Today we’re breaking down the biggest shifts shaping ecommerce, AI, and brand strategy and one of the most important signals comes from the recent Anthropic leak. What it revealed isn’t just incremental progress it’s a widening gap between companies that know how to leverage AI and those that don’t. The takeaway? Competitive advantage is no longer just about having access to tools it’s about how fast you can operationalize them across content, decision-making, and execution.

For ecommerce brands, this means the future isn’t just “use AI for ads” it’s building systems where AI compounds across your entire org. Content gets faster. Testing gets smarter. Teams get leaner. The brands that figure this out early won’t just win on efficiency they’ll outpace competitors entirely.

Quietly, a new role is becoming the backbone of high-performing ecommerce teams and most brands are still underestimating it. The rise of the “creative strategist” (or hybrid operator) is reshaping how companies think about growth. This isn’t your traditional media buyer or brand marketer it’s someone who understands creative, data, platforms, and consumer psychology all at once.

Why does this matter now? Because the game has changed. Platforms like Meta and TikTok reward iteration, not perfection. The bottleneck isn’t budget it’s ideas and execution. The brands scaling today are the ones building internal systems to generate, test, and ship creative constantly. And this role sits at the center of it all.

Brett Ender (Noble Origins)
Built from a personal health crisis, Brett’s approach to brand building is rooted in authenticity not trends. He emphasizes that in saturated categories like protein, trust and sourcing transparency are the real differentiators. His biggest edge? Pairing a strong product with a content engine that builds belief over time.

Sawyer Covington (General Context)
Sawyer breaks down the chaos in Meta attribution and makes it simple: creative is the only lever that consistently scales. He’s seeing winning brands deploy AI not as a shortcut, but as a system for producing and iterating content faster than ever. The takeaway volume + speed + iteration beats “perfect ads” every time.

Today we’re breaking down one of the most important shifts happening under the surface of ecommerce measurement is being completely rewritten. Ramp just dropped its latest rankings, and the signal is loud: Triple Whale is dominating adoption, Haus is moving upmarket fast, and Northbeam is starting to lose ground.

But this isn’t just a leaderboard update it’s a reflection of a deeper change. Brands are no longer looking for perfect attribution (because it doesn’t exist). They’re looking for directional truth + speed. The winners in this next phase aren’t the tools that promise accuracy they’re the ones that help operators make faster, better decisions with imperfect data.

One of the clearest lessons from this episode: you don’t scale by tweaking — you scale by changing the game. Tyler Simmons’ journey with Bucket Golf is the perfect example. After doing just $5K over three years, a single product pivot unlocked $12M+ in revenue.

That kind of jump doesn’t come from better ads or slightly improved conversion rates. It comes from finding the right product-market fit and leaning all the way in. Most brands spend too long optimizing something that isn’t working when the real move is stepping back and asking if the product itself needs to change.

Adam Kitain (Intelligems)
Adam’s big point: most brands aren’t running enough experiment and the ones they do run are too slow. AI is now enabling continuous A/B testing across pricing, offers, and UX, turning experimentation into a daily habit instead of a quarterly project. The brands that win will be the ones that treat their business like a live testing environment.

Tyler Simmons (Bucket Golf)
Tyler proves that growth can hinge on one bold decision. After years of minimal traction, a single pivot changed everything and he scaled aggressively once it clicked. His Shark Tank experience reinforces it: when the product hits, everything else (capital, distribution, momentum) follows fast.

Michael Brandt (Ketone-IQ)
Michael’s story is a masterclass in long-term conviction a decade of pivots, partnerships, and positioning to build an entirely new category. From landing a $6M DoD contract to bringing in high-profile partners like Steven Bartlett and Jon Jones, his focus is clear: build something durable, not trendy. Category creation is slower but far more defensible.

Other Key Topics This Episode

Guests: TJ Bongiorno (YAPPER, Outty), Jason Wong ( Paking Duck)

Today we’re breaking down one of the most under-the-radar but important moments in ecommerce right now: Amazon advertisers pulling back spend. The April 15 boycott isn’t just a protest it’s a signal. Brands are starting to question rising costs, diminishing returns, and how much control they actually have inside Amazon’s ecosystem.

For years, Amazon was the “must-win” channel. Now? Operators are realizing that over-reliance comes with risk. The bigger takeaway isn’t whether the boycott works it’s that brands are actively looking for leverage outside of Amazon. Owned channels, community, and alternative distribution (hello TikTok Shop) are no longer “nice to have” they’re becoming survival strategies.

