How the subscription newsletter service Substack is changing the writing game

One of the great surprises of the COVID-19 era is that some of the most talked-about journalism on the internet is being done through a subscription newsletter service. And, more surprising still, this business model is actually proving to be profitable. I’m speaking, of course, about Substack, a platform that’s gained prominence during the pandemic as a haven for heterodox journalists exiting the mainstream media.

The platform is now home to investigative reporters such as Matt Taibbi, formerly of Rolling Stone, and Glenn Greenwald, a founder of The Intercept; digital media heavyweights such as Vox’s Matt Yglesias; and former magazine columnists such as New York’s Andrew Sullivan. All have concerns about the direction the media is headed, and all now regularly publish pieces that it would be hard to imagine reading at their former outlets. As such, Substack has become something of a referendum on contemporary journalism and, due to the controversy surrounding many of its personalities, a contested development.

Substack (which has a Canadian co-founder) is basically just a newsletter that arrives in your e-mail inbox. The tone, length and style of posts is reminiscent of early-aughts blogs, with authors spending thousands of words mulling over topical issues. There are Substacks on every conceivable subject, but the ones that generate headlines tend to be written by contrarian journalists, mainly classic liberals who champion free speech and a free press. Readers can subscribe for free, but can only gain access to all of a creator’s content by paying a fee – typically around US$5 a month, of which Substack take a 10-per-cent cut.

It’s a way of following, and supporting, journalism you like. And it’s proving very popular.

The question for many watching this cultural phenomenon unfold is: Why would journalists at the height of their careers decamp to a relatively new, and relatively small, platform? And why would readers follow them there – and pay generously for their work? What are readers getting at Substack that they can’t get elsewhere?

To talk about the Substack phenomenon, then, we have to talk about the media. And to do that, we must contemplate the criticisms of its high-profile dissenters.

Bari Weiss left The New York Times in the summer of 2020, with a widely circulated resignation letter that charged the paper with failing to learn the lessons of the 2016 election – “lessons about the importance of understanding other Americans, the necessity of resisting tribalism, and the centrality of the free exchange of ideas to a democratic society.” She argued the paper had become a performance space for predetermined narratives, with Twitter acting as its ultimate editor. “A new consensus has emerged in the press, but perhaps especially at this paper: that truth isn’t a process of collective discovery, but an orthodoxy already known to an enlightened few whose job is to inform everyone else.”

As Weiss sees it, the spectrum of acceptable opinion at the Times has narrowed to the point that it no longer represents the spectrum of the country. “Stories that are inconvenient to the progressive political project are overlooked or ignored or explained away,” she tells The Globe. “And I think that is doing an incredible disservice to readers.”

She had been hired to increase the intellectual diversity of the Times’s opinion section, bringing in first-time writers, libertarians, conservatives and centrists, including Thomas Chatterton Williams, Randall Kennedy, Glenn Loury, Ayaan Hirsi Ali, Wesley Yang and Chloé Valdary. But, Weiss says, “getting pieces through on topics that touched anything that was considered third rail – and there were an increasing number of topics that were considered third rail – was incredibly taxing.” Every incentive, she says, worked against doing the job she was hired to do.

“Fear of outrage mobs is what drives a lot of corporate decision making in a way that’s incredibly disturbing,” she adds. “In the case of the Times, that was fear of far-left voices on the internet.”

These days, Weiss is thriving at Substack, where she charges US$5 a month, and where she has the freedom to explore provocative stories. Most of the pieces she now publishes, she says, would be unlikely to run in the opinion pages of the Times. For instance, a recent story about Maud Maron, a white woman who is, in the words of Weiss, “a lifelong progressive, Planned Parenthood volunteer, Bernie Sanders contributor and voter, who worked for Kathleen Cleaver when she was a law student and who is suing the Legal Aid Society for discriminating against her” on the basis of race. (Cleaver is a law professor who was involved in the Black Panther movement.)

Weiss says her Substack is now “significantly more” lucrative than her job at the Times was – so much so that she’s able to commission work. (Marketwatch recently reported Weiss’s revenue at US$800,000 a year, which it fact-checked with Substack.)

Noteworthy stories include new reporting on the viral “Central Park Karen” video, featuring a white Canadian woman who called the police on a Black male birder during a dog dispute; a collection of opposing views on vaccine passports and mandates, including a podcast conversation with an epidemiologist concerned about vaccine zealotry and its impact on the vaccine hesitant; an essay from a young Black Christian conservative critical of “woke” politics; and a resignation letter from a Portland State University professor critical of rising illiberalism.

The downside of Substack is distribution. “Love or hate The New York Times or the Washington Post,” Weiss says, “the satisfaction of having your piece read by millions of people is incredible. So a lot of my energy goes into thinking about, how can I make sure this story that I think is really important reaches a lot of people?”

Weiss also acknowledges that if you’re not an established name, it’s harder to make a living on Substack. In other words, it may not be a sustainable model for the generation coming up.

So, what does Substack do for the media industry, beyond publishing unconventional perspectives and giving well-known journalists autonomy and a regular paycheque? “I hope what it does,” Weiss says, “is show these mainstream institutions that are running scared of tackling certain subjects, or entertaining certain opinions, that that choice is leaving so much money and talent on the table.”

Others on Substack naturally have thoughts on why the platform is making a mark – and why media personalities would choose to publish there. Columbia professor, race commentator and bestselling author John McWhorter recently serialized a book on Substack, Woke Racism: How a New Religion Has Betrayed Black America, arguing the ascendant form of antiracism is a pseudo-religious movement that’s illogical, regressive and profoundly unhelpful for Black people. “The idea was, I’ve got to say this,” he tells The Globe. “And as the publishing houses started turning it down, I started thinking, How am I going to get this out there? Luckily there’s this thing called Substack.”

