Matt here with your weekly Subscription Prescription 💊

Some of my favorite brands were founded by a problem-solver turned entrepreneur. In this week’s dose, we dive into “Love Me Gluten Free” a subscription business started by Jenny Finke. We dive into three core tenets of her success: building a community, scaling operations, and establishing trust.

This week’s dose is also an interview with Jenny Finke. Listen in or watch on your favorite platform:

💊 Building Community, Then a Business

This week, I want to talk about one of the most overlooked growth levers for subscription businesses: building for a community you deeply understand. It’s easy to get caught up in funnel metrics and offer testing, but none of that matters if you aren’t solving a real problem in a way that feels personal to your customer. I recently had a conversation that reminded me just how powerful this focus can be.

Here are the key takeaways from that discussion that I think every subscription founder needs to hear.

1. Community First, Product Second

One of the most common mistakes I see brands make is starting with a product and then scrambling to find people to sell it to. But when you build a business that starts with a community, the product becomes a natural extension of what they’re already asking for. That’s when growth feels organic.

This doesn’t mean you need millions of followers before you launch. It means you need a deep understanding of the real challenges your target customer faces. When you’ve built trust by sharing knowledge, providing solutions, and being in the trenches with them, the leap to “here’s a product I made for you” becomes seamless. It’s not a hard sell. It’s a continuation of a relationship you’ve already built.

If you know your audience's struggles better than anyone else, you don’t have to guess what they want next. They’ll tell you.

2. The Hardest Part of Subscription is Operations (and It Sneaks Up On You)

Everyone loves to talk about growth, but not enough people talk about the physical and operational challenges of running a subscription business. As you scale, logistics go from being a minor annoyance to a massive bottleneck. Whether it’s sourcing enough product, managing fulfillment, or simply packing and shipping boxes, these tasks will quickly consume your time and resources if you aren’t prepared.

At the beginning, you can get away with doing it all yourself. You can drag pallets into your garage, ask your family to help, and hustle through it. But that strategy has an expiration date. Scaling subscriptions requires shifting from scrappy hands-on work to building systems, hiring help, and partnering with fulfillment experts who can handle volume while preserving customer experience.

Ignoring this reality is one of the reasons subscription businesses burn out. Plan for scale earlier than you think you need to. One of the best ways to do this is with the support of other founders and mentors that have done it before.

If you have any questions about logistics or operations, hit reply and let me know. That’s something I spend a lot of time in.

3. Subscription Success is Built on Trust, Not Transactions

There’s a misconception that subscription is about locking people into recurring revenue. The truth is, if you don’t build trust, you won’t keep them. Every interaction with your customer needs to reinforce the belief that they made the right choice.

In a niche like gluten-free products, this becomes even more important. The customers aren’t just looking for a convenient box of snacks; they need to trust that every product is safe and thoughtfully chosen. That’s why building a feedback loop with your subscribers is critical. Whether it’s through social content, newsletters, or personal outreach, your community wants to know that their voice is heard and that you are curating experiences with their needs in mind.

Subscriptions work best when they feel like a relationship, not a trap. If you approach your customers with that mindset, you’ll build a business that’s resilient, loved, and talked about.

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

 - Matt Holman 🩺

The Subscription Doc