Unraveling The Mystery Of Peter Thiel — With Max Chafkin

Max Chafkin is the author of The Contrarian: Peter Thiel and Silicon Valley's Pursuit of Power, which debuts this week. The book is a fascinating, inside look into the life and rise of Silicon Valley’s most powerful and controversial venture capitalist. In this interview, we discuss whether Thiel is representative of Silicon Valley or an anomaly, and dig into who he really is and what motivates him. You can find the book here: https://amzn.to/3AwAKHB Learn more about your ad choices. Visit megaphone.fm/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Alex Kantrowitz?

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• 1:16Alex Kantrowitz?

  Hello and welcome to the Big Technology Podcast, a show for cool-headed nuanced conversation of the tech world and beyond. Our guest today is Max Chafkin. He is a Features Editor at Bloomberg Businessweek and the author of the brand-new book just hit shelves yesterday. It's called The Contrarian: Peter Thiel and Silicon Valley's Pursuit of Power. It's interesting that you also say one Silicon Valley, so we have to get into that. Is there one? Is there many Silicon Valleys? Is Silicon Valley a location? Is it an idea? Is it uniform? Does it contain multitudes? As the LA Times just spoke about your book. Anyway, Max, welcome to the show.

• 1:54Speaker 01

  Yeah, thanks for having me, Alex. I'm really excited to be here.

• 1:56Alex Kantrowitz?

  Thank you, Alex. You see, you already got me excited. I've learned so much from this book and I'm just thrilled to be talking to you. And I think this is going to be a fun discussion. So why don't we start here?

• 2:09Alex Kantrowitz?

  Peter Thiel is one guy. We see him in headlines every now and again. He's done a handful of things. Has he built the most impressive companies in Silicon Valley? I don't think so. Certainly a presence there. So why is he so important that you became obsessed in the way that got you to write a book? And we're about to spend about an hour talking about him. Why do people, if people are gonna listen to one of the episodes of this podcast, why would this be the one?

• 2:40Speaker 01

  Yeah, so I've got two answers. And one, the kind of quick answer is he's fascinating. He's somebody who's full of contradictions. You know, I think the thing that caught a lot of people's attention with Thiel as a figure of fascination, you know, in 2016, when he endorsed Donald Trump, right, there's this feeling of like this futurist, this prominent futurist who's a gay immigrant from California, is backing a reactionary, anti-immigrant, New York real estate developer who's running on a nativist platform. Like, that's weird and interesting. And to me, like, that is, I think, as obvious as that sounds, I think

• 3:22Speaker 01

  that's part of the kernel of why people care about him. But I mean, the real answer to your question is, and this is something that, you know, I thought about as I was writing the book and tried to develop it, but Thiel, I think, as you say, he's not the richest tech mogul. He hasn't started the best companies. There are certainly stories you could tell about the tech industry over the last 20 years where other people would be kind of in the main character and would be like the main character. But I would argue that Thiel has had a bigger cultural impact on the tech industry than any single person. And so

• 4:02Speaker 01

  like, by that, I mean, how the tech industry sees itself, how companies see what they do and how they do business. So, in other words, This idea that founders, that the class of the founder is this kind of special person who has a privileged access to kind of like what the company is supposed to do and who's right, who's just knows what's best. That came from Peter Thiel. I mean, that comes from Founder's Fund.

• 4:29Alex Kantrowitz?

  Right.

• 4:30Speaker 01

  And that ethos, I think, you know, goes a long way to explaining like a lot of the weird stuff that has happened in the tech industry over the last 20 years as the tech industry kind of spills into, you know, whatever the real world as Facebook.

• 4:46Alex Kantrowitz?

  Right, right. But Max, isn't it more than that, though? It's more than just trusting the founder, right?

• 4:50Speaker 01

  Of course.

• 4:51Alex Kantrowitz?

  It is, having read your book, it is in particular this libertarian impulse that he has.

• 4:58Speaker 01

  Absolutely.

• 4:59Alex Kantrowitz?

  Anti-institutionism.

• 5:00Speaker 01

  Right.

• 5:01Alex Kantrowitz?

  That essentially says, you know, screw the government, screw the rules, disruption is almost de facto good.

• 5:10Speaker 01

  Absolutely.

• 5:11Alex Kantrowitz?

  And that is something, I mean, he starts with the company PayPal, which you outlined pretty impressively, was yes, about sending money on the internet, but also in some ways breaking the global financial system.

• 5:24Speaker 01

  Yeah.

• 5:25Alex Kantrowitz?

  So, yeah, of course, he did this thing called Founder's Fund where he wants to empower the founder and he talked about, you know, how bad education is and paid people to drop out of school. But, you know, having read your book, my takeaway was that his core cultural impact on Silicon Valley was convincing people that, you know, they should and could break down the system in any way possible. And this is, you know, obviously do it for money. But to me, it seemed, you know, from his very early years, he had this libertarian, anti-institutionalist streak. And that extended, you know, to so many people he came into contact in Silicon Valley. And, you know, I wrote down a few that have worked with

• 6:05Alex Kantrowitz?

  him. You talk about Elon Musk, David Karp, Joe Lonsdale.

• 6:11Speaker 01

  Alex Karp.

• 6:12Alex Kantrowitz?

  David Sacks. Yeah, sorry, David Sacks, Alex Karp, Joe Lonsdale. I mean,

• 6:18Alex Kantrowitz?

  It's unbelievable how many people have sort of come into his orbit and seem to have walked away as theists, you know, from their, from the philosophical standpoint.

• 6:28Speaker 01

  I hundred percent agree with everything you just said, and I think you just put your finger on exactly, I'd say like the most important thing about Thiel's, you know, kind of ideology and identity is this idea, yeah, that breaking the rules, it's not just that it has neutral value, it's not just that it's, that the rules can be ignored, it's that there's something good about, about breaking the rules. And, and that, I think, you can sort of see why that would be useful if you're, if you're building a startup. But it's also, you know, obviously can have, you know, detrimental effects. And, and now we've created, and this is why I think it's really important to pay attention to somebody

• 7:10Speaker 01

  like Peter Thiel, and to pay attention to Thiel in particular, because that ethos, Thielism, if you want to call it that, is basically the, the main ethos of Facebook, of, you know, of, of most of the bigger companies in Silicon Valley, this, this idea that the rules, yeah, just aren't that important, and, and maybe it's best to, to cast them aside from time to time.

• 7:35Alex Kantrowitz?

  And he hated, it seems like he hated people who were pro-government, pro-institution.

• 7:41Speaker 01

  Yep.

• 7:42Alex Kantrowitz?

  In part because he was bullied as a kid, and was sort of an outcast, and, you know, he grew up in Silicon Valley, if I, if I remember correctly, and people didn't treat him well. And he was like, you are out there saying you're gonna go, you know, heal the world, and you know what's right, and your precious institutions, and, and this is the way you treat someone, I'm gonna wreck it. And that seemed to have defined a lot of what he did through life. Is that, is that a fair thing to say?

• 8:09Speaker 01

  Yeah, I think that's right. I mean, the Thiel family.

• 8:12Alex Kantrowitz?

  It's amazing how much comes back to bullying.

• 8:14Speaker 01

  It is, yeah, seriously. They were outsiders. His parents were German immigrants, very conservative, very religious. And he moved around a lot as a kid. They bounced from Cleveland to South Africa and then finally to Foster City, which is this suburb in the Bay Area, but it's pretty far removed from Silicon Valley.

• 8:39Alex Kantrowitz?

  Built on marshlands.

• 8:41Speaker 01

  Yeah, it's not the nicest. I think the houses there are pretty expensive, just like everywhere else, but it's kind of a world away.

• 8:48Alex Kantrowitz?

  Yeah, you can look at it as you're flying into SFO right out the window. That's what you look at.

• 8:52Speaker 01

  And so, yeah, he definitely, he was very smart and withdrawn and angry. And I think, some of that anger, like you said, it came from bullying and it kind of spilled into his sort of output as a human. First, as an undergraduate at Stanford, starting this kind of very hard, right-wing newspaper, The Stanford Review, and then continuing on throughout his career.

• 9:27Alex Kantrowitz?

  So here's what I'm puzzled by. So someone who grows up as an outcast and has this, "The world be damned" attitude, who wants to wreck things, how does he end up having the influence in Silicon Valley that influenced all the people that we just spoke about? By the way, let's add Mark Zuckerberg to the list. He funded Facebook and he's a Facebook board member.

• 9:49Speaker 01

  Absolutely.

• 9:50Alex Kantrowitz?

  If you're encountering a group of generally optimistic builders, how does this very dark attitude towards the world and its institutions take such a hold inside that community?

• 10:04Speaker 01

  So, one, I spent a lot of time thinking about this. I talked to a lot of former PayPal employees, and I think it's weird. PayPal has really, people know a lot about PayPal and tech. It's been kind of scrutinized a lot, I think rightly, but there's still things like that are probably underappreciated. And I think one is the extent to which there was this kind of band of brothers at PayPal, who were all from this conservative publication. Like, there were, like, it wasn't just, oh, Thiel starts a conservative newspaper and then, you know, goes to law school and then gets into tech. But like, he really brought along this whole crew of people. And, and their whole

• 10:47Speaker 01

  thing had been kind of us against the world. And that then became transposed, you know, into PayPal, where PayPal, you know, there was a political aspect to PayPal, which is something people overlook. You kind of hinted at it. But, you know, in the early days, they were talking about it, as you said, like, as this thing that would break the, not just the global banking system, but like, national sovereignty, that it would make it impossible for countries to regulate their, their monetary systems, to make it possible for people in repressive states to, you know, obviously to move money in or out easily. And, and so it was this, you know, overtly political thing. And then there were, you know, then

• 11:30Speaker 01

  there, then, then it, it sort of transposes into, you know, it's us against the corporatists. It's us against eBay, which, you know, for a long time, eBay bought PayPal, but for a long time eBay was there, was also their kind of main antagonist. And I think-

• 11:42Alex Kantrowitz?

