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Not a Newsletter

Not a Newsletter: March 2022

Welcome to the March 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!

Inside this issue: Yanna-Torry Aspraki is back with another edition of Ask a Deliverability Expert, answering a big question: Can an inbox tell if I’m a bad sender based on who I send my emails to? Plus: A few thoughts on setting expectations for your newsletters, ideas for what information to collect on a sign-up form, a few small Apple MPP updates, and more!

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

-Dan 

(Email / Twitter / LinkedIn)

Christopher Weyant / The New Yorker

This Month in Email Headlines

Ask a Deliverability Expert

I get a lot of questions about deliverability, and I don’t always have the right answers. But I know someone who does: Yanna-Torry Aspraki, a true deliverability expert. She’s been working in the email space since 2014 in all sorts of roles — at ESPs, with brands, and as a consultant. She really knows her stuff!

So let’s get to this month’s question:

What are spam filters looking for? How do they know if I’m a good or bad sender? Can an inbox tell just from looking at who I send my emails to?

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

What does your contact list say about you?

We often worry about growing our email lists or worry that cleaning our lists might keep us from connecting with a potential reader or customer, but we rarely discuss what our lists say about us. It is important to discuss how good or bad list management or practices can affect us as senders and how they can let spam filters know that we follow best practices… or that we don’t!

Our lists are precious to us as they allow us to sell, inform, and get people excited about our brand, but to ensure that readers remain happy to see our brand’s name in their inbox, it is very important that we follow certain best practices. Otherwise, spam filters will eventually penalize us. The inboxes are monitoring things beyond spam complaints — they are also looking at opens, clicks, and activity versus inactivity in order to decide inbox placement. Specific flags, like list hygiene, might affect their decision more than others. Lists affect deliverability because the inboxes and the spam filters are always learning more about what the recipients want to receive in their inbox, and they’re on the lookout for when senders are making certain mistakes that prove they aren’t following best practices.

I’ll say it again: Never buy an email list

The most important part of managing lists is having our subscribers’s consent. Every year, spam filters are getting better at detecting and differentiating good senders from bad ones, and your lists can be a telltale sign that you aren’t following best practices. Even if you are legally allowed to purchase a list in the country you live and do business in, inboxes and spam filters don’t like that kind of behavior and will penalize you for it. We tend to forget that the main client of an inbox is your subscribers. The inboxes want to ensure they keep their customers happy. And one easy way to do that is to reduce unwanted emails.

A list filled with subscribers that have given consent to receive emails from a brand will interact completely differently from one that has been bought, thus signaling to spam filters and inboxes that you are not following best practices. It can be very obvious in certain cases. People will barely engage after some time, they will ignore your emails or brand, or worst of all, users will report your emails as spam. These are clear red flags, and you will get penalized for them. 

And just from looking at the data in your email service provider, you might not realize if you’re dealing with lots of spam complaints. Google, for example, will tell you the percentage of their clients that reported your email as spam on a particular day, but won’t tell you who marked you as spam. Spam complaints, how they work, and how they are calculated is a whole topic in itself, and I might even write a future Ask a Deliverability Expert about it, but the thing you need to know is that there’s a disconnect between the data your inbox has about a subscriber and what you or your ESP have access to. Most inboxes do not share complete spam complaint information, so you might be emailing complainers over and over again without anybody being able to tell you to stop. If a particular inbox doesn’t provide this information, your email marketing tool won’t be able to either. 

This is one of the first reasons we should work on growing our lists organically instead of renting or purchasing them, because what do you think inboxes think of your sending practices if you don’t stop emailing those who keep saying that they don’t want your emails? Inboxes aren’t here to make our life as marketers easier — they are here to offer amazing inbox services to their customers, even if that means protecting them from our emails.

Beware of the spam trap

There are lots of tools out there, like Bouncer, that allow any email sender to clean out a purchased list. These tools can help you remove most invalid or fake email addresses that would usually hard bounce, but will never remove 100 percent of the email addresses that will negatively impact your business. Every list cleaner has its strengths and weaknesses. Some are better at detecting catch-all emails, others are better at detecting invalid email addresses coming from inbox providers in certain countries. But no list cleaner is good enough to make up for bad sender practices. You might not get in trouble right away if you use these tools, but the inbox will figure things out over time. Spam filters exist to protect inbox users and minimize any email that may be considered spam. And with the billions of emails being sent worldwide, spam filters are learning new tricks very quickly.

