I Know Why the Tech Broligarchs Went Full MAGA | The Daily Beast Podcast

With the rise of Trump, suddenly these kind of fringe figures, views. that are way out of the mainstream, those things became assets under under Trump. Certain long standing right wing figures like Thiel and David Sachs, who were suddenly vaulted to to really to the to the top echelons of power. And then you have people like Zuckerberg who kind of soar. And Zuckerberg in particular, is a guy who lacks a real moral center of his own. So 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 their business interests. and their financial interests and their power. There's a real, I think, a cynical approach to politics out of the part of a lot of the companies. Welcome to the Daily Beast podcast. I'm Hugh Doherty. I'm executive editor of The Daily Beast, and I'm filling in for Joanna Calls. Our guest today is Jonathan Weber, journalist and author of the brilliant.

new book City on Edge, which are 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. And 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 challenges 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 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. Thank you for having me.

I just want to hold up. This is the book we are going to be talking about. It's pretty amazing. I have I've been absolutely riveted. It's called city on the edge and it's about it's 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, Camilla Harris, Gavin Newsom, Elon Musk, Mark Zuckerberg I managed to make it to Z. And of course you've got Donald Trump. What what what should people know. about San Francisco and why it's so important? Yeah. Well, first off, thank you for the 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 is a very iconic city in America. It kind of stands for many things. And and it's a symbol politically at the moment of kind of the left wing. It's 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 is produced a number of top national politicians, obviously, most recently being Gavin Newsom and Kamala Harris. And the political culture of the city is not uniformly progressive. as as people think. It's a much more a diverse group. And in fact, both Harris and Newsom are actually kind. of moderates, centrists in the in the grand political firmament of the US.

I do think that the book provides some good insight about those politicians. and kind of how they came to power and what they're like and how they operate. 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 a guess. with Marc 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? Yeah, I, I think that's not a bad. That's not a bad summary. I mean, the short answer would be that these these companies got so gigantic. and the and the fortunes that, that that 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, about this issue is a woman named. Esther Dyson, who's a well-known investor. and kind of impresario of the of the tech world for a very long time. She's known all these people since they were in their 20s. And 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're so great and you just kind of lose your mind in a way. You just lose track of what's real and and what isn't. All right. I did see that, you know, over a very long period of time, you know, back in the 90s, it was a very different scene. 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 watch them absolutely get detached from reality.

And there's an amazing anecdote, actually, I just need to to to pass. 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, you know, 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. Sure. I'm in. I'm. Was that the sort of this sort of crazy wealth was that being played out, that was being played out in front of your eyes? Really? Yeah. And that 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 is 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 who are on the other end of that, of that dynamic. And and you see it again now with artificial intelligence, where the price of, of housing is just being bid up in an unbelievable fashion. And, and it's a big it's a big problem because the city can't really solve. the problem of, of high housing costs very easily.

That's a big long term problem that's built up over many, many years. And so that's going to create another new round of tensions in the city. The big name I really want to get into here is, is Donald J. Trump. You saw you saw the tech lords. not uniformly, but many of them go from being what I seem to be, as you said, San Francisco values kind of broadly seen as progressive to Trump. And we saw Mark Zuckerberg on Sunday night was at the spectacle.

on the South lawn of the cage match being played out by Ufcw. for Donald Trump's birthday with Marc Benioff is a very prominent character. in your book. And drifting slowly to the right. What happened to them? Why did they go Trumpy? Well, I think there are a couple of things. First of all, again, to go back to. just the kind of sheer scale of the money that was involved. And and I think that they saw that Trump was friendly to the, to the money. in a sense of lower taxes and less regulation, all those kinds of things.

So I think that was that was part of it. I think the social justice movement and the in the 20 tens. and Black Lives Matter and all the things that that came with. that there was a lot of pressure on companies to, to 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 and then that kind of turned. So with the with the second election of Trump,

it was sort of permission to throw all that out the window, which which. a lot of people didn't really like that those policies very much anyway. And so then so Trump gave, gave permission in a sense, to say, we don't care about all this social justice stuff. And that was something that the the mogul was attracted, attracted to the, 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 was a hippie. He was a liberal, a big Burning Man guy. You know, he typical liberal tech guy. But over time, he got very alienated by the left wing drift. of the of the Democratic Party and felt it had become very serious and, and kind of against what freewheeling San Francisco was about. And he and he supported Trump in the last election.

