Ecomm Cowboy

Chris Hall x Colin Dougherty
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  • UPDATED WEEKLY

DTC's daily show — what's now/next in ecommerce so marketers can survive and thrive.

  1. 3H AGO

    Chubbies Launches Bikini Brand? | Ebay Buys Depop from Etsy | Rok Hladnik Joins (2.19.26)

    Resale is going mainstream. Meta ads are still a mystery. Amazon is killing robots. And Chubbies just launched a women’s swim brand the right way.Today we break down one of the most interesting brand expansions in DTC: Chubbies launching Cheekies, a standalone women’s swimwear brand built by an all‑women team. Is this how mature ecommerce brands should expand?Then we sit down with Rok Hladnik for a no-BS conversation about paid media in 2026:- Why Meta’s Audience Network might be hurting your account- The most common technical mistakes inside ad accounts- Why media buyers should think like treasury managers- How AI is changing agencies, creators, and capital allocationWe also cover:- eBay acquiring Depop for $1.2B and why “Thriftmas” could unlock resale as a gifting category- Chili’s Margarita of the Month Club and what restaurants can teach DTC about retention- Amazon halting its Blue Jay robotics project while doubling down on agentic AI- A viral $200K credit card arbitrage story and what it says about risk- Ollie’s $600M acquisition and the continued dominance of premium petIf you’re building, buying media, or thinking about the future of ecommerce — this episode is packed with operator-level insights.— — —Welcome to DTC's daily—what's now/next in ecommerce so founders, marketers, and operators can survive and thrive.Weekly newsletter: https://newsletter.ecommcowboy.com/Made possible by:Postscript - https://postscript.io/sms-benchmarks?utm_source=Ecomm+Cowboy+Show&utm_medium=Show&utm_campaign=Ad+Read&utm_id=Ecomm+CowboyAMP - ⁠https://postscript.io/sms-benchmarks?utm_source=Ecomm+Cowboy+Show&utm_medium=Show&utm_campaign=Ad+Read&utm_id=Ecomm+CowboySeguno - https://www.seguno.com/?utm_source=Ecomm+Cowboy+Show&utm_medium=Show&utm_campaign=Ad+Read&utm_id=Ecomm+CowboyFollow Ecomm Cowboy:https://x.com/ecommcowboyhttps://www.linkedin.com/company/ecommcowboyhttps://www.instagram.com/ecommcowboy/https://www.tiktok.com/@ecommcowboyhttps://open.spotify.com/show/0q1Pp0rW8j6cehXToNTeJchttps://podcasts.apple.com/us/podcast/ecomm-cowboy/id1761749693

    1h 11m

  2. 1D AGO

    Report: AI Makes Marketing Hard | TikTok Halts End of Seller Shipping | Chris Geiss Joins (2.18.26)

    AI isn’t replacing marketers, yet — but it is raising the bar.We break down the AdWeek report that says AI isn’t cutting jobs at scale… but it is compressing timelines, increasing expectations, and creating what some are calling “quality debt” in creative.Are marketers empowered — or just squeezed?Then we sit down with Chris Geiss, founder of Seguno, to talk about the evolution of ecommerce email, what AI (and Gmail summaries) mean for operators, and why building entirely inside Shopify might be the future of SaaS. We dive into:• How email marketing has evolved over the last decade• Whether open rates still matter• Why duct‑taped tech stacks are killing attribution• The rise of the “one‑man brand” and lean marketing teams• Canva integrations and reducing creative friction• Brands crushing retention right now• Is software doomed in the age of AI?We also cover:- TikTok Shop halting its plan to end independent seller shipping after backlash- Dick’s Sporting Goods building a creator “Varsity Team” ecosystem- Why brands should bring back the jingle- Bing launching AI visibility reporting (and what that means for SEO)- And the broader shift toward DTC models in unexpected industriesIf you’re building in ecommerce in 2026 — this is a must-watch.Subscribe for weekly operator-level breakdowns, founder interviews, and real conversations about where ecommerce is headed.— — —Welcome to DTC's daily—what's now/next in ecommerce so founders, marketers, and operators can survive and thrive.Weekly newsletter: https://newsletter.ecommcowboy.com/Made possible by:Postscript - https://postscript.io/sms-benchmarks?utm_source=Ecomm+Cowboy+Show&utm_medium=Show&utm_campaign=Ad+Read&utm_id=Ecomm+CowboyAMP - ⁠https://postscript.io/sms-benchmarks?utm_source=Ecomm+Cowboy+Show&utm_medium=Show&utm_campaign=Ad+Read&utm_id=Ecomm+CowboySeguno - https://www.seguno.com/?utm_source=Ecomm+Cowboy+Show&utm_medium=Show&utm_campaign=Ad+Read&utm_id=Ecomm+CowboyFollow Ecomm Cowboy:https://x.com/ecommcowboyhttps://www.linkedin.com/company/ecommcowboyhttps://www.instagram.com/ecommcowboy/https://www.tiktok.com/@ecommcowboyhttps://open.spotify.com/show/0q1Pp0rW8j6cehXToNTeJchttps://podcasts.apple.com/us/podcast/ecomm-cowboy/id1761749693