  Right. He, he didn't, Thiel and Meg Whitman just weren't on speaking terms by the time that acquisition-

• 11:47Speaker 01

  No, I think there's like, that is a, yeah, they're, they're like, I don't know, opposite ends of the spectrum.

• 11:55Alex Kantrowitz?

  I mean, Thiel seems to have fought with everyone. I mean, he also fought with, with Elon and did a coup to sort of take-

• 12:01Speaker 01

  Yeah, exactly.

• 12:03Alex Kantrowitz?

  PayPal over him. So, yeah, I'm sorry, go, keep going.

• 12:06Speaker 01

  Anyway, I was just gonna say, these, when you talk to these guys about kind of like, what, you know, why was PayPal successful? One of the things they say is like, we had this kind of, we had this sense that it was like us against the world. There's this kind of a cohesiveness to, to the PayPal team. And I think that that kind of, you know, basically spun forward into the PayPal mafia, this, this kind of feeling that it's us against the world. Um, you know, I don't think people have noticed the, that political thing much, but like-

• 12:38Speaker 01

  I think a lot of the kind of, some of this kind of cult of disruption stuff that we see in Silicon Valley, probably best epitomized by like Uber or something, I think kind of has its roots in right-wing activist politics, the right-wing activist politics of the 1980s, which is like where Thiel did like his first, you know, it wasn't a business really, although I guess it kind of was a business, his first entrepreneurial venture. And, you know, in right-wing activist politics, you know, there's this like big tradition of, you know, kind of like screwing with the administration. There are all these stories of sort of news, college newspaper editors like going in and stealing, you know, lists of names from the registrar, or like, you know, sort of doing these like acts of protest

• 13:22Speaker 01

  or whatever, and sort of finding ways around the institutions. And I think that kind of spirit, you know, you can, you know, draw a line straight to some of the things that PayPal did, because PayPal totally just ignored every banking regulation. They, you know, it wasn't just that they were ideologically opposed to, you know, like the normal model of regulating currencies, they were just actively just, you know, saying screw it. And, and eventually, and they, you know, got away with it. I mean, I don't know if got away with it is the right word, but, you know, they were able to navigate the company to a successful exit and settle with the regulators and, and kind of integrate themselves into the global financial system. And I think, you know, the rest of the tech

• 14:07Speaker 01

  industry, you know, kind of learned a valuable lesson from that experience, which is that you can, you know, you can succeed by pursuing this sort of regulatory arbitrage, by attacking a regulated industry and by making one of your points of differentiation that you do not follow the rules.

• 14:25Alex Kantrowitz?

  So it's largely accepted as fact that Silicon Valley portrays itself as a save the world type of companies versus we're just doing this to make money. How do those two things look when you juxtapose them? The we're trying to take down the system and this, you know, we're here to heal the world, or some of the Zuckerberg language?

• 14:47Speaker 01

  So I think there are kind of two threads of kind of ideology that, and I argue this in the book, it's definitely up for debate, but here's how, but the way I think about it, right? And this is, was first suggested to me by Roger McNamee, who's a venture capitalist who, you know, has turned critic of Facebook. But, but basically you have kind of like the Steve Jobs way of thinking about companies. And I think this, I think obviously there's some hypocrisy here, but the basic idea is that business is a form of creative expression and it's a form, it's a way to like help people get the most out of themselves, like, you know, kind of new age human business as like new age human potential movement stuff.

• 15:30Speaker 01

  So Apple, of course, fits into that, but so does Google, right? You know, it's like we're, we're, we're making the world's information accessible, we're making you smarter, or whatever it is. And then there's this like other thread, which is the Thielist thread, which is business as disruption, business as power. And that is, you know, grow as big as you can and, and like, you know, get a monopoly. I mean, in that, you know, Thiel wrote a whole book, Zero to One, where the basic takeaway is, you know, businesses, if they want to succeed, they should, they should strive for, you know, monopoly profits, which is another way of saying, you know, dominance. And, and so I don't think those two things can be reconciled.

• 16:15Speaker 01

  I think they're, they're, they're like on two sides of the spectrum. And I think that, you know, obviously the Thiel view is very, very cynical, but of course, you know, a lot of these companies that say they're saving the world are actually, you know, they're just sort of saying, I don't know. I think you, I think both those frameworks are potentially useful to like, understand Silicon Valley and understand why it's grown so quickly and stuff.

• 16:41Alex Kantrowitz?

  Yeah, I think my, my theory on this is that Steve Jobs warped a lot of people's view of what tech is.

• 16:49Speaker 01

  Yeah.

• 16:49Alex Kantrowitz?

  And because he was so. Hard, so influential and so hard on the save the world mentality that everyone had this picture in their head that that's what tech is. In fact, I think you mentioned the tech press's influence, a bunch in the book, which I thought was great. And I think the tech press in large part wanted every founder to be Steve Jobs. I mean, you see what's happening with Elizabeth Holmes. It was her responding to those incentives and how many covers did she get wearing the turtleneck? While she was defrauding everybody. So I think that that was something that folks needed to, felt they needed to portray to the outside world. But if you looked on the inside, it was a teal mentality all the way.

• 17:27Speaker 01

  Yeah, yeah, yeah, for sure. And it's kind of funny, I went back and read a bunch of the, you know, whatever the output about the tech industry. You know, there are books written, you know, in the, in the early 2000s. And a lot of their essays and stuff all about how the, the role of the counterculture in forming Silicon Valley. Which I think is, okay, like it's totally valid and yes, like, yeah, Steve Jobs was a bit of a hippie. But it's kind of a weird way of looking at an industry that literally started as an extension of the US military. And, and like, like, you know, there's nothing, there is, there are countercultural things about Silicon Valley.

• 18:07Speaker 01

  But to see the tech industry as just this kind of outgrowth of, of 60s counterculture is like to miss, you know, the whole beginning of the industry and like, you know, a thread that probably is just as important as like, as you say, you know, something that kind of a little bit came down to branding or, or something like that, which is like these guys talking about saving the world. But, but I don't know, I mean, the real root is a, you know, a bunch of defense contractors.

• 18:33Alex Kantrowitz?

  Yeah, well, there, there's something to root for in the word disrupt. And I, I do think that the tech industry's claims that the, um, the way things have been done for a long time have been corrupt and hurt people. I think there's only doubt about that and they especially resonated in the time of. The financial crisis. I think you even talked about how you approached Thiel and you you asked him to participate in the How I Built This article. And you were talking about how it was a little schlocky, but we were looking for ways to be like, you know, there's got to be some optimism because the old way just brought down the whole economy.

• 19:08Speaker 01

  Yep.

• 19:09Alex Kantrowitz?

  But but there is, you know, you can see some some virtue in what these companies are doing. But that's where the story starts, but so many, so many times it actually gets actualized in this Thielist way, which is like, Thiel had a, I mean, from your, from your book, it's clear. He had a hate, hate, hate for institutions and eventually that came through in his recommendations once he got asked to help staff the Trump administration, which we'll get to after, after the break. But it is interesting to see how like, you know, it could start from a virtuous, virtuous place, but very often and in a bad place. And it seems like, you know, I don't know, it seems like Thiel had a had a large hand in that.

• 19:50Speaker 01

  Yeah, yeah, 100%. I also think, you know, there's something just like appealing about the honesty of the of the Thiel worldview, especially if you're feeling a little bit, you know, if you're feeling betrayed, like, like the the kind of post-financial crisis mode, if you're feeling betrayed by institutions, or if you're just kind of fed up with the hypocrisy of, you know, whatever of that's kind of inherent to capitalism, the the sort of cynical worldview of just sort of like, yeah, get as big as you can and make as much money as you can. And, you know, forget being good, like that has, I mean, I don't know. I mean, maybe it's because I'm a bad person or something, but I see the appeal. I, you know,

• 20:35Alex Kantrowitz?

  Yeah, I was gonna ask if some of this stuff resonated with you. I mean, institutions, I mean, look, I, I don't know, I feel like I tend to believe in institutions sometimes more than I should, but some of them are bad.

• 20:48Speaker 01

  Yeah.

• 20:48Alex Kantrowitz?

  If you look at the state of the country, and obviously, I don't think the Thiel mentality has helped us very much, but people have been let down by their institutions and they don't believe them anymore. And so the idea of burning them down is appealing in some way, even though it might not be the right solution. I really think that reforming them is the right solution, but I can see why burning them down has a real appeal among a lot of people.

