Substack’s Founders Dive Headfirst Into the Culture Wars

One day last June, Patti Smith opened her laptop, typed a brief message to the thousands of readers of her Substack newsletter, and hit Send. “I would be grateful for any suggestions of songs you think I might try,” she wrote. “Have a good week-end!”

Smith began using the rapidly expanding, increasingly influential, and sometimes controversial email publishing platform in March 2021. Coronavirus had put touring on hold, and Smith was working on The Melting, a sort of diary about life in the COVID era, when someone at Substack reached out. Smith was intrigued. Rather than a pursuing printed work that she would n’t see the light of day for another year or two, she decided to publish The Melting on Substack in real time. She signed one of the company’s “pro” deals—the Substack equivalent of a book advance—and on March 31 sent out her first newsletter, offering readers a “journal of my private pandemic,” as well as “weekly ruminations, shards of poetry , music, and musings on whatever subject finds its way from thought to pen.”

Thirty-eight Substack emails later, Smith scrolled through the comments on her request for cover songs. One reader suggested “Pauper’s Dough” by the Scottish musician King Creosote, né Kenny Anderson. Smith found the track on YouTube, instantly falling in love with its slow, plaintive melody and lyrics that she described in a subsequent post as “a poem to the people, the salt of the earth.” She listened to it on repeat, memorizing the words and singing them as if they were her own. As luck would have it, Smith was due to perform in Anderson’s home country for the opening night of the COP 26 Climate Change Conference in Glasgow. Four months after discovering Anderson through her Ella Substack, Smith stood onstage with him in the darkness of Glasgow’s Theater Royal. “I just started crying,” she told me. “We sang the song together and it was very moving. That was a real Substack moment.”

Smith shared this story with me to convey her wholehearted embrace of Substack, which turns five this summer, half a decade after debuting with a promise to “accelerate the advent of what we are convinced will be a new golden age for publishing.” Since its founding, in tandem with an industry-wide pivot toward digital subscriptions, Substack has aggressively pursued that goal, making it both a darling of the media world and a breakout star of Silicon Valley. More recently, the company has found itself on the front lines of the culture wars. Its laissez-faire approach to content moderation, which sometimes gives voice to objectionable figures booted from other platforms, has made Substack a lightning rod in the debate over regulating free speech. But even amid bursts of negative media coverage, Substack has maintained a large and loyal user base, and there are no signs of an exodus.

Smith, for her part, sees her eponymous newsletter as a sort of petri dish for what the medium can be. In addition to her serialized memoir and other miscellaneous writings, Smith uses Substack for audio messages, poetry readings, and photography. She opens her laptop at night and records impromptu videos, inviting fans into her white-walled bedroom. In February, for Smith’s paying subscribers—$6 a month/$50 a year for unlimited access—she hosted a livestreamed performance from Electric Lady Studios, belting out classics like “Ghost Dance” and “Redondo Beach.”

In its early days, Substack primarily catered to a certain set of internet-savvy writers and journalists, lured by the promise of monetizing a direct relationship with their readers. But as it morphs from a niche publishing concern into a heavyweight start-up mentioned in the same breath as Twitter and Facebook, its user base is proliferating accordingly. “I really like my Instagram, but it has specific boundaries, and this was something new,” said Smith. “It makes me feel like, in the movies, where you see the reporter that goes to the phone booth and calls in her article. I feel a bit like that.”

A year and a half ago, in a column published in the pages of this magazine, I suggested that Substack “feels like a player that might just be on the cusp of the big leagues.” Since then, Substack has raised an additional $65 million in venture capital, bringing its total funding to $82.4 million—led by mega-firm Andreessen Horowitz—and its valuation to a reported $650 million. Its head count is about 90, up from 10 at the start of the pandemic. In November the company, headquartered in San Francisco’s Financial District, offered a tiny glimpse into its otherwise opaque revenues, saying it had surpassed a million paid subscriptions to Substack publications, the top 10 of which, out of hundreds of thousands, collectively bring in more than $20 million a year. (Substack typically skims off 10 percent of a newsletter’s revenue, but individual deals vary; some writers take a lump sum in exchange for relinquishing 85 percent of their subscription dollars.) In addition to Smith, several other literary lions have joined Substack (Salman Rushdie , George Saunders, Roxanne Gay, Chuck Palahniuk, Joyce Carol Oates), which has also begun to attract celebrities of varying stripes (Padma Lakshmi, Nick Offerman, Dan Rather, Edward Snowden, Kareem Abdul-Jabbar). In February, President Joe Biden bypassed the long queue of print reporters clamoring for a sit-down and offered one instead to Heather Cox Richardson, the breakout history professor who became Substack’s most-read writer last year. Substack also appears to have influenced strategy at major legacy news brands, like Atlantic and The New York Times, which have been building out their own newsletter portfolios and, in some cases, vying for talent with Substack. They’re not in Mark Zuckerberg territory just yet, but that appears to be the goal: Someone who’s friendly with cofounder Hamish McKenzie told me once he said that Substack would be the next Facebook.

