Around the turn of the century, I joined the editorial staff in New York of Internet World magazine, a publication focused—as the name suggests—on all things internet, tailored to a business audience. It was an exciting time to be in publishing, and a great time to be in technology publishing, because the changes and new companies and new technologies were coming fast and furious. (Our parent company was cleaning up on the related Internet World expos, drawing tens of thousands of people to massive trade show floors filled with expensive booths touting companies with services and products ranging from the revolutionary to the ridiculous.)
For the three and a half years I would be with the magazine, eventually becoming its executive editor before the bottom fell out of the tech market, it was a remarkable experience of being able to be in or adjacent to some of the most remarkable ideas and technology the world had seen up to that point. For the last year or so, I had relocated to the San Francisco Bay Area, where we had an office I shared with our veteran West Coast editor. But by that point, things had changed, tech companies had already gone through massive layoffs, and the entire region became an elephant graveyard of former tech behemoths. But if only I had been there a decade earlier . . .
The Bay Area’s ties to the tech industry, nurtured in what were once orchards and then chip factories and are now headquarters for AI giants, go back a long way. But starting in the early 1990s, high tech began to spawn companies and industries and new tech moguls right in San Francisco, where they began to supplant the historic businesses (and business leaders). 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 me about the ups and downs, the booms and the busts, and the unique culture, for better and worse, of San Francisco and how it came to be inescapably married to the highest of high tech.
JOHN ZIPPERER: 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. But 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?
JONATHAN WEBER: 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. So 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, I think, 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.
ZIPPERER: You covered this in the book, when there was all the controversy over Ed Lee and the Twitter tax and he was getting savaged by some. I remember thinking [that] Ed Lee was just doing what any mayor would’ve done, which is grab for the golden ring, which at that time was tech companies, and try to get them into the city. It’s maybe a similar analogy in the political realm of this thing seemed to be happening and people went with it because A, there wasn’t anything else going on and B, it was going in a good direction for at least a lot of folks there.
WEBER: Regarding Ed Lee and the Twitter tax break, I think that’s right. The perception in the moment was that the city was still recovering from the great financial crisis and the traditional engines of the city’s economy were not what they once were. The prospect of fast-growing tech companies was very appealing to the city and, as you note, as it I think would be for any city. Partly the resentment about the Twitter tax break came about because … around the time that the tax break was kind of developed in 2010, what nobody quite realized at that moment was that there was going to be a gigantic boom. So just a couple of years later when that boom was in full steam and then there was a lot of displacement and prices going through the roof and all that, people were like, “Wait, why did we do that tax break?” So I think that kind of colors a little bit the perception of it in hindsight.
ZIPPERER: The city was recovering from the AIDS crisis and the real estate downturn around the turn of the ’80s and ’90s; 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, with either better regulation or different handling of the tax situation or housing or any of that kind of stuff?
WEBER: 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, I think, 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 really 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. And that is part of what produced problems that we had through the boom period and have again in spades now with the AI boom.
ZIPPERER: Over the past 35 years since you arrived in the city, which mayors do you think were maybe most successful at dealing with whatever transitions came along during their time in office?
WEBER: Willie Brown was probably the most effective in terms of making his priorities happen. He had a somewhat traditional set of mayoral priorities: big infrastructure projects — so, the new baseball stadium and Mission Bay and rebuilding City Hall. Willie was effective in getting those things done. He didn’t really go after the homelessness problem in a very direct way. So he didn’t try to do everything; but the things that he tried to do, he pretty much got done. Now, people argue with his methods and that’s a different discussion, but he did make things happen.
ZIPPERER: Near the end of the book, you have a great couple sentences about the current mayor, Daniel Lurie. You write, “By refusing big donations and funding his own campaign, Lurie wouldn’t owe anyone anything, as he liked to stress on the stump. That approach also meant that nobody would owe him anything. City Hall could be a cold place if no one was interested in doing you a favor.” Lurie so far has had a pretty popular run in office. Do you think he’s created enough allies in City Hall to be effective long-term or who will stick by him when things inevitably get rough?
WEBER: That’s a good question. He’s still a relatively new mayor. I think that to the extent that he retains the kind of public support that he has, that that is going to create allies for him and help solidify the alliances he has. In politics as in other things, winning is a great balm for things, and if he’s a very popular mayor, people want to attach themselves to that. I think that so far he’s done quite a good job. I don’t have much of a view into the inner workings of his administration, which didn’t really kind of come into place until after the period that the book covers. But I certainly think that his public strategy of being very present everywhere, showing up everywhere and his kind of natural manner, this sort of earnest but sort of nice guy persona and just being present and approachable and a cheerleader for the city and good on social media, I think all those things have been very effective and it kind of underscores an important psychological component of civic governance.
