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- [00:01]
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Hugh Docherty
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Jonathan Weber
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Hugh Docherty
Is it sweet?
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Jonathan Weber
Mmm, delicious.
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Hugh Docherty
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- [01:29]
Jonathan Weber
With the rise of Trump, suddenly these kind of fringe figures, views that are way out of the mainstream, those things became assets under Trump. Certain longstanding right wing figures like Thiel and David Sachs who were suddenly vaulted to really to the top echelons of power. And then you have people like Zuckerberg who kind of saw Zuckerberg in particular as a guy who lacks a real moral center of his own. So he kind of shifts with the wind. It's a strange thing to see, but you know what it looks like is just somebody shifting to whatever supports their business interests and their financial interests and their power. There's a real, I think, a cynical approach to politics on the part of a lot of the companies.
- [02:19]
Hugh Docherty
Welcome to the Daily Beast Podcast. I'm Hugh Docherty, I'm executive producer, editor of the Daily Beast and I'm filling in for Joanna Coles. Our guest today is Jonathan Weber, journalist and author of the brilliant new book City on Edge, which our own Michael Wolff calls a riveting tale. We are going to talk about San Francisco, the city which has given us some of the biggest names in American life right now. And we have Some dynamite gossip about a couple of them. We are going to reveal why the tech lords went mad and then went Trumpy. We're going to name who in Trump's inner circle was an underwear model and who posed on a rug with Kimberly Guilfoyle. And we're going to talk about why San Francisco might be the place which produces not one, but two Democratic challengers for the Oval Office in 2028. But before we dive into the show and a brilliant dispatch from the future, please take a moment, share this podcast with your friends, invite them to subscribe to The Daily Beast YouTube channel. We are closing in on Saturday, 700,000 followers. With your help, we can get to 1 million. Jonathan Weber, welcome to the Daily Beast podcast. Thank you for joining us.
- [03:28]
Jonathan Weber
Thank you for having me.
- [03:29]
Hugh Docherty
I just want to hold up. This is the book we are going to be talking about. It's pretty amazing. I've been absolutely riveted. It's called City on the Edge and it's about, about the city of San Francisco, but it's really about modern America was my conclusion. It's an amazing story. There are some names, I just want to get some names out there that are in this because it's the most incredible A to, well, A to Z, I guess, of everybody that's important. You've got everybody that's significant. You've got Nancy Pelosi, Kamala Harris, Gavin Newsom, Elon Musk, Mark Zuckerberg. I managed to make it to Z. And of course you've got Donald Trump. What should people know about San Francisco and why it's so important?
- [04:21]
Jonathan Weber
Yeah. Well, first off, thank you for the kind words on the book. I appreciate it and it's a pleasure to be here. And I do think you're right that the book, it's about San Francisco, but I think it really says a lot about America. And San Francisco is a very iconic city in America. It kind of stands for many things and it's a symbol politically at the moment of kind of the left wing San Francisco values. Nancy Pelosi are kind of held up as often kind of parodied around San Francisco values and progressivism. But the real political story of San Francisco is a bit different than that. It's a very sophisticated political machine that has produced a number of top national politicians, obviously most recently being Gavin Newsom and Kamala Harris. The political culture of the city is not uniformly progressive as people think. It's a much more diverse group. In fact, both Harris and Newsom are actually kind of moderate centrists in the grand political firmament of the U.S. i do think that the book provides some good insight about those politicians and how they came to power and what they're like and how they operate.
- [05:39]
Hugh Docherty
I think the other thing that is huge in the book is we're just talking about A to Z. And I should have started, I guess, with Mark Benioff. He's nearest to a the tech lords. It is absolutely stuffed with amazing stories about the tech lords. And I think I'm just going to put this really crudely. You've been in San Francisco since 1990, before there were tech lords. You watched them rise. And the way I read this book, you kind of watched them go mad. What happened.
- [06:12]
Jonathan Weber
Yeah, I think that's not a bad summary. I mean, the short answer would be that these companies got so gigantic and the fortunes that the top moguls have earned are so stupendous, almost unthinkable amounts of money and the consequence of that is to really separate them from the world. They're really not part of the normal world that you and I occupy. One person that I quote in the book about this issue is a woman named Esther Dyson, who's a well known investor and kind of empresario of the tech world for a very long time. She's known all these people since they were in their 20s. And her analysis is basically you get surrounded with all these yes men and layers and layers of security and protection and people telling you you're so great and you just kind of lose your mind in a way. You just lose track of what's real and what isn't. I did see that over a very long period of time back in the 90s. It was a very different scene.
- [07:18]
Hugh Docherty
So obviously what really animates this and the big name that kind of hangs over the story of modern America and the story, I guess, of San Francisco is Donald Trump. You watched them absolutely get detached from reality. And there's an amazing anecdote actually I just need to pass on from the book, which is that you watch the Mission and how that area had once been heavily Latino and very much a blue collar and middle class area of San Francisco. And the tech people started moving in. And in 2012, Mark Zuckerberg put down $10 million for a house in Dolores Heights and the estimate of the value of the house was only 3.2 million. I mean, if that's not detachment from reality, I don't know what is. When you go, oh, I fancy living there. Three times the value.
- [08:10]
Jonathan Weber
Sure.
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Hugh Docherty
I'm in was that sort of crazy wealth? Was that being played out? That was being played out in front of your eyes, really?