• 21:11Speaker 01

  I mean, Thiel would not be. Would not have so many followers. He would not be dangerous if he wasn't right a lot. I mean, that's the thing about so like, I think, I mean, he was obviously the, you know, for instance, his, his critique of universities, right? It's, it has a lot, there's a lot of, of, of truth to it. Um, you know, universities have been, you know, overcharging people and have been, you know, uh, failing to prepare students and I, but is the answer to convince like a bunch of 17 year olds to like, not go to college, especially like not to go to the best, like, you know, I, I don't, I'm not sure that the answers are, are correct,

• 21:52Speaker 01

  but often like his diagnosis of the problem is, is really, is effective and is true. I mean, he's gotten, um, you know, Jeff Bezos, like famously, uh, ripped Thiel once by saying, you know, can think about contrarians is they, you know, they get most things wrong. Um, but Thiel's been right a lot, at least right on the kind of big, on the big things. Often I think the execution is where he's sort of screwed up, um, either financially, like not made as much money as he could have, or just, just done something kind of objectionable or dangerous or something like that.

• 22:25Alex Kantrowitz?

  Yeah, I want to get back to the biography details and then keep going on this thread. So why don't we do that right after the break? We'll be back here on Big Technology Podcast. We've got Max Chafkin. Uh, he is. This episode is brought to you by App Point. Everyone's racing to roll out AI right now. Copilots, chatbots, agents doing real work. But here's the part nobody loves talking about. All that AI runs on your data and most teams have no single way to see it, secure it and prove it's under control. That's exactly what App Point does. For 25 years, they've been the trusted layer beneath the world's most demanding data, now extended across your entire AI estate. Your data, your cloud, and the agents acting on your behalf. It's

• 23:09Alex Kantrowitz?

  how more than 28,000 organizations deploy AI with confidence. So innovation scales without scaling risk. App Point, the unifying trust layer for AI. Head to apppoint.com to see how enterprises deploy AI with confidence. Learn more at avpt.co/bigtechnologypodcast. That's avpt.co/bigtechnologypodcast. Is the author of The Contrarian, Peter Thiel, in Silicon Valley's Pursuit of Power. It's a great book. We'll be back right after this.

• 23:43Alex Kantrowitz?

  And we're back here on the Big Technology Podcast with Max Trachkin. He's talking to us about his Peter Thiel book, The Contrarian. So, you know, we talked a little bit about how Peter Thiel went to PayPal and had this burn down the system type of mentality. But how does he then spread his influence? Because, look, at the end of the day, there's a lot of founders and there's a lot of technologists with kooky views or extreme views or passionate views about different subjects. They don't always build a following. So was it when Thiel then, you know, moved on from PayPal and started a very successful hedge fund and then eventually a venture capital firm, that some of the ideas that he had about society started to take hold?

• 24:28Speaker 01

  Absolutely. And I think he did it on purpose. Like, it wasn't something that just happened by accident. Um, you know, I think Thiel, obviously, he's respected as a very smart investor, as a futurist. I think he has, you know, his moments of rhetorical brilliance, but he's also like a really good marketer. And I think Thiel as kind of an influencer or as a, you know, self-created figure, it's actually probably a helpful way to think about him. Actually, I think, I would argue it's helpful for, I think, a lot of these sort of tech industry figures. But in any case-

• 25:03Alex Kantrowitz?

  As an influencer?

• 25:04Speaker 01

  Yeah.

• 25:05Alex Kantrowitz?

  They're the original influencers.

• 25:06Speaker 01

  Um, but, uh, you know, we could have a whole discussion about Elon Musk. Like, I think Elon Musk is totally underrated as a marketer and like, just, and I'm not to say-

• 25:15Alex Kantrowitz?

  Are you sure? I think people really understand Elon's-

• 25:17Speaker 01

  Well, okay, maybe it's, maybe people are coming around to him now that he can like move the stock price by a, but anyway, um, let me get back on track. I, I think Thiel, um, coming out of PayPal and he made a little bit of money and I think he, he very self-consciously set out to turn himself into this, a figure, a figure of interest and of influence. And at first, and you can kind of see this because his early efforts of it were really bad. Um, he opened a restaurant, it was like a kind of a restaurant nightclub called Friesen.

• 25:49Alex Kantrowitz?

  Sounds kind of fun.

• 25:50Speaker 01

  Yeah. Yeah. I mean-

• 25:52Alex Kantrowitz?

  How much money did he spend to build a thing?

• 25:53Speaker 01

  I don't, it was really, I think there's some detail in the book about like the cost of the sound system and, um, it just sounds-

• 26:01Alex Kantrowitz?

  A million dollars, I think.

• 26:02Speaker 01

  Pretty tacky. Yeah. Yeah. And it wasn't- It wasn't immediately successful as a restaurant. It went out of business. He also started NASCAR magazine, you know, despite, I don't think being, you know, a big sports guy or whatever.

• 26:16Alex Kantrowitz?

  Like opinions about like, basically how, what was men were happy that women were cooking for them in NASCAR anyways.

• 26:24Speaker 01

  It was just like a weird combination of like, sort of, college political magazine, right wing college political magazine with a sports magazine. They hired like these Weekly Standard columnists to write car columns and they, you know, inevitably, you know, wrote kind of like Weekly Standard columns. And of course, you know, people who are race car fans, they might be conservative, but like, they're not picking up a race car to get the like, Peter Thiel view of gender relations or something.

• 26:50Alex Kantrowitz?

  That magazine, by the way, just seemed to me like something that someone would imagine in a laboratory about like, what NASCAR fans would want, without ever having gone to a NASCAR race and never spoken to a NASCAR fan.

• 27:02Speaker 01

  Or what a rich guy who was trying to establish himself as a big time investor, hedge fund guy might do. And because of course, like-

• 27:11Alex Kantrowitz?

  I mean, all of the above.

• 27:12Speaker 01

  Yeah, yeah. Media, of course, media is a great way to, to create influence and, and same thing, like to get invited to cool parties and having a restaurant's a way to get invited to cool parties or have cool parties. And I think he was very explicitly trying to create this, this aura around him as an investor. And that, and it was originally as like a hedge fund guy. And this is kind of one of the funny things to me because like, if you grabbed like a random person on the street, like a random Wall Street Journal reader in 2005, 2006, and said, who is Peter Thiel? And they would say, oh, Peter Thiel, he's one of the most successful hedge fund managers in the world. They would never have said, oh, he's a technologist, anything like that. He was, he was like the next George Soros.

• 27:54Speaker 01

  And he was totally styling himself as that, not as, not as this technologist. And it's only-

• 28:00Alex Kantrowitz?

  Let's define what that is. He was betting large amounts of money on things failing.

• 28:06Speaker 01

  Yeah, on, on, I mean, you know, broadly, yeah, it's betting on, you know, macroeconomic swings. But in, and in the specific case for Thiel, he was, he was betting against the US economy.

• 28:17Alex Kantrowitz?

  And this was a guy who even left, he left PayPal and bet against PayPal.

• 28:21Speaker 01

  Yeah, well, yeah, he wanted to. I actually don't know for sure if he did, you know, how, whether he followed through with the, the investments.

• 28:28Alex Kantrowitz?

  That was the message going out the door.

• 28:30Speaker 01

  Yeah, yes, exactly. And, and he's, you know, I talked to, you know, folks who worked, you know, at his investment firm in those years, and they talked about this very explicit notion that, that Thiel has two portfolios, an optimistic portfolio and a pessimistic portfolio. The optimistic portfolio is the startup investing. It's, it's Facebook, it's, you know, Palantir, whatever. And the pessimistic portfolio is this macroeconomic investing, which was, you know, betting against the US economy, betting that the financial crisis was going to be big and was going to be worse than anyone, you know, expected and kind of betting, betting on an apocalypse. And anyway, he was, he was right about that notion.

• 29:11Speaker 01

  I mean, there's this scene in the book that I think at the time, the people who worked at Clarion thought was insane.

• 29:20Alex Kantrowitz?

  That was his hedge.

• 29:21Speaker 01

  Yeah, which was his hedge fund, where, you know, he and other senior people were talking about, you know, buying a bunch of gold and burying it and, and, you know, just like really just flipping out in a way that felt uncomfortable to some, to some of the people who worked there because, you know, because they didn't think, you know, banks were going to fail. But of course, you know, some banks, you know, did fail and, and, and so it wasn't that, like their, their crazy paranoia wasn't that far off. But then unfortunately, as I said, like the execution did not kind of match the, the insight. They weren't, Thiel was not able to come up with like an investment strategy that, to capitalize on, on this.

• 30:03Alex Kantrowitz?

  No big deal.

• 30:05Speaker 01

  He kind of went the other way. He, he, uh, someone described it to me. It was like they were trying to find a contrarian take to their original contrarian take where like the, you, you're sort of like, you, you think that, that this thing that you've called has now gone to mainstream. So you have to, you know, come up with something even weirder. And it was in that effort that they, that they failed. They ended up, um, trying to time the bottom of the stock market. Um, and as a result, missed, they, they both bought when they should have sold and then they missed the rebound. Um, and, and as a result, his hedge fund completely failed. And, um, you know, he had to basically, it, it, it was reformed as a, you know, family office, like the outside capital, um, uh, it went, went away. Um, and he lost billions of dollars.

• 30:49Speaker 01

  And, and after that, he then kind of restyled himself again, and not as a, um, you know, cool hedge fund manager with a cool restaurant and cool NASCAR magazine, but as the quirky, um, tech guy. And that's when he starts, um, backing seasteading. That's when he kind of goes back to the, um, to his political roots. He starts writing more kind of out there, you know, libertarian political stuff. Uh, he's funding life extension research and that's when the kind of like the Peter Thiel that most tech people would recognize starts to kind of come into focus.

• 31:24Alex Kantrowitz?