The city has a lot of employees, and if people kind of believe in the leadership and are enthusiastic about where things are headed, they’re going to do a better job. Certainly in the case of public safety and street safety and street conditions, which obviously has been one of the biggest issues for years, things have definitely improved under Lurie. …
Incidentally, I think that success has a lot of interesting similarities to Mandami’s success in New York so far, which is also because he’s the kind of cheerleader and [the] personality aspect that has been very significant.
ZIPPERER: 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, whether it’s developing a new park or just coming together to solve problems and do long-range planning. She was saying San Francisco does not have that. What had been there—which was the famous wealthy families who if a mayor did want something done, they would call [them] into the office and say, “Hey, we need X, Y, Z done”—that seems to be changing. What do you make of this kind of new generation of moguls? You had some really insightful stuff in your book about how they’re not wedded to the city the way that previous moguls were.
WEBER: I think 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, going back to the ’70s. Rudy talked about how back in the day, meaning 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. So there was really a much tighter relationship between these old-line industries and the city.
Warren Hellman — whom 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. Warren himself played an important role. 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, even gradually moving away, Schwab, Chevron, either moving to the suburbs or moving to Texas. So the kind of old-line big corporate headquarters that kind of anchored that old way of doing things was less of a force.
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. I’m really talking about internet companies. So these companies can be located anywhere. For Twitter, I mean, half the management of the company wanted to move south anyway. They never had a huge commitment to the city. Ev Williams and Jack Dorsey, they were very interested in the transformation of Mid-Market and being a good corporate citizen. Ev in particular was very committed to that, and that’s part of why they did that.
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. So I think the companies by nature have looser ties, because they’re not tied to a physical industry that’s located here, like the railroads or the shipping companies or something. Then the executives have looser ties because they’re kind of stateless people in this funny way.
ZIPPERER: Was it British Prime Minister [Theresa] May who referred to “citizens of nowhere”?
WEBER: Yeah, that’s right.
ZIPPERER: Go back a hundred years [or so], you had the rich and powerful who would see owning a newspaper or radio station and all that kind of stuff as a worthy investment for their own influence and even extending their business reach. Tell me if you disagree with me, but it seems that this new generation just doesn’t have the patience for that or an understanding of what kind of investment is needed for The Washington Post, for The Bay Area Citizen, or Time magazine—[Benioff] bought that and then got rid of it. They don’t understand the investment and patience needed for something like that to thrive over decades.
WEBER: There was always a bit of a debate about how profitable Hearst Corporation was under William Randolph Hearst and to what extent he subsidized it with the mining money But certainly there are many, many examples. I worked at the L.A. Times, and the L.A. Times was a business empire in its own right. It was gigantically profitable, and it also put the Chandler family into a position to make money on other things too, but they were really profitable. A lot of these old family media companies made a lot of money for a while. Then the internet destroyed the business model of newspapers.
I’ve had a lot of experience with this, and tech people tend to believe that the problems with the news business are the fault of the people running those businesses because they’re just kind of clueless and don’t get it. So the thing that these media companies need is just a little bit of good Silicon Valley thinking that will kind of straighten everything out.
It’s a very arrogant attitude, and it’s an incorrect analysis of what’s going on. The people running these companies were not idiots, and these are complex and difficult businesses and they require a lot of knowledge and sophistication and creativity to run profitably. It’s just not an easy thing at all. There’s no formula. So I think a lot of the … sort of tech moguls’ adventures in media have suffered from that kind of fundamental misunderstanding really of what they’re getting involved in.
The thing with Bezos and the Post is very sad, because Jeff Bezos made a solemn promise to Don Graham to be a good steward of The Washington Post, and he broke that promise when it was convenient for him because he needed to cozy up to Trump in order to get Blue Origin into the race with SpaceX. And this recent reporting that came out in this new book [Regime Change] confirms that that was the reason that Bezos threw the Post under the bus.
ZIPPERER: In the early sections of your book, you’re relating how psychedelic drugs played a recurring 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—or not—that permissive attitude toward hard drugs played in creating or not stopping the current situation?
WEBER: 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.
ZIPPERER: Another [attraction of] San Francisco is just the general openness to difference and even weirdness, which was leading me to wonder if this could have happened in other cities. Nowadays, Austin, Texas 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 vaunted matchup of creativity and tech booms?
WEBER: Well, I don’t know. I guess the short answer would probably be no, based on just 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 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 were 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 moment of the doom loop.
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.
This interview appeared in shorter form on The Voice of San Francisco.