Dose #147: The Most Important Subscription Strategy for 2025 (Or Maybe Ever)

Matt here with your weekly Subscription Prescription 💊

I’ve seen it over and over - the strongest lever for retention is how you acquire a subscriber. In this week’s dose, we dive into how deep discounts attract the wrong kind of subscriber, the power of bulk subscriptions, and making offers for the right subscriber.

This week’s dose is also a full podcast episode! Listen to me rant even longer on YouTube, Apple Podcast, or Spotify:

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The guide is free to download, so grab it now!

This newsletter is usually about subscriptions, which most people equate with retention. But today, I’m here to tell you that the single most important thing you can do to improve your subscription program in 2025 isn’t a post-purchase email flow, a churn survey, or even a subscriber win-back offer.

It’s how you acquire your subscribers in the first place.

I’ve audited hundreds of subscription businesses, and the biggest factor influencing retention isn’t whether someone gets a well-timed reminder email. It’s what motivated them to subscribe in the first place. If you’re not paying attention to how you structure your offers, you might be attracting the wrong subscribers—ones who are far less likely to stick around.

Let’s talk about why acquisition is the biggest lever for retention and how you can improve yours.

1. Deep Discounts Attract the Wrong Subscribers

A lot of brands lean on steep discounts to drive subscriber growth. And while discounts are a useful tool, they also come with a hidden cost: they attract price-sensitive shoppers.

Think about it—someone who only subscribed because they got 20% off their first order isn’t necessarily committed to your brand or product. They’re testing it out, and if they don’t love it, they’re gone as soon as the discount disappears.

Instead, I’ve seen gift-with-purchase offers consistently retain subscribers better than discount offers. Why? Because a free gift feels like added value, while a discount just feels like a deal. Customers who subscribe for a gift are still excited about the product—not just the price.

So if you’re relying heavily on discounting, ask yourself: are you building a customer base that loves your product, or just one that loves a deal?

2. The Power of Bulk Subscriptions

One of the best ways to improve retention and increase upfront revenue is by offering longer-term subscription options. Instead of just a monthly subscription, test offering a 3-month or 6-month plan.

Here’s a great example of what that looks like from Yo Pretty Boy:

Here’s why it works:

• Higher upfront revenue. A subscriber who commits to three or six months right away spends more than someone who’s just testing it for a month.

• Better retention rates. I’ve seen time and time again that subscribers who commit to 3+ months upfront renew at higher rates than those who start with a 1-month plan - even past the 4-month mark.

• Psychological anchoring. When you present three options—1-month, 3-month, and 6-month—the 3-month option often becomes the most appealing (the “Goldilocks” effect).

• Conversions go up for subscriptions. It may seem a little backward to add more options, but this kind of model can work much better!

If you’re not already testing this, it’s one of the easiest changes you can make to improve retention without changing anything about your product.

3. Crafting Offers That Attract the Right Subscribers

Different types of offers attract different types of subscribers. The key is to structure your offer in a way that appeals to the best subscribers—the ones most likely to stick around.

Let’s use an amusement park analogy.

Say you run a theme park and you’re trying to get more visitors. You could offer:

• A BOGO ticket deal—great for price-conscious buyers who want a one-off visit.

• A family bundle with concessions and perks—more appealing to families who will spend the whole day (and a lot of money) at your park.

Both offers drive sales, but which visitor is likely to spend more inside the park? The family that pre-committed to a larger bundle.

The same logic applies to your subscription business. If you’re struggling with retention, it’s worth looking at who your best customers are and how they entered your funnel. Did they buy because of a discount, a bundle, or an irresistible value proposition? And how can you get more of those high-LTV customers?

Key Takeaways

1️⃣ Acquisition strategy determines retention. If you rely on discounts, you’ll attract price-sensitive customers who churn faster. If you use gift-with-purchase or bundles, you’ll attract higher-LTV subscribers.

2️⃣ Longer-term subscriptions drive better retention. A subscriber who starts with a 3-month or 6-month prepay plan is more likely to renew than one who starts with a 1-month plan.

3️⃣ Not all offers attract the same customer. Test different offers (bundles, gifts, prepaid discounts) to find the one that attracts your best long-term subscribers.

If you want to see examples of high-performing subscription product pages, hit reply and ask away!

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

 - Matt Holman 🩺

The Subscription Doc