The Watson Weekly - Your Essential eCommerce Digest

Rick Watson and Jessica Lesesky break down three retail stories that challenge conventional wisdom this week.Revolve runs a 60% return rate — triple the online average — and just posted a 60% profit surge. They explain how baking return costs into margins and offering frictionless two-day shipping produces 80% full-price sell-through and a customer base that treats their bedroom like a fitting room. Physical storefronts in Aspen and LA are next.The Watson Weekly Weekend edition is sponsored by Avalara — automated tax compliance built for Shopify merchants, from calculation to returns. For more details: https://avalara.watsonweekly.com/Lowe's just launched Home Care Plus: $99 a year gets you two Red Vest associate visits for dryer vent cleaning, HVAC filter swaps, smoke detector batteries, and water heater flushes. The real story is what Lowe's gets in return — appliance age data and a direct line to upsell the aging homeowner market.And Buy Now, Pay Later is no longer just a checkout option. Millennials and Gen Z are 13x more likely than Baby Boomers to choose a merchant based on available financing. Fifty-five percent of Gen Z say installment options influence their choice of healthcare provider. BNPL is now a customer acquisition channel — and merchants paying 4.5–5% in fees may be getting the better end of the deal.

Rick Watson breaks down four stories shaping e-commerce and retail this week: Shopify's partner town hall reveals a company that treats API chaos as a brand attribute — and why that's a problem for any hyperscaler ambition. Lowe's bets $99 can put a red vest inside your home twice a year, and why that physical touchpoint is worth more than any app can replicate. The Watson Weekly is sponsored by Avalara — automated tax compliance built for Shopify merchants, from calculation to returns. For more details: https://avalara.watsonweekly.com/USPS wants an 8% fuel surcharge — the first in its history — and what the gap between that and Amazon's 3.5% tells you about structural efficiency. And Allbirds is done: not restructuring, not pivoting — dissolved, with a $4 billion brand selling for $39 million. Plus the Investor Minute: Zipline's $200M Series H, Cintas acquiring UniFirst for $5.5B, OpenAI snapping up Astral, Puratos buying Dawn Foods, and why Bark isn't going private yet.

Apple just turned 50. Amazon quietly acquired two robotics companies. And Allbirds — once valued at $4B— sold for $39M. Rick Watson and Nick Kaplan work through what these three stories have in common: the relentless pressure to find a next act before the first one runs out.The Watson Weekly Weekend edition is sponsored by Avalara — automated tax compliance built for Shopify merchants, from calculation to returns. For more details: https://avalara.watsonweekly.com/Topics this week: whether Tim Cook's Apple needs a visionary or just needs to win in AI, what Amazon's Rivr and Fauna acquisitions tell you about where last-mile delivery is actually going, and why Allbirds is a cautionary tale that applies to almost every DTC brand built on a single product. Plus: ambient AI through AirPods, the Rounders theory of the AI market, and why Rick switched from ChatGPT to Claude.Subscribe for weekly retail and commerce analysis: watsonweekly.com

Rick Watson is out. Nick Kaplan is in — and he's not giving the mic back.In this special Kaplan Wednesday episode, Nick takes the research prompts Watson built for his agentic commerce analysis and turns them on the very stories they were designed to interrogate.On the docket: Adyen's white paper claiming infrastructure is the constraint on agentic commerce (it isn't — and their own 95% AML false positive rate says why). Shopify's one-toggle Agentic Storefront promise and the data ownership problem it quietly creates. Klaviyo and Reebok Europe's Locale Aware Catalogs announcement — and the 149,999 merchants who aren't Reebok. The EU AI Act, which starts enforcement in five months and would like a word with every agentic protocol on the market. And the number that breaks every GMV projection: only 14% of shoppers trust AI recommendations enough to transact.The Kaplan Weekly is sponsored by Avalara. — automated tax compliance built for Shopify merchants, from calculation to returns. For more details: https://avalara.watsonweekly.com/The constraint isn't infrastructure. It's trust. Build that first.Happy April Fools. Rick will be back next week.Subscribe for weekly retail and commerce analysis: watsonweekly.com#ecommerce #kaplanwednesday #AIact #watsonwednesday

