Not a Newsletter: July 2023

Welcome to the July 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!

And a thank you to this month’s sponsors: Litmus Live, one of my favorite email conferences, which has tickets on sale now; and Conversion Ads, from Refind, to help you grow your newsletter faster.

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:

What’s happening with iOS17 — and why you shouldn’t be worried that Apple will be taking your click data away. (You’ll also hear directly from a few ESPs with their take on the changes.)
Why writers in Brazil are bullish about the possibilities for independent newsletters in their country..
How The Small Bow built a newsletter and digital community out of a personal tragedy.
Tactics for handling credit card payment issues that often lead to subscriber, member, or donor churn.
Strategies for writing funnier, warmer copy in your newsletter.

…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.

Gmail Debuts Mail Merge Feature, Allowing Users to Send Personalized Emails to Up to 1,500 People (Android Police)
🔑 The New York Times Cooking is letting readers taste test recipes over text to drive subscriptions (Digiday)
🔑 Telegram Is Secretly the Most Influential App in the World (The Atlantic)
City Cast Expands Through Acquisition of Madison Minutes Newsletter (Press Release)
Email Industries Acquires Leading International Email Marketing Conference, Inbox Expo (Press Release)

New on Inbox Collective

📬 The Small Bow Built a Community Out of Personal Tragedy

If you recognize the name “A.J. Daulerio,” it’s probably from the moment when he was arguably the most notorious blogger in America.

He was a defendant in a 2016 trial mounted by Terry “Hulk Hogan” Bollea against the website Gawker for running a sex tape without the wrestler’s permission. The trial was an awful time in Daulerio’s life. He was broke, unemployed, and had recently completed rehab for drug and alcohol addiction.

But he made it through — through the trial, bankruptcy, and addiction — and reinvented himself as a newsletter writer and producer.

His newsletter, The Small Bow, is a place where Daulerio can unpack his post-Gawker, post-trial, post-substances life. It launched in 2018, and now, about 7,000 subscribers receive Daulerio’s twice-weekly interviews and essays on addiction, recovery, sobriety, and mental health.

But The Small Bow is more than a newsletter. Five times a week, members of his community come together for recovery meetings hosted on Zoom, very loosely based on the Alcoholics Anonymous format.

Inbox Collective’s Claire Zulkey talked with Daulerio about what’s working with The Small Bow, his goals, how he walks the line between being creative online and having peace of mind, and how after surviving both the blog bubble and bankruptcy, he’s making money again from writing — this time, via a newsletter.

Read the full interview here.

📬 Inside Brazil’s Growing Indie Newsletter Economy

Brazil’s media landscape has grown more diverse and digital, and newsletters have emerged as a key way for writers, journalists, and organizations to engage with audiences. While traditional media outlets have faced financial constraints, massive layoffs, and struggled to adapt to digital platforms, independent journalists and writers have seized the opportunity to build direct relationships with their readers.

In the expanding world of Brazilian newsletters, one name has captured the attention of readers and industry insiders: Gaía Passarelli. A former MTV host and media personality, Passarelli has harnessed her existing popularity by tapping into the power of a growing medium. After the launch of her newsletter, Tá Todo Mundo Tentando (Everyone is Trying), in the midst of a nationwide lockdown, Passarelli emerged as a success story in the era of pandemic-born newsletter writers.

Nathália Pandeló Corrêa talked with Passarelli — as well as others in the Brazilian newsletter space — to understand what’s working and what’s next for newsletters in Brazil.

📬 Ask a Deliverability Expert: 25 Ways to Keep Your Newsletter Off Blocklists

If your newsletter ends up on a blocklist, you might be in real trouble. As Yanna-Torry Aspraki wrote in her guide to blocklists back in March: “If you end up on a blocklist, you may find yourself unable to deliver your emails to your readers. The blocklist effectively tells the inbox, ‘This sender seems shady — send their emails to spam.’”

