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We Are Moving!
Jan 28, 2026
0m 43s
They Said They’d Never Do Ads
Jan 23, 2026
Unknown duration
Be Bold in 2026: Gemini’s Rise, Nike’s Struggle, and the Agentic Future of Shopify
Jan 18, 2026
Unknown duration
The Quiz Show Featuring The E-commerce Podcasts That Got Way Out of Control
Dec 21, 2025
Unknown duration
The Silent Crisis in E-Commerce Leadership Nobody Is Talking About With Scott Silverman
Dec 17, 2025
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| Date | Episode | Topics | Guests | Brands | Places | Keywords | Sponsor | Length | |
|---|---|---|---|---|---|---|---|---|---|
| 1/28/26 | We Are Moving!✨ | podcast updateeCommerce+3 | — | Watson WeekendWatson Weekly+3 | — | Watson WeekendWatson Weekly+3 | — | 0m 43s | |
| 1/23/26 | They Said They’d Never Do Ads | The first episode of the new Watson Weekly Friday edition, featuring Rick Watson and Jessica Lesesky, debuts a new format focused on news and commentary related to e-commerce and retail. The new format includes three stories in the "Headline Hangover" section and one main story.In this episode:Amazon’s Luxury Nightmare: Why a $475M investment in Saks Global went to zero and why Amazon is calling it "financial malpractice."Gap’s Hollywood Move: Gap hires a Paramount heavy hitter as its first Chief Entertainment Officer. Is brand-as-media the future of fashion?The $63 Billion Ad Leak: New data reveals massive levels of invalid bot traffic across TikTok and LinkedIn.OpenAI’s Ad Pivot: The "ChatGPT Go" plan is here. Rick and Jess discuss why OpenAI is finally embracing ads to combat their $12B burn rate and what this means for the future of Google Search.Format Update: Guest interviews are moving to Wednesdays, and our hard-news deep dives will drop every Friday.The Watson Weekly Friday Edition is sponsored by Mirakl. Chapters:0:00 – Introducing: A New Format for the Watson Weekly1:15 – Headline Hangover: Amazon’s Luxury Disaster3:42 – Why Amazon is Calling Saks "Worthless"5:50 – Gap Hires a Chief Entertainment Officer: Genius or Gimmick?8:15 – The $63 Billion Ad Fraud Problem (TikTok vs. Meta)11:30 – Main Story: OpenAI Officially Launches Ads14:05 – ChatGPT Go & The New Sponsored Search17:20 – OpenAI’s $12B Burn Rate vs. Revenue20:10 – The Future of AI Search: Will it Kill Google?22:45 – Closing Thoughts & New Show Schedule#watsonweekly #openai #advertisingfraud #amazon #saksglobalchapter11 #googlesearchThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp | — | ||||||
| 1/18/26 | Be Bold in 2026: Gemini’s Rise, Nike’s Struggle, and the Agentic Future of Shopify | The first Watson Weekend show of 2026 serves as a post-mortem for the NRF conference, where Rick Watson and Jessica Lesesky recap the live event held at the Asylum in New York City and share "Nostradamus-style" predictions for 2026. The overarching theme for the coming year is "be bold," urging businesses to move past the economic hesitations of 2025.The show highlights three major industry shifts:The AI Wars: The hosts predict that Google’s Gemini will maintain its adoption momentum over OpenAI due to Google's vast data ecosystem, its integration into Android and Samsung devices, and its move to become the "default layer of intelligence" for the internet via the UCP protocol.Nike’s Innovation Deficit: Despite a leadership change, Nike is criticized for losing its "cool" and "shelf dominance" by over-prioritizing Direct-to-Consumer (DTC) strategies at the expense of wholesale and its core running category. The hosts note that Nike’s margins are significantly lagging those of competitors like On.Shopify’s Evolution: Shopify is seen as transitioning from a "storefront company" to an AI and payments powerhouse. With heavy investments in "agentic commerce," 2026 is expected to be the year these AI announcements deliver tangible results.The episode concludes with a critique of the NRF conference itself, noting that while the industry is hopeful, many vendors are still failing to articulate the actual impact and data behind their AI products.Housekeeping: Rick Watson is reorganizing the content for Watson Weekly and Watson Weekend, with an increased focus on the newsletter. There will be weekly interviews on Wednesdays, and the Watson Weekly remaining on Mondays. The Watson Weekend will move under the Watson Weekly banner as the weekend edition.#watsonweekly #shopify #nike #shopifyThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp | — | ||||||
| 12/21/25 | The Quiz Show Featuring The E-commerce Podcasts That Got Way Out of Control | The Watson Weekend Festive Jeoparty is a special holiday podcast episode featuring a Jeopardy-style quiz among four e-commerce and retail podcast teams: Team NYC (Rick Watson and Nick Kaplan), Retail Razor (Ricardo Belmar), Future Commerce (Philip Jackson and Brian Lange), and OGs Scott Wingo and Jason Goldberg. The game involves answering questions about retail trends, e-commerce, industry buzzwords such as agentic commerce, BNPL, retail media networks, and consumer behavior in 2025. Jessica Lesesky moderates the chaotic but fun competition, with rules including buzzing in and timed answers. Throughout the game, participants discuss key retail events and trends of 2025, such as consumers' unexpected resilience amid economic concerns, the plateauing of e-commerce growth, and the evolving role of commerce in culture. The episode ends with reflections from the participants on 2025 as a transformative year in retail, the announcement of the winners (Scott and Jason), and an invitation to join Rick Watson at the upcoming NRF event. The show closes with a festive dance party.ChaptersIntroduction of the Watson Weekend show - 0:00Introducing the podcast teams - 2:21Festive Jeoparty quiz - 6:40Festive dance party - 43:23Live taping of the Watson Weekend show at NRF 2026. Watson Weekend Live at NRF 2026, Presented by RadialSunday, January 11, 20264:00 PM – 8:00 PMAsylum NYCRSVP here: https://www.rmwcommerce.com/nrf-2026The Watson Weekend is sponsored by Mirakl.“In commerce, you don’t need another tool. You need a growth partner. The Mirakl platform is powering the next era of retail for the brands and retailers ready to move. Powered by AI and built for what’s next."#watsonweekend #festiveseason #jeoparty #ecommerce #retailThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp | — | ||||||
