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Ecomm Cowboy

Ecomm Cowboy

DTC’s daily show. Live weekdays 12pm (CST)—what’s now/next in ecommerce so marketers can survive and thrive.

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Shopify Editions Winter '26 Is Art

Dec 18, 2025

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2 min read

Shopify Editions Winter '26 Is Art

Sidekick’s “vibe-coded” theme edits, AI rollout testing, agentic commerce, corn milk, and why the internet needs to stop panicking about robot-made commercials.

Chris Hall
Colin Dougherty
Chris Hall, +1
Black Friday/Cyber Monday 2025 Recap | Chris x Colin

Dec 5, 2025

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4 min read

Black Friday/Cyber Monday 2025 Recap | Chris x Colin

An Honest Review: BNPL Hangover, Shopify Love Letter, and AI-powered Creative

Chris Hall
Colin Dougherty
Chris Hall, +1
AI Layoffs, Cheap Money & Live Selling | Chris x Colin

Dec 4, 2025

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2 min read

AI Layoffs, Cheap Money & Live Selling | Chris x Colin

How the New Economy is Reshaping Ecommerce

Chris Hall
Colin Dougherty
Chris Hall, +1

Articles

Build It, Own It, Exit It: The New DTC Game

Apr 13, 2026

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15 min read

Build It, Own It, Exit It: The New DTC Game

Strap in! Commerce just hit another gear and is shifting from chasing growth to engineering systems that capture, convert, and sustain attention. Brands are no longer winning through ads alone they’re combining cultural moments, creator-led distribution, and high-velocity creative with strong backend systems like retention, community, and seamless checkout. At the same time, platforms, AI, and acquisitions are reshaping control forcing operators to think beyond campaigns and build assets that can scale, adapt, and even exit. The gap is widening fast: those still relying on old playbooks are getting left behind, while those who understand attention, ownership, and execution are pulling ahead.

Ecomm Cowboys
Ecomm Cowboys
Ecommerce in 2026: Where AI, Content, and Profit Collide

Apr 6, 2026

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15 min read

Ecommerce in 2026: Where AI, Content, and Profit Collide

A clear shift in ecommerce emerges: the old playbook is breaking down, and a new one is being written in real time. From the death of safe, polished marketing to the rise of AI-powered operations, creative velocity, and platform diversification, success now depends on adaptability and execution. Brands are facing tighter margins, increasing platform risk, and more competition, forcing operators to focus on profitability, retention, and owned distribution. At the same time, new opportunities are emerging from premium niche products and resale markets to AI-driven content and alternative acquisition channels. The common thread: winning in 2026 isn’t about doing more it’s about doing the right things faster, smarter, and with stronger systems behind them.

Ecomm Cowboys
Ecomm Cowboys
Automation Is Eating Ecommerce So Brands Have to Build Moats, Not Tactics.

Mar 31, 2026

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12 min read

Automation Is Eating Ecommerce So Brands Have to Build Moats, Not Tactics.

The signal is consistent: platforms and AI are collapsing the old playbook where you could out-execute with better media buying, faster edits, or channel hacks. Content creation is getting cheaper and faster (AI-native virality, CapCut), conversion is moving inside platforms (YouTube creator matching, Stripe x Facebook checkout), speed is becoming table stakes (Amazon 1-hour, FedEx 2-hour), and ad optimization is shifting away from clean ROAS narratives toward broader acquisition systems (Meta changes, TRIBE V2). In that world, the winners aren’t the brands with the slickest tactics they’re the ones building compounding engines: retention and membership (Pop Mart), differentiated product truth (A2 dairy, wellness), smarter distribution (TikTok Shop, retail moves), and real operational infrastructure (telehealth, hardware). Net: ecommerce is becoming more automated and more competitive, so the only durable edge is creative taste, customer ownership, and systems that keep working when platform rules change.

Ecomm Cowboys
Ecomm Cowboys
Attention > Everything | The New Rules of Ecommerce

Mar 23, 2026

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14 min read

Attention > Everything | The New Rules of Ecommerce

Across this week’s episodes, one theme is undeniable: ecommerce is no longer about who can spend the most it’s about who can capture and convert attention the best. As platforms become less reliable, AI floods the market with content, and large incumbents move into DTC channels, the advantage shifts to brands that are fast, creative, and diversified. From viral brand moments and bold ad strategies to the rise of owned channels like SMS and the evolution of retail into media, the landscape is being rewritten in real time. The operators who win won’t just follow playbooks they’ll create them.

Ecomm Cowboys
Ecomm Cowboys
AI, Ecommerce, and the New Operator Playbook

Mar 16, 2026

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13 min read

AI, Ecommerce, and the New Operator Playbook

The biggest shifts happening across AI, ecommerce, marketing, and consumer brands. Across five episodes, we explore everything from platform risk and AI infrastructure to viral marketing, social commerce, and the changing ecommerce job market. Along the way, founders, operators, and industry experts share what they’re seeing on the ground — from the rise of retention‐driven growth and live shopping to AI reshaping software, marketing teams, and online fraud. If you’re building, operating, or investing in ecommerce, these conversations highlight the strategies, technologies, and trends shaping the next era of digital commerce.

Ecomm Cowboys
Ecomm Cowboys
The Next Era of Ecommerce: AI, Platforms, and Operator Leverage

Mar 10, 2026

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10 min read

The Next Era of Ecommerce: AI, Platforms, and Operator Leverage

Gear up. Over the past five episodes we unpacked AI transforming how marketing teams operate, TikTok Shop rewriting the ecommerce playbook, and Amazon brands expanding to Shopify to own their customers. We broke down Apple’s move into low‐cost laptops, Nike’s $300M brand reset, Meta’s evolving ad ecosystem, and why agencies are rethinking their margins in the age of AI. Along the way we explored meme marketing, livestream commerce, new acquisition trends, and the operators building smarter systems with tools like Claude. Consider this your five‐episode download on the ideas, strategies, and shifts shaping modern ecommerce.

Ecomm Cowboys
Ecomm Cowboys
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