The Bari Weiss Strategy

There’s a really important lesson in this Bari Weiss acquisition.

On October 6, Paramount announced its acquisition of The Free Press for approximately $150 million. Notably, Weiss will also serve as Editor in Chief of CBS News. On one level, the story is obviously validating from our perspective as independent scholars. But what's interesting to me is that this playbook is probably quite reproducible, although none of these rules are written down anywhere…

The goal is not to build a particularly successful or sustainable business, or to generate the biggest return for investors. The goal is to build an operation that is sufficiently serious, focused, and professional—at a level comparable to legacy institutions, without needing to be as big or profitable or successful—such that you are the only serious choice when big money eventually comes in to resuscitate a dying heritage brand.

The acquisition follows the August 2025 merger of Skydance Media and Paramount Global, which put David Ellison, son of Larry Ellison, in charge. Essentially, a budding media tycoon acquires a languishing legacy media brand and needs fresh blood to update it for the 21st century. Where do you think he's going to look? He'll choose the most professional and successful indie-media operation that pattern matches with his vision.

The story starts back in July 2020, when Weiss departed The New York Times. In January 2021, she launched a Substack called Common Sense, which evolved into The Free Press in December of 2022—a full-fledged news organization co-founded with her wife, Nellie Bowles, and sister, Suzy Weiss. Operating like a traditional newsroom but with a common-sense perspective against all the left-wing fashions, The Free Press tackled a range of issues.

It was never particularly provocative in any direction; it was a bet on normal American attitudes, a bet that the excessive left-wing fashions were a temporary disequilibrium and that the market would correct. By 2025, Weiss's hard work had led to a staff of over 50 people and a readership of 1.5M, including over 170k paying subscribers. This week, the market corrected.

Weiss's politics and style are noteworthy here. While in several dimensions she took big risks, and all the credit to her, in other dimensions her tremendous success seems rooted in minimizing risk as ruthlessly as possible. Despite leaving the NYT she never stopped presenting herself as an eminently safe, nice, reasonable, secular, modern, and respectable individual. Though a proud defender of Israel, she is basically just casual and moderate on everything else. Who else checks all the boxes a David Ellison would need checked?

Financially, it would seem the $150M sale price is an unreasonable multiple on the company's annual revenue of ~$18M, but this is only proof that brand can be worth a massive premium.

For investors, this was not a particularly successful outcome. The 2024 Series A round raised $15 million on a $100 million valuation, so this result will not move the needle in any of their portfolios. Yet I'm sure most of those investors are quite happy with this result, as some of them seem to be on Twitter, which really just proves that there is a whole other non-financial game that exists within the VC game. They are willing to back serious operators trying to change the culture, and even if you don't produce a meaningful return, there are other ways you can win (even in their eyes).

If you study the startup scene, nothing will suggest this pathway is possible. No YouTube videos will tell you that this path is open to you. But it is, and this playbook is probably not limited to the news sector. You could probably do it for any vertical where the legacy brands are obviously toast. Very few could pull it off simply because it's hard, but if you have what it takes, it seems there for the taking. Just call your shot and build a serious, respectable operation to become the only possible choice for whoever comes in to resuscitate the biggest legacy brand in that vertical.

While this is undoubtedly a personal triumph for Weiss and an impressive "revenge arc," from at least one perspective it is arguably bearish from the indie scholar perspective. Personally, I think real escape velocity for independent culture will be most clearly proven when the next Bari Weiss says "no thank you" to a $150M offer. This acquisition could be seen as a kind of recuperation of the independent spirit back into a dead institution, where perhaps they will all just continue to die. Will The Free Press simply be absorbed into Boomer Death? I wish them nothing but the best, though my more anarchist temperament (and the lessons of history) feel somewhat more pessimistic on this question.

But the point is that I think this playbook is eminently repeatable, and I hope we see a new wave of ambitious independent operators running it back across all the other cultural verticals in need of it. I wanted to jot down these notes because I feel like this lesson, though quite legible, perhaps even obvious, is still mostly unwritten.