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Not a Newsletter

Not a Newsletter: June 2023

This month in Not a Newsletter: Strategies for adding personality and personalization into your emails, and why it’s OK if growth isn’t your No. 1 priority.

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Welcome to the June 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!

A big thank you to Litmus, this quarter’s presenting sponsor of Not a Newsletter and Inbox Collective! They’re an all-in-one marketing platform that empowers you to build, test, review, and analyze emails so you can get the most out of every email you send. Learn why 700,000+ professionals trust Litmus to make every send count.

A woman opens a donation letter. It reads, "Your generous contribution helps fund these solicitations."
William Haefeli / The New Yorker

And a thank you to this month’s sponsors: InboxArmy, a full-service email marketing agency, and Echobox Email, an AI-powered email platform. Do support these sponsors — they make sure that resources like Not a Newsletter remain free for all!

This month in Not a Newsletter, you’ll learn about:

  • Strategies for adding personality and personalization into your emails.
  • How to decide whether you should use single opt-in or double opt-in to keep your lists clean.
  • Why it’s OK if growth isn’t your No. 1 priority.
  • Lessons about converting readers from Twitter to your newsletter.
  • Email trends to monitor in the second half of the year.

…and more!

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

—Dan (say hi via email or LinkedIn)

This Month in Email Headlines

Stories labeled with a 🔑 may require a subscription to read.

*SPONSORED* How to build the right workflow for your newsletter

How are other orgs building out their emails? The team at Litmus dug into that question — surveying over 440 marketers to determine who’s building emails, how they’re building them, and what the results were afterwards. From struggles to solutions, they’ve put together a massive guide to help you understand how other marketers are working and what you can learn from them.

In this report, you’ll learn:

  • What issues frustrate email marketers the most.
  • How long it takes for other orgs to build out an email campaign.
  • How to measure email ROI — and what calculations to use to get there.

Get answers to all these questions and more in The 2023 State of Email Workflows Report. 

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To be as transparent as possible: This is a sponsored link presented by my partners. Interested in partnering with me? Here are the ad opportunities available with Not a Newsletter + Inbox Collective, and here’s what’s available to book right now.

New on Inbox Collective

📬 How to Add Personality and Personalization Into Your Emails

“Personality” is all about you and your voice — who you are, what you care about, and how you talk with your audience. “Personalization” is all about your recipients — how you deliver relevant stories, topics, or conversations to your readers.

These two forces are shaping today’s newsletter landscape. Many newsletters exclusively lean in one direction or another — but there can be a third way: Finding a sweet spot between the two to create a more powerful email strategy.

Without a blend of the two, your emails might feel like a one-sided conversation. With too much personality, you risk ignoring the preferences and needs of your readers. With too much personalization, you’re not taking the time to tell the stories or build the 1-to-1 relationships that might cement your place in the inbox. It’s worth striving for a place somewhere in the middle. 

The good news is, no matter where your newsletter currently is on the personality vs. personalization spectrum, there are ways to add in more of whatever element you’re currently lacking.

Here are a few ideas for using both in your email strategy.

📬 Should I Use Single Opt-In or Double Opt-In For My Newsletter?

The answer isn’t quite as straightforward as you’d expect. Some email experts say you should absolutely require a confirmation step, and that not doing so will have a huge, negative effect on your deliverability. Others say just the opposite: It’s not all that important and you should allow sign-ups without it.

So who’s right? And what’s the right strategy for you?

It depends on a few factors, like how fast you’re growing, how often you clean your email lists, which email platform you use — even where you live.

Let’s talk through the options and try to figure out what makes sense for your newsletter.

📬 It’s OK If You Grow Your Audience Slowly

Not everyone wants to build out an aggressive growth strategy for their newsletter. Say you’re a person who feels disingenuous trying to market yourself, or you write for a smaller, niche audience and prefer your newsletter to feel more like an intimate dinner party and less of a giant food fair. Or maybe you don’t have the time to integrate time-intensive marketing strategies.

Does this mean your newsletter is doomed to obscurity and failure?

Not at all. For some indie newsletters, a focus on content or community — not growth — is the right move.

Claire Zulkey talked with three other independent operators — Kate McKean of Agents & Books, Chris La Tray of An Irritable Métis, and Kevin Freidberg of 7-Second Websites — about why slow growth makes sense for their newsletter.

📬 Ask a Deliverability Expert: What Do I Need to Do If I Change Domains?

Successful businesses sometimes outgrow their original names. And when those businesses change names, there are huge effects on all parts of that company’s digital operation. Email could be affected in the change — a rebrand may affect deliverability.

