TinyLetter, in memoriam

Before there was Substack, and long before the word “creator” was used with any kind of seriousness, there was a small newsletter tool that captured a moment: TinyLetter.  Appropriately humble in name, TinyLetter was light on features and heavy on focus. The canvas was a blank text box; the platform itself the most bare-bones way to send a bunch of emails. Publishing on TinyLetter meant stories would never be loud, go viral, or make any money. But this quietness was a strength, and for a brief era — I’d estimate 2012 to early 2016 — TinyLetter was where some of the most compelling writing was happening on the internet.

Today the service shuts down for good, a dozen years after it was acquired by Mailchimp, which itself was acquired by finance software behemoth Intuit two years ago. Its death is not exactly a surprise. The company cited low usage and the shifting needs of writers and readers. Both are true — and as the landscape has shifted and commercialized, TinyLetter has languished over the past decade. But it’s hard not to be a little sad when even a humble little service is sunsetted, especially one that contributed to such a strong and particular moment of internet culture. How many platforms had a distinct voice?

TinyLetter arrived at a specific transitional era of the web. Readers were visiting homepages less and less. (Though Google Reader, the company’s RSS app, never found mainstream adoption, it is often cited as the catalyzing moment for this shift in the internet.) And social media had started to take hold of distribution, sending publications in a frenzy for stories that would go viral.

This sent the classic forms of blogging into decline. What had started as an internet-native form of personal writing had been captured and packaged into a genre of more sensational confessional writing — xoJane’s “It Happened to Me” series are probably the most notorious example of a form that quickly went from pioneering to mercenary.

Yet people still wanted to write. Essayist and critic Charlotte Shane didn’t need her work to be widely read, but she wanted an outlet, one that was simple, unfussy. TinyLetter came recommended by word of mouth.

“Blogs seemed over,” Shane says, recalling the decision to start a TinyLetter in 2014. “Also, I didn’t like the idea of being nailed in place, available to be pulled up at any time. I wanted something a little more temporal and intimate-seeming.” (TinyLetter allowed archives to be turned off. If you missed an email, you missed it forever — a more ephemeral experience than her Tumblr.)

The public incentives of social media — likes, hearts, reblogs, follower counts, the metrics that platforms enthusiastically refer to as “engagement” — didn’t exist in email, and especially not on TinyLetter. The platform itself had no built-in recommendations or ways to self-promote, quashing any aspirations for virality. Even subscriber counts were originally capped at 2,000. You couldn’t even pay to raise the limit.

This is arguably what encouraged the personal writing revival on TinyLetter. At least for Shane, who writes under a pseudonym, she started Prostitute Laundry to write about sex work. Having a newsletter was about getting the reps in. She had freelance assignments at magazines, but writing toward a publication’s coverage, sensibility, and politics got her farther away from what she wanted to accomplish. “It’s bad for me as a writer. It makes me a worse writer. It feels bad as a person and it makes me unhappy,” she says.

But what she was publishing on her TinyLetter helped her explore shape and tone in her writing. Meanwhile, Shane could be read, but not by an audience so large that it would discourage her from experimentation.

Author Zan Romanoff, who wrote frankly about her anxiety and depression on TinyLetter, echoed a similar sentiment. “I don’t want to write a fucking xoJane essay or even Jezebel article about my mental health issues. People are going to think it means more than it does,” she says. This was a way to experiment, free of the pressures of a formal publication. “I just wanted to complain as if I was complaining to my friends.”

The unassuming nature of an email — the modern form of correspondence — made it intimate. Today, we have very few things that nurture that kind of writing on the internet.

“It was good to be reminded that there were things I would write even if nothing was necessarily going to happen with them. No money, no virality, sometimes even no response,” Romanoff says.

“That is sort of the original spirit of the internet,” Shane says. “What if we made no money? What if money wasn’t even something we were thinking about?”

TinyLetter was designed without any ways to collect payment. Philip Kaplan built the original version in about two weeks. According to him, it was simple from a technical level: “a signup form and a loop that sends emails over and over.”

