Inside the mind of Peter Thiel, Donald Trump’s tech bestie

The Facebook cofounder and funder of Hulk Hogan’s Gawker case is now on team Trump

Let others tremble at the thought that Donald Trump may go too far. Peter Thiel worries that Trump may not go far enough.

“Everyone says Trump is going to change everything way too much,” says the famed venture capitalist, contrarian and member of the president-elect’s transition team. “Well, maybe Trump is going to change everything way too little. That seems like the much more plausible risk to me.”

Thiel is comfortable being a walking oxymoron. He is driven to save the world from the apocalypse, yet he helped boost the man regarded by many as a danger to the planet.

“The election had an apocalyptic feel to it,” says Thiel (49), wearing a gray Zegna suit and sipping white wine in a red leather booth at the Monkey Bar in Manhattan. “There was a way in which Trump was funny, so you could be apocalyptic and funny at the same time. It’s a strange combination, but it’s somehow very powerful psychologically.”


At the recent meeting of tech executives at Trump Tower, orchestrated by Thiel, the president-elect caressed Thiel’s hand so affectionately that body language experts went into a frenzy. I note that he looked uneasy being petted in front of his peers. “I was thinking, ‘I hope this doesn’t look too weird on TV’.”

Off the ledge

I ask Thiel if he had to twist arms to lure some of the anti-Trump tech titans, such as Jeff Bezos and Elon Musk.

“I think, early on, everybody was worried that they would be the only person to show up,” he says. “At the end, everybody was worried they would be the only person not to show up. I think the bigger tech companies all wanted to get a little bit off the ledge that they had got on.

“Normally, if you’re a CEO of a big company, you tend to be somewhat apolitical or politically pretty bland. But this year, it was this competition for who could be more anti-Trump. ‘If Trump wins, I will eat my sock.’ ‘I will eat my shoe.’ ‘I will eat my shoe, and then I will walk barefoot to Mexico to emigrate and leave the country.’

“Somehow, I think Silicon Valley got even more spun up than Manhattan. There were hedge fund people I spoke to about a week after the election. They hadn’t supported Trump. But all of a sudden, they sort of changed their minds. The stock market went up, and they were like, ‘Yes, actually, I don’t understand why I was against him all year long.’”

I note that several Silicon Valley companies have pre-emptively said they will not help build a Muslim registry for the Trump administration. Will Palantir, the data-mining company that Thiel cofounded, and whose clients include the NSA, the CIA and the FBI, be involved in that? (Palantir's chief executive, Alex Karp, sat in at the Trump tech meeting.)

“We would not do that,” Thiel says flatly.

Risk boldness

One could have predicted Thiel's affinity for Trump by reading his 2014 book, Zero to One, in which he offers three prongs of his philosophy: 1) It is better to risk boldness than triviality. 2) A bad plan is better than no plan. 3) Sales matter just as much as product.

Still, he was portrayed as an outcast in Silicon Valley and denounced as a jerk for supporting Trump and giving him $1.25 million. “I didn’t give him any money for a long time because I didn’t think it mattered, and then the campaign asked me to,” he says.

He recalls going through a lot of “meta” debates about Trump in Silicon Valley. “One of my good friends said, ‘Peter, do you realize how crazy this is, how everybody thinks this is crazy?’ I was like, ‘Well, why am I wrong? What’s substantively wrong with this?’ And it all got referred back to ‘Everybody thinks Trump’s really crazy’.

“So it’s like there’s a shortcut, which is: ‘I don’t need to explain it. It’s good enough that everybody thinks something. If everybody thinks this is crazy, I don’t even have to explain to you why it’s crazy. You should just change your mind.’”

On the Russian hacking, Thiel says: “There’s a strong circumstantial case that Russia did this thing. On the other hand, I was totally convinced that there were WMDs in Iraq in 2002, 2003.”

I ask him if he worries about the bromance with Vladimir Putin and Trump's bizarre affinity for dictators. "But should Russia be allied with the West or with China?" Thiel says. "There are these really bad dictators in the Middle East, and we got rid of them and in many cases there's even worse chaos."

So he doesn’t worry about Trump sending an intemperate tweet and spurring a war with North Korea? “A Twitter war is not a real war.”

Careful in emails

Thiel and Trump are strange bedfellows, given that much of Thiel's billions came from being one of the original investors in Facebook and Trump, who is 70, recently said it's better to send important messages by courier. ("Well," Thiel notes, "one does have to be very careful with what one says in an email.")

The president-elect rose by wildly lunging with his Twitter rapier in an “unpresidented” way in the first campaign that blended politics, social media and reality. But the social-media visionary rarely updates his Facebook page and doesn’t tweet because “you always want to get things exactly right” and “if you start doing it, you have to do it a lot”.

As Silicon Valley has devolved into a place that produces apps like one that sends the word “yo,” Thiel worries its thinking is “not big enough to take our civilisation to the next level”.