Live from the chaos of Shoptalk 2026 — where every booth promised an AI future and the floor proved retail is still fundamentally a contractual promise to a customer. Retail and e-commerce influencer Rick Watson is out on assignment in Las Vegas.This episode cuts through the agentic commerce noise. We get into what AEO (Agentic Commerce Optimization) actually requires operationally, why Shopify continues to eat the market while facing real limits at enterprise scale, and what the Stripe-Shopify relationship tells you about where payments infrastructure is heading.The Watson Weekend is sponsored by Avalara. For more information on Avalara, visit - https://avalara.watsonweekly.com/Plus: the honest conversation about AI ads, MCP protocols, and why building an AI Council too early might be the fastest way to slow your company down.Fix your margin problem first. Agentic commerce will not rescue a broken business model — it will just surface the damage faster.Subscribe to the Watson Weekly newsletter: https://www.watsonweekly.com

Darren Heaphy has spent his career at the intersection of e-commerce and logistics — AOL, Scurry, and now eDesk, where he leads product. His take on AI-driven support is blunt: brands are holding AI to a standard they never applied to their seasonal hires, and that double standard is costing them.In this episode, Rick Watson interviews and discusses the real shift happening in customer support — not chatbots replacing agents, but human teams moving from execution to orchestration. Darren calls it the "digital colleague" framework: start AI on low-risk work, build trust through auditability, and expand its scope as it earns it.The Watson Weekly interview is sponsored by Avalara — automated tax compliance built for Shopify merchants, from calculation to returns. For more details: https://avalara.watsonweekly.com/We also dig into a number most brands are sitting on without realizing it: 30–40% of support tickets are pre-purchase questions. Not complaints. Buying signals. And AI can convert those around the clock.What you'll hear:Why AI mistakes feel scarier than human mistakes — and whether that fear is rationalThe "glass box" approach to AI transparency that actually builds team trustHow support roles are evolving from typing to judgmentWhy the fundamentals — speed, accuracy, reduced uncertainty — haven't changed and won'tIf you've been watching AI take over the support conversation and wondering where your team fits, this one's for you.#CustomerSupport #AIinEcommerce #watsonweekly #interview

Rick Watson breaks down four stories worth your attention before Shoptalk.OpenAI's internal "code red" and what a pivot to enterprise and coding revenue actually signals ahead of a potential IPO; Dollar General and Dollar Tree earnings — both beating expectations, but with very different stories underneath the numbers; Apollo's credit chief calling private equity valuations "literally fiction," and why that matters for tech-focused PE portfolios still carrying COVID-era marks; and the three questions Rick is bringing to his Agentic Debate at Shoptalk this week — including whether brands are being sold snake oil on AI.Plus the Investor Minute: Agent Mail, Rhoda AI, Cart.com, Ernesta, and Quince.Watson Weekly is Sponsored by Avalara — Shopify's tax automation partner for US and global compliance., for more details: https://avalara.watsonweekly.com/