Years earlier, he’d run a popular newsletter for his website, FuckedCompany.com. (“Personal musings. Kinda like when people had personal blogs, if you remember that,” Kaplan says.) When he wanted to start another newsletter, he realized that the only other email services were geared toward business marketing. The language of email was ROI, analytics, and segmentation. What if he made an easy way for normal people to write and send a personal newsletter? That seemed like a good idea, one a lot of people would find useful. TinyLetter was born.

Kaplan was right — by 2011, his little service was sending a million emails a month. But it wasn’t something he necessarily wanted to manage.

“I actually reached out to MailChimp, not the other way around,” he says. “I was busy with other work and thought it might be a good fit for them. So I cold-messaged their CEO Ben [Chestnut] on Facebook, who I didn’t know personally, and sent him a short pitch,” Kaplan says. “He liked it as a ‘MailChimp Lite’ and the deal was done!” (Kaplan declined to tell me how much the deal was for.)

Since its inception in 2001, Mailchimp has quietly become the leader in the lucrative space of email marketing. As it grew in the early to mid-‘10s, it suddenly became very cool, very profitable, and ubiquitous in certain spaces. (Remember the “Mailkimp” pre-roll ads ahead of Serial?) A beloved brand, some might say.

Before Rachael Maddux joined Mailchimp in 2014 as a writer on the marketing team, she’d only ever worked at nonprofits or places that made not-very-much profit. Here was a tech company, over 300 people strong, and flush with cash.

“The job wasn’t product marketing at all yet,” she says, “so it was kind of just vibes and the approach. Like, ‘Yeah, we got money, so who can we give money to and what can we do with our money to just make people happy and make people like us?’”

Maddux liked throwing money at TinyLetter. It was pretty effective, especially garnering goodwill from journalists who are, at their core, writers. Her team gifted custom ceramic mugs to writers (disclosure / brag: I got one). They sent writers to the Decatur Book Festival in Atlanta. In 2014, there was even a residency program, where TinyLetter funded a dozen writers, including Jia Tolentino, Britt Julious, and Michael Twitty, at the Ace Hotel in Palm Springs. (“spent it working on a bad novel that i ended up shelving, and it was really fun,” Tolentino emailed me. Her TinyLetter was a regular Soundcloud playlist called Tiny Bitch Tapes.)

Eventually the wild, creative days at Mailchimp matured into a more staid, workmanlike office culture. Marketing got less “vibes”-based and more product focused. By 2017, Maddux wasn’t working on TinyLetter anymore — it’s unclear if anyone was. Mailchimp was now focused on its core newsletter offerings and the enterprise customers they could actually make money from. Eventually, Intuit, the company behind financial tools like TurboTax, Mint, and Credit Karma, bought Mailchimp in 2021 for $12 billion.

Much of the acquisition happened during Maddux’s parental leave a year later. “When I got back, things were about as far as you could get from where it started,” she says.

To Maddux, the change within the company was gradual, but also predictable: the story of a tech startup that started scrappy and simply got bigger. “I was a writer primarily identifying as a writer, working at a tech company, so I kind of felt just like a weirdo all the time,” she says. “I was constantly forgetting that the goal was to make money and not just have a good time.”

She left Mailchimp in 2023.

Today, the company most associated with email isn’t Mailchimp, but Substack.

Substack figured out that it didn’t need to make money primarily from the people sending the emails, but from the people receiving them. A growing number of independent “creators” were making a living through platforms like Patreon. The early days of Substack offered a mostly undifferentiated newsletter product, except with easy subscription and monetization tools. 

It’s easy to see the bones of Substack in TinyLetter. Mailchimp had encouraged writers to take the newsletter medium seriously; Substack offered them ways to profit from that. But with money comes expectations: to write for an audience, to prove value, to deliver. As it rapidly expanded — buoyed by gobs of venture capital — Substack’s recommendation features powered its rise and also warped the incentives. Has a pitch for the platform ever involved something other than growth and money?

Often for writers, the benefits and privileges of publishing are greater than the ability to monetize. Few writers I know would call themselves “creators,” and even fewer would say they produce “content.” Much of the personal writing that thrived on TinyLetter would never make money on Substack. And besides, not everything in TinyLetter plumbed the depths of the human experience. There were a number of narrow concepts and jokes, perhaps spiritual siblings of the single-serving Tumblr.

