Tinyletter was one of the greatest missed opportunities in tech

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The last year has been a good one for newsletter publishing platform Substack. After securing a $15.3 million funding round in July 2019, it went on to lure hundreds of high profile writers onto its service. In late 2019, a group of prominent never Trumpers from the National Review and Weekly Standard banded together to launch a magazine on Substack. In April, celebrity journalist Matt Taibi announced that “from now on, my online writing will be published on Substack. This is my full-time job now.” 

And earlier this month, Substack landed its biggest writer yet: Andrew Sullivan. The longtime blogger and columnist, after indicating that he had been pushed out of New York magazine, revealed in his goodbye column that he was relaunching his famed blog The Daily Dish as a Substack newsletter. Shortly before this news was announced, Substack’s founders told a tech publication that newsletters on its platform have collectively converted over 100,000 paying subscribers.

It’s clear at this point Substack is one of the main beneficiaries of a paradigm shift in which more and more writers are attempting to monetize their content directly. Nary a day goes by without a verified user on Twitter announcing they’re striking off on their own by launching a newsletter, and Substack now counts at least a few dozen users who are generating six figure incomes.

But every time I read about Substack’s success, I can’t help but think of another platform that seemed to enjoy similar momentum just a few short years ago: Tinyletter. Like Substack, Tinyletter provided an easy-to-use tool for sending newsletters, and it had the kind of organic adoption from highly influential web writers that most new publishing platforms can only dream of, and yet today, a few short years after its peak adoption, hardly anyone of note uses it. What’s more, I don’t think its parent company Mailchimp even cares. As an early Tinyletter user myself, I can’t help but think of it as one of the greatest missed opportunities in tech.

Tinyletter was founded in 2010 by Philip Kaplan, an entrepreneur who’s well-regarded in Silicon Valley. According to a TechCrunch article reporting on its launch, Kaplan coded the site in a single day. “He felt like resurrecting the email newsletter because he didn’t want to put the work into writing a blog,” paraphrased TechCrunch’s Leena Rao. “His point is that if you don’t blog daily, you won’t build an audience, but email newsletters can be sent out weekly and have a built in audience. And people check their email everyday.”

Several other newsletter platforms existed at this point, but Tinyletter’s appeal lay in its barebones simplicity. It looked like a blog CMS, had a very basic design, and featured none of the fancy bells and whistles found on other services aimed at more sophisticated email marketers. You couldn’t segment lists, A/B test subject lines, or schedule drip campaigns. You just typed your words into a box and hit send. 

It also didn’t hurt that it was completely free. Most email marketing companies operate under a SaaS structure, charging larger and larger amounts based on the size of your email list. Companies that utilize email to sell products are often happy to pay for that service, but most writers didn’t have the money or the technical know-how to utilize the sophisticated offerings of a Mailchimp or Constant Contact. They just wanted an easy way to email their fans, and Tinyletter provided it.

About a year after Tinyletter’s launch, Mailchimp acquired it for an undisclosed sum. An AllthingsD article about the acquisition reported that the platform hosted about 30,000 newsletters and sent out “about one million emails a month.” I have no idea who its earliest adopters were, but over the next few years it began to attract some pretty high profile writers like Digg co-founder Kevin Rose and tech journalist Alexis Madrigal. Just as I can’t open Twitter today without seeing announcements for new Substack newsletters, it seemed like everybody circa 2013 was posting a link to their newly-created Tinyletter. That year Fast Company reported that 100,000 people had signed up, and 4,000 of them were sending out newsletters at least once a week.

Why were so many people suddenly interested in this super simple publishing tool? The company’s founders noted to Fast Company’s Rebecca Greenfield that the service experienced a jump in users that corresponded with the death of Google Reader -- an indication that maybe people were looking for a new way to be updated when their favorite writers posted something new.

But Tinyletter also benefited from a veritable resurgence in the email newsletter, a format that many assumed had reached its peak sometime in the early 2000s. The late David Carr reported in 2014 that “email newsletters, an old-school artifact of the web that was supposed to die along with dial-up connections, are not only still around, but very much on the march.” 

This renewed interest in newsletters was, I think, a backlash against the publicness of social media; even back then we were starting to understand the power wielded by huge platforms like Facebook and that we relied on them too heavily for content distribution. Email newsletters benefited from decentralized delivery and felt more intimate. In 2016, I published a piece comparing newsletters to the indie print zines that flourished in the 80s and 90s. Entire zine-like subcultures sprouted up on Tinyletter. For instance, The Guardian reported that “TinyLetters dedicated to short stories, poems and other more esoteric forms offer an accessible route into genres that can feel opaque and unreachable.”

