The Watson Weekly: eCommerce Strategy & News

Watson Weekly
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Stop reading the headlines and start understanding the frameworks. The Watson Weekly is the premier resource for eCommerce executives, delivering sharp, independent strategy on the industry's most critical developments. Join 20-year veteran Rick Watson as he cuts through the noise to help you understand not just what is happening, but why it matters to your business. Broadcasting three times a week: Mondays: Strategic deep dives into earnings, mergers, and market shifts. Wednesdays: Candid interviews with C-Suite luminaries and tech innovators. Fridays: Join the Watson Weekend for Spirited debates on controversial topics with co-host Jessica Lesesky. From AI implementation and marketplace dynamics to supply chain logistics and retail operations, we cover the entire commerce landscape. Whether you are a CEO, VP, or operator, this is your competitive advantage in audio form.

  1. 1D AGO

    Shopify: It’s Always Been About the Checkout Stupid

    Welcome to the Watson Weekly Weekend Edition. Hosts Rick Watson and Jessica Lesesky dive into the post-Super Bowl landscape to break down the biggest moves in retail, tech, and AI. From the high-stakes world of $7 million for 30 second ads at the big game to the massive earnings reports from industry titans (hello Amazon), we’re unpacking what these shifts mean for the future of commerce. In This Episode:The AI Ad Wars: We review the ads from the big game spots from Claude (Anthropic), OpenAI, and Gemini. Is Anthropic just throwing shade at competitors, or is there a method to the "negative ad" madness? Target’s Executive Carousel: Target is shuffling the deck chairs again. With a new CEO and a history of moving merchants into marketing roles, we ask: why does Target seem "allergic" to a real CMO? Spotify vs. Amazon (The Book Edition): In a surprising move, Spotify is partnering with Bookshop.org to sell physical books. We explore why they’re helping independent bookstores while indie artists feel left behind. Amazon Earnings Deep Dive: AWS is back on "high-speed rail" growth, and the new AI assistant Rufus is already driving billions in sales. Plus, we discuss the genius of the "add to delivery" feature. Shopify’s AI Strategy: Shopify is growing at nearly 30% a year, but investors have one question: What is the AI strategy? Rick explains why Shopify’s "one trick"—the checkout—is still their greatest strength. The Watson Weekly Weekend Edition is sponsored by Mirakl: Powering the next era of retail. Video Timestamps0:00 - Welcome to Watson Weekend 0:54 - The Big Game Ad Economics: $233,000 Per Second 2:18 - The AI Ad Wars: Anthropic (Claude) vs. OpenAI 3:56 - Google Gemini’s "Heartstrings" Ad Campaign 5:14 - Target’s Leadership Shuffle: Why the "Roach Motel" Strategy? 8:17 - Spotify’s Strange Pivot into Physical Books 9:54 - The Indie Artist Royalty Gap which Should Make Publishers Worried 11:13 - Amazon Earnings: AWS High-Speed Growth & Rufus+2 13:06 - Amazon’s New "Add to Delivery" Feature 14:26 - The Future of Amazon Grocery & Whole Foods 15:05 - Shopify Earnings: B2B and International Growth 16:51 - Shopify’s AI Narrative: "It's the Checkout, Stupid" 19:54 - Final Thoughts Stay Bold. Stay Classy Subscribe to our Newsletter: watsonweekly.com and YouTube channel.

    23 min

  2. 3D AGO

    Why Your Agency is Falling for the AI Trap

    In this episode, host Rick Watson is joined by Mark Rubin, CEO of Kasama, to cut through the noise of the current agency landscape. Mark brings decades of experience from his time at Lyons Consulting, Precision Design Studios, and Moku Collective to discuss why the "AI Gold Rush" might be a trap and why replatforming your e-commerce site might be a mistake in 2026. In this episode, we discuss: The PE Cycle: Mark’s firsthand experience with private equity acquisitions and the "ticking clock" that begins once the checks clear.The AI Trap: Why clients are demanding AI provisions in contracts and how it’s creating a "margin pressure" that forces agencies to move from deliverables to results-based models.Hiring in the AI Era: The challenges of vetting developers who use AI tools and why "hiring slow and firing fast" is more important than ever.To Replatform or Not?: Mark’s controversial take on why brands should maximize their current tech stacks rather than chasing a "sexy" new platform that may result in a massive internal distraction. 🕒 Timestamps:0:00 – Introduction: Cutting through the Agency Noise 2:15 – Mark’s Journey: From .NET Developer to CEO 5:30 – The Reality of Private Equity and "The Clock" 9:45 – Is the AI Gold Rush a Trap for Agencies? 14:20 – The Evolution of Agency Pricing: Time & Materials vs. Results 18:10 – Why You Probably Shouldn’t Replatform This Year 22:45 – Closing Thoughts: Focus on the Basics #watsonweekly #watsonweeklyinterview #agency #ai #replatform

