March 9th, 2026: Shopify Middleware? Stripe Letter, Amazon-OpenAI Deal, & Thoma Bravo

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 two scenarios that every e-commerce operator needs to understand.💳 The Stripe Annual Letter — $1.9 trillion in payment volume, a "stablecoin summer," and a controversial vision for Level 5 agentic commerce (AI that buys things before you ask). Is this a consumer-friendly future or a payments provider's dream dressed up as progress?The Watson Weekly is also sponsored by Mirakl. You don't need another tool; you need a growth partner. The Mirakl platform is powering the next era of retail for brands and retailers who are ready to move, powered by AI and built for what's next.🤖 The Amazon-OpenAI $50B Deal — What it means for AWS, Nvidia, and Alexa — and the one glaring thing that's missing from the deal that tells you everything about how these negotiations really work.🚚 The Logistics Rollup — Thoma Bravo is merging Auctane (ShipStation, Stamps.com, Metapack) with WWEX Group to build an end-to-end logistics intelligence stack. Could this be the most important supply chain bet of the decade?Plus: this week's Investor Minute covers Salesforce's acquisition of Momentum, Aritzia's buy of Fred Segal, and two fresh seed rounds in supply chain tech.📬 Subscribe to Rick's newsletter: watsonweekly.com 🎙️ Find the podcast on all major platforms.#WatsonWeekly #AgenticAI #Stripe #Shopify #OpenAI #Amazon