Dollar stores are quietly winning, Prime Day is jumping the calendar, and the AI arms race just hit its first major reboot. Rick Watson and Jessica Lesesky break down what actually moved this week in retail and commerce.Dollar General doubled its operating profit, Dollar Tree shed Family Dollar and beat estimates, and Five Below kept growing — while 99 Cents Only filed for bankruptcy. The value shift is real, and it's not just low-income shoppers driving it.Amazon is moving Prime Day to June. Is this a Q2 earnings play, a back-to-school land grab, or both? And what does that mean for Walmart, Target, and everyone else chasing the same wallet?The Watson Weekly Weekend edition is sponsored by Avalara. For more information on Avalara, visit - https://avalara.watsonweekly.com/Then: the agentic reboot. Adyen's co-CEO drops a white paper on infrastructure problems in agentic commerce. OpenAI's applications chief reportedly called a "code red" on internal focus. Amazon is adding senior engineer oversight to rein in autonomous code. Anthropic is quietly picking up enterprise market share — and OpenAI's people. Rick's verdict: we are in the early innings, and the wholesale strategy changes are just beginning.Chapters00:00 — Welcome & Intro01:14 — Dollar Store Earnings: Why Dollar General, Dollar Tree, and Five Below are winning — and who isn't04:24 — Amazon Prime Day Moves to June07:23 — The Agentic Reboot: Adyen's white paper, OpenAI's "code red," Anthropic's enterprise surge, and what it all means for brands building on AI

Tom Schmitt is CEO of Radial, North America's largest third-party fulfillment provider — and a company about to become something bigger. As part of the Bpostgroup's rebranding to Paxon, Radial is merging with its sister companies into a single global logistics brand built on decades of e-commerce infrastructure.The Watson Weekly is sponsored by Avalara. For more information on Avalara, visit - https://avalara.watsonweekly.com/Tom sat down with Rick Watson to talk about what he's actually seeing on the ground as AI enters supply chain — and the answer is more nuanced than most headlines suggest.Three things worth your time from this episode:The trust gap is real and measurable. Radial surveyed 1,000 US consumers: nearly two-thirds are uncomfortable sharing payment information with AI agents. That's not a technology problem — it's a brand problem operators need to solve first.Most AI projects are failing their ROI test right now — and that's expected. Tom's crawl, walk, run framework isn't a hedge; it's a diagnosis. Demand forecasting and pick-path optimization have measurable returns today. Fully autonomous warehouse orchestration does not — yet.Agentic commerce has a data standards problem nobody is talking about. Radial is a founding member of ONX — the Order Network Exchange — an open industry standard for how order, inventory, and fulfillment data moves between systems. Agentic commerce only works if agents read the same language. That work is already underway.Plus: the history of GSI Commerce, how Michael Rubin invented the direct-to-consumer industry, and why Fred Smith's old line about FedEx still tells you everything about where supply chain AI is headed.Subscribe to the Newsletter: Get it at https://www.watsonweekly.com/subscribe

Stripe just released an Agentic Technology Suite and positioned it as the infrastructure layer for the next era of commerce.]So who is Stripe actually building this for?The Watson Weekly Interview is sponsored by Avalara. For more information on Avalara, visit - https://avalara.watsonweekly.com/Salesforce Marketing Cloud posted -1% growth in Q4 FY2026 — the end of four years of deceleration and the start of something worse. Rebranding to Agentforce doesn't fix a product growth problem, and acquisitions are a slower fix than they look.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.Costco reported $2B in revenue, up 13.8%, driven by a limited SKU model and a merchandising strategy that creates genuine discovery. Digital is working too — personalized carousels drove $470M in e-commerce sales. The CEO is watching tariffs closely for the next 150 days.And the big structural story: retail's share of total consumer spending dropped from 34.3% in 2022 to 30.8% in Q4 2025. Amazon is absorbing the majority of what remains. The market is consolidating around Walmart and Costco for necessities and Amazon for everything discretionary — leaving mid-market and specialty retail in a structurally difficult position.Investor minute covers 5 stories from the world of IPOs, funding, private equity and more.#watsonweekly #stripe #costco #salesforcemarketingcloud #walmart #amazon

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:Why 95% of AI projects fail to deliver ROI — and it's not the technology's faultHow Mirakl jumped from 50% to 95% Gen AI adoption by eliminating the "copy and paste game"The self-driving car framework (L0 → L1 → L2) and how to use it to assess your own SaaS AI journeyHow Mirakl's Catalog Transformer reduced categorization errors by 50% and cut onboarding time from 15 days to under 2 hoursWhy solving the right problem matters more than solving a problem the right wayWhat agent commerce means for the future of retail — and how Mirakl Nexus is preparing for itWhether 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.