    25 min

  3. 5D AGO

    The Goliath Paradox: Why Scale is a Lie in Modern Commerce

    The Watson Weekly podcast, sponsored by Rithum, presents the keynote speech delivered in New York City on Sunday, January 11th, prior to the National Retail Federation Big Show. The. Watson Weekend Live at NRF Presented by Radial, keynote speech focused on "being bold in 2026.” The core idea is the "Goliath paradox," which argues that while David won, businesses often forget why Goliath lost. Rick Watson contends that the belief that "scale is safety" is a "lie," and in today's economy, the only real "moat is actually motion" because "size without motion is just a target". Larger companies risk slowing down, becoming heavy and slow like Goliath, who couldn't dodge the rock. The current era is the "age of intelligence," demanding that brands not just respond to demand but "anticipate demand before it even comes". The speaker uses Lululemon versus Alo and Victoria's Secret versus Skims as examples of bold challengers. In the case of Skims, the brand won by selling "the combination of high fashion engineering and body positivity," meeting customers "exactly where they are," while Victoria's Secret sold a fantasy. The ultimate challenge for 2026 is that brands need to compete on identity and "stand for something". The choice is between being a "giant who can't move" (a path of paralysis and incrementalism) or the "giant who learned how to dance," driven by a mindset of "speed, agility, and most importantly, adaptability". The Watson Weekly podcast is sponsored by Rithum. In commerce, every second counts. Rhythm helps brands and retailers connect every channel with AI-powered automation and insights, giving you the clarity to make smart decisions, adapt fast, and grow efficiently. Learn more at tithum.com. That's R-I-T-H-U-M.com. If you find conversations like this helpful, make sure you’re following the show so you don’t miss future episodes. Also, if you’re not subscribed to our newsletter, check that out at www.watsonweekly.com.

    24 min

  4. FEB 6

    Whatnot vs Traditional E-commerce: The Shift No One’s Talking About

    Join your Watson Weekly Weekend Edition hosts, Rick Watson and Jessica Lesesky, as they break down the biggest shifts in tech, retail, and e-commerce. From Pinterest’s AI pivot to Starbucks’ massive loyalty shakeup, we’re diving deep into the news moving the needle this week. 📌 Pinterest’s AI EvolutionPinterest is cutting 15% of its workforce (approx. 700–800 roles) to go all-in on AI. We discuss whether this is a genuine transformation or a "playbook" move to appease investors as user growth plateaus. Is the shift to "AI-proficient talent" enough to fend off TikTok and Reels? ☕ The New Starbucks Rewards (Launching March 10, 2026)Starbucks is reimagining loyalty with three distinct tiers designed to gamify your morning coffee: Green: The standard $1 = 1 star.Gold: Accelerated earning (1.2 stars/$) and non-expiring points.Reserve: A 2,500-star threshold (or $2,500 spend) with perks like all-expenses-paid trips to Tokyo, Milan, or Costa Rica.Note: The "free customization" era is ending with a new $10 cap on 200-star drinks.🛍️ Shopify vs. The "Robot Agents" Shopify’s latest partner update provides a blueprint for the AI era. They are redefining "partners" to include digital entities and tightening the reins on data—prohibiting developers from using merchant data to train external models. Plus, third-party apps must now feed directly into the Shopify AI Sidekick. 🃏 Whatnot & The Live Selling ExplosionLive shopping has evolved far beyond QVC. Whatnot has reached $8 billion in GMV by gamifying the collector experience. We explore why midsize cities like Rochester and Dayton are out-earning Chicago on a per-resident basis, and how categories like Beauty (up 791%) are exploding. "It’s not shopping; it’s entertainment." – Special Correspondent Shephard Lesesky on the addictive nature of live auctions. The Watson Weekly is sponsored by Mirakl. 0:00 – Intro 1:25 – Pinterest’s Strategic Pivot 5:31 – Starbucks Loyalty 2026 8:58 – Shopify’s New Rules 13:15 – The Rise of Whatnot 🚀 Stay Connected Subscribe to our podcast and YouTube channel for your weekly dose of commerce insights. Visit our website: https://www.watsonweekly.com #WatsonWeekly #EcommerceNews #StarbucksRewards #Shopify #Pinterest #LiveShopping #Whatnot #AI #RetailTrends

