Subscription Prescription | Weekly Doses to Boost Ecommerce Revenue
Looking to sell on repeat? You’ve come to the right place. Welcome to the Subscription Prescription Podcast where you’ll learn everything there is to know about ecommerce. From establishing your brand identity online to winning the loyalty of your customers and limiting churn, nothing is off the table in these fun and informative conversations. In a world where online selling is the new way to shop, it’s important to stand out from the competition. Tune in each week to learn from industry expert, Matthew Holman, and jumpstart your ecommerce journey today!
Episodes
October 28, 2025 • 18 mins
This week, our guest host, Riley, dives into 5 overlooked post-purchase touchpoints that can make or break your subscription retention. From education to personalization to transactional SMS, she lays out the simple but powerful strategies brands often miss — and how to turn them into moments that build loyalty, trust, and long-term growth.
You’ll learn:
✔️ How to turn onboarding into a habit-building engine
✔️ Where personalization a...
You’ll learn:
✔️ How to turn onboarding into a habit-building engine
✔️ Where personalization a...
Mark as Played
October 21, 2025 • 6 mins
In this episode of Subscription Prescription, I break down my top 3 mistakes I see across DTC subscription brands—mistakes that are quietly hurting your growth and retention.
Here’s what we cover:
• Why treating subscriptions as a retention play is backwards
• How most billing reminders are killing your LTV
• The cancel flow tweak that can instantly double your save rate
Whether you're just starting out or running a high-volume subscrip...
Here’s what we cover:
• Why treating subscriptions as a retention play is backwards
• How most billing reminders are killing your LTV
• The cancel flow tweak that can instantly double your save rate
Whether you're just starting out or running a high-volume subscrip...
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October 14, 2025 • 25 mins
Most DTC brands treat retention like it’s just about sending emails or building flows. But if you’re not approaching retention with a real strategy, you’re leaving serious money on the table.
In this episode of Subscription Prescription, we hear directly from one of the best retention pros in the game: Sonja Grasser from Wellbel. She shares how to connect your data, improve your segmentation, and build habits that lead to long-term ...
In this episode of Subscription Prescription, we hear directly from one of the best retention pros in the game: Sonja Grasser from Wellbel. She shares how to connect your data, improve your segmentation, and build habits that lead to long-term ...
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October 7, 2025 • 11 mins
Black Friday Cyber Monday can be a goldmine for subscription brands - or a churn nightmare.
In this episode of Subscription Prescription, we walk through exactly how to structure your BFCM strategy so you don’t sacrifice margin or long-term LTV. Most brands treat this like a cash grab. I’ll show you how to approach it more strategically.
Here’s what we cover:
How to prevent subscribers from canceling to chase your BFCM offer
What to in...
In this episode of Subscription Prescription, we walk through exactly how to structure your BFCM strategy so you don’t sacrifice margin or long-term LTV. Most brands treat this like a cash grab. I’ll show you how to approach it more strategically.
Here’s what we cover:
How to prevent subscribers from canceling to chase your BFCM offer
What to in...
Mark as Played
September 30, 2025 • 36 mins
Most subscription brands are solving the wrong problem. They build marketing around surface-level reasons, but never dig deep enough to uncover what actually drives purchase and repeat behavior.
In this episode, we hear directly from the master of behavioral marketing with Sarah Levinger. She breaks down three marketing lessons that have changed how you should think about acquisition and retention strategy:
In this episode, we hear directly from the master of behavioral marketing with Sarah Levinger. She breaks down three marketing lessons that have changed how you should think about acquisition and retention strategy:
- Why you should stop te...
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September 23, 2025 • 37 mins
Most brands are trying to solve churn by tweaking their cancellation flows. But the truth is, if your customer doesn’t know what they need - or how often - they’re going to cancel no matter what you offer on the way out.
In this episode of Subscription Prescription, we sit down with Cherene Aubert to unpack three universal truths of subscriptions:
In this episode of Subscription Prescription, we sit down with Cherene Aubert to unpack three universal truths of subscriptions:
- Why churn is often a symptom of a buyer education problem
- How helpful beats clever w...
