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Not a Newsletter

Not a Newsletter: October 2022

Welcome to the October 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 the next edition goes live!

This month: What happens when Stripe + Substack isn’t an option in your country? One India-based writer found a fascinating solution. Plus: How to use Facebook ads to drive newsletter growth; why you need to build a clear workflow to eliminate email errors, and what to do if you make a major mistake in a newsletter; and a question about email workshops that I’d love you to answer.

Want to read a previous edition of Not a Newsletter? Find the full archive at this link.

-Dan 

(Email / Twitter / LinkedIn)

Two men talk at a table. One asks: "Why don't you try a grand gesture, like a well-written email?"
Brendan Loper / The New Yorker

This Month in Email Headlines

New on inboxcollective.com

When Stripe + Substack Weren’t An Option, This Writer Got Creative

Substack, like many digital tools, doesn’t actually process credit card payments. They rely on a third party, Stripe, which works in 47 countries around the globe. But if you’re a writer based in India, Stripe won’t let you set up an account, which makes collecting recurring payments from readers a complicated, and often manual, process.

Rega Jha,  the former editor of BuzzFeed India, figured out a clever workaround. And ultimately, it led to her launching a new type of paid newsletter — a pop-up product where readers pay up front to read a season of the newsletter. Here’s how her newsletter, “Small Scenes,” works.

How to Send an Apology Email

If you send enough email, you’re going to make mistakes. Sometimes, there’s a typo in an email, or a broken link, or placeholder text that doesn’t get replaced. The good news is: There are strategies you can implement to prevent many common email errors. And if you do make a mistake, there are ways to make things right with your audience.

Here’s how to build a pre-send checklist that helps you prevent errors, and here’s what to do if you make a mistake (especially a big one). Before you hit send, read this.

Which Metrics Do I Need to Monitor When It Comes to Deliverability?

Keep an eye on spam complaints and inactive readers, per our deliverability expert, Yanna-Torry Aspraki. They’re among the signals that matter most when trying to stay in the inbox. Here’s what else Yanna-Torry recommends.

You can now sign up for an email alert when we publish something on a topic you care about. These emails are really brief, and sent only when we publish in a topic area of your choosing. Just make sure you sign up with the same email address you already use for Not a Newsletter, and I’ll handle the rest!

[Sign up for alerts]

