Here’s why your next newsletter isn’t going to spam

At my last job I was tasked with launching a newsletter, and was suddenly faced with a bunch of unfamiliar acronyms: DKIM, DMARC, SPF. (Apparently that last one is not related to sun protection?)

So I texted Al Iverson (not the basketball player), who’s been working in email deliverability since the dawn of mainstream internet, and asked if he could help me figure out what I really needed to know.

Since you (probably) don’t have Al Iverson’s phone number, I chatted with him last week about email deliverability, owned audience, and windmills.

Meet the Master

Al Iverson

Industry research and community engagement lead, Valimail, and Deliverability consultant and publisher, Spam Resource

• Claim to fame: Al’s been working in email deliverability since before the term even existed, including a 15-year stint at Salesforce as its director of deliverability.

• Fun fact: He programmed all the computers in his high school’s Mac lab to play “Stayin’ Alive” for alerts instead of beeping. Old-school Macs couldn’t multitask while beeping; you had to listen to the entire 4-minute song.

Lesson 1: Audience engagement has a technical component.

“Every once in a while, you run into something really strange, like Microsoft blocking emails that have the word ‘windmill’ in the subject line,” Iverson says. 

“Did you say windmill? Like … Dutch windmills?” I ask, making sure I’ve heard him correctly.

“We have no idea why,” he says, and I certainly can’t begin to guess. [Iverson clarified for me later that this is a fictional example, meant to represent how odd spam-filtering can be, and why you shouldn’t get too hung up on specific words. You’re safe, windmill fans!—ed.]

But “Free!” and “Buy now!” are probably okay, he tells me, further scrambling my brain..

Even more counterintuitively, Iverson says that using a swear word in a subject line isn’t necessarily a guaranteed trip to the spam filter anymore.

The real lesson here isn’t about some quixotic pursuit of The Ideal Email, it’s that there are persistent myths in email deliverability — and it pays for you to get acquainted with them.

For starters, Iverson suggests a healthy skepticism of any “top 200 words to avoid in your subject line” lists. And Gmail “wants to make sure that the subject line and sender information actually connect to what’s in the body of the email,” so it’s “actually very sensitive” to outdated ideas like starting a bulk email with “Re:.”

In other words: Pay as much attention to the technical side of audience engagement as you are to creating excellent content.

Lesson 2: Own your identity.

“Why do people love email so much?” Iverson asks. “Because it is a platform that is open to all.” Platforms like Instagram and TikTok — aside from needing some basic video editing and possibly dance skills — are owned by corporate entities out of your control. Although individual email platforms like Gmail have a lot of influence when it comes to deliverability, your email audience is your own.

And, says Iverson, email “gives us this channel to connect with people without being beholden to these specific platforms.” The flip side of that is that “if you don’t have the technical ability to take control of those levers that put it more into your control, you can still get similarly stuck.”

If you’re new to email newsletters, any one of the major platforms is a great place to start. But the more technical know-how you have (or can hire), the more you can do things like sending from your own domain, putting you just a little bit more “in control of your own destiny, both from a deliverability perspective and from a long-term branding and marketing perspective.”

Lesson 3: Stop chasing subscriber count.

“People live and die by their subscriber counts,” Iverson says. But “if you have 10 million subscribers, but a very low open rate, your emails are more likely to go to the spam folder.”

The primary reason that an otherwise good newsletter might land in the spam folder is lack of engagement. “The more you focus on people who are actually interested enough to interact with your mail, the better reputation you have with the mailbox providers, so you’re more likely to get to the inbox,” he says.

“And, long story short, what prevents spam folder placement isn’t how many subscribers you have — it’s high engagement.”

Maximize high engagement by “implementing a subscriber lifecycle management process,” says Iverson. Suppressing inactive subscribers, segmenting your audience, and being transparent about your practices are all key to your newsletter’s ultimate success.

Lingering Questions

This Week’s Question

If you could only invest in one tool to help your company grow for the next three years, what tool would it be? —Ryan Atkinson, Founder and CEO of Spacebar Visuals

This Week’s Answer

Iverson: In the context of email marketing success, inbox placement, and deliverability, this means investing in a deliverability testing and monitoring platform (like Inbox Monster, for example). If your revenue depends on successful email marketing, you’re running blind without something like this. Whether your email gets to the inbox isn’t something you can easily track on an email marketing platform; there’s no “which folder” disposition information sent back to the sender or send platform as part of the email delivery process. A tool like this, and the expertise that comes with it, guides you on how to interpret results and make strategic adjustments to remediate or prevent issues.

Next Week’s Lingering Question

Iverson asks: What’s one marketing habit or best practice you think we should collectively leave behind, and what would you replace it with?