Podcast Summary: Marketing Operators

Episode: 88 – Rethinking the Customer Journey: Text-to-Buy, Post-Purchase Wins & Alternative Media
Hosts: Connor McDonald, Cody Plofker, Ben
Date: December 2, 2025

Overview

This episode dives deep into innovations in the customer journey for eCommerce and DTC brands. The hosts unpack the latest on text-to-buy flows, post-purchase optimization, and the emergence of alternative media buying strategies—from functional SMS experiences to creative out-of-home activations. The conversation is lively, blending tactical marketing insights with industry anecdotes and the latest Internet culture memes, all aimed at helping brands adapt and thrive in a changing landscape.

Key Topics & Insights

1. Rethinking Promotions and Bundles in DTC (01:33–08:29)

• Promo Fatigue & Strategic Restraint
  • Cody shares his brand’s experience holding off on “always-on” discounts and only recently running their first sitewide sale.
  • The hosts agree that regular discounting, while easy for short-term revenue, can train customers and degrade long-term value.
  • “It is much easier to become complacent when you’re just running promos.” — Connor McDonald (04:36)
• Bundles & Newness as Growth Levers
  • Seasonal bundles, exclusive kits, and limited-edition drops have been key for Q4 and Black Friday; ultimately, newness, not just discounts, drives urgency and volume.
  • As certain bundles have matured, there’s a need to anticipate when a hit product’s momentum will fade and plan pivots before that happens.

2. The “May I Meet You” Meme & X Monetization (08:29–15:41)

• Bill Ackman’s Viral Dating Advice (08:52–12:06)
  • Cody narrates the now-viral “may I meet you?” phrase from Bill Ackman as a meme, and the hosts discuss how Internet culture amplifies such moments.
  • “It’s just like the worst line, but the funniest line ever.” — Cody (11:18)
• NBA Sentel & Parody-Driven Virality (12:21–14:42)
  • Explaining how parody accounts like NBA Sentel both predict and shape sports narratives.
• How Monetization Works on X/Twitter (14:42–15:41)
  • Discussing CPM, impressions, and how parody and meme accounts capitalize through X’s monetization model.

3. Cutting-Edge Commerce: Text-to-Buy, Post-Purchase Experiences & Cross-Brand Fulfillment (17:50–33:11)

Text-to-Buy & Seamless Repeat Purchases (17:50–24:48)

• Fellow’s Experience as a Case Study

  • Ben recounts a smooth text-to-buy flow with Fellow, where a single SMS interaction lets him reorder coffee, suggesting huge potential for consumable brands.
  • “I was like so jazzed on the experience. I just thought it was super seamless.” — Ben (17:51)

• Platform Dynamics

  • OneText and custom SMS flows are emerging, with Shopify’s level of support fluctuating over time.
  • “It’s inevitable that we see more of this.” — Connor McDonald (22:42)
  • Conversational commerce and AI integrations (like Shopify + ChatGPT) are shaping the direction.

• Applications Across Brands

  • Not limited to food or CPG; even t-shirts or accessories that need regular replenishment could benefit from SMS-driven reordering.
  • Example: Brands like Bottomless using smart scales for dynamic subscription timing.

Cross-Brand Fulfillment, Shopify Collective, & Post-Purchase Upsells

• Shopify Collective & AfterSell’s New Features (24:48–27:21)

  • Cody discusses leveraging Shopify Collective for partnership-based, cross-brand fulfillment—selling complementary products fulfilled by partners, not requiring inventory hold.
  • AfterSell beta’s post-purchase cross-brand upsell (affiliate dropshipping model) discussed as a next horizon.

• Operational Innovations—Order Delays for Upsell

  • “Double dash” method modeled after food delivery apps: delaying order fulfillment to allow post-purchase upselling and basket-building.

• Key Quote:

  • “We’re talking about seamlessness of checkout... and then there’s also a future where you’re merging both of those.” — Connor McDonald (27:21, 27:47)

Smarter Subscriptions and the Limits of “Always-On” Funnels

• Flexibility with subscriptions and order flows (e.g., text reminders and easy skips) improve LTV, even if short-term AOV takes a hit.
• Segmenting dormant leads for specific down-sells (sample packs, try-before-you-buy) can recapture value without risky CAC.

4. Alternative Media: Sophisticated CPM Arbitrage & Content as a Growth Lever (45:59–66:34)

Media Expansion Beyond Meta (45:59–48:36)

• Ben expresses bullishness on expanding into new media—especially out-of-home, niche programmatic buys (e.g., airport-only NFL games), and email newsletters.
• Growing awareness that solely focusing on Meta leaves scale on the table.

