Save San Francisco’s Soul: Jonathan Weber on Technology and Politics in the City By the Bay

00:00:30 Andrew Keen: Hello, my name is Andrew Keen. Welcome to Keen on America, the daily interview show about the United States. Hello everybody, as always. I'm broadcasting from San Francisco. In fact, up the road from Mount Olympus, which is the geographical heart of San Francisco, and yet San Francisco has always been a city on the edge, that is at least the title of a new book, a very, very interesting and important new book about the technology and politics of San Francisco, indeed the soul of San Francisco, by my guest Jonathan Weber, who knows the city inside out. Jonathan, congratulations on the new book, City on the Edge.

00:01:38 Jonathan Weber: Thank you very much, Andrew. Pleasure to be here.

00:01:40 Andrew Keen: This shall we say that the fetish of the edge, Jonathan, you're a veteran tech guy, has always been something that's obsessed the tech community. I assume that the title of the book, City on the Edge, refers to this obsession the tech community have with the idea or the promise of the

00:02:02 Jonathan Weber: edge. Yeah, that's certainly fair. It has several meanings, I think, in the title, so certainly cutting edge tech on the cutting edge, and the obsession with that, that you refer to, that's certainly part of it. San Francisco is physically on the edge of the continent, which is a part of what's shaped its, its identity. You could say that the city and tech is sort of on the edge of the future, in a sense, so that's also part of the meaning, so yeah, so it works in several different ways.

00:02:36 Andrew Keen: The full subtitle of the book, City on the Edge, is Technology Politics and the Fight for the Soul of San Francisco. As an old-time San Francisco resident, Jonathan, I'm not sure that San Francisco ever had a soul, did it

00:02:51 Jonathan Weber: well, I think. I think it did, and does. I mean, it's San Francisco, is a very unique city, very iconic city. It kind of has a meaning bigger than itself, represents kind of a place where you can go and be different and do something different, and people aren't going to judge you, and you have a different kind of freedom, and the, you know, the country tilted in the nuts rolled to the west, right. So, so San Francisco, as an idea of a city, encompasses all those things, and I think a lot of people come here with an idea of San Francisco as a special place,

00:03:29 Andrew Keen: and yet maybe the mythology of San Francisco is that it always used to have a soul and now it doesn't. One of my favorite scenes from certainly my favorite movie about San Francisco, Vertigo, is in the San Francisco shipyards when Jimmy Stewart's about to be set up by the villain in the movie, and this villain points to an old photo or an old, an old painting of San Francisco, and said, well, that's the old San Francisco, the new San Francisco isn't what it used to be, is, is that a feature? I mean, your new history of San Francisco really begins in the 90s with the internet boom, but is San Francisco a place almost in a structural sense of nostalgia, of always looking back and thinking, well, in the old days things were better,

00:04:19 Jonathan Weber: you know? I certainly think there's there's a bit of that. I don't know if that's uniquely San Francisco thing. I mean, you know, we currently have a presidency which is built on the idea that things were better in the 50s or something, so, so I think there's a kind of a natural human instinct around nostalgia sometimes and loss of great things in the past, so certainly, you know, in the city is a place where people come with a certain idea of what it is, and that idea, you know, can be pretty fixed over time, and so then eventually, of course, it's it's going to be not that place, because it changes. So I think that perhaps that nostalgia is a little stronger here, almost because of the high hopes and expectations that people have when they, when they come here.

00:05:11 Andrew Keen: You begin your book in the 90s. This tech history of San Francisco, back in 1992 you say in the book only 2% of people in San Francisco worked in tech. By 2019 it gone up to 35% an astonishing rise. What was San Francisco like? Before tech,

00:05:33 Jonathan Weber: well, if you go back, so before tech, say in the early 90s, late 80s, I mean, the city was economically troubled. It was unclear what was really going to drive the economy in the future. It was very dependent on banking and financial services, some of these downtown companies, but a lot of those companies were starting to move to the suburbs, and the old manufacturing base that used to exist in the city had kind of deteriorated over a long period of time, as it did in most of America in the post-war period. So the city had lost most of its manufacturing, the corporate headquarters was kind of a little tenuous, and so that, and then in 1989 there was the Loma Prieta earthquake, which did an enormous amount of damage, and so that was an economic setback as well. So it was really unclear what the future of the city really was from an economic standpoint, certainly. Now, at the same time, culturally, it was, it was very rich. There was a lot, a lot going on, different tendrils of the of the counterculture from the 60s kind of reformulated into different things, including this group called the Cacophony Society that I, that I write about, and which really founded the Burning Man festival, and so there was a tremendous amount of cultural ferment in the city, even though the economy was pretty weak, and in some ways those are related, because if you were an artist, you could move into a warehouse in Soma that was condemned was going to be torn down, but in the meantime you could rent it for 50 cents a square foot, and so that was kind of a boost for the artistic community.

00:07:20 Andrew Keen: There's always a bit of a crazy place. You begin the book with a quote from Joan Didion, of course, who wrote one of the great critiques of the counterculture down the hill on Haight Street, where she spent some time. It was always a bit of a mad place rather than a culture place, wasn't it?

00:07:35 Jonathan Weber: Well, I guess culture can mean a lot of different things, but yeah, certainly there was a renegade aspect to the city, I guess. You know, a lot of, yeah, a lot of crazy people, and you know, in the 70s, crazy in a very bad way. I mean, the summer of Love was followed by the 70s. David Talbot's book, Season of the Witch, illuminates this extremely well, but it was a crazy time, very violent. There was the Patty Hearst kidnapping and the zebra killers, and all kinds of crazy stuff. And the city has always had a bit of a dangerous edge to it, in some way, a little bit anarchic, I think. People think of it as like a left-wing socialist place, but, but there is a kind of an anarchic aspect to the to the city's core that I think has always, always been a part of it, and you know, culture. I'll just say two things about, about whether San Francisco is a cultured place, and I think on the one hand, in terms of traditional high culture, the city has always aspired - city fathers, over the long period of time, have aspired to the city being a great city, like New York, or the great cities of Europe, or something, so they always invested in high culture, so specifically the opera, the symphony, the museums are actually quite good for even spectacular for a city of its relatively small size. So there was that, and then at the same time the culture that I'm really referring to more specifically, here is much more the kind of underground artistic culture that kind of originated in different ways around the counterculture in the 60s, and then kind of developed and evolved from that, and so that was a kind of a street culture, you can call

00:09:28 Andrew Keen: it, I mean, the culture, I guess, of the beats of bookstores, there was a pre 60s culture, right.

