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 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...
Mark as Played
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...
Mark as Played
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...
Mark as Played
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...
Mark as Played
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
Mark as Played
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...
Mark as Played
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...
Mark as Played
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...
Mark as Played
June 10, 2025 • 19 mins
In this episode of Subscription Prescription, we're breaking down the tech stack we actually recommend for DTC subscription brands—no fluff, no affiliate links.
From Shopify vs. WooCommerce to subscription platforms like Recharge, Skio, Stay, and Loop, we're sharing what tools we use with clients, what features actually matter, and how to avoid the most common mistakes brands make when choosing tech.
Whether you’re re-evaluating your...
From Shopify vs. WooCommerce to subscription platforms like Recharge, Skio, Stay, and Loop, we're sharing what tools we use with clients, what features actually matter, and how to avoid the most common mistakes brands make when choosing tech.
Whether you’re re-evaluating your...
Mark as Played
June 3, 2025 • 30 mins
Joe Siegel has done retention for some of the biggest names in CPG—including MrBeast’s Feastables—and this week, he’s on the pod.
We brought him on to talk about what’s changing in retention, what still works, and what most brands get totally wrong.
Joe’s not just a pro—he’s building tools, advising brands, and helping shape the future of how subscription and ecom teams keep customers around.
You’ll want to take notes.
Learn more at ht...
We brought him on to talk about what’s changing in retention, what still works, and what most brands get totally wrong.
Joe’s not just a pro—he’s building tools, advising brands, and helping shape the future of how subscription and ecom teams keep customers around.
You’ll want to take notes.
Learn more at ht...
Mark as Played
May 27, 2025 • 20 mins
Understanding the financial metrics behind your subscription business is crucial for sustainable growth. In this episode of Subscription Prescription, we delve into the core numbers that drive profitability: Customer Acquisition Cost (CAC) and Customer Lifetime Value (LTV).
We'll explore:
How to accurately calculate CAC and LTV
The significance of the LTV:CAC ratio and what it reveals about your business health
Common pitfalls in inter...
We'll explore:
How to accurately calculate CAC and LTV
The significance of the LTV:CAC ratio and what it reveals about your business health
Common pitfalls in inter...
Mark as Played
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