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Exclusive: Dirt Media acquires design newsletter Sitting Pretty

Oct 2, 2023
Illustration of a fountain pen with a pixelated paper airplane as the nib.

Illustration: Aïda Amer/Axios

Dirt Media has made its first acquisition with Tyler Watamanuk's design newsletter, Sitting Pretty, CEO Daisy Alioto exclusively tells Axios.

Why it matters: Newsletters have served as effective launchpads for new media companies and independent writers. Dirt is pursuing a bundling strategy with eyes on acquiring and launching more newsletters.

How it works: The transaction allows an independent writer to grow their craft without the stress of managing a media business, and boosts the readership and coverage scope of a media startup.

Catch up quick: Dirt raised $1.2 million in 2022. It's working with Trellis Literary Management on its first book and recently signed with WME for TV, film, podcasts and more.

  • Watamanuk launched Sitting Pretty as a newsletter in 2021 after writing a column of the same name for the now-defunct publication Garage. He previously published on Facebook's Bulletin and then moved to Substack.

Details: Alioto says the deal is a mix of cash and equity and a retainer for Watamanuk, who joins Dirt as senior writer and contributing editor, Prune. The company did not disclose financial details of the transaction.

  • Sitting Pretty is rebranding as Prune, a weekly newsletter about interiors, design and more. Dirt will add a "Design" category to its website, which will include Watamanuk's archive.
  • Prune will launch Discord channels to discuss design. It also made a playlist and 30 limited-edition zines about the on-screen interiors of director Mike Mills. It plans to create merchandise.
  • "Dirt immediately made an impression on me as a reader because they were publishing essays you couldn't read anywhere else," Watamanuk says. "Daisy is really savvy when it comes to being on the cutting edge of internet publishing, and I frankly just want to write about Eames chairs."

Of note: Alioto says she has long been a fan of Watamanuk. She edited his newsletter last year, and he has written for Dirt, including about Nora Ephron's interiors.

  • Acquisition talks began in late 2022 and were confirmed via a handshake over falafel in Rhinebeck, New York, this past August, Alioto says.

What's next: Dirt plans to launch three other verticals over the next 18 months from acquisitions and internal incubation, Alioto says, but is interested in more.

  • "Dirt Media is open for business," Alioto wrote in an editor's letter Monday. "Want to sell us your newsletter? Bang my line."
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