00:09:39 Jonathan Weber: Well, the beats, yeah, the beats begat, they began in San Francisco, that's right, yeah. So the beats, the beats were here in the 50s, came here in the 50s, that was kind of Ferlinghetti, Jack Kerouac and Neal

00:09:53 Andrew Keen: Cassady, Neal

00:09:54 Jonathan Weber: Cassady, and so that was kind of the beginning of the cultural flowering, and in fact, you know, there were some direct links, so the Whole Earth Catalog founder

00:10:09 Andrew Keen: Stewart Brand,

00:10:10 Jonathan Weber: I'm sorry, Stewart Brand, so Stewart Brand came from North Beach. He was fascinated with the beats and the culture in North Beach. He was very.. he came there in the early 60s and was kind of involved in that, and then got involved in the psychedelic movement, which kind of grew out and partly grew out of that same North Beach culture

00:10:29 Andrew Keen: and. Now he has his long, long now foundation with an excellent bar down on the bay. What makes a city great? Then, Jonathan, I know you addressed this. Can or could San Francisco ever be great in the sense that it's for better or worse physically such a small place,

00:10:52 Jonathan Weber: right? Right. Yeah. Well, it is. Yeah, it's a very small city, and so in that respect, it's never - it could never really match New York or London or Tokyo, you know. These places are, or even LA or Chicago, LA, right? So these places are far larger, but at the same time, even though San Francisco had 800,000 people, 10th the size of New York, but it's also the headquarters of a larger region, so it, you know, really kind of functions that way. So the city is a little bit bigger in a practical sense than the actual population number, but that said, you know, I do think that the size of it, and also the geographical limitations of it, because it can't really grow, you know, there's nowhere to go, really, so you know, I think that is a probably a limiting factor in the city's sort of throw weight, ultimately,

00:11:48 Andrew Keen: I guess it could grow up literally physically become Hong Kong, although given the earthquakes around here, that's probably not very viable. Of course, it's a remarkably cinematic place. I mentioned Vertigo, there's Bullet, and many classics made here. What's your favorite movie about San Francisco?

00:12:06 Jonathan Weber: I think I would have to say The Maltese Falcon, and that was partly because I lived in one of the buildings, but the

00:12:17 Andrew Keen: physical panorama of the city is breathtaking, isn't it?

00:12:23 Jonathan Weber: Oh, yeah, I mean it's incredible, and just the raw physical beauty of the place is just mesmerizing, and that is, of course, one of the reasons that it is what it is, one of the things that draws people here, and keeps people here, and it also, you know, is one of the things that makes the kind of management and development of the city much more complicated, because it's so beautiful, like you don't want to mess that up, right? So, so the fights around development, so if you, if you build high rises along the waterfront, that's going to really make the city kind of less beautiful in a way, so or make the beauty of it less accessible, and so that, so there's a real desire not to, not to ruin that, but that's not so easy.

00:13:14 Andrew Keen: The city, of course, was born in the gold rush. At one point, I think it was one of the largest places in the world. It's had its literally and figuratively its ups and downs, its earthquakes, its booms and busts, its railways. You go into the downtown park, you go to the Stanford Hotel, and all sorts of remarkable characters from American 19th and early 20th century life, Hearsts, and the names are endless. Is that just built into the very DNA Jonathan of San Francisco, that it's a city of booms and busts, that it was built as a gold rush city, and it's never really changed.

00:13:55 Jonathan Weber: Yes, is the short answer. I mean, it's very much a boom and bust town. There was the gold rush, then there was the silver bonanza shortly thereafter, which was actually even more significant. More recently, you had in World War Two, you had a huge boom. It was the headquarters of the Pacific Fleet. It was one of the main armories, the shipyards, and all kinds of stuff. And so there was a huge boom, and then the war ended, and there was a big bust. So, so these things are, yeah, very much part of San Francisco, and you can hardly have a conversation about any current up or down without people mentioning, well, the city's always been a boom and bust town, and it's kind of a cliche, but it's very true, and here we are, here we are again in them, in a kind of AI boom, which is most people think is not really going to last in its current form for very long, and, and so the city will be kind of juggling that, that tension again,

00:14:57 Andrew Keen: and like always, people, commentators like you and I describe it as the biggest boom in history, which, of course, it is, until the next big one. So, why was, or why is the tech boom the.com boom? You came here in the 90s, I did. I was an entrepreneur, you were a journalist, you started Industry Standard. Is it any different from what happened before? Does it have particular characteristics that we need to understand it to make sense of the promise and problems of San Francisco in. 2026

00:15:32 Jonathan Weber: Well, I think that the.com the tensions that first arose in the, in the late 90s, around the.com boom, a lot of it had to do with, with the rent, basically just rent went way up, that made life very difficult for a lot of people, for not just for individuals or families, but also for businesses, you know. Commercial rents went way up, so, so I think that, that the lesson there, right, is that when these booms happen, that's going to create a lot of pressure on certain parts of the population and certain parts of the business community, and like, how do you, how do you mitigate that? And I don't really know that the city has come up with many very good answers to that question of how to kind of mitigate some of the dislocations that come when you have just a huge influx of money in a very short period of time, and one of the things that's different now is that the these kind of booms and busts, you know, they build on each other. So the.com boom happened, and then there was a bust, but even though there was a bust, there was still a lot of money that people made in the boom that was sitting there, and that was invested in the next round, and so now with AI, we're in kind of the third cycle, you know, since the 90s, and so those fortunes have kind of accumulated and sort of stacked up, so that so the kind of level of wealth that's involved now is even far, far greater than it was in late 90s, and so that makes some of the, some of the tensions, you know, even more difficult to deal with. The

00:17:19 Andrew Keen: cliche, Jonathan, is that ordinary people, and I mean that in a literal sense, not a pejorative sense, can't live in the city, the firemen, the teachers, the policemen, people who work in stores, is that true?

