Poolside Fundraisers, Crypto And Mini-Trumps: Inside Peter Thiel’s Life After Facebook


Come May, Peter Thiel plans to leave a post he has held for 18 years: board member of Facebook’s parent company. In the meantime, Thiel is planning a party.

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The fete will happen a few weeks from now at his island estate near Miami Beach, a two-home, bay-front compound purchased for $18 million a year ago. It’s a fundraiser for Blake Masters, a Thiel protégé running for U.S. Senate from Arizona, and invites have already gone out to a collection of moneyed, pro-Trump GOP elite. The event has tiered attendance: a 6 p.m. start for VIPs (a $2,900 per person donation) and a 6:45 entrance for the other partygoers ($1,500). (VIPs get more time and opportunity to mingle with Thiel and Masters.) There’s a third level, too: $5,600 for billing as a cohost.

It’s at least the second time Thiel has assembled a fundraiser for Masters in Miami. In December, about 100 people gathered to drink cocktails and take pictures around Thiel’s pool. View host/CNN commentator Ana Navarro attended, as well as North Carolina Congressman Madison Cawthorn. Hedge funder James Koutoulas did, too, a giant “LGB” button fastened to his blue blazer. (The pin is a reference to the anti-Biden slogan “Let’s Go Brandon.” Last year, Koutoulas launched a LGB-branded meme coin.)

“I think Blake has a nice combo of technical competence,” Koutoulas says. The Stanford-educated Masters runs Thiel Capital, which has invested in companies like online lender SoFi and Regent, a maker of a new electric seaplane. Masters also manages the Thiel Foundation, the organization dispensing annual grants to 225 young people in lieu of college. Koutoulas perceives the D.C. bureaucrats as lacking any experience like Masters’. “You’ve got so many people in government who don’t have a basic understanding of technology,” he sighs.

For anyone curious about Thiel’s life after Facebook, it will probably look a lot like these gatherings in south Florida. Thiel, 54, remains very rich (estimated net worth: $2.7 billion), and it is inconceivable that he would totally abandon his sprawl of startup investments, an empire he began building 20 years ago. Those stakes form the basis of his wealth; those dollars are what he’s pumping into Republican politics to emerge as a leading figure in a Trump-centric GOP. But he is very clearly at an inflection point. There’s not only his Facebook departure announced on Monday but also his surge in political spending. Just accounting for publicly traceable funds, Thiel has spent $22 million in the last two years–mostly on U.S. Senate and House of Representatives contenders–five times the amount he spent over 2015 and 2016. Much of Thiel’s splurge went to two Super PACs. One supports Masters, the other is for J.D. Vance, the Hillbilly Elegy author gunning for a Senate spot from Ohio. This comes as Democratic Silicon Valley are said to be pulling back, giving less than in the last presidential cycle, satisfied with a victory over President Trump and somewhat leaving midterm Congressional candidates to their own fates.

During recent years, Thiel has allowed himself to appear more and more like an enigma: inscrutable, secretive, silent. (Quite on brand, he didn’t return requests to comment for this story.) Yet it’s possible to crack that cipher if you know where to look. In the past, this meant examining his businesses–plural. To glean an understanding of Thiel these days, you really want to look at the parties he throws, the donors he beckons in and the candidates he funds. Having already once reshaped venture capital, Thiel intends next to forcibly do the same to Republican politics for years to come, picking out contenders who may be best described as two-thirds Trump, one-third Thiel.

People like Koutoulas have already bought into Thiel’s reinvention of himself. Before donating to Masters, Koutoulas admits he didn’t do a “super deep dive” on him. Largely, Koutoulas based his support for Masters on Thiel’s support for Masters. Koutoulas and Thiel are friendly; they live a 15-minute drive from each other. “Since Peter moved to Miami, he’s become very active in the America First agenda,” Koutoulas says. Koutoulas goes on, turning to some standard GOP complaints about the state of the States–their validity depends largely on which party you belong to. “Peter’s basic tenet is: America’s really at a precarious tipping point. Communism is trying to establish a hold here. Look at the dichotomy between all the Blue Cities. Once-great New York, San Francisco and LA are now just high crime, high taxes.”

Before we get to Thiel, Republican kingmaker, we should probably, briefly start somewhere a touch more humble. 