I ask if it is true that Jack Dorsey, Twitter's chief executive, wasn't invited to the tech meeting because the Trump camp was angry that Twitter wouldn't let the Republican nominee create a "Crooked Hillary" emoji. Thiel replies that "there were people upset about that," but that he set up the meeting according to the market caps of the bigger tech companies.

“I think the crazy thing is, at a place like Twitter they were all working for Trump this whole year even though they thought they were working for Sanders.”

Thiel says he fell into his role in the Trump candidacy. “It was one of my friends who called me up and said, ‘Hey, would you like to be a delegate at the Republican convention?’ I said: ‘Actually, I kind of would. I think it would be fun to go.’ Then, two weeks before the election, they talked to me about speaking at the convention.”

I note that the audience in Thiel’s hometown, Cleveland, gave him a great reception when he appeared as only the third openly gay speaker at a Republican convention. “I’m not sure that my speech was that good,” he says. “I do think a lot of other speeches were just very bad.”

Friends for life

He had his first conversation with the man whom he sometimes calls “Mr Trump” at the convention, when the Manhattan mogul told the San Francisco mogul, “You were terrific. We’re friends for life.” Thiel never did go to a Trump rally or watch a whole video of one: “I would think they were very repetitive.”

At the tech meeting, he says Trump showed “a phenomenal understanding of people. He’s very charismatic, but it’s because he sort of knows exactly what to say to different people to put them at ease.”

I ask him if Trump and Tesla founder Elon Musk are similar. “I’m going to get in trouble, but they are, actually. They’re both grandmaster-level salespeople and these very much larger-than-life figures.”

He recalls a story from his and Musk’s PayPal days, when Musk joined the engineering team’s poker game and bet everything on every hand, admitting only afterward that it was his first time playing poker. Then there was the time they were driving in Musk’s McLaren F1 car, “the fastest car in the world”. It hit an embankment, achieved lift-off, made a 360-degree horizontal turn, crashed and was destroyed.

“It was a miracle neither of us were hurt,” Thiel says. “I wasn’t wearing a seat belt, which is not advisable. Elon’s first comment was, ‘Wow, Peter, that was really intense’. And then it was: ‘You know, I had read all these stories about people who made money and bought sports cars and crashed them. But I knew it would never happen to me, so I didn’t get any insurance.’ And then we hitchhiked the rest of the way to the meeting.”

Totally gay

Trump, with his litigious streak, his pugilistic attitude toward the press and his threat to change the libel laws, naturally admired Thiel’s legal smackdown of Gawker. The tech titan was disturbed by the “painful and paralysing” stories published on the gossipy US website and other blogs under the Gawker banner, including a 2007 post that originally appeared on Valleywag blithely headlined “Peter Thiel Is Totally Gay, People”.

In response, he secretly financed the lawsuit filed by Terry Bollea (the real name of wrestler Hulk Hogan) against Gawker for posting an excerpt from a sex tape showing Bollea with a friend's wife. A court ruled in Bollea's favour, in a judgment of $140 million, which drove the site into bankruptcy. (Gawker founder Nick Denton, who is also gay, described Thiel to Vanity Fair as "interesting . . . and scary".)

“It basically stands for the narrow proposition that you should not publish a sex tape,” Thiel says. “I think that’s an insult to journalists to suggest that’s journalism now. Transparency is good, but at some point it can go in this very toxic direction.”

Just as there was “a self-fulfilling Hillary bubble” where “everybody was just too scared to say this was a really bad idea” to support this “very weak candidate,” Thiel believes Gawker manufactured “a totally insane bubble full of somewhat sociopathic people in New York”. When the case went to court in Florida, he contends, the culture that “you could do whatever you wanted and there were no consequences” was exposed.

"There's some resonances between Hogan beating Gawker and Trump beating the establishment in this country," Thiel says. Hulk Hogan was "this crazy person" who didn't seem like the best plaintiff, but "he didn't give up".

Using two wrestling terms he learned, Thiel says that many people assumed Trump was “kayfabe”– a move that looks real but is fake. But then his campaign turned into a “shoot” – the word for an unscripted move that suddenly becomes real. “People thought the whole Trump thing was fake, that it wasn’t going to go anywhere, that it was the most ridiculous thing imaginable, and then somehow he won, like Hogan did.”

Sort of real

“And what I wonder is, whether maybe pro wrestling is one of the most real things we have in our society. And what’s really disturbing is that the other stuff is much more fake. And whatever the superficialities of Trump might be, he was more authentic than the other politicians. He sort of talked in a way like ordinary people talk. It was not sort of this Orwellian newspeak jargon that so many of the candidates use. So he was sort of real. He actually wanted to win.”

While many predict that President Donald Trump will crash and burn, Thiel does not think he will regret his role. “I always have very low expectations, so I’m rarely disappointed,” he says.

I ask him how Trump, who is still putting out a lot of wacky, childish tweets, has struck him during the transition. Isn’t he running around with his hair on fire?

“The hair seems fine,” Thiel says. “Mr Trump seems fine.”

New York Times Service

Maureen Dowd

Maureen Dowd

Maureen Dowd is a columnist with the New York Times