TinyLetter: looking back on the humblest newsletter platform

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.

“What if we made no money? What if money wasn’t even something we were thinking about?”

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…



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