Marc, even 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 even Benioff. recently said, to the great chagrin of, of. of pretty much everyone who knew him. He said that maybe Trump should bring the National Guard into San Francisco. So even 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. You've mentioned Mark Pincus, and one of my what, one of the most intriguing anecdotes from the early days of tech. start? I think this is I think we're in we're sort of in the early, early two, not early 2000, mid 2000. And you see, Pincus, who had moved to the city, was immersing himself in it. And it's quite a remarkable way he's got to Merce himself in the city.

He and his friend Emily Morse, later a popular sex blogger. I will take your word for it. Pro 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? 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 permission. to be who you want to be, to do what you want to do. to to create your own world, your own lifestyle. People aren't going to aren't going to get on you about that.

It's like, okay, everyone can kind of do their thing. And so so that is actually attractive to technologists, right? Because a lot of technology development, it can be 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, so I think that. a satirical search for sex clubs to, to do videos to put on on the local cable access channel in San Francisco,

you know, that's a very San Francisco kind of kind of endeavor, I would say. So let's, let's talk about some of these big, these big characters. And we've talked about the attraction of the of 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 in the mission.

Marc 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 Europe, betrayal of them, and 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. they were living outside San Francisco. but determined to have a C in San Francisco.

more than a sea 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? Well, so. to speak, specifically about about founders. Well, Founders Fund is the venture capital fund that that is kind of the center. That'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, and then and David Sachs, who's one of the leaders. of the All In podcast, he's a he's a long time right winger. I mean, back in the Stanford days, he was the coeditor 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. Hoo hoo. With the rise of Trump, suddenly these kind of fringe figures who are very,

in many cases, including sacks and it was very obnoxious presence. on social media, really has views that are way out of the mainstream. Yet those. things became assets under under Trump. And so you had, you know, certain long standing. right wing figures like teal and. and David Sachs, who were suddenly vaulted to, to really to the, to the top echelons of power.

And then you have people like Zuckerberg who kind of saw and Zuckerberg. in particular is a guy who lacks a real moral center of his own. So, so he kind of shifts with the wind. And, and so he was a big liberal when, 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 and it's a strange thing to see. But, you know, what it looks like is just somebody shifting.

to whatever supports their their business interests. and their financial interests and their power. And the biggest I was going to say the biggest name to say that was Donald. Trump, but maybe the biggest influence or the most important sort of the. the sun in the center of this universe here is now Elon. And he features he also features very little in the beginning of your story. But in the end, by the end, he is a really significant figure. I just wanted to tell us,

well, tell us your impression of your own I guess, 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 standard back in the late 90s. He had his first company, zip two, 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 and he was he was a kind of a normal sort of modest in his attitude. And he one thing I remember about that, actually, is we we had a chat thing. going on with some Reuters clients on a chat service that we had. And, and normally. we would sit there and type the questions and he would answer and we would type in. But he wanted to take the keyboard himself, which was interesting. That seems prophetic. Yeah.

And so that was a perfectly, again, perfectly normal meetings. But then over time, you know, he is also someone who really changed in a, in a huge way. And I think that he's been quite a malign influence, certainly in San Francisco. I mean, he he literally destroyed the most important. new internet company in San Francisco in Twitter. He destroyed it for personal ideological reasons. And, you know, 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 the sort of San Francisco bashers. There was. almost a little bit of an industry that developed around a 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, and I think that their, 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 we want it for us. And so we want to kind of push out the poorer. people who make a mess and, you know, make the city less, 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 to say those are those are made up things. And 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 so that's all true. But the but the tech moguls have a very different view of what. San Francisco ought to be than, than most of the people who live there. That view of what San Francisco wants to should, you know what what they want San Francisco to be. It's kind of like it's a 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 the. they clearly have somebody in Trump that they believe is helping them along. Yeah. Well, you saw as an example with the rise of, of. Uber and Airbnb, two of the most significant companies in the early 20 tens,

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, for 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 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, to the tech industry. So they've they've kind of achieved important parts of that agenda. But as you say, they would really like situation where, first of all, they don't have to pay as much city taxes. because the city taxes business is fairly heavily.