    24 min

  5. FEB 4

    NRF 2026 Debrief: Beyond the Buzzwords & The "Age of Intelligence"

    Is retail suffering from "buzzword fatigue"? In this 25-minute deep dive, Nick Kaplan and Rick Watson debrief the biggest themes, surprises, and reality checks from NRF 2026: Retail’s Big Show. From the noise surrounding "agentic commerce" to the practical startups actually moving the needle, we break down what brands need to know to survive the next era of retail. Key Takeaways: The Buzzword Barrier: Why brands are feeling lost in a sea of repetitive jargon and how to spot the difference between hype and high-impact tech. Practical Innovation: A look at the NRF Innovation Hub, featuring startups like Marpipe that are solving real-world problems in product feed and ad optimization. The Virtue of Patience: Navigating the rapid release cycle from giants such as OpenAI and Google requires a steady hand and a long-term view. The NRF Debrief is sponsored by Avalara and Freshmint. 📈 The Evolution of Commerce We trace the journey of the industry through four distinct eras: The Age of Presence (1990s): The race to get online. The Age of Efficiency: Streamlining the back end. The Age of Social: The rise of community-driven buying. The Age of Intelligence (Today): A fundamental shift from managing supply to generating demand through AI. 💡 Strategy for 2026 Success this year isn't just about having the biggest budget; it’s about adaptability. We discuss the importance of experimenting with technology budgets, verifying vendor claims with hard data, and managing the increasing complexities of the modern supply chain. "The barriers to entry for new businesses are lower than ever, but the noise is louder than ever. Boldness and adaptability are your best assets in 2026." 📌 Timestamps: 0:00 - Introduction & NRF 2026 Overview 3:15 - Cutting through the Buzzwords (Agentic Commerce?) 7:45 - Innovation Hub Highlights: Practical Solutions & Marpipe 12:30 - The Evolution of Commerce: From Presence to Intelligence 18:10 - How AI is Reshaping Retail Jobs & Processes 22:00 - Final Thoughts: Being Bold in 2026 Enjoyed the debrief? Make sure to Subscribe and hit the notification bell 🔔 to stay updated on our ongoing commerce insights.

    28 min

  6. FEB 2

    February 2nd, 2026: ChatGPT's 4% Fee Confirms Marketplace Economics, American Eagle to Close Quiet Logistics Business, UPS Releases 4Q 2025 Earnings and Provides 2026 Guidance, and Meta Earnings in Superintelligence We Trust

    Today on our show: ChatGPT's 4% Fee Confirms Marketplace EconomicsAmerican Eagle to Close Quiet Logistics BusinessUPS Releases 4Q 2025 Earnings and Provides 2026 GuidanceMeta Earnings in Superintelligence We Trust - and finally, The Investor Minute, which contains 5 items this week from the world of venture capital, acquisitions, and IPOs. Today's episode is sponsored by Rithum. https://www.rmwcommerce.com/ecommerce-podcast-watsonweekly