I reached out to Not a Newsletter’s resident deliverability expert, Yanna-Torry Aspraki, for her suggestions. Here’s what she recommends you do to make sure you stay out of the spam folder when switching domains.

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*SPONSORED* Hire InboxArmy to help you build your best email marketing program

If you’re reading this, you probably already know that I consult with a number of news organizations, non-profits, and indie newsletters through Inbox Collective. But often, I’ll get emails from companies — particularly startups, SMBs, or ecommerce brands — who need a lot of help building out or executing on their email strategy. Maybe they need someone to set up automations, like a welcome flow or an abandoned cart series. Maybe they need help with deliverability. Maybe they need email templates designed, or someone to handle the week-to-week sending of marketing campaigns. Maybe they need an expert to help them evaluate different ESPs or migrate to a new platform.

When they ask, I often send them over to my friends at InboxArmy, a full-service email marketing agency that works with big brands to help build, optimize, and grow an email strategy. But they don’t just do strategy — one of their biggest strengths is that they have the team to help big organizations execute on that strategy. (Inbox Collective’s a one-person operation, but InboxArmy’s a team of 120+, so they’re a much better fit for a lot of big companies!) To set up time with InboxArmy to learn how they can help you improve your email strategy, shoot Saumil Shah an email at saumil@inboxarmy.com, and let him know that I sent you! They’ll set up time and talk you through the next steps.

What Else I’m Reading

Stories labeled with a 🔑 may require a subscription to read.

Growth

  • I’ve never spent much time on Twitter, but I’m interested in how others are using threads to convert readers from that platform to newsletters. There are lots of writers thinking about the Twitter-to-newsletter funnel, but few have done it better than Sahil Bloom. Growth in Reverse’s Chenell Basilio wrote about how he built his Twitter thread strategy and grew his newsletter to over 400,000 subscribers.
  • Before you spend any money on acquiring email addresses, make sure you understand the quality of the subscribers you’re acquiring, the lifetime value of those subscribers, and the time it’ll take you to make your money back from this investment. Growth Currency’s Dylan Redekop wrote about these three metrics and what to watch for before spending a single dollar.

Content Strategy

  • I love seeing more newsrooms experiment with different formats for newsletters. These customizable weather alerts, from The New York Times, are a fantastic example of a newsroom using email in a practical and personal way.
  • Creator Boom’s John Bardos wrote about a few different flywheels — for growth, content, and monetization — and how to apply them to your newsletter.

Monetization

  • The Reuters Institute’s Digital News Report is out, and as always, it’s a lot to dig through. The full, 160-page report is here — but one little nugget I wanted to call out: 8% of all Americans pay for a newsletter written by an indie writer, influencer, or journalist. It’s amazing how fast that percentage has grown — and here’s betting that there’s still room for growth. (In particular, among writers based in countries outside the U.S.)
  • Beehiiv’s Darwin Binesh talked to Richard Patey, who’s built and sold several newsletters over the past 10 years, about what he’s learned and how he’s applying lessons from a decade in newsletters to his work today.
  • So many newsrooms use paywalls to convince readers to pay — and to drive newsletter sign-ups, too. Madeleine White put together a list of 50 paywall examples to inspire your org’s strategy.
  • Indiegraf’s Lauren Kaljur wrote about why more newsletters and newsrooms should talk about their finances with their audience. I completely agree — both the news organizations and indie writers I work with have seen a bump in reader revenue after peeling back the curtain and talking about how things are going.
  • On the Indie Hackers blog, Anthony Castrio explained why he decided to lower his ad rates — and immediately sold out two months of sponsorships.
  • Looking for ideas for a summer sale or deal? This article from Brevo has a few ideas for summer-themed emails to send.

Best Practices

Tests, Experiments, or Learnings

  • I love seeing news organizations experiment with different strategies for converting readers to supporters. Here’s a great example from New Hampshire Public Radio. As Hannah Wingo wrote for Greater Public, NHPR implemented a testing strategy to see what might convince readers to give:

“Not every single idea knocked it out of the park, but it was valuable for the team to learn what worked and what didn’t. For example, a monthly $3.14 sustaining ask for Pi Day coincided with an unexpected snowstorm on March 14th. The response was lower than expected, but the gifts that were made were accompanied by excellent listener feedback expressing gratitude for making a monthly giving level that was more inclusive and accessible.”

  • I absolutely love that. Test everything, see what works, learn from successes and failures — and then keep testing!
  • One more from the non-profit world: NP Source wrote about five things to implement on your next fundraising campaign. (I’ll second idea No. 1 on this list: “Start with gratitude.”)