00:17:33 Jonathan Weber: Well, there's a couple of things to think about. So, the city has pretty strong rent control laws, so people who have been in their same rental apartment for a while are paying pretty reasonable rent. So, there's a, there's a class of longtime residents who are not necessarily making a ton of money, and who can afford to live here just fine due to rent control, so, so there's kind of that sort of exception. And then it really depends on what you mean by can't afford to live in the city, you know, so if you're willing to live with roommates and have essentially much less space than you would somewhere else. Then all things are possible. I mean, it's always been the case, for example, when, if young, creative people want to go naked in New York, you know, they move to New York, and it's very hard to afford living in New York, but they figure it out anyway. And so I think the same applies here. If you're, if you're dead set on being in San Francisco, you can find a way to make it work. It's probably not going to be very comfortable. You can also live in the East Bay, or one of the outlying areas, which increasingly people do. So, so it's possible, but it's difficult, and, and it means that there's a lot fewer younger people around, you know. So, one of the concerns that the city economist has is that in the pandemic, the city lost a lot of the service workers, service people who work in the restaurants and clean the buildings, and so forth, and those people left in the pandemic because their jobs disappeared, and they, and they haven't come back, so that population is kind of gone, and that's an issue, because that population not only provided the workforce for a lot of the culture economy, but was also kind of the participants, right, the cliche about the actor who's waiting tables, right. Well, that's a real thing. So if that person can't live in the city anymore, doesn't live in the city anymore, they're both not working here and also not doing their art here.

00:19:46 Andrew Keen: And where every boom is associated with wave after wave of young people coming here, gold miners, digital gold miners, entrepreneurs. You came here in the 90s. What's your story? What's your relationship with San Francisco?

00:20:03 Jonathan Weber: Well, I came here in 1990 to cover the technology business, specifically Silicon Valley, it was kind of funny, because when I arrived, my colleagues at the LA Times said, well, that's great that you're here and all, but if you're the Silicon Valley correspondent, what are you doing in San Francisco? Like, we don't really do that tech thing here, but anyway, so that's that's that's how I came here, and I. Will say, I just, the city was, I just loved the city from the very start, and I loved the outdoors, and I loved water sports, different kinds of stuff like that. So, personally, it was just a great place for me in that way. And then, over time, I really began, came to kind of appreciate the very, you know, just a very novel kind of freewheeling culture, you know, a lot of very interesting different kinds of people here, and, and a very different set of expectations, or lack of expectations, you know, back east there was always, you know, certain cultural norms and expectations, everybody, if you worked in Manhattan in the media industry, and then in the summer you have your house in the Hamptons, and you do your Hamptons thing, and it was all more kind of organized, and a little bit set in its system, you know. While I felt like San Francisco was much more a place where you could, you can make it up on your own, and dress codes. I mean, this is a silly thing, but I'm hearing jeans and shirt. I mean, you took your jacket off. I did take my jacket off, you know, because I still often tend to be overdressed, you know. I forget that, you know, like, yeah, nobody cares. San Francisco people make fun of the city for its bad fashion, which is fair, but there's something nice about not having to worry about wearing a tie and wearing a jacket all the time, you know, the basic style of business is much more casual, and so there are a lot of subtle differences like that I really appreciate about San Francisco,

00:22:13 Andrew Keen: thinking of the San Francisco in the 90s, and the San Francisco of today. Jonathan, you mentioned clothes and clothes stores. One reason why people perhaps don't dress very well in San Francisco is because all the stores have been driven out, and the downtown, or what's left of the downtown, increasingly looks like a battleground, massive homeless city. Is really the story of San Francisco one of homelessness and real estate and retailers being forced out and people not being able to afford to live here? Is it for all the.. and it's perhaps rather ironic, given that San Francisco is supposed to be on the on the edge of digitalizing the world of the digital revolution, that the real history of San Francisco, the core history is a physical one that's bound up with real estate, the price of real estate, the availability of real estate, homes, retail.

00:23:09 Jonathan Weber: Yeah, well, I mean, you can tell the story of San Francisco and of California, really. That's just a story of real estate, and, and that's certainly a certainly a major factor. One of the people I spoke to for the book by name, Chris Daly, who was a supervisor for a while, very left-wing guy, and his formulation, he said, you know, all politics in San Francisco is ultimately about land use, and it's, and it's a zero sum game, so there, that's why we have all these fights, and I think that there is, there is some truth to that, there's not, not that much land, and, and, and you, you know, you can, you can have a high-rise apartment building, or you can have a park, or you can have a retail store, but you know you can't have all those things, so.. so I think there's some.. there's some truth to that, but the reason that these problems have intensified is because of the huge influx of wealth from tech, and so that's just kind of intensified all of the conflicts that would go around these essentially competition for land and real estate. I'm

00:24:20 Andrew Keen: not sure, Jonathan, everyone would agree. There's a rather conservative book called San Francisco, San Francisco, written by an East Bay writer. I'm sure you're all too familiar with that, argues that the failure of the city, or what they see as the failure of the city, massive homelessness, inequality, crime, all the rest of it, has been caused by mismanagement rather than the tech industry. Tech people probably haven't helped, but the real problem is with progressive politicians, the Pelosi is, and the nuisance of the world. Is there any truth to that? What do you decide in your history?

