Subscription Prescription | Weekly Doses to Boost Ecommerce Revenue

The show went quiet for the summer. It's back, and the next few months are already booked.

I spent the break traveling, running the event business, working with clients, and building new tools for the subscription community. In this episode I catch you up on where I've been, what I built, and who's coming on the show next.

What we cover:
- Why I stepped back for the summer and what I was building
- The new tools at thecancelpage.com: an AI chatbot, an offer library, an email library, and a subscription ceiling...

AI agents are becoming the place your next subscriber starts their search. So how do you get found, and recommended, when a shopper asks ChatGPT instead of Google? What's helpful for subscription brands and retention leaders right now?

In David Bradley's first episode as host, he sits down with three people who live this every day: Al (retention lead at Puro Air and one of our SubRx docs), Hamish Gunasekara (co-founder and CEO of Catalog, formerly Afterpay and Cash App Commerce), and Matt (co-founder of SubRx and longtime host of the show).

Inside this episode:
<...

Matt, David, Al, Hamish

Matt, David, Al, Hamish

Your subscription program isn't shrinking, but it isn't growing either. You're acquiring exactly as many subscribers as you're losing each month. That's the growth ceiling, and it's one of the most dangerous places a subscription brand can be.

In this episode, I break down why subscription programs hit this equilibrium point and which lever to pull first to break through it (hint: it's probably not churn).

What we cover:
- The three pillars of every subscription program: subscriber count, AOV, and renewals
- How to spot the growth ceiling using simple acquisition and churn...

Black Friday is months away - and that's exactly why you should be working on your subscription strategy right now. In this episode, I walk through the three things subscription brands should be doing this summer to set themselves up for their biggest sales period of the year.

What we cover:
Why blanket discounts box you into a corner during BFCMHow to mine your subscription data for high-LTV product combosUsing customer conversations to uncover what's working (and what isn't)How to build an offer testing flywheel before the fall rushWhat to look for in first and second...

Most subscription brands avoid SMS because they're afraid it'll remind people to cancel. That fear is costing them long-term LTV. In this episode, I break down why SMS is one of the most underused tools in the subscriber journey, and how to use it the right way. What we cover:
Why fear of SMS is really just loss aversion in disguiseHow SMS drives product adoption in the critical first monthUsing text to give subscribers control: skip, swap, pauseWhy SMS recipients show higher LTV even with an initial churn bumpTools worth testing: Attentive, Klaviyo, Blueream, Recharge Concierge, and SkioWhat to...

Most subscription brands are setting a ROAS target and calling it a strategy. Trevor Crump, co-founder of Bestie Media, breaks down why that's leaving serious growth on the table - and what to do instead. What we cover:
Why ROAS constraints strangle your Meta spend before you ever hit your ceilingHow to calculate what a subscriber is actually worth - and use that to make buying decisionsLead vs. lag metrics: what ad buyers track vs. what actually moves the businessThe cash flow math founders miss when modeling customer acquisitionWhy discount-based offers produce lower-value customers (and what to do instead...

Grüns just got acquired by Unilever - and there are real lessons here for every subscription brand paying attention. In this episode, I break down the three things Grüns did exceptionally well that set them up for an exit like this. What we cover:
How Grüns used a 3:1 LTV to CAC ratio to grow profitably at every stageWhy product obsession is still the most underrated retention strategyHow retail expansion and multi-channel brand building created the opportunity Unilever actually boughtSubscribe to our newsletter for weekly doses just like this one: https://newsletter.thesubscriptiondoc.com

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 growthThe three real levers that move the needle: front-end offers, retention, and upsellsHow to think about causation vs. correlation when brands see churn spikes from emailWhy LTV is really about acquisition capacity, not profit for profit's sakeHow siloed growth and retention teams hurt subscription performanceThe membership models non-consumable brands (jewelry, apparel) are using ri...

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 websiteWhy conflicting information across your site can cost you the saleThe subscribe and save explainer page every brand needs to build (or audit)How to make shipping and delivery info...

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 commerceWhy your processor health score matters (and what hurts it)The math on why a 1% improvement in processing success is massive at scaleIn-app vs. third-party tools for payment recovery...

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 siteWhy discounting alone won't beat themHow to build an offer that's impossible to replicate on AmazonTools that bring Amazon-level delivery transparency to your subscription experienceWhy SMS is one of your most powerful retention toolsSubscribe to our newsletter for weekly doses just like this one: https://newsletter.thesubscriptiondoc...

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 now to make sure AI recommends their subscription offer.

What we cover:
Why Google's new subscription data property is a major signal for the future of...

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-risk moment for churn
• The communication mistakes most brands make after checkout
• How to build a post-purchase flow that actually drives retention
• What top-performing subscription brands d...

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 buyer matters more than discounts, and the surprising experiment that boosted retention by 20%+ without changing the price.

What we cover:
• Why 80% of SpaceGoods revenue comes from su...

