The Watson Weekly: eCommerce Strategy & News

In this week’s Watson Weekly weekend edition, hosts Rick Watson and Jessica Lesesky talk about Dick’s Sporting Goods' viral Move moment, Elliott Hill in the New York Times, and the gap between consumer spending at Amazon and Walmart. Dick's Sporting Goods is number three in the App Store. Nike is running a PR campaign dressed as a turnaround. And the consumer spending data has already picked the winners of the next decade of retail — most people just aren't reading it correctly. The Watson Weekend edition is sponsored by Avalara. This week: what Dick's Move app gets right that every other retailer gets wrong about loyalty, why Elliot Hill's "innovation platforms" are a story for investors and not consumers, and what a nine-point drop in retail's share of consumer spending actually means for Amazon, Walmart, and everyone else fighting for what's left. The short version: utility beats AI features. NPS doesn't fix itself with a robot shoe. And if you're not Amazon or Walmart, you need a reason to exist — not a broader assortment. #watsonweeklyweekend #dickssportinggoods #nike #amazon #walmart

What does it actually take to go from AI experimentation to real business impact? In this episode of the Watson Weekly, Rick Watson sits down with Anne-Claire Baschet, Chief Data and AI Officer at Mirakl — the enterprise marketplace platform powering some of the world's largest retail brands. Anne-Claire shares how she went from a passion for sci-fi and mathematics to leading AI transformation at scale — spanning French national rail, a refurbished car marketplace IPO, and now a bold mandate at Mirakl: disrupt the business responsibly with AI. In this conversation, you'll learn: 50% to 95% Gen AI adoptionCatalog Transformerrightright wayagent commerce Whether you're a product leader, an AI executive, or building B2B SaaS, this episode is packed with hard-won lessons on strategy, adoption, and shipping AI that actually works. 🔔 Subscribe for weekly conversations on commerce, technology, and the future of retail. 📧 Newsletter: watsonweekly.com Chapters: #ArtificialIntelligence #AIStrategy #GenerativeAI #AgenticAI #AIAdoption

The AI shopping revolution is here — but who actually controls it? In this week's Watson Weekly, Rick Watson breaks down four stories reshaping the future of e-commerce. The Watson Weekly is sponsored by Avalara. For more information on Avalara visit - https://www.avalara.watsonweekly.com/ 🛒 Shopify vs. AI Agents — Shopify is making a bold bet: positioning itself as the back office of record for the agentic web. But if LLMs keep getting smarter, does the middleware even survive? Rick walks through two scenarios that every e-commerce operator needs to understand. 💳 The Stripe Annual Letter — $1.9 trillion in payment volume, a "stablecoin summer," and a controversial vision for Level 5 agentic commerce (AI that buys things before you ask). Is this a consumer-friendly future or a payments provider's dream dressed up as progress? The Watson Weekly is also sponsored by Mirakl. You don't need another tool; you need a growth partner. The Mirakl platform is powering the next era of retail for brands and retailers who are ready to move, powered by AI and built for what's next. 🤖 The Amazon-OpenAI $50B Deal — What it means for AWS, Nvidia, and Alexa — and the one glaring thing that's missing from the deal that tells you everything about how these negotiations really work. 🚚 The Logistics Rollup — Thoma Bravo is merging Auctane (ShipStation, Stamps.com, Metapack) with WWEX Group to build an end-to-end logistics intelligence stack. Could this be the most important supply chain bet of the decade? Plus: this week's Investor Minute covers Salesforce's acquisition of Momentum, Aritzia's buy of Fred Segal, and two fresh seed rounds in supply chain tech. 📬 Subscribe to Rick's newsletter: watsonweekly.com 🎙️ Find the podcast on all major platforms. #WatsonWeekly #AgenticAI #Stripe #Shopify #OpenAI #Amazon

Welcome to this weekend edition of Watson Weekly with Rick Watson and Jessica Lesesky! Today, we’re breaking down the biggest moves in retail and e-commerce from the past week.. We start with Target’s latest earnings, where a 1.7% dip in net sales has triggered a major turnaround strategy focused on beauty, food, and the Target Circle 360 premium membership. Then, we dive into Shopify’s investor event to discuss Agentic Commerce—is AI the new front door for online shopping? Finally, we analyze the massive $50 billion investment/partnership between Amazon and OpenAI. Why is Amazon mandating the use of its Trainium chips, and what does this mean for the future of AWS? The Watson Weekly Weekend edition is sponsored by Avalara. Key Chapters 0:00 - Introduction 0:49 - Target Earnings: Sales Slump & The 2026 Turnaround 6:09 - Shopify’s Agentic Commerce Front Door 9:50 - Amazon & OpenAI: The $110 Billion Funding Round #retailtech #Amazon #OpenAI #Shopify #TargetEarnings #EcommerceNews #AICommerce #AWS #WatsonWeekly

The dust has settled on Q4 and full-year 2025, and the numbers tell a fascinating story about the future of how we buy, ship, and sell. From Amazon’s record-breaking AWS growth to Walmart laying down the gauntlet, we are diving deep into the ripple effects these giants are creating across the entire ecosystem. In this episode, Rick Watson breaks down the split personalities of Meta, the agentic jump ball between Shopify and Stripe, and why UPS finds itself in an incredibly tight spot between Amazon and union contracts. Whether you’re a David moving fast or a Goliath trying to transform, these are the trends you cannot afford to ignore. Inside the Briefing Amazon’s AI & Grocery Bet:The Walmart Juggernaut:The Shopify/Stripe Power Couple:Meta’s $83 Billion Gamble:UPS & PayPal in Transition: The biggest risk right now isn't being small; it's being a giant that cannot move. If you're an underdog, use your speed to your advantage because you can move faster than the incumbents. Check out the full newsletter and more insights at: www.watsonweekly.com. Huge thanks to our sponsors: Avalara:Kasama: Chapters: Introduction Amazon commentary Meta commentary Shopify commentary PayPal commentary UPS commentary Walmart commentary #watsonweekly #webinar #amazon #meta #shopify #paypal #ups #walmart