When I asked McKenzie about that, he didn’t recall making the remark, but neither did he shy away from laying out the company’s ambitions. “We’re not here to build a small boutique business and just hope for the best, and hope that Google doesn’t crush us one day, or Amazon doesn’t crush us one day,” he said. “What we are trying to do is build a true alternative to the attention economy.”

McKenzie, a 40-year-old New Zealander who lives in San Francisco with his wife and two children, is Substack’s de facto ambassador to the media. Slim and clean-cut, McKenzie grew up in a rural wine and farming region, where his father worked as an atmospheric scientist and his mother a high school language and culture teacher. At the University of Otago in New Zealand’s southeast, McKenzie got into journalism, which brought him to Canada’s University of Western Ontario for graduate school. In 2006, I moved to Hong Kong and freelanced before helping create Hong Kong’s edition of Time Out. Two years later, he joined the American woman who would become his wife, Stephanie Wang, in the United States, eventually landing a reporting gig at PandoDaily, the now defunct technology news website. “He seemed very, like, ‘I wanna shake things up,’ ” remembers Paul Carr, Pando’s former editorial director. “You could tell he had big ideas.”

At Pando, McKenzie’s coverage of Tesla and SpaceX caught the attention of an editor who approached him about doing an Elon Musk book. Without a direct line to the elusive billionaire, McKenzie went to the personal website of Musk’s dietitian mother, found an email address for her son, and reached out, seeking advice on the best way to approach her son. “To my horror,” McKenzie recalls, “she just forwarded that email straight to Elon”—busted!—“and then Elon had his PR person call me right away.” Musk, as it happened, was familiar with McKenzie’s work and agreed to call him, except he was n’t keen on participating in a book. “Have you ever thought about going corporate?” I asked McKenzie, who met with Musk about a job at Tesla. McKenzie tried to talk Musk into doing a book anyway but got nowhere. He became a writer for Tesla’s communications team instead, sticking it out for more than a year before hearing the siren call of his Musk project, insanemode, which he left the company to write in 2015. Musk still didn’t participate, but McKenzie shared the manuscript prior to publication. “It wasn’t smooth sailing,” McKenzie told me.

While working on insanemode, McKenzie took a part-time job doing comms for the messaging app Kik, where he became friends with Chris Best, the company’s CTO. Best, a 34-year-old computer wonk who grew up outside Vancouver, had cofounded Kik in 2009 as he was finishing the systems design engineering program at the University of Waterloo in Ontario. In early 2017, Best left Kik and decided to take a year off. “I started writing,” he told me. “One of the things that had been swirling in my head was, like, Hey, I think our media ecosystem has gotten insane! And I wrote basically an essay or a blog post or something.” Best shared the piece with McKenzie and asked for feedback. “He was bemoaning the state of the world and how it led to this growing divide in society, and how the things that were being rewarded were cheap outrage and flame wars,” McKenzie recalls. “I was like, ‘Yeah, this is right, and everyone who works in media knows that these are the problems. But what no one knows is how to do something about it. What’s a better way? What’s a solution?’ ”

Their solution turned out to be Substack. “We were both readers of Stratechery,” Ben Thompson’s influential, largely paid newsletter about the business of tech and media, says McKenzie, “and we’re like, ‘Yes, the model does work really well. We’re both happy subscribers, paying subscribers to Stratechery. Why don’t more people try it?’… It was simple enough to be appealing and convincing to me that it was worth a shot.”

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