00:25:00 Jonathan Weber: Yeah, well, I think I generally take a plenty of blame to go around position on the on the problems of the city, especially in the pandemic era, and I think it is certainly true that progressive policies contributed to some of the problems, especially the fentanyl crisis of recent years, and I think the fairly permissive attitude towards. Sleeping on the streets and things like that has probably led to somewhat more homelessness than you would have had otherwise, and I think that there are a number of places where you can point to policies and say, you know, like shoplifting or things like that, you know, where the policies and the laws got sort of too permissive, people got a green light for very bad behavior, took advantage of that, and that created a big mess. So, so that is certainly part of the dynamic, but at the same time, you know, homelessness in San Francisco goes back a long time, predates of the people you're talking about, and there's a lot of structural causes to it, both in the country and specifically in California, and you know, and all the reasons that San Francisco is a lovely place for someone like me are also reasons that it's a lovely place if you're homeless, so people come here for that, and it's a city that has always welcomed the misfits and the unfortunate, and things like that. So, there's been a real reluctance to take very harsh measures that you would need to really drive people out of town, you know, that's really what the, what the right wing, you know, would like to do, you know, is essentially to drive all these people out of town, and you know that's possible, and you can make an argument for that, but there's never been much appetite for that politically.

00:27:02 Andrew Keen: Of course, Marc Benioff, recently the CEO of Salesforce, seemed to suggest that and got himself into trouble. I've lost count, Jonathan, and the amount of times people from outside San Francisco, when I travel, or when I have friends from outside town come in [unclear]. They all ask me the same question: Is it as bad as it seems? Is it really a place of massive homelessness? And my response, maybe as a proud San Franciscan is known that there are parts of the city where things aren't very attractive, parts of downtown, but mostly where we are now, and out towards the ocean, things are no different from any other city. What, what, what take on San Francisco do you think it's fair? Is it that is it the end of the world or is it just another place with lots of urban problems?

00:27:58 Jonathan Weber: Well, yeah, I think very much the latter. You know, I'm San Francisco has been kind of weaponized by the right wing as a, as a kind of exemplar of urban dysfunction that results from democratic governance and so that there's been a really a somewhat deliberate campaign in the right wing media over several years, you know, to really highlight the worst of the worst in San Francisco. Yeah, it's no secret right around tabloid journalism, and you know these are kind of sensational things that are that are easy to make media out of, and so people have done that over the course of several years, and that's had a big impact on the on the city's reputation and image. So, so people think that the whole city looks like, you know, those clips they see on Fox News, when in fact you know that's only a few blocks of downtown, you know, but people don't make those distinctions, so, so I do think that the problems have been caricatured and sort of deliberately kind of emphasized for political reasons, and so, so there's there's that, and I do think that the problems are kind of basically similar problems that most cities have at the moment, and just maybe a little bit worse than, for various reasons, you know, they're a little bit more intense here, but they're of the same genre, I would say, as many other places, and you know, if you look hard enough, you know, you can find similar scenes to what people see here. You can find similar things in most other cities. Probably you have to look harder for them. The

00:29:46 Andrew Keen: city also punches above its weight in terms of its politics and politicians, Kamala Harris, of course, lost the last election to Trump. Lot of talk of Newsom, or even Harris running again in 28 Everybody's heard of Nancy Pelosi. Why there's so many prominent California San Francisco politicians within the Democratic Party, of course, very few in the Republicans. What is it about San Francisco that generates these this national hall of fame when it comes to politics and politicians? Well, the politics is very competitive in San Francisco.

00:30:30 Jonathan Weber: So it's very professionalized in a way, and, and the, and the stakes are very high, and that's because of a kind of historic structural thing. So, so San Francisco has always been the kind of dominant political entity in California, even though Los Angeles is a much bigger city, but traditionally San Francisco used to be bigger, and then just over the years the kind of corporate headquarters, the banks and stuff were here, financial services, lot of law firms, so the city kind of had a leadership role in the state of California, and so, if you're the mayor of San Francisco, you can see a direct line to being governor of California, and then, if you're governor of California, because it's the largest state, there's a direct line to being President of the United States, so therefore, as a young ambitious politician in San Francisco, you can actually see a direct path from your local election to the White House, and so I believe that is one of the things that has made it highly competitive as a political environment. Secondly, because it's such an attractive city and high-profile city, and attracts many different kinds of people, so if you're like, for example, a person I interview in the book, David Campos, who was a supervisor for a while, and he came here specifically because it was a place where you could kind of, there was a lot of political ferment, there was a lot of ideas flowing around, if you were like a left-wing person, you could kind of get stuff done in San Francisco, so, so it was a little bit of a magnet for people in that regard, just because it's high profile, and then because the kind of rewards of success are so great, it became hyper competitive, and so I think that is part of a big part of why it punches above its weight, so then as a consequence of those things in the very powerful political machine was built by the Burton brothers, John and Phil Burton, and then Willie Brown was an integral part of that machine, who

00:32:41 Andrew Keen: was, of course, Kamala's mentor, literally and figuratively,

00:32:45 Jonathan Weber: correct. So, Willie was Kamala's mentor, and Willie, Willie was also Gavin Newsom's mentor, I mean, get, you know, Willie was the mayor from 95 to 2003 and then he, he picked all the subsequent mayors, so he picked Gavin, and then, and then he picked Ed Lee after that, and he picked London Breed after that, so he's really wielded enormous influence, and that, and Willie is one of the greatest politicians this country has ever produced. So, a level of brilliance on just how to do politics, you know, how to get, how to pick the right candidates, how to win elections, how to build coalitions, how to develop policies that will be popular, you know, these are things that you know Willie is really mastered, and then his proteges, you know, have to have mastered it too, and they're very, very talented bunch.