And here’s something else to think about: Spam traps. Inboxes want you to have permission and a relationship in order to email someone. How can they tell that you have a relationship with the human behind the inbox? By creating email addresses that have no humans using them, hiding those emails all over the internet, and hoping you’ll add these emails to your list. These are known as spam traps. Spam traps will always look like a real email address. They can even be an email address that used to exist but is no longer managed by its original owner. But spam traps do not belong to a specific person, so there would be no way for them to have subscribed to your emails unless you went and added that email yourself. When a spam trap is found in your list, that sends the signal that you’re sending to lots of other inboxes without their consent. 

Segmentation and reactivation opportunities

List hygiene goes beyond blindly deleting undesirable or inactive subscribers. It means taking a look at your entire list to separate active and engaged contacts from ones who aren’t engaging with your emails, which in turn will help you optimize your targeting. Your email strategy will produce better results if you focus on subscribers who are opening, clicking on emails, and performing the actions you want them to perform, such as buying your product, reading your content, or signing up for your next event.

Focus on ensuring that customers are receiving content that they find valuable and that you are helping customers engage positively with your content. Let’s say you’re an eCommerce company that sends lots of emails. Start with a goal in mind, and try segmenting based on factors like gender, age, interest, or purchase activity. If they’ve purchased already, for instance, you might try to convince them to make a second purchase. Or maybe they’re disengaging from your emails. In that case, focus on trying to win back their trust by showcasing products that you think will be relevant to them.

Here’s another tactic to try: Start by pulling a segment of your list that hasn’t opened or engaged with your emails in, say the previous three to six months. Then try to win them back. This type of campaign is often known as a reactivation or re-engagement campaign. The goal here is to get a reader’s attention and offer a specific reason to start reading your emails again. If they engage, then you’re free to continue to send emails to them. 

Two other tactics you might want to consider: You can always move your inactive readers into a special segment where you only communicate with them a handful of times per year, typically when you’ve got big news or announcements to share. Or, if you’d prefer, you can unsubscribe them from all emails. Send one last campaign letting them know that you’re going to remove them from your list if they don’t click on a specific link you added in that email, and then unsubscribe everyone who doesn’t click.

Your list might shrink sometimes, and that’s OK

Why are we working so hard to grow our lists and then letting people drop off? It’s a lot of work to create an email and send it out, and it can be very discouraging when our subscribers don’t engage. But reducing the number of contacts from your list that you clean out every 3-6 months can even be a goal or KPI you measure. Clean your list today and mark the percentage of subscribers you had to remove or re-segment. Then try again later in the year, after you’ve made some improvements to your marketing and targeting. See if your re-engagement list is a bit smaller than before – that’d be a great sign!

Since your list says so much about you and your practices, a poorly-maintained list can be a dead giveaway that you’re not following best practices. You might be purchasing lists, you might be renting lists, you might be collecting email addresses on your site in shady ways. I understand that having more people on your list feels reassuring. Everyone wants to reach a big audience! But just because you’re reaching more people doesn’t mean they’re automatically going to pay attention to what you have to say. If you’re forcing somebody to listen to your message, you will get penalized. So focus instead on the people who love your brand, who engage with your messages, and who will ultimately read, click, purchase, or take the steps you’re looking for.

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

Yanna-Torry is a Canadian-born, Netherlands-based email and deliverability specialist at EmailConsul, a new deliverability monitoring tool. In 2020, Litmus gave her their first-ever Coach Award for her work serving the email community. You can follow her on LinkedIn or Twitter. And this month, Yanna-Torry launched a free deliverability course on Udemy. If you want to learn more from her, sign up here!

Have a question for Yanna-Torry? Submit it here, and she might answer your question in an upcoming edition of Not a Newsletter!