McWhorter’s Substack became so popular that the book eventually sold to Portfolio, an imprint of Penguin, and is due out this fall. What’s more, the Times has since recruited him to write a newsletter. This suggests the paper of record is watching the Substack phenomenon closely and, in response, broadening the range of perspectives it presents.

It begs the question: Is Substack changing the media landscape? The platform is, after all, home to some of the most pointed media criticism you’ll find. For instance, in Freddie deBoer’s top-ranked media post, “It’s All Just Displacement,” the journalist makes the argument that the media is in crisis. He writes that against a grim economic backdrop – the collapse of the media’s old business model, the decline in circulation and revenue, eroded pay, worsening working conditions, mass layoffs and accelerated job competition – all non-conservative professional media outlets have been captured by a fringe, far-left ideology that originated at elite American universities and spread through social media. “Those politics are obscure, they are confusing, they are socially and culturally extreme, they are expressed in a bizarre vocabulary, they are deeply alienating to many, and they are very unpopular by any definition,” the long-time leftist writes. “The vast majority of the country is not woke.”

Matt Taibbi, meanwhile, in a post titled “In Defence of Substack,” claps back at one of the platform’s many critics, media scholar Sarah T. Roberts, who has characterized Substack as “a dangerous direct threat to traditional news media” and “a threat to journalism,” claiming the work is not vetted by editors, or governed by industry norms and practices.

Taibbi, who has serialized several books on Substack and does a fair amount of original reporting on the platform, argues that traditional news organizations “long ago started to become infamous for betraying exactly those hallowed ‘norms’ to which Roberts refers.”

He points to a rift in the news business that’s at the heart of the Substack conflict. “Some of us were raised to think the reporter’s job is confined to gathering information and giving it to readers, who should then be free to do with it what they will,” Taibbi writes. “A new approach, symbolized by a Times column four years ago called ‘Trump Is Testing the Norms of Objectivity in Journalism,’ stresses choosing and presenting information in such a way as to ensure that audiences make the ‘correct’ political decision with the news they’re given. … This argument over method put many journalists in a bind. Some either had to get on board with what they considered a perversion of the job, or they had to find some other place to go.”

These are all possible explanations for why journalists are going to Substack – but why have more than half a million paid subscribers followed them there?

One of Substack’s founders, Hamish McKenzie, once a student at the University of Western Ontario, is an author and former journalist, and he believes the platform is filling a significant void for readers. “It doesn’t feel like a great experience to be a reader today,” McKenzie says. “It feels like our minds are being broken.”

What dominates media today is the attention economy, he says, which incentivizes content that drives us apart, rather than encouraging dialogue, understanding, trust and the pursuit of truth. Twitter culture – with its quick takes, endless dunking and high-octane anger – has seeped into mainstream media culture, he argues, whether on the right, the left or various subcultures in between. “There’s discontent,” he says. “There’s a yearning for something different, and the writers at Substack have come along at an important time to offer that.”

McKenzie and his co-founders, Canadian Chris Best and Toronto resident Jairaj Sethi, started the company in 2017, partly out of despair. “Despair at the current state of the media business – newspapers going out of business, magazines doing the same, layoffs happening at a mass scale and local news in particular dying,” McKenzie explains. “But also despair at the state of the media economy from a societal viewpoint.”

Substack’s format turns the temperature down, he says, slowing the discourse, encouraging thoughtfulness and allowing the luxury of being wrong. And because of the platform’s independence, it also allows writers to be fearless. Which, he points out, is vital for a free press.

“Stuff I read on Substack is scrappier and messier,” he says, “but it’s also more diverse in terms of the viewpoints represented. And so I read a lot more stuff that I might not have previously gravitated toward, that contains viewpoints I disagree with.”

The media has, in recent months, been flooded with critiques of Substack, ranging from calls for robust content moderation and charges of transphobia and elitism – Substack Pro offers six-figure advances to marquee names – to claims that the platform traffics in media gossip, “selling soap operas to people who believe they’re above soap operas.” (Mind you, that didn’t stop the source of that criticism, The Atlantic’s Helen Lewis, from having her own Substack.)

In spite of this tension, Substack has become so successful that it’s not just The New York Times taking notice; both Twitter and Facebook have launched their own newsletter services.

And while many of the headline-grabbing newsletters are written by Americans, the trend is gaining steam in Canada. One of the more well-known Substacks in the country, The Line, was co-created by Calgary journalist Jen Gerson, who pined for “more lively, provocative commentary on politics and culture in Canada.” The team now publishes a range of commentary from journalists, opinion writers and experts.

Readers like the idea that there are some enclaves where writers are free to speak their minds without self-censoring, says Gerson. “The readers aren’t paying for the content that lands in their inbox,” she says. “They’re paying because they think it’s valuable that you’re there. That’s a really important thing to understand.” If people are willing to pay for Substack, she argues, it says something about what they feel is missing elsewhere.

Gerson believes The Line has already helped broaden the scope of views expressed in Canadian media. “There was a pendulum swing, and I do think the pendulum has swung back a little bit,” she says. “I do think our presence had a part in that. I’ve been told that people looked at what we were doing, realized that, yes, this was happening, and, as a result, opened up again.”

This is good for media, and good for democracy. “I believe that a political or intellectual culture needs disagreement,” Gerson says. “It needs conflict, it needs different points of view. It’s healthier, better, more interesting.”