Should Mark Zuckerberg be scared of Peter Thiel?

Unless you’ve been in a cave over the last week, you’ve likely read a review or some discussion about “The Contrarian,” a new book about billionaire investor Peter Thiel by longtime Bloomberg Businessweek features editor and tech reporter Max Chafkin.

It isn’t surprising. Thiel has become an increasingly powerful figure in the U.S., and Chafkin is an engrossing storyteller who poured 15 years of reporting into the book and who leaned on relationships with “hundreds of sources,” he writes in its acknowledgements.

To learn more, we talked with Chafkin last week in what proved to be a lively discussion that covered how much Thiel (who talked with Chafkin off the record) revealed of his personal life; why the “Trump thing was partly ideological, but it was partly a trade — an insight that Trump was undervalued,” says Chafkin; and why Thiel’s beliefs are “extremely inconsistent,” according to Chafkin’s reporting. We also discussed Thiel’s relationship with Mark Zuckerberg, who accepted one of Facebook’s first checks from Thiel and who has been bound, for good and bad, to Thiel since.

You can hear that 30-minute interview here. In the meantime, we’re pulling out a part of that conversation centering on Zuckerberg because we find Zuckerberg’s relationship with Thiel to be particularly fascinating and important, given the impact of Facebook on American society and humankind more broadly. We’ve edited this excerpt lightly for length.

TC: You talk about Thiel’s biggest and most important bet really being Facebook and suggest in the book that he used his position as a board member since 2005 to persuade Mark Zuckerberg to be more allowing of an anything-goes type stance, even misinformation. You also suggest there has been friction between Thiel and Zuckerberg for some time, especially as Thiel has come to embrace Trumpism. Do you anticipate that Thiel will be a Facebook board member for much longer? Do you think he has been sidelined in any way?

MC: There’s an anecdote in the book: When Facebook went public, its stock crashed and Thiel sold the stock pretty quickly, but of course he stayed on the board [and in the book] I talk about this meeting they had at the Facebook campus to kind of pump people up, because when you’re working in a company and the stock is going down, I understand that it’s the world’s most depressing thing. Everybody every day is losing money. The press is beating you up. They were getting sued by firefighters and teachers. It was just an endless parade of bad news. So they had all these speakers come in to try to pick up the troops. And Peter Thiel gave a talk. And during the talk, he said, ‘My generation was promised flying cars. Instead we got Facebook.’ Normally he attacks Twitter [with that language]. He says, ‘We were promised flying cars, but we got 140 characters,’ but he made it Facebook in this case, and if you’re sitting in a crowd, or if you’re Mark Zuckerberg, it’s like, ‘Oh, so the longest-serving board member, mentor, guiding light of my business philosophy, just kind of got up there and told me I sucked.’

I do think that Zuckerberg actually kind of respects that about Peter, right? When you’re Mark Zuckerberg, it’s very hard to get honest feedback. No one’s gonna ever tell you that you suck except maybe Peter Thiel. But as you say, Thiel has really kind of been tiptoeing up to the line a lot over the last few years.

[Thiel] has often talked about tech monopoly and tech power, and he singles out Google, which . . . maybe takes the heat off of Facebook, but it doesn’t help that much, because Facebook and Google are very similar companies, and if you’re going to regulate one, you might conceivably regulate the other. I’m not sure Zuckerberg is thrilled with that.

Thiel has at various times embraced this kind of right wing activist project in Silicon Valley. You have [conservative activist] James O’Keefe and others who are intent on exposing what they see as the hypocrisy of Facebook, Google, Apple — all the big tech companies — and Thiel has subtly embraced those.

But he’s also increasingly embracing them in public. Right now, Thiel has two candidates running in the U.S. Senate races. They’re both running in Republican primaries: Blake Masters in Arizona, and JD Vance in Ohio, and Thiel has donated ten million bucks to super PACs supporting each of these candidates. These guys are constantly attacking Facebook, and not just attacking Facebook on an intellectual level or raising questions. They’re making almost personal attacks against Mark Zuckerberg. There’s a JD Vance ad [funded by Thiel], where it’s these dark tones, and it’s like, ‘There’s a contingent of elites in this country who are out of touch,’ and there it is — there’s Mark Zuckerberg face. I mean, if I’m Mark Zuckerberg, God, that must be just a continual source of a headache.

There was one instance [in 2017] where Zuckerberg asked if Thiel thought he should resign, and Thiel did not and Zuckerberg didn’t fire him, so there has at least been some tension. [As for whether] Thiel’s value has diminished, that’s a really astute question because with Biden in charge, with the Democrats in power controlling the presidency and both houses of Congress, Thiel’s connection to the right is less valuable. That said, there’s a very good chance that Republicans will retake the Senate in 2022. And there’s a chance that that some of those senators will be very, very close to Peter Thiel, so that could drastically increase his value.

TC: You mention in the book that a lot of people who are close to Thiel and admire him are also terrified of him. Despite the fact that Mark Zuckerberg is probably the most powerful person in the world, I wonder if your sense of things is that he’s scared of Thiel.

MC: I think Zuckerberg could fire Thiel. I mean, Mark Zuckerberg is a formidable guy. He’s worth a lot of money. He could afford a war with Peter Thiel, and he could afford the backlash. But I think there’s a question about whether he’d want to, because right now, the reason Thiel is able to get away with what he’s able to get away with, with respect to both serving on the board and being this public critic, has to do with the fact that there would be a price to pay if Mark Zuckerberg fired him, and the price would be it would be a huge freaking story.

Thiel had been such an important ally to Mark Zuckerberg during the Trump presidency. There have been these running memes in conservative circles that Facebook is systematically discriminating against right wing points of view, [that it’s] a liberal company staffed by liberal employees who hate Donald Trump, and that as a result, it is putting its thumb on the scale and advancing the interests of the left. . . [But] Zuckerberg had an awesome response to that, which is ‘Hey, I’ve got this board member. He’s not just a Republican. He’s not just some kind of middle-of-the-road conservative like George Bush guy or something. He is Peter Freaking Thiel. He’s the guy who’s too crazy for Steve Bannon. He is a dyed-in-the-wool Trumpist.’ And that gives Facebook a really, really powerful argument.

When somebody like Josh Hawley, who has taken money from Peter Thiel, or Ted Cruz, another person who has taken money from Peter Thiel, comes along and attacks Facebook . . . I think if [Thiel] left, especially if he was fired — if that was a story that came out — it would be open season.

I don’t think it’s an existential issue for Mark Zuckerberg. But I think it might be more comfortable to keep his friend and board member Peter Thiel, despite the fact that they might have some profound differences of opinion on the value of Facebook.