For Your Reading / To-Do List

  • It’s been a year since Apple rolled out Mail Privacy Protection. If you’re reading this, you’ve long known about the impact MPP has had on open rates. But there’s another new set of challenges coming — as Heather Goff writes for Oracle’s blog, the combination of MPP + some changes from Spamhaus (the org that maintains various blocklists for mailboxes) could spell trouble for high-volume senders in the months ahead.
  • How can you use Facebook ads to drive newsletter growth? I really enjoyed this walkthrough from Paved, which is aimed at those who’ve never run a paid acquisition campaign before.
  • Bloomberg News, like a lot of newsrooms, has quite a bit of ad inventory available on its website. They sell most of these ads themselves — for Bloomberg, that might include reputable brands like American Express or IBM. But about five percent of their ads have been sold by third parties, with each ad shown making Bloomberg a fraction of a fraction of a cent. And these ads feature advertisers that are… far from reputable. (If you’re not sure what I’m referring to, Google “chumbox.”) The ads don’t generate much revenue and they don’t fit in with the other advertising on site — so why run them? Bloomberg announced that they no longer will, and better yet, they’ll be using that unused ad inventory to promote Bloomberg products, like newsletters. This is a recommendation I’ve been making to my clients for years, and I’m thrilled to see Bloomberg make this change, too. Others should follow.
  • Recently here in the Google Doc, I shared a few links about Google’s plan to keep emails from American political campaigns out of the spam folder. For those who haven’t been following along, here’s what you need to know:
    • There are lots of agencies and consultants that work with political campaigns. Some follow best practices for email deliverability: Authenticating their emails, making it easy for readers to unsubscribe, avoiding shady subject lines or sent-from names. Many do not.
    • And you might be wondering: Dan, how shady could some of these tactics truly be? Here’s a good example: Earlier this year, I got a fundraising email from a candidate where the sent-from name read, “Flight confirmation,” and then included a fake confirmation number. The inside of the email was, in fact, not a receipt from a flight I’d booked, but an email begging me to donate to a political campaign. (It had absolutely nothing to do with a flight — the sender used that subject line because, correctly, they predicted I’d open that email.)
    • When you’re sending shady emails like that, your emails tend to go to spam — and that’s exactly what happened to a lot of these candidates.
    • Those political campaigns then complained to these agencies/consultants that their emails were going to spam, and demanded to know why. Instead of admitting that they’d failed to follow best practices, the agencies/consultants went a different route: They told their clients that it wasn’t their fault — it was Google’s! Gmail, they said, was biased against their candidates.
    • So all of this led to an interesting moment: Earlier this year, Google announced that they’d set up a pilot program to make sure that political emails always stayed out of the spam folder. I, among others in the email community, worried about this decision. Was Google going to automatically allow anyone — even those who didn’t follow best practices — into the inbox?
    • And this month, Google rolled out their plan, and announced that in order to take part in the pilot, any political campaign has to first follow a specific set of best practices. They need to authenticate their emails, turn DMARC to enforcement, and keep spam complaints below a certain threshold. 
    • I’ll hand it to Google: This is an ingenious move. Publicly, they’re showing that they’re listening to the complaints of politicians; behind the scenes, they’re forcing these campaigns to do the stuff they should have been doing in the first place!
    • Anyway, if you want to read more, Kickbox’s Jennifer Nespola Lantz has a great column about the whole saga.
  • INMA’s Jodie Hopperton wrote about personalization — more specifically, how Gannett is starting to use it during the onboarding process to drive more engagement among paying subscribers (and, hopefully, reduce churn).
  • Interesting story here from Randi Stevenson and Cameron Songer of the San Antonio Express-News about what they learned when they took a subscriber-only daily newsletter and opened it up to their entire audience.
  • I’ve been getting a lot of questions lately about LinkedIn newsletters. If you’re curious about them, I’ll point you towards this story, from Summer Moore of American City Business Journals, about tips for getting the most out of those. And I’ll also recommend these tips from Ann Handley about dos and donts for LinkedIn newsletters.
  • A few stories from the indie newsletter space:
  • I continue to be fascinated by ways that newsrooms are using SMS or other messaging apps, like WhatsApp, to communicate with their audience. Here’s a fantastic example, from New York City newsroom Documented, about how they’re using WhatsApp to communicate with asylum seekers who are either in or coming to New York.

More Email Workshops in 2023? I’d Certainly Like to Make That Happen

Last month, I flew to Copenhagen for a three-day email workshop. We got 20 people from 16 different orgs — a mix of newsrooms, publishers, and editorial operations from four different countries — in the room together, and we talked through strategies to help everyone take their newsletters to the next level in the year ahead: Tactics to improve newsletters, ways to grow their lists, automations to build, and much more. And by getting lots of different orgs in the room together, they had a chance to share with and learn from each other.

That's me with the workshop crew in Copenhagen.

And the feedback from the group was incredibly positive. I’ve already heard from a few teams who’ve launched new newsletters or made changes as a result of the things they learned at the workshop. 

That’s not all. I came away buzzing, too — about the possibilities to put on more small events like these.

So what’s next? Well, let’s start here: I’d like to do two more of these in 2023.

Here’s where you come in:

  1. If you’d be interested in attending a future workshop, will you fill out this form? It’ll help me understand not just who’s interested in these, but where in the world I should be hosting them. (Yes, I’m based in New York, but the likeliest outcome is that these are hosted elsewhere!) For what it’s worth, we charged $1,650 per attendee (not including flights/hotels) for this workshop, and I’d probably use similar pricing for future events.
  2. If you’re the kind of org that might be interested in partnering with me on a future workshop, shoot me a note at dan@inboxcollective.com. The Copenhagen workshop was a partnership with Jan Birkemose at Medietrends, and it was so much better thanks to his support. If you’d be interested in helping me help newsrooms and publishers, let’s talk.

Beyond that, my goal would be to make events like these a bigger part of the Inbox Collective business, eventually launching workshops to help non-profits or those in the indie newsletter space. But that’s a bit further off.

For now, thanks for letting me know if you’d be interested in attending (or partnering on) a workshop. That’ll help me understand when, where, and who I can help!