*SPONSORED* Use AI to send the perfect email at the perfect time

A few years ago, the team at Echobox showed me an amazing tool they’d built for social media. Major publishers like The Guardian were using it to automate their social media workflows — the tool could pull in content, write headlines, and publish posts to Facebook or Twitter automatically. (And the tool was more effective at driving clicks than human editors.) I told them that I’d love to see them bring a similar product to the world of email.

Now they have. Echobox Email is an AI-powered email platform that can personalize your suite of newsletters in a fully automated way. It can do content personalization — it learns about your subscribers, and then uses deep learning to share stories tailored to each reader. It can also do send-time personalization to make sure you’re emailing each subscriber at the time they’re most likely to open newsletters.

Testing’s shown that Echobox’s AI content personalization boosts click rates by 49% on average. And it can do all of this automatically. You feed Echobox an RSS feed of your stories, and it’ll have a fully-optimized newsletter ready in just 10 seconds. You can still choose to review and approve before sending, or build custom emails manually if you wish.

Give Echobox Email a try and join more than 2,000 publishers using it to personalize and automate their newsletters. Read the factsheet and request a demo to learn more about how Echobox can help you boost newsletter performance while saving time.

Stuff I Loved This Month

  • The team at HBM Advisory put together a free digital assessment for newsrooms. Answer a few questions, and you’ll see how your org stacks up against hundreds of other publishers around the world. I’d highly recommend that news organizations go through the assessment — you’ll learn a lot.
  • Should you be using AI to code emails? Two veteran developers, Email on Acid’s Megan Boshuyzen and Action Rocket’s Jay Oram, shared their perspective.
  • I linked to one of her stories above, but I wanted to give another shout-out to Chenell Basilio. In her newsletter, Growth in Reverse, she’s been using a referral program in a really smart way: Instead of offering a lead magnet or merch, she’ll promote your newsletter to her audience — as long as you first refer 10 readers to her newsletter. It’s a reminder that there are lots of established ways to grow your list, but there are still so many new ways to experiment with growth.
  • I continue to be intrigued by the possibilities of print. I’ve been thinking a lot about how to bring some sort of semi-occasional print product to market for Inbox Collective — I do think there’s value (and revenue!) in these sorts of niche products.
  • Adam Silver wrote about something that’s been bugging me for years: The fact that some email service providers don’t offer a two-step opt-out process. Without it, it’s so easy to accidentally unsubscribe — or, as Adam discovered, for an email security tool to unsubscribe readers while checking every link in a newsletter. This is something I’ve brought up over and over in conversations with various email platforms — and I hope more ESPs will consider adding a confirmation page to the process so these accidental unsubscribes don’t happen.
  • And finally: Last month was the best month ever for the Inbox Collective site: 13k unique visitors and 19k page visits — with the average user spending 3:25 on site. A big thank you to many of the newsletters who’ve been sharing our stories lately, including LION Publishers and Really Good Emails. I’m grateful to everyone who’s helped amplify and share these stories!

The (Not a) 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 corner of the doc. For years, I closed every edition of Not a Newsletter by highlighting one of these animals. But then I had an idea: What if I commissioned an artist to design new animals just for Not a Newsletter?

So to close out this edition of Not a Newsletter, I want to spotlight one of these animals in a feature I call… the (Not a) Google Docs Anonymous Animal of the Month!

Thanks to Anna Kosak for designing this month’s animal: the Bald Eagle!

an image of the bald eagle
  • A group of bald eagles is known as a convocation.
  • Forty years ago, there were only 417 breeding pairs of bald eagles left in America. But after the Endangered Species Act was passed in 1973, the bald eagle population started to recover. As of 2019, there are more than 71,400 breeding pairs of bald eagles in the lower 48 states — and about 317,000 bald eagles total.
  • You’ll find bald eagles all over North America, sometimes as far as south as Texas or Florida.
  • But if you really want to spot a bald eagle, forget about the lower 48 states. Head north, to Haines, Alaska, where every November, 3,000 bald eagles return to feast on local salmon who are swimming upstream to spawn.
  • Bald eagles return to the same nests every year to lay eggs. These nests grow in size every year. One, discovered in Minnesota this year, weighed more than 2,000 pounds and was perched 100 feet in the air.
  • If you’ve heard a bald eagle’s call on TV, I’ve got bad news: You’re not actually hearing a bald eagle. Their call is rather quiet, so what you’ve actually heard is a red-tailed hawk’s more distinctive, shrill call instead.

Anyway, the Bald Eagle! That’s your (Not a) Google Docs Anonymous Animal of the Month. 

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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.