- [08:18]
Jonathan Weber
Yeah. And that is one of the things that created, as you can imagine, a certain amount of social tension. I mean, people felt like this was an invasion. People like Zuckerberg coming in, knocking on someone's door, saying, I want to buy your house. Well, the house isn't for sale. Well, how about 5 million? Well, how about 10 million? I mean, that kind of dynamic is very alienating for the people who are on the other end of that dynamic. And you see it again now with artificial intelligence, where the price of housing is just being bid up in an unbelievable fashion. And it's a big problem because the city can't really solve the problem of high housing costs very easily. That's a big long term problem. It's built up over many, many years. And so that's going to create another new round of tensions in the city.
- [09:09]
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- [09:38]
Hugh Docherty
The big name I really want to get into here is Donald J. Trump. You saw the tech lords, not uniformly, but many of them go from being what seemed to be, as you said, San Francisco values, kind of broadly seen as progressive, to Trumpy. And we saw Mark Zuckerberg on Sunday night was at the spectacle on the south lawn of the cage match being played out by UFC for Donald Trump's birthday. With Marc Benioff as a very prominent character in your book and drifting slowly to the right. What happened to them? Why did they go Trumpy?
- [10:16]
Jonathan Weber
Well, I think there are a couple things. First of all, again, to go back to just the kind of sheer scale of the money that was involved. And I think that they saw that Trump was friendly to the. To the money in a sense. Lower taxes and less regulation, all those kinds of things. So I think that was part of it. I think the social justice Movement in the 2010s and Black Lives Matter and all the things that came with that. There was a lot of pressure on companies to make certain kinds of policies internally, things they didn't necessarily want to do, but they did because their employees were demanding it. And then that kind of turned. So with the second election of Trump, it was sort of permission to throw all that out the window, which a lot of people didn't really like those policies very much anyway. And so then, so Trump gave permission in a sense to say, we don't care about all this social justice stuff. And that was something that the mogul was attracted attractive to the moguls because they were kind of sick of being told they had to do this or that, sick of being criticized for being rich. One person I talked to at some length is Mark Pincus, who was the founder of Zynga. And Mark was a hippie. He was a liberal, a big Burning man guy. You know, he a typical liberal tech guy. But over time, he got very alienated by the left wing drift of the Democratic Party and felt it had become very censorious and kind of against what freewheeling San Francisco was about. And he supported Trump in the last election. Even Marc Benioff, who has been a hardcore liberal supporter of many liberal causes, has kind of made that part of the philosophy of his company of Salesforce. And even Benioff recently said, to the great chagrin of pretty much everyone who knew him, he said that maybe Trump should bring the National Guard into San Francisco. So even a liberal like Benioff is kind of seeing the appeal of this sort of more pro business that's kind of intuitively attractive to these big bosses.
- [12:32]
Hugh Docherty
You've mentioned Mark Pincus and one of the most intriguing anecdotes from the early ish days of tech start, I think we're sort of in the early, not early 2000s, mid 2000s. And you say Pincus, who had moved to the city, was immersing himself in it. And it's quite a remarkable way he's got to immerse himself in the city. He and his friend Emily Morse, later a popular sex blogger, I will take your word for it, prowled the streets in a satirical search for sex clubs. I mean, it's kind of crazy, right? But there's a link, isn't there, between that and going Trumpy?
- [13:12]
Jonathan Weber
Well, yeah, I mean, I think so. San Francisco, a core of the culture, is a kind of a radical freedom almost, or permission to be who you want to be, to do what you want to do, to create your own world, your own lifestyle. People aren't going to get on you about that. It's like, okay, everyone can kind of do their thing. And so that is actually attractive to technologists because a lot of technology development can be pretty out there. And the government often has an interest in kind of controlling it. And so San Francisco was a place that gave permission, like, hey, no, go, do your thing, play with tech, all of that. So I think that a satirical search for sex clubs to do videos to put on the local cable access channel in San Francisco, that's a very San Francisco kind of endeavor, I would say.
- [14:06]
Hugh Docherty
So let's talk about some of these big characters and we talked about the attraction of them to the biggest character of all that we have in modern politics, which is Donald Trump for, you know, I was going to say for good or for ill, people can guess. But these big characters, Mark Zuckerberg set up a fort Zuckerberg in the Mission. Mark Benioff tried to put himself out there as a kind of liberal and then drifted off. Other people are, are perhaps slightly more sinister, if I'm honest, in your portrayal of them, particularly this new wave of Trumpy podcasters who have come from the tech world. And you talk about the all in podcast crew and how they were living outside San Francisco but determined to have a say in San Francisco, more than a say, to try and determine what goes on in San Francisco. I just wanted to talk about the sort of the mentality of these, of these people from the tech world and why do they think San Francisco is so important?
- [15:13]
Jonathan Weber
Well, so to speak specifically about Founders Fund. Well, Founders Fund is the venture capital fund that is kind of the center. It's Peter Thiel's venture capital fund and is kind of the locus of a lot of the sort of far right venture capitalists. And David Sachs, who's one of the leaders of the all in podcast. He's a longtime right winger. I mean, back in his Stanford days, he was the co editor of the Stanford Review, which wrote stories like talking about how women shouldn't be computer scientists because they couldn't do math and things like that. And so he's a well known, long standing, really a fringe figure on the far right who with the rise of Trump, suddenly these kind of fringe figures who are very, in many cases, including Sachs, it's a very obnoxious presence on social media, really has views that are way out of the mainstream. Yet those things became assets under Trump. And so you had certain longstanding right wing figures like Thiel and David Sacks who were suddenly vaulted really to the top echelons of power. And then you had people like Zuckerberg who kind of saw Zuckerberg in particular as a gu who lacks a real moral center of his own. So he kind of shifts with the wind. And so he was a big liberal when it was fashionable to be that. And then now he's a sort of chain wearing martial arts dude. Trump supporter has just kind of shifted his personality and it's a strange thing to see, but what it looks like is just somebody shifting to whatever supports their business interests and their financial interests and their power.