| 12/17/25 | The Silent Crisis in E-Commerce Leadership Nobody Is Talking About With Scott Silverman | In this special episode of the Watson Weekend, Rick Watson is joined by Scott Silverman, Co-founder of CommerceNext and Principal of Scott Silverman Associates, to talk about e-commerce leadership themes he is seeing.E-commerce leadership is being structurally devaluedSenior digital and e-commerce leaders are increasingly sidelined. Compensation for roles like VP of E-commerce has fallen sharply compared to five years ago, leading many experienced leaders into fractional or interim roles rather than full-time executive positions. This reflects a reduced willingness by companies to invest heavily in seasoned digital leadership. Hollowing out of the middle and loss of institutional expertiseOrganizations still maintain C-suite digital ownership (often under CMOs), but the layers beneath are increasingly filled by leaders new to e-commerce. Many veterans who helped build digital retail during its formative years are no longer embedded inside companies, creating a gap in applied experience, pattern recognition, and innovative mindset. Innovation risk in the age of AI and agentic commerceWith AI, LLMs, and agentic systems posing existential strategic questions, the lack of empowered internal digital leaders is concerning. Consultants can advise, but they lack political capital and long-term accountability. True innovation requires internal leaders willing to take risk, own transformation, and push bold strategies—something currently missing in many organizations Interim leadership has limitsWhile interim CMOs or fractional executives can help stabilize or transition organizations, this model can dilute innovation if overused. Transformation requires leaders with “skin in the game,” not rotating or part-time executives whose tenure and authority are inherently limited Talent turnover and short executive tenures compound the issueCMO turnover has long been high, but the combination of short tenures and interim leadership further weakens long-term brand and digital strategy. This environment makes sustained innovation especially difficult for legacy retailers trying to modernize, rather than for new digital-native entrants#watsonweekend @leadership #ecommerceleadershipThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp | — | ||||||
| 12/14/25 | A Marketplace Should Be Your Second Floor In Digital Retail with Ulta Beauty’s James Lang | This week's Watson Weekend episode features hosts Rick Watson and Jessica Lesesky, who deliver a news analysis in an entertaining Headline Hangover, plus holiday advertising commentary you do not want to miss. The show reflects on a turbulent retail year, previews a memorable holiday Jeopardy-style episode, and features an in-depth interview with James Lang, Head of Marketplace at Ulta Beauty.Holiday Advertising RecapUnderwhelming holiday ads in 2025, with many brands recycling familiar creative.Notable highlights:The Farmer’s Dog: emotional, pet-focused storytelling that resonated strongly.LEGO: creative anti-doomscrolling message that celebrates play and imagination.Amazon: reused a proven holiday ad, reinforcing speed, convenience, and family moments rather than novelty.Headline HangoverMajor retail headlines discussed:Uber + Shopify: Partnership enabling one-hour delivery for millions of merchants, intensifying last-mile competition with Amazon.Walmart: Expanded drone delivery pilots (Atlanta and other metros), following earlier success in Dallas–Fort Worth.Saks Global: Deep financial distress highlighted by delayed vendor payments, revenue declines, EBITDA losses, and aggressive discounting—raising concerns about long-term viability.Urban Outfitters: Adoption of an AI-powered supply chain compliance platform to manage regulatory complexity, traceability, and supplier data.James Lang, Head of Marketplace, Ulta Beauty, joins the show to discuss Ulta Beauty’s marketplace, which launched in October 2025.Ulta Marketplace StrategyPositioned as the “second floor” of Ulta’s digital store, not a separate experience.Fully integrated: one cart, one checkout, loyalty rewards, and easy returns.Invite-only marketplace with curated, brand-direct sellers (no resellers, no buy box).Core PrinciplesGuest-first mindset: trust, consistency, and ease matter more than fulfillment mechanics.Brand protection: brands do not compete against themselves; authenticity is non-negotiable.Asset-light, margin-accretive model: reduces inventory risk while expanding assortment.Internal AlignmentStrong executive sponsorship and cross-functional buy-in.Marketplace seen as a strategic growth lever, not a side experiment.The Watson Weekend is sponsored by Mirakl.“In commerce, you don’t need another tool. You need a growth partner. The Mirakl platform is powering the next era of retail for the brands and retailers ready to move. Powered by AI and built for what’s next."ChaptersIntroduction - 0:00Headline Hangover - 7:39Introducing James Lang - 19:21Show ends - 57:13#watsonweekend #marketplace #retail #ultabeautyThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp | — | ||||||
| 12/7/25 | The Marketing Industry Does Not Want You To Hear This With Trevor Testwuide | Watson Weekend host Rick Watson is joined by Nick Kaplan for the week's retail and e-commerce news. The headline hangover contains results from Black Friday and Cyber Monday, and Amazon is testing 30-minute deliveries. The company's AI assistant Rufus continues to make headlines. There is also a discussion on the closing of Omnicom's IPG acquisition.The week's special guest is Trevor Testwuide, CEO and Co-Founder of Measured, who talks about marketing measurement being broken, incrementality, and the problem with ROAS.Holiday Recap: Black Friday & Cyber MondayBlack Friday delivered stronger-than-expected results; Cyber Monday was surprisingly muted with fewer real-time pundit updates than usual. Shopify’s admin and checkout systems experienced downtime during Black Friday, creating chaos for brands needing to adjust promotions or track performance.Changing consumer behavior: Traditional Black Friday “doorbusters” and in-store frenzy continue to fade. Promotions now stretch well before and after the holiday.Amazon Headlines30-Minute DeliveryAmazon is piloting 30-minute delivery in select cities using micro-fulfillment centers, targeting high-frequency, convenience-driven categories (snacks, coffee, toilet paper, household essentials).This pushes deeper into Instacart/DoorDash territory and raises expectations for ultra-fast delivery nationwide.Rufus AIAmazon’s