00:33:40 Andrew Keen: I wish actually Kamala Harris had inherited some of Willie's political skills. I'm not sure he always passes them up.

00:33:47 Jonathan Weber: Well, you know, she did get to be vice president, so you know you don't get to be Vice President without at least some political skills, and in fact I would, I think she learned some of Willie's lessons too well. Part of the dynamic of the Brown-Burton machine is that very focused on kind of the mechanics of winning elections, and, and that isn't always the best way to present, and I think that Kamala kind of suffered from that, like she was she was a tactician, and she, she could never really convince people that she had, like, ideas of her own, and something that she stood for, you know, because she was just kind of good at the nuts and bolts of things,

00:34:34 Andrew Keen: so is Pelosi in the Willie Brown school a parallel genius politician?

00:34:42 Jonathan Weber: I would say so. I mean, I've personally never been quite as impressed with Nancy Pelosi as some other people have, but, but certainly you know she also came out of the same machine, I mean she holds the seat of Phil Burton, who died young, his wife took the seat, and then Nancy was picked for the seat after them, so she is the product of the same machine has worked very closely with Lily [as spoken — likely "Willie," i.e. Willie Brown] over the years, and you know, and I think that her, that the weaknesses of that heritage, let's say, have really come to the fore here at the at the end of her career, where her machinations around who would succeed. Her have just been ridiculous. I think the

00:35:33 Andrew Keen: current mayor, Daniel Lurie, who is a scion of the Levi family, has been getting some good press. How do you position him in terms of your history? I know you discuss him.

00:35:45 Jonathan Weber: Yeah, well, so Lurie does represent a very important break from the past, and that he is not a product of the Burton Brown machine, so for the first time in 35 years, there's a, there's a mayor who's not part of that political system, because he's independently wealthy, he doesn't have the same kind of obligations to other people that politicians often have, so he's able to be a little bit of a free, you know, he doesn't owe anyone anything, which is a good thing in a lot of ways, but it can also be a difficult thing, because it means that nobody owes you anything, and of course governing a city requires a lot of coalition building and a lot of working of alliances and things like that, so I think that Lurie, so far, has done quite a good job. He was elected as a change candidate, people were fed up with the system because of the conditions in the streets and other things, and there was a lot of low hanging fruit, I think, around some of that, you know, the police had almost stopped working because they were so fed up with the with the DA not putting people in jail, and you know, not agreeing, you know, it was very irresponsible, but it was true that there was a bit of a kind of a stand down by the by the police, and you know, in a real kind of demoralization, you know, throughout the city government, I think, and so Laurie was able to kind of turn that around, and you know, he's he kind of shows up everywhere, he's like very earnest and very consistent in his manner, and he's sort of friendly and accessible, and you see him everywhere, and so people, you know, people kind of appreciate that, and then he's just been very lucky in that his tenure has coincided with the huge influx of AI money, so that's taken a lot of the pressure off. So I think he's done a good job so far, but the bigger tests are still to come, as I wrote in a piece this week.

00:37:49 Andrew Keen: Yeah, I bumped into him recently at a wedding. He didn't strike me as a particularly charismatic character. He's no mandami, is he?

00:37:59 Jonathan Weber: No, no, he's certainly not. He's not a very charismatic guy. He's not like super impressive when you meet him, really. But again, he's just very, he's very kind of consistent, he's very steady, he's very friendly, he's smart enough, he's not compromised, you know. So, you know, in a way that I think there's a feeling that's what the city needs now, a little bit. We don't need another charismatic superstar, we just need somebody who will kind of make sure that public works, you know, cleans

00:38:30 Andrew Keen: up that intersection cleans up the streets, literally. Sometimes you're a tech guy, Jonathan, so you talk to a lot of very influential tech people: Ron Conway, Brewster Kahle, who's been on the show recently, John Battelle, Matt Mullenweg, Craig Newmark, many enormously influential figures, both in San Francisco and in and in the tech community with a very wealthy people, great deal of economic resources. What did you discover in your history of the relationship between the tech community and the city itself?

00:39:09 Jonathan Weber: Well, at the beginning of the book, in the 90s, when the commercial internet and the web are first rising, and that's sort of creating the tech industry in San Francisco, and during that period, that the city, the government, and that, and the industry had very little to do with each other, the industry was small, the city didn't care. It wasn't important. There wasn't a lot of money, and didn't understand it, you know. Willie himself told me, you know, I didn't, I didn't understand any of that tech stuff, you know. Now he's a little disingenuous on his part, but yeah, Willie understands

00:39:47 Andrew Keen: everything he

00:39:48 Jonathan Weber: does, but that conveyed, you know, a little bit the psychology of the moment, you know, this tech, that tech stuff, whatever, you know, and then the industry, for its part, they didn't need anything from the city, so they just wanted to be left alone, and so that was fine. And the beginning of the book is really more about the tech, the first few chapters, you know, about the rise of tech, then it becomes, as the industry gets bigger, it starts to kind of run into politics a little more, and then in particular in the late thoughts where you have the advent of specifically of companies in ride hailing and then Airbnb in the lodging business, and then suddenly the tech industry is in. In the city's business, right, the city, you know, the city is responsible for regulating taxi cabs and for deciding the rules on rental apartments and hotels and stuff. So, so now the tech industry is in the city's business, so that creates a very, very different kind of dynamic, and so on top of that, you had this huge influx of money, which is creating a lot of development pressure, and then that, you know, is a whole other set of issues, so, so, for those two reasons, the, you know, gradually the kind of the tech industry and the government, from being pretty separate, you know, found themselves really in a lot of conflict over these, over these couple of, couple of issues, and I think, well, we can, we can talk more about the specifics of that.

