Peak Newsletter? Even the Biggest Stars are Feeling the Squeeze

“Newsletters are cooked,” says Taylor Lorenz, whose own User Mag newsletter boasts 97,000 total subscribers. Two years ago, Lorenz left her high-profile job as a columnist at The Washington Post for what she described then as the “complete autonomy” of reaching her audience directly in their email inboxes. But she says she’s lost a third of her paid subscribers in the past several months, and she predicts an AI-driven extinction event. “I don’t think we’re going to be reading email newsletters in five years,” Lorenz says.

This sounds shocking when you consider that nearly every day someone — a TV news anchor, a politico, a musician — makes media headlines by launching a newsletter. That the form has made superstars out of writers like Emily Sundberg and Heather Cox Richardson. That it has become the backbone of multi-million dollar new businesses, from The Free Press to Puck to of course, yes, The Ankler. But as AI agents come for our email inboxes and subscription fatigue sets in among cash-strapped consumers, many people who make a living on the format have started to wonder how long the good times — and those monthly subscription fees — can keep rolling.

“It’s gotten way harder” to grow subscribers, confides one journalist with a top Substack publication. Another writer with a very popular newsletter speculates that the industry has hit a “subscriber saturation point, and the reason people are freaking out is because we can’t conceive of a publication as successful if it isn’t constantly growing.”

Can it really be that bad? Not everyone thinks so. “There are still a lot of success stories,” says Dan Oshinsky, who runs the email consultancy Inbox Collective. “From what I’m seeing, we’re certainly not at any sort of peak newsletter.” It’s true, there haven’t been any recent pullbacks in the space, a hallmark of the last time newsletters were declared past their peak. And in just the last few weeks, several high-profile new entrants — among them Piers Morgan’s Uncensored and Bill Simmons’ The Ringer — made a bull case for newsletters as a tool for audience acquisition.

Interviews with a half dozen newsletter writers, including Lorenz and Breaker Media’s Lachlan Cartwright, as well as Substack co-founder Hamish McKenzie, Beehiiv CEO Tyler Denk and other media executives reveal optimism about the future of newsletters. But these players also paint a picture of a business once seen as a silver bullet for independent media that’s now grappling with the same challenges as the rest of the industry.

Subscriber growth is getting harder, churn is relentless and platforms are increasingly competing for the writers who helped fuel the newsletter gold rush in the first place.

But here’s the twist: While some of the biggest names are losing subscribers, others are having their most profitable months ever. Platforms are offering financial guarantees to lure writers away from rivals. And as AI threatens to change how we use our inboxes altogether, a new playbook for success is emerging.

So who’s winning, who’s losing — and what happens when the newsletter itself is no longer enough?