Matt here with your weekly Subscription Prescription 💊

The three places where your subscription program will either live, or die - a product that does the job, fresh offers and creative, and healthy contribution margin.

This week’s dose is also a full podcast episode. Listen or watch on your favorite platform:

💊 Why Subscription Brands Really Fail (And How to Fix It)

There’s a pattern I’ve seen over and over again, whether I’m working with a brand doing 100 orders a month or 100,000. The complexity might scale, but the root issues are often the same. And if these aren’t addressed early, they’re the fastest way to watch your subscription business stall out or collapse entirely.

Here are the three major failure points that subscription brands encounter, along with strategies for addressing them.

1. Your product isn’t solving the real problem

When a brand isn’t growing or is slowly bleeding out subscribers, the first thing I look at is the product. Not just the quality or price, but whether the product actually solves the problem that brought the customer in.

Too many brands get caught up in being “better” than competitors. More potent ingredients, cleaner formulas, slicker packaging. But better is meaningless if it’s not aligned with what the customer actually wants to achieve. Are they buying mushroom coffee because of functional health benefits? A morning ritual? Mood or focus? Until you understand that underlying need, you’re just throwing features at a problem you haven’t defined.

The brands that scale are the ones obsessively focused on that alignment between product and purpose. They’re not chasing perfection. They’re delivering clarity and then building products around that core solution. If your product doesn’t hit the mark today, you have to either improve it or reposition it until it does.

2. Your offer is stale and your creative is doing too little too late

The second failure point is around how you get people to subscribe in the first place. I’m talking about content, creative, and your actual offer. You can have the best product in the world, but if your content isn’t driving curiosity and your landing page doesn’t make a compelling offer, you’re not converting. And if you’re not converting, you’re not growing.

Way too many brands rely on basic subscribe-and-save discounts. That’s fine at the start, but eventually you’ll cap out. To push through the plateau, you need to test everything: gifts, bundles, trials, prepay incentives, and even subscription experiences tailored to specific audiences or traffic sources.

This is also where brands get stuck trying to scale across new channels. Creative that works on Meta may fall flat on TikTok. What converts cold traffic won’t always work in email. But if you’re not testing different offers, different creatives, and different pages, you're eventually going to hit the wall where churn outpaces growth and your numbers flatline.

3. You don’t have a handle on your cash flow and contribution margin

The last one is the silent killer: cash flow. You can’t rely on vanity metrics or top-line revenue to tell you how your business is doing. You need to understand contribution margin, or what each subscriber actually brings into the business after costs. And you need to track how that money flows back into the business over time.

This is especially important for subscription brands, as revenue comes in differently. Some subscribers prepay quarterly or annually. Others churn after one month. Without clear visibility into that cash conversion cycle, you’re making guesses instead of strategic decisions.

Most brands I talk to aren’t segmenting their cohorts or measuring profitability by channel. They’re not tracking what their YouTube customers are worth compared to their Meta customers. But once you do, you can double down on what works and cut what doesn’t. This is also where longer-term subscription plans can provide more predictability and front-loaded cash to reinvest in growth.

Wrapping Things Up

If you’re building a subscription business and things feel harder than they should be, take a step back. Look at the product and ask whether it truly solves the problem your customers have. Revisit your offer and test something better. And stop waiting until the end of the month to find out if your cash is going to hold up.

These are the pieces that determine whether your business stalls or scales.

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

 - Matt Holman 🩺

The Subscription Doc