These blocklists are maintained by companies like Spamhaus, Spamcop, or Barracuda Central, and getting off one isn’t easy. You can submit a removal request to the blocklists, but it takes time to go through that process, and it might take even longer for the inboxes to start to treat your emails as reputable.

The best way to deal with a blocklist? Don’t get on one in the first place.

With that in mind, here are 25 tactics you can use to make sure you stay off blocklists, out of the spam folder, and in the inbox.

What’s Going On With iOS17?

Earlier this month, I became a dad for the first time — my wife and I welcomed a baby boy into the world. (He’s doing great, as is his mom.) I’m taking the summer off from my Inbox Collective consulting work, and I’d told clients to be prepared. Me taking the summer off meant that *something* was bound to happen in the email world while I was off.

So the day we left the hospital, Apple announced the release of what they called “powerful new privacy and security features” as part of iOS17 and macOS Sonoma, which will both roll out in September. This was part of their announcement:

Link Tracking Protection in Messages, Mail, and Safari Private Browsing

Some websites add extra information to their URLs in order to track users across other websites. Now this information will be removed from the links users share in Messages and Mail, and the links will still work as expected. This information will also be removed from links in Safari Private Browsing.

I got more than a handful of panicked emails about the announcement. Some sent me articles suggesting that Apple would be making it impossible to track click data or would strip away all UTMs attached to URLs.

So, in the spare moments between feedings and naps, I did a bit of digging into these changes. (For the sake of simplicity, I’m going to refer to these as the “iOS17 changes,” even though it’ll also involve messages read on devices running macOS Sonoma.) Here’s what I can tell you, and I’ll put this in bold to make it as clear as I can:

For the overwhelming majority of Not a Newsletter readers, these changes will have virtually no effect on your email strategy or data.

This isn’t a situation like in summer 2021, when Apple announced Mail Privacy Protection (MPP) as part of iOS15. That did have a real impact on email marketers — open rates for most newsletter operators went up, and MPP pushed many in the industry to rely less on open rates as an indicator of success.

The changes for iOS17 aren’t anything like what we saw with MPP. They’re not anything I’m worried or panicked about.

But you’re a Not a Newsletter reader, which means you’re more curious than most. I know you’ve got questions — so let me share what I’ve learned on my end.

How does click tracking in email actually work?

So let’s start with a bit of Email 101: Open rates and click rates are typically tracked in different ways.

Open rates are tracked using a tiny, transparent image within the newsletter. Sometimes that image is at the very bottom of your email, and sometimes, it’s at the top. When the email is opened, your ESP delivers the image to your mailbox — and every time it does, it counts that as an open.

Click rates are tracked using tracking links within your newsletter. I’ll use my newsletter as an example. Here’s a section, below, from my June newsletter:

I send my newsletters via Mailchimp, but what I’m about to explain holds true for nearly every ESP. When I went to include the link for that first story, I grabbed the URL:

https://inboxcollective.com/how-to-add-personality-and-personalization-to-emails

Then I added UTMs — these little bits of code that help me track the source of the click. Many publishers use a tool like Google Analytics to track on-site data; I use Fathom Analytics, which offers simpler dashboards that work nicely for a small website like Inbox Collective. For my links, I always add two UTMs:

Where the click came from: utm_source=Not_a_Newsletter
What edition of Not a Newsletter it came from: ?utm_campaign=June_2023

The result looks like this (I’ve added italics for emphasis):

https://inboxcollective.com/how-to-add-personality-and-personalization-to-emails/?utm_campaign=June_2023&utm_source=Not_a_Newsletter

But here’s the thing: If you click on the link in the actual newsletter I sent out, you’re not taken immediately to that URL. You’re first taken here:

https://inboxcollective.us19.list-manage.com/track/click?u=e5101197dd74666a141a34e7b&id=c9d42c3ff3&e=f441b3bd13

That click-through URL is the tracking link. It’s something Mailchimp automatically includes when the newsletter is deployed. (It works a lot like a link-shortening tool, like bit.ly — minus the part where it makes the URL shorter.) In my case, the click-through URL initially takes the reader to a link hosted by Mailchimp, where the click is tracked and logged in my Mailchimp dashboard. Then the user is redirected to the URL with the UTMs I’d added. The whole process happens so quickly, most users don’t even know it happened — they just see the final URL pop up on their device.