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September 16, 2025 • 22 mins
In this episode of Subscription Prescription, I sit down with the founder of BakIt Box to explore how rethinking subscription cadence, product strategy, and communication channels led to deeper customer engagement and better retention.
We talk about why they abandoned the monthly model in favor of quarterly shipments, how they turn subscription kits into high-converting one-time products, and what it looks like to actually serve cus...
We talk about why they abandoned the monthly model in favor of quarterly shipments, how they turn subscription kits into high-converting one-time products, and what it looks like to actually serve cus...
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September 9, 2025 • 15 mins
In this episode of Subscription Prescription, I break down how the top subscription platforms, specifically, Recharge, Stay AI, SKIO, and Loop, approach cancellation flows, and how you can optimize each one to reduce churn and increase retention.
Whether you're just getting started or managing thousands of subscribers, understanding your platform's cancellation flow is one of the highest-leverage things you can do. From splash scree...
Whether you're just getting started or managing thousands of subscribers, understanding your platform's cancellation flow is one of the highest-leverage things you can do. From splash scree...
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September 2, 2025 • 37 mins
In this episode of Subscription Prescription, I sat down with the founder of Blind Barrels to unpack how they built a whiskey subscription that people can’t stop talking about and don’t want to cancel.
We explore how intentional curation, premium unboxing, and smart pricing can turn an average subscription into a meaningful experience. You'll hear real strategies for lowering churn, building community, and designing packaging that c...
We explore how intentional curation, premium unboxing, and smart pricing can turn an average subscription into a meaningful experience. You'll hear real strategies for lowering churn, building community, and designing packaging that c...
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August 26, 2025 • 17 mins
Most subscription brands don’t fail because of ads or acquisition; they fail because of retention. In this episode of Subscription Prescription, I walk through the audit framework my team uses to diagnose subscription programs. You’ll learn:
✅ The three patterns we see in subscription brands (and what each one needs to fix first)
✅ Why weak onboarding, billing reminders, and cancellation flows quietly kill retention
✅ How bulk options...
✅ The three patterns we see in subscription brands (and what each one needs to fix first)
✅ Why weak onboarding, billing reminders, and cancellation flows quietly kill retention
✅ How bulk options...
Mark as Played
August 19, 2025 • 30 mins
Most subscription brands think growth is all about the product. But the real wins come from building community, personalizing experiences, and creating new layers of value beyond the box. In this episode, I break down what every subscription operator can learn from niche sports boxes and how you can apply the same strategies to drive retention and loyalty in your own business.
👉 In this video, you’ll learn:
👉 In this video, you’ll learn:
- Why community feedbac...
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August 12, 2025 • 20 mins
Most brands only use email and SMS to send billing notices or shipping confirmations to subscribers. That’s a huge missed opportunity. In this episode, I share how to:
- Use campaigns to deepen subscriber loyalty and reduce churn
- Turn transactional emails into sales and brand-building tools
- Leverage SMS for subscription management and higher LTV
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August 5, 2025 • 25 mins
In this episode of Subscription Prescription, I sit down with Jenny Frink, founder of Love Me Gluten-Free, to talk about how she transformed her personal health journey into a thriving subscription box business.
Jenny shares how she built a community of gluten-free eaters through her blog, Good For You Gluten-Free, and how a frustrating affiliate partnership became the catalyst for launching her own product discovery box. We discuss...
Jenny shares how she built a community of gluten-free eaters through her blog, Good For You Gluten-Free, and how a frustrating affiliate partnership became the catalyst for launching her own product discovery box. We discuss...
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July 29, 2025 • 32 mins
In this episode of Subscription Prescription, we dive into the tactics that actually move the needle on subscription retention. I’m joined by Thomas Lalas, a DTC retention expert who’s worked with brands like Everyday Dose, Obvi, and Livingood Daily.
We break down:
Why most brands lose customers in the first week (and how to stop it)
How to turn your billing reminders into a retention engine
The data-backed importance of early engageme...
We break down:
Why most brands lose customers in the first week (and how to stop it)
How to turn your billing reminders into a retention engine
The data-backed importance of early engageme...