I don’t know how many users Tinyletter had at its height, but Wired reported in 2015 that 141,000 accounts sent newsletters to a combined 14 million subscribers. That’s impressive! But then in 2017 Substack launched, and before long users began moving their newsletters over to this shiny new platform. One of the great things about Tinyletter (and most newsletter services) is that you can easily download a spreadsheet of your subscribers and, with a few clicks, be up and running on a different platform. Today, if you perform a Twitter search for the words “moved,” “Tinyletter,” and “Substack,” you’ll see hundreds of blue checkmark users announcing their migration from one platform to the other. It was the greatest user exodus since Digg’s entire audience picked up and moved to Reddit.

So why did it happen? Well, for one, Substack offered its writers the ability to charge their email lists money for a subscription. For reasons I’ll explore more in a moment, Tinyletter never showed any interest in helping its users make money. In fact, it eventually cost them money, since it was only free to use for the first 5,000 subscribers. After that, it forced you to switch to a paid Mailchimp account.

Imagine what this was like for a Tinyletter user. You’re seeing some success on the platform, and then suddenly you’re transferred to a different, much more complicated service, one that requires you to shell out up to hundreds of dollars a month if you want to continue using it. I’d imagine it was a pretty jarring experience!

Ultimately, Tinyletter’s downfall was rooted in its lack of innovation. During my couple years on it I don’t remember it rolling out a single product update. Sure, the simplicity was nice, but it could have used more publishing tools and a better presentation on the web. One great thing about Substack is the web version of your newsletter looks really nice and displays well on social media. Its founders basically took Medium’s sleek aesthetic and added newsletter functionality. 

The worst thing about Tinyletter, in my opinion, was its overly aggressive “abuse” filter. If you used a single word that this filter deemed as problematic or spammy, then Tinyletter would lock down your ability to send out the newsletter until a human staff member could review it and unlock your account. The process was infuriating. I remember sometime in 2019 I tried to publish a newsletter about affiliate marketing, and because the filter likely thought the word “affiliate” was too spammy, it put me in Tinyletter jail. It was the straw that broke the camel’s back; that same day I opened a Substack account.

It’s pretty clear at this point that Mailchimp had no interest in investing any time or money into Tinyletter. In fact, it confirmed as much when, in 2018, Inc reported that Mailchimp planned to sunset the platform. After user backlash, Mailchimp CEO Ben Chestnut released a statement that pushed back on Inc’s reporting, but he ultimately acknowledged that “in the long term, we do intend to integrate TinyLetter into MailChimp.” Right now, if you visit the Tinyletter homepage, it still encourages you to sign up for an account, but I doubt many people are. To test this theory, I plugged both tinyletter.com and substack.com into Twitter search. In the last hour, three Twitter users have posted links to Tinyletter articles. For Substack, the number was 58.

Which leaves us with one final question: why? Why turn your back on a community of passionate users? Why not try to compete with another company that landed on an innovative business model? Why pass on the opportunity to lead the paradigm shift toward entrepreneurial journalism?   

It’s because Tinyletter’s and Mailchimp’s businesses were never aligned in the first place. Chestnut even acknowledged as much back in 2011 when he announced the acquisition. "Basically, TinyLetter is for people what MailChimp is for business." Mailchimp’s VP of communications Kate Kiefer Lee told Wired in 2015 that there’s little to no crossover between Tinyletter users and Mailchimp customers. In other words, Tinyletter didn’t even serve as an effective form of lead gen.

That’s because it was geared toward individual writers. Mailchimp is an enterprise SaaS marketing product. It wants to land small, medium, and large businesses that will pay up to thousands of dollars a month to access its suite of tools. Tinyletter targeted the Alexis Madrigals of the world; Mailchimp targets the Walmarts. 

So what may have seemed like the perfect synergy ended up being anything but. Because of Tinyletter and Mailchimp’s mismatched priorities, Substack is now leading the charge to connect every writer to their thousand true fans. And while I’m perfectly happy for Substack to lead that charge -- this newsletter, after all, is distributed through Substack -- I can’t help but feel a little bit of nostalgia for the era when I’d get excited to send out my Tinyletter each week. The company helped kick off a newsletter renaissance; now it has to sit back and watch as other platforms profit from it.

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Simon Owens is a tech and media journalist living in Washington, DC. Follow him on TwitterFacebook, or LinkedIn. Email him at simonowens@gmail.com. For a full bio, go here.

Creative Commons image via Needpix