shopping assistant continues expanding across the site. The hosts question whether Rufus drives incremental sales or merely accelerates discovery for customers who would have purchased anyway. Strong use case: summarizing product info, filtering five-star results, and translating reviews into clearer insights.Agency Consolidation: Omnicom × IPGThe Omnicom–IPG deal closes, continuing the “big gets bigger” trend in advertising and media agencies. Thesis: scale enables more efficient data use and technology investment, but real-world synergies rarely reach the promised levels.Rising AI adoption places mid-market agencies at risk, amplifying consolidation pressure.The core of the episode is a deep discussion between Rick Watson and Trevor Testwuide on marketing measurement, attribution, and incrementality.Why Marketing Measurement Is BrokenFor years, the industry relied on Last-touch attribution, in which the channel closest to the sale gets 100% credit.Multi-touch attribution (MTA) tries to map every impression and click across the buyer journey. MTA became unreliable after 2016 due to privacy walls and tracking limitations. Many brands still rely on outdated methods because they’re easy, familiar, and embedded in reporting workflows.Incrementality: The Modern StandardIncrementality answers the real question:Did this ad actually cause additional sales, or would they have happened anyway? It isolates causal impact from correlated behavior—critical when high-intent shoppers convert regardless of ads.Media Mix Modeling (MMM)MMM provides long-term correlation analysis but not causality. Measured uses MMM combined with incrementality experiments to calibrate and improve accuracy.Problem With ROASROAS is simple but misleading—especially for bottom-funnel channels that “harvest” demand. Replacing ROAS with incremental ROAS or incremental contribution margin gives more truthful signal.Why CFOs Love IncrementalityIt speaks the language of finance: causal return, marginal contribution, efficiency. When incremental data confirms executives’ intuition about overspending in low-value channels, support for change accelerates.The Watson Weekend is sponsored by Mirakl“In commerce, you don’t need another tool. You need a growth partner. The Mirakl platform is powering the next era of retail for the brands and retailers ready to move. Powered by AI and built for what’s... | — | ||||||
| 11/23/25 | A Standard For Commerce Operations, A Non-Profit and Jeoparty Part Deux with Kelly Goetsch | Rick Watson, Jessica Lesesky, and Nick Kaplan warm up the show with jokes about last week’s performance and introduce the episode’s segments. They highlight Jeoparty, Headline Hangover, and the week's special guest, Kelly Goetsch.Headline Hangover: The team guesses blacked-out words from recent retail and e-commerce headlines.* Levi’s chooses Microsoft to deploy AI- and agentic-commerce solutions internally to improve efficiency and collaboration.* Lowe’s builds out its $8.8B wholesale business as DIY slows, reflecting macroeconomic pressures, rising material costs, and softening home-improvement demand.* Whatnot looks like “all of commerce” — The livestream shopping platform is booming:~$6B GMV, 140+ categories, 20M minutes of live content viewed last week, strong traction with younger audiences, and zero legacy tech debt → accelerated innovation with AI tools like Snap List.Rick “wins” Headline Hangover—the group jokes that this is a rare event.Kelly Goetsch from Pipe17 joins the show to discuss the launch of The Order Network Exchange (onX) and the Commerce Operations Foundation.The industry lacks a standard for connecting selling channels to fulfillment systems. Every OMS, WMS, 3PL, and marketplace uses different formats, leading to slow integrations, high operational overhead, fragile point-to-point connections, and fragmented inventory visibility.The SolutiononX Standard + MCP (Model Context Protocol)Defines standard tools and resources for order, inventory, and fulfillment data.Allows AI agents to consistently query backend systems.Gives vendors interoperability without bespoke APIs.Makes OMS and 3PL systems more “swappableThe Commerce Operations Foundation has 62+ members, including major OMS vendors like Manhattan, IBM Sterling, Kibo, Fluent, etc.Goal: Full standard published by January 1, 2026, with implementations rolling out in Q1–Q2 2026.MCP allows AI heads (GPT, Claude, etc.) to speak directly to order systems:“How many orders today?”“What’s the inventory of pink socks?”Reduces dependence on hacky webhooks.Jeoparty Part Deux:A retail spin on Jeopardy with categories such as:* Chapter Eleven (Nick Kaplan's love language)* Did Tobi really say this?* Sam Alt-Delete (AI & Sam Altman themed)* M&A* New kids on the block (e-commerce edition)* Easy picturesMemorable AnswersJoanne's bankruptcyTikTok Shop / Shein confusionTariff schedules with a wreath“Year of the Discount”Walmart + Vizio acquisitionGEO → the new SEOThe Watson Weekend is sponsored by RithumIn commerce, every second counts.Rithum connects every channel with AI automation and insights,helping brands grow profitably across marketplaces, dropship, and retail media.Learn more at rithum.com#watsonweekend #ai #jeoparty #onxThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp | — | ||||||
| 11/16/25 | The End of Instacart? Airbnb’s Grocery Solution Announced | The Watson Weekend hosts, Rick Watson and Jessica Lasesky, and guest Nick Kaplan discuss retail and commerce trends for Q4 and 2025. This week’s headline hangover includes the resurgence of Toys R Us, Airbnb's pilot kitchen stocking service with Instacart, and the integration of AI to enhance efficiency rather than replace humans.The Big 2025 “Jeoparty” Retro GameJeoparty host Jessica Lasesky uses the Watson Weekend version of the popular TV game show Jeopardy to try and confuse or showcase the brilliance of Rick Watson and Nick Kaplan. What did the previous Watson Weekend guests have to say about categories/topics such as Riddle Me RMN, Culture Club, AI Illuminati, Marketplace Mayhem, and Things Rick Said That Shouldn’t Be on Record?AI & Tech Themes (AI Illuminati)AI will not replace humans — it will reveal themBeyond the Hype: The Future of Commerce, AI, and Human Creativity with Dilip KeshuShopify Summer ‘24 Edition is described as “AI for AI”A running joke that it was peak AI hype, - Shopify Editions Recap Conversation With Shopify AgenciesKristen Wiley: Half of AI tools were built to write… LinkedIn posts - Influencer Marketing Should Be A Car That Can Be Driven Anywhere with Kristen WileyWhat AI still cannot automate: “judgment” (or taste) - How a 115-Year-Old Company Uses A Framework That Contains Bridges, Boats, and Moats with David Katz and Beyond the Hype: The Future of Commerce, AI, and Human Creativity with Dilip KeshuCulture & Leadership Themes (Culture Club)“No courage in consensus.”Jo Baker from https://www.youtube.com/watch?v=ym5QZpt3xzM“Empathy doesn’t slow performance — it scales it.”Donna Felix from https://www.youtube.com/watch?v=Lb1K--Ylvd8The winning blend of traits: IQ + EQ + adaptability (AQ)Donna Felix from https://www.youtube.com/watch?v=Lb1K--Ylvd8Advertising and Retail Media Networks (Riddle Me RMN)The word Kiri Masters swore she’d never say again in 2025 -IncrementalityFrom https://www.youtube.com/watch?v=pQv5rWAAfNsMarketplace & Retail Themes (Marketplace Mayhem)“Everyone’s a disruptor… until the invoice shows up.”Jack Freeman from https://www.youtube.com/watch?v=vJTDWyWqXmI - VC perspective: marketplaces sound utopian until the economics hit. Sellers say marketplaces “empower sellers”—but sellers call it:“Commission with extra steps.A discussion of:- Ulta launching a marketplace and a future episode.- Beauty brands rising through TikTok.- The need to balance seller and buyer incentives.Marketplace guests:Michael McCluskey, from Lowe's - https://www.youtube.com/watch?v=8bMxX83kcPoLogistics & Ops (Flexport Says What)Delivery is the last touchpoint with the customerJohn Shea from https://www.youtube.com/watch?v=ydQpB23iEf4Golden rule: “Over-communicate and never miss a promise date.”Nate Skiver... | — | ||||||
| 11/9/25 | How an 18-Year-Old Outsmarted Big Tech and Raised $1.4M | The Watson Weekend hosts Rick Watson and Jessica Lesesky discuss the most important retail and e-commerce news from the past week. In the Headline Hangover, they discuss retail's Q4 challenges, AI's impact on brick-and-mortar stores, and retail media trends. They highlight Amazon CEO Andy Jassy's view that AI will accelerate the decline of physical retail, and discuss ThredUp's new peer-to-peer selling model. The hosts also address concerns about agentic commerce liability and Coca-Cola's use of generative AI in advertising. The episode includes an interview with Liam Fuller, an 18-year-old entrepreneur from Ireland who founded three companies and now runs Source, an AI operations tool for retailers. Liam explains how Source integrates with legacy systems to help operations teams access data and perform tasks more efficiently.He discusses the challenges of entering the US market, attracting engineering and sales talent, and balancing product development with business growth. Liam emphasizes the importance of product-market fit, cautious scaling, and targeting mid-market brands with complex back-office needs. He notes the rapid advancement of AI models and the mixed reactions among retail executives, ranging from fear to enthusiasm.The conversation concludes with advice for new founders and reflections on the evolving retail technology landscape, underscoring AI's transformative potential and the need for startups to innovate within traditional verticals.The Watson Weekly is sponsored by RithumIn commerce, every second counts.Rithum connects every channel with AI automation and insights,helping brands grow profitably across marketplaces, dropship, and retail media.Learn more at rithum.comChapters00:00 - Introduction02:50 - Headline Hangover15:17 - Introducing Liam Fuller21:15 - How do you pitch brands?24:42 - Hiring developers in France26:11 - Evaluating sales talent33:50 - Focus for the next 6 - 12 months 36:40 - Product market fit41:50 - Go to market44:49 - What does Source do?51:26 - Too many AI startups?54:27 - AI and retail trends57:20 - End of show#watsonweekend #ecommerce #ai #erpThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp | — | ||||||
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| 11/2/25 | The Watson Weekend Halloween Special | The Watson Weekend Halloween Special hosts Rick Watson, Jessica Lesesky, and Nick Kaplan discuss 2025 retail and tech headlines with a Halloween twist. Think of it as the e-commerce and retail news version of Saturday Night Live, but it happened on a Friday.The headline hangover features criticism of Pinterest's AI-powered personalization as a rebrand, analyzes Amazon's 14,000 job cuts as a culture and organizational issue rather than AI-driven, and discusses the growing role of AI agents in e-commerce,with retailers expected to adopt them. Target's holiday marketing includes bringing back Hot Santa. Comcast is innovating with programmatic ad buys that include linear TV, while WPP launches an AI platform aimed at SMBs to simplify marketing without agencies. The hosts then play a game of retail trick-or-treat, which highlights ongoing retail struggles, including store closures, a resurgence of counterfeit goods, challenges with chatbot customer service, and aggressive price competition that threatens margins. They foresee a difficult holiday season with margin pressures and potential bankruptcies.The Watson Weekend is sponsored by Mirakl. Growth isn't just about speed; it's about direction. Mirakl gives you the infrastructure to scale. smarter, not just faster, with marketplace, dropship, retail media, and a seller platform powered by AI and built for what's next.00:00 - Introduction04:37 - Headline hangover26:06 - The scariest stories of 202530:12 - Who wins in Q433:42 - A Halloween dance33:54 - Show ends#watsonweekend #halloween #retailclosure #counterfeit #chatbotThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp | — | ||||||