  Right. And for listeners, seasteading is, uh, this libertarian idea where you basically build a barge or some sort of island off the coast. And you, you do what you want without the rules of the oppressive, uh, rest of society. Fascinating stuff. Uh, so maybe we should move big technology podcast to some seastead. So we don't have to pay taxes. Just kidding. Um, but anyway, uh, that, so, but he also has this founder's fund where he does, uh, do this startup investing and starts the fellowship. We talked, you talked, so you met him. Um, he was telling you that there's been like three bubbles, right? The financial bubble, some other one, and then the, um, education bubble, which is going to burst. And he basically said, like, if you, uh, end up spending too much money on a house, at least you have a house.

• 32:09Alex Kantrowitz?

  If you spend too much money on education, you got nothing. And he started this thing that, that encouraged young people to take a hundred grand a year from him. And the only condition is they, they drop out of college. Right? So is that like the second half of, uh, of his, uh, what he was doing?

• 32:25Speaker 01

  Absolutely.

• 32:26Alex Kantrowitz?

  Business campaign.

• 32:27Speaker 01

  And I think. And I think it totally was related to something else that was going on in the world at that time, which was the release of The Social Network. And so, you know, The Social Network, you know, Thiel doesn't get very much screen time, but his, he is a sort of an important figure in that, in that story because it was Thiel who sort of set in motion this, this stock structure that creates the conflict between Eduardo Severn and Mark Zuckerberg, which is the, you know, whatever, the basis of The Social Network.

• 33:00Alex Kantrowitz?

  A conflict, yeah.

• 33:01Speaker 01

  And as I, you know, as I understand it-

• 33:02Alex Kantrowitz?

  And he was, yeah, an early investor, one of the earliest investors in Facebook.

• 33:06Speaker 01

  Yeah, as I understand it, he was part, one of the reasons that the Thiel Fellowship came into be was because he was trying to sort of take advantage of, of the moment and also shape the narrative, you know, where, where at the time, you know, Holly, the, the movie, right, The Social Network, does not present a very flattering picture of Mark Zuckerberg. But Zuckerberg, I think, very savvily, and, and Thiel did the same thing, chose to, to like, to sort of flip it and say, actually, this just shows how, how cool we are. And, and there are interviews with Thiel at the time saying, you know, that these producers, these out of touch Hollywood producers, they didn't, they didn't mean

• 33:48Speaker 01

  to, but really, they're just making a great ad for, for entrepreneurship. And, and it's, it's right around this time that he, you know, you know, almost just as a media spectacle, announces, you know, that he's gonna give 20 young people, under $20, $100,000, each 20 under 20. It's, it's totally like a contrived, you know, kind of media thing, partly as a, in an effort to like, you know, catch the sort of wave that's happening of interest from The Social Network, maybe to distract from the fact that like, this kind of Thiel is portrayed in the movie as kind of a schlubby, you know, not, not that interesting suit. And then it takes on this life of its own.

• 34:33Speaker 01

  And, and, you know, of course, it's not just a media event. Real people come and, and real companies are started and, and it, and it becomes this whole, whole thing, but I don't think it was thought all that well through, you know, beyond the just the top line. Here's the media. Here's, here's how we're going to describe it to the press.

• 34:47Alex Kantrowitz?

  Yeah, I think you put it well in the book that when, when he started to convince these young people to drop out of college, all of a sudden, I think that was a huge profile raiser for him. I mean, he goes from being a guy who, and of course he had done this writing and, but he goes from being a guy who had managed a hedge fund and had VC firm to someone who was like trying these radical new ideas to reshape society. And then people started, and they called it the Thiel Fellows. I mean, it was good marketing.

• 35:14Speaker 01

  Yeah. And totally, and it was totally designed to like, to, to, you know, for lack of a better word, like troll the libs, right? Like they, Slate did a, Slate, you know, did like a hit piece on, on the, I'm using the builder language here.

• 35:30Alex Kantrowitz?

  Which they end up, yeah, using in the promotion.

• 35:32Speaker 01

  They used it in their marketing. They loved it, you know? It's like exactly what Peter Thiel wanted was to be, you know, it was to be called out by, you know, some, some lefty journalist. And so I, I think it was totally designed to, to, to catch people's attention and, and it did. And, and I think, I mean, that, that, this is like one of the, one of the big surprises in reporting the book, you know, is just that, you know, not that it doesn't, it doesn't end up going well for all the Thiel Fellows. Like, you know, obviously some of them have gone on to great success, but others, you know, definitely, I think, left the fellowship feeling a little bit used by, by it and feeling like, yeah, this, this worked out great for Peter Thiel. I'm not sure what I got out of it exactly.

• 36:17Alex Kantrowitz?

  Well, maybe they just weren't tough enough. No, I'm kidding. So I want to take a moment here, pause and talk about the man that we just brought up, Mark Zuckerberg, because Thiel and Zuckerberg have an interesting relationship. In fact, when I was reporting always day one. I was told that, you know, Mark has a feedback culture and he likes to listen to contrarian voices. Peter Thiel is a contrarian. That's why he's on the board for this long. I wonder how much Peter Thiel's libertarian burn down institutions mentality has influenced Facebook's direction. I'm thinking about it in particular because the Wall Street Journal this week released these five stories that showed essentially Facebook, you know, blowing

• 36:58Alex Kantrowitz?

  up institutions and failing to, you know, and kind of enforce its own rules. I mean, there are stories about how, how it's, well, making girls feel bad on Instagram, but I think more along the lines of where this came up, letting anti-vaccine sentiment run wild, where the government really would like that not to be the case, allowing cartels and human traffickers to use the system and recruit and publicize what they're doing, and essentially giving a wide range, 5.8 million people of VIP users, right? I mean, how, how could you have 6 million VIP users? I don't get that. But basically exempting them from content moderation and letting them say whatever they want to say. And

• 37:41Alex Kantrowitz?

  I'm reading this and I'm thinking about your book. And I'm like, damn, these are pretty along the lines of what Peter Thiel might want in a society. Essentially, just like in a libertarian world, just let it roam wild and you stay out of the way and society sorts itself out. So I am curious what you think about that. How much influence has he had on Zuckerberg? And, you know, we point a lot to the problems that Facebook has today, but, you know, are they actually kind of like the idea?

• 38:09Speaker 01

  Yeah. There's a line in, there's a line in the Cecilia Carring, Sheryl Frankel book of, I think it's a quote from Kara Swisher about, it basically is like, something to the effect that like, you know, Mark Zuckerberg is like a blank slate that Thiel has, it's like a very extreme statement that I think probably.

• 38:32Speaker 01

  Overstates, you know, the case like Zuckerberg is a very smart person, you know, is obviously independent, independently minded, but I do think, and I do think there's some truth to the, to that sentiment and the sentiment that you're bringing up, which is, I think that Thiel has had, yeah, just an enormous impact on Mark Zuckerberg, both in terms of like how the company is structured, like the literal way that Zuckerberg, you know, got control of Facebook and maintained control of Facebook and then, but also, yeah, this ideological thing, this, this notion that, as you say, institutions are really not that important and that, that it seems like Zuckerberg sort of thinks that Facebook is

• 39:14Speaker 01

  like the only institution that really matters or something like that. But, but you know, for me in those, in those journal stories, like one detail that really stuck out is, you know, that they're getting these reports about, you know, body image, women, young girls like going on Instagram and are, are, are feeling really bad about themselves and really concerning research and Zuckerberg's getting those and then getting asked by Congress, you know, hey, is this making people feel bad? And he's, he's just, you know, totally...

• 39:46Alex Kantrowitz?

  I don't know.

• 39:47Speaker 01

  Yeah. I mean, it's like, like having just a complete lack of respect for the institution. It's, it's, it's really outrageous because it's both a lack of respect for the, for the issue and for, for Facebook's responsibility to society, but also just, you know, maybe people can agree to disagree and maybe Facebook, maybe there are people going to argue Facebook doesn't have a responsibility to stop that, but just the, the unwilling, the, the, the treatment of, you know, whatever our nation's highest, you know, legislative body as just kind of a big joke is, is just kind of crazy. And I think it's completely in line with Thiel's ethos. And I think, I think Facebook is in so many ways, you know, another one

• 40:32Speaker 01

  of these attempts to kind of go beyond the traditional institutions. I mean, we've, there've been lots of stories, lots of stories written about, you know, Facebook kind of seeing itself as its own country. They've got their own Supreme Court now and they're trying to have their own...

• 40:45Alex Kantrowitz?

  Oh, man, Max. When I visited the first time, the conference rooms were all named after countries that Facebook was bigger than. Yeah, you walk in, you're like walking past the Brazil conference room like, oh, why Brazil? They're like, we're bigger.

• 40:56Speaker 01

  It's just, yeah, I mean, it's really, it is really, um, kind of, I'm like, as you say, it's, it's, it's in your face. And, um, and so-

• 41:05Alex Kantrowitz?

  I do wonder, like, when we have Facebook promises, we'll do better, we'll do better, but maybe, I mean, I don't know. I, I do, I know that they're separate from Peter Thiel, but I also know the influence. I'm also just like, maybe they're kind of close to where they want to be. And they tell everybody, you know, everybody else can cry in a river.