    1h 12m

  3. 2D AGO

    American Eagle's Creator Playbook | Gen Z: Boredom as Entertainment | Matthew Holman Joins (2.17.26)

    We’re breaking down one of the smartest retail creator strategies in the game, going deep on the subscription playbook with one of ecommerce’s most focused operators, and unpacking the cultural shifts shaping the next wave of brands.Here’s what we’re covering:• American Eagle’s Creator Program — what they’re doing differently to win Gen Z, and what DTC brands can steal immediately• Subscription mastery with Matthew Holman (Subscription Doc) — offers, retention psychology, post-purchase leverage, and the biggest mistakes brands keep making• The new luxury status symbol (hint: it’s not a watch)• Why Gen Z is gravitating toward “boring” content — and what that means for brand building• $200 in tools → $50K in revenue — real leverage or Twitter math?• Meta’s new patented AI tech and what it means for advertisersIf you care about ecommerce, subscriptions, media buying, cultural trends, or where AI is pushing the market next — this one’s for you.— — —Welcome to DTC's daily—what's now/next in ecommerce so founders, marketers, and operators can survive and thrive.Weekly newsletter: https://newsletter.ecommcowboy.com/Made possible by:Postscript - https://postscript.io/sms-benchmarks?utm_source=Ecomm+Cowboy+Show&utm_medium=Show&utm_campaign=Ad+Read&utm_id=Ecomm+CowboyAMP - ⁠https://postscript.io/sms-benchmarks?utm_source=Ecomm+Cowboy+Show&utm_medium=Show&utm_campaign=Ad+Read&utm_id=Ecomm+CowboySeguno - https://www.seguno.com/?utm_source=Ecomm+Cowboy+Show&utm_medium=Show&utm_campaign=Ad+Read&utm_id=Ecomm+CowboyFollow Ecomm Cowboy:https://x.com/ecommcowboyhttps://www.linkedin.com/company/ecommcowboyhttps://www.instagram.com/ecommcowboy/https://www.tiktok.com/@ecommcowboyhttps://open.spotify.com/show/0q1Pp0rW8j6cehXToNTeJchttps://podcasts.apple.com/us/podcast/ecomm-cowboy/id1761749693

    25 min

  4. 3D AGO

    The Great AppLovin Debate | Ad vs. Ad | Ray Li, CEO of Sene Joins (2.16.26)

    Today we’re talking custom menswear, founder scar tissue, influencer economics, AI chaos, and whether your ads are actually good — or just expensive.Ray Li, CEO of Sene, has built one of the most interesting menswear brands on the internet — starting with custom suits you can order online (yes, really) and expanding into what might be the perfect T‑shirt.We’re digging into:- How Sene made online custom clothing actually work (fit, sizing, returns — the hard stuff)- The war stories: showrooms, wholesale attempts, retail bets that didn’t pan out- Panic attacks, cash crunches, and what survival really looks like- Why the “perfect tee” is such a powerful category in menswear- How luxury brands and Michelin-star restaurants accidentally turned Sene into a uniform supplier- What Ray is bullish on heading into 2026If you care about building durable brands (not just running ads), this one’s for you.Weekend Roundup of News:- The AppLovin debate — cheat code or risky dependency?- AI hallucinating company data (and why that should scare you)- OpenAI talent moves, Anthropic stumbles, and Meta’s always-on agents- How marketing teams are now using AI tools like Claude Code- “Truman Show” brands and the rise of performative brand-building- The shift back to IRL brands and physical activationsIf you’re building in ecommerce, experimenting with AI, testing ads, or trying to survive retail and DTC in 2026 — this livestream is for you.Subscribe, drop your questions in the chat, and let’s get into it.— — —Welcome to DTC's daily—what's now/next in ecommerce so founders, marketers, and operators can survive and thrive.Weekly newsletter: https://newsletter.ecommcowboy.com/Made possible by:Postscript - https://postscript.io/sms-benchmarks?utm_source=Ecomm+Cowboy+Show&utm_medium=Show&utm_campaign=Ad+Read&utm_id=Ecomm+CowboyAMP - ⁠https://postscript.io/sms-benchmarks?utm_source=Ecomm+Cowboy+Show&utm_medium=Show&utm_campaign=Ad+Read&utm_id=Ecomm+CowboySeguno - https://www.seguno.com/?utm_source=Ecomm+Cowboy+Show&utm_medium=Show&utm_campaign=Ad+Read&utm_id=Ecomm+CowboyFollow Ecomm Cowboy:https://x.com/ecommcowboyhttps://www.linkedin.com/company/ecommcowboyhttps://www.instagram.com/ecommcowboy/https://www.tiktok.com/@ecommcowboyhttps://open.spotify.com/show/0q1Pp0rW8j6cehXToNTeJchttps://podcasts.apple.com/us/podcast/ecomm-cowboy/id1761749693

