The Peculiar Rise of the Paid Email Newsletter

Email-based newsletters have existed in some form or another for decades — it is the origin story for now-giant websites like the Drudge Report and Fark — but I think the current boom of paid subscriptions owes itself to the success of Ben Thompson’s Stratechery. I have been fascinated by this format’s rise in popularity for years because I loathe email; yet, it makes complete sense to me from the perspectives of both a publisher and a reader.

First, from the publishers, Casey Newton, who has been writing the Interface newsletter for several years at the Verge and is now going solo:

The launch of Substack in 2017 has made turning a newsletter into a business radically easier. It has been thrilling to watch reporters like Judd Legum, Emily Atkin, Alex Kantrowitz, and Anne Helen Petersen turn their journalistic passions into independent businesses. I’m so grateful to be able to have learned from their experiences to date, which have informed and hopefully improved my own tiny media company ambitions.

For the past few months, I’ve been building Platformer, a new publication about tech and democracy. A platformer is a video game in which the character leaps from surface to surface, dodging various obstacles along the way to reaching their goal. That more or less describes my life as a writer on the internet over the past decade. But it also feels like as good a metaphor as any for understanding life online as this decade unfolds.

Marc Tracy, New York Times:

Most Substack writers offer a mix of paid and free email newsletters. They make money through subscriptions, not ads. Writers own their newsletters, and the platform takes a 10 percent cut. Substack also offers a legal defense service to writers of paid newsletters in the United States.


[Substack CEO Chris] Best said Substack’s reliance on email — rather than social media or search engines — promoted a one-on-one relationship between writers and readers, something that should be prized at a time of online noise.

One of the hardest aspects of writing on the internet is developing a core audience of people who will make a daily task out of reading your website. Website feeds have long been a good way to alert subscribers of something new, but they need to be explained, so they aren’t great for reaching a wide audience of varying technical ability. For a brief moment, it seemed like automatic delivery of links through pages on Twitter and Facebook would be a good in-between answer, but their constant fiddling with feed contents based on unknown user metrics severely hampers reliable delivery to subscribers.

Email is a great lowest common denominator solution. It is an open standard that everyone already knows how to use. An email client is a feed reader without a learning curve.

A few weeks ago, Tom MacWright explained how the web has bifurcated into document-based websites and web apps. Apps based on web technologies are commonplace and, though I dislike them, are immensely popular for their cross-platform appeal. However, every technology that enables the creation of better web apps can also be used to turn the document-based web into a bullshit web experience. MacWright’s proposed solution was to sever the two approaches with a new Commonmark-based markup language for document sites.

That is a radical proposal, but it is accidentally being implemented, sort of, with email newsletters. Anyone who has ever built an HTML email template can tell you that rendering engines in email clients are an inconsistent and catastrophic mix of website development eras. The safest route is to build HTML emails like you’re building a webpage in about 1997. Which, yes, is awfully limiting from a design perspective. But that also means there’s no JavaScript, no complex CSS, no scrolljacking, no time-on-page metrics, limited analytics, and virtually no surveillance. That’s not an accident; email is private, and most clients still treat it that way despite Google’s best attempts.

Email gives publishers — whether they are individuals or collectives — a more direct relationship with their audience and, not coincidentally, a more direct revenue stream. But both of those things are true of websites. Why do paid email newsletters seem to be succeeding where website paywalls struggle? I think Best is right: email is a more intimate medium than a website. Even though you know you are just one row in a database, it feels like the author is contacting you directly. Also, because email is an inherently private space, I think it feels more attuned to being locked-down than the more open web.

Yet, despite all of these clear advantages, I still find it difficult to think of my email inbox as somewhere I will go to find something enjoyable to read. I still think of email as a one-to-one communications method, or a place where I find receipts, see that stuff is on sale, and read some press release. For the vast majority of newsletters that I’m subscribed to, I use my Feedbin email so I can read them alongside all of my other subscriptions. Perhaps the growing email newsletter market explains the seemingly parallel ascendence of email clients that go beyond a single inbox view.

It seems almost tragically ironic to think that newsletter subscriptions are the future of independent publishing. Email has been around for far longer than the World Wide Web, and has almost none of the design advantages or surveillance mechanisms celebrated by web publishers. All this time we have been subject to the whims of ad technology firms when the solution seems to be a rewind button.

As a minor solo publisher, I don’t know that an email newsletter makes sense for what I write. Anyone who wants to give me money for my efforts is free to do so and also very kind, but I like that anyone can stumble across my corner of the web. That is the trade-off of having a freely-available open presence: more people can see it, but I cannot imagine that this could become a career. And that is why many serious independent writers have paywalled newsletters.