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 churn instead of causing it
• The campaign paradox: skipping billing reminders but blasting daily promos
• Building subscriber-specific offers and campaign strategies

Subscri...

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 product
• Using direct mail (Paper Run) to re-engage churned and opted-out customers
• Cross-sell timing: why waiting until after the first subscription cycle matters
• How feedback loops at every touc...

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 business

Subscribe to our newsletter for weekly doses just like this one: https://newsletter.thesubscriptiondoc.com

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 systems that bring customers back. We cover:
How Healthy Metal uses a shipping-only trial to acquire new customersWhat actually influences trial-to-full conversion (product experience, price, and expectations)The post-t...

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 matters and how small design changes drive uptakeHow to upsell subscriptions in the cart when customers choose one-time purchaseTurning billing reminder emails into value reminders instead of charge noticesWhat...

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 copy has already converted and risk has already piled up. We cover:

Why copying competitor claims is one of the biggest legal mistakes...

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 soundsHow small improvements to conversion rate and subscription opt-in can drive the same growth as major retention overhaulsThe tradeoffs between retention optimization and offer testingWhy acquisition and retention cannot...

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 staring at 50 reports.

Hattie also shares what’s helped Wellbel build a subscription-heavy business: education-first onboarding, community-driven insights, and an intentional retention strategy that actually matches how customers consum...

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 LTVHow to use gifts to drive value without overspendingSmarter ways to run promotions that don't trigger churnWhether you're planning your Q1 campaign or trying to optimize an evergreen flow, this episod...

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 your growth, the “inside funnel” metrics Anthony uses, and the simplest subscription unlock we see brands miss: communicating clear subscription value props directly in the buy box.

What...

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

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 opt-in rate might be hurting your LTVThe dirty secret behind second-order churnThe real reason subscription analytics suckHow to personalize cancel flows and retention messaging by subscriber journeyThe future of Subscripti...

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 revenueHow customer buying behavior determines whether subscriptions make senseThe hidden risk of subscription-only offersWhen high AOV upfront beats subscription LTVWhy bulk buying, usage patterns, and consumption cycles matter more than cadenceHow to test conversion, AOV, and...

In this episode of Subscription Prescription, I sat down with Alyssa Wallace, a retention expert who knows how to turn plain text emails and founder videos into real subscription revenue.

We talk about what actually moves the needle for subscription brands, including:


Why most welcome flows fail (and how to fix them)
The power of plain text emails and real founder messaging
What “on brand” is costing you if you’re under $100M
How simple video responses can double your cancellation save rates
Why most post-cancel flows are missing the mark — and what...

In this episode of Subscription Prescription, I sit down with Eric Roush, founder of New Standard Co. — one of the most data-driven retention agencies in ecommerce. We dig into why retention doesn’t start after the purchase, how acquisition and retention teams should be working together, and what most brands get wrong about onboarding, testing, and customer experience. You’ll learn:
Why your rebuild and churn rates are really a reflection of your acquisition messagingHow to simplify onboarding to reinforce product expectations and build trustWhat “testing for incrementality” actually means and how to do it rightWhy integrated marketing teams outperform...

In this episode of Subscription Prescription, I break down what the fastest-growing subscription brands are actually doing to scale — and it’s not what you might expect. We’ll cover:
Why first-order profitability matters more than LTV in the early stagesThe hidden churn risk of bulk orders and frequency misalignmentTactics like free shipping, post-purchase upsells, and offer testing that are driving serious growthWhether you're doing $5K or $500K a month, this episode is a must-listen if you're trying to grow smarter and faster.

👉 Want more actionable insights?

Subscribe to the newsletter: https://newsletter.thesubscriptiondoc.com

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 actually moves the needle
✔️ Why replenishment reminders and SMS are your hidden retention tools
✔️ How great inserts and unboxing experiences can drive advocacy

If you're ready to strengthen your subs...

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 subscription program, these fixes are simple, fast, and worth your attention.

📩 Want more insights like this in your inbox? Subscribe to the newsletter: h...

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 retention.

You’ll learn:

✅ Why most brands hire operators when what they really need is strategy
✅ How to fix generic mess...

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 include in your onboarding and billing reminder emails

Why discounted subscribers churn - and wh...

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:
Why you should stop testing “angles” and start testing behaviorsHow customer observation reveals the truth behind usage and churnAnd why retention depends more on prompts than productsIf you're trying to lower CAC or improve LTV, this is t...

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:



Why churn is often a symptom of a buyer education problemHow helpful beats clever when it comes to building trustAnd why your loyalty program should revolve around your most committed customers—your s...

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 customers through SMS content instead of sales pushes.

If you're building or optimizing a DTC subscription, this conversation is packed with actionable insights on:
When and why to shift from...

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 screens and A/B tests to smart segmentation and save actions, I walk through exactly what to focus on—platform by platform.

You’ll learn:

What Recharge’s AI cancellation insights can (a...