| 10/26/25 | How Caddis Uses Mirakl To Service An Underserved Demographic Via Marketplaces With Emma Spagnuolo | Watson Weekend podcast hosts Rick Watson and Jessica Leseski cover retail industry news, including Target's struggles and layoffs, potential large tariff refunds pending a Supreme Court ruling, and merchandising challenges for Netflix's hit series K-pop Demon Hunters. They discuss Amazon's launch of AWS RTB fabric, a cloud infrastructure for programmatic advertising. Rick interviewed Michael McCluskey, VP of Marketplace at Lowe's, three months ago on the Watson Weekend (https://www.youtube.com/watch?v=8bMxX83kcP) and attended the Lowe's Marketplace Seller Summit this past weekend and was recovering from a visit to Bojangels in North Carolina..The main feature is an interview with Emma Spagnuolo, CEO of Caddis Life, and Sophie Marchesue, Chief Customer Officer of Mirakl. Emma shares how she transformed Caddis Life, a stylish eyewear brand targeting an underserved older demographic, emphasizing brand authenticity and expanding through marketplaces with Mirakl's support. Emma also discusses her personal breast cancer journey and its influence on her compassionate leadership style. Sophie explains how AI improves marketplace catalog management and the emerging role of agentic commerce via large language models.ChaptersWelcome to The Watson Weekend - 00:31Headline Hangover - 04:44Introducing Emma Spagnuolo and Sophie Marchesue - 20:46Caddis mission and eye wear 21:25Assortment mix on marketplaces - 34:01Building The brand -36:29Servicing an Underserved Demographic - 37:30#watsonweekend #target #tariffs #netflix #awsThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp | — | ||||||
| 10/19/25 | From Spreadsheets to Shipping Label Fraud and Cross-Border e-Commerce with Tommaso Tamburnotti | Watson Weekend hosts Rick Watson and Nick Kaplan discuss the retail industry's current state, emphasizing AI's integration into shopping experiences, such as Walmart's partnership with OpenAI. They highlight the rapid innovation driven by AI, including new tools like OpenAI's video creation app, and note the proliferation of AI partnerships across major platforms like Salesforce. The episode's guest, Tommaso Tamburnotti, CEO of EasyShip, shares his journey from finance to e-commerce logistics, explaining how EasyShip was founded to simplify the complex challenges of cross-border shipping, especially in emerging markets like Southeast Asia. Tamburnotti details the rise of shipping label fraud, where bad actors exploit shipping labels to resell them at a profit, resulting in financial losses for carriers, platforms, and taxpayers. He discusses the types of fraud, its recent increase, and the industry's need for collaborative solutions involving AI and stricter KYC processes. The conversation also addresses the underinvestment in U.S. cross-border e-commerce, the impact of regulatory changes such as de minimis reforms, and strategies for brands to expand internationally by enabling global purchases and localizing their operations.Tamburnotti emphasizes the logistical industry's scalability challenges and its potential for growth once larger tech-driven companies emerge.The Watson Weekend is sponsored by Mirakl. Growth isn't just about speed; it's about direction. Mirakl gives you the infrastructure to scale. smarter, not just faster, with marketplace, dropship, retail media and a seller platform powered by AI and built for what's next.ChaptersWelcome to The Watson Weekend - :00:20Headline Hangover aka Stump the chump - 02:57Tommaso Tamburnotti introduction - 15:02Learning in Southeast Asia, complexity and lessons - 17:00Shipping label fraud - 28:10The different parcel fraud schemes - 31:08Who pays for the label fraud? - 35:15The $150 million scam in 2024 - 35:51Cross-border e-commerce - 46:24Show ends - 01:02:25#watsonweekend #fraud #shipping #shippinglabelfraud #crossborderecommerce The Watson Weekend is produced by @RMWCommerce .Subscribe to RMW Commerce YouTube channel: https://www.youtube.com/@RMWCommerceThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp | — | ||||||
| 10/12/25 | Search Is In An Advantageous Position For AI-based Commerce with John Andrews | The latest Watson Weekend podcast episode, hosted by Rick Watson and Jessica Lesesky, discusses recent retail developments, including the elimination of the de minimis rule impacting U.S. imports, Starbucks' Taylor Swift-themed in-store experience to regain customers, Instacart 's integration with Tiktok for retail media targeting, and Paypal 's 5% cash back offer on BNPL purchases to boost holiday sales. The Watson Weekend is sponsored by Mirakl because growth isn't about just speed. It's about direction. Mirakl gives you the infrastructure to scale smarter, not just faster, with marketplace, dropship, retail media, and a seller platform built for what's next and powered by AI.The episode features an interview with John Andrews, CEO and Co-founder of Cimulate, who shares his extensive e-commerce background from Endeca to Nike and now AI-driven commerce. John explains how Cimulate uses large language models and synthetic personas to enhance search and merchandising by understanding customer intent and context, enabling more personalized and conversational shopping experiences. He stresses that while AI advances are transformative, human merchants remain vital, and retailers must prepare for rapid shifts in commerce technology.. Welcome to The Watson Weekend - 00:00:00Headline Hangover - 00:03:15Introducing John Andrews - 00:19:00Shopping in 2028 - 00:25:02What's different - 00:36:05Search is not solved 00:40:22Are retailers ready for an agentic world? - 00:53:41End of the show 1:02:56#watsonweekend #ai #artificialintelligence #agenticcommerce #searchThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp | — | ||||||
| 10/5/25 | The Internal Conflicts Retail Media Networks Create Inside Retailers and Brands with Kiri Masters | Watson Weekend hosts Rick Watson and Jessica Lesesky cover the latest retail industry news and trends this week. The headline hangover includes Gen Z's influencer-driven purchases, Mastercard's entry into retail media advertising, potential U.S. government influence over TikTok's algorithm, and Stripe's AI-powered commerce platform. Guest Kiri Masters, a retail media analyst, discusses the complexities of retail media networks, internal conflicts within retailers and brands, and the evolving role of AI and large language models in retail advertising and shopping.They explore challenges in aligning retailer and brand goals, the impact of agentic commerce on retail media, and the importance of customer loyalty and differentiation beyond price competition. The conversation highlights the potential for AI to transform retail media, creative, and customer experiences, while acknowledging current limitations and organizational hurdles.The Watson Weekend is sponsored by Mirakl — Because “Traditional eCommerce” Is Just Code for “Not Growing.” Join 450+ retailers scaling 6X faster with AI, automation, and enterprise-grade marketplaces, dropship, and retail media. It’s time to accelerate with Mirakl.Chapters:Welcome to The Watson Weekend - 0:00Headline Hangover 03:08Introducing Kiri Masters 18:07Internal conflicts within retailers and brandsThe evolving role of AI and large language modelsThe challenges of alignment between retailer and brand goals#watsonweekend #retailmedia #retailer #brand #widget #perfectcompetitionThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp | — | ||||||
