus on just SF and not the rest of the Bay Area.
My main criticism is that the authors’ moderate democratic political leaning definitely colors his narrative of more recent events. As someone who works in city politics I could tell based on his sources and some comments what he thought of certain politicians/policy choices. He definitely was still critical but I think could have done a better job of telling the progressive side and focused more on the story of working class and poor San Franciscans. I also think too much attention was spent on the minute details of Burning Man. I didn’t feel like that came back around in the end as relevant for anything.
Totally worth the read for anyone interested in why SF is the way it is right now!
My main criticism is that the authors’ moderate democratic political leaning definitely colors his narrative of more recent events. As someone who works in city politics I could tell based on his sources and some comments what he thought of certain politicians/policy choices. He definitely was still critical but I think could have done a better job of telling the progressive side and focused more on the story of working class and poor San Franciscans. I also think too much attention was spent on the minute details of Burning Man. I didn’t feel like that came back around in the end as relevant for anything.
Totally worth the read for anyone interested in why SF is the way it is right now!
September 18, 2026
Season of the Witch it is not. City on the Edge picks up chronologically where that book ends and attempts to answer two intertwined questions: How did San Francisco acquire its current problems, and how did the tech boom happen here?
The lines between those stories remain blurred throughout. This is an exceptionally dense book, determined to cover nearly every major piece of San Francisco news from the past 30-plus years and mention seemingly everyone who played a part. It is comprehensive, but often reads more like an exhaustive chronicle than a coherent explanation.
My biggest takeaway was that tech people used to be far less annoying because many of them were genuinely motivated by creative and progressive ideals. Now, far too many are simply capitalist NIMBYs.
The lines between those stories remain blurred throughout. This is an exceptionally dense book, determined to cover nearly every major piece of San Francisco news from the past 30-plus years and mention seemingly everyone who played a part. It is comprehensive, but often reads more like an exhaustive chronicle than a coherent explanation.
My biggest takeaway was that tech people used to be far less annoying because many of them were genuinely motivated by creative and progressive ideals. Now, far too many are simply capitalist NIMBYs.
June 25, 2026
Learned SO much from this book. If you have any curiosity about San Francisco over the last forty years, it is a GEM. As a former SF resident, it also strikes me as an excellent foundation from which to have a mature conversation about "how to fix SF."
The writing is a bit dry, but also commendably objective, given Weber's central place in it all.
The writing is a bit dry, but also commendably objective, given Weber's central place in it all.
July 12, 2026
Good examination of the tech boom in SF in the 90s to now. Especially interested in how the early 90s culture of Cacophony Society/Burning Man entertwined with the tech boom, having been on the periphery of that at the time. Made clear several things that I wasn't aware of earlier or had suspected but not confirmed.
September 21, 2026
This book is a very interesting tale of the city of San Francisco and its politics over the past several decades. The level of detail was excellent. Unfortunately it bogged down from time to time, and included WAY TOO MUCH info about Burning Man. That said, I enjoyed and learned a lot.
September 23, 2026
If you are interested in the sf tech story you’ll love this 14 hour to listen to book. I did
October 6, 2026
review tk
October 14, 2026
You can't write about SF without a deep dive into politics, however, you don't have to let your own political beliefs flavor your description of each political issue.
July 23, 2026
As someone who has spent the majority of their adult life in San Francisco and the Bay Area I really enjoyed reading this book.
It gives a strong overview of the last 30 years from a political standpoint with an emphasis on how tech has transformed the city and on the different waves of tech.
It also spends considerable time on Burning Man - a subject close to my heart.
The author is quite liberal which fits the city but sometimes his one sided view of things is bothering - for example he saw San Francisco’s response to COVID as heroic without dealing with any of the downsides of that response and his only explanation for the rise of republicans is greed. However the sheer joy of reading it overshadowed those concerns.
It gives a strong overview of the last 30 years from a political standpoint with an emphasis on how tech has transformed the city and on the different waves of tech.
It also spends considerable time on Burning Man - a subject close to my heart.
The author is quite liberal which fits the city but sometimes his one sided view of things is bothering - for example he saw San Francisco’s response to COVID as heroic without dealing with any of the downsides of that response and his only explanation for the rise of republicans is greed. However the sheer joy of reading it overshadowed those concerns.
Displaying 1 - 15 of 15 reviews