Decisions are made by those who show up.
— President Jed Bartlet, The West Wing
Mario Fraioli showed up in 2015 with a tweet. "Hey, I'm working on this thing. It's going to come out next Tuesday. If you're interested, here's where you can subscribe," he later recalled posting.
A runner, coach, and senior editor for the running-focused Competitor magazine, Fraioli was looking for his next thing. He was increasingly known for live-tweeting races to his ten thousand or so followers, and "started thinking about doing a creative project that was all my own," he said during our Zoom call.
He considered a blog, or even a print zine on a slower cadence. The primary consideration, though, was attention. Would people care enough to read his writing? "I wanted people to read whatever this thing was that I was going to put together and write. The most direct path to that," he concluded, "was to meet people where they are: their inbox."
So he drew a line in the virtual sand by tweeting (back when that's what it was called) the announcement before he'd written the first issue, and 200-or-so of his followers came along for the journey. And he did it again for five hundred and twenty six Tuesdays, turning the morning shakeout newsletter into the thing over thirteen thousand runners read every Tuesday morning.
Cassidy Williams showed up in 2017, with an ultimatum. "If you want people to listen to you, you need to be in their inboxes," Udemy's team advised before launching her JavaScript and React for Developers course. "That is when I came up with the idea of writing this newsletter, so I could eventually promote my course," Williams reminisced, now four hundred and thirty five issues into her newsletter.
Clive Thompson showed up in 2002, because "I wanted to keep on writing," he recalled, during an MIT Knight Science Journalism fellowship. "You spend a year, they pay you to learn, and don't want professional writing to take away from your time there," he said.
But when you're accustomed to writing as thinking, taking a hiatus feels as wrong as it would for a runner to stop logging miles. "So I downloaded this crazy new software called Movable Type," says Thompson, "and started blogging." A blog turned later into a Medium publication, then a newsletter, as audiences and attentions shifted, and he discovered a new voice along the way. "What was interesting was discovering what I sound like when there's no in-house style," he said. Before long he'd been writing on his own, in his own voice, away from the constraints of editors and advances, for twenty-three years.
Mark Hurst showed up in 1998 for much the same reason. "I've always felt compelled to write, pretty much my whole life," he said. His first newsletter wasn't much, "just a plain text email," he recalled, but it was something, the start of a text-based conversation about his favorite topics that he's continued, across platform changes, for twenty-seven years.
The first issues were never that fancy, the audiences piddling, the voice and topics yet to be set in stone. But they were the first step in a journey of decades. Like the starting line of a marathon, where it takes a beat to break out from the crowd and settle into a pace, what matters more than anything else is showing up and taking those early strides.
The first step is the hardest
Starting begins before you send that first email, when the initial seed gets planted in your mind that you should start a newsletter. Perhaps you're building something new, as Williams was, and want an audience primed for its launch. Or you're at a transitory period, as Thompson was, and want a way to exercise your writing muscle and put a purpose behind your output in the interim. Maybe you just love writing, like Hurst, and feel compelled to do so, audience or none.
Newsletters make sense, for those goals and more. They're, in Fraioli's words, published where people already are. No algorithms to fight for attention, no new habits to have to build among readers, few platform considerations to worry about. You don't have to "fight through some algorithm and do this dancing peanut dance, with your top hat and your cane, so that people will read it," said Thompson. Newsletters are just you, your words, and your subscribers---subscribers you can take to any other newsletter platform in the future at your discretion.
That's appealing enough to drive the deeper questions about systems and style and stamina to the background.
Dave Pell's interests drove him in 2008 to write a newsletter about the most interesting tech news of the day, as the latest move in a writing career spanning everything from syndicated writing to a print publication for a spell. Chatawan Mongkol's impending graduation, and experience running a student journalism-focused newsletter, drove him to see what he could build in a new newsletter before finishing business school. Jane Friedman's blog eventually morphed into a newsletter. "The first newsletter I sent was an RSS to email," she recalled. "I think I was using some sort of Google tool to run that."
Allen Pike was already blogging, too, when reader demand pushed him to start a newsletter.
"I would occasionally get someone saying, 'I wish I could get your articles as a newsletter, as I don't use RSS,'" he recalled.
So he added it, half-heartedly at first. "The newsletter has always been a formatted email version of the writing that goes on my blog," he said, dragged into a new publishing format by readers. And to his surprise, the newsletter attracted more thoughtful, dedicated readers who took the time to reply. "The newsletter has outperformed in terms of helpful feedback," says Pike. "That was very much the turning point where I decided to commit more seriously to encouraging people that the newsletter is the best way to follow."
Inspiration, at its best, is an idea that arrives unannounced and refuses to leave. One day, you could have gone on without writing a newsletter. The next, this is the thing you're meant to do. Now you have to figure out how to pull it off.
Find a way to send emails – any way is fine
Your mind will, likely enough, eventually drift to software. You'll think through the email newsletter platforms you've heard of – Buttondown, Substack, Mailchimp, Kit, MailerLite, Constant Contact, Campaign Monitor, and a host of others. You'll faintly recall that blog platforms like WordPress and Ghost can send emails, as can LinkedIn and Medium. You'll be tempted to Google comparisons and ask ChatGPT which platform to use. You'll get overwhelmed by the options and wonder, momentarily, if you couldn't get by with an ad hoc email newsletter powered by BCC (no, you shouldn't).
We'd be lying if we didn't say we hope you'd choose to use Buttondown. But we'd also be lying if we didn't say that your choice of newsletter platform matters far less than just starting.
