Dose #151: The Story Behind Subscription Prescription

Matt here with your weekly Subscription Prescription 💊

This newsletter is almost three years old! In this week’s dose, I share the story of how we got here and where we’re going. If you want to learn a bit more about me and my journey, this quick read will tell you a lot.

This week’s dose is also a podcast episode, so listen in or watch on your favorite platform:

Solving Delivery Issues for Subscription Customers

If you run a subscription brand, or have had a subscription, then at some point you’ve wondered (or been asked) - when will my order arrive?

The problem with subscriptions is that the ‘order date’ is actually a process date - meaning customers and the brand aren’t sure when an order will arrive. They know when it will process, and get tracking once it’s fulfilled, but if you’re trying to predict when an order will show up - good luck!

This uncertainty results in lost orders, wasted shipments, and churn. There hasn’t been a good way to show subscribers when their order will show up - until now!

Nextime.ai integrates with your subscription platform to show subscribers when their order will be delivered, not just processed. Customers have an Amazon-like experience, being able to select when they want to receive their order.

This functionality makes it easier on subscribers to understand when they will get their order, and easier on your fulfillment because Nextime.ai adjusts the process date to match your fulfillment and delivery timeframe.

Everyone wins with Nextime.ai!

Learn more about how Nextime.ai will work for your business.

🚑 From Shipping to Subscriptions: Why I’m All-In on Helping You Grow

As we come up on three years of newsletter issues, or weekly doses, it felt like a good time to reintroduce myself to all of you.

This week, I’m pulling back the curtain to give you the origin story behind Subscription Prescription, the journey that brought me here, and how all of it is shaping the work we do today with DTC subscription brands just like yours.

The (Slightly Risky) Career Move That Changed Everything

Years ago, I was working at a shipping logistics company called EHub here in Utah. Great people, solid company. But here’s the kicker: it’s also where I met my (now) wife—who happened to be the CEO’s sister. Yeah… dating your boss’s sister isn’t exactly the ladder-climbing move they write about in business books.

So, two things were clear:

1. I needed a fresh start.

2. I had that itch to build something of my own.

Enter: Subscriptions (and My Co-Founder)

I ended up partnering with David Bradley, the founder of a subscription software platform called QPilot. He was looking for a marketing co-founder, and I was ready to jump into the full-time responsibilities of growing a business.

David once told me:

Challenge accepted.

That’s where things took a turn—not just for me, but for the whole direction of our work.

How Subscription Prescription Was Born

As we built QPilot, we realized there was a gap in how people learned about subscriptions. Everyone was either selling a tool or pushing an app—but few were talking real strategy.

We wanted to speak directly to brands and help them grow. Not just plug in software.

So we renamed our QPilot newsletter Subscription Prescription (hat tip to David’s background in advertising), and I took on the role of “subscription doc.”

At the same time, I had been working more and more closely with our customers to understand their programs and what they needed to do to unlock stronger retention and more growth. We had access to the data behind hundreds of brands, and we took those insights to them and also to the Subscription Prescription audience.

At first, we hoped it would be a lead gen tool for QPilot. But our initial feedback was that people didn’t want to hear about the platform—they wanted help understanding subscriptions.

A Turning Point: Going Independent

That early feedback was a lightbulb moment. Brands were hungry for honest, actionable subscription advice without all the app-driven bias.

So, we made a big decision: Subscription Prescription needed to be its own thing.
Not QPilot or AutoShip.cloud (our subscription plugin). Just straight-up best practices for scaling subscription businesses.

And once we leaned into that—things took off.

The newsletter grew, and we got asked by brands on all platforms what they should do to grow.

For me, working with our customers and creating content unlocked something more motivating than marketing SaaS. It allowed me to connect directly with people and actually solve a problem instead of just selling something.

Consulting seemed like a natural fit with all the questions and what I loved doing. About 2 years ago, we started working with our first clients, and the Subscription Prescription methodology was born.

What We Do Now: From First Click to Cancel and Winback

Many people don’t realize this, but what we do isn’t just retention. That’s only part of it. I’ve seen it so often that I feel like a broken record repeating myself, but how people buy affects how you retain them.

Here’s how we work with brands today:

• Conversion-focused purchase experiences: We start at the buy box, redesigning subscription options to improve AOV and conversions.

• Onboarding & comms: We optimize how you welcome subscribers, handle upcoming billing, and stay in touch.

• Churn prevention & reactivation: We fight churn inside your app—through cancellation flows, winback offers, and more.

• Full-lifecycle strategy: From acquisition to unboxing to reactivation, we touch every point of the journey.

Because here’s the truth most brands miss:

If you’re not thinking about how you acquire subscribers, you’re setting up long-term retention problems before they ever even start.

The Real Passion Behind All This

Underneath all of this—the software, the strategies, the optimization work—what drives me is simple:

I love solving complex problems and helping others understand them too.

Whether it's shipping, CRO, or coaching subscription brands, I get fired up about helping people figure out the messy stuff. And subscriptions? They’re the perfect combo of operational complexity and marketing nuance. Fits right in with my weird background in logistics, software, marketing, and ecommerce.

This is my lane, and I’m staying in it.

Let’s Connect

If you’re curious about working together, or want to ask a question, just reply to this newsletter or shoot me a DM on LinkedIn or Twitter. I post daily content with fresh takes, ideas, and sometimes call out the occasional BS in the space.

Also—small life update—I’m now a dad to a five-month-old baby boy, and I’ve got two incredible stepkids. The same woman I met back at EHub? Yep, we’re building a life together. So when I say I’m committed to this work and this community, I mean it.

It’s been an incredible journey of finding my passion, unlocking value for the community, and building the life that brings me the most joy.

I hope you can find the same! That’s part of my why too.

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

 - Matt Holman 🩺

The Subscription Doc