The Watson Weekly: eCommerce Strategy & News

Watson 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. Jul 3

    The Bold and the Cold of 2026 So Far

    Half of 2026 is behind us. We went back through the first six months and split the big commerce and AI stories into two groups, the bold moves and the cold ones. Start with Anthropic. While the attention stayed on OpenAI, it kept its head down and aimed at one customer, the enterprise buyer. The Snowflake deal landed. Opus shipped over the holidays and picked up real developer momentum. Claude Code gave those developers somewhere to work that wasn't a browser tab. That's a company that knew what it was ignoring. The Watson Weekly Weekend episode is sponsored by Avalara. Its Agentic Tax and Compliance automates behind-the-scenes work for ecommerce brands, enabling accurate checkout tax calculation, clearer tariff and duty visibility, and fewer customer surprises. Avalara integrates with platforms like Shopify, BigCommerce, and WooCommerce. Learn more at avalara.watsonweekly.com Then Ryan Cohen. He aimed GameStop at eBay, took the board's rejection on the chin, raised his stake to 7.8%, and told anyone listening he wants to own it. Gutsy. The follow-through has been weaker than the opening move. The cold list is shorter and sadder. eBay's roughly $1.2 billion deal to buy Depop from Etsy is still sitting in regulatory review, and Depop sellers are already watching boost fees jump to 12% and wondering what the integration does to the rest. eBay does not have a great record of making acquisitions work. OpenAI, for its part, backed away from checkout. Commerce has a way of humbling anyone who thinks returns, fraud, and merchant-of-record rules are somebody else's problem.

    13 min
  2. Jun 29

    June 29th, 2026: Papa John's and Instacart, Amazon Prime Day, FedEx Earnings, and Agentic Cannes

    This week on the Watson Weekly, four stories about who controls what you see and what you buy. Papa John's wanted to reach you the moment your fridge runs empty, so it bought the data to know when that happens. Instacart supplied it. The company confirms this is the first time it has handed first-party purchase data to a brand outside packaged goods, served on NBCU streaming inventory. The targeting is clever. The results do not exist yet. Amazon moved Prime Day to June for the first time since 2021. The stated reason is a crowded July. The real reason is a holiday Amazon never has to share. Adobe projected $26.3 billion in spending across the window, but CPI rose 4.2% in May and average order values fell 17%, with more shoppers reaching for buy now, pay later. Read that headline slowly. The Watson Weekly is sponsored by Avalara. It works with platforms like Shopify, BigCommerce, and WooCommerce, helping teams manage compliance faster and scale with confidence. Learn more at avalara.watsonweekly.com. FedEx grew revenue 13%. Strip out the fuel surcharge and adjusted operating income grew 3%, with margins down 70 basis points. The company spun off freight on June 1st at the bottom of its cycle and switched its fiscal calendar. The December report covers a seven-month stub year. Cannes sold agentic commerce for five days on the Riviera. Amazon launched agentic ads on Alexa. Retail media hit a number near $150 billion, according to the people selling it. Capability and intent were everywhere. Proof was not. Plus the Investor Minute: Redo, Orderful, Walmart's $1.4 billion move on Vibe, Tiger Finance and Glossier, and Bed Bath & Beyond buying a real estate platform. #watsonweekly #papajohnspizza #instacart #fedex #amazon #cannes

    15 min
5
out of 5
35 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.

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