If you’ve spent any time scrolling through political Twitter or listening to the kind of podcasts that make your liberal relatives cringe, you’ve probably noticed two names popping up together more and more: Peter Thiel and Bari Weiss.
On the surface, it’s an odd pairing. You’ve got the billionaire tech philosopher who co-founded PayPal and Palantir, a man who once famously wrote that "freedom and democracy are no longer compatible." Then you’ve got the former New York Times columnist who made a brand out of being the "sensible centrist" pushed out by a "woke" mob.
But honestly? Their alliance is maybe the most significant power shift in American media and politics right now. It isn't just about two people liking each other’s vibes. It’s about money, institutions, and a very specific plan to build a "counter-elite."
The "Honestly" Connection: Where the Magic Happens
The most visible part of this relationship is Weiss’s media platform, The Free Press. Back in May 2023, Thiel sat down for a marathon session on her podcast, Honestly. It wasn't just a standard PR stop. It was a signal.
Thiel doesn't do many interviews. When he does, he’s usually grumpy or speaking in riddles about the apocalypse. But with Weiss, he was expansive. He laid out a vision that basically serves as the editorial North Star for her entire company. He talked about how "wokeism" in Silicon Valley made it impossible to manage "ideologically-deranged millennial employees."
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More recently, following the 2024 election, Thiel returned to Weiss’s show to take a victory lap. He called the results a "triumph of the counter-elite." This is a key phrase you need to understand. Thiel’s whole thesis is that the current elites—the ones at Harvard, the New York Times, and the State Department—are incompetent and "stagnant." He wants to replace them. Weiss is providing the megaphone for that replacement.
Follow the Money: Is Thiel Funding the Revolution?
People always ask: Did Peter Thiel fund The Free Press?
The short answer is: Sorta, but it’s complicated.
The Free Press (originally the Common Sense Substack) raised about $15 million in a funding round that valued the company at $100 million. While the lead investors are often cited as 8VC (led by Joe Lonsdale) and Marc Andreessen, the "Thiel-verse" footprint is everywhere.
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- Joe Lonsdale: He’s a founding trustee of the University of Austin alongside Weiss. He also co-founded Palantir with Thiel.
- The Ecosystem: Thiel’s associates and the VCs he’s influenced have been the primary backers of the "new media" ecosystem Weiss sits at the center of.
It’s less about a single check and more about an ideological venture capital network. They aren't just looking for ROI; they’re looking for "cultural ROI." They want to build a world where a person can be a conservative or a "heterodox" thinker without being "canceled."
The University of Austin: Building a New Harvard
If you want to see where Thiel and Weiss really converge, look at Austin, Texas.
The University of Austin (UATX) was launched by Weiss, Pano Kanelos, and Lonsdale (Thiel's protégé) as a direct middle finger to the Ivy League. Thiel has famously hated higher education for decades—remember the Thiel Fellowship that pays kids to drop out?
But even Thiel seems to have realized that you can't just destroy the old schools; you have to build new ones. During his 2024 chat with Weiss, he admitted that elite universities are still the best places to "train conservatives" because if you survive a four-year stint at Yale as a Republican, you're battle-hardened.
UATX is the physical manifestation of their shared goal: creating a pipeline for the next generation of leaders who aren't "imperial stormtroopers" of the left (Thiel's words, not mine).
What Most People Get Wrong About the Thiel-Weiss Alliance
A lot of critics think Weiss is just a puppet for Thiel’s billions. That’s a bit too simple.
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Weiss is a traditionalist in many ways. She cares about the "old" American values—free speech, meritocracy, and a strong pro-Israel foreign policy. Thiel is a disruptor. He’s a contrarian who thinks the entire 20th-century consensus was a mistake.
The reason they work together is a "the enemy of my enemy is my friend" situation. They both believe that the current American establishment is "mind-killed."
Key Areas of Alignment:
- The "Machine": Both believe a "machine" of bureaucrats and activists is running the country into the ground.
- The Collapse of Liberalism: They both argue that modern liberalism has become an "intellectual straitjacket."
- Anti-Identity Politics: Both are fiercely against DEI (Diversity, Equity, and Inclusion) initiatives, which Thiel views as a distraction from actual technological progress.
Why This Matters for 2026 and Beyond
We’re seeing the birth of a parallel society. You've got the "Thiel-verse" for tech and finance, and the "Weiss-verse" for news and culture.
The deal between Weiss and David Ellison (son of Larry Ellison, another Thiel ally) to potentially bring her brand of "heterodoxy" to larger platforms like CBS News shows how far this influence is spreading. They are moving from the fringes of Substack to the heart of the legacy media they claim to despise.
Thiel told Weiss he’s "relieved" by the current political direction of the country. For the first time in a long time, the guy who thinks the future is a scary place seems to think his side is actually winning.
What You Should Do Next
If you want to track where this is going, stop looking at traditional political polls and start looking at where the "counter-elite" is investing.
- Watch the Boardrooms: Keep an eye on the funding rounds for new media companies. If you see names like 8VC or Andreessen, you're looking at the Weiss/Thiel orbit.
- Follow the Talent: See who is graduating from UATX and where they get hired. That will tell you if the "new elite" is actually sticking.
- Read Between the Lines: When Weiss interviews Thiel, pay attention to the "Russell conjugates" they use—how they reframe "populism" as "democracy" and "the establishment" as "the machine."
The era of the "un-canceled" media mogul is here, and whether you love them or hate them, Peter Thiel and Bari Weiss are the ones holding the blueprint.