Organic Social & “Street Interview” Content (48:36–55:22)

• Cody: Biggest push for 2026 is mastering organic, short-form content—especially authentic, man-on-the-street style.
• They cite Josh Suggs, a TikTok/short video creator, as inspiration. Street interviews drive both UGC and engaging ads.
• “I think everybody should have street interviews… you just need good ones that are authentic.” — Cody (54:44)

Out-Of-Home & Experiential (50:53–53:20)

• Out-of-home (billboards, trucks, events) has proven incrementality and, compared to digital, low minimums for experimentation.

Media Budgeting & Attention Arbitrage (58:10–69:17)

• Diverging models between “everywhere presence” (Manscaped) and ultra-focus (Brooklinen).

• Large TAM brands should reserve budget for both performance-measured buys and probabilistic, impression-arbitrage opportunities.

• Quote:

  • “We just need to say, hey, we’re comfy spending this much on these channels this year. As long as the CPMs are good, we’re happy with it.” — Ben (62:19)

The Rise and Fall of Channels

• Newsletters: Saturate quickly, decline in efficiency; not scalable as they once were.
• YouTube influencer: Once a core channel, now streamlined and less of a focus.
• “I think there was a newsletter bubble.” — Cody (69:42)

5. Operational Wisdom & Channel Planning (71:29–74:07)

• Connor McDonald shares a “channel expansion checklist” for brands evaluating new platforms—consider the business’s maturity, the product category, and the channel’s alignment.
• Channel strategies should be tailored per product line; what works for wallets may not work for power banks or rings.

Notable Quotes with Timestamps

• On promo dependency:
  “It is much easier to become complacent when you’re just running promos...” — Connor McDonald (04:36)

• On meme virality:
  “It’s just like the worst line, but the funniest line ever.” — Cody (11:18)

• On text-to-buy:
  “I was like so jazzed on the experience. I just thought it was super seamless.” — Ben (17:51)

• On the future of checkout:
  “We’re talking about seamlessness of checkout... and then there’s also a future where you’re merging both of those.” — Connor McDonald (27:21, 27:47)

• On the changing role of newsletters:
  “I think there was a newsletter bubble.” — Cody (69:42) “We were saturating these channels. We spent a million dollars there. And then performance, naturally just declined over time...” — Connor McDonald (70:33)

Timestamps for Important Segments

• 01:33 — Strategies for holiday promotions, bundles, and their limits
• 08:52 — The “May I Meet You?” meme, Bill Ackman, and virality
• 15:57 — Discussion of creative diversity and AI, with a plug for Motion’s AI tagging
• 17:50 — In-depth breakdown of text-to-buy commerce, platform trends, and SMS LTV strategies
• 24:48 — Shopify Collective, AfterSell’s cross-brand post-purchase innovation
• 27:21 — Defining “seamless checkout” and merging it with cross-brand fulfillment
• 32:05 — Re-imagining subscriptions, sample packs, and downselling in retention
• 45:59 — Alternative media expansion: CPM arbitrage, out-of-home, CTV, newsletter/cross-channel planning
• 53:37 — Street interviews as a core content pillar for brand engagement
• 58:10 — Budgeting for CPM arbitrage vs. measurable channels
• 71:29 — How Ridge approaches channel planning per business line

Memorable Moments

• The “May I Meet You?” meme breaks down how Internet virality shapes brand conversations and behavior (08:52–12:06).
• Street interviews and man-on-the-street content are highlighted as the next must-have for social media-driven brands (53:37–54:44).
• Insightful breakdown of the life cycle of media channels—from newsletters to YouTube to out-of-home—and how to decide where to double down in 2026.

Key Takeaways

• For DTC brands, balancing newness, not just discounts, is essential for sustainable growth, especially in Q4.
• Text-to-buy and frictionless post-purchase flows are gaining ground, especially for consumables and repeat-purchase goods.
• Cross-brand fulfillment (Shopify Collective, AfterSell’s new features) opens fresh post-purchase and upsell opportunities.
• Media diversification—especially toward organic social content and creative out-of-home—is a critical next step for brands plateauing on Meta and other core platforms.
• Awareness campaigns and CPM arbitrage should be balanced with performance-driven media; not everything can or should be ruthlessly tracked.
• Channels rise, saturate, and fall (newsletters, YouTube influencer, etc.); constantly reassess by product line and market maturity.

For listeners: Whether you’re a growth marketer, DTC founder, or creative strategist, this episode is a playbook for reimagining your customer journey—making it frictionless, more profitable, and ever-evolving with the changing media landscape.