Is the Solo Newsletter Business Worth It?

New platforms appeal to writers who want to publish independently. But are they sustainable?

Luke O’Neil has been waiting two months to hear back from an editor at a “very famous” publication and he is growing increasingly frustrated. The piece, into which he estimates he poured several thousand dollars’ worth of work, will eventually — hopefully — earn him just a few hundred dollars. But not even that is for certain — his vanishing editor would have to return his emails first.

In the meantime, during those two months, O’Neill has published over a dozen free dispatches of his email newsletter Welcome to Hell World via the newsletter platform Substack. The entries cast a wide net, including personal musings on mental illness and addiction; interviews; and even reported pieces — a recent deep-dive on payday loan-like schemes spurred the Huffington Post to cut ties with a service that let freelancers get paid immediately in exchange for a cut of their earnings. Last week, he made the move to monetize the newsletter, as Substack lets writers charge for subscriptions.

For each of these entries, the only person who gives the green light for publication — the only person who assigns stories and edits them — is O’Neil himself. “I just don’t want to ask permission anymore. I want to write what I want to write when I want to write it,” says O’Neil, who has been a freelance writer for around 15 years. “I can’t describe how liberating it is to wake up with an idea in my brain, spend a few hours writing it, and see it rocketing around the internet by the end of the day. It’s just great.”

But that thrill of independence comes at a price. You might have to work for free before you can reap the financial benefits. And independent, to a certain extent, means solitary — no editorial team, no legal department. Substack might be a way to supplement your income, but it’s not a solution to the dying news business in and of itself. Is the solo newsletter business worth it?

Tech journalist Hamish McKenzie launched Substack in July of last year with co-founder and CEO Chris Best — formerly the co-founder of teen-centric chat service Kik, where McKenzie worked as an adviser. Jairaj Sethi is the third co-founder and CTO. Their mission was to serve “writers who are striking out on their own.” They wanted to offer the technology that would allow writers to self-publish and monetize their work based on subscriptions alone, with no ads, no anxiety over clicks, no being beholden to outside forces.

Freelancing is tough already, of course. “It can be an exhausting and emotionally difficult process, the uncertainty and instability of it, and the feeling of ‘Goddamn, I really believe in this story and you don’t,’” says McKenzie, who was a freelance writer from 2010 to 2011 before getting a job at the since-shuttered tech news site PandoDaily.

“I would argue that the better move would be to invest in yourself and invest in your own future and set yourself up in a way where you don’t have to rely on the editor at that publication giving you a ‘Yes’ after some period of time,” McKenzie says.

He explains the strategy of this approach using startup jargon: If you invest in a newsletter, you have an opportunity to “scale,” meaning you can grow an audience of paid subscribers. Your income goes up while you produce the same amount of work with the same amount of effort. “It builds over time. It’s not like you’re doing more work for it, but more people want it,” he explained.

The other option means “hustling for the scraps,” according to McKenzie — pitching, laboring, and getting paid roughly the same amount for each piece. That hustle doesn’t scale.

But scaling is hardly a given. It helps to have a built-in audience from the start. Among the most popular paid newsletter proprietors touted by Substack are Nicole Cliffe and Daniel Ortberg, founders of beloved quirky feminist site The Toast (RIP), former child star Mara Wilson, and controversial politics reporter Matt Taibbi.

There’s also Judd Legum, founder of political news site ThinkProgress, who struck out on his own in July of this year for the same reasons outlined by O’Neil. “I don’t necessarily want to have to convince somebody that my idea is good,” he explains.

So he launched Popular Information, “a political newsletter for people who give a damn.” He had to build a list of email subscribers starting from zero, but it certainly helped that he had a considerable Twitter following. He ran the newsletter exclusively for free until October, and now charges subscribers who opt into a paid level $6 per month or $50 per year, which seems to be an average buy-in for the new newsletter market.

While he declined to share how many paid subscribers he has amassed, he says roughly 30,000 readers receive the free version of his newsletter and that he is earning enough from paid subscribers to qualify as a full-time job. (If just one sixth of those 30,000 subscribers opt into the paid yearly schedule, that’s an annual income of $250,000, though Substack takes a 10 percent cut of the earnings from all paid newsletters, so it would really be $225,000).

For others, beginning with no bylines and no industry recognition, newsletters have provided an entry point into a writing career on their own terms. When Helena Fitzgerald launched her beloved newsletter Griefbacon (of which I am a paid subscriber) on the free subscription service TinyLetter in late 2015, she had a full-time job outside of media and viewed it as an experimental passion project. The newsletter format gave her a safe, controlled space in which to explore the personal essay format — rather than, say, selling her personal experiences to a widely-read women’s website for pocket change.

“It felt like a place where I could experiment with personal essays and play around with different forms of narrative nonfiction,” says Fitzgerald. “The free TinyLetter format gave me a really great form in which to do that, because it felt like a lot lower stakes.”

