Jonathan Weber, with his new book City on the Edge. Ed Ritger

The Bay Area’s ties to the tech industry go back a long way. But starting in the early 1990s, high tech began to spawn companies and disruptors and new tech moguls right here in San Francisco. The industry’s sometimes contentious relationship with San Francisco residents and its political class is told in the new book City on the Edge: Technology, Politics, and the Fight for the Soul of San Francisco, by Jonathan Weber.

Weber, whose background includes editing The Industry Standard, the San Francisco Standard, and other publications not called “Standard,” talked to The Voice about the booms and busts, the unique culture of San Francisco, and how it became inescapably married to the highest of high tech.

My entrance into tech journalism was as an editor at Internet World magazine in New York around the turn of the century; it exemplified the New York–San Francisco differences. We did not hold parties on the roof, we didn’t do drugs in the basement, we didn’t treat work as an interruption to a nonstop party. In the first section of your book, you give a fascinating tour of what was happening in the San Francisco media scene from 1990 to 2001. When you were in the midst of it, did you think it was a “new normal” or did it feel like this could be a fleeting moment in time?

It’s fair to say that it did feel like a fleeting moment. We warned in the magazine quite often that this is probably a bubble, and that the bubble is going to burst, and this isn’t going to go on forever. In that respect, I think that intellectually we were eyes-wide-open about what was going on. I think emotionally it’s actually harder to really internalize that. So even though we kind of knew it wouldn’t go on forever, we sort of acted like it would, I guess. That’s somewhat a normal human reaction, but I also do fault myself a little bit for not anticipating a little bit better what was going to happen when the bubble burst. 

Do you think if San Francisco had been on sounder economic ground as each of these waves of tech came through that city leaders might have handled it better?

Yeah, I think that’s a good observation. The booms and busts are kind of hard to deal with from a sort of civic governance standpoint. The city was often a little sort of whiplashed from the last thing that happened. So it was difficult for the city to really understand what was happening quickly enough to try to get ahead of some of what was to come. If there’s one thing that the city didn’t do that it really should have done many years ago is to confront the housing issue; the downzoning in 1978 really severely depressed housing production in the city for many decades, and nobody really wanted to take that on. That I think is part of what produced problems that we had through the boom period and have again in spades now with the AI boom.

A civic leader in San Jose [has] talked about how San Jose has a very strong tradition of groups working together on projects for the city, [but] said San Francisco does not. What had been here — the famous wealthy families — that seems to be changing. You had some really insightful stuff in your book about how [the tech moguls] are not wedded to the city the way that previous moguls were.

That’s right. San Francisco definitely used to have that kind of alliance between the big downtown companies and the city. There used to be something called the Committee on Jobs, there was another group even that preceded that. One person I talked to, a guy named Rudy Nothenberg, who’s now in his 90s, but he had been a prominent senior political aide to [Dianne] Feinstein and to Willie Brown. Rudy talked about how back in the ’70s and the ’80s, the big downtown companies [were more involved]. He recalled Transamerica Corporation ran a whole management training program for a bunch of people in the city, that kind of stuff. There was really a much tighter relationship between these old-line industries and the city. 

Warren Hellman — who I worked for at The Bay Citizen, he was the founder of The Bay Citizen — was a private equity mogul, and he was in a sense the last of the old downtown business leaders. He represented that sort of old guard of the banks and the big corporations. He brokered a deal between the city and the public employee unions over the pension plan, which was an unusual thing for a private citizen to do. He was an influential guy and represented that kind of spirit. But then Warren died prematurely in 2011. At the same time, these old-line companies, a lot of them were moving out. Bank of America, Wells Fargo, Schwab, Chevron, either moving to the suburbs or moving to Texas. 

Then of course you have the tech companies rising up, and the tech companies really did have — by nature almost and by the era that they arose — a very different kind of relationship with the city. First of all, there’s nothing very geographically centric about most internet companies. These companies can be located anywhere. 

But at the same time, what you see sometimes now is corporate leaders — well, they get really interested, but then they kind of lose interest. Marc Benioff was a champion of the city and backer of many things and he’s, to his credit, given a lot of money to hospitals and other things. But now it seems like he’s lost interest a bit. He spends most of his time in Hawaii. It’s kind of a good example. A lot of these moguls don’t really live in a place in the same way that would’ve been normal 30 or 40 years ago. 

Was it British Prime Minister [Theresa] May who referred to “citizens of nowhere”?

Yeah, that’s right.

In your book, you relate how psychedelic drugs played a role from many of the early creators of the internet scene in San Francisco. It seems kind of ironic considering the devastation that drugs have fueled in the Tenderloin and elsewhere in the city in recent decades. What role do you think that permissive attitude toward hard drugs played in creating or not stopping the current situation?

I think it was very linked. As I described in the book, there was a strong affinity between a lot of the early internet community and the rave community and some of the music community, and psychedelic drugs were very much part of that scene. So the fact that San Francisco was a place that was open to that, had a permissive and tolerant attitude toward drugs in general, I think that was a positive from the point of view of a lot of people involved in tech. Generally, I would draw a distinction between psychedelic drugs and fentanyl or different things, but I do think that the kind of attitude and the tolerance of the city and the kind of even approval, I guess, of certain kinds of drug use, that that is definitely part of what made the city appealing to people who wanted to do fentanyl basically or to do other kinds of drugs that were really very damaging to themselves and to people around them.

… The city just doesn’t have the appetite for putting people in jail for drug use, and that has a long historical tradition here.

Nowadays, Austin, Tex., seems to be weird enough to attract Bay Area tech companies and their weird overlords, and Texas even has tax policies they like, too. Considering the Texas option, is the AI boom perhaps the last hurrah for San Francisco’s kind of vaunted matchup of creativity and tech booms?

I guess the short answer would probably be no, based on the dynamics of the AI boom. I’m going to be a bit of a homer here, but despite the aspirations of Austin and Miami, those places are not even on the map in AI relative to San Francisco. If you ask which city is ahead of AI, it’s like San Francisco by orders of magnitude. 

The thing I find quite fascinating actually is that the AI industry was planting its roots deeply in San Francisco right at the moment of the worst of the doom loop in 2022 and 2023, when everyone was saying San Francisco is dead and we’re all going to move to Austin or Miami or New York or whatever. At that very moment, not only was OpenAI and Anthropic planting themselves even further in San Francisco, but I thought it was extremely telling that Garry Tan, when Y Combinator reopened after the pandemic, they opened in San Francisco, even though Y Combinator previously had been in Mountain View. So they moved to San Francisco at the deepest part moment of the doom loop. 

I think that the idea that San Francisco is going to lose its leadership — I don’t really see that. It’s very hard to tell what will come after the AI boom, but I don’t really see that. It’s going to retain its leadership of the AI industry. I think the bigger question is whether it can retain the special culture. And this goes to your question: Can it retain the special culture, which then presumably nurtures all the booms going forward? Even though the city has come back in dramatic ways, it’s also the case that a lot of the street life, social life, cultural life is still not what it was at all.

John Zipperer is the editor at large of The Voice of San Francisco. He has 30 years of experience in business, technology, and political journalism. John@thevoicesf.org