On the Up Arrow Podcast, Jay Myers makes the point that asking for a subscription is a fundamentally different question than asking for a one-time sale. He argues that subscription conversion is about four times harder because it’s a deeper commitment. A customer might impulsively buy a bag of coffee to try it out, but agreeing to pay for it every month requires a level of trust you probably haven’t earned yet. In the customer's mind, the one-time purchase is their way of vetting you and your product before they even consider a longer-term relationship.
Trying to force the subscription on day one often just scares away a potential customer who might have loved your product. Jay’s framing reframes the whole question. The goal isn’t to get a subscription right away. The goal is to get the customer to try the product, love it, and then want to subscribe.
Mike Feldstein made a similar point on Honest Ecommerce, offering a concrete strategy based on this idea. He recommends focusing entirely on getting that first one-time purchase and then rolling out the subscription offer on the back end. Don’t even present it as an option at the initial checkout. His specific advice is to target customers who you know are happy, like someone who just left a five-star review, and prompt them to subscribe around the time they’d be running out of a 30-day supply. You let them tell you they like it first, then you make the ask.
Of course, there is a counter-argument. On Ecommerce Coffee Break, Rakshithaa Mahesh points out that with today’s high customer acquisition costs, this model can be dangerous. If you’re spending a ton on ads, you might actually lose money on every single one-time buyer. In that scenario, she argues it makes sense to acquire customers directly for a subscription, because the recurring revenue is the only way you’ll eventually make a profit on them. It’s a harder conversion, but it may be the only financially viable one if your margins are tight.
This entire debate obviously assumes your product is a natural fit for this model. An episode of The Bottom Line puts it perfectly: Subscription Business Models are for products with "predictable consumption cycles." Think supplements, skincare, pet food, or coffee. It’s not meant for apparel or furniture. If people don’t consume your product on a regular, repeatable basis, forcing a subscription is just asking for high churn and unhappy customers.