• 41:24Speaker 01

  And I also think, you know, there's, there's kind of this, a lot of people have spent time trying to figure out, like, what is Mark Zuckerberg actually? Like, what are his, does he have politics? Is he a liberal? Is he a conservative? You know, he gave some money. Yeah, he's, I think, I agree. I think he's a libertarian and I think, which I think, you know, a hundred percent influenced by Thiel there. But I also think, to some extent, he has no left, right politics. His politics are whatever is going to be required to allow Facebook to grow as big as possible. You know, damn the authorities, damn the rules. And, and I think that, you know, even more so than Thiel's kind of like right wing political views. I think that is more, that is the, that's the kind of core of the influence.

• 42:09Speaker 01

  And, and so, which, and, and in a lot of ways, like, that's a scarier influence because it's, it's harder to talk about or even think about.

• 42:16Alex Kantrowitz?

  Right, and it must be wild in those board meetings to have Thiel, Zuckerberg, Mark Andreessen all together.

• 42:22Speaker 01

  Well, I, I do think it's telling too, you know, the two longest serving board. So Facebook, you know, as you know, I mean, you know, they, they just kind of purged all their board members a couple of years ago. And, and the, but the board members who have survived, of course, are the, are the two libertarians, Mark Zuckerberg and Peter Thiel. And, and I, I think that's, you know, that's no accident. Um, it's, there's certainly some ideological alignment there.

• 42:45Alex Kantrowitz?

  Yeah, uh, let's end this segment talking a little bit about Elon Musk. So I'd love for you to describe the, um, interesting kind of yo-yo relationship between Thiel and Musk. Friends, enemies, friends, enemies. And, uh, you know, I'm just curious, you got Elon to speak to you for the book. Uh, that's not easy to do, especially when it comes to Thiel. How did you sell that?

• 43:09Speaker 01

  I just, I just asked him. Teal was, I mean, Elon was not hesitant to share his views. You know, I have a long history of, you know, whatever. We've talked many times, but I think,

• 43:27Speaker 01

  I think frenemy is the way that I kind of, you know, put it in my mind. I think

• 43:32Alex Kantrowitz?

  Yeah, because Teal did put a pretty big investment in SpaceX.

• 43:36Speaker 01

  A hundred percent. And it's, I think that, I think that Elon and Peter are basically just almost complete opposites, like temperamentally. You know, Musk is this kind of very emotional, all, you know, he, if he's gonna, if he's gonna bet on something, he's going all in. He, you know, wears his heart on his sleeve. He's very, you know, he's very prone to like, you know, getting pissed and then forgiving and then getting pissed again. And, and of course, he's a, you know, he's a gift to the journalistic gods because of that, right? But, and Teal, of course, is introverted. He's cautious. He's constantly hedging his bets. He doesn't ever wanna, you know, wanna go all in on anything. And, you know, he's, and he keeps it all, you know, kind of close to the vest. And so I think there's some temper

• 44:21Speaker 01

  metal thing. But, but as you said, you know, Elon was running PayPal. Peter led a coup that replaced him. And then they were able to patch it up. And I think basically, you

• 44:37Alex Kantrowitz?

  While Elon was on his honeymoon, he got replaced.

• 44:40Speaker 01

  Exactly. Yes. Pretty cold.

• 44:42Alex Kantrowitz?

  Yeah.

• 44:43Speaker 01

  It's, yeah, it's, it's, it's also a testament to like, I mean, it's easy to see, oh, this coup happened. But at the time, you know, Elon was a much more better respected, more famous entrepreneur than Peter Thiel. Elon had already sold a company. He had Mike Moritz, who is the, you know, most respected venture capitalist in Silicon Valley behind him. So

• 45:05Alex Kantrowitz?

  I'm just laughing because there's the story of Musk and Thiel where he bought, so he sold the company and bought this like, what, $1 million McLaren?

• 45:13Speaker 01

  Yeah.

• 45:14Alex Kantrowitz?

  And then

• 45:14Speaker 01

  McLaren F1, I think.

• 45:16Alex Kantrowitz?

  And he crashes it and was like, I didn't buy insurance because I didn't think I was the type of guy that would crash the car. That's an amazing story. Teal was in the car at the time.

• 45:26Speaker 01

  Yeah, and of course, you know, Teal would have, Teal probably had insurance already on.

• 45:31Alex Kantrowitz?

  On Elon's car.

• 45:32Speaker 01

  Yeah. But, uh, but anyway, yeah, and I think that Musk, you know, basically forgave him. Musk kind of said this in not so many words, but he basically concluded like, look, it's not in my interest to, to make an enemy of this guy. And, um, and he was right. I mean PayPal, PayPal succeeded. And they were able to kind of, you know, work closely enough together that when, when Elon really needed money, when SpaceX in 2008 SpaceX was, was failing, it had, it had, um, it had had three launch failures. I can't remember if it was three or two. I think it was three launch failures. And, um, you know, Elon is basically, you know, maxed out his bank account trying to fund Tesla. He has no more money. Teal comes in basically as a white knight and, and, and saves the company.

• 46:17Speaker 01

  And, um, I think does it kind of against his better judgment. Uh, you know, I think does it with some anguish because it was, you know, obviously like if, if Elon had failed, that it would look very bad for, for Founders Fund. Um, and, and as I understand it, you know, there was a lot of back and forth within Founders Fund over that investment where Luke Nosick was pushing really hard to do that investment. Teal wasn't so sure because Teal doesn't, you know, it's, it's not his, um, you know, like taking that kind of risk is, is really not in his makeup, although he did it and, and it, and the rest is history. And as a result, he's got a nice sized chunk of this very, very valuable, um, you know, rocket company. So it's all worked out, but, but they

• 46:59Speaker 01

  definitely have, they're definitely like not, um, not best friends. They're, they're more like allies or something like that.

• 47:06Alex Kantrowitz?

  Yeah. And he did make that investment like, or the investment was announced a couple of days after Elon blew up a rocket. So, but yeah, it's working out well for him. What's your relationship like with Peter Thiel? I mean, one of my favorite scenes in the book was you talked about how you had this off the record conversation with him. And he just kind of finished a sentence and left and you didn't know whether someone was going to take you out or of the room or something and turns out that was just the end of the interview and he never.

• 47:32Speaker 01

  Yeah.

• 47:33Alex Kantrowitz?

  And then you said, oh, he was just kind of done talking. So yeah, elaborate on on this.

• 47:38Speaker 01

  Yeah, I mean, I can't.

• 47:39Alex Kantrowitz?

  What happened in that room?

• 47:40Speaker 01

  I can't share any of the details of what was discussed. I was, I mean, you know, as I, as I, I approached this book as, you know, basically wanted to be to write a journalistic, you know, portrait of of the man. And in other words, to not, not to approach him as some kind of supervillain, which is, you know, has been the treatment sometimes. And but also not to approach him with, you know, with, with de facto deference, to just treat him. There's a lot of the, a lot of the coverage of Thiel, you know, this is kind of a crass way of putting it, but it's like, we're talking about a fellow Davos guy, you know, he's all right. There's this kind of like coziness of some of the articles that have been written

• 48:22Speaker 01

  about him, that I think he's kind of encouraged, where, where, where they're not really calling any of the failures out or really paying attention to, to anything in a, in a kind of critical way. So I wanted to do, but I wanted to be in the middle. And so I was talking to, you know, former employees, basically everyone I could talk to, but also, of course, trying to speak with him and, and to get his perspective because that, you know, I thought that was really important. And yeah, we had this meeting and, you know, it's, it's kind of like the, you know, what you, what you would expect from somebody who's, who's worth billions of dollars and is socially awkward. I mean, he, he, yeah, he just, he just excused himself, but without actually.

• 48:59Alex Kantrowitz?

  Excusing himself.

• 49:00Speaker 01

  Excusing himself. And but, but he was also, you know, very polite. I mean, you know, there was no, you know, a lot of people have asked, did, did, did they threaten you or something like that, you know, because of the Gawker?

• 49:11Alex Kantrowitz?

  Oh, he did bring down a publication.

• 49:12Speaker 01

  Yeah, yeah, exactly.

• 49:13Alex Kantrowitz?

  Yeah, yeah, but go ahead.

• 49:14Speaker 01

  And, and I think that's, I think that's totally worth talking about, you know, in, in terms of, to the extent that, that there was intimidation, the only, the intimidation just came from the fact that he had done this thing. But, but in terms of the actual in-person interaction and interactions with his like PR people and stuff, they, they were not, yeah, there was, there wasn't a hint of menace.

• 49:38Alex Kantrowitz?

  Right. He didn't send Charles Harder at you after you sent him the questions for the fact check?

• 49:43Speaker 01

  They did not send Charles Harder after me. Charles Harder is not a big part of the book, though, so.

• 49:48Alex Kantrowitz?

  Yeah.

• 49:50Alex Kantrowitz?

  Well, he's the guy, wasn't he the guy who the lawyer who he funded?

• 49:52Speaker 01

  Yeah.

• 49:53Alex Kantrowitz?

  So he could take on Gawker?

• 49:55Speaker 01

  Yeah, Harder is, Harder was the lawyer prosecuted the Gawker case. And I think, you know, one thing-

• 50:01Alex Kantrowitz?

  With Teal's money.

• 50:02Speaker 01

  Yeah, with, with Teal's money and in secret. And, you know, and, and, and, you know, basically architected the destruction of this, of this media platform. That was really big and really influential and, and also did, you know, of course, wrote a lot of like really tawdry stuff, including, you know, the post that, that, that got Teal mad, which, you know, said that he was gay. But, uh, but Gawker also did a lot of important journalism as well. And, and so, you know, it, it definitely, I think, I think that case definitely created an environment where it was harder for people, harder for journalists to, to really think critically or write critically or talk to sources about Peter Teal. It hangs over every conversation you have, every conversation

• 50:47Speaker 01

  with an editor, every conversation you have with a source.

