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Dive into a collection of past posts and rediscover timeless content.
"The largest private acquisition in our space"

May 21, 2026

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2 min read

"The largest private acquisition in our space"

Oisin O'Connor (CEO, Recharge) & Aidan Thibodeaux (CEO, Skio) join us live!

Colin Dougherty
Colin Dougherty
Google I/O Domination

May 20, 2026

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2 min read

Google I/O Domination

Plus, Zuck's leaked internal audio and "lower-value human capital"

Colin Dougherty
Colin Dougherty
The DTC M&A Engine Just Restarted: Skio Sells for $105M, China Blocks Manus, Meta Drops AI Connectors

May 5, 2026

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10 min read

The DTC M&A Engine Just Restarted: Skio Sells for $105M, China Blocks Manus, Meta Drops AI Connectors

The week DTC stopped pretending. Subscription got acquired ($105M for Skio). The biggest cross-border AI deal of the year just got blocked at the border (Manus). Meta dropped AI Connectors and the operator timeline split into two camps overnight. The 3PL civil war went public. TikTok Shop is now projected to be 10% of US retail by 2028. And Nike just took the loudest L in performance footwear in 30 years. Five episodes, ten guests, and the playbook updates that actually matter heading into Q3, all in one place.

Ecomm Cowboys
Ecomm Cowboys
The New Playbook for Winning in DTC Has Arrived

Apr 27, 2026

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7 min read

The New Playbook for Winning in DTC Has Arrived

eCommerce is evolving fast, and the brands that win next will be the ones that adapt faster than the market changes. From Commerce Roundtable insights with elite operators to daily breakdowns on AI, Meta volatility, TikTok Shop, resale, and creator-led growth, the conversations consistently pointed to the same truth old growth playbooks are expiring. Winning in 2026 requires diversified acquisition channels, sharper creative, stronger retention systems, leaner teams, and founders willing to stay visible and move boldly. Whether it was 9-figure operators sharing scaling lessons, solo founders building massive businesses, or marketers exposing what’s actually working right now, these five episodes mapped the modern path forward: stay useful, stay authentic, test relentlessly, and never let your brand become irrelevant.

Ecomm Cowboys
Ecomm Cowboys
AI Is Rewriting E-Commerce And Most Brands Are Already Behind

Apr 20, 2026

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8 min read

AI Is Rewriting E-Commerce And Most Brands Are Already Behind

Strap in! The old e-commerce playbook is breaking fast. AI is shifting from tools to full-on execution (and trillion-dollar opportunities), creative is becoming a speed game powered by automation, and platforms like TikTok are quietly reshaping where demand is built. At the same time, brands are realizing that measurement is imperfect, “best practices” are often traps, and real growth comes from bold pivots, community, and owning distribution. From Amazon cracks to AI wearables, from recommerce to content engines the operators winning right now aren’t following trends... they’re rebuilding their entire systems around what’s coming next.

Ecomm Cowboys
Ecomm Cowboys
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
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