Who’s Funding Bari Weiss?

Tim Draper
Photo By Cody Glenn via Getty Images
Theodore Schleifer
November 12, 2021

Venture capitalist Tim Draper has a reputation as something of a quack. He regularly wears the same, hideous purple-and-yellow Bitcoin-emblazoned tie. He memorably defended Elizabeth Holmes long after Theranos was exposed as a fraud, casting his portfolio founder as the victim of a “witch hunt.” Lots of reporters and Silicon Valley insiders roll their eyes whenever anyone says his name.

But he is also very rich. The Drapers, after all, are a Silicon Valley institution: Tim’s grandfather was one of the first venture capitalists in the Bay Area, and Tim co-founded one of its iconic firms, Draper Fisher Jurvetson. His son, Adam—who made a killing as a seed investor in Coinbase—constitutes a fourth generation of Draper startup investors. Tim was also, as we now know, unequivocally right about the value in Bitcoin. Forbes pegs his net worth at $1.5 billion, but given his crypto holdings, that’s probably way off.

And for decades he’s channeled that fortune into politics. His quests have been—and I’m being awfully charitable here—quixotic. In 2014, he tried to pass a measure splitting California into six states. In 2018, he reconsidered—the real solution was to split California into three states. Last year, Draper endorsed Mighty Ducks child star-turned-crypto evangelist Brock Pierce as President of the United States—support that helped Pierce gain 0.03 percent of the national popular vote.

So I wouldn’t blame you if you didn’t know whether to take Draper seriously. I waffle myself. But I’ll tell you who is taking him seriously: California politicos, who are watching Draper kick off a fantastically ambitious, and likely doomed effort to kill the state’s public-sector unions. Draper is the author and funder of a new ballot initiative that would ban the unions that California teachers, firefighters, cops and other government employees use to collectively bargain. Draper has until around April or so to collect 1 million signatures, a tall order, but not a herculean one for a billionaire who in the past has shown little inhibition about emptying crypto winnings into political misadventures.

Draper spent $20 million in 2000 to push for school vouchers. His first stab at the dissection of California cost him $5 million. He dropped another $1 million the second time. Gathering 1 million signatures this time is likely to cost up to $10 million. Draper, I’m told, is working with top California election lawyer Tom Hiltachk. I asked Draper a number of questions, including how much he is prepared to spend, but he wouldn’t say. “It is still pretty fluid,” he offered instead. Draper suggested he was unsure of how to proceed in part because of a “horrific” summary offered by the California Attorney General of his proposal. “We are evaluating our options. We need to do something about political/union bias in Sacramento. California is broken.”

It should go without saying that if the ballot initiative did qualify, Draper would be poking a hornet’s nest. California’s unions have more money than God, and a political machine to match. They would have to empty the bank account to defeat this and leave nothing to chance. After all, for Big Labor, a measure to ban public-sector unions would be the definition of an existential threat. I would think that organized labor would carry the day in a heavily Democratic state. But even if unsuccessful, Draper could bleed the unions dry. So I’ll be paying attention.

Peter Thiel’s $20 Million Synergy

You probably know by now about the two Peter Thiel mentees seeking to join the U.S. Senate: Blake Masters, Thiel’s longtime consigliere who is running in Arizona, and J.D. Vance, the Thiel disciple who is making his own bid in Ohio. But what you may not have paid attention to is how the two separate campaigns in separate states are increasingly merging with one another, working in concert to achieve synergies as if they were both portfolio companies in the Thiel Capital network.

Thiel donated an identical $10 million to each of their separate super PACs last spring. More recently, however, the two campaigns have come to resemble one another—and forged a more explicit alliance that is unusual for candidates who are not yet the nominees. Two weeks ago, Masters and Vance set up a new joint-fundraising committee, the “Masters Vance Committee,” that allows them to accept joint contributions. (The first big checks came via a joint fundraiser hosted in New York City by Thiel friend Rebekah Mercer. More events, I’m told, may be in the offing.) Masters’ campaign manager at one point used to work for Vance. The super PACs for both candidates also hired the same pollster, Tony Fabrizio, who polled for Trump’s campaign (although he runs a big firm so that’s not as revealing.)

