Donald Trump, Peter Thiel, Charles Koch
Donald Trump, Peter Thiel, and Charles Koch. Photo credit: Adapted by WhoWhatWhy from U.S. Department of State / Flickr , Heisenberg Media / Flickr (CC BY 2.0), Gavin Peters / Wikimedia (CC BY-SA 3.0), and Patrick Pascal Schauß / Pixabay .

The Koch family is aging out. Peter Thiel has picked up the mantle as the new Midas of the extreme right.

For almost 50 years, the Koch brothers have been the bête noir of the left. Their influence over conservative politics and policies has been significant, even if not to the levels they are given credit for by their opponents. But the Koch family, as a political brand, are aging out. One brother is gone, and the other seems more interested in philanthropy than in Trumpism.  But there is a new kid on that block to fill the void: tech billionaire Peter Thiel

In this week’s WhoWhatWhy podcast, we talk with Bloomberg editor, reporter, and Thiel biographer Max Chafkin. He explains that from Thiel’s time at Stanford, as the creator of an early alt-right publication, to his mentoring of Mark Zuckerberg in the techniques of disruption and libertarianism, to his support for Donald Trump, he has been setting the stage for his own rise as a political Midas.

One of the first Silicon Valley executives to support Trump, he was the leader, years ago, of what has been called the PayPal Mafia: a group of his Silicon Valley disciples who have tentacles into everything from MAGA to Facebook, from Tesla to LinkedIn to dozens of other technology companies. 

Chafkin draws a Venn diagram in which Thiel is linked with vast wealth, Silicon Valley power brokers, and a growing right-wing ecosystem.

According to Chafkin, Thiel found Trump appealing not only for his political views, but also because his anti-establishment attitude was right in line with how Thiel sees the world. 

The man who took down Gawker and drove both the publication and its owner into bankruptcy is picking up where the Kochs left off.  Except that Thiel is even further to the right — and a lot meaner in how he does it. 

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Full Text Transcript:

(As a service to our readers, we provide transcripts with our podcasts. We try to ensure that these transcripts do not include errors. However, due to a constraint of resources, we are not always able to proofread them as closely as we would like and hope that you will excuse any errors that slipped through.)

Jeff Schechtman: Welcome to the WhoWhatWhy podcast. I’m your host, Jeff Schechtman. When most of you think about who have been the key players in financing the rise of the right in America, the Koch brothers in their efforts to buoy the right and push all sorts of buttons on the left are front and center. But the fact is that the Koch brothers are aging out. One is gone, the other seems to be unsure of where he currently stands. The Koch family in many ways represented an old-school view of the world, just as their money was from an old industrial model economy, things like paper, plastic, pipelines, and textiles.

So as the Kochs fade away, who will carry the mantle? Who will represent funding for the modern right in the postindustrial economy? More and more the answer to this seems to be Peter Thiel. A legend in Silicon Valley, the man who took down Gawker, and one of the Valley’s most important venture capitalists, with tentacles into everything from MAGA to Facebook to the military-industrial complex. Peter Thiel is already shaping elections in 2022 and 2024, even as he continues to move forward in Silicon Valley. But who is Peter Thiel, and why should we care?

The answer lies in the pages of a new book by my guest Max Chafkin entitled The Contrarian. Max Chafkin is a features editor and tech reporter at Bloomberg Businessweek. His work has appeared in Fast Company, Vanity Fair, and The New York Times, and it is my pleasure to welcome Max Chafkin here to the WhoWhatWhy podcast to talk about Peter Thiel, and his new book about Peter Thiel, The Contrarian. Max Chafkin, thanks so much for joining us.

Max Chafkin: Yes, thanks. Thanks for that intro, Jeff.

Jeff: Certainly, Silicon Valley is filled with iconoclasts, a lot of strange people that we’ve watched come and go over the years. Why is Peter Thiel different? Why should we care?

Max: Well, I think the framing that you just set up, the comparison with the Koch brothers, is a really smart one. Thiel has had this incredible impact on Silicon Valley. If you look around and say how did Silicon Valley go from being an economic sideshow, a curiosity, something that people were interested in, to being the economic focal point for the world? Where the world’s largest and most powerful companies are located. Where the global culture, to an increasing extent, is being created. Where even politically there’s an increasing amount of engagement. I think you would say Peter Thiel is one of those guys, along with a very small handful.