For Your Reading / To-Do List

  • Keri Mitchell, executive director of Dallas Free Press, talked with the Institute for Nonprofit News about building a newsroom around SMS as their primary channel. The big takeaway here: The Free Press used pre-launch reader conversations to guide their audience development strategy — readers asked for SMS instead of email, so that’s what they did.
    • And as I’ve been writing about for a while now here in the Doc: I see email and SMS as complementary tools. Both are mobile-first tools that allow you to start a 1-to-1 conversation with your readers. Orgs that launched with newsletters will eventually add SMS into the mix, and those that launched with SMS will eventually build out an email strategy to complement their growth.
  • Speaking of email + SMS: I was thrilled to see two fantastic newsrooms in Detroit — Outlier Media, which was built with SMS as its flagship channel, and Detour Detroit, which was built around newsletters — announce that they’re merging. This team’s going to do big things in the years ahead.
  • A few stories from the creator space:
    • This might be a newsletter first: Discourse Blog launched on Substack, left in fall 2020 to go onto their own platform, and now is coming back to Substack. Their Jack Mirkinson explained why.
    • The team at Arizona Agenda, a newsletter about state politics in Arizona, gave an update about their growth about seven months after launch. They have more than 900 subscribers, which comes out to about $68,000 in annual revenue. But as they note, that’s only about half of what they need to operate. (Not to grow or add staff — just to operate.)
      • I have two thoughts here. The first is that the Agenda has actually done remarkably well — 900 subscribers and $68k in annual revenue is incredible for a two-person local newsletter that started from nothing just a few months ago. I’m impressed by these numbers — getting to 1,000 paying subscribers by the end of year 1 would be a real achievement, and they’ve still got five months to go in their first year! 
      • But expectations can be difficult to set — or manage — with a newsletter like this. I’ll give you an example. Recently, I had a call with an independent writer who is about to roll out a paid offering on their newsletter. They surveyed their audience, and asked readers how likely they were to pay for this new offering. Half said they’d never pay. A quarter said they’d be unlikely to pay. Another 17 percent they’d be likely to pay. Eight percent said they’d absolutely pay. The writer looked at the data and thought: 50% of readers said they’d never pay — I’m in huge trouble! I looked at the data and said: Eight percent said they’d absolutely pay, and a quarter of the overall audience is at least a little interested in paying — this is amazing! The more you understand the benchmarks for comparable products, the better you can set expectations.
      • Most newsletters take at least two years, at minimum, to grow into a sustainable business. You need time to grow an audience, plus time to build out multiple revenue streams. I think the Agenda is absolutely on the right track — they just need a little more time to get to a place of sustainability.
      • One other thing I want to note: With all of the local or creator-driven newsletters I work with, I’m always encouraging them to share updates with their readers like the one the Agenda published. Interestingly, I’ve found that these sorts of updates often lead to a spike in subscriptions — maybe it’s because readers like seeing proof that others are subscribing, too; or maybe it’s because readers want to support the writers and their dream of building an independent publication; or maybe it’s because they’re getting a different sort of nudge to subscribe. Whatever it is, if you’re building a newsletter like this, don’t forget to share your progress with readers — good or bad!
  • Let’s talk about email tactics for a moment. I was so excited when Digital Ink’s Sarah-Leah Thompson reached out a few weeks ago with a question: What kind of data should someone collect on an email sign-up form? Should they also ask for first name, last name, location, or data about their job? You’ll note that she asked seven different email experts, and got seven slightly different answers. There is no single *right* answer here — it’s really about figuring out what makes sense for you and your email operation.
    • If you want to see a good example of the type of sign-up flow I really love, check out this form from Neil Patrick Harris’s newsletter, Wondercade.
  • Nice work here from Kayleigh Barber of Digiday to dig into The Daily Beast’s strategy around collecting first-party data from users through email and registration walls, and how they’re using it to identify ways to better convert readers to paying subscribers.
  • I loved this story from WAN-IFRA’s Neha Gupta about BloombergQuint, an India-based subscription site that now boasts 65,000 paying subscribers. Media observers spend so much time looking at the big players in the U.S. and Europe, but newsrooms elsewhere often get overlooked. So here are a few things about BloombergQuint that I wanted to highlight:
    • They were able to get more readers to complete the sign-up flow by removing unnecessary fields, like asking for a phone number.
    • They’ve had success targeting different offers to different types of customers. New subscribers might get an offer to sign up for a year, while current subscribers are getting two-year subscription offers.
    • They’re using reader surveys to constantly improve the editorial product.
    • They’ve created specific engagement thresholds to understand who might be likely to convert, and who might be likely to churn.
      • Do read the full story — this is a great example of a newsroom that’s using a combination of editorial products, data, and reader research to build a great subscription strategy.
  • On the Sparkpost blog, Elsbeth Russell talked about five email trends for 2022. One in here that I’m absolutely focused on this year: Using email for retention. Getting a paying customer is great — keeping a paying customer is even better.
  • And if you’re wondering what kinds of content you might want to send to those paying customers to keep them engaged, this list of 50 content ideas for email from Campaign Monitor’s blog might be a good starting place.
  • The team at Really Good Emails put together their list of the 15 most popular brands from 2021. Do make time for this list — there’s a lot you can learn from brands that send amazing email!
  • Three small Apple Mail Privacy Protection notes: 
  • This isn’t specific to email, but it might affect the way you measure email success: Google Analytics is retiring an old version of GA and moving over to a new version, Google Analytics 4, in July 2023. Here’s what you need to know.
  • And last but not least: A study of dentists across the U.S. found that 1 in 3 say email is not important to their business. Turns out that trying to get dentists to follow digital marketing best practices truly is like pulling teeth. (Thank you, thank you, I’ll be here all week, don’t forget to tip your bartenders!)

