Tips On Crafting A Popular Newsletter, From Top Newsletter Authors

A look at the six most popular newsletters on TinyLetter and what they’re doing right.

Tips On Crafting A Popular Newsletter, From Top Newsletter Authors
[Image: Flickr user Stylianos Mystakidis]

So you want to start a newsletter. The medium is having a moment, a phenomenon even the New York Times‘ esteemed media critic has noticed. The time to jump on the bandwagon, before #brands take over and ruin everything, is now.


But how? Fast Company spoke with TinyLetter, the platform of choice for newsletter writers, about what aspiring email tycoons can learn from its most popular emailers.

These are the six most popular and influential personal newsletters, in no particular order, according to TinyLetter’s internal numbers.

“Popular” in newsletter terms means a thousand subscribers and up–puny by social-media standards. Since email is such a sacred space, subscribers are hard-won. Getting even 1,000 subscribers on TinyLetter is a lot more difficult than accumulating Twitter followers. “Ten thousand subscribers is a really big list for a personal email newsletter,” says Kate Kiefer Lee, an editor at MailChimp, which owns TinyLetter. “A lot of influential writers on TinyLetter have lists in the high hundreds or low thousands.” The average TinyLetterer has only 265 subscribers.

That said, those modest-sounding subscriber lists can still generate lots of traffic to the content newsletters promote. What newsletters lack in followers, they make up for in loyalty. Alexis Madrigal’s 5 Intriguing Things has 8,800 subscribers, for example, a small fraction of the people the Deputy Editor can potentially reach on Twitter. His newsletter open rate, however, hovers around 60%. “I can reach 5,280 (people) every day, roughly,” he told Fast Company. “You’d need a Facebook page with 88,000 likes to do something like that.”

So far, TinyLetter doesn’t offer any direct way for writers to make money off of their newsletters. The most apparent benefit is personal branding. Newsweek syndicates Rusty Foster’s popular media roundup Today in Tabs. Foster has also landed a few profiles for being an email pioneer. Journalist Ann Friedman started hers to reach readers after the death of Google Reader.

Someone with a large following could potentially use the platform to hawk a book or get people to attend a conference, but Kiefer Lee says readers don’t particularly like that. “People like getting what they signed up for,” she said. “If they sign up for a personal email newsletter, they don’t want to be marketed at.” Of course, the difference between “marketed at” and self-promotion isn’t always clear.


So then what do readers like?

Newsletters cater to people who want to stay informed without feeling like a slave to the Twitter stream–all the news you can use is waiting in a hand-crafted email sitting in your inbox. The three formats that tend to fit that mold and therefore collect the most followers are: digests, like Friedman’s roundup of the articles she’s written or is reading; curation, like the tabs Foster collects; and single topics, such as newsletters about intellectual property like “5 Useful Articles.” Personal newsletters, like the intimate emails writer Kevin Nguyen sends every other Friday, are also popular. Humor helps. “People who obviously just really have fun with their newsletters and write in the way that they talk, those people generally do really well with newsletters,” Kiefer Lee said. A newsletter is different than a publication. People like informality.

As far as scheduling goes, the most popular newsletters all operate on schedules ranging from every day to bi-monthly. Power news consumers, like yours truly, might want something that comes every day, while others will appreciate restraint. Kiefer Lee suggests that writers only commit to doing as much as they can without sacrificing quality.

The hardest part of newslettering is building an audience, because of the aforementioned “email is sacred” thing. “Start with your inner circle,” Kiefer Lee suggests. For most people that means sharing it on Twitter, and putting a link in your Twitter bio. “If your newsletter is good, people will share it. It will grow over time,” she says.

Madrigal, who it should be noted has a high profile in the Internet world and a very big social media following, said his growth has come in bursts. Links from media outlets like Daring Fireball have sent him chunks of subscribers. Otherwise, it has been a slow build through dedicated fans sharing the newsletter on Twitter and with their friends. “The main thing is: newsletter strategy takes time. It’s not viral in the same way as a Facebook thing.”


About the author

Rebecca Greenfield is a former Fast Company staff writer. She was previously a staff writer at The Atlantic Wire, where she focused on technology news.