Dose #181: Retention Is Built on the Basics: Email, Empathy, and Effort

Matt here with your weekly Subscription Prescription 💊

This week we’re talking about some of the best basics to focus on in retention, with your welcome flow, using empathy in communicating with subscribers, and why worrying about your brand too much may be hurting retention.

This week’s dose is also an interview with Alyssa Wallace, one of my favorite people in retention. She’s worked with brands like Brez, Gorilla Mind, and Origin. Listen in on your favorite platform:

You Don’t Need Fancy. You Need to Give a Damn.

Most brands I work with aren’t failing because they lack vision. They’re failing because they’re skipping the basics, overcomplicating the things that should be simple, and undervaluing effort in the name of staying “on brand.”

The truth is, most of what works in retention comes down to doing the simple things really well - and caring enough to show up in ways that actually feel human.

Here are three lessons I’ve come back to again and again this year.

1. If your welcome flow is weak, your whole lifecycle is weak

The welcome flow is where most brands start - and where most of them stop thinking. If there’s anything set up, it’s usually a single, templated email that looks like it was rushed out to check a box. No intro. No tone of voice. No effort.

But your welcome flow is your first impression. If someone gives you their email, they’re raising their hand. That’s your window to start a real relationship. Even a plain text message can work wonders — as long as it feels intentional and personal. You wouldn’t meet someone at an event and hand them a PDF. You’d introduce yourself, ask questions, and try to connect. Your welcome flow should feel the same.

The brands that do this well sound like a person, not a bot. They reinforce why someone signed up. They preview what’s ahead. And they make you feel like there’s someone behind the curtain who actually gives a damn.

2. “On brand” is not a strategy - especially if you’re not big yet

I’ve lost count of how many times I’ve heard someone say “That’s not on brand” in a meeting… only for that decision to cost them real money.

Here’s the thing - worrying too much about what’s “on brand” is like a 13-year-old obsessing over their personal philosophy. You’re still growing. You need room to try things. The best learning comes from breaking your own mold a little. When you spend too much time thinking about what you should or shouldn’t be doing, you’re forgetting the most important lesson: what would your customers want to see or hear from you?

That doesn’t mean you should chase every hack or run shady offers. But if you’re afraid to send a follow-up email or test WhatsApp because it feels off-brand, you’re letting vanity outweigh performance. A clear, respectful message that converts is always more valuable than a perfectly branded one that gets ignored.

3. Fix churn with empathy instead of discounts

Most post-cancel experiences are lazy. The brand gets a cancellation request and fires off a generic discount offer, hoping to bribe the customer into staying. But that’s not why most people cancel — and you’re not going to save a subscription if you haven’t taken the time to understand what went wrong.

One of the most effective things I’ve seen is simple: record a short video for each cancel reason. Not one video, not a generic “please stay” — but thoughtful, specific responses. “Not seeing results yet?” Here’s what to expect. “Too expensive?” Let’s talk about how to get the most out of your order.

It doesn’t need to be fancy. Some of the best-performing videos are just founders walking around their kitchen. But they’re real. And that extra 60 seconds of effort can literally double your save rate. You’re reminding the customer why they signed up in the first place. And you’re treating them like a person, not just a subscription ID.

The bottom line:

Retention isn’t magic. It’s basics done better than most people are willing to do them. Write better welcomes. Stop hiding behind “brand.” Show real effort where it matters. You don’t need fancy. You just need to care.

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

 - Matt Holman 🩺

The Subscription Doc