• New York magazine is leaning into pop-up newsletters as part of an effort to diversify its business.
• It's planning to launch 15 this year, up from nine last year.
• The company says pop-up newsletters promote reader retention and interaction.

At New York magazine, commas can cause big drama.

That's one tidbit readers have learned from Queries, a pop-up newsletter written by the publication's copy chief, Carl Rosen. Twice a year, Rosen holds forth on topics like when to use commas and throws occasional shade at other publications' copy desks. Started on a hunch, Queries has become one of New York mag's most popular newsletters. It's even spawned a line of merch like ball caps and T-shirts bearing the word "iconic" (IFKYK).

Rosen told Business Insider he had been surprised by the size of the audience of "nerd-out grammar freaks."

"Everyone's looking for certainty," he said. "People want to know all these basic style points."

"One reason our readers enjoy the column is, when they read it, they know how much I care about this, and we all do about everything we do," he added.

Queries is part of a growing push by New York into newsletters that publish for a defined period, usually a few weeks. New York had nine subscriber-only pop-up newsletters in 2024; this year, it's aiming for about 15. They also fit into a broader newsletter effort by New York's parent company, Vox Media. Newsletters that cater to readers' passions are one way Vox is trying to build direct audiences and diversify revenue in the face of advertising and subscriber headwinds.

Three new pop-ups this winter cater to people who want to go deep on the new seasons of "Severance" or "White Lotus" (starting February 17). Some earlier ones were focused on book readers and holiday shopping. This year, New York is also launching New York Night School, a series of six newsletter-based courses for subscribers by its writers and editors.

Finding passion points

New York has 115,000 unique subscribers for its eight current subscriber-only newsletters, out of 1 million subscribers to all its roughly 40 newsletters.

The publication says readers of its subscriber-only newsletters are almost 40% more likely to stick around than other subscribers. That comes at a time when many publishers are focusing on building and retaining their subscriber bases in the face of traffic challenges. New York declined to share its total subscription number.

"Keeping a subscriber is a lot less expensive than acquiring a new one," said Priyanka Arya, SVP and head of consumer revenue at Vox Media. "And it's healthier long-term revenue that you've locked in that you want to continue to renew and grow. So that's a big focus for us."

New York says its pop-up newsletters consistently get a unique open rate of 70% (meaning multiple opens by a unique subscriber are counted as one), compared to about 50% for its newsletters overall. It could help that the pop-ups are finite, which adds a scarcity element.

Dan Oshinsky, a media consultant who runs Inbox Collective, said that among media newsletters, open rates of 40% to 60% are common, depending on the publication and the audience. He added that open rates for short-run newsletters like pop-ups can be as high as 80%.

One of the challenges for New York's pop-ups is finding new interests to tackle. Some of the pop-ups have come out of seeing what topics people read and comment on most, like TV recaps, or are specifically focused on passions or interest groups the magazine wants to target. Others, like Queries, were based on intuition.

New York mag wants these newsletters to make readers feel like they're talking to a bunch of people in the newsroom. One popular one featured the magazine's art critic, Jerry Saltz, talking about his favorite books and podcasts. For its TV-watching newsletters, New York mag has enlisted people from across the newsroom. For example, a staffer from its real estate vertical Curbed wrote about art and design in the "Severance" office.

"We just slice it and dice it in different ways and try and pinpoint a couple small things from each episode," Kaitlin Jessing-Butz, newsletters director of New York magazine, said of the TV-focused newsletters.

This distributed approach to producing the newsletters helps Jessing-Butz, who has a small staff, spread the workload across the newsroom. It's also a way to expose readers to different parts of the publication. People who read multiple sections tend to renew at a higher rate than people who read just one, New York said.

Interaction is another feature of the newsletters. Queries has offered readers a grammar quiz, while the book club newsletter has invited them to vote on what to read next. For the "Succession" TV pop-up, New York had a live chat with readers to discuss the show's finale.

A shift to evergreen newsletters

Night School is the newest addition to New York's pop-up newsletters. A handful of other publishers, like The Wall Street Journal and The New York Times, have previously tried course-style newsletters. The Journal, for example, is offering six this year — around various financial and fitness challenges — as part of its efforts to promote engagement with readers.

The first in New York mag's Night School is called "How to Write." It's overseen by executive editor Genevieve Smith with participation from writers and editors like Lane Brown and Emily Gould. It includes a syllabus and invites readers to submit questions and feedback.

The next one, called "How to Be a New Yorker," will offer hacks to survive the city and have a print component as well.

"The idea with the course is to me is we're going to teach our subscribers the things we know best, and that is definitely one of them," Jessing-Butz said.

These courses represent a shift in New York mag's newsletter strategy. More so than some of its pop-ups, these courses are designed to stick around so that they can be marketed to new subscribers. Subscribers can sign up for past schools and move through them in whatever order they want.

"Having an evergreen format makes a lot of sense for us, where, no matter when you subscribe, you can sign up for one of these night courses," Arya said.