Masters and Vance appear to share some strategy, too. Last month, the pair co-authored an op-ed in the New York Post, splaying Mark Zuckerberg for how he treats Republicans. More humorously, both candidates in recent months have sent nearly identical tweets—with the same formatting and the same red-siren emoji—auctioning off dinners with Thiel to donors who cut max-out checks to their campaigns, an idea that Vance asked Masters about and then borrowed from him. (Vance himself maxed-out to Masters’ campaign in September.) Masters, in turn, has spoken fondly about Vance’s candidacy, framing their two campaigns as part of a generational turning-of-the-page in the G.O.P.’s reorientation toward millennials.

Masters and Vance are friends and text and talk regularly, I’m told, and so it makes sense that the two candidates are watching each other, sharing ideas and best practices. (I hear the Thiel auctions/fundraisers have been very successful.) They have similar ideology, too, with overlapping concerns with globalization, “cancel culture” and election integrity. And yet the alliance between candidates in different states is unusual—primarily because neither of them has yet won their primaries, but also for how it calls attention to Thiel, one of the longest-serving members of the Facebook board. That has surprised me since Masters and Vance are running, of course, as populists. But maybe it shouldn’t: Thiel is not quite a celebrity, per se, but he has become a celebrated brand in elite conservative culture. So much so that Vance’s Twitter followers would pay $11,000 just to have dinner with him. I’m guessing they wouldn’t do that for Miriam Adelson. 

Both remain solid underdogs in their Republican primaries. The other candidates in Ohio and Arizona are turning out to be pretty well-funded, meaning that Thiel hasn’t yet proven to be a decisive kingmaker. The big question isn’t who has Thiel’s support, but who has Donald Trump’s. That’s why the most consequential development was the Trump-hosted fundraiser for Masters at Mar-a-Lago on Wednesday night alongside Thiel allies like venture capitalists Joe Lonsdale and David Sacks. “I will make no predictions about an endorsement or anything like that,” Masters said Tuesday night in a public appearance in advance of the shindig. “Obviously I hope to earn his support. Maybe that takes a lot of time.” For now, the photos will suffice.

The Bari Weiss Underwriters

Lastly, speaking of Lonsdale, the Texas transplant is one of the high-profile names behind the University of Austin, the new, not-yet-accredited school being launched in part by conservative writer Bari Weiss to advance the cause of free speech. That’s a value that’s also shared by Lonsdale, a co-founder of the school who has long argued that intellectual debate is being stifled in society, in general, and in academia, in particular. “We are challenging a jealous orthodoxy and expect to be scorned, mocked, and even viciously attacked,” Lonsdale said this week in an op-ed, also in the New York Post. “But with a healthy amount of courage, determination, and yes—money, it can be done.” 

At least some of that money is coming from Lonsdale himself, via his nonprofit group, the Cicero Institute, which is actually the fiscal sponsor of the private school. That’s a common-enough arrangement in cases when a nonprofit doesn’t yet have tax-deductible status from the IRS. (The University of Austin is currently applying to become an independent 501(c)3 charity.) A school spokesperson described Lonsdale as one of their “leading benefactors” and said they are “honored to have his support.” 

The school claims it is “in the process of securing $250 million” to launch Weiss’ school and has received 700 donations on its website since launch. There is an appreciable economic logic to the endeavor. The University of Austin says it will charge about half the tuition of a private college, or $30,000 a year, and offer a no-frills, no-sports, no-overhead experience. A huge number of Weiss’ supporters and allies have already expressed their interest. And there are enough wealthy conservatives (new Texan Elon Musk?) that I predict they will have no trouble raising even more than the $250 million. The potential return on investment is pretty incredible: for a few million bucks, donors can seed a new movement to create more Bari Weisses.