    15 min

  7. JAN 30

    What Really Happened inside the Shopify Massacre

    In this Friday edition of Watson Weekly, Rick Watson and Jessica Lesesky dive into the major shifts rocking the retail and tech landscape. From Shopify’s controversial partner strategy to Apple’s "defensive sprint" into wearable AI hardware, we break down what these moves mean for the future of the industry. On this week's episode: * The Fall of Quiet Logistics: American Eagle is sunsetting its Quiet Logistics business. Rick and Jess explore why owning your own supply chain can be a "heavy burden" if it’s not your core business. * Apple’s Ambient Ambitions: Is Apple panicking over all the OpenAI hype? Learn about the new AI pin designed to combat OpenAI, and why Apple is reportedly paying Google a billion dollars for the use of the Gemini model inside Siri. * Vinted’s American Dream: The European secondhand giant enters a crowded U.S. market. Can their buyer-fee model disrupt established players like Poshmark and The RealReal? *Shopify’s "Partner Massacre": Is Shopify abandoning the enterprise? Rick and Jess discuss the recent cuts to Shopify’s partner teams and CEO Tobi Lütke’s drive for "productivity over people". Key Takeaways: Why the "platform dream" failed for American Eagle. The difference between owning a logistics company and owning its "crown jewels". Why Shopify views anyone between them and their merchants as a "middleman". Support the Show: 🔔 Subscribe for more deep dives into retail and e-commerce news. #Ecommerce #Shopify #RetailTech #AppleAI #Logistics #Vinted #WatsonWeekly #thewatsonweekly

    26 min

  8. JAN 28

    From Banking to AI: The Future of Agentic Commerce with Gareth Cummings

    In this episode of The Watson Weekly, Rick Watson sits down with Gareth Cummings, CEO of eDesk, to discuss the massive shift in how brands interact with their customers. From pioneering domain-specific language models in 2018 to navigating the rise of TikTok Shop and Agentic Commerce, Gareth shares a masterclass in staying ahead of the tech curve. Gareth Cummings is the CEO of eDesk, an AI-native customer support platform built specifically for e-commerce. With a background in banking and telecom, he brings a unique, data-driven perspective to online retail. In this interview, you’ll learn: The Evolution of AI: Why customer skepticism has turned into an expectation for AI-driven support. Surviving the SaaS Slump: How e-commerce brands are pivoting toward profitability and value. TikTok & Authentic Engagement: Why new channels are essential for building brand trust in 2026. The Rise of AI Agents: What happens when AI starts making the purchases for us? Chapters / Timestamps 0:00 - Introduction: Meet Gareth Cummings, CEO of eDesk 2:15 - Career Evolution: From Banking and Telecom to E-commerce Tech 5:40 - The Early Days of AI: Building Language Models in 2018 9:25 - The Shift in Consumer Mindset: From AI Skepticism to AI Expectation 13:10 - Navigating the Modern SaaS Economy: Profitability vs. Growth 17:35 - Building Brand Loyalty: Why Trust Outperforms Price 21:50 - TikTok Shop and the Power of Authentic Engagement 26:15 - Turning Support Data into a Business Strategy Engine 30:40 - The Future of Agentic Commerce: When AI Does the Shopping 35:20 - Leadership Advice: Embracing the Pace of AI Change 38:45 - Closing Thoughts and Where to Follow Gareth The Watson Weekly is sponsored by Rithum. In commerce, timing is everything. That’s where Rithum comes in. We help brands and retailers keep every channel connected, so when the moment comes, you’re ready to act—launching faster, adapting quicker, and growing smarter. See how your business can grow at rithum.com. that's R-I-T-H-U-M.com #Ecommerce #AI #SaaS #CustomerSupport #TikTokShop #AgenticCommerce #TheWatsonWeekly #WatsonWeekly

    35 min
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Stop reading the headlines and start understanding the frameworks. The Watson Weekly is the premier resource for eCommerce executives, delivering sharp, independent strategy on the industry's most critical developments. Join 20-year veteran Rick Watson as he cuts through the noise to help you understand not just what is happening, but why it matters to your business. Broadcasting three times a week: Mondays: Strategic deep dives into earnings, mergers, and market shifts. Wednesdays: Candid interviews with C-Suite luminaries and tech innovators. Fridays: Join the Watson Weekend for Spirited debates on controversial topics with co-host Jessica Lesesky. From AI implementation and marketplace dynamics to supply chain logistics and retail operations, we cover the entire commerce landscape. Whether you are a CEO, VP, or operator, this is your competitive advantage in audio form.

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