Stuff I Loved This Month

  • A shout-out to Jordie van Rijn, who put together a great resource about email businesses that are taking steps to support Ukraine, and ways that the email community can get involved and show their support.
  • Say you’re building a landing page for your newsletter, and you want to show off an example of what the product looks like. You’re going to need a screenshot of the newsletter on a phone. What’s the best way to do that? I wrote up a quick tutorial that anyone can utilize — no design skills necessary!
  • If you read the Google Doc regularly, you know how excited I get about email Courses, which are automated email series designed to teach someone a new skill, lesson, or habit. Here’s an amazing new one from the team at LION: The six-week News Founder Challenge. Sign up and you’ll get six weeks of ideas about how to improve your business idea. (And if you finish the thing, you’ll get a free 1-to-1 consulting call with their team to discuss your idea!)
  • INMA rolled out their Subscription Benchmarks Subscription service, which allows any newsroom to compare their digital engagement and subscription data to that of similarly-sized publishers. This is the kind of thing that might be right for large local, regional, or national publishers — check it out here.
  • A quick shout-out to the team at UNSPAM, which is still looking for speakers for their upcoming conferences. They pay an honorarium ($1,000) for speakers, and cover travel and lodging. Hoping for more of all of this — transparency in pay, and support for speakers — in 2022 and beyond.
  • Simon Owens, who hosts The Business of Content podcasts and writes a media newsletter about content creation, is launching a 10-week, Zoom-based class (in partnership with the University of Oregon), called Growing Your Content Business. They’ve put together an all-star lineup of panels, and their team tells me you won’t have to do too much homework for the class (mostly just readings). The goal here is to give students the chance to hear from people who are doing great things in the content space. The deadline to register is April 1.
    • And one more thing from Simon: Do check out his story on Starter Story, a website that shares case studies from successful businesses. They share a fascinating example of how to use Reddit to grow a newsletter.
  • Ben Collins, the go-to expert on all things Google Sheets, built a really cool tool to allow anyone sending via ConvertKit to pull a daily report into Google Sheets. ConvertKit users, do give this a try!
  • This story about a collaboration between Lawson’s Finest Liquids (a fantastic Vermont brewery) and Vermont Public Radio is just cool.

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 “History of the World”:

Mel Brooks, as Moses, drops one of the tablets
Brooksfilms

Moses [speaking to the Israelites from Mount Sinai]: Hear me, oh hear me! All pay heed! The Lord, the Lord Jehovah has given unto you these fifteen… 

[drops one of the tablets] 

Oy! Ten! Ten commandments for all to obey!

When you’re putting something out into the world, things often go wrong. This is just how things go with the launch of a project. You’ve put so much attention into the launch, which means you’ve made dozens (or maybe even hundreds!) of tiny decisions. And the more decisions you have to make, the more things will probably go wrong.

You can go through your pre-launch checklist, but you still might drop the ball (or, I suppose in Moses’s case, a tablet). Remember: It’s just a mistake, and if you’re lucky, it’ll be a small thing that nobody notices. Whatever happens, just go with it.

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.