• 50:50Alex Kantrowitz?

  Yeah, as intended. What's your release? Oh, I asked that. This was the question I wanted to ask you. Do you like him?

• 50:59Speaker 01

  I'm, um, trying not to, I, I don't really wanna, I don't know. It's kind of like, it feels important to me to not like pass judgment or anything like that.

• 51:10Alex Kantrowitz?

  Yeah, but you, you must, you must have some, I mean, I know, well, anyway, you try not to pass judgment, but you must have some personal feeling about it. Here's this 330-page book about the guy.

• 51:20Speaker 01

  Yeah, you're right. You're right to press me. Okay. Um, I feel, um, I feel like he's worthy of respect. And I think there are aspects of his achievements and, and the things that he's done that are worthy of admiration. And, and I find- You know, I find him to be like a really interesting and charismatic figure, but I also think that he's, he's pretty dangerous. And I think that the ideology that he has espoused and that he has pushed in all sorts of ways is bad. And it, and it's, and, and it, and it needs to be scrutinized and, and understood.

• 52:03Speaker 01

  And to the extent that it's, it's filtering into these companies that are incredibly, incredibly powerful, that have, you know, unbelievable control of our lives, access to our data. I think we need to, I think we need to talk about that. And I also think, you know, especially as he gets, as he gets into funding these, you know, funding these political campaigns, putting $10 million into this guy Blake Masters, running for senate in Arizona, $10 million into J D Vance, both of them either former or current, you know, Thiel employees, that, you know, I think that those ideological questions become, you know, even more important. I mean, for me, the thing that is most troubling and that I think is worth a lot of conversation is just the, the relationship to democracy.

• 52:48Speaker 01

  This idea that democracy, you talked about indifference to institutions, which I think is, is definitely.

• 52:53Alex Kantrowitz?

  Yeah. If you're about to get, I, I think that you're about to get into some of the Trump stuff.

• 52:58Speaker 01

  Okay, okay.

• 52:59Alex Kantrowitz?

  I, I really want to do that. And it's a great place to pause here, go to break and then pick up the Trump story. So why don't we do that? We'll be back here on the Big Technology Podcast right after this with Max Chafkin. He's the author of The Contrarian: Peter Thiel and Silicon Valley's Pursuit of Power. While we go to commercial, you can go to your favorite bookstore and pick it up.

• 53:21Speaker 02

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• 53:52Alex Kantrowitz?

  And we're back here on the Big Technology Podcast with Max Chafkin, Features Editor at Bloomberg Businessweek and also the author of The Contrarian, which is the book we've been talking about. It's all about Peter Thiel, a little biography of sorts, but you know, getting a little bit more into the philosophical stuff. And I definitely want to talk about sort of the big Peter Thiel story where he gets to take his ideology to the world, the one that you said was bad ahead of the break. I think this is where you were going with it.

• 54:20Speaker 01

  Yeah.

• 54:20Alex Kantrowitz?

  Where it extends to his support of Donald Trump. And then I would say more importantly, his, the way that he actually influenced the staffing of his administration. So is that where you were going earlier, Max?

• 54:35Speaker 01

  Yeah, I mean, I think, so as you said, Thiel, you know, famously or infamously, depending on your politics, you know, made a big donation to the Trump campaign just before, just before the 2016 election and also gave this speech at the Republican National Convention endorsing Trump. And that gets him on the transition committee. And as a result, you know, gives him access to the Trump administration. And he is given an opportunity by Steve Bannon, who was his, you know, his ally, you know, his main ally in the administration, at least until Bannon was.

• 55:11Alex Kantrowitz?

  Ousted.

• 55:12Speaker 01

  Ousted. Given the job of appointing basically people who can, you know, disrupt, as Bannon put it to me, kind of disrupt the administrative state, who can, who can help, you know, do the, execute the Trump revolution on government. And, and so he has a chance to.

• 55:31Alex Kantrowitz?

  Right.

• 55:31Speaker 01

  Appoint all of these.

• 55:32Alex Kantrowitz?

  To pause. Yeah, he talked about, you talk about them in the book, how the view was Republicans can win elections, Democrats can win elections, as long as Democrats who believe in bigger government can staff these government agencies, the Democrats are essentially never out of power. And what they wanted to do is. Strip the agencies or, you know, I guess they call it the swamp or I don't know of their power and of their people so that they wouldn't have this Democrat influence. It's kind of questionable as to whether that's actually true about about their thesis, but it is interesting because when Trump came into power, it was kind of weird to see him put people in charge of every agency to do kind of exactly the opposite of what the agency

• 56:16Alex Kantrowitz?

  was tasked to do. And it was one of the most weirdest puzzling thing where like EPA guy wanted to demolish, you know, all environmental protection and financial people wanted to demolish the financial protections and, you know, the list goes on. And now, actually, after reading this, turns out that this is sort of the influence of Thiel on the Transition Committee, getting these people in line, even if he was like moderately successful, definitely the philosophy is.

• 56:40Speaker 01

  Well, and the thing that the really, the mind blowing thing for me is that, you know, Thiel actually wanted to go a lot further. I mean, Bannon was basically like, told me basically, you know, Thiel, Thiel's further out than Trump. I mean, Thiel was too far out. If you, if you thought we were doing crazy things, like you should have seen this stuff that Peter actually wanted to do. And, you know, that's, you know, Thiel attempted to get Balaji Srinivasan made FDA commissioner. Balaji Srinivasan, you know, a very opinionated, very outspoken, very hostile to the press.

• 57:13Alex Kantrowitz?

  Yeah, he wanted to make the medical, the medical approval process for medicines, a big crowdsourced spreadsheet where people rate their experiences with the drug. And it's like, well, you could sort of learn from there.

• 57:27Speaker 01

  Yeah, that was the idea. Replace the FDA with Yelp, which of course, which actually I think is something that Thiel actually wants, or some version of that. They, they're in favor of, you know, drastic deregulation of, of, of drugs and make no secret about that. But it's just kind of the idea of having somebody with like no government experience who wants to get rid of the FDA, run the FDA, and who's also just been totally intemperate on Twitter is just kind of crazy and it wasn't going to work. Thiel also had the opportunity to suggest all these chief candidates for chief scientists, the, the top scientific advisor to the, to the president and, and his two main choices were climate change

• 58:11Speaker 01

  deniers, who, who, you know, one of whom, William Happer.

• 58:18Speaker 01

  You know, he's actually, he's a very respected physicist at Princeton, but who has kind of has a sideline in arguing that CO2 gets a bad rap and it's actually good because it's tree food. And I mean, it's very like, pretty fringe, pretty fringe stuff. And, and Thiel wanted him to, you know, have a major scientific position. The other, his other candidate was this guy, David Galertner, who is a Yale computer scientist, but who also kind of as a sideline is, is a, is a big time provocateur, has written another, you know, kind of, you know, far right, you know, a book about, about, you know, how universities are too left. He's basically, you know, a, yeah, like a provocateur. And so another

• 58:59Speaker 01

  guy who really had little chance to succeed. And, and so Thiel didn't do that well in terms of actually getting people into government. Although I think, I would argue that he did have, he did have some influence on the Trump administration and he kind of made the most of, of his, of his time there, even if he wasn't able to get any of these kind of far out picks into, into government. Because he was able to get, you know, access, you know, he, he set up this, this meeting, this big meeting with all the tech CEOs, gets Alex Karp, CEO of Palantir, in a room with Donald Trump, which I think was very important for, for Palantir and, and has helped, is one of the reasons Palantir has been so successful over the past four years.

• 59:38Alex Kantrowitz?

  Yeah. One of the interesting things to me was, you wrote about how they, in the, in the transition team, anticipated that Thiel was just kind of there for the photo op, but he never asked to meet Trump. And it's all about filling the government with people who had his ideological beliefs.

• 59:56Speaker 01

  There is this kind of like, talking to, to DC people about Thiel, you know, they kind of often talk about him as this kind of cipher, because he doesn't behave in, in the normal ways. He, and I think some of this may have to do with kind of inexperience. Like, and I think part of, if he had been a more experienced political operator, he probably could have, maybe he could have gotten Bellagio, you know, made FDA chairman or something. But I think also some of it is that his, that he's not playing the same game that, that many of the others are playing. And, and I don't think, I don't think his game was The like, let me, you know, have as much influence over the Trump administration as possible. It was, let me set things up so that my companies have as good a chance

• 1:00:40Speaker 01

  as possible and that, that long-term, he has political influence, which is exactly what happened. And, you know, post-Trump, post, you know, January 6th insurrection, you know, Thiel, I think, has, you know, in a strange way, maybe more influence than he had, you know, even during the Trump administration.

• 1:01:00Alex Kantrowitz?

  Why is that?

• 1:01:01Speaker 01

  It's kind of, well, because he's kind of, he's been able to put himself in the middle of this, you know, the post-Trump movement. I mean, these, these candidates that he's funding, I mentioned, Masters and Vance, you know, they are like, kind of among the sort of standard bearers for, you know, what I think probably should be described as like Trumpism, or, you know, nationalist populism, or whatever. It's, it's the, it's Trumpism with or without Trump. And, and I think that Josh Hawley is another, is another one of these figures, also a figure, a former Stanford Review guy, who has taken money from, from Thiel, who has endorsed JD Vance. There's kind of a little crew.

