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 .

Subscribe to RMW Commerce YouTube channel: https://www.youtube.com/@RMWCommerce

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

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 focusing on micro-influencers. Kristen shares her background as a creator and marketer, the slow and strategic growth of Statusphere, and the importance of providing a strong creator experience with human support alongside AI tools.

She highlights how Statusphere helps brands achieve brand-safe content at scale, integrates influencer marketing across various campaign types, and addresses challenges like attribution and product-market fit.

Kristen also discusses the evolving role of AI in marketing, the value of authentic human-generated content, and the potential for influencer data to influence AI models. The episode highlights the increasing importance of creator-driven marketing and the necessity for brands to cultivate communities and employ multi-channel strategies.

Welcome to The Watson Weekend - 00:00

Headline Hangover 02:56

Introducing Kristen Wiley 15:47

The importance of solving the creator experience 23:40

Human touch in a post-AI world 25:33

Using micro-influencers vs celebrities 28:25

Generating ROI 30:52

Attribution and its influencer challenge 35:00

Nightmare situations 38:15

Product Market fit to validate the need for 42:20

Statusphere community and content 43:40

#watsonweekend #creators #microinfluencer #community

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 and Oct 9 in London—bringing together top brands, retailers, and leaders for a full day on the future of commerce. Learn more at rithum.com/nyc

Hosts Rick Watson and Jessica Lesesky begin the show with a review of the news from the past weekend that caught their attention. The headline Hangover highlights 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 influence.

They then sit down with David Katz, EVP and CMO of Randa Apparel and Accessories, a billion-dollar company managing 35 brands, including Calvin Klein, Levi Strauss, Cole Haan, Dickies, Tommy Hilfiger, Columbia Sportswear, and 30 additional brands.

🔥 KEY TOPICS COVERED:

What percentage of the Randa business is as a licensee to another brand versus its own?

What challenges are retailers facing, and how do they impact brands?

The importance of direct engagement with customers

How Randa uses its “moats, boats, and bridges” framework

The challenges, such as tariff uncertainties, inventory risk, and the impact of public company pressures on retailers

The importance of looking to the future rather than recreating the normal

The conversation underscores the complexity of modern retail, the critical role of leadership and culture in navigating change, and the potential of AI and technology as tools rather than solutions.

Chapters:

Welcome to The Watson Weekend - 00:00

Headline Hangover - 03:47

Introducing David Katz 18:21

Randa Apparel and Accessories business model 21:31

Disruption and technology 23:43

The current environment 27:30

Exceptions prove the rule 33:45

Uncertainty and supply chain 39:52

Leadership and rationalization - 43:01

Customer loyalty 43:36

The tale of Hudson's Bay 46:24

What role does data play in retail 50:54

The impact of AI - 54:36

The Taylor Swift impact 57:00

Strategy in today’s world - 01:02:27

What is the 'moats, boats, and bridges' framework - 01:10:00

The need to look towards the future and not return to the normal - 01:17:45

#watsonweekend #marketing #randa #leadership

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 Watson Weekend is sponsored by Rithum. Rithum Live 2025 will be in New York City on September 25, and Rick Watson will attend and be on stage. In London on 9 October, with Watson Weekend producer Vinny O'Brien, who will attend and be on stage. For more details, go to rithum.com/nyc

This crossover episode, which includes the Oh Shift episode, can be viewed as an AI primer that will benefit listeners by clarifying the acronyms and terminology associated with agentic commerce.

In this conversation, we dive into:

The opportunity that the model context protocol (MCP) provides developers and, in the future, non-developers

What Shailesh and this team want to evaluate from the current MCP pilot within Commerce Cloud.

How software development will evolve as more tools and agents democratize the creation of software.

The difference between public large language models and custom-built large language models.

The distinction between deterministic output and non-deterministic flow has long existed in software engineering, along with the risks it poses to businesses.

AgentForce, which Salesforce offers partners to develop agents on, and provides pre-built agents to Salesforce customers.

How agents and platforms can interact with stitching and have guardrails around them to enable merchants to deliver joy to consumers.

The impact that agentic commerce will have inside organizations and how to handle the speed of innovation.

Chapters

Welcome to The Watson Weekend - 00:00

Headline Hangover - 02:40

Introducing the O Shift podcast - 13:08

Introducing Shailesh Kumar -17:03

What is Model Context Protocol (MCP)? - 19:13

Why is Salesforce investing in MCP capabilities? - 21:47

Who is the current target audience for MCP? - 23:00

What is the difference between deterministic and non-deterministic workflows in AI agents? 26:02

#watsonweekend #ohshift #mcp #modelcontextprotocol

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 seasoned brand leader and ultra-runner, Jenn shares her unique philosophy on simplifying the complex, finding clarity in chaos, and why communication is about steadying the humans inside a brand, not just crafting the perfect press release.

In this conversation, we dive into:

• How to find signal in the noise and create a powerful narrative that drives action.
• The importance of authenticity and vulnerability, and why it beats perfection in an age of "AI slop".
• The "know, feel, do" framework for effective communication strategies.
• Real-world examples of brands and leaders who have successfully navigated major transformations.
• How Jenn's experience as an ultra-runner taught her that our perceived limits are often not real, a lesson she applies to business leadership.

This is a must-watch for any leader who wants to master communication and build a resilient brand in today's unpredictable world.

• Welcome to The Watson Weekend - 00:00:00
• Headline Hangover Starts - 00:03:40
• Introducing Jenn George - 00:16:38
• Communication in a World of Chaos - 00:19:51
• How to Build Brand Trust - 00:27:16
• Closing Remarks - 01:07:25

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, Chief Content Officer at The Lead, and Margo Oshry, Senior Director of Talent and Influencer Marketing at Authentic. We dive into The Lead's brand-new "D60 next list" and discuss the future of retail leadership, the power of non-traditional backgrounds, and the evolving world of influencer marketing.

Link: https://the-lead.co/the-d60-next-list/

In this episode, we explore:

• The Lead’s new list of up-and-coming retail leaders and what makes them stand out.
• The strategic role of in-house influencer marketing and brand-building at Authentic.
• The importance of nurturing relationships and personal branding for career growth.
• How non-traditional backgrounds and diverse perspectives are driving innovation in the industry.
• The need for adaptability and speed in a fast-paced market where waiting too long can mean missing opportunities.

This is a must-watch for anyone in the retail and e-commerce space who wants to stay ahead of the curve and understand what it takes to be a leader in the next generation.

• Welcome to The Watson Weekend - 00:00:00
• Headline Hangover Starts - 00:02:59
• Introducing Sonal & Margo - 00:16:24
• The Rise of the Next Generation of Retail Leaders - 00:27:44
• The Power of In-House Influencer Marketing - 00:30:30
• Closing Remarks - 00:41:45