The Best Email Marketing Tells a Story

Matt Ragland is a 10-year email marketer, first at ConvertKit and now at Good People Digital, the Nashville-based agency he launched in early 2023. His approach to superior email performance is storytelling.

He told me, “Brands that excel at email marketing frequently tell a story to their ideal audience.”

In our recent conversation, he and I addressed storytelling tactics, email design, automation strategies, and more. Our entire audio is embedded below. The transcript is condensed and edited for clarity.

Eric Bandholz: Who the heck are you?

Matt Ragland: I run an email marketing and course-launch agency called Good People Digital. We work with creators and ecommerce providers. We build email and launch newsletters, usually for courses and information products. I’ve been in the email game for almost 10 years.

I do a lot of things in the creator economy. I have a YouTube channel that’s just under 100,000 subscribers.

Bandholz: What is your approach to email marketing?

Ragland: I focus on a story or narrative. For ecommerce, brands that excel at email marketing frequently tell a story to their ideal audience and include their products. I would like to see more ecommerce brands bring their customers into that story in a natural way.

Creators do a good job with stories, but many are horrible at selling and promoting. And then many ecommerce merchants are good at selling, promotion, packaging, and positioning but not storytelling. Both sides have much to learn from each other.

Bandholz: Email newsletter brands such as The Hustle and Morning Brew have grown to eight-figure valuations. Walk us through that business model.

Ragland: Their revenue model focuses almost exclusively on advertising and sponsorships.

It costs very little to start an email newsletter. The Hustle and Morning Brew both went to a daily newsletter pretty early. I remember listening to the Morning Brew founders. They launched the newsletter while students at the University of Michigan. They asked people in their business classes to subscribe on paper.

It started to grow naturally from there through referrals. They had a robust referral program. Say I’m reading the Morning Brew, sign up to be a referral partner, and send it to you and 10 other people who sign up. I then get a sticker and a shirt. The Hustle did something similar.

The other thing Morning Brew and The Hustle did well was paid acquisition of newsletter subscribers. Ecommerce has been great at this for years. But more traditional newsletters didn’t understand the same way as ecommerce sellers when Facebook ads were cheap, around 2015. It felt like free money.

Bandholz: Is there any new tactic in email marketing to take inspiration from?

Ragland: A lot of people feel email marketing is old and out of vogue. But it remains among the best forms of direct marketing. In terms of new tactics, emphasize the story aspect and simplicity — making the newsletters as simple as possible and cutting back on graphics.

Try making a newsletter look more like a personal email message. A friend of mine runs a design studio called Late Checkout. He publishes a design newsletter and stripped away all of the visuals last year.

He now sends something that looks more like a letter to shareholders, which he calls “Greg’s Letter.”

Bandholz: The biggest innovation to me is campaign flows and automation. That’s how Klaviyo got traction over Mailchimp.

Ragland: Yes. Also, what Klaviyo did so well and still does is integrate SMS.

The automation piece is huge, as is the ability to have one entry point as the start for an entire flow that can upsell, down-sell, and cross-sell. We implemented it for an ecommerce client. Instead of the initial entry point of signing up for the newsletter or purchasing a product, we used a mid-life cycle automation based on interest or intent.

For example, a subscriber who clicks on a particular product or link in an email launches an automation similar to cart abandonment, with cross-sells and storytelling around that type of item.

Bandholz: Your wife is expecting your fourth child. What is your philosophy on how to be a good dad?

Ragland: I want to be a good example for my kids. I want to show them what I believe in and what being a good man is. I’ve been fortunate to have a lot of great examples in my life. I’m close with my dad, and he’s amazing. He’s always been a big supporter and fan of mine. My uncles have been excellent mentors, and I’ve had a lot of people in my life who have shown me that this is what it is to be a good man and a good dad.

Bandholz: Where can listeners follow you and learn more about your email services?

Ragland: Our agency site is MyGoodPeople.com —  AutomaticEvergreen.com is our email marketing service. They can follow my YouTube channel or contact me on LinkedIn or X — @mattragland.