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PODCAST

The Watson Weekend

The Watson Weekend podcast is now at https://www.watsonweekly.com/. Please subscribe here for more great shows. Welcome to The Watson Weekend – a rollicking weekly live conversation (and dance party) about all things retail, tech, and ecommerce! Hosts Rick Watson and Jess Lesesky and guests from all around the ecommerce world cut through the BS and bring you no-nonsense conversation, deep insights, and opinions that aren’t afraid to be contrarian. Join us for the livestream every Friday at noon

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All Episodes

00:43

We Are Moving!

The Watson Weekend ·

2026/01/28

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 industry leaders. And Fridays, the Watson Weekend show with Rick and Jess - you already know and love. So

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21:52

They Said They’d Never Do Ads

The Watson Weekend ·

2026/01/23

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

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23:46

Be Bold in 2026: Gemini’s Rise, Nike’s Struggle, and...

The Watson Weekend ·

2026/01/18

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

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43:56

The Quiz Show Featuring The E-commerce Podcasts That...

The Watson Weekend ·

2025/12/21

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

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11:43

Watson Weekend Special Episode with Scott Silverman

The Watson Weekend ·

2025/12/17

Rick Watson welcomes Scott Silverman to the RMW studio for a deep dive into the unexpected trends rocking the e-commerce industry's senior ranks.They discuss why many seasoned digital VPs are finding themselves in fractional roles or on the sidelines, the shrinking compensation for top e-commerce jobs, and how this shift—and the rise of the interim CMO—might be hurting innovation as we head into an era of AI and LLMs.Key Topics:The hollowing out of senior e-commerce roles.The shift from CMOs

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58:47

The Man Who Tried to Escape Retail (and Failed) -...

The Watson Weekend ·

2025/12/14

This week on Watson Weekend, we’re closing out our guest interviews for the year with James Lang, the leader behind Ulta Beauty’s fast-growing marketplace platform.James has spent more than 20 years building marketplace and dropship programs across Belk, ChannelAdvisor, Rithum, and now Ulta. He calls himself a “builder of asset-light strategies” before they were cool, and his career proves it.What we’re diving into:Ulta as a platform, not just a storeA marketplace designed to be invisible to the

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01:01:57

Watson Weekend Episode 90

The Watson Weekend ·

2025/12/07

Holiday Recap: Black Friday & Cyber MondayPerformance: Black Friday delivered stronger-than-expected results; Cyber Monday was surprisingly muted with fewer real-time pundit updates than usual.Shopify Outage: 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

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40:37

A Standard For Commerce Operations, A Non-Profit and...

The Watson Weekend ·

2025/11/23

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

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43:12

The End of Instacart? Airbnb’s Grocery Solution...

The Watson Weekend ·

2025/11/16

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

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59:02

How an 18-Year-Old Outsmarted Big Tech and Raised $1.4M

The Watson Weekend ·

2025/11/09

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

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35:29

The Watson Weekend Halloween Special

The Watson Weekend ·

2025/11/02

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

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01:03:18

How Caddis Uses Mirakl To Service An Underserved...

The Watson Weekend ·

2025/10/26

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

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01:04:03

From Spreadsheets to Shipping Label Fraud and...

The Watson Weekend ·

2025/10/19

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,

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01:04:31

Search Is In An Advantageous Position For AI-based...

The Watson Weekend ·

2025/10/12

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

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01:14:35

The Internal Conflicts Retail Media Networks Create...

The Watson Weekend ·

2025/10/05

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

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51:26

Influencer Marketing Should Be A Car That Can Be...

The Watson Weekend ·

2025/09/28

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

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01:20:10

The Future of Retail: Lessons from Rent the Runway,...

The Watson Weekend ·

2025/09/21

The Watson Weekend podcast episode covers recent retail technology and e-commerce news, highlighting 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

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39:34

The Future is Less If Then And More Prompts, Agents,...

The Watson Weekend ·

2025/09/14

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

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01:08:09

Fearless Communication in Chaos: An Ultra-Runner's...

The Watson Weekend ·

2025/09/07

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

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42:22

The Next Generation of Retail: The Lead's D60 Next...

The Watson Weekend ·

2025/08/31

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,

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