Nearly every ESP works this way to track clicks. Your URLs first go through a redirect, where the clicks are tracked, and then to the final URL.

Dan, stop stalling and answer the big question: Does all this mean iOS17 will affect the way clicks are tracked for my newsletter?

No, it won’t affect the way clicks are tracked for your newsletter.

Apple can’t overwrite those tracking links. They can, as they announced in their press release, remove some “extra information” from the final URL (more on this in a moment), but the tracking links will still work. And as long as those links still work, your clicks will still be tracked correctly in your ESP.

So Apple isn’t going to open every link in my newsletter to screw up my data?

No, that’s not what’s happening here.

I do understand the worry from email marketers and newsletter operators. When Apple introduced MPP, they started pre-fetching emails for readers — basically, opening a newsletter, with a user’s permission, before the user does. For most Inbox Collective clients, that’s led to an increase of about 10-20% in their average open rates. MPP hasn’t made open rates irrelevant — they’re just a little inflated.

(A quick aside, to correct a common misconception in the email space: Contrary to what you may have read elsewhere, MPP hasn’t meant that every newsletter has a super-high open rate. I work with plenty of clients who, when we first start working together, have open rates as low as 20-25%. Before MPP, I’d have told them that their numbers were fairly average — now, with MPP, I tell them that they have significant room for improvement.)

But what Apple did with opens through MPP isn’t what they’re doing with iOS17 and click data. There won’t be “click rate inflation” the way there was “open rate inflation.” Everything iOS17 is doing is designed to affect some types of user tracking after a reader clicks out of their inbox.

Will iOS17 strip away the UTMs I add to my URLs?

More good news: No, they won’t.

There’s been independent iOS17 testing from a few sources — Nicole Merlin of Knak, Peter Jakuš of Bloomreach Engagement, and Steve Atkins at Word to the Wise. All three reported the same finding: Apple isn’t stripping away your UTMs.

Any UTMs that you add to your own links will remain, and you’ll be able to use those to track on-site behavior and engagement after a reader clicks.

So what will iOS17 actually do that affects email?

As Steve Atkins of Word to the Wise wrote after doing some testing with iOS17:

It seems pretty clear that the target right now is the large scale marketing and social media attribution PII sharing marketplace, not click tracking and attribution by ESPs or email marketers.

Apple aren’t going to take your clicks away.

Let me break that down for you in more detail.

After someone clicks on a link in your newsletter, there may be some additional data in the URL that’s designed to identify a user who’d otherwise be anonymous. These parameters are sometimes added by marketers, and sometimes by the platforms that marketers work with. Common parameters include fbclid, which Facebook uses to tie web activity back to a specific user, and gclid, which Google uses for similar purposes.

These tracking parameters are usually connected to cookies, which are used to track you across the web so that a marketer can see, for instance, that the user who clicked on a link in their newsletter and the user who later made a purchase on their website is actually the same person.

What Apple is doing is attempting to remove those bits of personally identifiable information, or PII, from the URLs, which would make cross-platform tracking harder for marketers. After you click, those bits of code may be removed by Apple from the URL — while the rest of the URL and any UTMs remain.

(If you want a deep dive into how Apple is actually stripping away these bits of PII, this guide from Peter Jakuš of Bloomreach Engagement is really useful.)