To say Griefbacon has “scaled” since then would be an understatement. Two years later, Fitzgerald had established a career as full-time writer — in part, she says, thanks to the exposure of her increasingly popular newsletter. “I did have some clips, but before I really had a wealth of links I could just send, this was something where people did become more familiar with the stuff I was writing,” she says.

She had also, in that time, hit Tinyletter’s ceiling of 5,000 subscribers. That’s when she decided to monetize it. “It no longer felt sustainable to do it for free, because at that point I was having to use the time I could have been using for paid assignments,” she explains. Like O’Neil, she had received a message from Substack encouraging her to try their service and decided to put out paid version of Griefbacon, at $5 per month or $50 per year. That launched at the start of 2018. She says the earnings have made a “huge difference” for her financially, covering most of her monthly bills.

For most people, Substack has become the writing equivalent of selling your homemade jewelry on Etsy: fun and an okay side-hustle, but by no means a replacement for your job. While there are “many hundreds” of free newsletters on Substack, McKenzie says that on the paid end there are 50 to 60 earning more than “a few bucks.” A couple dozen are making “good money,” where it comprises a significant portion of their income, and an estimated 10 to 12 are making enough to stand in for full-time job.

If you can build an audience through your work, the reasoning goes, then all the “free” work you did was not really free. O’Neil agrees with this characterization. “In theory, I’m not working for free,” he says. “It’s like when you open a restaurant — you do a couple weeks of trials where you’re not making money.” He has 2,200 subscribers to his free newsletter and just last week took the plunge into monetization at $6.66 per month (staying on brand), or $50 per year. He is hoping at least 20 percent of his subscribers will go for it. In the meantime, just months after launching, he has been offered a deal from a small press that wants to turn “Welcome to Hell World” into a book.

There’s something radical in the simplicity of the Substack model, in the direct, unmediated nature of the transaction. Someone likes your work and they pay you for it. It feels like a throwback to the age of Livejournal – a loyal, growing readership subscribing to undiluted, often intimate dispatches — only this time around, entrepreneurs have monetized the blogosphere beyond a PayPal tip jar.

The media industry is imperiled by an advertising-centric model that thrives on outrage clicks, McKenzie argues, and Substack could change that. “Instead of serving a master like an advertiser or a platform like Facebook or Google, you serve the reader’s interests,” he says. “There’s a long term and a short term — long term you could have an entire media system based on payment and subscription. In the short term, we wanted to make it easy for a writer to start a paid newsletter.” And even if Substack only ever excels at that short-term goal, McKenzie says, he will be happy. (Though his Silicon Valley investors might not be satisfied.)

TinyLetter is Substack’s most obvious predecessor. It was founded in 2010, acquired by MailChimp in 2011, then relaunched in 2014. At the start of this year, the company announced that TinyLetter will ultimately be integrated into MailChimp, though when and how remains to be seen. Even if Tinyletter were to survive, however, it’s better suited for personal side projects than earnest business endeavors. Unlike Substack, it doesn’t allow writers to charge, and has a subscription cap.

Patreon is, of course, another option for artists and others looking to charge for their work and includes creatives outside writing. A few other companies have tried their hands at the newsletter model but don’t seem to have gained as much traction — Dutch newsletter service Revue, for one, and the Seattle-based Buttondown. Even Patreon, like Substack, has many more unsuccessful or minorly successful users than it does superstars like Chapo Trap House.

There are logistical problems to be worked out if Substack and its ilk are truly to provide a new, sustainable ecosystem for media. While the pure, undiluted nature of the blog post might complement more personal writing, many reporters (myself included) would break into hives at the thought of sending their news copy into the world without a rigorous edit, or at least one fresh set of eyes on it beforehand. Then there’s the issue of legal protections. In October, Legum reported on Iowa congressman Steve King’s white nationalist ties as well as the corporations that continued to sponsor him. Does he ever worry about reporting on such explosive content without the backing of company lawyers?

Legum says it has crossed his mind, and he is considering defamation insurance, but he also enjoyed the fact that the buck stopped with him when corporations called to complain. “It’s kind of nice to know, ‘Well, you can talk and I’ll listen, but there’s nobody else to call,’” he says.

He is also considering hiring a copy editor, though he has a current (free) system that’s working fine for now. A volunteer reads his copy the night before it goes out, and his wife reads it in the morning. (McKenzie, for his part, says Substack is toying with the idea of eventually providing legal protections and benefits like health insurance, but that could be a ways in the future for the young company.)

Plus, the medium is, in many ways, more pleasant than a traditional media platform — if the audience largely consists of subscribers who are invested enough in your work to pay for it and get it in their inbox, you’re going to deal with far fewer trolls and less bad faith criticism.

“I think it’s a really positive personal medium,” says Legum. “It sort of makes you feel better about what you’re doing.”

Correction: Added Jairaj Sethi as co-founder and CTO of Substack.

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