Subscription Prescription | Weekly Doses to Boost Ecommerce Revenue

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

Stop Obsessing Over Email: The Real Levers for Subscription Retention

May 5, 2026 • 33 mins
Josh Tay has spent years in retention at Common Thread Co., No Limit Email, and now as VP of Strategy at Chronos Agency — and his take on email might surprise you. What we cover:
  • Why email is a secondary channel, not the starting point for subscription growth
  • The three real levers that move the needle: front-end offers, retention, and upsells
  • How to think about causation vs. correlation when brands see churn spikes from email
  • Why L...
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How AI Search Actually Works, and What Subscription Brands Need to Do Now

April 21, 2026 • 18 mins
AI is changing how customers find products — and most subscription brands aren't ready for it. In this episode, I break down how AI search actually works and what simple steps you can take right now to make sure your brand shows up. What we cover:
  • Why AI search is different from traditional personalization (and why that matters)
  • How AI uses context to surface products — and what that means for your website
  • Why conflicting informat...
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Why Your Dunning Strategy Is Sending Customers to the Wrong Door

April 14, 2026 • 17 mins
Most subscription brands are losing revenue to failed payments - not because customers don't want to pay, but because they're being sent to the wrong place to fix it. In this episode, I break down how payment processing actually works, what your processor health score means, and how to build a dunning strategy that actually recovers payments.

What we cover:
  • How tokenization and payment processing work in subscription commerce
  • Why ...
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Amazon vs. Your Shopify Store: How to Win the Subscription Customer

April 7, 2026 • 11 mins
Amazon has real advantages - trust, convenience, price, and discoverability. But that doesn't mean your Shopify store can't win. In this episode, I break down exactly why Amazon pulls subscribers away from DTC brands and what you can do to fight back. What we cover:
  • The 4 reasons customers choose Amazon over your site
  • Why discounting alone won't beat them
  • How to build an offer that's impossible to replicate on Amazon
  • Tools that bri...
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Agentic Commerce: How AI Will Discover (Or Miss) Your Subscription

March 31, 2026 • 38 mins
AI is changing how people discover products online. And if your subscription offer isn't structured correctly, AI agents will skip right past it.

In this episode, I sit down with my business partner David Bradley (and the founder of QPilot, Autoship Cloud, and Nextime) to break down how agentic commerce actually works, why subscription products need to be optimized differently than one-time purchases, and what brands can do right no...
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The Post-Purchase Communication Gap Killing Your Subscriptions

March 24, 2026 • 12 mins
Most subscription brands invest heavily in getting the first order. Then they go silent. That gap between purchase and second shipment is where you lose subscribers, and most brands don't even realize it's happening. In this episode, I break down why post-purchase communication is the most overlooked lever in subscription retention and what to do about it.

What we cover:
• Why the window between order 1 and order 2 is the highest-ris...
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Why Lowering Your Price Won't Fix Subscription Churn

March 17, 2026 • 34 mins
SpaceGoods does 80% of their business on subscription and their #1 churn reason is cost. So they tested making the subscription 25% cheaper. It didn't move the needle at all.

In this episode, I sit down with Bea Le Coultre, Retention & CRM Manager at SpaceGoods, to talk about what actually drives subscription retention. We cover how they coach customers through their first two weeks, why matching the right product to the right b...
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The Email Strategy Most Subscription Brands Get Backwards

March 10, 2026 • 15 mins
Most email agencies spread out your subscriber onboarding emails to avoid "over-sending." I think that's backwards. In this episode, I break down the email and SMS strategy that actually drives retention for subscription brands.

What we cover:
• Why you should send more emails in the first few days, not fewer
• The onboarding window most brands completely waste
• How to turn your billing reminder into a retention tool
• Why SMS reduces ...
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Education, Winbacks, and Direct Mail: Dirtea's Retention Strategy

March 3, 2026 • 35 mins
Jade Moffett from Dirtea joins the show to break down how they use education-first onboarding, segmented winback flows, and direct mail to retain and re-engage subscribers. We dig into why they wait to cross-sell, how their CX team shapes retention messaging, and the 200% lift they saw from Paper Run.

What we cover:

• Why education-first onboarding drives long-term retention
• Segmenting winback flows by cancellation reason and produc...
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Three Psychological Triggers That Keep Subscribers From Cancelling

February 24, 2026 • 14 mins
In this episode, I break down the three psychological triggers that keep subscribers from hitting the cancel button, and how you can use them to reduce churn.