• 1:01:39Alex Kantrowitz?

  It's gonna be interesting to see if Trumpism without Trump is actually gonna work. It may, it's, it, there's, I don't know, I think there's a chance that it was unique to the individual. Like Josh Hawley is just too polished. I think that you talked about, like, how it was like, you know, Trump was the inheritor of the Paul brothers, how Ron Paul and his son Rand, and like, what they realized, or, you know, someone in their, in their, realized was, it wasn't necessarily the ideology, it was just they wanted the craziest person in the room.

• 1:02:07Speaker 01

  Yeah, 100%. And I think that's...

• 1:02:10Alex Kantrowitz?

  It's really tough to be the inheritor of that philosophy, even though if you say the same things on, on policy. It's the fact that the dude could go and trash Rosie O'Donnell at a debate that was part of his appeal. Sorry, go ahead.

• 1:02:22Speaker 01

  But, no, no, but I, I do think that is, Peter Thiel is attempting to be the inheritor of that movement, and to be, to be the patron of that movement, to be the person who is behind the scenes for the 20 to 30% of the country that wants the guy who says the craziest shit in the room.

• 1:02:40Alex Kantrowitz?

  Right.

• 1:02:40Speaker 01

  And, which, by the way, that formulation is from this Reason magazine writer, Brian Butler, who wrote a really great book about, about Ron Paul. And, and, and this, there was this feeling among the libertarians. I think some libertarians feel, you know, a little bit betrayed by the, by, by Thiel, because Thiel was... You know, Thiel kind of presented himself as a libertarian, but then, but has kind of gone all in for Trumpism, which is obviously very different from libertarianism. Um, but anyway, just to get back to the thing about, you know, what, what exactly is bad? I mean, I think the thing that's bad is as they've been attempting, as Thiel and his acolytes have been attempting to kind of harness this energy, they're positioning themselves

• 1:03:24Speaker 01

  as sort of being okay with the January 6th insurrection. You know, Josh Hawley famously, you know, raised his fist in solidarity as he walked into the Capitol, you know, on January 6th. And we're seeing, you know, J D Vance and Masters to some extent, you know, kind of trying to thread the needle and be kind of be okay or create a, create a space where the, the people who stormed the Capitol are just, um, just protesters and the, the police that tried to stop them are, you know, somehow, um, you know, strong arming, you know, civil disobedience or something like that. And, and that to me is, is very dangerous. And it's, it's, uh, at least if, if you believe in democracy, it's dangerous because it's,

• 1:04:08Speaker 01

  it's, it's totally hostile to, to kind of this core part of, of American government.

• 1:04:13Alex Kantrowitz?

  Right. And all throughout Thiel's life, he's talked about how, uh, you know, quote that you see often in the book is voting is overrated. I don't really believe in voting.

• 1:04:21Speaker 01

  Yeah. And, and, and he's said in all sorts of ways, there was this famous essay in the, um, that was published by the Cato Institute where he, uh, talked about, basically he decided that democracy was incompatible with libertarian beliefs, his beliefs. Um, and he's, you know, been a patron to this guy Curtis Yarvin, who is, uh, you know, uh, better known as a mold bug, but, um, but you know, this blogger who is, uh, whose big idea basically is, is dictatorship. I mean, he's a, he's advocating, you know, some, some version of, of fascism and, and you're seeing this kind of spill into, you know, borderline mainstream Republican discourse, people talking about an American Caesar.

• 1:05:06Speaker 01

  And I think that is, I think you can draw a line from that idea to Thiel. And, and I think that is, I mean, that is a very, very radical position.

• 1:05:15Alex Kantrowitz?

  Yeah, um, one question I have for you. So Teal, who we've spoken about is gay. I, you know, obviously, like, um, you know, the political beliefs across the spectrum, if you're gay. But I, one of the things I'm struggling to see is how he was able to align himself with people who were so militantly anti-gay. I'm curious what you think. I mean, here's one example that you write about in the book. Uh, let's see, about Ron Paul. Paul's supporter preferred the old Ron Paul, the Ron Paul who talked like the one of, one of Teal's old Stanford Review columnist, who published a newsletter talking about Paul, that said 95% of black men in Washington DC were criminals and said, "I missed the

• 1:05:59Alex Kantrowitz?

  closet about gay rights." Like, Teal, they wanted to stick it to the cathedral. He was ready to help them.

• 1:06:06Speaker 01

  Yeah. And if you go back to Teal's, um, you know, to the newspaper, Stanford Review, or the, or the, or the book he wrote, Diversity Myth, um, you will find some views on, um, uh, you know, sexuality that are, are really, you know, pretty backwards. Um, uh, and they're, you know, it's, it's, uh, and, and there, there's, there's, obviously, there's a temptation to psychologize this. And, and, and, and, you know, a couple, some people have suggested to me, um, that, you know, it's, it's self-hatred or something like that, you know, Teal's a Christian and, you know, maybe, maybe there's some, some of this is like a symptom of his own, you know, discomfort with himself. I tend to think he is a provocateur. And

• 1:06:49Speaker 01

  I think that there's, it's always been profitable, um, especially in right-wing circles, to be in, in an out-group and to kind of crap on the other members of your out-group. Like, that's, that's kind of, there's like a tried and true path, um, in, in conservative activist, activist politics of, of doing exactly that. And I think, so I don't, like, I don't think it's that complicated. I think it's just, it's as simple as that. And I also think, probably... He just doesn't feel, you know, he's, he's, he's talked about this a little bit. Like, I think the speech that he gave at the Republican National Convention, which, of course, was, he was criticized a lot by, you know, gay rights groups because the Republican Party had all, had positions on trans rights and gay rights that were really, you know,

• 1:07:34Speaker 01

  I mean, they, you know, they were, they were against those things. And, and, and I think Teal, as he kind of said in that speech, like, he doesn't want to be defined by his, his sexuality. And, and he doesn't want, he, he, he feels so strongly about that, to such an extent, that, you know, he's willing to, you know, ally himself with somebody who is, you know, is part of a party that's anti-gay. I also think it's probably, like, I think Teal has talked about this, but Trump probably was like, less hostile on gay rights than

• 1:08:04Alex Kantrowitz?

  Yeah, I don't see Trump as, as hostile.

• 1:08:07Speaker 01

  Yeah, yeah. So I think there is some way to see it as

• 1:08:10Alex Kantrowitz?

  Trump is like, I mean, Trump, sorry, I'm probably getting trouble saying this, but, you know, Trump obviously said what he said about, in Charlottesville, and I'm not absolving of that. But also, like, guy grew up as a New Yorker.

• 1:08:22Speaker 01

  In real estate, yeah.

• 1:08:23Alex Kantrowitz?

  Ted Cruz accused him of having New York values.

• 1:08:25Speaker 01

  Yeah.

• 1:08:26Alex Kantrowitz?

  His daughter converted to Orthodox Judaism. So, you know, do I think he's backwards on race in a lot of ways? Yeah. Do, I don't know, I don't, I guess, like, his, his positions are a little more complicated.

• 1:08:38Speaker 01

  Yeah, and I think there was, like, from, from Trump, like, to the extent that, that Trump was, like, anti-gay, it always seemed a little bit half-hearted or something. And not, and, and I do think there's a way to see, you know, Teal's speech as an important moment, you know?

• 1:08:55Alex Kantrowitz?

  First time, right?

• 1:08:56Speaker 01

  Yeah.

• 1:08:57Alex Kantrowitz?

  Someone who was openly gay spoke at the Republican National Convention.

• 1:09:00Speaker 01

  First time they acknowledged it on stage. Because there actually had been one other, there had been another instance, but, but that, that person was booed during the, you know, during the, during the speech. And Teal not only wasn't booed, but he, he got a standing ovation. And like, it was, when you watch it, you know, I do think, it does feel like a moment. It feels like, wow, the, the, the, the beating heart of the Republican Party, they're not just accepting this, they are cheering for it, they're excited about it. So I, I do think that is, that's something that probably, like, on a historical basis, that will be an important historical thing that, that Teal was a part of.

• 1:09:36Alex Kantrowitz?

  So wrapping up this chapter about politics and government, he did get some, so why did he back Trump, right? That's a question that a lot of people ask. I think that like, there's an idea that Trump and Bannon did embody a lot of the values that he wanted, but there was also the business rationale, which was that he had three and a half billion dollars sitting in an IRA that he didn't want taxed, Roth IRA. And he, he wanted his businesses, Palantir in particular, to be able to get government contracts and thought that getting close to power would be a good idea. And he essentially made this one billion dollar bet right after the Access Hollywood tape came out. That was like, alright, maybe Trump will be able to help me solve these problems. Let's see what happens. So how did that work out for him?

• 1:10:19Speaker 01

  Yeah, well, I think it's important with Thiel to see that the business and politics are always connected, that he doesn't, that he has these, he, he has a sort of political project and a business project and they work together in tandem. And you can't, his ideology is in service of his business, his business is in service of his ideology, they're hard to separate. Kind of like, I think the Koch brothers, there's some of that with the Kochs too, where they're really good at combining, at finding an ideology that like sort of works with their business imperatives and, and then finding business imperatives that work with their ideology. But I think with Thiel, it's, it's two things. It's one, he was buying low, he, he had an opportunity to have a huge stake in, in this

• 1:11:03Speaker 01

  new administration that had very few kind of institute, there, there was very little institutional support for Trump. There were no, it's not only that there was little institutional support, there were no like respectable business people who were backing Trump. It was all kind of, I mean, there were a few, but it was like largely, you know, if you go to the, who else was speaking at the Republican National Convention? It's like real estate, kind of shady seeming real estate guys.

