May 18th, 2026: Amazon Now Goes Live, eBay Says No to GameStop, and OpenAI Bets $14B on Enterprise

The Watson Weekly for May 18, 2026. Amazon launched a 30-minute delivery to take on DoorDash. eBay shuts down GameStop's bid. OpenAI puts $14 billion behind an enterprise AI play. The Watson Weekly is sponsored by Avalara. For ecommerce brands, tax compliance gets more complicated with every new channel, state, product, and market. Avalara Agentic Tax and Compliance helps automate the work behind the scenes, so merchants can deliver a smoother customer experience — with accurate tax calculation at checkout, clearer visibility into tariffs and duties, and fewer surprises for customers when their order arrives.Avalara works with ecommerce platforms like Shopify, BigCommerce, WooCommerce, and more, helping teams manage compliance faster and scale with more confidence. To learn more about Avalara’s ecommerce compliance solutions, and explore resources built for growing ecommerce brands go to avalara.watsonweekly.com for more details.Amazon Now is live. Thirty-minute delivery for groceries and household essentials, starting in Atlanta, Dallas, Fort Worth, Philadelphia, and Seattle, with seven more cities queued up. Prime members pay $3.99 an order. Non-Prime pays $13.99. The strategy is direct. Smaller fulfillment centers in residential zones, aimed straight at DoorDash, Uber Eats, and Instacart.eBay's board said no to GameStop. Chairman Paul Pressler called the unsolicited bid "neither credible nor attractive." The rejection wasn't really about price. OpenAI launched the OpenAI Deployment Company, valued at $14 billion, with $4 billion freshly raised under TPG's lead. The investor list reads like a consulting roster: McKinsey, Bain, Capgemini. The mission is forward-deployed engineers embedded inside enterprises to rebuild workflows. We also break down the Watson Weekly’s Shopify three-part June webinar series, The Big Green Bag of Promise, with operators from Stanley 1913, Reitmans, and Marine Layer talking honest numbers on enterprise migration. The webinars are not sponsored by Shopify but by Avalara, Domaine, and Pattern, Register here: https://streamyard.com/watch/ibqNx46Z88BfAnd the Investor Minute: Co-pilot Kit ($27M for an AGUI protocol), Cognizant's roughly $600M Australian acquisition, District's $14.7M seed for community marketplaces, Recharge buying Skio for $105M, and PayPal splitting into three new business units.