Why doesn’t Mallory Ortberg ski on a pile of money?

This story is about Mallory Ortberg, the writer, co-founder of The Toast, and Dear Prudence columnist who has just started her own paid newsletter, The Shatner Chatner. But we’re not going to mention her name again for a few more paragraphs. First, we have to tell you why she isn’t just dripping with cash.

Giant businesses could once be built around writing. Advertising sustained two centuries’ worth of mass textual dissemination. But the riches of the newspaper industry, even in its gloriest days, could not whisper at the economic might of selling fluidized fossils, or manufacturing transportation machines, or twiddling with the imagined symbols of wealth exchange. Bankers get rich. Investors get rich. Landlords get rich. Lawyers get rich. Marketers get rich.

Writers do not get rich.

Writers struggle. Writers find it hard to pay the rent. Writers, with a few accidental exceptions, drink the cheapest beer. Writers are willing to always have financial anxiety if it means they can just write.

But writers deserve to be paid. They are culture shapers and carriers. They help us understand who we are. It is through the work of writers that we learn the rules of existence, share the plights of strangers, occupy the mindsets of brilliance and despair, whimsy and suspicion. Writing is the road into the minds of others.

“Gods always behave like the people who make them,” wrote a novelist who, in her later years, had to get by on public assistance.  

“There is a wisdom that is woe; but there is a woe that is madness,” penned a man whose income from writing was never enough to support his family of six.

“If this isn’t nice, what is?” said a former GE publicist.

Where would we be without these words? They have delivered a richness to our lives that wasn’t always returned to their authors. And those were in good times, when high-paying jobs at newspapers and big book deals were growing not disappearing. Now, because writing is increasingly hard to “monetize,” even the best of the class are reduced to being producers of content that can be attached to ad units.

And so, Ortberg. At 31, she has already brought a lot of richness to the world. She was a driving force at feminist site The Toast, where her writing moved readers so much that several asked for her hand in marriage. She and Nicole Cliffe started the site after finding each other in the comments section of The Hairpin (Cliffe has announced that she is also coming to Substack). Ortberg was a broke grad at the time, then took a job at an academic publishing house, and then did weekend shifts at Gawker, before, in June 2013, she and Cliffe decided to do their own thing. Ortberg specialized in imagined dialogues and other literistic meanderings: texts from Jane Eyre; Mary Poppins, except written by Ayn Rand; revelatory interpretations of medieval monastic art (Two Monks Discover How Tall Women and Horses Are); and meditative essays on the nature of human psychology (Everyone Has Imposter Syndrome Except You).

It was ultimately too much of a struggle to keep it alive, financially speaking, but The Toast was a cultural phenomenon. HuffPo called it a “feminist utopia.” Slate memorialized it with a greatest-hits tribute. Hillary Clinton wrote it a farewell note. But its most meaningful impact could be seen in the community that gathered around it and persisted after its departure. There are meet-ups, a subreddit, #ToastieTwitter, and Slack channels. The members of these groups, according to Sarah Scoles’ terrific profile of Ortberg, support each other IRL, form book clubs, cover each other’s medical bills, help friends out of abusive relationships. It was writing that brought them together.  

Some of these people have appeared in our inboxes since Ortberg brought The Shatner Chatner to Substack. She asks subscribers to pay $5 a month (a bargain), but she makes exceptions for those who can’t afford it. Helping her implement this, and passing on the sheer gratitude she has received in return, has been a moving experience.

But of course, despite her success, Ortberg is still a writer, which means the uncertainty is always there. Writers, after all, don’t make tech money. The independent source of income from her paid newsletter is a bulwark. “I have a couple of solid freelance gigs, but you never know when someone might decline to renew your contract,” she says, “or an outlet might lay off half their editorial staff, or your book might not sell.”

Substack exists because we want to help subvert this entire order. We believe that great writers create tremendous value, and that should be reflected in their bank accounts. We believe that when readers pay writers directly, everyone wins. Readers benefit from the best thought a writer can produce. Writers get paid without perverse incentives compromising their work.

And so, Ortberg is publishing with Substack. The relationship is off to a good start. “I’ve made enough money from the first two weeks of subscriptions that I can actually put something into my retirement account and set aside money for taxes for the spring,” she says. “That’s huge for me.”

Writers do not get rich. But for most, that is never the goal. They just want to be able to do the work they love and be justly rewarded for the value that they create. We will do everything in our power to make that happen.