| 9/28/25 | Influencer Marketing Should Be A Car That Can Be Driven Anywhere with Kristen Wiley | The Watson Weekend hosts Rick Watson and Jessica Lesesky discuss recent retail headlines, including Amazon's $2.5 billion lawsuit over alleged Prime subscription deception, Walmart's significant referral traffic from ChatGPT, Sephora's new affiliate program aimed at beauty creators, and Meta's talks with Google to enhance ad targeting using AI. They then interview Kristen Wiley, founder and CEO of Statusphere, a platform that enables brands to generate thousands of influencer posts efficiently by focusing on micro-influencers. Kristen shares her background as a creator and marketer, the slow and strategic growth of Statusphere, and the importance of providing a strong creator experience with human support alongside AI tools. She highlights how Statusphere helps brands achieve brand-safe content at scale, integrates influencer marketing across various campaign types, and addresses challenges like attribution and product-market fit. Kristen also discusses the evolving role of AI in marketing, the value of authentic human-generated content, and the potential for influencer data to influence AI models. The episode highlights the increasing importance of creator-driven marketing and the necessity for brands to cultivate communities and employ multi-channel strategies.Welcome to The Watson Weekend - 00:00Headline Hangover 02:56Introducing Kristen Wiley 15:47The importance of solving the creator experience 23:40Human touch in a post-AI world 25:33Using micro-influencers vs celebrities 28:25Generating ROI 30:52Attribution and its influencer challenge 35:00Nightmare situations 38:15Product Market fit to validate the need for 42:20 Statusphere community and content 43:40#watsonweekend #creators #microinfluencer #communityThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp | — | ||||||
| 9/21/25 | How a 115-Year-Old Company Uses A Framework That Contains Bridges, Boats, and Moats with David Katz | The Watson Weekend is sponsored by Rithum because if you’re in commerce, this is the event you can’t miss. Rithum LIVE is happening Sept 25 in New York City and Oct 9 in London—bringing together top brands, retailers, and leaders for a full day on the future of commerce. Learn more at rithum.com/nycHosts Rick Watson and Jessica Lesesky begin the show with a review of the news from the past weekend that caught their attention. The headline Hangover highlights Rent the Runway's subscriber growth but declining profits amid competition, Amazon CEO Andy Jassy's initiative to cut bureaucracy and return to a startup culture, and varied holiday sales forecasts, with consumers expected to benefit despite retailer margin pressures. YouTube's creator economy is noted for paying out over $100 billion to creators in four years, underscoring the platform's growth and influence. They then sit down with David Katz, EVP and CMO of Randa Apparel and Accessories, a billion-dollar company managing 35 brands, including Calvin Klein, Levi Strauss, Cole Haan, Dickies, Tommy Hilfiger, Columbia Sportswear, and 30 additional brands.🔥 KEY TOPICS COVERED:What percentage of the Randa business is as a licensee to another brand versus its own?What challenges are retailers facing, and how do they impact brands?The importance of direct engagement with customersHow Randa uses its “moats, boats, and bridges” frameworkThe challenges, such as tariff uncertainties, inventory risk, and the impact of public company pressures on retailersThe importance of looking to the future rather than recreating the normalThe conversation underscores the complexity of modern retail, the critical role of leadership and culture in navigating change, and the potential of AI and technology as tools rather than solutions. Chapters:Welcome to The Watson Weekend - 00:00Headline Hangover - 03:47Introducing David Katz 18:21Randa Apparel and Accessories business model 21:31Disruption and technology 23:43The current environment 27:30Exceptions prove the rule 33:45Uncertainty and supply chain 39:52Leadership and rationalization - 43:01Customer loyalty 43:36The tale of Hudson's Bay 46:24What role does data play in retail 50:54The impact of AI - 54:36The Taylor Swift impact 57:00Strategy in today’s world - 01:02:27What is the 'moats, boats, and bridges' framework - 01:10:00The need to look towards the future and not return to the normal - 01:17:45#watsonweekend #marketing #randa #leadershipThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp | — | ||||||
| 9/14/25 | The Future is Less If Then And More Prompts, Agents, and MCP - A SVP Looks to the Future | In this crossover episode, hosts Rick Watson and Jessica Lesesky talk with Shailesh Kumar, SVP of Engineering at Salesforce. He is the Head of Engineering for Salesforce Commerce & Retail Cloud. He previously served as SVP and Head of Engineering at ClickUp and VP of Engineering at MuleSoft, both of which were acquired by Salesforce.The headline hangover contains job numbers, Google, and the open web. Vivrelle added an AI stylist feature and Office Depot's new pickup promise.This episode of the Watson Weekend is sponsored by Rithum. Rithum Live 2025 will be in New York City on September 25, and Rick Watson will attend and be on stage. In London on 9 October, with Watson Weekend producer Vinny O'Brien, who will attend and be on stage. For more details, go to rithum.com/nycThis crossover episode, which includes the Oh Shift episode, can be viewed as an AI primer that will benefit listeners by clarifying the acronyms and terminology associated with agentic commerce.In this conversation, we dive into:The opportunity that the model context protocol (MCP) provides developers and, in the future, non-developersWhat Shailesh and this team want to evaluate from the current MCP pilot within Commerce Cloud. How software development will evolve as more tools and agents democratize the creation of software. The difference between public large language models and custom-built large language models.The distinction between deterministic output and non-deterministic flow has long existed in software engineering, along with the risks it poses to businesses. AgentForce, which Salesforce offers partners to develop agents on, and provides pre-built agents to Salesforce customers.How agents and platforms can interact with stitching and have guardrails around them to enable merchants to deliver joy to consumers.The impact that agentic commerce will have inside organizations and how to handle the speed of innovation.ChaptersWelcome to The Watson Weekend - 00:00Headline Hangover - 02:40Introducing the O Shift podcast - 13:08Introducing Shailesh Kumar -17:03What is Model Context Protocol (MCP)? - 19:13Why is Salesforce investing in MCP capabilities? - 21:47Who is the current target audience for MCP? - 23:00What is the difference between deterministic and non-deterministic workflows in AI agents? 26:02#watsonweekend #ohshift #mcp #modelcontextprotocolThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp | — | ||||||
