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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

01:14:13

Ads in ChatGPT? AI Agents Buying for You? Three...

The Watson Weekly: eCommerce Strategy & News ·

2026/04/15

The Agentic Debate Series Lunch @ Shoptalk Las Vegas 2026, Presented by Logicbroker. Recorded live in Las Vegas on March 24, 2026. Rick Watson hosts an agentic commerce debate with three retail practitioners who aren't selling anything — just calling it like they see it.Chris Silver (CTO, JustFood for Dogs), Gina Lombardo (VP of Digital, Retrofête), and Dave Finnegan (Managing Director, BlackFinn Partners) go head-to-head on three questions the entire industry is dancing around:Will ads ever work

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12:30

April 13th, 2026: Amazon USPS Deal, New BNPL Data,...

The Watson Weekly: eCommerce Strategy & News ·

2026/04/13

Amazon cuts USPS volume, BNPL shapes where Gen Z gets their teeth cleaned, and why your product data is now an AI infrastructure problem.This Watson Weekly episode covers: The Amazon-USPS tentative deal and what a 20% volume reduction actually signals about Amazon's logistics endgame. The Watson Weekly is sponsored by Avalara - the agentic AI platform automating global tax and compliance for leading eCommerce brands. For more details: https://avalaratax.watsonweekly.comNew April 2026 data on Buy Now

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18:56

What Does a $99 Lowe's Subscription, 60% Returns, and...

The Watson Weekly: eCommerce Strategy & News ·

2026/04/10

Rick Watson and Jessica Lesesky break down three retail stories that challenge conventional wisdom this week.Revolve runs a 60% return rate — triple the online average — and just posted a 60% profit surge. They explain how baking return costs into margins and offering frictionless two-day shipping produces 80% full-price sell-through and a customer base that treats their bedroom like a fitting room. Physical storefronts in Aspen and LA are next.The Watson Weekly Weekend edition is sponsored by

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12:41

April 6th, 2026: Shopify's Partner Town Hall, Lowe’s...

The Watson Weekly: eCommerce Strategy & News ·

2026/04/06

Rick Watson breaks down four stories shaping e-commerce and retail this week: Shopify's partner town hall reveals a company that treats API chaos as a brand attribute — and why that's a problem for any hyperscaler ambition. Lowe's bets $99 can put a red vest inside your home twice a year, and why that physical touchpoint is worth more than any app can replicate. The Watson Weekly is sponsored by Avalara — automated tax compliance built for Shopify merchants, from calculation to returns. For more

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27:04

Apple at 50, Amazon's Robot Bet, and How Allbirds...

The Watson Weekly: eCommerce Strategy & News ·

2026/04/03

Apple just turned 50. Amazon quietly acquired two robotics companies. And Allbirds — once valued at $4B— sold for $39M. Rick Watson and Nick Kaplan work through what these three stories have in common: the relentless pressure to find a next act before the first one runs out.The Watson Weekly Weekend edition is sponsored by Avalara — automated tax compliance built for Shopify merchants, from calculation to returns. For more details: https://avalara.watsonweekly.com/Topics this week: whether Tim

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14:31

I Read Rick Watson's Research Prompts and Used Them...

The Watson Weekly: eCommerce Strategy & News ·

2026/04/01

Rick Watson is out. Nick Kaplan is in — and he's not giving the mic back.In this special Kaplan Wednesday episode, Nick takes the research prompts Watson built for his agentic commerce analysis and turns them on the very stories they were designed to interrogate.On the docket: Adyen's white paper claiming infrastructure is the constraint on agentic commerce (it isn't — and their own 95% AML false positive rate says why). Shopify's one-toggle Agentic Storefront promise and the data ownership problem

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28:58

Shoptalk 2026: The Agentic Fog and the Retail Advice...

The Watson Weekly: eCommerce Strategy & News ·

2026/03/27

LivefromthechaosofShoptalk2026—whereeveryboothpromisedanAIfutureandthefloorprovedretailisstillfundamentallyacontractualpromisetoacustomer.Retailande-commerceinfluencerRickWatsonisoutonassignmentinLasVegas.Thisepisodecutsthroughtheagenticcommercenoise.WegetintowhatAEO(AgenticCommerceOptimization)actuallyrequiresoperationally,whyShopifycontinuestoeatthemarketwhilefacingreallimitsatenterprisescale,andwhattheStripe-Shopifyrelationshiptellsyouaboutwherepaymentsinfrastructureisheading.TheWatsonWeekendisspo

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28:36

The AI Double Standard — Why Brands Fear AI Mistakes...

The Watson Weekly: eCommerce Strategy & News ·

2026/03/25

Darren Heaphy has spent his career at the intersection of e-commerce and logistics — AOL, Scurry, and now eDesk, where he leads product. His take on AI-driven support is blunt: brands are holding AI to a standard they never applied to their seasonal hires, and that double standard is costing them.In this episode, Rick Watson interviews and discusses the real shift happening in customer support — not chatbots replacing agents, but human teams moving from execution to orchestration. Darren calls it

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13:27

March 23rd, 2026: The Shoptalk Edition

The Watson Weekly: eCommerce Strategy & News ·

2026/03/23

Rick Watson breaks down four stories worth your attention before Shoptalk.OpenAI's internal "code red" and what a pivot to enterprise and coding revenue actually signals ahead of a potential IPO; Dollar General and Dollar Tree earnings — both beating expectations, but with very different stories underneath the numbers; Apollo's credit chief calling private equity valuations "literally fiction," and why that matters for tech-focused PE portfolios still carrying COVID-era marks; and the three

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24:31

Dollar Stores Win, Prime Day Jumps the Calendar, and...