- [17:09]
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- [17:40]
Hugh Docherty
was going to say the biggest name decided that's Donald Trump. But maybe the biggest influence or the most important sort of the sun in the center of this universe here is now Elon. And he features, he actually features very little in the beginning of your story and but by the end he is a really significant figure. I just want you to tell us your impression of Elon, I guess.
- [18:02]
Jonathan Weber
But yeah, yeah, well, Elon, you know, he's always been a bit of a weird guy and you know, a lot of these people are, I mean, brilliant people in technology often have slightly odd personalities. But Elon, we wrote about him back in the industry standard back in the late 90s he had his first company, Zip2, which became part of PayPal. And, and back then he was a sort of normal, ish kind of Internet entrepreneur. And even as late as 2013 I met him when he came to the Reuters office and he was a kind of a normal sort of modest in his attitude. And one thing I remember about that actually is we had a chat thing going on with some Reuters clients on a chat service that we had. And normally we would sit there and type the questions and he would answer and we would type it. But he wanted to take the keyboard himself, which was interesting.
- [18:57]
Hugh Docherty
That seems prophetic.
- [18:59]
Jonathan Weber
Yeah. And so that was a perfectly, again, perfectly normal meeting. But then over time he is also someone who really changed in a huge way. And I think that he's been quite a malign influence certainly in San Francisco. I mean, he literally destroyed the most important new Internet company in San Francisco in Twitter. He destroyed it for personal ideological reasons. And it was a big company that had big headquarters in the middle of town and now it's gone. So that was certainly a huge negative and then he's been among the sort of San Francisco bashers. There was almost a little bit of an industry that developed around sort of shaming San Francisco as a symbol of dysfunction of progressive cities. And a lot of these right wing tech guys were really on that bandwagon. And I think that their attitude is that San Francisco is a very beautiful place. It's a wonderful place to live. And so we want to live there. We want it for us. And so we want to kind of push out the poorer people who make a mess and make the city less attractive. Now, this is not to say, I mean, the criticism of the city government and the problems in the streets that got much worse during COVID and homelessness, which people associate with San Francisco, all of those things are real problems. It's not to say those are made up things. And certainly the city government has a lot to answer for in its failure over many years to, to address some of these problems. So that's all true. But the tech moguls have a very different view of what San Francisco ought to be than most of the people who live there.
- [20:49]
Hugh Docherty
And that view of what San Francisco wants should, you know, what they want San Francisco to be. It's kind of like, I think they would call it like a sandbox, to use the tech term for what they want for America. I think that's one of the themes that comes through reading. You know, we're reading in this book about radical concepts about freedom and about libertarianism. But a lot of this seems to be that's kind of their agenda. And they clearly have somebody in Trump that they believe is helping them along.
- [21:21]
Jonathan Weber
Yeah, well, and you saw as an example, with the rise of Uber and Airbnb, two of the most significant companies in the early 2010s, and that was. They symbolized the kind of convergence of the tech industry and traditional government functions. Right. So now tech companies are really in the business of the city. And it was extremely important for those companies to get San Francisco in particular to go along with their agenda, because that was the test case, as it were, for many other places. So other places were to look to San Francisco, like what did they do in San Francisco to regulate these things. So it was very important for the companies to have friendly regulations in the city. And they largely achieved that under Ed Lee, who was a very tech friendly mayor, who was kind of installed by the powers that be, partly in order to be friendly to the tech industry. So they've kind of achieved important parts of that agenda. But as you say, they would really like a situation where, first of all, they don't have to pay as much city taxes because the city taxes businesses fairly heavily. They would like much, much harsher policies on drugs and homelessness and things like that. And they want really just kind of free rein on sort of whatever they want to do technologically, which even though the city has been fairly friendly, there are still some limits to that. So that's really the agenda, I think,
- [22:54]
Hugh Docherty
and that sounds very similar to the sort of. I'm going to give Trump more credit than I suspect he deserves here, but I was going to say the Trump agenda, but let's be honest, that can change with the wind. It's probably changed while we're talking right now, but they're definitely pushing this nationally.
- [23:11]
Jonathan Weber
Yeah. And one of the funny things about the Trump agenda and his relationship to the business world is that on the one hand, people are attracted at tech guys in particular, attracted to the agenda in, in major ways. First of all, just lower taxes. That's a big one. Seeming anti regulation. That's a big one. And then just the cultural attitude that we love business people making money is good, as opposed to evil billionaires. So they like the vibe of Trump towards business and they like some of these policies. One of the things that's been amazing to me is that Trump has pursued a bunch of policies, namely taking stakes in companies like the government having a piece of intel, for example, the government investing in quantum computing companies, and the government really being the heavy hand. Now, that's something that Republicans have always objected to vehemently, and business community in particular. I mean, the idea, like if you had floated five years ago, if you had floated the idea of the government, like taking stakes in these companies, people go crazy. No, the government can't pick winners and losers. That's crazy. Why would you do this? Da, da, da. But now that Trump is doing it and he's doing other things they like, suddenly it's like, well, okay, yeah, that's fine, we don't mind. So I think that's a real, there's a real, I think a cynical approach to politics on the part of a lot of the companies. They don't really believe things, they just want things that are good for them.
- [24:47]
Hugh Docherty
Yeah. And part of, part of the theme that kind of comes through to me on the subject of picking winners and losers is the tech lords really want to pick winners and losers. And, you know, I think it's a very strong theme in this book that the losers are kind of the normal people of San Francisco, there's an amazing bit of a sequence where the streets are suddenly flooded with. I think you described them in more profane terms at one point, but the Google buses, the Facebook buses, and it's sort of a metaphor for the tech odds, don't care at all. They're like, we're going to send buses to pick up all our workers, and then they try and keep them secret. It's a crazy anecdote.