| 9/7/25 | Fearless Communication in Chaos: An Ultra-Runner's Guide to Brand Leadership with Jenn George | This episode is brought to you by Mirakl. Because “Traditional eCommerce” Is Just Code for “Not Growing.” It’s time to do better than the status quo. Join 450+ retailers who are scaling 6X faster with AI, automation, and a platform built for what’s next. Marketplace, dropship, and retail media at enterprise-grade scale. It's time to accelerate with Mirakl.Join Rick Watson and Jessica Lesesky on The Watson Weekend as they sit down with Jenn George, Chief Communications Officer at Aspen Group. A seasoned brand leader and ultra-runner, Jenn shares her unique philosophy on simplifying the complex, finding clarity in chaos, and why communication is about steadying the humans inside a brand, not just crafting the perfect press release.In this conversation, we dive into:How to find signal in the noise and create a powerful narrative that drives action.The importance of authenticity and vulnerability, and why it beats perfection in an age of "AI slop".The "know, feel, do" framework for effective communication strategies.Real-world examples of brands and leaders who have successfully navigated major transformations.How Jenn's experience as an ultra-runner taught her that our perceived limits are often not real, a lesson she applies to business leadership.This is a must-watch for any leader who wants to master communication and build a resilient brand in today's unpredictable world.Chapters:Welcome to The Watson Weekend - 00:00:00Headline Hangover Starts - 00:03:40Introducing Jenn George - 00:16:38Communication in a World of Chaos - 00:19:51How to Build Brand Trust - 00:27:16Closing Remarks - 01:07:25This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp | — | ||||||
| 8/31/25 | The Next Generation of Retail: The Lead's D60 Next List & Influencer Marketing | This episode is brought to you by Mirakl. Because “Traditional eCommerce” Is Just Code for “Not Growing.” It’s time to do better than the status quo. Join 450+ retailers who are scaling 6X faster with AI, automation, and a platform built for what’s next. Marketplace, dropship, and retail media at enterprise-grade scale. It's time to accelerate with Mirakl.Join us on a special Wednesday edition of The Watson Weekend with hosts Rick Watson and Jessica Laseski. We’re excited to welcome Sonal Gandhi, Chief Content Officer at The Lead, and Margo Oshry, Senior Director of Talent and Influencer Marketing at Authentic. We dive into The Lead's brand-new "D60 next list" and discuss the future of retail leadership, the power of non-traditional backgrounds, and the evolving world of influencer marketing.Link: https://the-lead.co/the-d60-next-list/In this episode, we explore:The Lead’s new list of up-and-coming retail leaders and what makes them stand out.The strategic role of in-house influencer marketing and brand-building at Authentic.The importance of nurturing relationships and personal branding for career growth.How non-traditional backgrounds and diverse perspectives are driving innovation in the industry.The need for adaptability and speed in a fast-paced market where waiting too long can mean missing opportunities.This is a must-watch for anyone in the retail and e-commerce space who wants to stay ahead of the curve and understand what it takes to be a leader in the next generation.Chapters:Welcome to The Watson Weekend - 00:00:00Headline Hangover Starts - 00:02:59Introducing Sonal & Margo - 00:16:24The Rise of the Next Generation of Retail Leaders - 00:27:44The Power of In-House Influencer Marketing - 00:30:30Closing Remarks - 00:41:45This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp | — | ||||||
| 8/24/25 | Shipping Smackdown: Nate Skiver on the Parcel Industry's Biggest Myth | This episode is brought to you by Mirakl. Because “Traditional eCommerce” Is Just Code for “Not Growing.” It’s time to do better than the status quo. Join 450+ retailers who are scaling 6X faster with AI, automation, and a platform built for what’s next. Marketplace, dropship, and retail media at enterprise-grade scale. It's time to accelerate with Mirakl.Thanks to our sponsor, Crstl—The smarter way to EDI. See why brands like Neuro Gum and Andy Swim love it at CRSTL.ai.Join Rick, Jess, and special guest Nate Skiver, founder of LPF Spend Management, as they dive into a fiery discussion about the state of shipping in e-commerce. In this spicy wing-eating challenge, Nate debunks a major shipping myth and shares his expertise from over two decades in the retail and consulting world.In this episode, we explore:The biggest myth in shipping and why it's finally dying a slow death.How the e-commerce market has changed, creating more options beyond the "big three" carriers.The role of regional carriers and why more retailers are turning to them.How shipping technology advancements are making multi-carrier shipping easier to manage.Grab a glass of milk and get ready for a fast-paced, insightful conversation that will change the way you think about your shipping strategy!Chapters:Welcome to the Watson Weekend - 00:00:00Headline Hangover Starts - 00:02:49Introducing Nate Skiver - 00:16:31The Biggest Shipping Myth - 00:22:54The Future of the Parcel Industry - 00:26:56Final Thoughts - 00:46:17This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp | — | ||||||
