The Watson Weekly: eCommerce Strategy & News

Watson Weekly
  • 4.9 (36)
  • Management
  • Updated Weekly

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 interviews with C-Suite luminaries and tech innovators. Fridays: Join the Watson Weekend for Spirited debates on controversial topics with co-host Jessica Lesesky. From AI implementation and marketplace dynamics to supply chain logistics and retail operations, we cover the entire commerce landscape. Whether you are a CEO, VP, or operator, this is your competitive advantage in audio form.

  1. 3d ago

    Starbucks Is Spending $1.2B on Comfier Seats. Rick Wants Better Coffee

    Rick thinks Starbucks has lost its way. Jess thinks Brian Niccol’s turnaround is working, and she points to four straight quarters of growth. Niccol has put handwritten Sharpie names back on cups and is spending $1.2 billion to make stores more comfortable. Rick says a better seat means nothing when you wait 25 minutes for burnt coffee. Jess says consistency matters more than quality, and that cake pops and pink drinks keep parents and Gen Alpha coming back. Rick asks whether Starbucks should accept being the McDonald’s of coffee or go upscale with Starbucks Reserve. He also floats a Yum Brands-style parent company that buys other chains. Jess wonders if it needs a Krispy Kreme to take on Dunkin’. Rick calls Niccol’s six-point strategy a zero-point plan. He thinks the board could push Niccol out before they cover Starbucks again. Watson Weekly Newsletter at watsonweekly.com

  2. 4d ago

    Keith Pires of Boldest on AI sales agents and the Shopware MCP

    Keith Pires is CRO and co-founder of Boldest, an agency built on top of an agent platform called Pathfinder. Vinny O’Brien caught up with him at Shoptoberfest in Nashville, shortly after both of them came off the mechanical bull. Pires says his co-founder and CTO, Ramy Youssef, has been developing Pathfinder for many years with a team based in Egypt. He describes it as the foundation of the agency. Boldest owns the environment, and Pires agrees that settles most of the governance and security questions clients bring. The clearest example is a sales agent Boldest built for Delectable, a B2B SaaS client. Pires says it was trained on the product and on a structured sales method. It sorts each visitor into a buyer type, such as economic or technical, and scores them on the questions they ask. When it’s ready, it books a meeting in Calendly without a person stepping in. Pires talks through the Shopware MCP integration and why that build was hard. He describes mood boards and a persistent wardrobe feature that Boldest is exploring with a fashion marketplace client, and he explains how far apart clients are on AI, with some fully bought in and others worried about where their data goes. Pires expects agents to get good enough that shoppers can’t tell them apart from people. He didn’t say whether shoppers would be told. Keith Pires will be speaking at the Agentic Commerce Virtual Summit on October 29, 2026. Register here: https://streamyard.com/watch/W5CF8XC8xJCs

  3. 5d ago

    A Mattress Brand Grew 68% in July While the Category Shrank

    Naturepedic has made organic mattresses for years. Its three owners are engineers, and the marketing used to read like their spec sheets. Arin Schultz, the chief growth officer, changed the messaging before anyone approved it. He says sales were up 46% in May and close to 68% in July, and he puts the mattress category down by double digits over the same period. Arin runs sales and marketing as one job. He tells Rick why he goes after shoppers who have never heard of Naturepedic and don’t care about organic, and why he treats a 5% growth year as a failure. Most of the conversation is about stores. Naturepedic picks sites from where its website traffic is concentrated, and Arin says a new store lifts digital sales nearby by 10 to 15%. Eight more open by January and up to ten more next year, toward a limit he sets at 50 to 70 locations. He also explains why the brand stays off paid top-10 mattress lists, and why he won’t take Meta’s or Google’s attribution at face value and runs three tools against each other instead. Sonal Gandhi of The Lead joins too. She named Arin to this year’s Direct 60 list. #watsonweekly #naturepedic #thelead #dtc #retail #mattress #casper

  4. Oct 12

    C.H. Robinson Pays More Than 40x EBITDA for RXO

    C.H. Robinson is paying $5.8 billion in cash and stock for RXO, which Rick works out to more than 40 times RXO’s expected adjusted EBITDA for this year. The deal deck brings that down to about 13 times, but only by counting $300 million in cost savings that haven’t happened yet. Retail and e-commerce make up 37% of RXO’s revenue. Also this week, ChatGPT adds virtual try-on to its shopping results, and Rick still can’t see how features like this pay back what OpenAI’s investors have put in. Apple’s iOS 27 shipped with a Safari block list that includes The Trade Desk, LiveRamp, ID5 and Permutive, though retail media networks with logged-in shoppers are left alone. Target’s holiday app can now scan a kid’s handwritten wish list and share it with relatives, which could become a Roundel opportunity. Shopify launched Canvas. It says a merchant can now build a custom store in twenty minutes. IDC’s Heather Hershey estimates Shopify took 21.8% of a $13.4 billion commerce software market in 2025, while Salesforce shrank. In the Investor Minute, Uber buys ezCater for $2.3 billion in cash, and Rick covers a few smaller deals. Rick is moderating the Shopware agentic commerce virtual summit on October 29. Register at watsonweekly.com/events. #watsonweekly #shopify #openai #apple #target #ecommerce #retailmedia #uber

