The Opportunity Podcast · 2026-05-12 · 54 min
For many eCommerce brands, getting the first sale is not the hardest part. Keeping customers coming back is. In this episode of the Opportunity Podcast, Greg speaks with Matthew Holman, founder of D2C subscription agency Subscription Prescription , about how eCommerce brands can improve retention and increase recurring revenue by adding a subscription component to their business.Matt explains why subscriptions are often misunderstood by founders. Many brands treat them purely as a way to increase lifetime value, but according to Matt, the real opportunity is creating a better customer experience that naturally drives recurring revenue. Good onboarding is key. Matt explains that the first 7 - 10 days after a purchase are critical because that is when customers decide whether they feel like they are "winning" with the product. Brands that educate customers early, guide them through the experience, and reinforce value tend to see far stronger retention. Greg and Matt also dive into why some ecommerce businesses force subscriptions where they do not belong, the psychology behind multi-month subscription offers, and why value stacking often works better than endless discounting.
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