The Taste of Dirt

Daisy Alioto, a 33-year-old writer, editor and media executive, was looking at the 140 tons of dirt in the Earth Room, a permanent installation created by the conceptual artist Walter de Maria on the second floor of a loft in the SoHo neighborhood of Manhattan.

“It feels like a metaphor for what’s happening in media and culture right now,” she said. “Insisting on the value of something that the wealthiest people see as worthless or disposable.”

Ms. Alioto had suggested we meet there on a summer afternoon to discuss Dirt, the newsletter she has been running for the last few years. Operating largely outside the news cycle and social media discourse, Dirt has published essays on everything from broken heart valves to bad waitressing, from “yearning” to millennial gray.

There are also book reviews and interviews — anything, in other words, that Ms. Alioto and her small staff deem part of the “Dirtyverse,” their tongue-in-cheek name for the constellation of interests that fall within the company’s ambit.

Ms. Alioto’s sojourn to the De Maria sculpture had a winking air about it: the digital was paying tribute to a physical ancestor; Dirt was beholding dirt. And as it happened, Ms. Alioto was pulling double duty that afternoon, collecting material for an essay that included her thoughts on the Earth Room and the low-grade internet content known as “filler” or “slop.”

Multitasking is an everyday thing for Ms. Alioto. In her role as chief executive of Dirt Media, she edits stories, fields freelance pitches, talks to investors, and plans her new podcast, “Tasteland.”

“We’re scrappy,” she said while strolling through SoHo.

Ms. Alioto, who lives with her husband in Peekskill, N.Y., but travels regularly to her family’s home in Maine, was wearing a brown hat with the word “DIRT” emblazoned across it in mint-green lettering. She also wore a brown skirt and a green-striped button-up: She was on brand.

In addition to Ms. Alioto, three people are on the newsletter’s staff, all of them working remotely — an editorial fellow, a community manager and Tyler Watamanuk, whose design-focused newsletter, Sitting Pretty, was acquired by Dirt last year and reintroduced as Prune.

“Maybe 10 years ago you were trying to sell a book,” said Mr. Watamanuk, who lives in the Hudson Valley. “Now you’re trying to sell a newsletter.”

It’s not often that a media company of Dirt’s size purchases another. But Ms. Alioto hopes to add many newsletters to Dirt Media, saying she wants Dirt to become “the Condé Nast of newsletters” or “the LVMH of media.”

The Condé Nast comparison comes as the magazine empire, like many other traditional publishers, has instituted layoffs and struggled to bring in digital ad revenue. But while others in the industry may be given to media doomerism, Ms. Alioto takes a more levelheaded view.

“To the extent that I look back, it’s to really embrace the power of magazine culture, the power of aspiration, the way people want to see their lifestyles reflected in the media that they consume,” Ms. Alioto said, as she settled into a mustard-yellow table outside a Drybar in SoHo. “I think everyone’s pretty nostalgic for the town car era of Condé Nast, but it’s not coming back.”

Born in Massachusetts, Ms. Alioto attended Bowdoin College in Maine, where she started a blog called In the ‘Cac, a reference to the New England Small College Athletic Conference, and made friends and contacts she continues to draw on. (David Alderman, the designer of the ‘Cac branding, also designed Dirt’s logo.)

Internships at Elle  and NPR followed, then jobs in audience development for design and watch magazines, as well as freelance writing gigs and a stint at The New York Review of Books. She was laid off during the pandemic and wrote about the experience for Dirt: “If this year has taught us anything, it’s that you have to know when you’re not the little guy anymore — I certainly hope that I will recognize that power in myself, when the time comes.”

Dirt began life as a Substack created by Kyle Chayka, who wanted to establish a place to publish pieces on “the random observation you can’t stop thinking about,” as Mr. Chayka put it in an interview. He asked Ms. Alioto, who had moved on to freelance consulting for Airmail, the Graydon Carter newsletter, to come aboard as co-founder. A year later, they incorporated Dirt Media.

The two had earlier met through Study Hall, a freelance resource Mr. Chayka co-founded, and had been talking for years “how we were dissatisfied with digital publishing in general,” he said. (Mr. Chayka stepped back from day-to-day operations at Dirt in 2022 to focus on a book and his job at The New Yorker, where he is a staff writer. He retains a stake in the company.)

Their first post began with a tone-setting question: “Don’t you wish you had a place to talk about stupid things?” A five-part series on the television show “Industry” followed, analyzing the program’s intro logo and “banker babble.”

Dirt arrived during a wider newsletter boom, but Ms. Alioto and Mr. Chayka had an offbeat proposition. They wanted to hitch their new venture to cryptocurrency and began funding the site by auctioning off custom NFTs. By the end of 2022, they had raised $1.2 million in seed capital, much of it from investors bullish on the blockchain and fluent in its language (what a Dirt writer might affectionately call “Bitcoin babble”).