What we cover:

• How reducing friction and anxiety prevents cancellation impulses
• Why identity reinforcement makes subscribers feel like they belong
• The role of habit formation in building long-term commitment
• Practical ways to apply these triggers in your subscription busin...
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From Trial to Subscription: What Works (And What Doesn't) - A Conversation with Jose Vigo

February 16, 2026 • 28 mins
Free trials are everywhere in DTC, but most brands struggle with what matters most: turning trials into full-price buyers and subscribers. In this episode of Subscription Prescription, I’m joined by Jose Vigo, founder of Healthy Metal, a magnesium sleep brand built around sachets and a “try it first” acquisition strategy.

We unpack how a shipping-only trial can work, what drives conversion after the sample arrives, and the practical...
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The First Subscription Fixes I’d Make If I Only Had a Few Days

February 10, 2026 • 11 mins
If I only had a couple of days to improve a subscription program, this is exactly where I would start.

In this episode of Subscription Prescription, I walk through a mini subscription workshop focused on fast, high-impact fixes. These are practical changes you can make quickly to increase subscription opt-in, reduce churn, and improve retention without rebuilding your entire stack. We cover:
  • Why defaulting to subscribe and save m...
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Subscription Claims, Compliance, and Where Brands Get Burned - An Interview with Natascia Taken

February 3, 2026 • 31 mins
Claims are one of the fastest ways subscription brands grow and one of the fastest ways they get into trouble.

In this episode of Subscription Prescription, Natascia Taken walks us through the do's and don'ts of claims.

We talk about the legal reality behind the claims brands make across product pages, ads, emails, testimonials, and influencer content. This is an area most founders and operators think about too late, usually after co...
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The Fastest Way to Grow Subscriptions Isn’t Retention (Here’s Why)

January 27, 2026 • 8 mins
In this episode of Subscription Prescription, I break down a question that comes up constantly when auditing subscription brands. Most teams instinctively focus on retention, trying to squeeze incremental gains out of month-to-month renewal rates. But what if the biggest lever is actually before the first order ever happens?

Using a simple, real-world math example, I walk through:
  • Why cutting churn in half is often harder than it...
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How Wellbell Got to 87% Subscription (Offer, Education, and Retention Playbook)

January 20, 2026 • 46 mins
In this episode of Subscription Prescription, I’m joined by Hattie Gilpin, Director of Operations at Wellbel (a hair, skin, and nail supplement brand that’s ~87% subscription) and a founder of HAM, a new analytics platform built for subscription operators.

We dig into the real problems subscription brands face when their data is split across tools (or disappears after platform migrations), and how operators can get clarity without s...
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How to Use Discounts, Gifts, and Promotions Without Killing Your LTV

January 13, 2026 • 16 mins
In this solo episode of Subscription Prescription, I dig into one of the biggest headaches in DTC subscriptions: offer strategy. Should you run a discount, add a gift, or push a limited-time promotion? I break down the good, bad, and overlooked strategies behind each of these tools—and how they impact your conversion, margin, and long-term retention. We’ll cover:
  • When discounts work—and when they actually hurt your LTV
  • How to use...
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CRO for Subscription Brands: Fix Your Funnel and Boost Subscription Take Rate

January 6, 2026 • 35 mins
Most brands think CRO = button colors and checkout tweaks. It’s not.

In this episode of Subscription Prescription, I’m joined by Anthony Morgan (CEO & Founder of Enavi) to break down what real conversion rate optimization looks like for ecommerce subscription brands and where the biggest wins actually hide (hint: it’s usually not checkout).

We cover how growing brands diagnose funnel bottlenecks, why product discovery is breaking...
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Happy Holidays! Last Episode of the Year

December 9, 2025 • 2 mins
Wishing you and your team the best end to 2025 you can have. We're off until January. See you soon!

For more info, visit https://thesubscriptiondoc.com
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Subscription Armageddon: 4 Experts Break Down What’s Broken (And How to Fix It)

December 2, 2025 • 89 mins
In this special roundtable edition of Subscription Prescription, I sat down with three of the sharpest minds in the DTC subscription space:

👉 Bryan Starck – Founder of 100 Degree Celsius
👉 Jordan Narducci – Founder of DTCPG
👉 Andriy Rudnyk – Founder of Good Subscription Agency

Together, we unpacked what’s really broken in subscription software and strategy - and what is changing in 2026. 💥

Topics we cover:
  • Why your subscription o...
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Stop Forcing Subscriptions: What Actually Drives LTV

November 25, 2025 • 16 mins
Most brands think they have a subscription business. The truth is, most of them just have a product with a subscribe button. In this episode of Subscription Prescription, I break down the real reason subscriptions succeed or fail and what you should be evaluating before you decide to push a subscription-first model. We cover:
  • Why subscriptions are only one way to drive repeat revenue
  • How customer buying behavior determines whethe...
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