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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

05:21

Tom McFadyen's AI Commerce Book Went From 125 Use...

The Watson Weekly: eCommerce Strategy & News ·

2026/10/07

Tom McFadyen has spent decades building marketplaces and commerce platforms at McFadyen Digital. His firm's new book, AI Best Practices for Commerce, runs more than 500 pages in print, and Tom says the printed version couldn't keep pace with how fast the material changed.I caught up with Tom at Retail Club. The book launched with 125 AI use cases, sorted into four phases of commerce that McFadyen calls market, sell, fulfill and support. Online, that count is now past 500, with several hundred case

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13:18

Anthropic Has $518B in Compute Bills and $4.6B in...

The Watson Weekly: eCommerce Strategy & News ·

2026/10/05

Amazon now lets US sellers run their eBay, Shopify, TikTok and Walmart sales inside Seller Central, free of charge. Amazon says more than 95% of its independent sellers already sell elsewhere, and each of those outside orders now sits next to an Amazon shipping button. Rick Watson thinks most sellers will be reluctant to put their Walmart numbers inside Amazon's software.Oura postponed its NASDAQ debut the day before it was due to price, after planning to raise up to $2.2 billion at a valuation as

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08:59

Amazon Blocks AI Shopping Agents as Oreos Climb From...

The Watson Weekly: eCommerce Strategy & News ·

2026/10/02

Amazon is blocking nearly every AI shopping agent, starting with Perplexity. Rick Watson and Jessica Lesesky go through Goldman Sachs' 64-page report on agentic commerce, which opens on Amazon's blocking and includes a section on agent liability that is labeled TBD.Rick reads the blocking as a negotiating position, the same move Amazon made with Buy With Prime and Shopify. Jess thinks Amazon is right to keep agents out and points to Meta's record on account security as a reason to be careful about

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27:55

Your Data Lake Won't Make You AI-Ready

The Watson Weekly: eCommerce Strategy & News ·

2026/09/30

Every retailer wants AI agents, and very few have data an agent can use. Abhi Sachdeva, co-founder and CTO of EKYAM, has spent 18 of his 24 years in technology inside retail, running tech at 1-800-Flowers, Tory Burch and QVC. He joins Rick to explain what data readiness requires and where retailers keep getting it wrong.A data lake stores rows. It doesn't tell an agent what those rows mean or which system to trust, so the agent picks up the first answer it finds and presents it with full confidence

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01:45

Amazon Wants to Handle Agent Payments While Blocking...

The Watson Weekly: eCommerce Strategy & News ·

2026/09/25

Rick Watson reports from the Retail Club AI event in Huntington Beach, which he's calling the source of the agentic fog he first described at Shoptalk. This is the second stop in the on-location series that started there.It's hot, there isn't much shade, and lunch is small portions from a handful of food trucks. The talks are better. More presenters are now separating the places where AI fits from the places where it doesn't, and Rick says the startup alley has been the strongest part of the

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27:33

Hairstory Collected Tax It Never Remitted, Then Fixed It

The Watson Weekly: eCommerce Strategy & News ·

2026/09/23

Hairstory launched at the end of 2015 selling online to consumers and hairdressers across the US. It collected sales tax from launch but registered in only a handful of states, so for about a year the tax it owed everywhere else sat in a separate bank account and kept growing. Catching up, even with Avalara's help, took months of pulling order-level data for each state's forms, work that fell largely to cofounder Erica Halliwell, who had taken on sales tax with no background in it and says it left

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13:23

Amazon's First Price Rate Went From 4% to Nearly 80%

The Watson Weekly: eCommerce Strategy & News ·

2026/09/21

The FTC says Amazon ran an ad auction, got an answer, then replaced it with a higher price it set itself. The complaint landed in Seattle on August 31 with 22 state attorneys general attached and runs 181 pages. The agency puts the money involved above $20 billion.Amazon answered the next day with a blog post. Average winning bids on its search ads fell 50% between 2019 and 2025, it said, while the inflation-adjusted price advertisers actually paid held flat. Both figures are Amazon's own. A 50%

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07:49

Amazon Isn't Your Friend. The FTC Says It Overcharged...