What’s really interesting about Thiel, who co-founded the company PayPal, he co-founded Palantir, this surveillance company and military contractor, and was an early investor in Facebook, is that he also created what I think of as the dominant Silicon Valley ideology, and that is the ideology of disruption. It’s what says companies, tech companies in particular, tech billionaires, are this privileged class of people that in order to make the future happen should be trying to grow as quickly as they possibly can, scaling their companies with no regard for the consequences, and should be willing to break the rules.

That breaking the rules, “disrupting the status quo,” isn’t just something that happens by accident that you’re allowed to get away with. It’s something that you actually should do. And so all of those things make him a really interesting figure in the world of tech. But as you said in the intro, he’s not just playing in tech. What he’s doing is trying to create this new political movement and to play kind of a patron role to the far right; the Trump movement as it were. So he was in 2016 one of the first executive types to come out and support Donald Trump, he was a major donor to Trump, and post-2020 has really emerged as one of the key financial backers of far-right candidates.

Jeff: To your point about disruption and move fast and break things, and we’ll come back to that and talk about Thiel and Zuckerberg, it’s interesting in reading your book that PayPal at the time — and we forget about this — was viewed, at least Thiel viewed it, as something akin to the way we view crypto today.

Max: Yes, absolutely. And PayPal in so many ways had this huge influence that’s partly a credit to Thiel’s personality and the force of his ideas, but also to just the impact of this company. So, when Thiel was promoting PayPal in the late 1990s, he was talking about it not just as, “Oh, this is going to be a way for you to buy stuff on the internet,” which is of course what it is and how people understand it, but this idea of having digital money as a way to free people to get out under the thumb of government. Thiel talked about that this would help destabilize nation-states. That it would be the equivalent of a Swiss bank account in your pocket.

It’s like libertarian sort of philosophy that I think now people are really used to hearing about crypto. But it actually began during those PayPal years, and the company never really got there but those ideas were influential. And they continued and Thiel continued to develop them. And the idea is basically just that rich people should have a way to shield their assets and to shield their lives from the regulations as they see it can help overly aggressive regulations of the US government. Which obviously can take you to some very out-there places when you take it to its logical extreme.

Jeff: Talk about PayPal in terms of the PayPal Mafia, the people that were involved with Thiel and that company, and the tentacles that they have today, the influence they have today, in Silicon Valley, and in turn in all of our lives.

Max: The PayPal Mafia, it’s not literal mafia, but it is this influence network where a bunch of early executives of PayPal, these are mostly people who were close friends of Peter Thiel at Stanford and who were ideologically aligned with him, although there are some exceptions to that, have now proliferated in Silicon Valley, and have invested in each other’s companies, have moved money around, and also moved talent around. So, it’s really common for people who work for one PayPal Mafia company to jump to another within this network. Loyalty is a huge thing. Loyalty both to Peter Thiel but also to these companies.

And these people have in general, again, worked together to promote each other’s interests. And the universe, the number of companies they’ve touched, is just enormous. Elon Musk is attached to the PayPal Mafia, even though he and Thiel disagree on a lot of things. He’s the founder of Tesla and SpaceX, Thiel’s a major investor in SpaceX. Reid Hoffman, close friend of Thiel’s from Stanford, started LinkedIn. You got the YouTube guys. You have the guys who started Yelp, the rating site. And then you have a bunch of lesser figures who have ended up putting money into pretty much almost every Silicon Valley company that anyone’s heard of. So Thiel has his hooks in a whole lot.

Jeff: And of course, his hooks are also in Facebook as one of the first outside investors, and also was a longtime mentor to Zuckerberg.

Max: Yes, absolutely. So Thiel was the first outside investor in Facebook. Reid Hoffman is a close friend of his. Another PayPal Mafia member was involved in that, Thiel as well. And Thiel was really the first person, not just the first investor, but really the first person to see promise in Mark Zuckerberg. To realize that this little piddling company started by this guy from Harvard, who had gotten a lot of attention for basically hacking an aspect of the college’s software system, actually had something special. That he was going to be this force of nature. That somebody’s going to run a really successful business.

