Why Most Newsletters Fail

For a select few journalists, Substack is a path to fame and fortune. But the service hasn't changed the lousy math of being a freelancer.

Welcome back to What Went Wrong?, a newsletter about the failures, inefficiencies, and screw-ups that define 21st-century American life, written by Harry Cheadle. Please subscribe if you haven’t done so. Above photo a screenshot of Carrie “Secure the Bag” Bradshaw.

Writing a newsletter is great—or it is, I imagine, if you are famous. For the past year or so, prominent journalists have been bailing on the publications they wrote for and launching their own Substacks, usually with a long-winded explanation about how they don’t want to be constrained by the editors and institutional biases of their former workplaces. As an added bonus to their much-ballyhooed independence, they make a lot of money by transitioning to newsletters.

If you charge subscribers $5 a month (a common rate) and get 10,000 subscribers (an achievable number if you have a large and engaged social media following), you’re clearing $45,000 a month after Substack takes its 10 percent cut. Andrew Sullivan, who was pushed out of New York and wrote a goodbye post about the magazine’s left-wing “orthodoxy,” saw his annual income rise from under $200,000 to over $500,000. Matt Yglesias, the Vox cofounder who left his gig voluntarily and had similar criticisms of his former workplace (though he was nicer about it), could easily clear a similar sum. In 2019, Substack said its top dozen newsletters made an average of $160,000 a year, a number that has definitely gone up as the platform has grown in readership and added boldfaced names like Sullivan, Yglesias, and Glenn Greenwald. 

Substack occasionally holds itself out as a new model for journalism, an industry where making money is notoriously difficult. “Start a newsletter. Build your community. Make money from subscriptions,” its site purrs at you. The company has also funded writers it sees potential in. The most prominent of these may be Emily Atkin, who got a $20,000 advance from Substack to launch her climate-focused newsletter, Heated, which has grown to one of the platform’s most popular publications and turned Atkin into a climate journalism star. Though that advance meant she had to pay a bigger chunk of subscription fees back to the platform for a while, she’s undoubtedly made that back and then some—Atkin recently told Columbia Journalism Review that she made $200,000 a year.

But as that CJR story lays out, though Substack has been a boon to some writers shut out from traditional outlets, it has largely replicated the pyramid-shaped, winner-take-all dynamic of the old media system. “The most successful people on Substack are those who have already been well-served by existing media power structures,” the story notes. Most people with Substacks—myself included—don’t earn much money, at least not enough to make it financially worthwhile. I’ve talked to several fellow Substackers who have struggled to find audiences or build their newsletter to the point where it pays off financially or otherwise. 

Newsletter writer Ben Reeves told me that Substack has “developed this mystique of being this place where journalists are able to go and thrive.” After nine months of putting out his newsletter Highly Transmissible, however, Reeves doesn’t feel like it’s sustainable for him and is considering pulling the plug. The question writers need to ask themselves when considering starting a Substack, he says, is, “is it in your best interest?” In many cases, that answer is probably no.

Being a freelance journalist is lousy

The most aspirational work of fiction about journalism ever created is Sex and the City, in which Carrie Bradshaw lives in a fancy part of Manhattan, eats at restaurants for every meal, and never wears the same outfit twice—a lavish lifestyle apparently funded by writing a single newspaper column every week. At one point she starts writing for Vogue and we learn the secret to her financial success: her rate of $4 a word. 

If you made $4 a word, freelance journalism would be an incredibly lucrative career. If Carrie’s column was around 1,000 words, at one column a week that’s $208,000* a year. Not too bad, especially when you consider that that salary in 1998 (when the show first aired) works out to $332,000 in today’s dollars. And one column a week leaves a lot of time for consumption of cosmos. 

While $4 a word might have been an exaggeration even in the lavish bygone world of late-90s glossy magazine journalism, today it’s a laugh-out-loud funny anachronism. No writer I have ever met has made $4 a word, or expected to. Normal freelance rates for reported stories around 1,000 words—which generally require more work than Carrie’s I-couldn’t-help-but-wondering—range from $300 to $500 at big-name online publications. 

Pop quiz: How many stories do you need to do at that rate to make, say $60,000? You don’t need a calculator to know that the math is grim, and why being a full-time freelance journalist is such a drag. Most freelancers need another source of income, whether that means a wealthy spouse or family member, consulting or PR work, or branded content, a.k.a. advertising (this last option pays hilarious amounts compared to “real” journalism). For many, freelance gigs are a way to build a portfolio and contacts that lead to a staff job someplace. The problem is, those jobs are increasingly scarce. The local newspapers and alt-weeklies that provided a middle-class living to past generations of journalists have been broken by a combination of market forces and bad management; Carrie Bradshaw’s heels-and-cigarettes world of elite magazines has likewise been decimated. Even the digital media companies that have risen in recent years are struggling for air. (I wrote about this last summer after I lost my own job.) 