AllBirds calling itself an AI company raised eyebrows but it highlights a deeper trend: AI is becoming part of brand identity, not just operations. This isn’t about slapping AI into a press release it’s about how companies position themselves in a world where technology is expected, not optional.

At the same time, we’re seeing a tension emerge. From Postscript’s ecommerce sitcom to Franky Shaw’s AI-generated ad, the question is no longer “can AI make content?” it’s should it? As creative gets easier to produce, authenticity becomes the differentiator. The brands that win won’t just use AI they’ll know when not to.

TJ Bongiorno (Outty)
TJ is betting on a category that doesn’t fully exist yet social, nootropic-based drinks for the alcohol-alternative wave. His focus isn’t just distribution, but building behavior: getting people to rethink what they drink in social settings. The key insight: owning a category early means educating the customer just as much as selling to them.

Jason Wong (Paking Duck)
Jason is building what most brands overlook packaging as a core growth lever. From navigating global manufacturing challenges to working with high-growth brands, his lens is clear: the most investable companies in 2026 are the ones that obsess over product experience end-to-end. Packaging isn’t a cost center it’s part of the brand moat.

Guests: Robby Little (SlideMVP) , Brayden Flack (Reseller), Ben Sharf (Platter)

Sequoia just dropped one of the boldest takes in AI so far: the next trillion-dollar companies won’t sell software — they’ll sell outcomes. That means AI agencies, not SaaS tools. Instead of selling dashboards or copilots, the winners will sell “done-for-you” work: ads created, books closed, content shipped.

For ecommerce operators, this changes the game. Competing on tools becomes a race to the bottom competing on outcomes compounds with every AI improvement. The takeaway: if you’re still thinking like a SaaS operator, you might be missing where the real margin expansion is headed. The future isn’t AI for X it’s AI-powered X businesses.

While everyone debates AI, the platforms are quietly reshaping behavior:

Instagram is blurring the line between ads and landing pages with in-app experiences.
YouTube is finally giving users control over Shorts.
Even podcasts are going agentic hitting Wall Street workflows.

These aren’t flashy announcements, but they point to a bigger shift: distribution is becoming more embedded, more native, and harder to interrupt. The brands that win won’t just create content they’ll adapt to how platforms want that content consumed.

Robby Little (SlideMVP)
Robby turned a simple “dad hack” into a real product used from youth leagues to the MLB. His edge? Leaning into domestic manufacturing and backing it with bold guarantees that remove risk for buyers. Niche + trust + product-market clarity = scale.

Brayden Flack (Recommerce)
Brayden is riding the recommerce wave and it’s bigger than most think. Resale isn’t just a side hustle anymore; it’s actively eating into new retail. Operators ignoring secondary markets are missing where value is being recaptured.

Ben Sharf (Platter)
Ben saw the Shopify ecosystem breaking under app bloat and built a solution to replace it. His shift from agency to SaaS shows where the puck is going: simplification + consolidation + AI at checkout. The real unlock isn’t more tools it’s fewer, better ones.

Guests: Alex Greifeld (No Best Practices), Phoenix Ha (Social Commerce)

Meta’s AI glasses just went mainstream literally hitting Fox Business and it’s a signal most operators are underestimating. If AI becomes ambient (always-on, always-listening), discovery shifts from screens to real life. No more search bars. No more scrolling. Just prompts, context, and intent.

For ecommerce, this could completely reshape the funnel. The brands that win won’t just optimize ads they’ll optimize presence. When discovery becomes conversational, your brand either shows up… or disappears entirely. This isn’t a gadget story it’s the early stages of a new distribution layer.

Adobe’s dominance is starting to crack not because creatives disappeared, but because workflows are changing faster than legacy tools can keep up. Between AI-generated assets, automated TikTok slideshows via Claude, and live video formats, the bottleneck is no longer production it’s ideas and iteration speed.

We’re entering a world where the best brands aren’t the most polished they’re the fastest to test. Creative is becoming a system, not a one-off deliverable. And if your team still treats content like a campaign instead of a pipeline, you’re already behind.

Phoenix Ha (Instant Hydration)
Phoenix is betting big on TikTok Shop not as a channel, but as the channel. Her take: most brands are still over-optimizing Meta while ignoring where the next wave of demand is actually forming. The unlock isn’t perfection it’s getting uncomfortable early.

Alex Greifeld (No Best Practices)
Alex is pushing back on the entire idea of “best practices” in DTC. What works for one brand often breaks another and blindly copying playbooks leads to stagnation. The real edge comes from understanding context, not templates.

Also Covered

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See you on the trail,

The Ecomm Cowboy Team