Dose #179: Why the fastest-growing subscription brands don’t care about LTV (at first)

Matt here with your weekly Subscription Prescription 💊

Ever wonder how the fastest-growing subscription brands scale so quickly? This week, I’m breaking down the real playbook - what they’re doing with offers, upsells, and retention that actually works. It’s full of ideas you can steal and apply right away.

This week’s dose is also a full podcast episode. Listen to me ramble about this in greater detail on your favorite platform:

📈 The Growth-at-All-Costs Playbook

The most successful subscription brands I’ve worked with aren’t always the best at subscriptions. In fact, many of them don’t think of themselves as subscription-first at all.

But they’re world-class at one thing: growth.

They’re buying traffic, testing offers constantly, and using subscriptions not because they’re loyalists to the model, but because recurring revenue gives them margin to scale. Here’s what they’re doing differently — and what you can borrow for your own brand:

1. Your first order matters more than your third

High-growth brands are obsessed with first order profitability. They want to make money on that first transaction — not months later — because that allows them to reinvest in acquisition and grow fast.

That means:

• Creating bulk options or 2-person kits to increase AOV

• Testing “free for life” or seasonal giveaways (like ButcherBox’s “free turkey” or “free wings”)

• Charging for shipping on renewals but offering it free on the first order

They're making the first purchase feel like a no-brainer. If you’re spending too much time worrying about month 3 retention and not enough on how compelling your first offer is, you’re missing the bigger lever.

2. Bad frequency alignment kills good retention

The #1 reason I see subscriptions churn is poor alignment between consumption and delivery.

You can have a great product, but if someone gets 3 bags of protein on day one and isn’t close to finishing bag one by the time the next shipment hits, they’re going to cancel — even if they love you.

The irony here is that the fastest-growing brands are still pushing hard for high AOV on the first order, even if it makes retention harder. With a lot of growth, they’re focusing on fixes for retention.

And, the fix is simple:

• Make frequency changes stupidly easy (1-click SMS or portal updates)

• Use billing reminders to check in on usage, not just announce charges

• Align your onboarding with the reason they bought in the first place

Retention starts when the product shows up — not when the first cancel attempt does.

3. It's easier to improve acquisition than retention — until it's not

Brands doing $10M/month aren’t there because of better flows or better cancel saves. They got there by being excellent at testing creatives, offers, and order structures — and running those learnings on repeat.

But here’s what comes next: plateau.

Acquisition gets expensive. New channels get messy. That’s when retention actually starts to matter.

So if you’re a smaller brand right now, remember this: better retention won’t save a weak offer, but a better offer can fuel a long-term customer if you follow through on product, frequency, and communication.

That’s when other tactics, like new products, cross-sells, and upsells into longer subscription commitments take over too.

Bottom Line
Subscription growth isn’t about playing it safe. It’s about testing until something hits — and then retaining like your next round depends on it.

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

 - Matt Holman 🩺

The Subscription Doc