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 81: 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,...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 81: Influencer Marketing Should Be A Car That Can Be Driven Anywhere with Kristen Wiley
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The Watson Weekend | Episode 80: 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...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 80: How a 115-Year-Old Company Uses A Framework That Contains Bridges, Boats, and Moats with David Katz
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The Watson Weekend | Episode 79: 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 &...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 79: The Future is Less If Then And More Prompts, Agents, and MCP - A SVP Looks to the Future
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The Watson Weekend | Episode 78: 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...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 78: Fearless Communication in Chaos: An Ultra-Runner's Guide to Brand Leadership with Jenn George
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The Watson Weekend | Episode 77: 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...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 77: The Next Generation of Retail: The Lead's D60 Next List & Influencer Marketing
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The Watson Weekend | Episode 76: 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...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 76: Shipping Smackdown: Nate Skiver on the Parcel Industry's Biggest Myth
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The Watson Weekend | Episode 75: 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...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 75: From Gin Lane to AI: Emmett Shine on the Future of Brands and Creative Obsolescence
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The Watson Weekend | Episode 74: 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....

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 74: Shein's Secret Weapon: The Gen Z Code that Every Brand Wants to Crack
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The Watson Weekend | Episode 73: 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...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 73: From Orvis to Dinosaurs: A Conversation with Dave Finnegan on the Future of Brand Building
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The Watson Weekend | Episode 72: 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...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 72: Beyond the Hype: The Future of Commerce, AI, and Human Creativity with Dilip Keshu
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The Watson Weekend | Episode 71: Apps Expert DESTROYS Common Mobile Marketing Myths (75% of Ad Spend Goes Where?!)

Sue Azari, a distinguished e-commerce executive at AppsFlyer, exposes the shocking truths about mobile app marketing that most retailers are getting completely wrong. From why your “best customers” might...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 71: Apps Expert DESTROYS Common Mobile Marketing Myths (75% of Ad Spend Goes Where?!)
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The Watson Weekend | Episode 70: Lowe’s VP Reveals How They Built a $XXX Million Marketplace in 4 Months (Amazon Should Be Worried)

Michael McCluskey, VP of Marketplace at Lowe’s, drops bombshells about how they launched their marketplace faster than anyone expected and why traditional retail is dead. From competing with Amazon’s...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 70: Lowe's VP Reveals How They Built a $XXX Million Marketplace in 4 Months (Amazon Should Be Worried)
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The Watson Weekend | Episode 69: TikTok Shop SECRETS: $0 to #5 US Retailer – Former Political Operative Reveals All

David Baker, CDO at Beekman 1802, spills the secrets behind TikTok Shop’s explosive growth from political campaign tactics to beauty brand domination. From Obama’s digital team strategies to becoming...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 69: TikTok Shop SECRETS: $0 to #5 US Retailer - Former Political Operative Reveals All
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The Watson Weekend | Episode 68: GM Executive Reveals: Why ‘Execution Drives Morale, Not Vision’ – Enterprise Leadership Secrets

In this eye-opening full interview, Sid Jatia, GM’s Global VP of Digital Commerce & Service, drops truth bombs about what really works in large enterprise organizations. From Microsoft to...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 68: GM Executive Reveals: Why 'Execution Drives Morale, Not Vision' - Enterprise Leadership Secrets
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The Watson Weekend | Episode 67: Shopify Editions Recap Conversation With Shopify Agencies

Nick Kaplan steps in as guest co-host with Rick Watson —and yes, we doubled up on Nicks because mediocrity requires one, but excellence needs two. Nick and Rick, who...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 67: Shopify Editions Recap Conversation With Shopify Agencies
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