The Watson Weekly: eCommerce Strategy & News ·

2026/09/18

The FTC and 22 state attorneys general are suing Amazon over its ad auctions. They say an undisclosed soft reserve pushed up what 1.2 million advertisers paid and cost them more than $20 billion since 2019. Amazon says CPCs stayed flat after inflation, conversion went up, and nobody was harmed.Rick Watson and Jessica Lesesky go through the complaint, Amazon's same-day rebuttal and its Genesis-style blog post, why Chair Andrew Ferguson picked this fight in a midterm year, and what Amazon's struggle

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32:59

How to Buy AI Agents Without Getting Stuck on One Model

The Watson Weekly: eCommerce Strategy & News ·

2026/09/16

Every CIO has been told to invest in agentic AI. Nobody has told them how much to spend or when.Shawn Mandel is working through that decision right now as CTO of Dentalcorp, which supports more than 650 dental practices across Canada and, since July, the US. He joins Rick Watson for a Watson Weekly webinar on technology decisions in the agentic era, alongside Jason Cottrell, founder and CEO of Orium and president of the MACH Alliance, and Anatolii Iakimets, director of product marketing at

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13:36

Costco Said Next Was Growing, Then Deleted It Over a...

The Watson Weekly: eCommerce Strategy & News ·

2026/09/15

Dollar Tree's everyday basics grew almost 6% last quarter. The discretionary side, toys and seasonal and party goods, grew under 2%. Dollar Tree and Dollar General reported the same day, and both chief executives worked hard to tell analysts the spread doesn't mean what you think it means. Dollar General credits its share gains to households making over $100,000 a year and raised full year guidance. Rick's read is that a retailer winning because the economy is bad has borrowed the quarter and pays

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09:10

Let the AI Agents Do the Shopping So They Don't Kill...

The Watson Weekly: eCommerce Strategy & News ·

2026/09/11

Anthropic has moved into commerce. On September 2 it put an open-source blueprint on GitHub for building a shopping agent and a merchant agent on Claude, with demo builds for retail, travel, telecom and ticketing. Rick Watson and Jessica Lesesky have about 50 years of e-commerce experience between them. By their count, the co-authors behind Anthropic's commerce memos add up to roughly four.Anthropic says pilot customers saw carts up to 35% larger and 60% more completed purchases. Jess notes there's

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30:26

The Middle Miles Are Where B2B Money Is, with Andy Hoar

The Watson Weekly: eCommerce Strategy & News ·

2026/09/09

Andy Hoar thinks the industry is fighting over the wrong ground. The storefront and the last mile get the budget because those are the parts a customer can see. Andy's case is that in B2B the money sits in the middle miles, the stretch between the click and the dock where pricing gets calculated, inventory gets allocated and orders get tracked. Bots are already good at that work, in part because the buyer never sees it and doesn't much care how the result arrived.Andy cofounded MasterB2B, wrote

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14:24

Walmart Got $2.9B Back And Won't Say What Reached The...

The Watson Weekly: eCommerce Strategy & News ·

2026/09/07

Retail's second quarter doesn't compare to anything, and the reason is a refund.In February the Supreme Court ruled that the emergency powers law behind the White House tariffs never granted the authority to impose them. Importers of record filed to get the money back and it landed in Q2. Walmart was eligible for roughly $2.9 billion. Home Depot took $730 million. Target booked a $994 million pre-tax benefit. TJX got $331 million, Kohl's $100 million, Lowe's about $80 million.That put a private