    1h 8m

  5. FEB 12

    New Status Symbol: Wasted Time | McDonald's Caviar | Johnny Hickey Joins (2.12.26)

    We kick things off with Johnny Hickey — former CMO of Perfectwhitetee, founder of Delfina, current CMO of Sunny Somewhere NY, and the force behind DTC Growth Summit. How does he make running an agency, launching brands, and hosting national events look effortless? We break down the systems, mindset, and strategy behind scaling women’s apparel, building community-first brands, and creating events that operators actually want to attend.Then we zoom out into culture.Is the new luxury… wasting time? We unpack the rise of “neo‑leisure,” conspicuous grinding, and whether effortless living has replaced hustle culture as the ultimate flex. From performative offlineness and viral “Brick” devices to the question of whether we’re enjoying life or performing it for algorithms, we explore what status really looks like now.We also cover:• McDonald’s McNugget Caviar and irony marketing• Founder-core authenticity vs absurdist brand plays• AI-generated shows and the future of content• DJ Khaled x Wegovy and the macro impact of GLP-1 drugs• OpenAI’s vision for fully automated media buying inside ChatGPT• What happens to agencies and performance marketers in an AI-led ad ecosystemThis episode is about autonomy — over your time, your brand, your marketing, and your attention.The real luxury in 2026 might not be money.It might be control.— — —Welcome to DTC's daily—what's now/next in ecommerce so founders, marketers, and operators can survive and thrive.Weekly newsletter: https://newsletter.ecommcowboy.com/Made possible by:Postscript - https://postscript.io/sms-benchmarks?utm_source=Ecomm+Cowboy+Show&utm_medium=Show&utm_campaign=Ad+Read&utm_id=Ecomm+CowboyAMP - ⁠https://postscript.io/sms-benchmarks?utm_source=Ecomm+Cowboy+Show&utm_medium=Show&utm_campaign=Ad+Read&utm_id=Ecomm+CowboySeguno - https://www.seguno.com/?utm_source=Ecomm+Cowboy+Show&utm_medium=Show&utm_campaign=Ad+Read&utm_id=Ecomm+CowboyFollow Ecomm Cowboy:https://x.com/ecommcowboyhttps://www.linkedin.com/company/ecommcowboyhttps://www.instagram.com/ecommcowboy/https://www.tiktok.com/@ecommcowboyhttps://open.spotify.com/show/0q1Pp0rW8j6cehXToNTeJchttps://podcasts.apple.com/us/podcast/ecomm-cowboy/id1761749693

    1h 12m

  6. FEB 10

    Are Agencies Cooked? | Why Normies Hate Ads About AI | Will Roman, Founder of Chisos Joins (2.10.26)

    Welcome to DTC's daily—what's now/next in ecommerce so founders, marketers, and operators can survive and thrive.Weekly newsletter: https://newsletter.ecommcowboy.com/Made possible by:Postscript - https://postscript.io/sms-benchmarks?utm_source=Ecomm+Cowboy+Show&utm_medium=Show&utm_campaign=Ad+Read&utm_id=Ecomm+CowboyAMP - ⁠https://postscript.io/sms-benchmarks?utm_source=Ecomm+Cowboy+Show&utm_medium=Show&utm_campaign=Ad+Read&utm_id=Ecomm+CowboySeguno - https://www.seguno.com/?utm_source=Ecomm+Cowboy+Show&utm_medium=Show&utm_campaign=Ad+Read&utm_id=Ecomm+CowboyFollow Ecomm Cowboy:https://x.com/ecommcowboyhttps://www.linkedin.com/company/ecommcowboyhttps://www.instagram.com/ecommcowboy/https://www.tiktok.com/@ecommcowboyhttps://open.spotify.com/show/0q1Pp0rW8j6cehXToNTeJchttps://podcasts.apple.com/us/podcast/ecomm-cowboy/id1761749693

    11 min

  7. FEB 9

    Super Bowl Winners & Losers | Consumers More Confident in 2026 | Steele Walker Joins (2.9.26)