When Dirt migrated to its own website in 2023 and opened paid subscriptions, readers could pay only in Ethereum, which proved challenging for some.

“I tried to subscribe when you had to do it through Ethereum and couldn’t figure it out, so Daisy had to give me a hand” said Neil Janowitz, the editor in chief of Vulture.

These days, words like “minting,” “wallet” and “DAO” appear on Dirt  less frequently, and crypto has become less central to its business model. The company now accepts credit cards for its subscriptions ($60), which has helped Dirt bring in between 30,000 and 40,000 subscribers, Ms. Alioto said.

“If we’re sticking around, if we’re doing good work, if we’re paying writers a fair rate — people kind of accept that this is part of the company, this is part of how the company was funded,” she said of its involvement with crypto.

Whether Dirt would stick around wasn’t always clear. At first, Ms. Alioto and Mr. Chayka released the newsletter in “seasons,” partly to account for their uncertainty.

“We did this crowdfunding, we got a lump sum, and there was no guarantee that there was going to be another season,” Ms. Alioto remembered. That format was “a way of giving things a natural endpoint.”

Through Dirt’s evolutions, Ms. Alioto has tried to maintain the newsletter and its extended brand universe as “containers for taste,” a phrase she used in an essay last year to describe the role magazines once played and media perhaps still should. She argued that, in a world drowning in throwaway content, taste — not simply “good” or “bad,” per se, but rather cultivated and communicable — will soon be one of the only things that can be monetized.

“Within five years, nobody will be looking for the next MrBeast, they will be looking for the next Tina Brown,” Ms. Alioto wrote, referring to the era-defining editor who shaped Vanity Fair in the ’80s and remade The New Yorker in the ’90s.

For regular readers of Dirt, the newsletter may at times seem particular to one woman’s idiosyncratic tastes: Ms. Alioto’s. But it takes input from its readers on what it publishes: Subscribers who purchase a Founder’s Pass (about 0.5 Ethereum) can influence certain editorial decisions by voting to greenlight one of several story ideas. Dirt fans can also dig deeper into the Dirtyverse on Discord, where they can share interests and discuss recent articles.

As much as it covers lifestyle, Dirt also tries to foster one around its own branding, selling bracelets, zines, perfumes and, recently, offering a free digital tarot deck.

Jonny Diamond, the editor in chief of Lit Hub, said in an email that he had taken notice of Ms. Alioto’s marketing savvy: “I share a lot of Daisy’s opinions about what it takes to maintain a successful media venture: the importance of a defined personality with a particular set of editorial tastes, the cultivation of a dedicated return readership (rather than a giant, random, unreliable ‘audience’ fueled by virality), a diverse set of revenue streams beyond the Web 2.0 ad model (which privileges volume over quality), and, yes, hats.”

“There will be Lit Hub hats next year,” he added.

But for all of Ms. Alioto’s ambitions to emulate a giant like Condé Nast, she has won over readers — and earned street cred in the industry — with her hat tip to the D.I.Y. blogging era, when little-known writers could get their first clips a bit more easily and writing for the internet was voicey and whimsical.

“I think everybody has acknowledged that there’s a shift back toward blogging and voice and perspective that’s occurring,” Mr. Janowitz, Vulture’s top editor, said. He added that Dirt’s willingness to take a risk on younger writers enabled the rest of the industry to learn about those writers and give them more opportunities.

Daniel Spielberger, an occasional Dirt contributor and the executive editor of Study Hall, said Dirt belonged in a lineage of websites including Gawker, The Awl and Real Life Mag, which continue to be mourned years after they shut down. Those sites were places for “writers to experiment,” he said.

“Because you’re tapped in, and because you’re working with a smaller team, you can just hit on new ideas early and be the publication that signal-boosts them to the wider online sphere,” said Walden Green, 21, an editorial fellow at Dirt, who wrote about “heirloom chic” for the newsletter.

With its sometimes esoteric essays, Dirt might capture readers of magazines like The Paris Review or Harper’s. But it has also caught the attention of tech and finance readers who may be drawn in by its posts on Gen Z venture capitalists or meme coins.

“Often when people say they are at the intersection of tech and culture, it’s quite lame,” said Dani Loftus, the founder of DRAUP, a digital fashion company, and the author of the meme coin essay. “Daisy has made a publication that’s actually cool.”

Ms. Alioto herself writes as capably about software as she does about Joe Brainard or the recent eclipse. But, she says, she is “not a technology-for-technology’s sake person or a hyper-futurist or trying to go to Mars.”

“My motivation for being future-forward comes from a place of: We just can’t lie down and admit defeat.”