Howdy Partners,
If you thought last week was just another week on the internet, you weren’t paying attention. The frontier is shifting fast. We’re talking about ChatGPT becoming the most valuable ad placement on earth, TikTok trying to become your landlord (and your logistics manager), and why getting into Costco might actually be the worst business decision you ever make.
We had industry titans like Kyle Hency (Chubbies) and Dave Stickland (Popsmith) dropping truth bombs that hurt feelings but save bank accounts.
Saddle up. Here’s the run of show.
🤠 THE BIG SHIFT: AI IS THE NEW SHELF SPACE
The biggest news this week wasn’t a new feature - it was a fundamental change in how people buy.
1. ChatGPT Ads Cometh If ChatGPT tells someone what to buy, that isn’t just an ad - it’s a recommendation inside a high-trust environment.
The Hook: People don’t search in ChatGPT; they ask. Asking implies trust.
The Reality: Brands won’t compete on keywords anymore. They will compete on being the "answer."
The Kicker: Rumors are swirling that ChatGPT wants a % of the transaction. This isn't an ad tax; it's a distribution toll.
2. "Merit-Based" Shopping Harley Finkelstein (Shopify) dropped a hammer: Agentic Commerce (AI shopping for you) creates merit-based results.
The AI agent doesn’t care who paid the most for the banner ad. It cares about what fits the user’s specific request.
Implication: Niche brands with distinct identities win. Generic "drop-ship" vibes die.
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🎙️ GUEST HIGHLIGHTS: PROFIT OVER VANITY
We had some legends on the show this week. If you missed the livestreams, here is the alpha:
Kyle Hency (Co-Founder, Chubbies / GoodDay)
On Authenticity: "To reach your niche, you don’t market to them - you are them." Chubbies worked because it felt like locker-room energy, not a boardroom strategy.
On Viral Growth: It’s a blessing that breaks companies. If you can't operate at 3x demand, going viral is a liability, not a win.
Dave Stickland (Popsmith)
The "Costco" Trap: Dave admitted that getting Popsmith into Costco was his "most colossal blunder of 2025."
Why? It sounded like winning. It got applause on LinkedIn. But it was a massive distraction and capital drain.
The Lesson: "Likes don’t clear the P&L." Omni-channel too early is a tax on your momentum.
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⚔️ PLATFORM WARS: TIKTOK VS. THE WORLD
TikTok is Daddy (Literally) TikTok launched "Fulfilled by TikTok" (FBT). They are moving with Amazon energy.
The Play: Discovery -> Checkout -> Delivery. All owned by ByteDance.
The Risk: Once a platform owns your fulfillment, they own the rules. You trade margin and independence for distribution.
The "Halo Effect" is Real TikTok released tools to track off-site performance. They finally admitted the quiet part out loud: The sale doesn't always happen on the app. This is their bid for enterprise ad dollars.
Amazon Supercenters? Bezos is coming for the Waltons. Amazon is looking into big-box physical retail. If they crack this, the loop is closed.
🐴 QUICK HITS & CRAZY THINGS
Dr. Pepper Wins the Internet: They took a viral TikTok jingle ("Dr. Pepper, baby, it's good and nice") and put it on national TV during the CFB Championship. Lesson: Don't manufacture virality; capitalize on it.
Buzzballs put a ring on it: They made a $35k engagement ring. Why? Because absurdity drives attention. Earned media > Paid media.
Gen-Alpha is Unplugging: The most online generation is being forced offline by parents. "Dumb phones" and analog toys are surging. If your brand relies on constant screen stimulation, watch out.
Raw vs. Craft: Mosseri says "raw" content is winning. We disagree. AI can fake "raw" now. True Craft - the thinking before you hit record - is the new moat.
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🤠 THE FINAL RIDE
This week taught us one thing: The gap between "activity" and "leverage" is widening.
You can be busy chasing Costco deals, arguing on Twitter, or trying to trick the algorithm. Or, you can focus on merit, craft, and profit.
Don't get distracted by the shiny objects. Focus on the systems that pay you.
See you at high noon.
- The Ecomm Cowboy Team