The Substack paradox

Britany Robinson’s newsletter, One More Question, is aimed at freelancers attempting to navigate this world, providing resources to journalists, interviews with prominent writers, and advice. Like most Substacks with paywalls, it offers some free posts and other subscription-only posts; you can sign up for $5 a month or $45 a year. 

“I think stories are really important,” Robinson told me. “I want to encourage other writers to stick with it, even though it's really going to suck for the next few months, or however long as the industry struggles with the pandemic.”

She has 800 subscribers and 100 paid subscribers, which earns her about $350 a month. “It’s really stalled out,” she said of those numbers, which is a potential problem: Robinson devotes five to eight hours a week to her newsletter, which works out to earning something around the minimum wage. “For this to continue to be worth my time. I really have to keep growing,“ she said. But she doesn’t want to stop, particularly since some of her subscribers have paid for the whole year. “That's a little bit of a conundrum of, well, if I don't start making more, it's not worth it. But also, I don't want to let the audience down.”

This is the paradox of Substack: If you don’t have paid subscribers, you’re working for free, and no one wants to do that. But when you do have paid subscribers, you have to keep the content coming.

That’s the lesson Kate Carraway learned. She’s been writing about health and beauty and wellness for years in outlets from the New York Times to Vice, and her unique voice has earned her enough of a following that when she launched a paid newsletter called More Feeling, it brought in twice the number of subscribers that she was hoping for. (She wouldn’t tell me exactly how much she was making.) But a single newsletter edition took an entire workday, and while she was devoted to making sure her subscribers got fresh content, she stopped keeping up with her free newsletter, and found herself too swamped with work to take consistent vacations. 

Carraway didn’t like other aspects of newslettering. It meant she had no editor—she’s one of those writers who loves the editing process—and her paid posts by definition were only read by people who already liked her work. Her columns for magazines and websites had let her reach new audiences, but there was no prospect of that happening with More Feeling. “I realized that I was doing all of this work to create something that would live behind a wall,” Carraway told me. So even though her Substack had become financially viable in a way many don’t, she stopped doing it. It wasn’t worth the stress and the amount of work she put into it.

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The haves and have-nots

These aren’t dilemmas elite Substackers ever face. Their newsletters draw in so many paid subscribers right out of the gate that they don’t need to worry about whether it’s worth it financially. The Andrews Sullivan of the newsletter world make so much money they can hire a staffer or two to spread the workload and allow them to take vacations. 

To its credit, Substack has offered grants and fellowships to some writers, and helps promote the work of others. But the vast majority of its writers have to do 100 percent of their own promotion and fanbase-building. If they succeed in attracting paid subscribers, the company takes 10 percent of their fees. Even though Substack offers perks to writers “real” publications do not (we own all of the content we put in newsletters, for instance), you can see how it’s potentially a pretty sweet business model. Meanwhile, for most writers, Substack “is what it is,” said Reeves. “It’s a free newsletter platform.” 

Earlier this year Mike Pearl, a friend and a former colleague of mine at Vice, started a newsletter about climate change and other science-y topics called We Are Definitely Screwed, Maybe. The posts are in-depth and he clearly devotes a lot of time to each one, but he hasn’t put up a paywall and isn’t sure what the Substack will turn into. 

“I have something in mind that I think that this newsletter could be, but I need readers,” he told me. “I need to know if I should be doing this or something else. It’s just growing enough that it feels like, some people do seem to like it, but nowhere near the point where I'll ever make money off of it. So it's like, do I stick with this? Or do I put my effort elsewhere?” 

Pearl said he regards his Substack as a “side bet,” and that’s how most newsletterers see this sort of work. Being a freelance journalist means making a lot of these side bets. Maybe your newsletter goes viral and your subscriber numbers shoot up. Maybe a feature you write gets optioned into a film and you’re suddenly in demand. Maybe a cold pitch to an editor turns into a long-lasting relationship that turns into a staff gig with health insurance and a living wage. Or maybe a branded content shop reaches out with a job offer and you are like, Well, that is more money than I have made in my entire life.

Substack isn’t exactly exploiting the labor of writers, who should know the deal they are signing up for. But it’s not a service that changes the bad math of freelance writing. There will always be an upper crust of pundit-journalists who go on TV and bring in six figures for a Bradshaw-esque amount of work. What is lacking are the decent full-time jobs that constitute a normal career. For many people out here in the Substacker-freelancer unwashed masses, a regular paycheck from journalism counts as a coveted prize. A Substack, in other words, is a lottery ticket. But journalism has become an industry with too many lottery tickets.

CORRECTION 12/3: Due to my bad math, I initially wrote that Carrie Bradshaw’s $4 a word rate meant she made $52,000 a year writing one 1,000-word column a week, a livable-but-not-spectacular-by-NYC-standards wage. As eagle-eyed reader M. Campbell pointed out, I was lowballing Carrie—she’d earn $52k at $1 a word, but a Greenwaldian $208,000 at her preposterous Vogue rate. Apologies to the Sex and the City franchise.

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Thanks to all of the Substackers who spoke to me. If you enjoyed reading this, subscribe and tell a friend! If you want to talk to me about this story or anything else, please email me.