- [25:34]
Jonathan Weber
Yeah, no, and the buses were absolutely. You couldn't really get a better metaphor for the kind of priority of the tech industry. Right? You have these giant luxury coaches driving around these neighborhoods, picking up selected people and stopping at the city bus stops. And the city buses have to wait while the luxury bus picks up the specified tech workers. So that really was very, very alienating, especially in the most affected neighborhoods in the south of the city, the Mission and Noe Valley. And it was kind of ironic because San Francisco is a pretty environmentally conscious place. And. And so the people riding the buses, like, previously, they had been driving their cars. So you'd think that that would be something that people would welcome, but it just didn't play out that way at all. And this business, that scene that you're referring to in the book where the companies are like, yeah, we're not going to tell you what our routes are because we don't have to, and screw you. And that attitude is remarkable to see. But then the city did really push back on that and eventually was able to kind of come up with some rules that mitigated the tensions a little bit.
- [26:48]
Hugh Docherty
The Daily Beast. We report all the time on the Trump administration, and often we are confronted with, oh, we're not telling you something. And in fact, the answer is, on one of their social media, people actually worked out where all these buses were, because the Facebook workers were saying on Facebook, and I imagine, I assume other workers will say on their social media, oh, I'm getting the bus at whatever time. It's kind of an absurd, surreal scene that everything's out there, right?
- [27:16]
Jonathan Weber
And one other thing I'll mention about the buses, which I think illustrates an important point, is part of the way that I see the tech sort of in takeover of San Francisco, I guess, for lack of a better word. But some people think of it as that it was a plot that Google had an idea that they wanted workers to live in the city, and then they'll send these buses to pick them up, and that'll be good because they'll like the city and we won't have to Build parking garages in Mountain View. But that actually is not at all the way it happened. I mean, it wasn't a plan. It was just some person at Google who kind of was sick of driving her car. And there were other people who also drove their cars and were sick of it and was like, can we get a bus? I mean, that's sort of how it started. And then it grew organically over time. And I think that that is actually characteristic of the way that the tech force, it's a bit of a force of nature, the tech industry, and it doesn't really operate with the kind of intentionality that people sometimes attribute to it. It's just that the kind of the capitalist forces drive certain things. And the buses are kind of an example of that. People living in the city. I mean, Google got huge, people wanted to live in the city, and so they did. And then it made sense to have buses. So there were buses. But this was kind of a sort of organic development. It wasn't really anyone's plan.
- [28:49]
Hugh Docherty
We all live in this trumpified tech world, but San Francisco is consistently ahead on it. I mean, you're the first, just as an example, first city in the United States, in fact, I think in the world to have driverless cars going around picking people up. And I don't know many people, I imagine watching this will have been to San Francisco and at least have seen them going around, maybe dared to get in them, and then gone, oh, this is really weird. And then you're like, oh, then it just seems normal. But you're writing this dispatch from the future. Give people some advice. Can you push back on this sort of trumpified tech lord world? How did San Francisco deal with this takeover by tech?
- [29:31]
Jonathan Weber
Yeah, yeah. Well, I mean, it's not an easy thing. San Francisco itself is a relatively small city. And one of the challenges for any cities, and especially a geographically small city, is that there's only so much you can do within your borders. So, for example, one way that San Francisco deals with these issues is to tax the companies. So San Francisco has a lot of business taxes that most cities don't have. And so that seems to make sense, right? The companies are wealthy, there's a lot of impacts on the city. So you tax the companies to mitigate those impacts. And that seems like a fair deal. But the problem is that a company can move three miles away and be in a different city that doesn't have those taxes. So they're always threatening to do that. And that kind of ties the company's hands or the city's hands a little bit. But I would say for the most part the threats of companies to move are mostly exaggerated. Those are kind of fear mongering. So, so for the most part companies don't move out because of taxes. I mean it does happen sometimes, it did happen in 2018, but mostly if companies move out, it's, you know, the costs of doing business in the city are very high for many reasons other than taxes, for one. So, so they move out for cost cost reasons or they move out for other reasons. The CEO lives out in the suburbs and he'd rather have his office nearby. So. So I do think cities should kind of stand their ground a little bit on the blackmail that they get from the companies. And I also think that people kind of need to be sort of smart and open minded about what makes sense and what doesn't because there are benefits to technological advances, right? And self driving cars as an example. People are very much of two minds about that. Like there are people in San Francisco who hate them and say, well, you know, why can't we just have taxi drivers drive us around? And that's fine, but there are other people who are like, no, this is, this is awesome and this is going to be the future and why not have it here first? And driving a taxi is a shitty job anyway. Why do we want to preserve that? You know, so, so there are people who are both suspicious of the tech industry but also kind of inspired by some of the, some of the innovation. So I think part of the balance to be struck for the cities is that you want to encourage innovation. And actually cities themselves need to really innovate a lot more, but need to do that in kind of a smart way that doesn't just kind of give the companies carte blanche to do things that may or may not be in the city's interest. And we're live on matchday. As Doug reaches for a buffalo wing. He's got it. Oh, and he's got gone for a can of Pepsi too. What a finish. There's no doubt about it. It just tastes better. Match days deserve Pepsi.
- [32:43]
Hugh Docherty
Let's talk about the other half of this. We've talked about the tech lords, but a city is a big bundle of different interests and different people. And the other big, big names, big characters right here in San Francisco are, as I said at the top, some of the most powerful politicians in the country. First of all, why is San Francisco such a furnace that is churning out powerful figures? Because we are sitting here, I'm sitting Here in New York, I suppose we've got a president. He technically is a Floridian. We've currently got the Senate minority leader. But there's actually not that many big powerful politicians in recent years who come from New York. San Francisco has outclassed everywhere in this, it seems.