A place like Foster City, California. It’s close to San Francisco–20 miles south–but wasn’t much of anything when Thiel and his family moved there when he was a kid, a final stop in a journey that started in Frankfurt am Main, Germany and included Ohio and Namibia. (His dad was a chemical engineer.) Thiel went to Stanford for undergrad and law school, then worked briefly at a Big Law shop, Sullivan & Cromwell, and as a derivatives trader at Credit Suisse in the early 90s. He decided he preferred to work for himself better. In 1996, he started Thiel Capital, then Clarium Capital, a hedge fund, a few years later. Before the Financial Crisis, Clarium was seeing 30% annual returns net of fees. It had a novel-ish model, taking 25% of a year’s profits and nothing if it lost money (rather than the traditional 20-and-2 approach that enriches a hedge fund’s owners in up years and down ones alike). For investors, Thiel penned letters that sounded like this: “Ours is an age in which classic wisdom has failed…Those investors who limit themselves to what seems normal and reasonable in light of human history are unprepared for the age of miracle and wonder in which they now find themselves.” 

In between Thiel Capital and Clarium, Thiel did a startup—something he and cofounder Max Levchin first called Confinity. Today it’s PayPal. “A $20 bill has a velocity of six-in the course of a year, six people will hold that money for an average of two months apiece. In the digital world we’d get new customers every time one of those people passed along the money,” he told Forbes in 1999. He and Levchin took PayPal public in February 2002 and sold it to eBay for $1.5 billion eight months later. Thiel pocketed $55 million.

Three years later, Thiel started another investment vehicle, Founders Fund. Through Founders and his other firms, he amassed stakes in many of the companies that have defined the last 15 years: Space X, Lyft, Airbnb, Spotify, Stripe, ZocDoc, and LinkedIn. (He also managed to find time to cofound Palantir, the now controversial surveillance software company.) 

Before long, Thiel the investor had established a sizeable track record for himself. That helped his deal flow, as did his willingness to dispense with a Silicon Valley rule. He was comfortable with startups where the founder CEOs reigned supreme, retaining economic and voting power over their companies. It’s not how the old guard on Sand Hill Road liked things. But if his competition wanted to keep up with him, they had to evolve, too, discarding preferences for a checks-and-balances system over a CEO to safeguard investments. “What Peter did was fundamentally change the nature of the venture capital industry,” says Jim Breyer, founder of Breyer Capital. (He has invested alongside Thiel or his firms more than a dozen times, including in Facebook.) “In my view, it was extremely healthy. Others may not have felt it was a positive dynamic.”

Through LinkedIn founder Reid Hoffman, Thiel heard about two other young guys: Sean Parker and Mark Zuckerberg. He liked their idea—Facebook—and put a half-million dollars into it, a 3% stake, and joined the board. Facebook was just then figuring out itself, working on adding features we now see as its hallmark functions: the News Feed, notifications and access to Facebook beyond college students. Here and in the following years, too, it is probably impossible to oversimplify or understate Thiel’s influence on Facebook. 

“You know, Warren Buffett says board members ought to have three qualifications: they ought to be business savvy, deeply interested in the company and truly independent,” recalls Don Graham, the former Washington Post publisher who also put money in Facebook and served alongside Thiel (and Breyer) on the board. “Peter had a huge stake in the company and was passionately involved in trying to make it succeed. I thought Peter was both valuable and smart, and Mark was very, very wise for keeping him there.”

For a good while, Thiel didn’t mind the spotlight and enjoyed several years of a public image portraying him as something of an investing genius, if an offbeat one. A shift came around 2015, seemingly prompted by two things: Gawker and Trump. The media pilloried him for financing the libel lawsuit leading to Gawker’s demise. (The news blog site had outed Thiel as gay in 2007, angering him.) The headlines about him grew darker still when he announced his support for Trump’s presidential early in 2016 before the party’s traditional backers came around to him. That year, Thiel gave $1 million to a pro-Trump Super PAC and $200,000 to the Republican National Committee. It prompted criticism from the press and from Thiel’s peers. One of the latter was Reed Hastings, the Netflix founder who was also a Facebook director. According to the New York Times, he told Thiel in an email “I’m so mystified by your endorsement of Trump for our president, that for me it moves from ‘different judgment’ to ‘bad judgment.’”

Trump won, and Thiel retreated from public view. His support for the 45th president didn’t waver much, and he was a frequent enough presence at the Trump White House, Trump’s son in law Jared Kushner tasked with maintaining the relationship. But for Facebook, Trump’s victory was costly. You can trace a pretty direct line from Trump’s election through to today, the company engulfed by controversies over content moderation and other problems made abundantly clear in last year’s whistle-blower leak. Contradictions and complexities abound in these events, most obviously the fact that Facebook (the company Thiel helped build) has needed to ban Trump (the president Thiel helped get elected) from its platform.

Without hearing directly from Thiel, it’s impossible to know precisely why he feels now is the time to leave Facebook—versus immediately after 2016 or before the last presidential election. Perhaps expelling Trump (his guy) was the final straw. Perhaps it’s nothing more than after losing both Congress and the presidency, Thiel feels now is the time to slam down on the GOP gas pedal. (Facebook’s not talking much either. “Peter has been a valuable member of our board and I’m deeply grateful for everything he has done for our company,” Zuckerberg said in a statement announcing Thiel’s departure.)