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/

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 Chapters0:00 - 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 BriefingAmazon's AI & Grocery Bet: Online stores are a $278 billion business. While physical retail has struggled, Amazon is doubling down on Whole Foods with a 20% increase in store count. Meanwhile, they are pouring $200 billion into capital expenditure, primarily for data centers and chips to fuel their AI driver.The Walmart Juggernaut: Walmart is executing at an elite level, with 60% of stores now using automated freight and 50% of e-commerce shipments being automated. Their membership and ads business has scaled significantly, reaching one-third of Amazon's operating profit.The Shopify/Stripe Power Couple: Shopify saw a 30% revenue increase to $11.5 billion. Their B2B sector is a hidden gem, growing 96%. Notably, 64 cents of every dollar in Shopify's merchant services business goes to their partner, Stripe.Meta's $83 Billion Gamble: Meta's advertising business remains highly profitable with a 30% operating margin, but the Reality Labs division has lost $83 billion to date. Mark Zuckerberg is betting that smart glasses will be a cognitive necessity within five years.UPS & PayPal in Transition: UPS is facing a massive volume decline as Amazon moves a million parcels a day away from their network. PayPal is currently described as a ship without a rudder, with rumors circulating that the company—or its crown jewel, Venmo—could be headed for a sale.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: The gold standard in tax and compliance solutions.Kasama: A premier software integrator and agency.Chapters:IntroductionAmazon commentaryMeta commentaryShopify commentaryPayPal commentaryUPS commentaryWalmart commentary#watsonweekly #webinar #amazon #meta #shopify #paypal #ups #walmart

Today on our show:Walmart Continues Its Tear: eCom Growth at 27%Perplexity Abandons Advertising to Maintain User TrustThe Great Parcel Reconfiguration No One is Talking AboutAbout That 2028 Global Intelligence Crisis- 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

The Big Retail Shakeup: Stripe's PayPal Play & Walmart's High-Income TakeoverThe 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: Why Stripe might be circling Venmo and what it means for the future of Stablecoin.Tariff Redo: Navigating the Supreme Court's recent ruling and why your CFO shouldn't be the one making marketing decisions.Walmart's Trillion-Dollar Climb: How 72% grocery penetration and automated fulfillment are widening the gap with the competition.Agentic Commerce: Is "Sparky" the real deal or just a higher AOV glitter?.Stay Ahead of the CurveSubscribe 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 captain6:29 - Trump Tariff Redux10:06 - Walmart earnings10:10 - 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 Community18:02 - The "Current 1776" Story: Hiring Customers as Creators 22:20 - Data-Driven Leadership and Business Metrics26:10 Advice for Large Retailers and the Future of D2C Subscribe to the newsletter at https://www.watsonweekly.com/subscribe

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

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.

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.

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.

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:

The "Growth at All Costs" era is over. Welcome to the era of Trust and AI Efficiency.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 / Timestaps0:00 - 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 #WatsonWeeklyThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp

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-watsonweeklyThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp

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 #customersupportThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp

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-watsonweeklyThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp

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-watsonweeklyThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp

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-watsonweeklyThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp

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-watsonweeklyThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp

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-watsonweeklyThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp

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-watsonweeklyThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp

Today on our show:Same-Day Facilities Key to Amazon's New Powerful Grocery StrategyWalmart CEO Doug McMillion Steps DownTheRealReal Records Record GMV During EarningsGoogle Releases Some AI Shopping Updates- 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-watsonweeklyThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp

Today on our show:Implications of Amazon Working with OpenAI and ChatGPTShopify Reports Great Q3 EarningsSome of the Worst Mistakes I Made First Time as CEOKlaviyo's Earnings Answer Some Key Questions- 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-watsonweeklyThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp

Today on our show:Walmart Holiday Plans Shows There Will Be BloodUPS Gains Margin, Plans Strong Peak, But Remains Mired in UncertaintyAmazon All In On Agentic - Reports Great EarningsShopify Merchants Go Live with ChatGPT Instant Checkout- 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-watsonweeklyThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp

Today on our show:Commercetools CEO is out, so what's next?Bigcommerce partners with Paypal to improve monetizationWill the new Ulta Beauty marketplace cook?Shopify and Lovable Integration Shows a Fire and Motion Strategy- 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-watsonweeklyThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp

Today on our show:Walmart Partners With OpenAI, Cannot Hold Back the TideS&P Global Puts Tariff Costs at $1.2T This YearSalesforce Partners With OpenAISaks Struggles to Deliver in Q2- 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-watsonweeklyThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp

Today on our show:Process Re-Engineering Is a Key Skill in the Age of AIStripe Link Moving More Consumer FacingIs OpenAI Building a Super App?Shopify CRO Bobby Morrison Forced Out- 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-watsonweeklyThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp

In this second episode of The CEO Spot, Rick Watson sits down with Matt Harris, Founder of Harris Digital. The interviews were conducted at Shoptoberfest 2025, discussing the state of B2B e-commerce and the challenges of 'hard commerce' faced by manufacturers and distributors.Harris explains that many companies struggle with legacy ERP systems, analog data management, and complex pricing models involving tiered and customer-specific discounts. He emphasizes the importance of product information management (PIM) systems in cleaning and centralizing data before launching e-commerce platforms. Harris shares his background, starting in the 1990s, with early e-commerce projects and how his agency helps mid-market manufacturers (with up to $1 billion in revenue) modernize sales by augmenting—not replacing—existing ERP systems. He discusses the friction caused by generational mindset shifts and private equity consolidation in these industries. On AI, Harris notes that while small-scale AI and analytics are useful, most enterprise AI projects fail to deliver revenue due to siloed data and unrealistic expectations; he advocates for building unified data lakes and warehouses as a foundation for future AI-driven business improvements.This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp

Today on our show:ChatGPT Is Actually The Ultimate In Influencer-Driven CommerceOpenAI x Stripe Agentic Commerce Protocol Has Makings of Silicon Valley Catfight- 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-watsonweeklyThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp

Today on our show:What the Hell Will Happen At Tiktok?Ryder Releases New eCommerce StudyKlaviyo Innovations Made Possible By Different Ecosystem ApproachOpenAI Announces They Are Pursuing Ads- 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-watsonweeklyThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp

Today on our show:Google and Paypal Announce New Commerce PartnershipAndy Jasy Fireside Chat With Andy Jassy at Amazon Accelerate ConferenceThe First Q4 Holiday Predictions Appear- 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-watsonweeklyThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp

We have a special episode of the podcast this week. Today we preview a new podcast from RMW Commerce — actually a Youtube Exclusive, called “Oh Shift! Where SaaS Meets AI”.In this week's episode, I interview the Shailesh Kumar, the SVP Of Engineering at Salesforce Commrece Cloud to talk about the company's approach and pilots in the world of AI and Model Context Protocol or MCP. To be clear, this is not any kind of sponsored interview. It's just an exploration of how the platforms - and I have asked them all to come on the program - are approaching AI and MCP, and what implications it has for brand and merchants.Today's episode is sponsored by Rithum.https://www.rmwcommerce.com/ecommerce-podcast-watsonweeklyThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp

Today on our show:Shopify Betting Big on DesignAmazon Still Stuck Muddling Through Day 2Why Software Sales Is Still Hard in 2025A New Podcast where SaaS Meets AI: Oh Shift- 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:Best Buy Relaunches Its MarketplaceTarget Earnings: Like a Slow-Moving Train WreckUpcoming RMW Commerce Events in Second Half of the YearWalmart Raises Revenue Guidance in Earnings Call- 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