- [33:34]
Jonathan Weber
I think there are two main answers to that. The first is that there's a particular dynamic in California where San Francisco, even though it's no longer the biggest city, it hasn't been the biggest city in a long time, but it's always been the business capital and the political capital of California. Until the 20th century, it was by far the most important city. And it kind of retained the title of sort of business capital and political capital in some ways. And so, as a consequence, if you are elected mayor of San Francisco, for example, you are immediately in the conversation about being governor of California. And if you're governor of California, you're immediately in the conversation about being President of the United States. So you can actually see a direct line from San Francisco Board of Supervisors to the White House. And so that is not present in most cities. So as a consequence of that, people see that that's an incentive thing. And so it's like, oh, okay, well, San Francisco politics has big prizes attached to it, potentially. So therefore, it's. It's long been very, very competitive political arena. And then that kind of competition can kind of create more highly trained players, as it were. And then the second big phenomenon is that there was a handful of exceptionally talented politicians. The main one over in recent decades has been Willie Brown. But there was what was known as the Brown Burton machine for Phil and John Burton, who were brothers, and then Willie Brown. Now, Willie Brown is perhaps one of the greatest politicians in American history. Up from his bootstrap, was a poor kid in a segregated town in Texas and worked his way up. And he was state assembly speaker for many years. Most powerful figure in the state in a lot of ways. And then late in his career, after California passed term limits, basically because people were tired of Willie as Assembly speaker. And so then he ran and won as mayor of San Francisco in 1999. Now, from 95 until 2024, each of the mayors was picked. So there was Willie, and then Willie picked Gavin Newsom. And then when Gavin went to Sacramento, Willie picked Ed Lee. And then when Ed Lee died, Willie picked London Breed. So the city has been run by the Willie. I call it the city family. That's a term that Willie himself coined, actually. So it's kind of this system it's sort of a machine, but a little bit different than that and built on these very long term relationships and includes the unions, includes the civil servants, includes really politicians on all parts of the spectrum in some ways. And so that system that Willie built was very kind of sophisticated. And Willie himself was a tremendous talent spotter. So he and the Burton brothers, they, they picked these people. They picked. Nancy Pelosi has the seat that was held by Phil Burton. So she was picked as, like, you are the one that's going to carry on this legacy. Barbara Boxer was an obscure Marin county supervisor, was picked to be first a congressman and then a US Senator. So the Brown machine was, had a lot of talent. They had figured out a lot of things about how to win elections, and they were extremely effective. And so a number of politicians came up through that system with a lot of skills and a lot of financial backing.
- [37:27]
Hugh Docherty
Well, let's talk about winning elections, because the name you mentioned there, Gavin Newsom, is a man who quite clearly wants to win, well, two elections. He wants to win a Democratic primary and then he wants to get into the White House. Can he do it?
- [37:41]
Jonathan Weber
I have long been very skeptical about Gavin Newsom's chance of being elected president just because I think it's very tough for a San Francisco liberal to be elected president. And Gavin has flaws, which I point out in the book. I mean, I think he's a great idea guy, an idea volcano, as one person called him. But he's not very good on the follow through, and he's not really very good at kind of building a team that can really get the hard things done. So I'm critical of Gavin in that regard. However, he's an extraordinarily talented politician. He's an excellent communicator. He has very good instincts about where to go at any given moment. And as an example of that, the redistricting ballot measure that passed earlier in the year, and when Gavin ramped that thing up in response to Trump pushing their redistricting in the red states, when Gavin first said, okay, we're going to do this, and there was a lot of skepticism, a lot of pushback, California was very proud of its nonpartisan districting system. People like Arnold Schwarzenegger were very opposed. And so at first it looked a little bit like might pass, might not. But then Gavin leaned into it and made a great case for it, and it won very easily. So I think he's someone who can't really be, can't be underestimated. I mean, I think he has A lot of liabilities going into the presidential race. But unlike my view, has really shifted a little bit from a year ago. A year ago I would have said no chance. Now I think a chance.
- [39:24]
Hugh Docherty
You talk about liabilities, you've got an epic bit of gossip in here about Gavin Newsom's first wife. To remind people who are watching, Gavin Newsom is now a happily married father of four to Jennifer Siebel Newsom, who's the first partner of California, but previously he was married to Kimberly Guilfoyle. She is as Trumpy a figure as you can possibly imagine. She is now the ambassador to Greece. She was, she was engaged to Donald Trump Jr. And I thought I could learn nothing new about Kimberly guilfoyle. But page 107, you in fact reveal Kimberly Guilfoyle was a bespectacled former underwear model who loves animals, prides herself on hard work and her track record in the courtroom. I had no idea she'd been an underwear model. This is a bombshell.
- [40:21]
Jonathan Weber
Yeah. Well, that was a classic. That was a magnificent quote from a Chronicle profile of Kimberly Guilfoyle.
- [40:27]
Hugh Docherty
She has buried this.
- [40:30]
Jonathan Weber
She had gotten prominence. She had got a little bit famous because she was a prosecutor prosecuting a dog mauling case. Terrible situation where two dogs had killed somebody. And but she came out, she was an animal, you know, and so people, the media kind of was like, oh, who's that? This Kimberly Guilfoyle? And that was what the cron came up with. But she was also the daughter of a political power player in his own right. And yeah, it's kind of a strange story because obviously when Gavin married her, she was not a Trumpian figure particularly. And it's not obvious what caused her to. I mean, she was ambitious as a media person and so she got a job. She was offered a job with Fox News in New York and she went to do that job. I think that being at Fox News kind of made her a much more right wing person. But, you know, there's a notorious picture. I thought you were going to show the notorious picture of him, David and Kimberly Guilfoyle on the carpet in the Getty Mansion. And people will see a lot of that picture if he does.
