Inside Peter Thiel’s Life After Facebook

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Come May, Peter Thiel plans to leave a post he has held for 18 years: board member of Facebook’s parent company. Thiel has already planned a party.

A few weeks later, the fete will take place at Blake Masters’ island property near Miami Beach. It is a two-home bay-front home that he bought for $18million last year. 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. Tiered attendance is possible at the event. VIPs will be able to enter at 6 pm, while partygoers can go in at 6:45 (at a cost of $1,500). Thiel Masters and Thiel are more likely to get along with VIPs. There’s a third level, too: $5,600 for billing as a cohost.

Thiel is hosting a fundraising event for Masters Miami at the very least. In December, about 100 people gathered to drink cocktails and take pictures around Thiel’s pool. View Ana Navarro, CNN commentator and host, was there as well as Madison Cawthorn (North Carolina Congressman). 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. Masters is a Stanford graduate who runs Thiel Capital. The company has invested in companies such as SoFi online lender and Regent (a maker of an electric seaplane). Masters manages Thiel Foundation. This foundation provides annual grants for 225 students who are not enrolled in 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) is still extremely wealthy. His net worth was estimated at $2.7 million. It seems impossible that Thiel would give up his empire of startups investments which he built 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. He is clearly at an inflection. 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. The one supports Masters and the other J.D. Vance Hillbilly Elegy Author vying for Ohio Senate seat. This is a sign that Democratic Silicon Valley donors may be pulling back and giving less to the next presidential cycle.

In recent years Thiel has become more of an enigma, inscrutable and secretive as well as 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. Thiel’s current activities, donors, and candidates are all important to understanding. Thiel, who has once again restructured venture capital, plans next to forcefully do the same for Republican politics over many years, choosing contenders that can best be described as one-third Trump and 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. Thiel and Koutoulas live roughly 15 minutes from one another. “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 wants to hold on. You can see the contradiction between all of the Blue Cities. Once-great New York, San Francisco and LA are now just high crime, high taxes.”

BWe should start somewhere humbler before we go to Thiel as the Republican Kingmaker. 

Foster City is a place similar to 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 father 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. Thiel decided that he liked working for himself more. Thiel Capital and Clarium Capital were established by him in 1996. Clarium saw 30% in annual returns before the Financial Crisis. 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, every person who passed on the money would be a new customer,” he said. SME In 1999. Levchin and Thiel took PayPal public in 2002. It was then sold to eBay eight months later for $1.5 billion. Thiel took home $55 million.

Thiel created Founders Fund three years later. He amassed shares in several of the most important companies during the last fifteen years through Founders Fund and other businesses, such as Lyft Space X and Lyft. Palantir is a controversial company that makes surveillance software. He was able to also manage to cofound it. 

Thiel the investor was already a well-respected name in his field. His deal flow was aided by his openness to breaking the Silicon Valley mold. He was at home with founder CEOs ruling supreme in startups, and retaining voting and economic power. It’s not how the old guard on Sand Hill Road liked things. To keep up with him they needed to adapt, and that meant they would have to give up their preferences for a check-and-balances system in favor of a chief executive officer to secure investments. “What Peter did was fundamentally change the nature of the venture capital industry,” says Jim Breyer, founder of Breyer Capital. He has invested with Thiel and his companies more than 12 times including in Facebook. “In my view, it was extremely healthy. Others may not have felt it was a positive dynamic.”

Thiel was introduced to Reid Hoffman, the founder of LinkedIn. He also heard of 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 in the midst of its own development, adding new features to it, including notifications, News Feed and access 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 invested in Facebook, and also served as a board member with Thiel (and Breyer). “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. Two things, Trump and Gawker, prompted a shift in Thiel’s behavior around 2015. He was accused by the media of financing. the libel lawsuit leading to Gawker’s demise. Thiel was outed as gay on a newsblog site in 2007 which angered 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. Thiel donated $1 million and $200,000 respectively to a pro Trump Super PAC that year. It prompted criticism from the press and from Thiel’s peers. Reed Hastings (the Netflix founder and also the Facebook director) was one of those who were criticised. The following is an extract from 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 was removed 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. There are many contradictions in these events. Most notably, Facebook (the company Thiel built) must ban Trump (the President Thiel helped to get elected) off 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. Maybe Trump was expelled (his man). 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.”

TThiel has provided funding for 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 Thiel Land also offers reference. Thiel and Vance both have invested in Rumble. Rumble has a right-leaning online platform. Their political beliefs are similar to their money. They support an America-centric policy with lower government spending, tougher immigration policies and a more America-centric approach to foreign affairs.

Vance, who is currently in an intense contest for the Republican Primary, has been bombarded by ads showing outdated tweets of Vance, criticizing Trump, to obstruct Ohio TVs. Vance deleted the tweets and is now trying to follow Thiel. Trump. Recenty, Trump has been using Twitter to increase funds. He advertised an $10,800 per-plate dinner with Thiel and him.

Then there’s Masters, who, as Trump might put it, seems straight out of central casting for a Thiel Candidate. Masters supports stricter rules regarding immigration and less involvement in foreign affairs, just like Trump and Vance. He is 100 percent on the MAGA train with Thiel. In January, Masters sent this tweet:

And like Thiel, he’s been quick to seize on the promise of emerging technology. Masters, who had the original digital money created by Paypal and Thiel, has NFTs. Masters was able to sell a limited edition run of NFTs at $5,800 each in December. The tokens were a digital-collectible, digital-approved version of From Zero to OneThiel coauthored the well-received, yet abstractly written book “Startups,” which he wrote with Thiel. The NFTs will be included in the package. Buyers will receive invitations to Master’s parties and access to the Discord private group. In raising $574,000, he sold 99, making it one of the first times that NFTs are being used in politics.

Trumpism combined with crypto are two of the reasons James Koutoulas was a successful hedge fund manager, who attended Thiel’s Miami fundraiser. “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.”

Vance will likely win, but it is too soon to predict. Not every Thiel Candidate won in the past few years. He spent $1 million on a lost Senate race by Chris Kobach last year. (As Kansas’ Secretary of State, he enacted some of the nation’s toughest voter-registration laws.) Thiel donated $2,900 less to Loren Culp in Washington. His campaign spiraled as well. Culp responded Trump-style, filing a lawsuit over election irregularities after his defeat. 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.

Vance and Masters may be able push for $20 million, which could tip the Senate in Republican favor. A terrifying scenario to the left. Theil’s spending has unsettled Democrats, who are looking around for their own big money guys. Marc Benioff, Salesforce CEO, is still sitting things out. This vow was made after he bought Salesforce. 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. Hoffman and Benioff would not 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 believes that the party will one day come together. “I don’t think it will go unanswered.”

The opposing and well-funded right answer can still be heard loudly, if you’re sitting at the poolside table with Peter Thiel.

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