Today on our show: - 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/@WatsonWeekly https://www.rmwcommerce.com/ecommerce-podcast-watsonweekly

The Big Retail Shakeup: Stripe’s PayPal Play & Walmart’s High-Income Takeover The retail and fintech worlds are moving faster than a 150-day tariff cycle, and this week, Watson Weekly Weekend edition hosts Rick Watson and Jessica Lesesky break down the seismic shifts you can’t afford to ignore. From "sharks in the water" at PayPal to Walmart’s sneaky-good transformation into a tech-first powerhouse, we’re unpacking the data behind the headlines. Is Stripe about to carve up the "Good Ship PayPal" to fuel its own world domination? And how has Walmart managed to win over the $100k+ crowd while automating its way to record margins? We’re diving deep into the "tale of two cities" in consumer spending and why being "bold" is the only strategy for 2026. In this episode: The PayPal Pivot:Tariff Redo:Walmart’s Trillion-Dollar Climb:Agentic Commerce: Stay Ahead of the Curve Subscribe to the Newsletter: Get the deep dives Rick and Jess mention at watsonweekly.com. Join the Conversation: Are you a "turtle shell" business or are you playing for growth this year? Let us know in the comments. Stay bold. Stay classy. Chapters: 0:00 - Welcome to the Watson Weekly Weekend 1:00 - PayPal without a captain 6:29 - Trump Tariff Redux 10:06 - Walmart earnings 10:10 - https://youtu.be/K-IPpyhtwMM #FintechNews #WalmartEarnings #Stripe #PayPal #EcommerceStrategy #WatsonWeekly #BusinessTrends2026 #SupplyChainInnovation #AgenticCommerce

The "subscription box" era might be over, but the membership era is just beginning. In this episode, Rick Watson sits down with John Roman, CEO of BattlBox, to pull back the curtain on how they survived the collapse of the 2015 subscription craze to become a powerhouse in the outdoor and survival space. John shares the unfiltered truth about why he prefers the term' membership' over 'subscription box,' and how shifting the focus to community and content saved their business. We dive deep into their unique content strategy—where 15% of their staff is dedicated to video production—and why John believes every modern brand should function like a media company. In this episode, you’ll learn: * The "CrateJoy" Origins: How BattlBox validated product-market fit on a niche marketplace before moving to their current scale. * The Inventory Nightmare: Why scaling to 10,000+ members requires production runs and forecasting six months out. * The Content Flywheel: Why 80% of BattlBox’s highest-value customers are regular YouTube viewers. * Hiring Your Customers: The story of how Brandon (Current 1776), a paying customer, became a full-time face of the brand. * Data-Driven Leadership: How John’s background as a professional poker player influences his obsession with churn, LTV, and retention. * The Future of D2C: Why John believes 70-75% of their 2026 revenue will still come from their core membership model. Timestamps: 0:00 - Introduction to BattlBox and Subscription Box Era 0:58 - Evolution from Subscription Box to Membership 5:00 - Inventory Management Challenges 8:53 - The Power of Content and Community 18:02 - The "Current 1776" Story: Hiring Customers as Creators 22:20 - Data-Driven Leadership and Business Metrics 26:10 Advice for Large Retailers and the Future of D2C Subscribe to the newsletter at https://www.watsonweekly.com/subscribe

Today on our show: - 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/@WatsonWeekly https://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 Saga We 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 Milestone Walmart 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 Bigger FedEx 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 Tech What keeps CEOs up at night? We identify the "one big risk" for the giants: Amazon:Shopify:Meta:OpenAI: #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:The WPP Open Strategy:Why AI Projects Fail:The Job Market:GSO (Generative Search Optimization): 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. Chapters 0:002:155:408:2012:4518:3023:1026:5030:00 #AI #SaaS #FutureOfWork #WPP #MachineLearning #GenerativeAI #TechTrends

Today on our show: - 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/@WatsonWeekly https://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 Timestamps 0:00 - 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.

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:The AI Trap:Hiring in the AI Era:To Replatform or Not?: 🕒 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

Today, I wanted to bring you something a little special. If you didn’t know, we host our own events here at the Watson Weekly, and our last one was in New York City on Sunday, January 11th prior to the National Retail Federation Big Show event. I gave a keynote to a packed audience of over 100 industry luminaries over one big topic - being bold in 2026. One of the most interesting ideas in the keynote is the idea of the Goliath Paradox. From the story of David and Goliath we understand that David won, but it is often not clear to us why he won and more importantly why Goliath lost. In particular, we are always taught that scale is safety. When in fact the only real moat is actually motion in today’s economy. If you’re not innovating, you’re dead. This causes a problem for larger companies because size often means you tend to slow down compared to your more nimble roots. It can be a harsh lesson to learn. One of my favorite parts of this keynote is the discussion about Skims and the opportunity they took advantage of over Victoria’s Secret. And the message behind it being that in 2026, brands need to compete on identity. What is your value proposition to your consumers, and Skims has been able to own the combination of technical fabric excellence and body positivity brilliantly. An intersected space that really did not exist until Sara Blakely and Spanx - who was probably the true innovator - was able to create the space that Kim Kardashian and Skims took advantage of. Finally, the keynote ends with a clear challenge. The goal is not to either be David or Goliath, but recognize that whichever you are there are advantages and disadvantages. And in either case, motion is not optional, it’s a requirement. 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 Evolution Pinterest 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: 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 Explosion Live 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

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.

Today on our show: - 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 / 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