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.

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…