| 8/17/25 | From Gin Lane to AI: Emmett Shine on the Future of Brands and Creative Obsolescence | Join us for a captivating episode of The Watson Weekend with guest Emmett Shine, the founder and creative director at Little Plains and co-founder of Pattern Brands. Known for helping launch and grow iconic brands like Harry's, Sweetgreen, and Warby Parker, Emmett sits down with Nick Kaplan to discuss the evolution of commerce, the role of human creativity in the age of AI, and what truly makes a brand resilient.In this interview, we dive into:How AI is changing the game for agencies and brand builders.The critical difference between "pull marketing" and "push marketing."Why authenticity and vulnerability are more important than polished perfection.The concept of "brand as a club" and the human need for belonging.Why retail spaces are evolving into "content studios" for a new generation of "experience collectors."Emmett's philosophy on staying ahead of creative obsolescence by being "as close to the metal as possible."This is a must-watch for founders, marketers, and creatives looking to understand how to build brands that matter in a rapidly changing world.Chapters:Welcome to The Watson Weekend - 00:00:00Headline Hangover Sponsored by Crstl Starts - 00:01:44Introducing Emmett Shine - 00:15:10The Future of Commerce & AI - 00:19:45Brands as Ecosystems & the Agency Model - 00:29:51Closing Remarks - 01:07:41This episode is brought to you by Mirakl. Because “Traditional eCommerce” Is Just Code for “Not Growing.” It’s time to do better than the status quo. Join 450+ retailers who are scaling 6X faster with AI, automation, and a platform built for what’s next. Marketplace, dropship, and retail media at enterprise-grade scale. It's time to accelerate with Mirakl.Thanks to our sponsor, Crstl—The smarter way to EDI. See why brands like Neuro Gum and Andy Swim love it at CRSTL.ai.This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp | — | ||||||
| 8/10/25 | Shein's Secret Weapon: The Gen Z Code that Every Brand Wants to Crack | Welcome to a special episode of The Watson Weekend as Vinny O'Brien and Nick Kaplan sit down with marketplace veteran George Chang, General Manager of Shein's third-party marketplace business. George provides a rare and fascinating look into how Shein has mastered the Gen Z market and built a massive global platform.George shares his insights on:The surprising details of Shein's global operations and community engagement efforts, including partnerships with the Boys & Girls Club of America.How Shein is winning with Gen Z, who are more likely to own a cell phone than to brush their teeth.The expansion of Shein's marketplace beyond fast fashion and the strategic criteria for new sellers.How Shein leverages its data platform and social features to create a unique and vibrant customer experience.The future of e-commerce, including the role of logistics, AI, and social commerce.This is a must-watch for anyone looking to understand one of the world's most talked-about e-commerce giants and its approach to building a platform for the next generation of consumers.Chapters:Welcome to The Watson Weekend - 0:00:00Headline Hangover Sponsored by CRSTL - 0:06:42Introducing George Chang - 0:17:39How Shein is Winning with Gen Z - 0:23:42The Marketplace Business Model & Seller Strategy - 0:41:29Final Thoughts and Farewell - 0:54:13This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp | — | ||||||
| 8/3/25 | From Orvis to Dinosaurs: A Conversation with Dave Finnegan on the Future of Brand Building | This week on The Watson Weekend, we sit down with brand-building veteran Dave "Finn" Finnegan, former CMO of Orvis and Build-A-Bear. Finn shares his unique perspective on marketing, drawing from his experiences in retail and as a budding anthropologist. We dive into the importance of authentic connections, the balance between data and storytelling, and how to create brands that truly resonate with customers. Plus, Finn tells us about his latest adventure: a dinosaur dig in Portugal!In this episode, we discuss:How studying anthropology provides a new lens for brand building.The critical difference between personalization and fostering a sense of community and belonging.The "one-two punch" of combining performance marketing with authentic storytelling.Why brands must focus on solving human problems, not just selling solutions.How brands can connect with Gen Z, who are "collectors of experiences, not collectors of stuff."The shift in retail from "square foot sales" to creating in-store "content studios."Finn's fascinating work with the Explorers Club and his recent dinosaur dig.Don't miss this insightful conversation that goes beyond the usual marketing metrics to explore the heart and soul of what makes a brand great.Chapters:Welcome to The Watson Weekend - 0:00:00Headline Hangover Sponsored by CSTRL - 0:01:43Introducing Dave "Finn" Finnegan - 0:16:53Anthropology and Marketing - 0:19:37The Balance Between Performance Marketing and Storytelling - 0:21:46From CMO to Dinosaur Digs: Finn's Anthropology Journey - 1:05:11The End of the Show - 1:15:10This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp | — | ||||||
| 7/20/25 | Beyond the Hype: The Future of Commerce, AI, and Human Creativity with Dilip Keshu | Join us for a captivating conversation with Dilip Keshu, founder of BORN Group and a visionary in global commerce. In this episode of The Watson Weekend Live Show, Dilip unpacks the evolving landscape of retail, the true potential of AI, and why human curiosity remains irreplaceable.We dive deep into:The saturated e-commerce market and how brands can truly stand out.The three stages of growth in a market: Keynesian model, Say's Law, and continuous innovation.Why "one-to-one personalization" hasn't fully arrived yet, and how AI is changing the game.The concept of a "unique buying proposition" and its importance in understanding customer behavior.The limitations of AI in moving culture and the enduring power of human inspiration.The mechanics behind agency roll-ups and the challenges of scaling "art".The evolution from customer experience (CX) to human experience (HX) and the role of purpose-driven design.Why curiosity is the ultimate driver for brands and leaders in a rapidly changing world.Don't miss this insightful discussion on the intersection of art, science, and the human element in the future of commerce!Chapters:0:00:00 - Welcome to The Watson Weekend0:03:00 - Headline Hangover: NRF Nexus 2025 Cancelled0:17:00 - Introducing Dilip Keshu: Founder of BORN Group0:38:00 - AI's Limitations: Can it Move Culture?0:51:00 - The Future: Metaverse & Immersive Commerce1:04:00 - Unasking the Question: A Leader's ApproachThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp | — | ||||||
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