Any email newsletter app can send your first messages. You can worry about the nuances later on.
Hurst, in '98, started with plain text emails, moving his newsletter later to Campaign Monitor then to Buttondown as the features he wanted from a newsletter platform changed over time. Friedman started with a Google-powered RSS-to-email automation, likely through Feedburner, and later switched to Mailchimp's take on the same automation since it "allowed me to actually customize what was in that message, the header and the footer and so on," she shared.
Dave Pell started with Mailchimp, a decade and a half ago. "Using a third party newsletter service for delivery was a must," he explained, "because of the spam issues in the early days." Fraioli was less worried about the technical details, and more about the price: "Mailchimp was free up till 2,000 subscribers," he recalled of their pricing at the time, "So I was like, I'll just do that, and I'm not going to pass 2,000 subscribers, so it's not going to cost me anything."
Thompson started without a newsletter, writing on a blog, then Medium, and only later switched to a newsletter. "The desire to say something at length to a calm audience that is there to read it had not gone away," he said. "Newsletters actually satisfied that blogging urge better than blogging or social media did."
The writing and audience were what mattered; the platforms were just implementation details.
Choosing to focus your social media energies on LinkedIn versus TikTok might yield drastically different outcomes, and require entirely unique skill sets to master. Not so for email newsletters (and blogs, generally). They're one of the last remaining bastions of self-ownership on the internet. No one owns email; everyone can make it their own.
You can always export your subscriber list and import them into another email newsletter platform in the future, if you want. You can comparison shop the various email platforms once you have a few issues under your belt and know what features are worth having. But that's for later.
What matters far more, now, is sending that first issue to your first readers.
Your audience is there for the asking
An idea, email software, and a blank page ready for your words. All that's left is to fill in the subscriber list, and you'll have a real newsletter.
Which is exactly when you'll be tempted to back out of the quest, for who will read your writing?
Your family and friends, perhaps; they won't complain if you send them a first draft. Your social networks hold promise, as do subscribers to any blogs or channels where you've already been publishing. And you can always take up the proverbial bullhorn and promote your writing, as hard as that may sound today.
Pell started with colleagues: "I only sent it out to people who ran or worked at companies I invested in and/or advised," he said, then "word got out and people started to ask to be added to the list."
Mongkol started with friends, and Reddit: "The first issue I sent to nine people I knew," he said, "and I promoted it on Reddit." And that worked, with 60 subscribers on the list by the time he sent the second issue.
Pike and Friedman both started with their blog audience, as yet another way to follow their writing. Only later did they try promoting their newsletters more widely.
Thompson "did not advertise" his newsletters at all, he says. Aside from sharing on Twitter and Mastodon, "I have no idea how people found it." And he's restarted his list multiple times, leaving older followers in Medium as he migrated his writing efforts to a newsletter.
Williams and Fraioli both started with their Twitter audiences, and grew, in Fraioli's words, "from my consistent presence on Twitter and, then again, just word-of-mouth."
From Mongkol's nine friends to Fraioli's initial 200 signups from a pre-launch tweet, none of the writers started with a massive audience, but neither did they start out with an audience of zero. You need at least a few people to serve as a sounding board, to read your first issue and hopefully share it with their friends. You need to promote your upcoming newsletter in any channel where you have even the smallest audience, then re-promote that first issue wherever you can.
But you don't have to worry about it too much. You don't need that thousand true fans, not yet. "The single biggest change is going from zero, no audience at all, to one person," says Thompson, especially that first person who you don't know personally who signs up just because they like what you're writing.
Plus, you have this tiny window of opportunity, right at the beginning, to find yourself and discover your voice. "When you're a very online person, you're always editing yourself to accommodate the least charitable reader you have, which is no way to write and publish," says Friedman. "You lose your own sense of self and voice because you're hearing that horrible person that you know is on your list that's going to take issue with something innocent." You don't have that. Not yet. That's a gift for the present, a chance to build up your writing muscles for the months and years ahead when you will have a larger audience.
Starting, imperfectly
Most of the things that worked out over time, Pike told us, were things that he "did sort of accidentally and then gave a bit more attention once they started to work." The only way to know was to try.
"You'll always have that anxiety when you publish, and I don't think that will go away," said Mongkol.
"I was writing personal essays in a personal voice," recalled Thompson of parts of his newsletter, "and it was scary in a way."
Which, for most of us, puts us back into analysis paralysis. Is this name ok for a newsletter? Did I pick the correct software? Will people actually want to read my newsletter? What if I post about it, and no one shows up?
I'll figure it out, what it's gonna be and how it's gonna evolve, once it's out there in the wild.
— Mario Fraioli, the morning shakeout
"I kicked the can down the road on starting it for a while," recalled Fraioli, worrying about the branding, the design, the details that add up to a newsletter and yet don't matter all that much in the grand scheme. That is, until a designer friend told him "Dude, don't worry about the logo. Just put it out."
Thus the fateful tweet, "so that I would actually stop dragging my feet and get the thing out into the world," he said, and the first newsletter issue went out the following Tuesday. It was hard enough to get started; there were infinite tiny details, and you'd never hit the asymptote of perfection if that's what you were waiting on to ship.
"I'll figure it out, what it's gonna be and how it's gonna evolve, once it's out in the world," he decided, and mailed his first issue to his 200 early subscribers. Then he did it again, and again, every following Tuesday, until it became enough of a success to make it worth tweaking all the things that a real newsletter deserves.
Before you start, the first email is all that matters. After that, it's all about maintaining momentum.