“People Are Looking to Latch Onto Something Positive”: As Journalists Flock to Substack, Is There a Limit to the Newsletter Boom?

Pop Culture

Between the collapse of newspapers, the misfortunes of digital media, and the economic wreckage of the coronavirus pandemic, writing for a living can feel like a cold, dreary, morale-sucking march to the unemployment office. And yet, there’s a hopeful sentiment heard lately in journalist circles: It feels like the beginning of the gold rush.

That gold rush is Substack, and the man handing out pickaxes is a 33-year-old Silicon Valley techie named Chris Best, who serves as CEO of the au courant publishing platform for email newsletter scribes. Substack newsletters are growing in influence and numbers, and in many cases, they’re becoming a no-brainer for marquee writers and reporters who want to make a comfortable salary—quite possibly a very comfortable one—without having a boss. “If we succeed in our ambitions,” Best told me, “one of the things we hope is that this is a better model than the way things work now.”

Substack’s thousands of writers span left and right, conventional and contrarian, old media and new. It’s got reporters, academics, talking heads, political strategists, finance wonks, Christians, controversials, and crypto enthusiasts. To date, there are more than 250,000 subscriptions across the network. At the top of the ladder, tens of thousands of people pay $5 a month to read A-listers like Matt Taibbi and Andrew Sullivan or breakthrough historian Heather Cox Richardson.

Lefties flock to Judd Legum’s Popular Information and right-wingers to Erick Erickson’s Confessions of a Political Junkie. When Glenn Greenwald recently stormed out of The Intercept with guns blazing, Substack was his obvious landing pad. Remember Mark Halperin, whose lucrative journalism career came to a screeching halt during the #MeToo movement? He’s a Substacker now too. Click a button and you can fill your inbox with dispatches from the likes of former Obama adviser Dan Pfeiffer, China expert Bill Bishop, sociologist Zeynep Tufekci, advice guru Heather Havrilesky, economist-cum-parenting expert-cum-soothing COVID-19 researcher Emily Oster, and many more. (Oster’s newsletter is among a subset of free ones.)

“It was just the right time,” said Anne Helen Petersen, who left her job as a senior culture writer at BuzzFeed in August to focus full-time on a Substack newsletter. There were several factors in the decision, she said, from “the precariousness of digital media over the course of the pandemic” to wanting more creative freedom and writing without the burdens of gaming headlines to play on social media. Still, to get Petersen over the finish line, the Substack brass agreed to cover her health insurance and the hiring of a features editor. She took a lump payment for the first year (she declined to say how much) and agreed to let Substack keep 85 percent of her subscriber revenue. Other writers take no money up front and keep 90 percent of what subscribers pay at a variety of rates. (It could be $5 or $7 a month, $50 or $60 a year, and so on.) The made-for-dummies user interface makes the whole experience pretty seamless. As Petersen put it, the writers joining Substack are “regaining control of our own journalism.”

The company, which was incubated by Y Combinator in 2017 before raising $15.3 million last year in a Series A round led by venture capital firm Andreessen Horowitz, remains relatively small. As of this fall there were 18 employees, including Best’s two cofounders, Hamish McKenzie (COO) and Jairaj Sethi (CTO). They don’t have an office yet (COVID put those plans on hold), and there’s still a scrappy teamwork ethos when it comes to handling the laborious stuff, like customer service. But between the buzz and the metastasizing roster of brand-name bylines, Substack feels like a player that might just be on the cusp of the big leagues. “They are the great white hope of media right now,” said Om Malik, a partner at True Ventures. “People are looking to latch onto something positive. There isn’t much positive left.”

When Substack launched in July 2017, McKenzie published an essay likening it to the penny newspapers that sprouted up in Victorian America, revolutionizing the industry with their dirt-cheap newsstand price and cornucopia of ads. “Benjamin Day radically altered the future of journalism with a tweak to its funding model,” McKenzie wrote, referring to the publisher of the original New York Sun. “Almost two centuries later, the news industry is ready for another reinvention.”

Best leaned in to that analogy when we video-chatted in late September. He was in San Francisco, where he lives with his wife and almost-one-year-old. “I don’t think we aspire to just be on par with traditional publishing,” said the neatly bearded founder, looking very start-up casual in a plain gray T-shirt. “I think we can be something bigger and more important. It sounds ridiculously grandiose, but we are setting out to make something that is better than what came before.” Is there another fundraising round on the horizon? “We’re in a position where if we never raised money again, we could comfortably become profitable and grow at the same rate.” What about a future sale? “Our ambition is to become a successful independent company.” (McKenzie poured cold water on media columnist Ben Smith’s reporting about internal discussions regarding a potential Twitter acquisition: “We are not interested in being acquired by Twitter. We believe that such a move would be a breach of the trust that writers have placed in Substack.”) I asked Best for an example of some moment when it really started to feel like this thing was catching fire. “Doing customer support,” he said, “there have been numerous times when I realize I’m talking to someone that’s more famous than I ever imagined I’d be talking to.” (He was too polite to name names.)

As far as millennial CEOs go, Best’s name recognition is somewhere between a person you’ve never heard of and, say, a Kevin Systrom or Evan Spiegel. He grew up outside Vancouver and studied systems design engineering at the University of Waterloo in Ontario. There, he and several classmates created the smartphone messaging app Kik, where Sethi, a fellow Waterloo alum, worked as a developer, and McKenzie, a New Zealand-born former tech reporter, joined as an editorial adviser. The trio broke away from Kik in 2017 and then, poof: Substack.

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