The Watson Weekly: eCommerce Strategy & News ·

2026/03/20

Dollar stores are quietly winning, Prime Day is jumping the calendar, and the AI arms race just hit its first major reboot. Rick Watson and Jessica Lesesky break down what actually moved this week in retail and commerce.Dollar General doubled its operating profit, Dollar Tree shed Family Dollar and beat estimates, and Five Below kept growing — while 99 Cents Only filed for bankruptcy. The value shift is real, and it's not just low-income shoppers driving it.Amazon is moving Prime Day to June. Is

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25:23

Why Most AI Projects Are Failing — And What to Do...

The Watson Weekly: eCommerce Strategy & News ·

2026/03/18

Tom Schmitt is CEO of Radial, North America's largest third-party fulfillment provider — and a company about to become something bigger. As part of the Bpostgroup's rebranding to Paxon, Radial is merging with its sister companies into a single global logistics brand built on decades of e-commerce infrastructure.The Watson Weekly is sponsored by Avalara. For more information on Avalara, visit - https://avalara.watsonweekly.com/Tom sat down with Rick Watson to talk about what he's actually seeing on

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10:45

March 16th, 2026: Stripe’s Agentic Suite, Salesforce...

The Watson Weekly: eCommerce Strategy & News ·

2026/03/16

Stripe just released an Agentic Technology Suite and positioned it as the infrastructure layer for the next era of commerce.]So who is Stripe actually building this for?The Watson Weekly Interview is sponsored by Avalara. For more information on Avalara, visit - https://avalara.watsonweekly.com/Salesforce Marketing Cloud posted -1% growth in Q4 FY2026 — the end of four years of deceleration and the start of something worse. Rebranding to Agentforce doesn't fix a product growth problem, and

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24:19

Analyzing Dick’s App Success, Nike’s Strategy, and...

The Watson Weekly: eCommerce Strategy & News ·

2026/03/13

In this week’s Watson Weekly weekend edition, hosts Rick Watson and Jessica Lesesky talk about Dick’s Sporting Goods' viral Move moment, Elliott Hill in the New York Times, and the gap between consumer spending at Amazon and Walmart. Dick's Sporting Goods is number three in the App Store. Nike is running a PR campaign dressed as a turnaround. And the consumer spending data has already picked the winners of the next decade of retail — most people just aren't reading it correctly.The Watson Weekend

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40:28

From 50% to 95% AI Adoption: How Mirakl's Chief Data...

The Watson Weekly: eCommerce Strategy & News ·

2026/03/11

What does it actually take to go from AI experimentation to real business impact? In this episode of the Watson Weekly, Rick Watson sits down with Anne-Claire Baschet, Chief Data and AI Officer at Mirakl — the enterprise marketplace platform powering some of the world's largest retail brands.Anne-Claire shares how she went from a passion for sci-fi and mathematics to leading AI transformation at scale — spanning French national rail, a refurbished car marketplace IPO, and now a bold mandate at

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13:40

March 9th, 2026: Shopify Middleware? Stripe Letter, ...

The Watson Weekly: eCommerce Strategy & News ·

2026/03/09

The AI shopping revolution is here — but who actually controls it? In this week's Watson Weekly, Rick Watson breaks down four stories reshaping the future of e-commerce.The Watson Weekly is sponsored by Avalara. For more information on Avalara visit - https://www.avalara.watsonweekly.com/🛒 Shopify vs. AI Agents — Shopify is making a bold bet: positioning itself as the back office of record for the agentic web. But if LLMs keep getting smarter, does the middleware even survive? Rick walks through

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22:22

Who Is Really Winning Between OpenAI and Amazon?

The Watson Weekly: eCommerce Strategy & News ·

2026/03/06

Welcome to this weekend edition of Watson Weekly with Rick Watson and Jessica Lesesky! Today, we’re breaking down the biggest moves in retail and e-commerce from the past week..We start with Target’s latest earnings, where a 1.7% dip in net sales has triggered a major turnaround strategy focused on beauty, food, and the Target Circle 360 premium membership. Then, we dive into Shopify’s investor event to discuss Agentic Commerce—is AI the new front door for online shopping? Finally, we analyze the

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26:08

The Retail Earnings Breakdown: Who’s Winning 2026?

The Watson Weekly: eCommerce Strategy & News ·

2026/03/04

The dust has settled on Q4 and full-year 2025, and the numbers tell a fascinating story about the future of how we buy, ship, and sell. From Amazon’s record-breaking AWS growth to Walmart laying down the gauntlet, we are diving deep into the ripple effects these giants are creating across the entire ecosystem.In this episode, Rick Watson breaks down the split personalities of Meta, the agentic jump ball between Shopify and Stripe, and why UPS finds itself in an incredibly tight spot between Amazon

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12:54

March 2nd, 2026: Walmart Continues Its Tear: eCom...

The Watson Weekly: eCommerce Strategy & News ·

2026/03/02

Today on our show:Walmart Continues Its Tear: eCom Growth at 27%Perplexity Abandons Advertising to Maintain User TrustThe Great Parcel Reconfiguration No One is Talking AboutAbout That 2028 Global Intelligence Crisis- 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/@WatsonWeekly

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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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