What is clear is that, in the years after Trump captured the White House, Thiel’s profile has risen substantially in conservative circles where fealty to Trump is a must and the death of GOP megadonor Sheldon Adelson has left a vacuum of influence, two Trump World sources say.

“He’s such a deep thinker and strategist. He’s 20 years ahead of most people,” says Darren Blanton, a startup investor and former Steve Bannon aide who has become a major pro-Trump donor and fundraiser. “Peter Thiel is obsessed with bringing America back to being a great state.”

To make that happen, Thiel is funding guys like J.D. Vance, who’s running in Ohio for a Senate seat. Vance’s thinking runs closely parallel to Thiel’s. Vance first met Thiel when Thiel gave a lecture at Yale, in which Thiel argued Ivy League institutions (like the ones both he and Vance attended) didn’t help students to their fullest potential. In 2017, Vance went to work for Thiel’s Mithril Capital investment fund. Three years later, Vance raised nearly $100 million from Thiel and others for his own fund, Narya Capital—a Lord of the Rings reference, as are many things from Thiel Land. Vance and Thiel have also both invested in Rumble, the right-leaning video platform. Their politics are as aligned as their money: an America-centric foreign policy, lower government spending and tougher immigration policies.

Ahead of the general election, Vance is in a heated contest for the Republican primary, where a rival has besieged Ohio televisions with ads showing old tweets from Vance criticizing Trump. Vance has since deleted those tweets, attempting to fall in line behind Thiel. And Trump. More recently, he has used Twitter to drum up funds, advertising a $10,800-a-plate dinner headlined by himself and Thiel.

Then there’s Masters, who, as Trump might put it, seems straight out of central casting for a Thiel Candidate. Like Vance and Thiel and Trump, Masters favors harder immigrations rules and a less interventionist foreign policy. Like Thiel, he is 100% aboard the MAGA train, sending this tweet in January:

And like Thiel, he’s been quick to seize on the promise of emerging technology. Thiel had some of the very first digital money with Paypal, Masters has NFTs. In December, Masters sold a limited-edition run of NFTs for $5,800 a piece; the tokens are a digital-collectible version of Zero to One, a well-received but rather abstractly written treatise on startups he coauthored with Thiel in 2014. Along with the NFTs, the buyers will get exclusive invites to parties hosted by Thiel and Master and access to a private Discord group. He sold 99 of them, raising $574,000, one of the first instances that NFTs have been used in politics.

Combining Trumpism with crypto is one of the things that won over James Koutoulas, the hedge fund manager who attended the Thiel-hosted fundraiser in Miami. “The lack of thoughtful crypto regulation we have in this country … is a real problem,” says Koutoulas. “For the U.S. to continue as a financial leader, we need to have a pathway to legitimize security tokens and NFTs.”

It is obviously too early to know whether Vance or Masters will win. And not every Thiel Candidate has prevailed in the last few years. Last year, the person he spent the most on lost, a $1 million down the drain for a failed Senate bid by Chris Kobach. (As Kansas’ Secretary of State, he enacted some of the nation’s toughest voter-registration laws.) In Washington state, Thiel gave a much smaller amount ($2,900) to gubernatorial hopeful Loren Culp; his campaign also spiraled. In defeat, Culp responded Trump style, suing over alleged election irregularities. The litigation didn’t prevail, but he has gotten Trump’s endorsement in his new endeavor, a primary challenge against Rep. Dan Newhouse, one of the only Republicans to vote for impeachment after Jan. 6.

Pushing $20 million to Vance and Masters might be enough to tip the Senate into Republican hands, a scenario terrifying to the left. Theil’s spending has unsettled Democrats, who are looking around for their own big money guys. But Salesforce CEO Marc Benioff is continuing to sit things out, a vow he took after buying Time magazine in 2018. And LinkedIn’s Reid Hoffman has contributed only about a tenth of what Thiel has, leading to speculation about whether he’s happy with the results from a big spend on President Biden in 2020. (Neither Benioff nor Hoffman would comment.) 

“It’s hard to be a savvier giver on the Republican side than Peter Thiel, so I do think that an unleashed Peter Thiel is something we need to be very, very, very worried and very, very vigilant about,” says Cooper Teboe, a top Democratic operative and fundraiser in California. He expects the party will eventually pull itself together. “I don’t think it will go unanswered.”

For the time being, the well-funded, opposing answer from the right can be heard loud and clear, should you sit poolside with Peter Thiel.



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