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PODCAST

The Watson Weekly: eCommerce Strategy & News

Stop reading the headlines and start understanding the frameworks. The Watson Weekly is the premier resource for eCommerce executives, delivering sharp, independent strategy on the industry"s most critical developments. Join 20-year veteran Rick Watson as he cuts through the noise to help you understand not just what is happening, but why it matters to your business. Broadcasting three times a week: Mondays: Strategic deep dives into earnings, mergers, and market shifts. Wednesdays: Candid

business management

All Episodes

22:49

Trump Tariff Doo Doo Doo

The Watson Weekly: eCommerce Strategy & News ·

2026/02/27

The Big Retail Shakeup: Stripe’s PayPal Play & Walmart’s High-Income TakeoverThe retail and fintech worlds are moving faster than a 150-day tariff cycle, and this week, Watson Weekly Weekend edition hosts Rick Watson and Jessica Lesesky break down the seismic shifts you can’t afford to ignore. From "sharks in the water" at PayPal to Walmart’s sneaky-good transformation into a tech-first powerhouse, we’re unpacking the data behind the headlines.Is Stripe about to carve up the "Good Ship PayPal"

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27:40

The Death of the Subscription Box & The Rise of...

The Watson Weekly: eCommerce Strategy & News ·

2026/02/25

The "subscription box" era might be over, but the membership era is just beginning.In this episode, Rick Watson sits down with John Roman, CEO of BattlBox, to pull back the curtain on how they survived the collapse of the 2015 subscription craze to become a powerhouse in the outdoor and survival space. John shares the unfiltered truth about why he prefers the term' membership' over 'subscription box,' and how shifting the focus to community and content saved their business. We dive deep into their

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13:35

February 23rd, 2026: Stripe’s $140 Billion Question,...

The Watson Weekly: eCommerce Strategy & News ·

2026/02/23

Today on our show:Stripe’s $140 Billion QuestionWhy Temu is the New Cross-Border StandardThe UPS $150k Exit: Strategic Rightsizing or a Teamster Trap?Is Agentic Commerce a Nothingburger? The Agentic Debate Series, presented by Logicbroker.- and finally, The Investor Minute, which contains 5 items this week from the world of venture capital, acquisitions, and IPOs.Today's episode is sponsored by

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26:28

She Broke The Saks Global Saga

The Watson Weekly: eCommerce Strategy & News ·

2026/02/20

This week on the Watson Weekly Weekend edition, Rick Watson and Jessica Lesesky are breaking down a massive shift in the retail and tech landscape. From the dramatic fall of a luxury giant to Walmart's historic milestone and the high-stakes risks facing Silicon Valley’s finest, we’ve got the insights you need to stay ahead.In This Episode🎭 As the House of Luxury Turns: The Saks Global SagaWe track the "episodic drama" of Saks Global’s decline, from unpaid vendors and empty shelves to the January

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26:41

Mythbusting AI: Why SaaS Isn't Dead and Your Job...

The Watson Weekly: eCommerce Strategy & News ·

2026/02/18

Is SaaS really dead? Will AI take your job next year? In this Watson Weekly Interview, Rick Watson talks with Dr. Daniel Hulme, Chief AI Officer at WPP and CEO of Satalia, to debunk the biggest myths surrounding Artificial Intelligence. From the changing architecture of software to the rise of "Economic Singularity," Dr. Hulme provides a masterclass on how businesses and individuals can navigate the rapidly evolving tech landscape.We dive deep into:The Future of SaaS: Why LLMs are amplifying—not

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15:54

February 16th, 2026: Amazon is a Vertically...

The Watson Weekly: eCommerce Strategy & News ·

2026/02/16

Today on our show:Amazon is a Vertically Integrated UtilityShopify Fiscal Year 2025 Earnings: a Pony with One Great Trick, Could it Be More?Kroger Opens a New MarketplacePaypal Earnings and David Marcus- and finally, The Investor Minute, which contains 5 items this week from the world of venture capital, acquisitions, and IPOs.Today's episode is sponsored by Mirakl.https://www.watsonweekly.com/https://www.youtube.com/@WatsonWeeklyhttps://www.rmwcommerce.com/ecommerce-podcast-watsonweekly

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23:09

Shopify: It’s Always Been About the Checkout and...