In many ways, TinyLetter embodied the idea that creativity comes from constraint. (The UI is more sparse than, say, Microsoft Word.) Writers could express their weirdest selves. Sometimes it was that inanity or specificity that could jump-start careers or turn into books.

Culture writer and Verge alum Kaitlyn Tiffany claims she got hired by The Atlantic because the executive editor was a subscriber to her TinyLetter about Jake Gyllenhaal, Our Bodies Are Controlled by the Moon. Author Alexander Chee’s early emailed essays on writing craft became the foundation for his award-winning collection How to Write an Autobiographical Novel. (Chee’s agent, a subscriber to his newsletter, used the archive to compile a draft of its table of contents.) Charlotte Shane collected Prostitute Laundry into a book, which she funded on Kickstarter and self-published. (This summer, she has a memoir coming from Simon and Schuster.)

It was December 2015 when Claire Carusillo was bored at her social media editing job when she started My Second or Third Skin to roast egregious skincare products. She described her writing as “unbridled.” “I got a lot of paid freelance work that way, and without the TinyLetter, even though I was doing that for free, I wouldn’t have built these relationships with editors. I wouldn’t have been able to survive as a freelancer in New York City without doing the TinyLetter because of the reach that it had,” she says.

Carusillo stopped doing her newsletter when she joined the stable of writers for the Gawker reboot. In the year since she was laid off, she has been trying to make a paid Substack account work. So far, it’s been untenable. The math just doesn’t work out.

“The infrastructure’s broken. I don’t know if it’s oversaturated or I don’t know if it’s the sort of stigma that Substack has developed in the last year, but the magic’s gone,” she says.

It’s easy to see TinyLetter as an opportunity that Mailchimp didn’t seize. But given the tensions between content moderation and free speech that have mired Substack recently — especially whether or not the platform is willing to host Nazi content — maybe Mailchimp leadership is glad to be associated with boring old marketing emails instead.

Besides, that magic Carusillo describes, the one TinyLetter captured for a brief moment, has been elusive.

“It was so special back then that I would get emails from people who were reading [my TinyLetter], and I would have special little email friendships with people,” she says. “A lot of my real life friends came from people who were reading the TinyLetter, and I think that that’s gone. It’s totally gone. I don’t know if we can recreate it.”

In the past, I’d been able to speak directly to the folks at Mailchimp just by emailing them. When I followed up for comment on this piece, I was surprised to get bounced to an outside publicist, who was reluctant to put anyone on the phone with me. She was apologetic, attributing the company’s busy schedule to a move to a larger corporate office in Atlanta. I was sent a press release about it — a new 360,000 square-foot “innovation hub” with “over 100 conference, huddle and team project rooms, plus drop-in rooms.”

With regards to TinyLetter, I got a corporate statement, to be attributed to Jon Fasoli, chief design and product officer at Intuit Mailchimp:

It was as corporate a statement as they come. (Fasoli joined Mailchimp in 2021 — many years after the TinyLetter acquisition.) Though it was vague on details, the message was clear: Mailchimp is a different place now. The one that supported TinyLetter no longer exists.

After all, TinyLetter was, as Kaplan put it, just a sign-up form and a loop that sends emails over and over. From a technical and product standpoint, that is still true. And yet, even a decade later, from within a decaying media ecosystem that increasingly treats every story as indistinguishable pieces of “content” and an internet being consumed by a torrent of AI spam, the smallness of TinyLetter still feels like it was so much more than that. I don’t know if the platform created a moment unto itself, or if it was the last gasp of a certain kind of internet writing. All I know is that as TinyLetter sunsets, something dies with it.

When I talk to Maddux, she is similarly wistful but more understanding. At least the thing she worked on didn’t turn into Substack. “I would rather a platform peter out due to benign corporate neglect than what feels like mass exodus due to Nazis,” she says.

To her, the history of the internet is about platforms having specific moments, and sometimes, it’s okay to just let those moments pass naturally. TinyLetter lived briefly and died slowly. And on the internet, that’s about as good as it gets.