The Watson Weekly: eCommerce Strategy & News

Today on our show:Stripe’s $140 Billion QuestionWhy Temu is the New Cross-Border StandardThe UPS $150k Exit: Strategic Rightsizing or a Teamster Trap?Is Agentic Commerce a Nothingburger? The Agentic Debate Series, presented by Logicbroker.- 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 Mirakl.https://www.watsonweekly.com/https://www.youtube.com/@WatsonWeeklyhttps://www.rmwcommerce.com/ecommerce-podcast-watsonweekly

This week on the Watson Weekly Weekend edition, Rick Watson and Jessica Lesesky are breaking down a massive shift in the retail and tech landscape. From the dramatic fall of a luxury giant to Walmart's historic milestone and the high-stakes risks facing Silicon Valley’s finest, we’ve got the insights you need to stay ahead.In This Episode🎭 As the House of Luxury Turns: The Saks Global SagaWe track the "episodic drama" of Saks Global’s decline, from unpaid vendors and empty shelves to the January Chapter 11 filing. We dive into the friction with Amazon and the aggressive store closures impacting Saks Off Fifth and Neiman Marcus.🛒 Walmart’s $1 Trillion MilestoneWalmart has officially joined the elite tech-heavy $1T market cap club. We discuss how their massive investments in supply chain automation and a "dot-com culture" (thanks to the legacy of Jet.com) are now allowing them to outpace Amazon’s e-commerce growth.📦 FedEx: Better, Not BiggerFedEx is pivoting away from "tiny cheap shipments" to focus on high-margin sectors like healthcare and aerospace. We look at their Network 2.0 strategy and how they are navigating the rise of de minimus shipments from players like Shein and TikTok Shop.+⚠️ The Existential Risks of Big TechWhat keeps CEOs up at night? We identify the "one big risk" for the giants:Amazon: Will the $200B AI backlog actually materialize?Shopify: Is a "high-performance sports team" culture sustainable for a 100-year company?Meta: The massive bet on "face computers" and ongoing legal distractions.OpenAI: The "show me the money" moment and the lack of native distribution.#Retail #Ecommerce #Walmart #SaksGlobal #FedEx #BigTech #Amazon #SupplyChain #WatsonWeekly

Is SaaS really dead? Will AI take your job next year? In this Watson Weekly Interview, Rick Watson talks with Dr. Daniel Hulme, Chief AI Officer at WPP and CEO of Satalia, to debunk the biggest myths surrounding Artificial Intelligence. From the changing architecture of software to the rise of "Economic Singularity," Dr. Hulme provides a masterclass on how businesses and individuals can navigate the rapidly evolving tech landscape.We dive deep into:The Future of SaaS: Why LLMs are amplifying—not killing—software.The WPP Open Strategy: How AI unlocked creativity and content creation at scale.Why AI Projects Fail: From "intoxicated graduate" syndrome to the trap of low-hanging fruit.The Job Market: Transitioning from economic disruption to a world of abundance and UBI.GSO (Generative Search Optimization): Move over SEO—learn how to brand your business inside the "brains" of LLMs.Whether you are a SaaS founder, a marketer, or simply curious about the future of humanity, this conversation offers a grounded, expert perspective on the AI revolution.Chapters0:00 - Introduction to Dr. Daniel Hulme2:15 - Myth: Is SaaS Dead?5:40 - The 3-Layer Architecture of Modern Software8:20 - How WPP Open uses AI for Creative & Content12:45 - 5 Reasons Your AI Initiative Will Fail18:30 - AI vs. Jobs: The Path to Economic Singularity23:10 - Universal Basic Income and the Future of Work26:50 - Introduction to Generative Search Optimization (GSO)30:00 - Closing Thoughts: Living Your "True Humanity"#AI #SaaS #FutureOfWork #WPP #MachineLearning #GenerativeAI #TechTrends

Today on our show:Amazon is a Vertically Integrated UtilityShopify Fiscal Year 2025 Earnings: a Pony with One Great Trick, Could it Be More?Kroger Opens a New MarketplacePaypal Earnings and David Marcus- 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 Mirakl.https://www.watsonweekly.com/https://www.youtube.com/@WatsonWeeklyhttps://www.rmwcommerce.com/ecommerce-podcast-watsonweekly

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 Weekend0:54 - The Big Game Ad Economics: $233,000 Per Second2:18 - The AI Ad Wars: Anthropic (Claude) vs. OpenAI3:56 - Google Gemini’s "Heartstrings" Ad Campaign5:14 - Target’s Leadership Shuffle: Why the "Roach Motel" Strategy?8:17 - Spotify’s Strange Pivot into Physical Books9:54 - The Indie Artist Royalty Gap which Should Make Publishers Worried11:13 - Amazon Earnings: AWS High-Speed Growth & Rufus+213:06 - Amazon’s New "Add to Delivery" Feature14:26 - The Future of Amazon Grocery & Whole Foods15:05 - Shopify Earnings: B2B and International Growth16:51 - Shopify’s AI Narrative: "It's the Checkout, Stupid"19:54 - Final ThoughtsStay Bold. Stay ClassySubscribe to our Newsletter: watsonweekly.com and YouTube channel.

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 Noise2:15 – Mark’s Journey: From .NET Developer to CEO5:30 – 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. Results18:10 – Why You Probably Shouldn’t Replatform This Year22:45 – Closing Thoughts: Focus on the Basics#watsonweekly #watsonweeklyinterview #agency #ai #replatform

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.