- [41:40]
Hugh Docherty
I was about to mention the picture, but I have a big warning on the picture. We can't afford to show it on YouTube. It is very expensive to reproduce. And we are independent media. We carefully count every one of our pennies so that we can produce these shows. I will just say to people, I rarely say to people go on Google. It's worth it. This one is worth it. Google Gavin Newsom, Hearst Mansion, I believe. Carpet Kimberly Gill file. Yes.
- [42:15]
Jonathan Weber
Yeah, yeah, you'll find it. Yeah, yeah. It was quite a notorious picture. You know, they had their moment as the glam power couple of San Francisco and they leaned into that with that silhouette with them. Sure. He greatly regrets.
- [42:29]
Hugh Docherty
Can I just say that our producers are both googling that image and giggling in front of me. So I invite everybody to do the same. But the big question is, is this a liability for Gavin Newsom? Is she a liability? You talk about once turning up for an event inebriated. There's a notorious scandal of an affair with a co worker's wife. There's a 19 year old girlfriend when he's in his mid 30s. Is this all going to be bad for him or does it not matter?
- [43:01]
Jonathan Weber
Well, I think they're so leaving aside Kimberly Guilfoy for a second and so just talk about the scandals. I think the scandals at one time would have been very damaging, but now it's hard to outscandle Trump. So nothing that Gavin has done is nearly as bad as many things that Trump has done. So therefore I think those issues are not issues in the way that they were. And weirdly, and this might have been a San Francisco thing, but it really, those scandals happened right before he was up for reelection and, and it didn't hurt him at all in San Francisco. So I don't think the scandals are, are too big of a problem, assuming that there aren't like others that we don't know about. But I mean the things that are known about I don't think will hurt him. There is an issue, I mean, something that sticks in my craw a little bit and I think some people will react this way is you sort of say, well, it calls into question his judgment a little bit to have been married to Kimberly Guilfoyle. So that, you know, that's a, you know, it's hard to, you know, it's hard to judge people in love. You don't really want to do that on one level. But it also, you know, you kind of look at it, it's like really Gavin, I mean, and perhaps in Newsom's
- [44:22]
Hugh Docherty
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- [45:01]
Hugh Docherty
say the next big figure that's worth talking about is Kamala Harris. And of all the figures in this, of all the characters that come from San Francisco in your book, she literally is the one that has gone the farthest in some ways. Of course, Nancy Pelosi is a far more powerful politician. Having been speaker, she's probably the most powerful speaker since probably Rayburn, maybe others, maybe even further back. But to be the first female, the first black, the first Indian American vice president, Kamala Harris has gone farther than anyone else. You obviously saw her close up for many, many years. What do you think her prospects are now?
- [45:45]
Jonathan Weber
I think that she has a reasonable chance of being the nominee again. I don't think it's likely, but I think it's possible. I mean, usually you don't get two shots at these things. So people say, well, you lost, so
- [46:02]
Hugh Docherty
we're gonna go, we know, for 45th and 47th president.
- [46:06]
Jonathan Weber
So yeah, yeah. But the way that she lost and you can say, well, she didn't really have a fair shot at it. Cause she only three months. So I think it's possible that she'll be able to come back. I mean, she is a brilliant political tactician. That's my analysis of Kamala and the fact that she rose to be vice president. I mean, that doesn't happen if you are not a hell of a politician. And she's very good at winning elections. She lost the presidential election. But if you look at what was stacked against her, you could say, I mean, I have my criticisms about how she ran the campaign, but if you look at what was stacked against her, she didn't necessarily do that badly. So she's very talented politician and really a literal protege. She was Willie's girlfriend. But even beyond that, she's a protege of the machine and has kind of learned the blocking and tackling that that machine really knows how to do, how to count votes, how to build coalitions. And so she's very good at that part of politics, which is a huge part of politics. What she's not so good at and the reason that I think one of the reasons that she lost and her big weakness really is that it's hard to tell what she really stands for. She doesn't kind of convey a strong belief system about where she's taking the world. She's very. She's very cautious in her policies, and she tends to zig and zag, you know, try to please everyone. That. That was very apparent when she was district attorney in San Francisco, where she was against the death penalty, but then there was a terrible cop killing. And then maybe she was for it, but maybe she was against it. You know, so she was kind of a triangulator, but for criminal justice reform, but also tough on crime. You know, so kind of zigzagging, so that kind of indistinct identity that's a real liability for.
- [48:07]
Hugh Docherty
We can't rule out, as you say, she is an incredibly skilled tactical politician. We can't rule out the possibility of a Gavin Newsom, Kamala Harris primary. What do you think would happen?
- [48:23]
Jonathan Weber
Well, it's going to be fascinating. I mean, I think they both are going to be candidates in what is going to be a very crowded primary field. And it'll be interesting. I suspect that they will try not to focus too much on each other and more focus on others, but it'll be really interesting to see how that unfolds. I mean, they've been kind of rivals. They pretend to be friendly, and I don't really know what their personal relationship is, but they're certainly rivals. And it's gonna be quite interesting if they're really going head to head.