Mark as Played
July 22, 2025 • 17 mins
Most subscription brands don’t fail because of bad luck — they fail because of three common, fixable mistakes. In this episode, I break down the core reasons subscription businesses hit a wall or collapse altogether.
We’ll talk about:
✔ Why product-market fit still isn’t enough
✔ How your offer and creative are dragging down conversions
✔ What most founders get wrong about cash flow and LTV
Whether you’re just starting out or scaling pa...
We’ll talk about:
✔ Why product-market fit still isn’t enough
✔ How your offer and creative are dragging down conversions
✔ What most founders get wrong about cash flow and LTV
Whether you’re just starting out or scaling pa...
Mark as Played
July 15, 2025 • 18 mins
In this episode of Subscription Prescription, I sit down live at SubSummit with Lina Tonk, CMO of Recurly, to unpack what’s changing in the subscription economy and why retention is taking center stage.
We explore how top brands are shifting their focus from acquisition to delivering real value that keeps subscribers around. We talk about the evolution of cancellation strategies (spoiler: it’s not the end of the road), what personal...
We explore how top brands are shifting their focus from acquisition to delivering real value that keeps subscribers around. We talk about the evolution of cancellation strategies (spoiler: it’s not the end of the road), what personal...
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July 8, 2025 • 17 mins
Most brands overlook frequency. That’s a huge mistake.
In this episode of Subscription Prescription, I’m breaking down the unsexy—but massively important—topic of subscription frequency. We cover how to align deliveries with consumption, how to handle products with variable usage (like protein or pet food), and why sometimes a subscription isn’t even the best model at all.
You’ll learn:
How to choose the right frequency based on produ...
In this episode of Subscription Prescription, I’m breaking down the unsexy—but massively important—topic of subscription frequency. We cover how to align deliveries with consumption, how to handle products with variable usage (like protein or pet food), and why sometimes a subscription isn’t even the best model at all.
You’ll learn:
How to choose the right frequency based on produ...
Mark as Played
July 1, 2025 • 32 mins
Most brands treat subscriptions like a checkout option. The ones that win treat it like a lifestyle.
In this episode, I sit down with Cameron Gawley—fractional CMO, venture studio founder, and DTC veteran—to talk about the strategy behind building truly sticky subscriptions. We break down why most churn is caused by bad acquisition, how trial-size offers unlock long-term customers, and why retention really comes down to belonging. I...
In this episode, I sit down with Cameron Gawley—fractional CMO, venture studio founder, and DTC veteran—to talk about the strategy behind building truly sticky subscriptions. We break down why most churn is caused by bad acquisition, how trial-size offers unlock long-term customers, and why retention really comes down to belonging. I...
Mark as Played
June 24, 2025 • 17 mins
I hit the floor at SubSummit to ask the smartest operators in the subscription space one question:
What tactic is underleveraged—or completely overlooked—by brands today?
In this episode, you’ll hear rapid-fire answers from founders, retention pros, and tech leaders who are deep in the day-to-day of subscription.
We cover everything from:
What tactic is underleveraged—or completely overlooked—by brands today?
In this episode, you’ll hear rapid-fire answers from founders, retention pros, and tech leaders who are deep in the day-to-day of subscription.
We cover everything from:
- Fixing failed payments and churn spikes
- Boosting retention with loyalty and billing reminders
- Th...
Mark as Played
June 17, 2025 • 25 mins
Subscriber retention has a soft side… and a sharp edge.
In this episode, I talk with Lydia Farmer from DIME Beauty about how they’ve built a retention machine that balances emotional loyalty with operational precision.
We cover:
– The retention levers DIME actually uses (and skips)
– Why retention isn’t just CX—it’s brand, ops, marketing, and more
– How DIME turns one-time beauty buyers into long-term subscribers
– Lessons learned scali...
In this episode, I talk with Lydia Farmer from DIME Beauty about how they’ve built a retention machine that balances emotional loyalty with operational precision.
We cover:
– The retention levers DIME actually uses (and skips)
– Why retention isn’t just CX—it’s brand, ops, marketing, and more
– How DIME turns one-time beauty buyers into long-term subscribers
– Lessons learned scali...
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