00:41:19 Andrew Keen: I know you talked to Chris Lehane, one of the most powerful figures, both in tech and in San Francisco, for the book. Chris is currently Sam Altman's consiglieri, probably wouldn't use that word, but I can at OpenAI, and he previously was with very influential figure within the Democratic Party. Previously also with Airbnb, you mentioned Uber, based in the city, of course, founded by another controversial character, Travis Kalanick, who's from Los Angeles [as spoken], rode in to San Francisco. Are you suggesting, Jonathan, that maybe in the beginning a lot of the digital innovation was in Palo Alto, Google, Facebook, but the beginning of the century it shifted to San Francisco, not that it not only shifted to San Francisco to companies like Uber and Airbnb, which set up in the city, but their business was an urban business, a more physical business,

00:42:18 Jonathan Weber: right. That's right. So, yeah, they were, you know, the internet, to the extent that it's about websites, is sort of detached from physical place, but then when you're talking about ride-hailing and Airbnb, it's absolutely not, and in fact, both of those companies started out doing things that were kind of plainly illegal, actually under local law, to put it

00:42:45 Andrew Keen: politely. Jonathan, yeah, well, that's not different from YouTube, that began illegally as well, many of these internet companies began in a very shady part of the law.

00:42:55 Jonathan Weber: Well, that's right, you know, part of the ethic of them, you know, better to ask forgiveness than ask permission, right? Move fast and break things. Yeah, so all those cliches are kind of true, and you know, one of the funny things about the ride-hailing thing, which a lot of people don't realize is that when Uber first started, they were just about, they were using called black cars limousines, so it was a limousine dispatch thing, and it was expensive as black cars are, but it wasn't really competing in the taxi business per se, and then Lyft came along, and then Lyft started doing this thing with the pink mustaches and the fist bumps, and you know, pretending because it was illegal, like you can't pick up passengers and charge a fare in a private car like that, you know, that is illegal, has always been, but Lyft came up with the fist bump and the pink mustache to sort of pretend somehow that this was not a taxi, that it was a shared ride or something, but that was all a fake, you know.

00:44:00 Andrew Keen: But then Uber assumed, so Kalanick assumed that this was going to be shut down, like you can't do that, you know. But then when it wasn't shut down, then he thought, "Oh, if it's not going to be shut down, we better start doing that too. And then the rest was history, you know. And, in fact, you know that it fell between some regulatory cracks, which is what.. and then they got enough critical mass that it was too difficult for the city or the state to really stop them. I mentioned Chris Lehane earlier, the classic political fixer. I think he ran Al Gore's campaign, very influential democratic operative who now works in tech. Have you seen this convergence, then, of guys? I mean, there's only one Chris Lehane, but guys like Lahain, or people emulating Lahain, trying to merge the physical and the digital world, where all the big tech companies now needing to hire a lahane, someone able to bridge the divide between their abstract business and the physical reality of being in San Francisco.

00:45:06 Jonathan Weber: Yes, I think is the short answer, and there's there's precedent for it with several other companies, you know, Amazon hired Jay Carney, powerful political operative there, Amazon, Amazon, obviously very much in the delivery logistics business, so that's oh, that's yeah, rather than San Francisco, Seattle rather than San Francisco, but yeah, and Uber. Had hired various Obama administration people, including and the guy

00:45:35 Andrew Keen: who runs Uber Eats now, is Kamala Harris's brother [ed.: brother-in-law — Tony West is married to Maya Harris], and right,

00:45:39 Jonathan Weber: that's right, Tony West, Tony West, right, and they had hired David Plouffe, who was Obama's campaign manager, so yeah, so that, that is definitely been a thing, and Ron Conway, you mentioned earlier, so Ron Conway is a venture capital, very influential,

00:45:59 Andrew Keen: early stage venture capital, very successful, very powerful,

00:46:02 Jonathan Weber: right, angel investor, and, and you know, Ron was very early in recognizing that the industry was going to need to play in politics, because tech people generally wanted to ignore it, but he was like, "no, no, you know, this is really going to matter, and the city is going to matter, and like, we want these businesses to be in the city, because for, you know, various reasons, and, and so he really got inserted himself really into politics early, relatively early on, back in around 2010 and played a very big role in, in kind of encouraging the companies to be more politically savvy, and by hiring people like Chris Lehane, for example,

00:46:47 Andrew Keen: Jonathan, your politics and my politics, I think, are probably similar. We're no fans of MAGA or Trump, but it is no wonder, in a way, that San Francisco has this terrible reputation on the right, given the intimacy of business and politics. I'm not suggesting that the Lehans or the Newsoms or the Pelosis are corrupt, but it is slightly troubling, isn't it?

00:47:13 Jonathan Weber: In what,

00:47:14 Andrew Keen: in the way in which it's become a democratic fiefdom of one kind or

00:47:20 Jonathan Weber: another. Yes, I would agree with that. I mean, to the extent that it kind of distorts the terms of the political competition in a way that's not very helpful, so you know, you can't, you know, if you have everyone's a Democrat, but then you have the moderates who are kind of like Republicans, and then you have the progressives who are more left wing, like, why can't we just have Democrats and Republicans? It would be easier, right? And, and I do think that the dominance of the Democratic party has led to kind of some indiscipline, I would say, by the party, and you, that's a euphemism, that is a euphemism, you know, I think the, the way in which the party is able to kind of structure people's careers and dictate certain, you know, I'm not articulating this very well, but to give you an example, so Kamala Harris was a clearly talented person, she was an assistant district attorney with political ambitions, she dated Willie Brown, he introduced her to people, and then you know she was able to raise money, and people hated, you know, Kamala got elected partly on her merits, but mostly she got elected because she was the incumbent DA at the time was a guy named Terry Hallinan [Terence Hallinan], and who, who was a crazy left-wing lawyer, and like fist fighter, you know, he liked to punch people out when he disagreed with them, and so he was a super controversial figure that a lot of the people on the right just could not stand, and so Kamala, so it was like, okay, somebody's gonna take on Terry Hallinan, and then Kamala Harris happened to be the, or she was the person who kind of got it together to do it, and Willie's support was very helpful, but then, so she got elected, DA great, but then she served eight years as DA, relatively undistinguished tenure, she wasn't really able to solve the constant conflict between, you know, tough on crime or not. She was wishy-washy back and forth. Does she support the death penalty or not? This and that. She had a terrible scandal in the drug labs with the drug lab people doing the drugs, and but nonetheless she was then kind of deemed the choice to be state attorney general, so she ran for state AG with the support of the party, and she won with the support of the party, and then as state AG, she was immediately looking at the Senate seat, and then she got again with the support of the party got elected to the to the Senate, and so you know her political rise was really, you know, didn't seem to have a lot to do with her accomplishments as a politic, to put it again, and so that you know that's very problematic, like so she worked the machine well, she was she was a good candidate by the definitions. The machine, but, but she never really had to kind of come up with her own persona, or really persuade the voters, you know, that she was the one, and so I don't think that's a healthy system. It's not healthy for