They would like much, much harsher policies. on 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, some, some limits to that. So so that's really the the agenda, I think of that. 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 were talking. and while we are talking right now. But but they're definitely pushing this nationally. Yeah. And one of the, one of the funny things about about the Trump agenda. and his relationship to the business world is that on the one hand, people are attracted to the tech guys in particular, attracted to the agenda in, in in major ways. First of all, just lower taxes, right?

That's a big one. Anti-religious seeming anti regulation. Right. That's a that's a big one. And then just sort of the cultural attitude right. That we love business people making money as good as opposed to evil billionaires. Right. So 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 in these companies, you know, people go crazy. No, the government can't pick winners and losers. That's crazy. Why would you do this? You know, you know, 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, you know. So I think that's a real you know, there's a real, I think a cynical approach to politics out of the part of a lot of the companies, you know, they don't really believe things, you know, they just want things that are good for them. 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 describe them in more profane terms at one point, but the Google busses, the Facebook busses, and it's, it's it's sort of a metaphor for the tech odds don't care at all. They're like, we're going to send busses to pick up our workers. And. Right. And then they try and keep them secret.

It's a crazy anecdote. Yeah, yeah, yeah. No. And the busses were absolutely you couldn't really get a better metaphor, you know, the for the kind of priority of the tech industry. Right. You have these giant, giant luxury coaches, you know, driving around these neighborhoods, picking up selected people. and stopping at the city bus stops, and the city busses 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 no valley. And and it was kind of ironic. because San Francisco is a pretty environmentally conscious place. And, and so the people riding the busses, 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, and this business, you know, that scene that you're referring to. in the book where the, the companies are like,

yeah, we're not going to tell you what our routes are. because we don't have to and, you know, screw you. And and the that attitude is remarkable to see. But then the 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. The Daily Beast, we report all the time on the Trump administration, and often. we are confronted with over not telling you something. And in fact, the answer is on one of their social media, people actually worked out where all these busses were because.

the Facebook workers were saying on Facebook. And I imagine, I assume other workers were saying. on their social media, oh, I'm getting the bus at whatever time. It's kind of an absurd, surreal scene that everything's everything's out there. Right. And, you know, one other thing I'll mention about the busses, 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, you know, that that that Google had an idea that they wanted, you know, workers to live in the city, and then they'll. send these busses to pick them up, and that'll be good, because they'll like the city, and we won't have to build parking garages. and Mountain View. And 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, 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 can we get a bus? You know, I mean, that's sort of how it started. And and then it grew organically over time. And I think that that is actually characteristic of, of the way. that the tech force, it's a bit of a force of nature, the tech industry, you know, and it doesn't really operate. with the kind of intentionality that people sometimes attribute to it. It's just that the, the kind of the capitalist forces drive certain things. And the busses are kind of example of that.

And people living in the city. I mean, you know, Google got huge people wanted to live in the city. And so they did. And then it made sense to have busses. So there were busses, you know, but this, this was kind of a. a sort of organic development. It wasn't really anyone's plan. We all live in this, this trumpet 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 going, oh, this is really weird. And then you're like, oh, then it just seems normal, but you're you're writing this dispatch. from the future. Give people some advice. Can you push back on on this sort of tech world? How did San Francisco deal with this takeover by tech?

Yeah, yeah. Well, it's I mean, it's not an easy thing. San Francisco. itself is a relatively small city, and one of the 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 with these issues is to tax the companies. So San Francisco has a lot of business taxes that most cities don't have.

And the and so that seems to make sense. Right. That's the companies are wealthy. There's a lot of impacts on the city. So you tax the companies to 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, you know, 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, like 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 cost 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. on the blackmail that they, that they get from the, from the companies. And I also think that. that people kind of need to be sort of smart and open. minded about about what makes sense and, and what doesn't,

because there are benefits to technological advances. Right. In self-driving cars, as an example, you know, people are very much of two minds about that. Like there are people in San Francisco 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 are like, no, this is. this is awesome, and this is going to be the future. And why not have it here first, then 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 innovations. So I think part of the balance to be struck. for the cities is that you you want to encourage innovation. And actually cities themselves need to really innovate a lot more, but. 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. Let's talk about the other half of this.

