Episodios

  • Why Your Dunning Strategy Is Sending Customers to the Wrong Door

    Why Your Dunning Strategy Is Sending Customers to the Wrong Door
    Apr 14 2026
    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 your processor health score matters (and what hurts it)
    • The math on why a 1% improvement in processing success is massive at scale
    • In-app vs. third-party tools for payment recovery (Fly Code, Redux, Butter Payments)
    • Why segmenting by payment method — credit card, Shop Pay, PayPal — is the key to better dunning
    • How to stop sending PayPal subscribers to the wrong update link
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    17 m
  • Amazon vs. Your Shopify Store: How to Win the Subscription Customer

    Amazon vs. Your Shopify Store: How to Win the Subscription Customer
    Apr 7 2026
    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 bring Amazon-level delivery transparency to your subscription experience
    • Why SMS is one of your most powerful retention tools
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    11 m
  • Agentic Commerce: How AI Will Discover (Or Miss) Your Subscription

    Agentic Commerce: How AI Will Discover (Or Miss) Your Subscription
    Mar 31 2026
    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 commerce
    • How AI agents shop on behalf of consumers (and what that means for your product pages)
    • The role of explainer pages, structured data, and catalog organization in AI discoverability
    • Why positive AND negative context both matter for getting found
    • What Chewy and PetSmart are doing right that most brands aren't
    • Simple steps any brand can take today to prep their subscription for AI search
    Guest: David Bradley LinkedIn: https://www.linkedin.com/in/davebrad/
    Website: https://autoship.cloud

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    39 m
  • The Post-Purchase Communication Gap Killing Your Subscriptions

    The Post-Purchase Communication Gap Killing Your Subscriptions
    Mar 24 2026
    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 do differently in the first 30 days
    • Why onboarding is a retention strategy, not just a customer experience nice-to-have

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    13 m
  • Why Lowering Your Price Won't Fix Subscription Churn

    Why Lowering Your Price Won't Fix Subscription Churn
    Mar 17 2026
    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 subscriptions (and how they built that)
    • How ads overpromising on benefits creates downstream churn
    • The "starter kit" strategy for converting first-time buyers into subscribers
    • Why the first two weeks are make-or-break for retention
    • How product usage coaching (time of day, preparation method) impacts reorder rates
    • Using post-purchase surveys to segment by pain point
    • Billing reminder testing with Zamo and Klaviyo
    • The price reduction experiment that proved discounts don't fix churn
    • How asking subscribers to set a 90-day goal boosted retention 20%+

    Guest: Beatrice Le Coultre
    LinkedIn: https://www.linkedin.com/in/beatricelecoultre/
    Website: https://spacegoods.com

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    35 m
  • The Email Strategy Most Subscription Brands Get Backwards

    The Email Strategy Most Subscription Brands Get Backwards
    Mar 10 2026
    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

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    15 m
  • Education, Winbacks, and Direct Mail: Dirtea's Retention Strategy

    Education, Winbacks, and Direct Mail: Dirtea's Retention Strategy
    Mar 3 2026
    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 touchpoint improve the customer experience
    • Balancing short-term revenue with long-term customer value
    • Letting your CX team sense-check retention messaging

    Guest: Jade Moffett
    Her LinkedIn: https://www.linkedin.com/in/jade-moffatt-42ba35199/
    Website: https://www.dirtea.com

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    36 m
  • Three Psychological Triggers That Keep Subscribers From Cancelling

    Three Psychological Triggers That Keep Subscribers From Cancelling
    Feb 24 2026
    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

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    15 m