00:50:45 Andrew Keen: the Democrats. I mean, no wonder she was such a poor presidential candidate,

00:50:50 Jonathan Weber: John, I think you know, if you look at the recent or the current gubernatorial election, you know, it also shows the weakness of that right, because you have a really very poor field of Democratic candidates.

00:51:02 Andrew Keen: Jonathan, one of the interesting things about this intimate, then uneasy relationship between tech and the city is the way in which, as the city got a worse and worse reputation, particularly for homelessness and one kind of vagrancy, and drugs, and all the rest of it, that the tech community tried to use its expertise in fixing things to fix the city. I know you write about this in the book, Ron Conway led it, and many of the other figures were involved as well. Is that a fair way to describe it? And what was the outcome?

00:51:39 Jonathan Weber: Well, I think that there are two different ways to think about the political involvement of the of the tech industry, and so there's one set of issues that have to do with the things that the tech industry needs for their business, so in the early 2000 and 10s, and you know, Chris Lehane working with Airbnb, and you know, Ron Conway and Citi, he established a group called SF City, and then there was all of the [unclear: "Mac Maenen"] Uber and the lobbying there, and then, of course, there was the whole Twitter

00:52:17 Andrew Keen: thing as well. Who were in the city,

00:52:19 Jonathan Weber: right? Well, and that came a little later, but there was the right, and so, right, there's the Twitter thing, where they had, again, a specific need, like they needed, you know, they didn't want to have to pay $50 million of payroll tax, when they did their IPO, so they wanted, you know, this tax break, and this was free,

00:52:35 Andrew Keen: pre-Musk to be clear,

00:52:37 Jonathan Weber: pre-Musk, right, 2010 So, so the tech companies were focused on a small set of issues that affected them directly. Now, what changed later on in the decade was, and with, like, Prop C, the homelessness thing that was that Benioff got behind, what you had later in the decade was the tech people getting interested in the more the totality of issues of political issues in the city, like homelessness, which doesn't, you know, isn't really per se something that affects the business of a tech company, other than you know, any different than it affects anyone else in the city, so, so in the late 2000 10s, that and up to the present, the tech companies really started getting much more involved on a more macro level in like politics, like we want, we want people who support our bigger agenda around you know, social issues and drug use and homelessness and all those things, and so you know that's a tall order, because these problems are not very easy to deal with, and Prop C, you know, Benioff in 2018 there was an initiative to put a new tax on big companies to fund homelessness response, and most of the business community hated it. Marc Benioff at Salesforce got behind it in a very big way, and, and that was kind of an example of the troubles, right, because Benioff got behind it, but he wanted to give enough money, so it would get two thirds of the vote, so there wouldn't be a legal challenge, but it didn't make two thirds, so it passed, and then all the money, so the tax was imposed, the money was collected and put in escrow, so then the tax, so basically all the companies were pissed off because they had to pay all this new tax, and then the homeless advocates were also pissed off, because nothing was being done with the money, so the money was sitting there, so you have kind of the worst of both worlds, and it's one of the reasons London Breed lost the election.

00:54:47 Andrew Keen: Yeah, and it speaks, I think, to the limits of the technocratic approach to politics. Travis may have fixed the taxi business. The guys at Airbnb may have fixed the hotel business, but technocratic solutions, algorithms, websites, they can't fix the city business, can they? [as spoken]

00:55:12 Jonathan Weber: No, no, they can't, and even something like Texas, you know. And if you look at the experience of taking an Uber today in San Francisco, it's vastly different than, so, in 2012 you could call an Uber, you know, they had practically three of them would come at once, you know, and take cost you eight bucks, you know, to go all. Way across town, you know, now you call an Uber, we maybe it'll come eventually, you know, the 25 bucks, you know, to go from here to the Mission, you know, so some physical things like you drive them across town, you know, the costs are what they are, it's very difficult to really, you know, solve those things with an algorithm, and you yeah, I think the, you know, the issues that around homelessness and the social problems in the city are not problems that are lend themselves to technological solutions, you know, there have been fleeting efforts, like Ron Conway got involved in tech for, like, gun technology, where you could, a gun wouldn't fire unless the owner of it is holding it, right? You know, these are like interesting tech solutions to the gun violence problem that will go nowhere because of the politics, you know. There are other technocratic, you know, you can, you can come up with certain ideas around, like how to build, like cheaper modular housing, or something, you know, high-tech approaches to construction, but these are still going to kind of run into the run into the political problems, and I think that there is a, yeah, you know, the tech people tend to think that, like, okay, here's a problem, let's find the engineering solution, but with a lot of these problems, there isn't, there just isn't an engineering solution, there has to be a political solution, and that's that's much more difficult,

00:57:10 Andrew Keen: and those arguments are laid out very clearly, you talk about them in the book in Ezra Klein and Derek Thompson's book, Abundance, which recognizes both the potential of tech but also its limitations when it comes to politics. Finally, Jonathan, you've been very generous with your time. We're in the midst of another massive boom, the biggest we're told of all time, with AI property prices in San Francisco, certainly in my neighborhood, seem to be going up 25 or 50% overnight. Is this any different? You end the book with Burning Man, with a trip you made to Burning Man, and we're just going to keep on going through these cycles, how will AI change San Francisco?

