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PODCAST

The Watson Weekend

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 on LinkedIn at https://www.linkedin.com/in/ecommercestrategyconsulting/ and YouTube at

business business news

All Episodes

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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47:52

Shipping Smackdown: Nate Skiver on the Parcel...

The Watson Weekend ·

2025/08/24

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

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01:07:40

From Gin Lane to AI: Emmett Shine on the Future of...

The Watson Weekend ·

2025/08/17

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

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56:45

Shein's Secret Weapon: The Gen Z Code that Every...

The Watson Weekend ·

2025/08/10

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

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01:16:42

From Orvis to Dinosaurs: A Conversation with Dave...

The Watson Weekend ·

2025/08/03

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,

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01:06:46

Beyond the Hype: The Future of Commerce, AI, and...

The Watson Weekend ·

2025/07/20

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

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01:04:44

Apps Expert DESTROYS Common Mobile Marketing Myths...

The Watson Weekend ·

2025/07/13

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 not be what you think to the real reason Teemu is terrifying luxury brands, this conversation reveals the mobile strategies that actually drive revenue.🔥 Mind-Blowing Revelations:75% of mobile ad spend goes to remarketing (not acquisition!)Why the "best customers download apps" theory is

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01:05:10

Lowe's VP Reveals How They Built a $XXX Million...

The Watson Weekend ·

2025/06/29

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 drone delivery to the shocking truth about why most marketplace projects fail, this conversation reveals the inside strategy of America's second-largest home improvement retailer.Key Revelations:How Lowe's launched their marketplace in under 4 months (most take years)Why Amazon's grocery strategy is

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01:09:44

TikTok Shop SECRETS: $0 to #5 US Retailer - Former...

The Watson Weekend ·

2025/06/22

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 the #5 retailer in America, this deep dive reveals what actually works.🔥 Key Takeaways:Why TikTok Shop beats Instagram/Facebook 10:1 in social commerceThe "visual hook" formula that drives viral product salesWhy you need 10X more content than you think (and why most fails)How to turn influencers into a

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01:07:41

GM Executive Reveals: Why 'Execution Drives Morale,...

The Watson Weekend ·

2025/06/15

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 Under Armour to General Motors, Sid shares battle-tested strategies that challenge conventional leadership wisdom.🔥 Key Takeaways:Why execution beats vision for team motivationThe real reason cross-functional teams fail (it's not what you think)How GM turns service appointments into sales opportunitiesWhy

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01:03:02

Shopify Editions Recap Conversation With Shopify...

The Watson Weekend ·

2025/06/08

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 are in the same studio, talk about Peleton’s P2P play, Temu’s struggle, and they recap The Lead Summit.They are then joined by Shopify Agency operators to talk about their trip to Toronto for Editions.🧠 The Shopify Agency Lineup:Mark Perini – Founder of ICEE SocialJacquelyn Laufer – Driver Digital PartnerNick Thomson – Head of

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