Talks 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 them were powerful politicians in the country. First of all, why is why is San Francisco such a. a furnace that is churning out powerful figures? Because we are sitting here. I'm sitting here in New York. We I suppose we've got a president.

It technically is a Floridian. We've currently got the Senate minority leader, but it's actually there's actually. not that many big, powerful politicians in recent years who come from New York. San Francisco has, you know, outclassed everywhere unless it seems. I think there are two main answers to that. So the 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 but it's always been. the kind of the business capital and the political capital of California. until the 20th century was by far the most important city. And it kind of retained the title of sort of business. capital and, and political capital in some ways. And so as a consequence, if you are. if you're an elected mayor of San Francisco, for example, you are immediately in the conversation about being governor of California.

And if your 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 to the white House. Right. And so that is not present in most cities. So so it was a consequence of that. You know, people see that, right? That's an incentive thing. And so it's like oh okay. Well San Francisco politics has like big prizes attached to it potentially.

So, so so therefore it's it's long been very, very competitive political arena. And then that kind of competition can kind of create. a 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 the 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, you know, one of the greatest politicians. in American history, you know, up from his bootstrap, you know, 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 he California passed term limits, kind of basically because people were tired of Willie as Assembly Speaker.

And so then he ran in one as mayor of San Francisco in 1995. 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 so the the city has been run by the Willie I call, I call it the city. family. That's a term that William Will Willie himself coined actually.

So so it's kind of this system. It's sort of a machine, but a little bit different than that. And, you know, built on these very long term relationships and includes includes. the unions, includes the civil servants, includes really politicians on all parts of the spectrum in some ways. And and so that system that Willie. built was very kind of sophisticated. And and William himself was a tremendous talent spotter. So he, he and the Burton brothers, you know,

they, they, they picked these people, you know, they picked Nancy. Nancy Pelosi has the seat that was held by, by Phil Burton. So she was picked as like, you are the one that's. going to going to carry on this, this legacy. You know, Barbara Boxer was obscure. Marin County supervisor was was picked. to be first congressman and then and then a US senator. So 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. 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 actions. He wants to win a Democratic primary and then he wants to get into the white House. Can he do it? I have long been very skeptical about Gavin Newsom's chances.

of being elected president, just because I think it's. very tough for San Francisco Liberal to be elected president. But and Gavin has flaws, which I point out in the book. I mean, I think he's 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, can really, you know, get the hard things done.

So I'm critical of Gavin in that regard. However, he's an extraordinarily talented politician. He's he's a 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 and the red states, when Gavin first said, okay, we're going to do this.

And there was a lot of a lot of skepticism, a lot of pushback. California was very proud of its nonpartisan, distracting system. People like Arnold Schwarzenegger were very opposed. And so at first it looked a little bit like my past might not. But then Gavin Gavin leaned into it. and made a great case for it at one, very easily. So. 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. as going into the presidential race, but I,

unlike my view, is really shifted a little bit from a year ago. A year ago I would have said, no chance. Now I think a chance. 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 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, prey. to self on hard work and her track records in the courtroom.

I had no idea she didn't. Underwear model. This is a bombshell. Yeah, well, that was a that was a classic. That was a magnificent quote from a Chronicle profile of Kimberly Guilfoyle. She has buried this. She has gotten prominence. She 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 over. She was not, you know, and so people the media kind of was like, oh, who's this Kimberly Guilfoyle?

And that was what the Quran came up with. But, you know, she was also the daughter of a of a political power player. in his own right. And yeah, it's a kind of a strange story, because obviously when Gavin married her, she was not a Trump 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 there's a notorious picture. I thought you were going to show the notorious picture of him. Can I have it in Kimberly Guilfoyle on the on the carpet in the Getty Mansion? And you people will see a lot of that picture if he does. I was about to mention the picture, but I have a big warning on the picture.

We can't afford to show it on on on on YouTube. It is very expensive to reproduce. And we are we are independent media. We are. We carefully count every one of our pennies so that we can. produce these shores. I will just say to people, I rarely say to people, Go and Google, it's worth it. This one is worth it. Google Gavin Newsom, Hearst Mansion, I believe. carpet Kimberly Guilfoyle yes yeah yeah yeah you'll find it.

Yeah, yeah. It was quite a 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. Can I sure he greatly regrets. 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 but the big question is, is, is this a liability for Gavin Newsom? Is she a liability?