Knak’s Nicole Merlin wrote a great post about iOS17, based on her team’s testing, and shared a list of companies with tracking parameters that may be stripped away by Apple. These ESPs (and email-connected products) had parameters that made the list:

Adobe Marketo
Drip
HubSpot
Mailchimp
MailerLite
Omeda

The tracking parameters listed for these six companies help connect the dots between tools. So, for instance, the Mailchimp tracking parameter listed is mc_eid — the ID for a specific email address listed in Mailchimp. It’s something Mailchimp uses when working with an outside app, like an ecommerce platform, to tie a purchase back to a specific email address.

So who’s actually going to be affected by this?

Here’s where I’ll remind you: Having a newborn means I didn’t get to go all the way down the iOS17 rabbit hole like I wanted to! I still have a few lingering questions. But the two big things I can tell you:

If you’re selling products via a third-party store, and tying the data together using an email ID from one of the products above, some of your data may be affected. Once iOS17 (and, yes, macOS Sonoma) rolls out, it may be harder to connect the dots between that purchase and your ESP.
If you’re trying to pull all of your data from multiple sources into a third-party customer data platform, or CDP, it may be more difficult to identify the actions that certain users took.

But I still have some remaining questions. Will these Apple changes accidentally break some links in newsletters? How will the changes affect programmatic ad platforms? What’s the long-term impact on Google Analytics? I’m still trying to get answers, and will share updates over the next few months as I learn more.

What are the ESPs saying about iOS17?

Like in June 2021, when MPP was announced, I reached out to nine ESPs for comment. Some told me, off the record, that they weren’t concerned about it. (“Far less disruptive than MPP,” one CEO of an ESP told me.) Here’s what they told me — and I’ll update Not a Newsletter with additional replies as they come in.

I asked AWeber CEO Tom Kulzer what impact these changes would have on users, and he told me:

Almost zero.

We’ve reviewed the changes, looked at the data across all of our users and determined that the changes are so small that, while they sound scary, they actually impact almost no one. We’re talking <0.01% type numbers.

Let me elaborate…

If you haven’t seen this Steve Atkins post yet, I 100% recommend reading it. Rather than talk about the sky falling, he actually tested what Mail.app and Safari are going to do using the beta.

The takeaway from that article: Of all the query parameters Apple could strip, the only ones to really care about are big marketing clid variables such as fbclid (Facebook), gclid (Google), twclid (Twitter), and ttclid (TikTok).

Digging into our AWeber user data, when we look at the 1,470,534 shared links that appeared in user email messages over the past 30 days, there were only 1,299 fbclid (0.088%), and 214 gclid (0.015%) links present. There were zero twclid or ttclids.

So while that’s a tiny percentage, the actual impact is even lower.

To quote Steve’s article: “If you have a link in your mail that goes to a click-tracker, and the click-tracker then redirects to a URL with fbclid, gclid parameters in it, then those parameters won’t be stripped.”

The vast majority of AWeber users use our built-in click-tracking redirects, thus even the 1,513 links that have clid’s would not be stripped by Mail.app because Mail.app would never see them behind the AWeber click-tracking redirect. AWeber does include more advanced email web analytics features that allow a sender to keep their full link visible in emails, but it’s not widely implemented by most users.

ConvertKit’s Alyssa Dulin, the company’s head of deliverability, told me:

From what I’ve seen so far, I’m not concerned about Apple’s click tracking changes having an impact on how ConvertKit and our customers use link tracking. Steve Atkins from Word to the Wise wrote up a great blog post about what he found when testing Apple’s new click tracking changes. He sums it up best: “It seems pretty clear that the target right now is the large scale marketing and social media attribution PII sharing marketplace, not click tracking and attribution by ESPs or email marketers.”

The team at Ghost told me:

Based on our testing, this change shouldn’t impact email click tracking in Ghost, as this is all run via redirects through the publisher’s own site. Other Ghost features, like fixing broken links after a newsletter has been delivered, should also see no impact.

We will be monitoring any potential impacts carefully as iOS17 rolls out, and encourage Ghost publishers to do the same, especially those using other platforms for email and analytics in addition to Ghost.