    We start with Super Bowl winners and losers, unpacking which brands earned attention, which ones missed, and why so many ads are becoming instantly forgettable. From Dunkin’ and Levi’s to AI brands that couldn’t convert attention into impact, we break down what worked, what didn’t, and what it means for the future of advertising.We also talk about the brands that won without running a Super Bowl ad at all. While others spent millions, creator‑led distribution and smart giveaways dominated the conversation. This segment digs into why attention strategy now matters more than airtime.Next, we’re joined by Steele Walker, former MLB player and CEO of SpinGrip and Kitted Global. Steele shares his journey from professional baseball to building a fast‑growing physical product brand. We talk about solving real athlete problems, healing the yips, earning trust with D1 and pro players, creator partnerships, and what it actually takes to scale a product with authenticity.We then get into this week’s tasty trends, including Amazon surpassing Walmart with $700B in sales, why consumer confidence is rising but spending behavior is changing, and how TikTok has become a real distribution channel, not just a top‑of‑funnel play.We wrap with brand and culture moves that caught our attention, from Kith x Skims ice cream to Bloom dominating TikTok and Amazon, and why IRL experiences, sampling, and culture‑driven launches are winning right now.— — —Weekly newsletter: https://newsletter.ecommcowboy.com/Made possible by:Postscript - https://postscript.io/sms-benchmarks?utm_source=Ecomm+Cowboy+Show&utm_medium=Show&utm_campaign=Ad+Read&utm_id=Ecomm+CowboyAMP - ⁠https://postscript.io/sms-benchmarks?utm_source=Ecomm+Cowboy+Show&utm_medium=Show&utm_campaign=Ad+Read&utm_id=Ecomm+CowboySeguno - https://www.seguno.com/?utm_source=Ecomm+Cowboy+Show&utm_medium=Show&utm_campaign=Ad+Read&utm_id=Ecomm+CowboyFollow Ecomm Cowboy:https://x.com/ecommcowboyhttps://www.linkedin.com/company/ecommcowboyhttps://www.instagram.com/ecommcowboy/https://www.tiktok.com/@ecommcowboyhttps://open.spotify.com/show/0q1Pp0rW8j6cehXToNTeJchttps://podcasts.apple.com/us/podcast/ecomm-cowboy/id1761749693

    1h 3m

  8. FEB 7

    Willie Nelson's New CPG Brand | Time to Make YouTube Videos Now | Patrick Barnes Joins (2.6.26)

    We’re breaking down the biggest shifts happening right now across AI, media, ecommerce, and culture — from unexpected breakout brands to platform power plays that will shape the next decade.On this episode, we cover:• How Willie Nelson quietly built an $80M beverage brand — and why it’s being positioned as the Olipop of the category• A single brand doing $75M in 2025 using Snap Ads while everyone else ignores the channel?• Why DTC AI healthcare feels inevitable — and terrifying at the same time• The rise of continuous hormone tracking and what it unlocks (and risks)• Spotify selling physical books (yes, really) — and what it says about platforms becoming tastemakers• Meta testing a standalone app for AI‑generated “vibes” content• YouTube quietly dominating all of streaming with $60B in revenue in 2025 — and why brands still underinvest• A deep interview with Patrick Barnes, CEO of AMP, on dashboards, LTV myths, and what healthy ecommerce businesses actually look like• Why “teaching the algorithm” matters more than blaming it — and how clarity compounds over timeThis is a fast‑moving, opinionated episode about where leverage is shifting — in distribution, branding, technology, and consumer trust.— — —Weekly newsletter: https://newsletter.ecommcowboy.com/Made possible by:Postscript - https://postscript.io/sms-benchmarks?utm_source=Ecomm+Cowboy+Show&utm_medium=Show&utm_campaign=Ad+Read&utm_id=Ecomm+CowboyAMP - ⁠https://postscript.io/sms-benchmarks?utm_source=Ecomm+Cowboy+Show&utm_medium=Show&utm_campaign=Ad+Read&utm_id=Ecomm+CowboySeguno - https://www.seguno.com/?utm_source=Ecomm+Cowboy+Show&utm_medium=Show&utm_campaign=Ad+Read&utm_id=Ecomm+CowboyFollow Ecomm Cowboy:https://x.com/ecommcowboyhttps://www.linkedin.com/company/ecommcowboyhttps://www.instagram.com/ecommcowboy/https://www.tiktok.com/@ecommcowboyhttps://open.spotify.com/show/0q1Pp0rW8j6cehXToNTeJchttps://podcasts.apple.com/us/podcast/ecomm-cowboy/id1761749693

    1h 18m
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About

DTC's daily show — what's now/next in ecommerce so marketers can survive and thrive.

Information

  • Creator
    Chris Hall x Colin Dougherty
  • Years Active
    2024 - 2026
  • Episodes
    37
  • Rating
    Explicit
  • Copyright
    © Chris Hall x Colin Dougherty
  • Show Website
    Ecomm Cowboy