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08:41

Walmart's 11K Rollbacks and Who Actually Pays for Them

The Watson Weekly: eCommerce Strategy & News ·

2026/09/04

Walmart ran 11,000 rollbacks last quarter, roughly double the same period a year ago, and the money paying for them comes from a business most of its competitors don't have. Advertising and membership now account for about a third of Walmart's operating income and grew 38% in the quarter. Rick Watson and Jessica Lesesky go through what that does to everyone on the other side of the table: suppliers facing another round of concession requests, grocers without a profit pool deep enough to fund a price

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26:21

The CFO Who Didn't Care About a 35% Return Rate

The Watson Weekly: eCommerce Strategy & News ·

2026/09/02

Kyle Bertin thinks the industry has the returns conversation backwards. His company, Two Boxes, builds software for the section of the fulfillment center nobody wants to walk into, and his argument is that returns are an inventory management problem. He calls it the least optimized inventory pool most merchants own.The math he runs uses a hypothetical $100 million apparel brand. A 25% return rate sends $25 million of GMV back through the door, and at the 50% restock rate he sees in unoptimized

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23:26

Three Years In, We Finally Ranked the Stores We...

The Watson Weekly: eCommerce Strategy & News ·

2026/09/01

Three years of the Watson Weekly, and Rick Watson and Jessica Lesesky mark it by doing the one thing a retail show almost never does on air: putting a grade next to the stores they actually shop.It is a tier list. S through C, live, no rubric shown to the audience. Alo Yoga takes the only S, on a hundred-plus stores, international expansion into London and Korea, and a King Street address in Charleston sitting between Skims and Gucci. Rick admits he was a hater first. Amazon lands at A on the

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12:39

Tariff Refund Quarter: Walmart's 28.8%, Target's...

The Watson Weekly: eCommerce Strategy & News ·

2026/08/31

Walmart collected about $2.9 billion in tariff refunds and spent it on roughly 11,000 rollbacks in Walmart US. Transactions grew and operating income rose 28.8%. The comp still slowed to 2.6% excluding fuel, the weakest quarter since 2020, with the softness concentrated in lower-income households. Walmart raised full-year guidance on the assumption that the second half improves on the back of that price investment, which puts a refund that will not repeat into the base of next year's math.Lowe's

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10:23

Google Buys a Dead Airline's Data, Mom Outranks...

The Watson Weekly: eCommerce Strategy & News ·

2026/08/24

Spirit shut down on May 2 with roughly $8.1 billion in debt and about 17,000 people out of work, and the estate has been selling the pieces since. A court approved 22 LaGuardia slots to JetBlue for $58.5 million in July. Last week's lot was the data. The August 14 notice out of the Southern District of New York itemizes 100 million emails, 500 million Microsoft Teams chats, around 30 million lines of code, pricing from 7.2 billion competitor flights, 7.5 billion passenger transaction records going

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08:15

Stripe wanting PayPal says more about Stripe than...

The Watson Weekly: eCommerce Strategy & News ·

2026/08/21

Rick Watson and Jessica Lesesky work through the reported talks, and Rick lands firmly on the skeptical side. Stripe grows around 34% a year by the hosts' count, throws off billions in cash flow, and has spent years buying up pieces of the stack, including Indie Hackers, Payable, Index, and Lemon Squeezy. It runs in stablecoins, crypto, and AI routing. The one thing missing is a consumer relationship, which is what PayPal and especially Venmo are supposed to supply. Jessica's counterpoint is that

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35:41

The B2B Order Management Problem Distributors Don't...

The Watson Weekly: eCommerce Strategy & News ·

2026/08/19

The storefront stopped being the differentiator. Kibo CEO Ram Venkataraman argues the money and the difficulty both moved to order management, and that most B2B distributors have an OMS problem they have no name for.Rick opens on accountability. An autonomous agent takes an order, routes it to the wrong warehouse, approves a return it shouldn't have. Who owns that outcome? Ram says shoppers will blame the retailer every time, and the burden falls on vendors to build systems that earn the retailer's

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