• 1:11:25Alex Kantrowitz?

  Hello, salespeople.

• 1:11:27Speaker 01

  Yeah, some reality TV stars like the guy who runs the cage fighting company was there, you know, Chachi from Happy Days.

• 1:11:34Alex Kantrowitz?

  Yeah, Hulk Hogan spoke there also, right?

• 1:11:36Speaker 01

  I don't know if he actually, did he appear on stage? I can't remember.

• 1:11:39Alex Kantrowitz?

  He showed up, right?

• 1:11:40Speaker 01

  Yeah, he was, I mean, he's, you know, one of the biggest celebrities in Tampa. So, um, so that would make sense. But, uh, but anyway, but I also think that, and, and there was so much effort among, um, tech people, and I'm sure in private especially, to kind of like explain away Teal's support of Trump as just, as just being about, as just being kind of a Machiavellian bet. He doesn't, couldn't possibly really want Trumpism. And I think the truth is, he does like Trump. I think there's a lot of, there's a lot about Trump's ideology that is very closely aligned with Teal's despite the differences that I brought up earlier.

• 1:12:13Alex Kantrowitz?

  Yeah.

• 1:12:14Speaker 01

  The core of Trump, yeah, well, the core of Trump's appeal is being able to say, being able to get away with saying the racist thing or the sexist thing.

• 1:12:24Alex Kantrowitz?

  Well, I think you even note that like, one of the things he enjoyed the most when in the watch party for the election was how angry people in Silicon Valley would be about Trump's election. Okay, but, but what about the money though? The, um, the, the deals for his companies? Did he, did he make out okay from, from those?

• 1:12:41Speaker 01

  Yeah, I mean, he did great. And I think some of it, it's, of course, it's always hard to, it's always, it's always hard to untangle, okay, like, why did Palantir get those contracts? Did Palantir, Palantir got a, an $800 million Army contract, another $400 million contract. Um, and he took over this Project Maven from Google. That's another 40 million bucks a year. You know, it goes on and on. Um, and of course, it's, it's very hard to untangle, you know, why does a company get these deals? Um, because of course they are, you know, they're, they're, their explanation is, well, we were getting the deals because we have the best product and we've spent a long time, um, selling it. But of course, when you're talking about defense contracts, I, I think inevitably like politics plays a role.

• 1:13:24Speaker 01

  And, um, and I think it's, it's no accident that, that Palantir took off during the Trump administration, that, that it, that really had these, a series of breakthroughs, you know, you know, under an administration where Teal had influence. I also, um, I also think, you know, you brought up his, his, his tax status and, and this, We could probably have a really long conversation about this, but Teal has been pursuing his whole career, this very, very, very aggressive strategy to pay, it's legal, but, but just exceedingly aggressive strategy to pay almost nothing in taxes on his, on most of his income, it's his, his investment income, because it's all in a Roth IRA retirement

• 1:14:06Speaker 01

  account. And there's been this feeling in, in, in Teal's world that at any moment, somebody could come along and take that away from him, either because there is a reinterpretation of the rules, or someone changes the rules, which is something that was threatened during the Obama administration, but, but didn't actually happen. Or there's, you know, or, or somebody finds, you know, he, if he, if he accidentally got something wrong in his taxes, then, then it could all go away. And I think a lot of Teal's sort of operations over the past decade or so can be explained by that. I mean, the, the, the acquisition of, of citizenship in New Zealand, which we haven't touched on, but he, he, he secretly acquired citizenship in-

• 1:14:50Alex Kantrowitz?

  You know, Max, you are right. This is such a fascinating story, because there's, I mean, each one of these could be their own show, but sorry, go ahead.

• 1:14:56Speaker 01

  Anyway, I, I think that it was widely interpreted, and, and I think this even led to some jokes in Silicon Valley, that this is just him being, you know, apocalyptic, he wants a doomsday bunker. But I think the truth is, he, he actually wanted a doomsday tax shelter, you know, just in case Obama goes to, because he saw Obama as a communist, you know, case Obama, you know, goes full commie or something and tries to come for his money, Teal is going to have a backup plan. And that, and that backup plan is, at the time, a conservative government that was running New Zealand at the time, and would, would be a way to create some leverage in a negotiation with the IRS, or, you know, worst case scenario, right? There have been these billionaires, or, or, or centimillionaires

• 1:15:38Speaker 01

  or whatever, who have renounced their US citizenship in order to, to get out of a tax bill. So, so that would be, that would be another option. And I think similarly- You know, Thiel's engagement in politics and his support of Trump, some of it has to do with, you know, wanting to make sure that the tax, the tax policy favors him. And, you know, this sounds, if, from a certain point of view, this sounds outrageous, but of course, a lot of this is happening out in the open. I mean, we're seeing, you know, Keith Raboy and a bunch of these guys who have, you know, relocated to Miami, you know, they're, they're doing it, you know, as they say, to, because they don't want to pay state capital gains tax in California. And, and you're also, you also hear that, you know, kind of another threat of Thielism,

• 1:16:20Speaker 01

  but this idea of exit, this idea that you should be allowed to, you know, withdraw from the government, either by going to a seastead, as you said, or, or by, you know, decamping for your New Zealand bunker. So I think a lot of the political motivation, some of the political motivation for Trump came from that, that sense of, of vulnerability and a desire to like, make sure that, that the tax policy stayed friendly to the interests of tech billionaires.

• 1:16:46Alex Kantrowitz?

  Right. So Thiel's out of office, I mean, it's not Thiel, Trump is out of office, Freddie and Slip. You know, Thiel's got his money, is, what's his next act?

• 1:16:56Speaker 01

  I mean, I think his next act, as I said, is continued influence in this, in this right wing movement, which, it's true, you might be right, that like, maybe we will close the book on this and we'll get like, kind of a, a more conventional Republican nominee, and then I think, then I think that'll really sideline Peter Thiel.

• 1:17:16Alex Kantrowitz?

  I personally think that, that it'll be the return of Trump or one of his kids.

• 1:17:20Speaker 01

  Yeah.

• 1:17:21Alex Kantrowitz?

  It would be astonishing to me if none of them ran next, next cycle. It would be astonishing.

• 1:17:26Speaker 01

  Yeah. So I think his, I think his play is to, to have influence in that, in that world and to continue to, to be a, you know, political kingmaker, to be, you know, to play that kind of Koch Brothers type role, but in the, you know, the Koch Brothers played that role in the kind of conventional mainstream Republican Party, but to play that role in the, in the, you know, Trumpist party, whatever it's called, the Freedom Party or the Patriot Party, whatever. And I think that's part of it. And I think also, and I think, you know, continuing to, to, to make investments, to, to, to do the investor thing and, you know, there's, he's been. You know, he's been doing a bunch of stuff in crypto. It's sort of hard to figure out what he actually believes with crypto because, you

• 1:18:11Speaker 01

  know, he's, he's sort of like making investments, but then he's like crapping on Bitcoin. But so I, I think there's going to be, you know, continued engagement in, in technology and also, and also a real push politically.

• 1:18:27Speaker 01

  I also think, you know, he has two kids now and I, I do think it's possible that, you know, he's slowing down or, or something like that, like we'll see. And, and I think, as you say, some, some of it may come down to, you know, what happens politically, whether, whether it's an advantageous situation for him or not. But I, and this is a guy who really seems to get a kick out of being provocative. So it's hard for me seeing him not trying to find some new way to provoke. And when you have $10 billion or however much money he has, um, you know, you can, that, that could, that could be pretty dramatic, uh, depending on what he does.

• 1:19:05Alex Kantrowitz?

  Do you think he'll talk to you again after the book?

• 1:19:09Speaker 01

  I don't know.

• 1:19:12Speaker 01

  I'm open to it.

• 1:19:13Alex Kantrowitz?

  Yeah.

• 1:19:15Speaker 01

  I hope so.

• 1:19:16Alex Kantrowitz?

  Uh, book was great, man. Uh, I didn't think I was going to get through it this week, uh, and I couldn't stop reading it. So I think that, uh,

• 1:19:24Speaker 01

  Oh, well, thank you, Alex. I really appreciate it.

• 1:19:26Alex Kantrowitz?

  Difficult subject matter, like we spoke about, and it's, uh, it's well-rounded. It's good. It's engaging, well-written, packed with facts and definitely enlightened me to a lot of stuff that I hadn't known previously about Silicon Valley and power and tech. And, uh, I suggest everybody go read it. Thank you, Max, for joining the show. Appreciate it.

• 1:19:47Speaker 01

  Thanks, Alex. This is really fun.

• 1:19:49Alex Kantrowitz?

  Super fun. The book is The Contrarian: Peter Thiel and Silicon Valley's Pursuit of Power. It's available in all bookstores. You can grab it today, sometime later this week. You know, help Max become a bestseller. All right. Well, that will do it for us here on the Big Technology Podcast. Thanks to Nick Guatney for editing this and mastering the audio. Thanks to Red Circle for hosting and selling the ads and thanks, most importantly, to you all, listeners. Show be nothing without you. Appreciate you coming back week after week and we will see you again next Wednesday.

• 1:20:30Speaker 02

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