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Not a Newsletter

Not a Newsletter: February 2021

Welcome to the February edition of Not a Newsletter, a monthly, semi-comprehensive, Google Doc-based guide to sending better emails! I’m Dan, the founder of Inbox Collective, an email consultancy, and the former Director of Newsletters at The New Yorker and BuzzFeed. Every month, I update this doc with email news, tips, and ideas. Sign up here to be notified when a new edition goes live!

Inside this edition: Why the email backlash is coming (again) in 2021; newsletter success stories from Argentina, Canada, and Poland; new Course launches; ten new email jobs in cities including Philadelphia, Nashville, and Denver; and more!

One of the advantages of a Google Doc is that it makes it easy to read and search through older editions of Not a Newsletter. You can find the full archive at this link.

-Dan 

(Email / Twitter / LinkedIn)

Two dogs watch a human work at the computer. One says to the other: "They're bred to stare all day."
Mike Twohy / The New Yorker

This Month in Email Headlines

The Email Backlash is Coming. (Again.)

I remember the last time email was cool.

It was 2014. TheSkimm was the biggest thing in email — that year, Oprah tweeted her endorsement (Oprah! Endorsed! A newsletter!), and then TheSkimm announced a $6.25 million Series A round. That got everyone’s attention.

There were other big things happening in email that year. Google announced Inbox. At BuzzFeed, we were about to cross two major thresholds: 1 million subscribers and 5 million clicks a month from our newsletters. Many, many people launched TinyLetters. David Carr of The New York Times wrote: “It gives us great pleasure to reveal a radical publishing technology that is catching on in news media companies big and small. Ladies and gentlemen, behold: email.” It had never gone away, but email was suddenly back.

And then an odd thing happened, something I hadn’t experienced before: People started announcing that email was dead.

There were all sorts of reasons for it. Companies like Slack used the death of email as a talking point in interviews. (Slack’s Stewart Butterfield called email “the cockroach of the internet,” which oddly just reinforced the idea that email wasn’t going anywhere.) Brands investing in newer channels described email as outdated. Contrarians proudly announced that we’d hit peak email, and that the platform was on its last legs.

Despite those predictions, the email world kept moving forward. There wasn’t quite as much fanfare about it, but in the years after that 2014 boom, lots of newsrooms, non-profits, brands, and individuals kept investing in email. Newsletter tools got better, too, as new partners entered the space to help people send better email.

And then five years after the last cycle, email was officially back (again), and bigger than ever (again).

In the past year, Substack became a household name. Bootstrapped newsletters like Morning Brew and The Hustle, inspired by TheSkimm’s launch during that 2014 boom, were acquired for a combined $102 million. Twitter purchased an email platform. The New York Times’s daily newsletter hit 1 billion emails opened.

It was an incredible year for the world of email.

Which means that 2021 is going to be the year that email died — again.

You’re going to read a lot about the death of email this year. “Why I left Substack” posts will be the new “Why I left New York.” Some new technology will become a media darling. (The next time you’re on a family Zoom call, ask your teenage cousin to show you their phone. The hot new app of 2021 is probably on there already.) Expect Twitter threads and LinkedIn poetry about why this time, truly, it’s time to say goodbye to email.

But just like back in 2015, email will keep moving forward. Email’s not dead, and it’s not going anywhere. I’m seeing entrepreneurs in Asia, Australia, and South America, inspired by the success of digital-first products like TheSkimm, Morning Brew, and The Hustle, launching their own newsletters to serve local markets. I’m seeing experts continue to use email to build an audience — and a business — to share their expertise. I’m seeing writers and creators using email to connect people and serve readers around the world. I’m seeing opportunities for subscription products, for ad-driven newsletters, for emails with digital courses, workshops, or even consulting as the primary revenue source.

Don’t get discouraged by the negativity that’s coming in 2021. It’ll pass, leaving you — the people out there building great newsletters to serve your communities — left to do the work, quietly, out of the spotlight. Newsletters are rarely an overnight success — they’re usually a slow burn. Where you’re headed is far more important than how fast you get there, and I believe that if you’re investing in email, you’re on the right path.

