I endeavoured to make it both entertaining and useful, and it accordingly came to be in such demand, that I reap'd considerable profit from it.
— Benjamin Franklin, Poor Richard's Almanack
What goes into newsletters? What makes them stick?
If you asked enough successful newsletter writers, surely the common threads would come into focus.
The newspaper process—or at least the glamorized, twentieth-century version of it, with words scribbled in notebooks, punched out on keyboards, presses stopped and headlines swapped—has been immortalized on the silver screen enough that most can recognize its broad structures, its clichés. Same for the book publishing process, with agents, publishers, and advances, book tours and paperbacks, translations if you're lucky and options if you're exceptionally so. Newsletters, not so much.
They're real, a million writers showing up and hitting send, week after week, making a dent enough to have already affected public policy and drive a collective hundreds of millions of dollars in annual revenue. They're the default way to start publishing long-form writing online, today. Yet new publishing is, all too often, only treated as significant when acquired by legacy publishers and tech firms. There's no film about a newsletter, no Netflix series about building a Substack or blog from the ground up.
What would one show in film, anyhow, to let the audience know in 30 seconds that the protagonist was a newsletter writer?
The totems are obvious enough: The laptop instead of the 1960 reporter's typewriter, the newsletter app in lieu of the printing press, the blank page with its eternal terrors. Across hours of interviews, we dug into the inflection points that newsletter writers could point to as the line between success and failure. What could a budding newsletter author learn so they, too, could go from Issue 1 to one thousand true fans?
You'd think there would be more similarities across newsletters than differences, things that would lend themselves to a 12-step process that if you follow it, you too could have newsletter success.
Or so was our original thesis.
One step in front of another
"I've been writing for twenty years," says software founder Allen Pike during our call of his eponymous newsletter. "Twenty-seven years," says Creative Good founder Mark Hurst, without a hint of arrogance. "Thirty," smiles New York Times journalist and author Clive Thompson. "I've written, you know, three, four million words in this format," he says of his blogging and Link Fest newsletter output. Enough to fill 30 books, if a book's a hundred thousand words.
"It's literally come out five hundred and twenty six straight weeks, on a Tuesday, at more or less the same time," says Mario Fraioli of his newsletter, the morning shakeout. "It's something that has truly been my consistent thing for, like, eight years," says Cassidy Williams of her rendezvous with cassidoo newsletter.
Keyboards worn out. Midnight oil burned. There the similarities ran out. The paths to newsletter success were as varied as the authors themselves.
Cadence mattered, but every writer settled on a different pace. "When I first made it, I was so motivated, I was like, whoa, I should write this every day," said Williams of her newsletter's cadence. "Then I stopped myself, because I knew that would be really hard to sustain. And so I started it weekly." Pike needed a lower cadence: "I set a goal that I would write at least once a month," he says.
Then comes Pell. "I'm addicted to publishing every day," he says, and somehow has found the stamina to have done so for two and a half decades and counting.
Stats, too, mattered, but again in different ways to different writers. "I watch them," says Mongkol. "I write a three month report to myself, to put things on paper and see how they're doing."
"I used to check stats daily," concurred Pell, before backing off.
"I do a year-end review and check all the numbers," says Pike. Then, Jane Friedman of Electric Speed says "I don't pay a lot of attention to the numbers" and uses them only as a broad indicator.
Some took unsubscribes hard; others aggressively pruned their lists down to their ideal reader base. Some built a team to support their newsletter work; others continue the hero's journey alone.
Software didn't ensure success, either. Most of the writers we interviewed have hopped between a handful of blogging and newsletter platforms; some have never been Buttondown users.
I've always felt compelled to write.
— Mark Hurst, Creative Good
Nor were topics as important as you'd think. "From the very beginning, my newsletter has been personality driven," said Fraioli. "It comes from me." Thompson's blogs and newsletters have been "kind of interesting stuff that I was encountering in science and technology," not all of which was all that popular at the time (clean tech, say, two decades ago). Williams' newsletter is a random smattering of news, a coding question, "and then also, I like jokes, so I included a joke at the end, too." Friedman's newsletter was more focused. "Who wants to spend time in an email?" says Friedman. "Mission oriented is how I approached it, in and out."
Even after all of that time, writers couldn't fully predict what their audience would love. "You have no idea what's going to take off, so you just do a volume business," says Thompson.
"You write however many thousands of posts and inevitably something is going to hit," says Hurst.
"It's always just a crapshoot," says Pike.
"I was really prepared to write into the void for a few months," says Chatawan Mongkol of Soiciety.
Newsletters are an exercise in madness, in self-delusion. They're the purest statement of faith in meritocracy, that the universe rewards effort, that there are others out there who think like you and they, too, would resonate with your writing. Newsletters self-select for those driven by the urge to write, by the conviction that putting your words and ideas out into the ether is a reward of its own.
"I've always felt compelled to write," says Hurst. "I've always enjoyed it, I've always wanted to keep on doing it," says Thompson.
"I cover the news in the year 2025, so I'm tempted to stop sending every time I open a new browser tab," says Dave Pell of NextDraft. "But I'm addicted to publishing every day."
You'll write your way out
Success, it turns out, is random. Arbitrary. The things that worked for one didn't for another.
But it wasn't purely random. For behind every successful newsletter is a writer. A writer who one day, showed up and decided to start publishing. A writer who continued to show up, daily or weekly or monthly, and write. Their paths varied, their plans mattered less than we'd like to think. The constants were starting and continuing to show up.
"What I really need to do is just hold myself accountable to this and get it started," Fraioli recalled telling himself. "I'll figure it out ... once it's out in the world."
"I knew that no matter what I write in a plan, the actual thing is going to be different," conceded Mongkol.
"I guess I was just happy to start a conversation with people on the topics I was interested in," recalled Hurst.
The output of a decade or three, of millions of published words, of thousands of subscribers and millions of readers, of the hopes of sponsors and businesses and book deals, of the reality of duds and false starts and silent failures, of readers and repliers and finding your tribe: Newsletters all start in the same place.
One day, someone opened a blank page, stared down the blinking cursor, and typed their first word.
Start. Show up. The rest, they'd figure out along the way.