00:57:54 Jonathan Weber: Well, short answer, first question, I mean, yes, I don't, I don't really see anything that would, that leads me to think that the cycles are over, that we're at the end of history or something, and it's then it's

00:58:08 Andrew Keen: dramatically intensified because both OpenAI and Anthropic are based in the city, they're both supposed to be doing IPOs this year, so the consequences are likely to be, especially when it comes to real estate, likely to be quite dramatic.

00:58:22 Jonathan Weber: Yes, I think that's right. So we're likely assuming those IPOs go ahead, yeah, there's going to be huge influx, and it's going to send real estate prices, you know, really, really crazy again, and that's going to create a lot of tensions again. I mean, it is the case that, that more and more of the, you know, the city is gradually getting more uniformly wealthy over time, and so it's possible that some of those conflicts, you know, might be less intense, but, but I'm not really, I'm not really sure about that. I think we're going to continue to have this kind of dynamic, and, and you know, it's very hard to tell what, you know, the AI future. I won't try to make too many predictions, but, but I do think you can say from where we sit now that the current boom is going to bust in some way, and then that is going to create, you know, a new, you know, a new set of set of shifts.

00:59:24 Andrew Keen: Is it considerable that San Francisco be the first human-less city that actually works? Of course, now we talked about Uber and cars. One of the reasons you can't get Uber is because Uber drivers can't afford to drive for them anymore, and increasingly the rideshare industry is built around AI.

00:59:42 Jonathan Weber: Well, yeah, I mean, if you have, you know, the Waymo technology is obviously very good. So owned by Google, self-driving cars, that's clearly going to be a thing. I mean, you can automate, you can automate certain things. I don't quite see, you know, the one of the issues with automating things, and this is true with Uber, is the question of not simply whether you can automate something, but the question is whether it's cheaper and more effective than some other way to do it, and so part of what we're seeing now with AI is like the cost of AI is starting to become clear, and people like, oh my god, you know, so. So, so I think that the kind of futuristic, you know, vision of this sort of fully automated city is actually pretty far away still, not, and not because we, not because it's not possible, it's just because it's not really economic to do it

01:00:52 Andrew Keen: on your end, so you end the book with a rather surreal trip you make to Burning Man, which isn't in San Francisco, it's in the desert, but somehow captures a spirit of San Francisco. Why'd you end with Burning Man?

01:01:06 Jonathan Weber: Well, so Burning Man is a kind of a metaphor, you know, through the book of metaphor the city, really, as well as being kind of a metaphor of a tech startup, and Burning Man as a, as an event, so Burning Man is based on the idea of like going out to the desert and building a temporary city and just kind of expressing yourself in whatever way you want to do, and building crazy things, and doing art, and doing whatever, whatever crazy stuff you want to do, and, and over time, the just as with the city itself, so the rise of the tech industry, and more and more money, so people got much more elaborate with their Burning Man installations, and then Burning Man got more expensive, and then it got way more expensive, and then the infrastructure got more elaborate, and so then you had a lot of the early Burning Man people were like, "Wait, what is it, these new rich people coming in with their big fancy busses, and you know, taking over our little thing, and it was very kind of similar to some of the arguments that you had around gentrification in the city, so those tensions arose on the on the playa, and then if you, if you kind of fast forward to the end of the book, where I'm, where the passage that you're referring to, and you know, one of my observations about Burning Man, and the evolution of it, and the tensions around it, is that the even though at the very beginning of Burning Man, back in the 90s, and people were excited about, like, oh, we bring the web out to the desert, just because it was hard to do, would be kind of interesting, but, but over time it became clear that the internet and that kind of being always connected and that was really like not in the spirit of Burning Man, I mean the whole idea of Burning Man is you're going to a place and sort of it's like a different planet, you're on a different planet being a different person doing a different thing for a week and you can't really do that if you're still like connected to your regular life over the internet, and, but you know, what are you going to do? Like, you can't really say, like, to Burning Man, can't really have a rule that says no internet, that wouldn't really make any sense. So everybody's got their cell phone out there, and therefore you don't have any, any of the kind of privacy or sense that this is a separate place that's not going to be, doesn't really intersect with my regular world, you know, and that's sort of gone, and so you know that, so I thought that was interesting, and in the same way for cities, like part of the power of cities, right, as they bring people together, and a lot of good things arise from that friction among people. With the internet, a lot of the things that once required people being together don't require people to be together anymore, and so therefore cities kind of become a little less essential in some way, if you don't have to come to the office. Well, why do you need downtown, you know? And so I think there is an existential question around, like, what is the future of the city in the age of technology.

01:04:29 Andrew Keen: Well, Jonathan Weber certainly left his heart in San Francisco. The book is out this week. It's an important read, and a wonderful read too, from one of Tech's most experienced and distinguished, illustrious journalists, City on the Edge: Technology, Politics, and the Fight for the Soul of San Francisco. Jonathan Weber, real honor to have you on the show. Thank you so much.

01:04:29 Jonathan Weber: Thank you, Andrew. My pleasure.

01:04:29 Andrew Keen: Hi, this is Andrew again. Thank you so much for listening or watching the show. If you enjoyed it, please subscribe. We're on Substack, YouTube, Apple, Spotify, all the platforms, and I'd be very curious as to your comments as well on what you think of the show, how it can be improved, and the kinds of guests that you would enjoy hearing or listening to in future. Thank you again.