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FWD Progress

Digging Into ‘Dirt,’ a Digital Entertainment Newsletter

While paid newsletter tiers are common, Dirt is among the first to finance its operations through NFT sales. 

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Welcome to a new Inbox Collective series, FWD Progress. Here, we spotlight newsletters innovating the form in one way or another (like content, monetization, or community), and explore the nuts and bolts of their strategy. To kick things off, we have Dirt, the cult digital entertainment newsletter that’s partly funded by sales of non-fungible tokens (NFTs).

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What Is Dirt?

Dirt is a daily newsletter that examines streaming content and internet culture through a hyperintellectual lens. Each email features an essay written by a freelance critic along with a short roundup of news and recommendations links. Popular essay topics have included TikTok’s obsession with 2000s suburbia, the meme-ification of New York neighborhoods, and why year end-lists are “vacuous grounds for bragging.” Dirt was initially funded by sales of NFTs purchased on the Ethereum blockchain (don’t worry, we’re going to explain this) before taking outside funding in 2022.

Launched: December 2020

Subscribers: 18,000

Platform: Substack

Founders: Kyle Chayka, a contributing writer for The New Yorker who focuses on technology and internet culture. 

Daisy Alioto, a writer and critic who also has worked in audience engagement. 

How It Started

Chayka had the idea for a newsletter that covered online streaming and entertainment during lockdown when the world’s collective screen time was at-all time high. “I felt like everyone was watching TV all the time, looking at TikTok, and consuming multimedia content,” he says. “So I thought a daily newsletter would be a really good format to address that because every day people were like, ‘What should I watch? What are you watching?’” He proposed the idea to Alioto (whose clear-eyed writing on digital culture he admired) and she agreed to come on board.

How It’s Going

To hear Chayka tell it, he didn’t set out to make Dirt a business: “I just thought, ‘This idea is super cool. Maybe it could be a publication that people would like.’” But as he ventured deeper into the world of Web3 through his other work as a journalist, an idea began to crystallize: “I realized that… if this market is blowing up, if this is the new wave of the internet, then maybe Dirt should use it as a business model and not just cover it.”

In June 2021, Dirt launched its first NFT, a depiction of its mascot, Dirty, on the crypto platform Mirror. 131 NFTs sold in a week for over $33,000. (Mirror received a small percentage of the sales.) “It’s a proof of concept that NFTs alone could fund a small media company,” Chayka told Axios at the time. Indeed, after that initial drop, Dirt was able to cover their freelance budget and hire some part-time staffers. They’ve produced three subsequent NFT waves (varying in cost), including a drop of mushroom art and, most recently, a series of bi-monthly artist collaborations with the likes of Mike Varley and Kyle Knapp. However, these were open only to existing NFT holders. Last year, Adweek reported that Dirt earned roughly $90,000 from NFT sales alone. 

On the cutting edge of commerce and content

While paid newsletter tiers are common, Dirt is among the first to finance its operations through NFT sales. 

Beyond bringing in money –– after Dirt exchanges ether back into dollars –– the NFTs also function as their own membership tier with special rights and privileges. Readers who buy an NFT receive a “$DIRT” token that grants participation in the DirtDAO as long as they hold it. Popular in Web3 circles, a DAO, or Decentralized Autonomous Organization, is an entity governed by members who purchase a designated token. In essence, it’s a club with certain perks and the only way in is via the blockchain. 

Launched in January 2022, Dirt’s DAOcurrently counts around 150 members. The biggest perk? Voting rights on the newsletter’s feature pitches. In other words, members collectively determine which longform stories Dirt commissions and publishes. They also enjoy exclusive access to a Discord channel where they discuss editorial decisions and a monthly newsletter that highlights the work of various DAO members. Meanwhile, the DirtDAO FAQ page mentions the possibility of expanding future voting to decisions around events, NFTs, and product development.  

“To me, the DirtDAO is kind of like an editorial board,” says Chayka. It’s also a pretty strategy to keep Dirt’s superfans engaged. Members retain their stake in the DAO unless they sell their NFTs, and unloading an NFT in the secondary market isn’t always easy. 

Dirt’s ahead-of-the-curve instincts extend to its content. It covers percolating online trends and niche subgenres with analytical rigor, like an #extremelyonline Susan Sontag. You would be hard-pressed to find a piece like the one Terry Nguyen recently wrote on the aesthetic of bookishness or Claire L. Evans’s ode to pre-PowerPoint presentations anywhere else on the internet. 

Of course, the need to make sense of pop culture within the larger context of modern life is hardly new. But Dirt is pioneering applying critical frameworks to the TikTok era. “We try to be smart but not pretentious,” says Chayka. He notes that the newsletter resonated with readers as soon as it launched. “I was like, ‘Oh, cool… I was correct in thinking people wanted something like this.’”

What’s next

In the summer of 2022, Dirt took a $1.2 million seed round from bullish crypto investors like Collab+Currency and Unicorn DAO. The goal, according to Chayka, is to build a full-scale blockchain-based media company that includes a website, an NFT platform, and as-yet-unspecified proprietary technology. 

Working with crypto isn’t for the faint of heart. “Volatility is definitely something we’ll have to deal with,” Chayka says,”But we will vary our prices in ETH [ether, the cryptocurrency on the Ethereum blockchain] to ensure the appropriate levels of funding.”  

He also isn’t concerned that a membership tier that requires a working knowledge of NFTs and cryptocurrencies (not to mention, Web3 accouterments like a crypto wallet) presents a high barrier to entry. You can sign up for the free Substack newsletter, but there is currently no paid tier outside of NFTs.

“Dirt’s goal is to bring more people into the space of Web3, so we’re hoping to encourage readers who don’t know anything about it to jump in and experiment,” Chayka says, noting that the free newsletter tier will always be an option for the crypto-averse. 

Besides, says Chayka, a Web3 media company, at least as he envisions it, isn’t just defined by the technological infrastructure. It’s also about solving for how, in the age of news avoidance, distrust, and competition from social platforms, a publication can build a better relationship with its audience. “More constructive, more positive, more intimate,” he says. “And I think that’s a question every media company is asking itself right now.” 

Correction: This story originally misspelled the names of Dirt co-founder Daisy Alioto and senior writer Terry Nguyen. It was updated on 12/15/22 at 1:10pm. We sincerely regret the errors.

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By Evelyn Crowley

Evelyn runs a content and brand strategy consultancy where she helps clients find their voice and build their community. She works frequently on newsletter projects and specializes in building and launching concepts from scratch. She's based in Austin, Texas. Her favorite email sign off is “Please pretend this made sense.”