The Watson Weekend

Hosted ByRick Watson & Jess Lesesky

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.


All Episodes

The Watson Weekend | Episode We Are Moving!

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....

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode We Are Moving!
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The Watson Weekend | Episode 94: 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...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 94: They Said They’d Never Do Ads
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The Watson Weekend | Episode 93: 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...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 93: Be Bold in 2026: Gemini’s Rise, Nike’s Struggle, and the Agentic Future of Shopify
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The Watson Weekend | Episode 92: 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),...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 92: The Quiz Show Featuring The E-commerce Podcasts That Got Way Out of Control
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The Watson Weekend | Episode 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...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode The Silent Crisis in E-Commerce Leadership Nobody Is Talking About With Scott Silverman
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The Watson Weekend | Episode 91: 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...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 91: A Marketplace Should Be Your Second Floor In Digital Retail with Ulta Beauty’s James Lang
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The Watson Weekend | Episode 90: 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...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 90: The Marketing Industry Does Not Want You To Hear This With Trevor Testwuide
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The Watson Weekend | Episode 89: 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...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 89: A Standard For Commerce Operations, A Non-Profit and Jeoparty Part Deux with Kelly Goetsch
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The Watson Weekend | Episode 88: 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...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 88: The End of Instacart? Airbnb’s Grocery Solution Announced
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The Watson Weekend | Episode 87: 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...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 87: How an 18-Year-Old Outsmarted Big Tech and Raised $1.4M
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The Watson Weekend | Episode 86: 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...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 86: The Watson Weekend Halloween Special
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The Watson Weekend | Episode 85: 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...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 85: How Caddis Uses Mirakl To Service An Underserved Demographic Via Marketplaces With Emma Spagnuolo
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The Watson Weekend | Episode 84: 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...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 84: From Spreadsheets to Shipping Label Fraud and Cross-Border e-Commerce with Tommaso Tamburnotti
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The Watson Weekend | Episode 83: 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’...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 83: Search Is In An Advantageous Position For AI-based Commerce with John Andrews
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The Watson Weekend | Episode 82: 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...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 82: The Internal Conflicts Retail Media Networks Create Inside Retailers and Brands with Kiri Masters
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