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 – Intro1:25 – Pinterest’s Strategic Pivot5:31 – Starbucks Loyalty 20268:58 – Shopify’s New Rules13:15 – The Rise of Whatnot🚀 Stay ConnectedSubscribe 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

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 CommerceWe 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 2026Success 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 Overview3:15 - Cutting through the Buzzwords (Agentic Commerce?)7:45 - Innovation Hub Highlights: Practical Solutions & Marpipe12:30 - The Evolution of Commerce: From Presence to Intelligence18:10 - How AI is Reshaping Retail Jobs & Processes22:00 - Final Thoughts: Being Bold in 2026Enjoyed the debrief? Make sure to Subscribe and hit the notification bell 🔔 to stay updated on our ongoing commerce insights.

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

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

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 / Timestamps0:00 - Introduction: Meet Gareth Cummings, CEO of eDesk2:15 - Career Evolution: From Banking and Telecom to E-commerce Tech5:40 - The Early Days of AI: Building Language Models in 20189:25 - The Shift in Consumer Mindset: From AI Skepticism to AI Expectation13:10 - Navigating the Modern SaaS Economy: Profitability vs. Growth17:35 - Building Brand Loyalty: Why Trust Outperforms Price21:50 - TikTok Shop and the Power of Authentic Engagement26:15 - Turning Support Data into a Business Strategy Engine30:40 - The Future of Agentic Commerce: When AI Does the Shopping35:20 - Leadership Advice: Embracing the Pace of AI Change38:45 - Closing Thoughts and Where to Follow GarethThe 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

Today on our show:Sam Altman Testing AdLowes to license its checkoutAI meets Davos and a Jassy SightingClaude Code Is Having a Viral Moment- and finally, The Investor Minute, which contains 3 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

Most AI pilots fail—at least, that’s the headline. But today’s guest is proving that doesn’t have to be true.In this Watson Weekly interview, Rick Watson goes behind the scenes with Chris Kellner, CEO of DigitalGenius, to discuss how a decade-old AI pioneer is navigating the modern LLM explosion. We move past the hype to explore how AI is actually rewriting the playbooks for sales, marketing, and customer support.In this episode, you’ll learn:* The "Locomotive" Metaphor: Why DigitalGenius didn't have to reinvent itself, but rather accelerated on existing tracks.* Sales & Marketing Rewired: How Chris’s team uses AI for call coaching, MEDPIC scorecards, and CRM automation to let humans focus on high-value closing.* UK vs. US Market Mismatch: Why traditional outbound playbooks failed when crossing the Atlantic and what they did to fix it.*The Competition for Culture: How an internal "Agent-Building" competition spurred unexpected creativity across the company.3 Hard Lessons in AI Support: The essential checklist for any leader deploying AI in customer service today.Chapters00:00 – Intro: Turning AI buzz into customer wins 03:15 – Chris Kellner’s journey from Banking to SaaS CEO 07:40 – Acceleration vs. Reinvention: Building the AI train line 14:20 – Rewiring GTM: AI call coaching and MEDPIC scorecards 22:10 – Market Mismatches: Lessons from scaling from the UK to the US 30:45 – Culture & Internal Adoption: The AI Agent competition 38:30 – Why most AI pilots fail (and how to make yours succeed) 45:15 – Build vs. Buy: When to go in-house and when to use a vendor 52:00 – Closing thoughts and key takeaways#watsonweekly #ai #customersupport

Today on our show:Walmart Shakes Up Its Leadership RanksNRF 2026 RecapMore Content Coming To You from the Watson Weekly- and finally, The Investor Minute which contains 4 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

Today on our show:It’s Time to Be Bold in 2026Welcome to NRF- 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

Today on our show it’s no news, just thank yous.It’s been a roller coaster of a year for everyone, and despite everything, you have tuned in. Walking your dog, on the way to work, even in the shower you were there. Listening, laughing, cringing, and hopefully, even learning.I started this podcast back in 2021 and look forward to doing it for many more years. The fact that our content and presence continue to grow each year is a testament to you.So, here it is. Thank you for listening. If you like what we’re doing, reach out. Tell us what you like about it, recommend it to a friend. And of course, have a Happy Holidays wherever the end of this year takes you.This is Rick Watson, signing off for the year. I also wanted to say a huge thank you to my partners in crime Hendrik, Libby, Kaylea, Jacque, Vinny and Ron, without you this podcast would not be possible.Today's episode is sponsored by Mirakl.https://www.rmwcommerce.com/ecommerce-podcast-watsonweekly

Today on our show:Shopify Winter Editions 2025 Special Podcast- 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 Mirakl.https://www.rmwcommerce.com/ecommerce-podcast-watsonweekly

Today on our show:Black Friday Cyber Monday - You Devil You!Sam Altman Calls a Code Red to Stop Google ThreatAmazon and Visa Partner on Agentic PaymentsNike CEO Purges John Donahoe’s Lieutenants- and finally, The Investor Minute which contains 3 items this week from the world of venture capital, acquisitions, and IPOs.Today's episode is sponsored by Mirakl.https://www.rmwcommerce.com/ecommerce-podcast-watsonweekly

Today on our show:Walmart Plans a CEO TransitionCommerce Operations Foundation Critical to Our Common Agentic FutureIntuit's Announcement Makes it Clear: OpenAI Coming for Operating SystemsWalmart Earnings Call Important for Everyone to Understand- 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