The Watson Weekly: eCommerce Strategy & News ·

2026/02/13

Welcome to the Watson Weekly Weekend Edition. Hosts Rick Watson and Jessica Lesesky dive into the post-Super Bowl landscape to break down the biggest moves in retail, tech, and AI. From the high-stakes world of $7 million for 30 second ads at the big game to the massive earnings reports from industry titans (hello Amazon), we’re unpacking what these shifts mean for the future of commerce.In This Episode:The AI Ad Wars: We review the ads from the big game spots from Claude (Anthropic), OpenAI, and

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24:45

Why Your Agency is Falling for the AI Trap

The Watson Weekly: eCommerce Strategy & News ·

2026/02/11

In this episode, host Rick Watson is joined by Mark Rubin, CEO of Kasama, to cut through the noise of the current agency landscape. Mark brings decades of experience from his time at Lyons Consulting, Precision Design Studios, and Moku Collective to discuss why the "AI Gold Rush" might be a trap and why replatforming your e-commerce site might be a mistake in 2026.In this episode, we discuss:The PE Cycle: Mark’s firsthand experience with private equity acquisitions and the "ticking clock" that

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23:58

The Goliath Paradox: Why Scale is a Lie in Modern...

The Watson Weekly: eCommerce Strategy & News ·

2026/02/09

The Watson Weekly podcast, sponsored by Rithum, presents the keynote speech delivered in New York City on Sunday, January 11th, prior to the National Retail Federation Big Show. The. Watson Weekend Live at NRF Presented by Radial, keynote speech focused on "being bold in 2026.” The core idea is the "Goliath paradox," which argues that while David won, businesses often forget why Goliath lost. Rick Watson contends that the belief that "scale is safety" is a "lie," and in today's economy, the only

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23:38

Whatnot vs Traditional E-commerce: The Shift No One’s...

The Watson Weekly: eCommerce Strategy & News ·

2026/02/06

Join your Watson Weekly Weekend Edition hosts, Rick Watson and Jessica Lesesky, as they break down the biggest shifts in tech, retail, and e-commerce. From Pinterest’s AI pivot to Starbucks’ massive loyalty shakeup, we’re diving deep into the news moving the needle this week.📌 Pinterest’s AI EvolutionPinterest is cutting 15% of its workforce (approx. 700–800 roles) to go all-in on AI. We discuss whether this is a genuine transformation or a "playbook" move to appease investors as user growth

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28:17

NRF 2026 Debrief: Beyond the Buzzwords & The "Age of...

The Watson Weekly: eCommerce Strategy & News ·

2026/02/04

Is retail suffering from "buzzword fatigue"? In this 25-minute deep dive, Nick Kaplan and Rick Watson debrief the biggest themes, surprises, and reality checks from NRF 2026: Retail’s Big Show. From the noise surrounding "agentic commerce" to the practical startups actually moving the needle, we break down what brands need to know to survive the next era of retail.Key Takeaways:The Buzzword Barrier: Why brands are feeling lost in a sea of repetitive jargon and how to spot the difference between hype

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15:02

February 2nd, 2026: ChatGPT's 4% Fee Confirms...

The Watson Weekly: eCommerce Strategy & News ·

2026/02/02

Today on our show:ChatGPT's 4% Fee Confirms Marketplace EconomicsAmerican Eagle to Close Quiet Logistics BusinessUPS Releases 4Q 2025 Earnings and Provides 2026 GuidanceMeta Earnings in Superintelligence We Trust- and finally, The Investor Minute, which contains 5 items this week from the world of venture capital, acquisitions, and IPOs.Today's episode is sponsored by Rithum.https://www.rmwcommerce.com/ecommerce-podcast-watsonweekly

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26:06

The Shopify Massacre No One Wants to Talk About

The Watson Weekly: eCommerce Strategy & News ·

2026/01/30

In this Friday edition of Watson Weekly, Rick Watson and Jessica Lesesky dive into the major shifts rocking the retail and tech landscape. From Shopify’s controversial partner strategy to Apple’s "defensive sprint" into wearable AI hardware, we break down what these moves mean for the future of the industry.On this week's episode:* The Fall of Quiet Logistics: American Eagle is sunsetting its Quiet Logistics business. Rick and Jess explore why owning your own supply chain can be a "heavy burden" if

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34:32

How AI is Redefining E-commerce Support & Customer...