  5. Oct 9

    Costco Runs its Own Chicken Plant in Nebraska to Keep a $4.99 Loss Leader Going

    Costco’s sales rose 11.2% last quarter, and Rick Watson and Jessica Lesesky talk through where that growth is coming from. Costco says members under 40 now make up more than a quarter of the base. Many of them live in apartments and order on their phones, and Costco says delivery orders arrive in under an hour on average. Rick joined recently and bought a mattress there. Jess isn’t a member because she has nowhere to store bulk paper towels. They get into the executive membership tier, the $4.99 rotisserie chicken Costco supplies from its own Nebraska plant, the $1.50 hot dog, and the return of churros. The second half covers a proposed class action over tariff refunds, filed by an Illinois member who wants the money paid back to shoppers. Costco booked a one-time gain from refunds this quarter and says it put part of that into lower prices, including on coffee and pepper. Jess thinks Costco handled it better than other retailers did, while Rick suspects some of it went to shareholders. #Costco #CostcoEarnings #RetailEarnings #Retail #WarehouseClub #TariffRefunds #Millennials #GenZ #RotisserieChicken #KirklandSignature #WatsonWeekly

  6. Oct 7

    Tom McFadyen's AI Commerce Book Went From 125 Use Cases to 500

    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 studies alongside it, and McFadyen made the whole thing free at ai-best-practices.com. Agentic commerce gets most of the attention right now. Tom points out that retailers have run AI on recommendations and fulfillment for years, and plenty of the newer agentic work sits in catalog enrichment and merchandising, well before a shopper reaches checkout. We also talk about who the book is for, including the B2B distributors and manufacturers that make up much of McFadyen's client base. Tom will let an agent reorder the socks he's bought on Amazon for decades. He doesn't expect his wife to let one pick her dress for a wedding. Most of what retailers sell falls somewhere between those two. #WatsonWeekly #AgenticCommerce #RetailAI #B2BCommerce #Marketplaces #RetailClub #McFadyenDigital

  7. Oct 5

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

    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 high as $15 billion. OpenAI has said it won't list in 2026. Reuters reported on Anthropic's prospectus, which shows $4.6 billion in revenue last year and about $518 billion in cloud and infrastructure commitments. Two customers made up nearly a quarter of that revenue, and many large clients aren't on long-term contracts. Amazon asked Meta to take Amazon out of Muse, Meta's new shopping agent, while Amazon's own Buy For Me feature lists brands' products without asking them first. Brand Finance puts $73 billion of food brand value at risk from GLP-1 drugs, with Lay's the most exposed at $6.88 billion, though Rick gives more weight to Cornell's basket data showing a 6% drop in grocery spending in households using the drugs. Amazon also signed a long-term freight deal with Kuehne+Nagel that covers AWS data center logistics and includes a call option on Kuehne+Nagel shares vesting over up to seven years. Investor Minute: Jolly acquires Rye. Infillion acquires Foursquare. Numeral raises $100M in Series C funding. Overfuel raises $6M. Databricks acquires Row Zero. Rick is moderating Shopware's Agentic Commerce Virtual Summit on October 29. Register at watsonweekly.com/events. Newsletter and past episodes at watsonweekly.com. #Amazon #AgenticCommerce #Anthropic #GLP1 #CPG #Shopify #WatsonWeekly

  8. Oct 2

    Amazon Blocks AI Shopping Agents as Oreos Climb From 10% to 70%

    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 handing any agent your cards. Shopify and Walmart are going the other direction, though nobody is reporting what Walmart actually sells inside ChatGPT. They also cover who is on the hook when an agent buys something it shouldn't have, and what happens to retail media, a $170B business last year, when the shopper reading the page is a bot that never sees an ad. The back half is about Oreos. Mondelez found its cookies came up in about 10% of AI cookie recommendations, brought in AEO and GEO firms, and now shows up around 70% of the time according to the Goldman research. Rick and Jess also disagree on whether you separate the cookie before eating it. For brands that aren't showing up in agent results, part of the fix is technical work on their own sites, and some are blocking agents they don't know about. This episode is sponsored by Avalara.

See All (300)

4.9
out of 5
36 Ratings

About

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 interviews with C-Suite luminaries and tech innovators. Fridays: Join the Watson Weekend for Spirited debates on controversial topics with co-host Jessica Lesesky. From AI implementation and marketplace dynamics to supply chain logistics and retail operations, we cover the entire commerce landscape. Whether you are a CEO, VP, or operator, this is your competitive advantage in audio form.

Information

You Might Also Like