Matthew Holman doesn’t sell subscriptions. He diagnoses them.

As the founder of The Subscription Prescription, he’s spent years helping brands diagnose why their subscription models succeed or lose customers. His consultancy began with a simple observation: most subscription problems seem complex but are often variations of the same core mistakes.

This conversation unpacks why certain products succeed or fail as subscriptions and explores practical tactics to boost subscription performance.

The LTV trap everyone falls into

Most brands think of subscriptions as a retention tool. They’re not wrong, but they’re not right either.

The real benefit is baked-in lifetime value. When you’re spending £60 to acquire a customer who makes a £50 first purchase, you’re losing money and hoping retention marketing fixes it later. Add a subscription option, and suddenly that same customer is worth £120 to £150 upfront.

You can afford to spend more to find them in the first place.

This explains why many brands push subscriptions first. It’s also why private equity values them when assessing your business. Higher LTV means higher multiples and a bigger payout for you.

But (and this matters) subscriptions aren’t the only way to drive up lifetime value. They’re just usually the best way.

Repeat purchases and genuine customer engagement work too. They’re just harder to guarantee.

When subscriptions don’t make sense

Matthew mentioned pillowcase subscriptions. Someone decided you should replace your pillowcases annually rather than use them until they wear out.

This is subscription thinking at its worst: taking something people use periodically and trying to force it into a recurring revenue model. Cleaning supplies, replacement cartridges, things you might need occasionally but not on a predictable schedule. The subscription box exists, the business case doesn’t.

The question isn’t “can we sell this on subscription?” It’s “does this thing get consumed on a predictable enough schedule that people will actually stick around?” Coffee yes. Pillowcases no.

The test is simpler than most people make it out to be.

Offers matter more than you think

Here’s where things get interesting for anyone who cares about conversion optimisation (which, if you’re interested in the Browse Basket Buy podcast, presumably includes you).

Matthew worked with a wellness brand that offered a standard subscribe-and-save: 10% off if you commit to recurring orders. Fine and predictable, but with thoroughly mediocre results.

They tested a different approach. Join the subscription, get your first order at 50% off, then pay full price on subsequent orders. Subscriber acquisition went up 150%.

The maths is obvious once you see it. People discount future costs heavily. A big saving now beats a modest saving forever. Loss aversion works in reverse: the pain of paying full price later doesn’t register as strongly as the pleasure of getting half off right now.

This isn’t revolutionary psychology. It’s just rarely applied to subscription design because everyone’s too busy copying what everyone else does.

The cancellation video nobody sends

When someone tries to cancel their subscription, most brands respond with a digital wall with offers, discounts, and automated pleas to stay. It feels like a retention algorithm in panic mode.

Matthew’s advice: record a one-minute video. Founder or brand rep. Explain why you started, your goals, and why you’d like them to stay. Shoot it on your phone, keep editing minimally, and make it personal.

Brands doing this are seeing save rates jump from 5% to 15%. That’s tripling your retention at the exact moment people are walking out the door, using technology that has existed since 2007.

The reason it works is painfully obvious: people have forgotten there are humans behind the subscription. The video reminds them. Some of them remember they actually liked what you were doing and decide to give you another month.

The billing reminder everyone ignores

Your billing reminder email probably says “Your order is being processed” or “Payment successful.” That’s just basic transactional communication.

Matthew’s point: you’ve got someone’s attention at exactly the moment they’re thinking about whether they still want to be a customer. Why are you wasting it on administrative updates?

Use that email to remind them why they signed up. What problem are you solving? What they’d lose by cancelling. Not in a desperate, please-don’t-leave way. In a “remember that thing you cared about last month?” way.

One client tested adding value-focused messaging to their billing reminders. Churn dropped noticeably. Not because they discovered some secret psychological hack, but because they stopped treating a retention opportunity like a receipt.

The technology trap

Ask Matthew about subscription platforms, and you’ll get an answer most tech vendors would hate: you’re probably not using your existing tool well enough to worry about switching.

There are differences between Recharge, Skio, Stay AI, Loop, and all the usual suspects. But most brands are chasing features they don’t need because they haven’t worked out what their subscribers actually want to do.

If you sell a single SKU, swapping products may not matter. If customers frequently change flavours or variants, that feature becomes important.

Identify your main use cases. Then choose tech that handles those tasks well, not just what looks impressive or offers many features.

Matthew recommends tools like Zaymo (interactive email embeds for Klaviyo that let people skip orders or add upsells without leaving their inbox) and LiveRecover (live agents helping with abandoned carts and subscription upgrades).

But he’s clear: sort out your strategy before you start shopping for software to execute it.

What to do this week

Two immediate actions if you’re running subscriptions:

First, create that founder cancellation video. The Subscription Prescription has a free template at thesubscriptiondoc.com. Upload your brand info to ChatGPT, get a one-minute script, and shoot it on your phone. A couple of hours’ work for a potential triple-digit improvement in save rates.

Second, fix your billing reminder email. Stop treating it like a receipt. Add messaging about why they subscribed, what they’re getting, and what they’d lose if they cancelled. Not desperate. Just present.

Longer term: test your offers. The standard subscribe-and-save isn’t always the best. Try front-loaded discounts, different percentages, or bulk options. See what really drives acquisition and retention.

The real insight

Subscriptions make customer acquisition economics work by increasing lifetime value.

Make sure you know what motivates signups, retention, and winning back leavers.

Winning brands think about customers, not just tactics.

Clear thinking stands out in a copycat industry.

This article was written with the assistance of AI.