Thiel is the one who sets up Mark Zuckerberg in the role that he’s currently in. So, Mark Zuckerberg right now controls Facebook but does not own more than 50 percent of Facebook. But because of the structure that was set in part by Peter Thiel, controls the company. He’s essentially the absolute dictator of this media platform that is bigger than any media company in human history. Three billion users, just an enormous amount of reach and influence. And that’s Thiel; that’s Thiel’s work. And then Thiel became this mentor to Mark Zuckerberg, both as a business mentor.

And you can see the PayPal ethos and the Thiel ethos in the way that Facebook expanded, in the way that Facebook was willing to “disrupt things” and sometimes take a lot of flak for, say, not being careful enough with users’ data or whatever. And you also see it in the politics of it, which came out much later. But Zuckerberg seems to have absorbed at least some of Thiel’s libertarian values. And those, I think, we saw coming from Facebook, especially during the 2016 and 2020 election.

Jeff: What seems unique about Thiel? And you talked about this at the outset. About the libertarian streak that certainly has long been part of Silicon Valley. And Thiel to a large extent embodies that, and as you write about, has driven it. But there’s also a cultural side to Thiel’s conservatism that is out of place and different from the Valley. Talk about that.

Max: So, Thiel is a cultural conservative, and somebody who has spent a lot of his career really focused on the problem as he sees it of “political correctness.” And by that what he means is the extent to which institutions have bent over backwards to cater to the needs and feelings of women and minorities primarily. So, Thiel wrote a book in the mid- ‘90s called The Diversity Myth, basically railing against Stanford’s efforts to be more inclusive. And he has seen “political correctness” as this scourge. If you were to rank the biggest problems in the world that would be one of them.

And that seems really, as you said, out of step with the values of Northern California and the tech industry, which in general these companies are very inclusive and they include a lot of immigrants. But on the other hand, you can see why that might have happened. So, one thing is Thiel loves these troublemakers and this need to disrupt, and you could see “political correctness” again as being opposed to that.

And I think it also helps explain why did Peter Thiel back Donald Trump. There were a lot of questions asked in 2016 like, “Why does this gay immigrant with two Stanford degrees, who’s all about technology, embrace a nativist New Yorker who wears his crassness as a credential, who brags about not using technology, and who’s putting forward a reactionary platform?” And I think the reason is Trump was one of these people who was willing to say the unsayable.

Thiel has been getting close to and doing so himself, making these statements and promoting these statements that go right up to the line of what is considered racist or sexist, or many times cross that line. And Trump is the same thing. A key part of his appeal was he was the one who’s going to stick it to the liberal establishment, say the unsayable things. Trump would rail against political correctness. So, I think that was a place where they connected, and that’s ultimately why Thiel supported Trump, is because of that fact.

Jeff: Why didn’t Thiel play a bigger role with Trump ultimately?

Max: Well, that’s a really good question. So Thiel, because of the speech he gave at the Republican National Convention. Then he makes a donation in mid-October 2016, not long after the leak of the Access Hollywood tape where Trump was caught on tape seeming to endorse sexual assault. That support, which came at a really crucial moment for Trump, puts Thiel on the inner circle. He’s on the transition team, he has a huge portfolio during the early days of the presidential transition and has a lot of influence in the White House early on.

Now, what did he do with that influence? Well, he pushed for a lot of very far-right and were just really out there figures. I talked to Steve Bannon for the book, and Bannon said, “If you thought we were crazy you should’ve seen what Thiel was doing.” He was putting forward people who were really too far out there even for Donald Trump. And it’s easy to say, “Okay. Well, that looks like a huge mistake, right?” He totally screwed up. He wasn’t able to maximize his influence.

On the other hand, despite not having a huge influence on the Trump administration, he did manage to get quite a lot of access, and access not just for him but for people in his inner circle. So there was this meeting in December 2016 where Thiel brings in the founders, CEOs of the biggest tech companies in the world. And it’s all the big names, all the companies you’ve heard of. And then one that you maybe haven’t heard of, which is Palantir, which was tiny compared to the other ones. But the Palantir CEO, good friend of Peter Thiel’s, Alex Karp, gets in the meeting and is able to pitch his services to Donald Trump.