- [49:01]
Hugh Docherty
Let's just talk a couple of the other. One of the other big names which I just mentioned. Obviously Nancy Pelosi. She isn't actually. I would just say she's not a huge character in this book because she's always in D.C. but she seems to have learned lessons from this city. And she certainly. This is one of the things I think is really significant. The amount of money in San Francisco is one of the things that clearly propels that forward. Is San Francisco going to produce another politician soon that's got that sort of ability to climb the rungs of power, perhaps much more discreetly than Gavin Newsom and Kamala Harris?
- [49:48]
Jonathan Weber
Well, that's a good question. I mean, Willie Brown, when I spoke to him for the book, he's critical of the current class of politicians, thinks the talent level is not what it was. If you look at the current crime, if you even look at the recent Democratic gubernatorial primary, if you look at some of the newer figures on the scene in San Francisco, you're not immediately inspired to like, okay, here are future presidential candidates. So I don't really know if the system or if San Francisco can continue to produce that level of talent. You mentioned the money. And one important factor in all of this was the Getty family in particular. So back in the day, they were the richest family in the country. We go back 30 years, and the Gettys are very implanted in San Francisco. And there's this whole social circle of old money wealth that kind of revolves around them. And they have been very active political, Democratic political donors for a long time. And they played a huge role in Gavin Newsom's career, played a huge role in Nancy Pelosi's career. They were friends with these people from way back. And so once somebody like Pelosi got to a certain point, they could count on major financial backing from the Gettys and the people around the Gettys. So that was also a big advantage for some of these San Francisco politicos. Now, I do think that there are. Whether the Gettys will continue to play that role, probably not. But just because their old Ann died and Gordon's very old. But. But there are other. Many other moguls now. You know, there's a lot of wealth in the city, so I don't think that money is going to be an issue if there's a real star out there. But it's not obvious who that star might be. You know, Nancy Pelosi played things very oddly, I thought, at the end of her term. She waited too long to retire. She's very old, she's very rich. She's really lost touch, I think, like many rich people have, she's opposed congressional ban on stock trading because it's benefited her tremendously. And she gets a lot of criticism for that, rightly so. And then I don't know what she was doing at the end here, but she, you know, in the race to succeed her. So she played coy for a long time. That made it very hard for successors to know how to position themselves. And then there was a primary. And then just at the very end of the primary, she endorsed Connie Chan, who's a progressive NIMBY member of the Board of Supervisors. And I found it an very odd endorsement, oddly timed, and I don't really know what that was all about.
- [52:51]
Hugh Docherty
And you also covered the tragedy of Dianne Feinstein, of course.
- [52:56]
Jonathan Weber
Yeah, and that was a very, very. It was both a sad situation and a very infuriating situation, honestly, because it was another example of where a politician, just because of her own Ego and disconnect from the realities of the world, thought it was a good idea to run for Senate when she was 86 years old for a six year term. And I thought that was a disgraceful decision and it certainly played out that way. And I think that kind of thing that was very damaging to the party. And Nancy Pelosi did the same thing. So we had just had a situation where the party suffered a catastrophic defeat because people were too old. And then the other party leaders who were too old somehow couldn't take that lesson.
- [53:47]
Hugh Docherty
One of the other things that's happening in California right now is there is of course, a gubernatorial race. On the one hand you have Xavier Becerra, who is an incredibly, honestly, low profile Democrat. And on the other you have Steve Hilton, who hails like me from the United Kingdom, but kind of bizarrely a bizarre tech figure married to one of the most powerful PRs in the tech world, a Fox News, occasional Fox News host, an eccentric advisor to British prime minister. And the thing that I think is relevant to San Francisco here is, for the first time in many, many years, San Francisco isn't in this conversation.
- [54:26]
Jonathan Weber
Yeah, well, I think it was kind of weird the way the gubernatorial primary played out. And it's funny because people had kind of thought Kamala Harris would run for governor. A lot of people, including me, were not necessarily that enthusiastic about that prospect. Although in hindsight maybe it would have been better alternative. But yeah. So Becerra is a very, as you say, low profile figure. He gets very poor reviews from people in the Biden administration over his performances. HHS secretary. He's a kind of a generic San Francisco or generic California Democrat without very conventional views, without much profile. So he's not really that great of a candidate. But the anti Trump sentiment in California is very, very strong. And I think it's very, very unlikely that Steve Hilton can make a serious contest out of it. I mean, a different candidate than him, I mean, might. You know, I'm not sure why Rick Caruso, the Los Angeles businessman, was talking about running for governor. Like, if he had run, I think he would have been a much more formidable candidate, actually. But the Democratic lean in the state is so strong that it takes a really good candidate on the other side to win.
- [55:48]
Hugh Docherty
Coming back to San Francisco, one of the sayings about this nation, but particularly about San Francisco, is that America only has three New York, New Orleans, San Francisco and the rest of it from Tennessee Williams, is slightly cruel. So I'll apologise in advance to anybody who wants to hear the rest of it. If you're from the Midwest, close your ears for a second. Everything else is Cleveland and I have huge affection personally for Cleveland. So I'm sorry about that. But what's fascinating about Citi on the Edge, Jonathan, is it really is on the edge. It's like on the edge of the future. You've got this. You can see what's going to happen. Those driverless cars are going to come to our streets. Those Ubers are coming to our streets. Those Airbnbs have gone into apartments beside us. People are living on AI models in San Francisco way more than they are in the rest of the country. Bitcoin is bigger, Crypto is bigger. Just give us a prediction. What does San Francisco right now tell us about what's going to happen next in the United States?