The Watson Weekly: eCommerce Strategy & News ·

2026/01/28

The "Growth at All Costs" era is over. Welcome to the era of Trust and AI Efficiency.In this episode of The Watson Weekly, Rick Watson sits down with Gareth Cummings, CEO of eDesk, to discuss the massive shift in how brands interact with their customers. From pioneering domain-specific language models in 2018 to navigating the rise of TikTok Shop and Agentic Commerce, Gareth shares a masterclass in staying ahead of the tech curve.Gareth Cummings is the CEO of eDesk, an AI-native customer support

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11:03

January 26th, 2026: Sam Altman Testing Ad, Lowes to...

The Watson Weekly: eCommerce Strategy & News ·

2026/01/26

Today on our show:Sam Altman Testing AdLowes to license its checkoutAI meets Davos and a Jassy SightingClaude Code Is Having a Viral Moment- and finally, The Investor Minute, which contains 3 items this week from the world of venture capital, acquisitions, and IPOs.Today's episode is sponsored by Rithum.https://www.rmwcommerce.com/ecommerce-podcast-watsonweeklyThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp

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25:28

From Playbooks to Pipelines: How DigitalGenius Is...

The Watson Weekly: eCommerce Strategy & News ·

2026/01/21

Most AI pilots fail—at least, that’s the headline. But today’s guest is proving that doesn’t have to be true.In this Watson Weekly interview, Rick Watson goes behind the scenes with Chris Kellner, CEO of DigitalGenius, to discuss how a decade-old AI pioneer is navigating the modern LLM explosion. We move past the hype to explore how AI is actually rewriting the playbooks for sales, marketing, and customer support.In this episode, you’ll learn:* The "Locomotive" Metaphor: Why DigitalGenius didn't

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10:52

January 19th, 2026: Walmart Shakes Up Its Leadership...

The Watson Weekly: eCommerce Strategy & News ·

2026/01/19

Today on our show:Walmart Shakes Up Its Leadership RanksNRF 2026 RecapMore Content Coming To You from the Watson Weekly- and finally, The Investor Minute which contains 4 items this week from the world of venture capital, acquisitions, and IPOs.Today's episode is sponsored by Rithum.https://www.rmwcommerce.com/ecommerce-podcast-watsonweeklyThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp

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05:22

January 12th, 2026: It’s Time to Be Bold in 2026 and...

The Watson Weekly: eCommerce Strategy & News ·

2026/01/12

Today on our show:It’s Time to Be Bold in 2026Welcome to NRF- and finally, The Investor Minute which contains 5 items this week from the world of venture capital, acquisitions, and IPOs.Today's episode is sponsored by Rithum.https://www.rmwcommerce.com/ecommerce-podcast-watsonweeklyThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp

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01:32

December 19th, 2025: Thank You!

The Watson Weekly: eCommerce Strategy & News ·

2025/12/22

Today on our show it’s no news, just thank yous.It’s been a roller coaster of a year for everyone, and despite everything, you have tuned in. Walking your dog, on the way to work, even in the shower you were there. Listening, laughing, cringing, and hopefully, even learning.I started this podcast back in 2021 and look forward to doing it for many more years. The fact that our content and presence continue to grow each year is a testament to you.So, here it is. Thank you for listening. If you

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15:27

December 15th, 2025: Shopify Winter Editions 2025...

The Watson Weekly: eCommerce Strategy & News ·

2025/12/16

Today on our show:Shopify Winter Editions 2025 Special Podcast- and finally, The Investor Minute which contains 5 items this week from the world of venture capital, acquisitions, and IPOs.Today's episode is sponsored by Mirakl.https://www.rmwcommerce.com/ecommerce-podcast-watsonweeklyThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp

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