And from there you can’t draw a straight line. We don’t know exactly what procurement decisions were made and why, but Palantir gets a huge series of government contracts, more than a billion dollars in government contracts, over the next few years. And that really propelled the company into a new class where its valuation soared, it goes public, Thiel’s net worth goes way up.

So, there’s an extent to which yes, Thiel failed maybe politically, but he didn’t fail in terms of business; his net worth went up. And I would even argue that what looks like a political failure may not be clearly so. And I say that because of course, the Trump administration didn’t end super well for Donald Trump or for many of his allies, but Thiel, because he had sort of lost his juice in the White House a couple of years earlier, doesn’t end up taking responsibility for any of that.

So, he’s able to keep his credibility as this hard right, Steve Bannon-esque ideologue without taking any of the blame for the obvious failures of the Trump presidency, including the impeachment, the slow response to COVID-19, and then the January 6th failed insurrection. None of that stink really gets on Peter Thiel, and instead, he comes out of this as this very ideologically pure money man who is now promoting this new generation of candidates, spending more money than he’s ever spent before.

And there’s a real chance that Thiel could have four people. He’s got two candidates in Senate races right now, and then there are two candidates who he’s done a lot to support who are already in the Senate: Ted Cruz and Josh Hawley. But he could be close to four Republicans in a Republican-controlled Senate after 2022. And I think if that happens, you’re not going to say, “Oh, it was a total failure,” you would say, “Well, he was setting himself up for this higher level of influence.”

Jeff: What’s more important to Thiel, the money side of it or the political side of it?

Max: I really liked that introduction about the Koch brothers. When I was working on this book I read this book Kochland, which I recommend. It’s a profile of Koch Industries, and it describes the way that Koch Industries, the business project was inseparable from the political project. These two things were working together. And I think that’s absolutely how you should look at Thiel.

So, it’s not like, “Oh, he’s an idealogue who also does tech investing,” or, “He’s a tech investor who happens to just have some of these crazy right-wing ideas.” These things are all connected. And his ideological standpoint, this hard libertarianism, the idea that tech billionaires are this privileged class, that ends up both feeding into the tech companies and supporting them. I think those two things are inseparable. Thiel is doing work in politics because it helps his business. He’s also doing business because it helps fulfill his ideological project.

Jeff: In many ways because of the libertarian side of it, because of the disruptive side, the one thing that doesn’t always seem to fit neatly into the package is what he did vis-à-vis Gawker. Talk about that.

Max: Well, I think there are lots of ways in which Thiel is not really a libertarian. And as soon as the book has come out, I’ve actually gotten some notes from other tenants like, “Thank you for saying that because our honor is being—” Peter Thiel, he does have some libertarian values, but he is not a libertarian in the conventional sense. He started a major data mining and defense contractor, obviously not usually a libertarian thing to do to the extent you care about privacy, and he masterminded this litigation that ultimately destroyed Gawker Media. And in both cases, there is some justification.

There are people who defend Peter Thiel. And I think if you had Peter Thiel on the show, he would make the case that actually Palantir is consistent with libertarianism because even though they’re data mining, they’re doing a good job of it. And that the Gawker litigation is consistent with libertarianism because Gawker was a singularly bad actor. It had to be stopped, it had to be destroyed to keep the press free. Which I think is kind of an Orwellian argument, but it is the argument that he would make, which I think is interesting.

But I think it’s also worth saying that the Gawker litigation, it didn’t just destroy Gawker. It created a new framework and a new playbook, where in addition to destroying this company that Peter Thiel regarded as a bad actor, it sends a message to anyone else who’s going to try to write about Peter Thiel, or any source who is tempted to tell a journalist what they’ve seen or what they’ve heard, and not just with respect to Peter Thiel, but with any billionaire. People keep saying to me “Are you scared of Peter Thiel? Hey, he destroyed Gawker. He’s not going to like the author of a book about him.”

And I say, “Well, yes. I mean of course, but I’m scared of any billionaire because that’s the Thiel playbook.” There’s nothing stopping somebody else from doing the exact same thing that Peter Thiel did. He’s created both an example and a permission structure for anyone to pursue similar litigation.