You talk about one's turning up for an event, and. there's a notorious scandal. of an affair with a with with a coworkers wife. There's a 19 year old girlfriend when he's in mid 30s. Is this all going to be bad for him or does it not matter? Well, I think so. Leaving aside Kimberly Guilfoyle for a second. And so just talk about the scandals, I think the scandals at one time. would have been very damaging. But but now, you know, it's hard to it's.

hard to out scandal Trump I mean so. nothing that Gavin has done is nearly as bad as many things that Trump has done. So so therefore like I think. those issues are not issues in the way that they were. And 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 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, like 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 as like, really, Gavin? I mean, in perhaps a nuisance defense, San Francisco was the first city where love meant love. He may have taken things too far there, but I was the next. the next big figure that was 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 maybe even further back. But but to be the first female, the first black, the first Indian American, Vice. President Kamala Harris has gone further than anyone else. You obviously saw her close up for many, many years. What do you think her prospects are now?

I think that she. has a. reasonable chance of of of being the nominee again. I wouldn't I, 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 we're going to know. we know for 45th and 47 president. So yeah. Yeah. But the way that she lost and you can say, well she didn't really have a fair shot. at it because she only had three months. So, so I think it's possible that that, 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, you don't that doesn't happen if you are not a hell of a politician. And and she's 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. So she's very talented politician and really a, I mean, a literal protege. She was Willie's girlfriend, but but even beyond that, she's a protégé 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's what she's not so good at.

And the reason that I think one of the reasons that that that she lost. and her big weakness. really, is that she it's hard to tell what she really stands for. She 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 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, you know, so she was kind of a triangulate crime, but for criminal justice reform, but also tough on crime, you know, so kind of z zagging, you know, so that kind of indistinct identity, that's a real liability. for we can't rule out, as you say, she's 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? Well, it's going to be fascinating. I mean, I think they both are going to be. candidates and 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, more focus on on others, but it'll be really interesting to see how 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 but they're certainly rivals and it's. going to be quite interesting if they're really going going head to head. I just talked a couple of the other one of the other big names, which I just mentioned, obviously Nancy Pelosi, she isn't actually. I just think she's not a huge character in this book because she's always in DC,

but she seems to have learned lessons from this, 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 that sort of ability to, to, to, to climb the rungs of power, perhaps much more discreetly than Gavin Newsom and Kamala Harris.

Well, you know, that's a good question. I mean, Willie Brown, when I spoke to him for the book, you know, he's kind of critical of the of the current class of politicians, thinks the talent level is is kind of 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, here are future presidential candidates. So I don't I don't really know if the if the system, if San Francisco can continue to produce that that level of talent. You know, you mentioned the money. And one important factor in all of this was the the Getty family in particular. So they were back in the day. They were the richest family in the in the country. There would go back 30 years. And, and the Gettys are very implanted in San Francisco and they 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 they played a huge role in Gavin Newsom's. career, played a huge role in Nancy Pelosi's career. You know, they were friends with these people from way back. And so once somebody like Pelosi got to a certain point, they could. 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, you know, whether the Gettys will continue to play that role. Probably not. But just because they're old and died. And, you know, 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, you know, 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 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 and then there was a primary. And then just at the very end of the primary, she she endorsed Connie Chan, who's a progressive. Nimby member of the Board of Supervisors. And. I found it an odd, very odd endorsement, oddly timed, and.

I don't really know what that was all about. And you also, you also covered. the tragedy of Dianne Feinstein, of course. Yeah. And I 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, and disconnect from the realities of the world,

you know, 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, and, and it certainly played out that way. And I think that kind of thing that was very damaging to the, to the party. And, and, you know, Nancy Pelosi did the same thing, you know, so we you know, we had just had a situation where the party. suffered a catastrophic defeat because people were too old. And then and then the other party leaders who were too. old somehow couldn't take that lesson.

One of the other things that's happening in California. right now is there is, of course, a. 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. PR 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 in San Francisco here is, for the first time in many, many years, San Francisco isn't in this conversation. Yeah, well, I think it was a. 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 than the alternative.

But yeah, so but 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, you know, it's 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 very, very strong.

