Matt here with your weekly Subscription Prescription 💊

This week’s dose is a hard-hitting call out for those areas you should be worrying about to keep subscribers: cancellation flows, onboarding emails, and loyalty redemption.

This week’s dose is an interview with Cameron Gawley, CMO at GardenCup and fractional CMO of many other DTC brands. An interview you can’t afford to miss, so listen on your favorite platform:

💊 Why Your Retention Problem Starts With How You Launch

Too many brands still treat subscription like a checkout option instead of a business model. In this issue, we’re talking about the mindsets that actually scale subscriptions—not just land a few repeat orders. This week’s dose will change how you think about trial offers, retention strategy, and your very first touchpoint with customers.

Here’s what every brand should be rethinking:

1. Your Retention Strategy Starts Long Before the First Charge

Let me say something that’ll make a few acquisition teams sweat: most churn is caused by bad acquisition. If you're spending to acquire the wrong customers, there's not a magical email flow that can fix it later. The people you target, the promise you make, and the experience you deliver from day one are the biggest predictors of LTV.

We’ve talked a ton in past doses about the power of pushing a subscription offer up front, because when you find someone ready for that, you can unlock both acquisition and retention.

However, not every brand can make that initial subscription offer work, and discounting the product just brings in the wrong customers. There are other options to consider, like trial sizes.

Instead of pushing people into a full-price subscription on the first visit, give them a reason to fall in love with the product first. You lower the commitment and raise your chances of converting them into real, high-intent subscribers. And when you treat that first purchase like a bridge—not a trap—you start building actual trust.

2. Great Retention Is About Ritual, Not Just Replenishment

It’s easy to assume that subscriptions are all about convenience. However, the real stickiness comes from integrating into your customers' daily lives. If your product can become part of their morning routine, their nightly wind-down, or their fitness flow, that’s where the magic happens.

The brands that win don’t just automate reorders—they shape habits. Think about it: your magnesium powder, your matcha, your favorite elixir—they’re all habitual. The best retention move you can make is to stop asking how to make reordering easier and start asking: how can this product become part of someone’s lifestyle?

You can start this ritual by showing people in ads using your product the way someone would every day, and on the landing page too. Then, as part of onboarding and unboxing, find ways to reinforce habit-forming activities.

3. Loyalty Starts With Belonging, Not Points

If someone cancels, it’s not because your product isn’t useful. It’s usually because they didn’t feel connected to it. Brands often think retention is transactional—discounts, perks, loyalty programs. But none of that matters if customers don’t feel a sense of identity in what you’re doing.

That’s why community and storytelling aren’t fluff—they’re core retention levers. The more your customers understand your “why,” the more likely they are to stick. And when you weave that narrative into your unboxing, welcome flows, and sampling experiences, you create the kind of emotional hooks that no discount can match.

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

 - Matt Holman 🩺

The Subscription Doc