Jeff: But in many ways the Gawker case reveals, I would think, Peter Thiel’s glass jaw, because what he’s most unhappy with is being an outcast in that way. He wants to be an iconoclast, but he doesn’t want to be an outcast, and there’s a fundamental difference.

Max: Yes. So, I think it’s important to say that the inciting action that led to this litigation is blog posts that Gawker published that outed Thiel as gay. Thiel had been out to colleagues and to friends but not to the larger public. I think that post was bad, and I think most editors now would not have published it. I’m an editor and it makes me uncomfortable as a journalist.

But I think we can say that while also saying that the destruction of a media outlet through secretive litigation that took eight years and that resulted in a judgment that was more than $100 million, that caused the personal bankruptcy of the owner of the company, that caused 100 people or more to lose their jobs, that that was not an appropriate response to what had happened. And then it’s a response that could have had really harmful side effects. And I also think you’re right. There is a tendency where the crowd that is railing about cancel culture and political correctness and complaining that we’re catering too much to minority groups or whatever, they’re asking for their own safe space.

There’s something strange about it. And it starts to feel like they’re not actually railing against identity politics, they’re just talking about a different kind of identity politics, and it’s a white identity politics, which is not a phrase you see very often. But I think it does describe both Trump and Trumpism and use Trump as candidate, and to some extent, what Peter Thiel’s pushing, which is this fear that some central aspect of white culture is being destroyed by multiculturalism. And that I think can lead you to some really, really dark places.

Jeff: And Thiel has been on that same course, as you say, from the time he was at Stanford, and even worked for Bill Bennett in the Reagan administration.

Max: Yes, absolutely. Thiel was very early in recognizing the alt-right, this very extremely online group of far-right activists, was a force. And one of the reasons he was early there, one of the reasons he saw it as powerful, one of the reasons he supported it, is because those people were very similar to the kind of person he was in college. And really like Thiel’s newspaper and these political troublemakers that he funded at Stanford, some of whom are really some of the most influential people in Silicon Valley.

The editor of the Stanford Review rape issue, which does not express — I think the views are pretty out of step with today’s understanding of sexual assault — he’s a big-time venture capitalist now. David Sacks, he’s an ally at Thiel. As I said, these guys were very far out there, and I think in many ways prefigured the rise to alt-right.

Jeff: Is Thiel in it for the long run? What do you think his longevity is?

Max: Well, there is some question there because, of course, anyone who was closely connected to Trump or closely connected especially to the events of January 6th has seen their star fall a little bit, including, of course, the former president. But I think Thiel has navigated this pretty well, and I don’t think he’s suffered much. I think he’s definitely well set up to continue to play this political role, maybe to have even more power over the next decade than he had in the previous decade. He’s continuing to play this big role as an investor, as a behind-the-scenes player in the tech industry.

And one thing about that, it’s not just that Thiel is playing this role. There are dozens of people, more, hundreds of people who styled themselves, were like miniature versions of Peter Thiel, either because they work with him directly and they’re actually literally managing his money, moving his money around, or because they just have read his books and watched his YouTube speeches and drunk in this ideology.

He’s got a huge following, and so whether or not Peter Thiel himself continues to play this role, this Thiel-ism is not going away. And knowing Peter Thiel, having studied him and talked to 150 people who’ve worked closely with him or his friends or whatever, I really think that this is somebody who is incapable of not trying to be that provocateur, not being that bomb-thrower. So I think it would be very hard to see him just riding off into the sunset with his $10 billion now. He’s going to want to continue to be making waves, and then we’re going to all be reckoning with the results of that going forward.

Jeff: Max Chafkin. The book is The Contrarian: Peter Thiel and Silicon Valley’s Pursuit of Power. Max, I thank you so much for spending time with us.

Max: Jeff, thank you for having me. It was a pleasure.

Jeff: Thank you. And thank you for listening and joining us here on the WhoWhatWhy podcast. I hope you join us next week for another Radio WhoWhatWhy podcast. I’m Jeff Schechtman. If you liked this podcast please feel free to share and help others find it by rating and reviewing it on iTunes. You can also support this podcast and all the work we do by going to

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