And I think it's very, very unlikely that Steve. Hilton can make a serious contest out of it. I mean, if a different candidate, if a different candidate than him. I mean, might, you know, I wasn't 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 but the Democratic lean in the state is so strong.

that it takes a really good candidate on the other side to win. Coming back to San Francisco, one of the one of the scenes. about this nation, but particularly about San Francisco, is that America only has three cities. New York, New Orleans, San Francisco, and the rest of it from Tennessee. Williams is slightly cruel, so I apologize 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 city on the edge, Jonathan, is it really is on the edge. It's like on the edge of the future. You've you've got this. You can you can see what's going to happen. Those, those driverless cars are going to come to our streets. Those Ubers are come to our streets. Are those Airbnbs have gone, have gone into 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. Well, certainly the. the AI impacts are very, very significant. And we're starting with. some of the most significant early impacts actually come in the tech industry. So, so in the traditional software businesses that have were really central. to the to the big booms of the 20 tens,

those companies are all cutting back employees very quickly. So so the. AI is coming for the jobs, right? That's a bit of a cliche, but it's coming first for the tech jobs. So that's that's ironic but but true. So that's something that people should keep in mind. And then I think, you know, these issues around, you know, how should the city manage the relationship with its businesses.

You know, you know, these are these are kind of perennial problems. But I think I think there are a few lessons that. that San Francisco can offer some other cities. And one of them is that for the city government, like, don't lose. sight of the basics because I think the the city got itself from a lot of trouble. The government really created 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 innovating.

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. You call it the city of. I believe it's a bit from the noise. Yeah, yeah, they called it because of the noise that the tools make, you know? And so that's a kind of a problem that's not that hard to solve, but a bunch of surveillance cameras and, and and other things. So, so I think that a lesson is like if the government loses control.

of, of very, very basic issues of street cleanliness and street safety, like the, then the government loses credibility and, and that that creates. all kinds of problems. So I think a lot of the tension in the city, you know, kind of. in most recent years, you know, kind of spring from that. So I think that's that's one lesson. The second lesson would be that. the managing this, 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. they can actually drive a harder bargain than they than they think, because the 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 burbs somewhere.

And and secondly, you know, there are there. there are a lot of benefits, potentially, if the city is nice to being. being in the city. So so I think cities kind of have more assets than they appreciate. sometimes and can can push a little harder on something like that. I've got to say, there are a few more beautiful cities. than San Francisco, and I say that with great affection for New York. It's beautiful summer day here. I. I love this city, but when whenever you go as a visitor, obviously I'm somebody has not lived in San Francisco.

But whenever you go with 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 a Golden Gate Bridge. It's the it's the water, it's Alcatraz. But there's this incredible fulcrum of the future happening. Yeah. Well, it's. Yeah, the physical beauty of the of the place. can't really be underestimated as a 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 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 to create, to innovate, to be, to be free, to think different. You know, the Apple ad cliche, you know, so.

so it's got, you know, it's got those, those very special dimensions to it and, and they're, you know, in 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 the culture that that I was referring to. of kind of free, willing, experimental, experimental and. try new things and, and. that 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. It's that kind of creates a lot of tension. So I notice you did not say the tech gods want to make it great again.

It's already great. It's a great city. And one of the, you know, even in the worst of times. Right. Even in the worst of the of the the doom loop days in 2022, a lot of the problems, 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. So in some ways, the, the public perception of, of the disaster.

that is San Francisco was, was quite exaggerated I think. So. So then people go there, you know, 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. Well, Jones, 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 probably visit San Francisco as well, I think. Right. And if you 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. Jones, thank you so much for joining us. Apologies to the people of Cleveland, but a bit a big problem to you as an author. It is a highly recommended book. Thank you for joining us. 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 Weber. Very nice. Thank you for joining us, Michael. Yes, yes. All right. Well, thank you very much. You. It's been it's been a pleasure. That was a. fascinating, gossip filled dispatch from the American future. There's even tips from Jonathan Weber. And what you should do. when trumpet chords come to your town in their self-driving cars.

Joanna will be back tomorrow with the unmissable David Rothkopf. on The Daily Beast podcast. Thank you to all our subscribers. If you are not a subscriber, smash that button though. It helps us to reach more people with great guests like Jonathan Weber. And finally, thank you to our brilliant production team Ryan Murray, Jonathan Romero, Rachel Passer, Heather Pissarro, 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.