Stuff I Loved This Month

  • I met Priti Patnaik a few years ago through CUNY’s creator program. She’s since launched Geneva Health Files, a newsletter to cover global health issues. She’s hosting a digital workshop in November to share learnings about building her newsletter— you can learn more about that event here.
  • With Halloween coming up, I’ll point you towards this list of Halloween  subject lines other brands have used to highlight sales or offers during this ~spooky~ season. Do be careful about which ones you use on Oct. 31! (And as I’ve written about before, if doing something fun or silly isn’t on brand for you, avoid those subject lines — you don’t have to use them just because others are doing it.)
  • A first for me: At a wedding this month, I was making small talk with the bride when she had a realization. “Dan,” she said, “You have to meet my new mother-in-law. She’s a huge fan of your Google Doc!”
    • And here’s the confession: It was a big wedding, and I didn’t want to randomly break up a conversation to interject, “Hi, I’m Dan, I think you read my Google Doc?” So I never got the chance to say hi to the mother of the groom!
    • So Mrs. Sherr, if you’re reading this: I’m sorry I didn’t introduce myself! But it was a lovely wedding — thank you for having us!

As promised: Here’s the next step in helping you hire (or get hired!)

On a monthly basis, I get a handful of emails from readers and clients asking if I can recommend the perfect person for a specific role. Sometimes, I have a name or two; often, I don’t.

But there’s this other thing I know: Over the years, a not-insignificant number of readers have told me that they found their next job via the listings in Not a Newsletter — which is amazing!

I’ve been trying to figure out how to do a better job getting amazing people into these roles, and that’s why I was so excited to discover a tool called Pallet. They’re a job board, and also a tool to match those who are hiring with those who are job hunting.

Here’s how it’ll work:

  • I’m focusing on what I know best: Trying to serve newsrooms, non-profits, and those with indie newsletters.
  • If you’re looking for a new job — or if you’re thinking that you might be looking in the next year or so — I’d love for you to submit your resume. That’ll help me identify candidates whose names I can share with the companies who are already reaching out to me and looking to hire. If I know you might be at least open to a conversation, I can be a matchmaker and make an intro!
    • (When you do submit to Pallet, your information remains private — you can even set things up so your info is hidden from those who work at your current company.)
  • And if you’re looking to hire, please do post your jobs to the board. That way, I know who I should be looking to connect candidates with! (You can also join the board to get access to these talented folks who are looking for a new job!)

My goal is to test out Pallet over the next few months, with absolutely no charge to anyone while this service is in the testing phase. If it works, then I’ll look to build this out in a bigger way in 2023.

But for now, the two things to know:

📬 If you’re searching for or open to a conversation about a new job, you can submit your info here!

📬 If you’re looking to post an email job, you can post it here! (And use that same link if you’d like to join the board and get access to the talent listed in the collective.)

Thanks for coming along on this little experiment with me. I’m hopeful I can get a few of you into amazing new roles in 2023!

(One last thing: This Inbox Collective board is focused on newsrooms, non-profits, and indie newsletters, but you may be looking for email roles at other types of companies. For those, you should check out Really Good Emails’s excellent job board.)

This Month in… Mel Brooks Quotes That Are Also Good Rules to Follow for Email Marketing

Mel Brooks is a comic genius, and also a surprisingly good source of inspiration for those of us in the email space. So in 2022,  I’m closing the Google Doc with a brand new feature: Mel Brooks Quotes That Are Also Good Rules to Follow for Email Marketing! This month, let’s turn to the wisdom of “The Producers”:

Here's the reaction from the crowd to "Springtime for Hitler": Silence, and a few gasps.
Embassy Pictures

Could a Broadway musical make more money as a flop than a hit? That’s the premise behind “The Producers,” one of the funniest movies (and then musicals) ever made.

I’d always wondered: Where does an idea like that come from? The answer surprised me. Here’s what Vanity Fair reported:

“It started out in life as just a title,” Brooks likes to say: Springtime for Hitler. The phrase leapt to Brooks’s lips during a press conference for a 1962 musical called All American, starring comedian Ray Bolger, for which Brooks had written the book. A reporter yelled, “What are you going to do next?” and Brooks answered, “Springtime for Hitler.” He was just being outrageous, riffing, perhaps, on the title of a forgotten 1931 comedy called Springtime for Henry, but the phrase stuck.

Good ideas come from everywhere. They come from conversations with colleagues, or emails you might trade with readers. They come from questions you find yourself asking when reading a story. They come in the shower, or on the train, or in the little riffs, rambles, and improvs you might do with a friend.

The most important thing, I’ve found: Find a place to jot down random thoughts or ideas. Often, the idea might not turn into something for a while, and that’s OK. But put it down on paper (or in a notes file, or on a voice memo, or wherever you decide to store your ideas).  You never know when your next best idea might strike.

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.