The Watson Weekend

Hello friends! I have an important update regarding the Watson Weekend. To make it easy for you to keep up with everything happening in commerce, we're consolidating our shows. We're officially moving the Watson Weekend into the Watson Weekly podcast feed. This completes our new lineup. Mondays, we contain your essential eCommerce digest. On Wednesdays, it will be deep dive interviews with industr...

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...

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 shift...

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 buzzwo...

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 devalued Senior digital and e-commerce leaders are increasingly sidelined. Compensation for roles like VP of E-commerce has fallen sharply...

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 Beaut...

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, C...

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 solution...

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 Game Jeoparty host Jessica Lasesky us...

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 se...

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 cultu...

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...

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...

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 holida...

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 c...

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...

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/nyc Hosts Rick Watson and Jessica Lesesky begin the show with a review of the news from the past weeken...

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...

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...

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 o...

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...

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...

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 operation...

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...

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 i...