Yes, the backlash around email is coming this year. There’s not much we can do to stop it. But remember: We’ve been here before.

“Email has had a good run as king of communications,” wrote The Wall Street Journal’s Jessica E. Vascellaro, in a widely-quoted piece about email’s coming demise all the way back in October 2009. “But its reign is over.”

You may better recognize Vascellaro under her current byline: Jessica Lessin, founder of The Information.

She now writes an excellent weekly newsletter.

For Your Reading / To-Do List

They also changed the way they defined and cultivated engagement. Rather than seeking to create public “debates” on their platforms, which would usually devolve into fights, they focused on cultivating 1:1 interactions through replies to the newsletter, where they could disagree but still have a conversation. Although these 1:1 conversations were more time consuming, they were also more rewarding for both Outride.rs and its readers. The staff started paying attention to engagement metrics such as how many people replied to the Brief each week and whether each person received a reply. 

  • You’ll hear me say this over and over again in 2021: Email is about relationships. Ask your readers questions. Write back to them. I did the same in my days at The New Yorker — most days, the very first thing I did at the office was to spend time writing back to readers. I promise, it’s time well spent!
  • In Laboratorio de Periodismo, Agustina Heb interviewed Abel Escudero Zadrayec about why he launched a local newsletter, 8000, to serve the community in Bahía Blanca, Argentina. (The article’s in Spanish, FYI.) Based on the conversations I’m having with Not a Newsletter readers outside of North America, expect to see more of these local news launches in the next year.
  • Even more non-U.S. newsletter stories for you: Quebec’s La Presse walked the Facebook Journalism Project’s David Grant through their remarkable 2020, in which they added more than 150,000 email subscribers and raised more than $5 million from readers.
    • Full disclosure: I’ve been a speaker at several Facebook Journalism Project Accelerators, and have been paid for my work there.
  • Over at the Napkin Math newsletter, Adam Keesling broke down why local news newsletters represent a huge opportunity in 2021 and beyond. (More on this to come in the next few weeks — I’ve been interviewing several local newsletter operators for a story about the space!)
  • If I could buy a billboard in Times Square to share one crucial message for 2021 about email, it’d probably feature these words from Kaleigh Moore of ConvertKit: “You don’t need a giant email list for a successful launch.” She talked with four creators who saw huge success in selling products and classes to small audiences.
  • Arizona newsletter #ThisIsTucson launched an eight-part Course to help new residents navigate their city. They talked with the News Revenue Hub about how they put together the project. (I love the concept here — in fact, a few of my  teams are working on their own “Welcome to _____” Courses for their local markets right now!)
  • Exciting to see publishers test out Courses in other ways, too. Here’s a Coursera-style offering from Front Office Sports (full disclosure: They’re an Inbox Collective client) that they launched in tandem with Pepsi.
  • Hanaa’ Tameez of Nieman Lab talked with Subtext’s Mike Donoghue about opportunities in the text messaging space. And on the note of 1-to-1 discussion: These text threads are also a great way to start conversations. The more you seek to build relationships with readers — whether through newsletters, texts, or another channel — the better your products will perform in the long run.
    • It’s exciting to see local newsrooms test out text-based initiatives. Here’s a smart one from The Boston Scope around COVID-19 news.
    • On a related note, this headline from MediaPost caught my eye: “Study: Newsletter Readers Want Push Notifications For Breaking News” My take: These are complementary tools, not competing ones. You might break news via text or push notification, but then break down the details the next morning in your daily newsletter. Or a reporter in your newsroom might dip their toe into audience engagement via text message, and then launch their own newsletter to bring that 1-to-1 mindset to the inbox. There’s no reason why you shouldn’t consider both channels as part of your strategy to build relationships with readers.
  • So many people are running Zoom-only events these days. If you’ve got an event launching soon and need help including those “add to your calendar” links to your newsletter, Carin Slater of Litmus has a tutorial to help.
  • On the Stripo blog, Dmitry Kudrenko shared a few examples of how to use AMP for Email to build games and puzzles into an email. For those interested in AMP, I’d bookmark this one for later.
    • And if you’re wondering, “Can I do this with my newsletters, too?”, first look at AMP’s supported ESPs and email clients. Many Not a Newsletter readers, unfortunately, are on platforms that don’t yet support AMP.
  • I really enjoyed this interview that Simon Owens did with Ernie Smith, creator of the Tedium newsletter (and the man behind the excellent Newsletter Nerds Facebook group).
  • A little while back, many Not a Newsletter readers contributed to a survey about which tools media companies use to manage their workflow. I promised to follow up with the results — here they are!
  • Dela Quist, a true expert in the email space, wrote about why subject line testing is so crucial to long-term reader engagement.
  • Some good tips here, from Kelly Forst on the AWeber blog, about how to send a proper apology email.
  • On UX Collective, Nick DiLallo shared copywriting tips for new digital products. I particularly loved some of the microcopy examples in here — lots of good tips if you’re working on pop-ups or marketing copy right now.
  • And lastly: If you didn’t get enough of me in Not a Newsletter this month, I talked with Mae Rice of MarketerHire about 10 things marketers get wrong about email.

