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, explaining how EasyShip was founded to simplify the complex challenges of cross-border shipping, especially in emerging markets like Southeast Asia.

Tamburnotti details the rise of shipping label fraud, where bad actors exploit shipping labels to resell them at a profit, resulting in financial losses for carriers, platforms, and taxpayers. He discusses the types of fraud, its recent increase, and the industry's need for collaborative solutions involving AI and stricter KYC processes.

The conversation also addresses the underinvestment in U.S. cross-border e-commerce, the impact of regulatory changes such as de minimis reforms, and strategies for brands to expand internationally by enabling global purchases and localizing their operations.

Tamburnotti emphasizes the logistical industry's scalability challenges and its potential for growth once larger tech-driven companies emerge.

The Watson Weekend is sponsored by Mirakl. Growth isn't just about speed; it's about direction. Mirakl gives you the infrastructure to scale. smarter, not just faster, with marketplace, dropship, retail media and a seller platform powered by AI and built for what's next.

Chapters

Welcome to The Watson Weekend - :00:20

Headline Hangover aka Stump the chump - 02:57

Tommaso Tamburnotti introduction - 15:02

Learning in Southeast Asia, complexity and lessons - 17:00

Shipping label fraud - 28:10

The different parcel fraud schemes - 31:08

Who pays for the label fraud? - 35:15

The $150 million scam in 2024 - 35:51

Cross-border e-commerce - 46:24

Show ends - 01:02:25

#watsonweekend #fraud #shipping #shippinglabelfraud #crossborderecommerce

The Watson Weekend is produced by @RMWCommerce .

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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 direction. Mirakl gives you the infrastructure to scale smarter, not just faster, with marketplace, dropship, retail media, and a seller platform built for what's next and powered by AI.

The episode features an interview with John Andrews, CEO and Co-founder of Cimulate, who shares his extensive e-commerce background from Endeca to Nike and now AI-driven commerce. John explains how Cimulate uses large language models and synthetic personas to enhance search and merchandising by understanding customer intent and context, enabling more personalized and conversational shopping experiences. He stresses that while AI advances are transformative, human merchants remain vital, and retailers must prepare for rapid shifts in commerce technology..

Welcome to The Watson Weekend - 00:00:00

Headline Hangover - 00:03:15

Introducing John Andrews - 00:19:00

Shopping in 2028 - 00:25:02

What's different - 00:36:05

Search is not solved 00:40:22

Are retailers ready for an agentic world? - 00:53:41

End of the show 1:02:56

#watsonweekend #ai #artificialintelligence #agenticcommerce #search

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 AI and large language models in retail advertising and shopping.

They explore challenges in aligning retailer and brand goals, the impact of agentic commerce on retail media, and the importance of customer loyalty and differentiation beyond price competition.

The conversation highlights the potential for AI to transform retail media, creative, and customer experiences, while acknowledging current limitations and organizational hurdles.

The Watson Weekend is sponsored by Mirakl — Because “Traditional eCommerce” Is Just Code for “Not Growing.” Join 450+ retailers scaling 6X faster with AI, automation, and enterprise-grade marketplaces, dropship, and retail media. It’s time to accelerate with Mirakl.

Chapters:

Welcome to The Watson Weekend - 0:00

Headline Hangover 03:08

Introducing Kiri Masters 18:07

Internal conflicts within retailers and brands

The evolving role of AI and large language models

The challenges of alignment between retailer and brand goals

#watsonweekend #retailmedia #retailer #brand #widget #perfectcompetition