What Else I’m Reading

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

Best Practices

Lianna Patch of Punchline Copy wrote about a few strategies for punching up your copy and making it a bit warmer and funnier. (I’m personally a big fan of No. 8 — using parentheticals.)
Lots of good ideas in this article from HubSpot’s Olivia Allen: 20 Tips to Write Catchy Email Subject Lines.
- And if you want to go deeper on subject lines, here’s the guide I published last year: How to Write a Great Subject Line For Your Newsletter.
Some good advice from Kickbox’s Al Iverson: Check with your ESP to make sure you’re all set with your DKIM records. It’ll help make sure your newsletters stay in the inbox.
When I send emails for Not a Newsletter, I often leave a little bit of blank space at the end of the preheader text. For Litmus, Carin Slater explains how to add that white space to make your newsletter stand out in the inbox.

Monetization

The Washington Post’s Anjali Iyer wrote an article for The Audiencers about how they use the post-purchase onboarding flow — both on-site and in-email — to drive engagement and reduce churn. (And lower churn means higher customer lifetime value for The Post.) Two interesting notes:
- The Post found that they had a 14-day window to engage readers after they bought a subscription. That doesn’t mean that emails or touchpoints after 14 days are irrelevant — but the first two weeks matter most.
- In A/B testing their email onboarding, they mentioned a few metrics they looked at: “Total visits, days visited within 30 days, article pageviews, habit adoption, and retention.” (You’ll note that open rate wasn’t listed here — the engagement that happens after an open is more important!)
How can you sell more newsletter ads? And what happens if one of your ad campaigns underperforms? Ryan Sager and Jesse Watkins of Who Sponsors Stuff talked with Louis Nicholls for the Send & Grow podcast to answer some of these big questions.
Jeff Giddens, president of the fundraising agency NextAfter, wrote about some fascinating trends in the non-profit giving space. There are a few trends here about recurring donors and donors who get marketing messages on multiple channels (i.e. email and physical mail) that are worth reviewing.
Loved this, from Patrick Griffith of KERA, in a post for Greater Public, about how KERA was able to significantly improve donor retention by making one change: Encouraging donors to give via direct bank withdrawal instead of credit card.
- Speaking of payments: Any independent writer or creator should check out this post, from Growth Croissant’s Reid DeRamus, about tactics to take to handle credit card payment issues. (These payment failures are a huge source of churn — as Reid writes, up to 50% of your cancellations might be because someone’s credit card expired.)
One more from the non-profit space: So many orgs think about the fundraising messages they’ll send — but have you thought about the thank you emails you’ll send after someone donates? Ann Green wrote about that process and shared a few ideas that might be worth implementing.

Growth

Fun story from Growth In Reverse’s Chenell Basilio about how one man built a newsletter about pickleball to a list with 150,000 subscribers. My favorite nugget in here: This newsletter, The Dink, created their own awards, which helped drive additional publicity and attention for their newsletter.

Content Strategy

Becky Pierson Davidson wrote about one thing to add to your summer to-do list: Talking to your audience. She outlined a few steps she recommends when doing 1-to-1 interviews with customers or readers.
I really enjoyed this guide, from Janet Aronica of Klaviyo, about two different types of automations: A drip series (that everyone receives based on when they signed up) and a nurture series (based on a user’s engagement/behavior). This guide’s aimed at businesses that are selling products, but I think many Not a Newsletter readers will get value from it regardless of where they work.

Tests, Experiments, or Learnings

This was really interesting: AdExchanger’s Anthony Vargas wrote about Daily Voice, a series of local news sites, which has won back about 350,000 inactive readers on their email list. The secret? They worked with LiveIntent to identify the readers who’d stopped opening emails but who still regularly visited their website, and used that to trigger a winback series.
- Looking for ideas on emails to send to win back inactive readers? Here’s a guide I published in April that can help.
A few speakers at ConvertKit’s Craft + Commerce conference were kind enough to publicly share their talks from the event. Two you should make time for: Alyssa Dulin, head of deliverability at ConvertKit, talked about tips for staying out of the spam folder, and Jay Clouse of Creator Science talked about creating content with a long-term mindset.