Stuff I Loved This Month

  • Back in spring 2020, I helped the team at WordPress think through a new plugin that would allow publishers to send simple newsletters straight from WordPress. They’ve been testing it out for a few months with several publishers, but that plugin is now available to all WordPress users! You can download the plugin here, and read a review of the plugin here.
    • Of note: Right now, this is only compatible with Mailchimp and Constant Contact, and it offers a handful of templates, including a breaking news template, a daily newsletter template highlighting a few recently-published stories, and a template to drive readers to support your work. If you’re a newsroom that frequently sends in those formats, it might work well for you!
    • Here’s an example of a daily newsletter powered by the new plugin (this one’s from the Evanston RoundTable, who I’ve been working with through Inbox Collective).
  • Launching this February: Joseph Lichterman, Caroline Porter, and Emily Roseman — who’ve all done excellent work in the email space! — are launching a free online course about newsletters. If you’re just getting into email and want to learn from experts in the space, sign up here!
  • I stumbled on this (thanks to the excellent Really Good Emails newsletter), from Julia Evans: A blog post highlighting six myths about email newsletters. This sentence from Julia is spot on:

When I started, I was really convinced that email marketing was this terrible, awful thing that I could not do that mostly involved tricking people into getting emails they don’t want (ok, I’m exaggerating a bit, but I really struggled with it). But it’s possible to do it in a transparent way where I’m mostly just sending people helpful emails that they do want!

The Google Docs Anonymous Animal of the Month

One of the quirks of publishing in a Google Doc is that when readers like you visit, Google identifies you as an animal in the top right corner of the doc. So to close out this edition of Not a Newsletter, I want to spotlight one of the Google Doc animals in a feature I call… the Google Docs Anonymous Animal of the Month! This month:

the Goose

Anyway, the Goose! That’s your Google Docs Anonymous Animal of the Month. 

Here's a decorative image of three animals: An owl, a flamingo, and a seahorse

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By Dan Oshinsky

Dan runs Inbox Collective, a consultancy that helps news organizations, non-profits, and independent operators get the most out of email. He specializes in helping others build loyal audiences via email and then converting that audience into subscribers, members, or donors.

He previously created Not a Newsletter, a monthly briefing with news, tips, and ideas about how to send better email, and worked as the Director of Newsletters at both The New Yorker and BuzzFeed.

He’s been a featured speaker at events like Litmus Live in Boston, Email Summit DK in Odense, and the Email Marketing Summit in Brisbane. He’s also been widely quoted on email strategies, including in publications like The Washington Post, Fortune, and Digiday.