Dose #142: Three Compelling Questions Answered

Matt here with your weekly Subscription Prescription 💊

This past week I took three questions from Twitter and turned their answers into this newsletter dose. Read on to hear how brands of different sizes behave, how you can get a single SKU product to acquire more subscribers, and unique cancellation questions to improve retention.

This week’s dose is also a full podcast interview! Give it a listen on YouTube, Apple Podcast, or Spotify:

Scaling Subscriptions: What Separates $1M, $10M, and $100M Brands?

This week, I’m tackling three questions I got from social media. Great questions with answers that should be shared.

1️⃣ What separates a $1M, $10M, and $100M subscription brand?
2️⃣ How can a single-SKU subscription stand out and improve conversions?
3️⃣ What are some unique cancellation reasons and questions that work?

Let’s break it down.

1. The Big Leaps: $1M → $10M → $100M

Every subscription brand wants to grow, but what gets you to $1M won’t get you to $10M, and $10M strategies don’t necessarily scale to $100M.

The question of how brands are different at these different revenue levels is certainly more complex than I can get into here, but my answer is that I see big differences between $1M, $10M, $30M, and then $100M.

Here’s how the game changes at each stage:

• At $1M, most brands rely on one hero product and one marketing channel (often Meta Ads). At this stage, the focus is on proving the model, optimizing for CAC, and nailing product-market fit.

• At $10M, brands typically expand their SKU lineup and start testing additional acquisition channels like Google, TikTok, and influencers.

• At $30M+, growth from digital marketing alone starts to slow down. Many brands shift into retail (Target, Walmart, Whole Foods, etc.), but that introduces a new problem: how do you keep people subscribing when they can now grab your product in-store?

One key mistake I see at growing companies? Losing alignment between growth and retention. If growth teams optimize for cheap conversions, but retention teams struggle with high churn, you’re acquiring the wrong customers. Your teams need to be aligned on customer lifetime value (LTV) as the north star.

Bonus Tip: the best hack for growing past $1M all the way up to $30M+ is cracking killer offers. Keep testing because it will unlock better conversions AND LTV when done well.

2. How to Differentiate a Single-SKU Subscription

If you only sell one product, you need a compelling reason for customers to subscribe instead of buying once. There are two simple ways to make that happen:

💡 1. Offer a unique bonus or free gift.
A small add-on can be the nudge that turns a one-time purchase into a subscription. The key? Make it useful and unique—something that makes the core product better. A protein brand could include a premium shaker bottle. A skincare brand could offer an applicator pad.

💡 2. Create multi-month commitment tiers.
Instead of a simple “subscribe and save 10%,” give customers options:

• Monthly subscription → 10% off

• Quarterly subscription → 15% off

• 6-month subscription → 20% off + free gift

Even if only 5-10% of people choose the longer commitment, that’s a massive impact on retention and profitability.

If you only have one product, you can look at product expansion as an opportunity to improve your offer and retention efforts. You don’t need to launch an entirely new product line, so much as introduce it to existing and potential customers of your hero product.

3. Smarter Cancellation Flows = Higher Retention

Most brands make two big mistakes with their cancellation flows:
1️⃣ They don’t ask the right questions.
2️⃣ They don’t do anything with the answers.

If your cancellation reasons are too broad, you’re missing out on actionable insights. For example, instead of just “I have too much product,” split it into:

• “I have too much on hand, but I want to stay subscribed.”

• “I never even started using the product.”

Those are two very different problems—one needs a frequency adjustment, while the other might need a little education and a discount to encourage them to start with the product.

Similarly, “It’s too expensive” could mean:

• “I can’t afford it right now” → Offer a pause option or temporary discount.

• “I don’t see the value” → Show a message reinforcing why it’s worth the price.

A well-optimized cancellation flow won’t save everyone, but it will give you better data and keep more customers than you’d expect.

As you collect cancellation reasons, use that feedback to improve how you onboard subscribers, the quality of your product, or address potential objections before they happen.

Remember that the more specific you can get with cancellation reasons, the more specific your treatments for those reasons can be.

Final Thoughts

Scaling a subscription brand is about smart shifts in strategy at the right time. Whether you’re working to hit $10M or figuring out how to keep growing past $30M, the key is balancing acquisition, retention, and product expansion without losing focus on your most valuable customers.

Got a question you want answered in an upcoming issue? Reply to this email or drop a comment on social—I’d love to tackle it next.

That’s it for this week’s dose—see you next Tuesday for #143!

 - Matt Holman 🩺

The Subscription Doc