Stuff I Loved This Month

I thought this was very interesting: Tim Griffin, the attorney general of Arkansas, wrote an op-ed for Politico calling out politicians who send emails claiming that any campaign donation will be matched — even if the “match” doesn’t exist and will never happen. I’ll quote this section directly, because if Griffin actually follows through on this promise, it’d be a fascinating step in American political fundraising:

I have intentionally avoided naming names in this column because my goal is not to embarrass or single out bad actors. The practice is so widespread, it would be impracticable to list them all here. More importantly, that’s not the point anyway. I am writing this to bring awareness to the problem and notify those who fundraise on deception that they do so at their own peril. In Arkansas, political campaigns and consultants who use this tactic should know that I will inform Arkansans and take appropriate legal action. Arkansas grants my office broad authority to investigate scams both under our Deceptive Trade Practices Act and the criminal code. And I will use it.

Something I always tell clients: It takes time to build a great strategy. This case study, from Jennifer Mizgata for INN, about how Bridge Michigan used reader engagement to drive more membership revenue, is a fantastic example. The journey for Bridge to really build a membership strategy dates back to a strategy shift that started in 2017 — and six years later, they’re starting to see amazing returns.
If you’re working in the ecommerce space, here’s an endorsement: Subscribe to the “Ecommerce Marketing School” podcast, hosted by friend of the Google Doc Val Geisler.
I’ve been quietly fascinated by Duuce, a marketplace for buying and selling newsletter — which, itself, has been bought and sold twice! Newsletter Circle’s Ciler Demiralp interviewed Kévin Jourdan, who bought it (in December 2021) and sold it (in June 2023) about why they decided to sell.
Thanks to the American Press Institute and Nieman Lab for sharing Inbox Collective stories this month with their readers!

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 Pigeon!

A group of pigeons is called a “flock.”
Pigeons can fly unusually long distances — up to 700 miles in a single day. It’s the reason why throughout history, so many societies have used pigeons to transport information quickly from one point to another. Pigeons were commonly used during wars — during World War I, for instance, the U.S. military worried that enemy forces might intercept their messages, so they trained thousands of pigeons to transport news across the continent. As Livia Gershon wrote in a piece for JSTOR Daily:

“That fall, hundreds of pigeons served during the Battle of St. Mihiel and the Meuse-Argonne Offensive. In one case, men trapped by German forces sent out a pigeon named Cher Ami, which completed its mission despite being wounded by enemy fire, helping rescuers find the survivors.”

Pigeons are still used today for transporting information from one place to another. Just last month, I read a story in Reuters about police in India’s eastern state of Odisha, who keep a flock of 100 pigeons at the ready in case communication systems go down due to a natural disaster. (“Even in the unlikely event that every mode of communication breaks down tomorrow, the pigeons will never fail,” a local historian told Reuters.)
In most areas, you’ll see plenty of baby birds, but rarely baby pigeons. Why not? There’s a surprisingly simple answer: Baby pigeons don’t leave the nest until they’re grown.
Breeding pigeons is a surprisingly lucrative line of work. Here’s a 2019 headline, from Vice, as proof: “I Sell Pigeons for a Living and Earned £80,000 from One Sale.”
And I couldn’t leave this out: Mike Tyson — yes, that Mike Tyson — has a passion for raising pigeons. He told one interviewer in 2011 that he owned thousands of pigeons, including hundreds on a roof in Brooklyn. If you’ve got six minutes and want to see a side of Mike Tyson you’ve never seen before — Mike Tyson talking lovingly about his relationship with pigeons! — watch this.

Anyway, the Pigeon! That’s your (Not a) 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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