Dose #153: Email Marketing for Subscribers - Lessons from George Kapernaros

The Biggest Three Things You Need To Improve Retention

Matt here with your weekly Subscription Prescription 💊

Email marketing is still the biggest arrow in the subscriber retention quiver. In this week’s dose, we break down some of the common mistakes brands make when it comes to email for subscribers: create separate flows, keep selling the benefits, and support them through every step of the journey.

This week’s dose is also an incredible podcast interview with George Kapernaros, the founder of YOCTO. He inspired this issue and has some incredible insights on email marketing.

Listen in or watch on your favorite platform:

Join Us Wednesday: CPG Subscription Roundtable

Looking forward to being part of the panel for ‘The 10x Customer: How Personalized Experiences Drive Unstoppable Subscription Retention’ on May 7th.

I’ll be sharing proven strategies on how to diagnose and fix fragmented post-purchase experiences to maximize customer lifetime value.

I’m excited to join past podcast guests and friends like Jack and Tessa Schrupp, Chris George, and Tyler Craig! Grab your spot below for the webinar next week.

💊 Treat Your Subscribers Like a Different Species — Because They Are

In this week’s dose of Subscription Prescription, I want to unpack something that should be obvious — but somehow still gets missed by most brands: your subscribers aren’t just “regular customers.” They’ve made a deeper commitment, which means your emails, your messaging, and your strategy need to reflect that.

Here’s what I’ve been thinking about lately — and what’s working inside the most sophisticated DTC subscription programs I’ve seen:

1. One Size Doesn’t Fit Anyone: Stop Treating Subscribers Like Everyone Else

This is one of the biggest missteps I see in email strategy. Brands treat subscribers exactly the same as one-time customers. Same campaigns. Same flows. Same messaging. That’s a problem.

Because here’s the truth: subscribers have different motivations, different expectations, and different risks. Sending your standard campaigns to this group can actually cause churn. It’s not just about missing relevance — it’s about hitting the wrong nerve at the wrong time.

Your subscribers need their own email journey. That means isolating their experience, tailoring your flows, and speaking to the reality they’re living — not the one you think they’re in. When brands do this well, it shows up in lower churn, higher LTV, and better engagement.

2. Remind Subscribers Why They Signed Up — Again and Again

There’s a mindset trap that a lot of brands fall into: thinking that once someone subscribes, the job is done. That couldn’t be further from the truth.

Every billing cycle is a decision point. Every charge is a chance for them to ask, “Do I really need this?” And that question doesn't get answered by the product alone — it gets answered by how well you’ve been reinforcing the value along the way.

So your job as a subscription operator? Keep reinforcing. Keep justifying. Keep reminding. Not once. Not in a welcome flow. But consistently — in billing reminders, in check-ins, in content that speaks to their goals. And those goals evolve. Someone might be trying to lose weight in June and bulk up in November. Your emails should evolve with them.

3. The Best Subscription Emails Don’t Just Sell. They Support.

If your email strategy is just about squeezing more dollars out of your list, you're missing the point. Especially with subscriptions, where the upside of increased AOV is often outweighed by the downside of churn.

Here’s how I think about campaigns to subscribers: they should either magnify the original value of the product or reduce friction to continuing. That’s it.

That could mean showing how other customers are seeing results, or offering easy ways to upgrade or skip shipments through tools like Zaymo. It could mean asking questions about their goals and tailoring future messaging around that.

One of my favorite tactics here: embedding customer check-ins inside your flows — short surveys or quick actions to understand where they’re at and what they need. This gives you better segmentation and makes your messages feel like a real conversation, not just a broadcast.

Final Dose

Subscribers are your highest-leverage customers. But only if you treat them that way.

Don’t lump them in with your general list. Don’t assume they remember why they signed up. And definitely don’t send them six promos a week hoping to squeeze out a few more clicks.

Build an intentional journey. Reinforce the value. And meet them where they are — not just where you want them to be.

Until next Tuesday, that’s your Subscription Prescription. 💊

 - Matt Holman 🩺

The Subscription Doc