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Bari Weiss, Substack’s Losses, and Mine
When one of Substack’s biggest stars cashes out, the rest of us have to pay the tab.
Confirmation just broke that Bari Weiss will be taking The Free Press to CBS, where she’ll become editor-in-chief of the news division.
That’s a lot to process: Weiss left the New York Times claiming to have been internally cancelled, The Free Press is a reactionary tabloid that doesn’t break news so much as try to shape it. There’s been a lot of good writing about What It All Means For Journalism (here, here, here, historical context here). As for what it means for The Free Press’s future on Substack—there’s been no reporting on it yet. Will the newsletter stay with Substack or migrate all its content and subscribers to CBS? I find it unlikely that CBS would pay $150M for Weiss’s operation and not want the subscriptions, which bring in (according to Weiss) about $10M/year.
If the Free Press leave Substack, it would be an enormous hit to the platform. Their 10 percent vig generates $1 million a year, representing roughly 2.5% of Substack’s total annual revenue (estimated around $40–45 million).
As a reminder: Substack has never turned a profit, and yet it’s still valued at $1 billion based on VC rounds. I’ve argued before in this newsletter that Substack cannot make money if it stays true to its promise of being a home for independent journalists wanting to preserve their voices. It’s a high-minded and laudable goal—one I’ve been seduced by myself, and one that has drawn many writers I deeply respect—but the business pressures don’t align with that vision.
Sooner or later the gravitational pull of investors will drag the platform toward something else entirely: the “YouTube of newsletters,” with all the churn, AI slop, engagement bait, and radicalization that implies.
Losing The Free Press wouldn’t just be a big financial hit; it would accelerate the enshittification.
The acquisition creates a roadmap for other major writers and publications on Substack to leave or create partnerships with traditional media organizations, now desperate for cred. We have seen this cycle (independent voices striking out on their own, establishing a new and popular media ecosystem, then being drafted back into the borg) before with blogging and podcasts. This is bad for Substack at the most macro level, losing the biggest puzzle pieces to make the profitability picture come together.
But the Free Press moving to CBS could come with a cruel twist for the smaller newsletter proprietors who hooked themselves into Substack because they believed the hype. Part of Substack’s “YouTube for newsletters” model that attracts some writers (despite everything that’s bad about YouTube) is its promise of discoverability. Being on the same platform as one of the heavy hitters is good for less prominent publishers (and Substack) because folks who come to the app to subscribe to the Free Press or Culture Study stick around and subscribe to a few others because they’re all Substacks, it’s one credit card bill, one portal.
Will the paying Free Press subscribers who get siphoned off to CBS keep their subscriptions to smaller newsletters? Will they stay engaged with Substack at all?
Boiling it down: The Free Press leaving will likely push Substack to make it harder to leave, even as it becomes a less profitable and less prestigious place for smaller publishers to be.
A Personal Note
I’ve been running into the precarity of the newsletter model myself. I got COVID in early September, which knocked me out for a while and slowed down production for this newsletter and freelancing, so my income took a hit.
And my friend Kaleb Horton died last weekend. I wrote a small piece on LinkedIn about his passing, because I want people who could have hired him to feel like pieces of shit. I may write more here. There is a newsletter angle—Kaleb was doing his best to make it work for him—because of course there fucking is.
On top of that, there have been some billing issues with this newsletter. If you’re a paying subscriber, you may want to check your records. I’ve already begun issuing refunds where I’ve found duplicate payments.
I’m in conversations with Buttondown (whose system generated the double charges) and other platforms as I decide whether to move off Buttondown. I will say that Substack’s payment system was reliable. My experience with a scrappy indie service is just more evidence of how difficult it is to maintain an operation as a truly independent journalist.
Thank you for your patience and your support. If you’re thinking of upgrading or renewing, I’d ask you to hold off until I get things a bit more stable.