- [56:53]
Jonathan Weber
Well, certainly the, the AI impacts are very, very significant. And we're starting. Some of the most significant early impacts actually come in the tech industry. So in the traditional software businesses that were really central to the big booms of the 2010s, those companies are all cutting back employees very quickly. So the AI is coming for the jobs, right? That's a bit of a cliches, but it's coming first for the tech jobs. So that's ironic, but true. So that's something that people should keep in mind. And then I think these issues around how should the city manage the relationship with its businesses? These are perennial problems. But I think there are a few lessons that San Francisco can offer some other cities. One of them is that for the city government, don't lose sight of the basics because I think the city got itself in a lot of trouble. The government really create a lot of problems by losing control of basic stuff, you know, basic street safety, you know, car break ins, they sound trivial, but it really is innervating after a while that you can't, you can't park your car on the street without it getting broken into. This was almost a joke about San Francisco.
- [58:24]
Hugh Docherty
You call it the city of. I believe it's the bip from the noise.
- [58:27]
Jonathan Weber
Yeah, Bipping they called it because of the noise that the tools make. And so that's a kind of a problem that's not that hard to solve, but a bunch of surveillance cameras and other things. So I think that a lesson is if the government loses control of very, very basic issues of street cleanliness and street safety, then the government loses credibility and that creates all kinds of problems. So I think a lot of the attention in the city kind of in most recent years Kind of spring from that. So I think that's one lesson. Second lesson would be that managing this issue of kind of where the company is going to be and what kind of incentives are appropriate or not, and what kind of tax levels are appropriate or not. And I think that, I mean, it depends on the city, but certainly attractive cities like San Francisco, if they have downtowns that at least potentially can be attractive, they can actually drive a harder bargain than they think because the companies are first of all very influenced by what their employees want and their employees oftentimes want to be in the city rather than be out in the burb somewhere. And secondly, there are a lot of benefits potentially if the city is nice to being in the city. So. So I think cities kind of have more assets than they appreciate sometimes and can push a little harder on something like that.
- [60:01]
Hugh Docherty
I've got to say there are few more beautiful cities than San Francisco. And I say that with great affection for New York. It's beautiful summer day here. I love this city. But whenever you go as a visitor, obviously I'm somebody who's not lived in San Francisco, but whenever you go as a visitor, it is a beautiful city. It's, it's amazing that inside this beauty we all go, when we go as tourists, you're like, oh, it's the Golden Gate Bridge. It's, you know, it's the water, it's Alcatraz. But there's this incredible fulcrum of the future happening.
- [60:34]
Jonathan Weber
Yeah, well, the physical beauty of the place can't really be underestimated as a kind of part of its power. You know, it's really just kind of mesmerizing in its beauty in a lot of ways. And so, and so that's part of what creates so much attachment to it, right? Why people kind of care so much about the future of this kind of gorgeous, magical place. And then of course, on top of that, it's got this kind of exceptional culture of being the place where people go to do new things, to create, to innovate, to be free, to think different in the old apple, you know, so, so it's got, you know, it's got those, those very special dimensions to it and, and, and there, you know, and that kind of, it's a double edged sword because it's what makes city great. It also is what puts a lot more pressure on everything because first of all, people have a lot, a lot of people care about what the city does or doesn't do. So there's pressures in that way. A lot of People want to live there because it's such a beautiful place, makes it very expensive. And then of course, the culture that I was referring to of kind of freewheeling, experimental and try new things. And because that culture has kind of been so successful in the context of the tech industry and it's produced this tremendous amount of wealth that's made the city very, very expensive. And so that kind of creates a lot of tensions too.
- [62:11]
Hugh Docherty
I noticed you did not say the tech worlds want to make it great again. It's already great.
- [62:18]
Jonathan Weber
It's a great city. Even in the worst of times, even in the worst of the doom loop days in 2022, most of the problems in the city were confined to the center city area. And there were a lot of neighborhoods that were just fine and still very beautiful. And if you're walking across the Golden Gate Bridge, you would never really know about most of these problems. So in some ways, the public perception of the disaster that is San Francisco was quite exaggerated, I think. So then people go there and now things are a little bit better. And so now people go there and they're like, oh my God, the city's fantastic.
- [62:57]
Hugh Docherty
Well, Jonathan Webber, the book is the City is fantastic. The book City on the Edge is fantastic as well. If you can't visit San Francisco, you should buy the book, but you should probably visit San Francisco as well, I think. Right.
- [63:11]
Jonathan Weber
And if you visited San Francisco or you lived in San Francisco and you want to kind of understand the city and how it got to where it is right now, I think the book provides some insight there.
- [63:21]
Hugh Docherty
Jonathan Webb, thank you so much for joining us. Apologies to the people of Cleveland, but a big prop to you as an author. It is, I'd say, highly recommended book. Thank you for joining us. And I should say one final note, it is recommended by Michael Wolff, the co host of Inside Trump's Head. And I will just say from personal experience, it's very hard to get praise from Michael Wolff. He is extremely demanding, taskmaster and he calls your book a riveting tale which has turned San Francisco into an unforgettable character. Can't get finer words than that. Jonathan Webber, very nice. Thank you for joining us.
- [63:56]
Jonathan Weber
Very nice of Michael. Yes, yes. All right, well, thank you very much, Hugh. It's been a pleasure.
- [64:05]
Hugh Docherty
That was a fascinating gossip filled dispatch from the American future. There's even tips from Jonathan Webber on what you should do when Trumpy techlords come to your town in their self driving cars. Joanna will be back tomorrow with the unmissable David Rothkoff on the Daily Beast podcast. Thank you to all our subscribers. If you are not a subscriber, smash that button now. It helps us to reach more people with great guests like Jonathan Webber. And finally, thank you to our brilliant production team, Ryan Murray, John Romero, Rachel Passer, Heather Passaro and Neil Rosenhaus. So the good news is we have so many Beast Tier members now there are too many names to read out. And we really appreciate your support.
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