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/ibqNx46Z88Bf

And 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.

Three retail moves worth talking about this week.

Amazon is retiring the Rufus name. The shopping chatbot has hit roughly 300M users since its 2024 beta, but Amazon is folding the whole thing into Alexa and calling it "Alexa for shopping." We get into why that branding choice is risky given Alexa's history with kids accidentally ordering things and the privacy lawsuits, and what it signals about an "Alexa for healthcare" or "Alexa for law" coming next.

The Watson Weekly Weekend edition is sponsored by Avalara - the agentic AI platform automating global tax and compliance for leading eCommerce brands. For more details: https://avalaratax.watsonweekly.com

Then GameStop's Ryan Cohen and his $56 billion unsolicited bid for eBay, half cash, half stock. The eBay board's response was a 216-word letter calling the offer "neither credible nor attractive." We dig into whether Cohen ever expected a yes, or whether the whole thing was theater aimed at GameStop's stock price and the $100 billion valuation target tied to his own bonus plan.

Finally, Lululemon. Heidi O'Neill, 30 years at Nike, took the CEO job on April 22. Founder Chip Wilson is already on record saying she's not the transformation the company needs. We talk about why Alo Yoga and Vuori are pulling away on the celebrity side, why the men's line feels over-assorted, and what it means when Amazon, Costco, and Target all stock convincing dupes of your core product.

Logicbroker brought back Connected Commerce this year, set up outside Central Park, because the conversations the team has been having with customers couldn't wait for the usual conference cycle. The pace of change forced the issue.

Rick Watson had the opportunity to speak with Logicbroker CEO Omar Qari at the event.

The dominant theme was the agentic shift, and it landed in a specific way for LogicBroker. They sit as the connective tissue between retailers and suppliers, which turns out to be exactly where LLMs are now hunting for product data. The network already has what the models want.

A few other things the room kept circling back to. Most AI experiments fail, and attendees were comfortable saying so. One real win out of twenty counts as a strong batting average when the work is closer to science than to product launches. The shape of leadership came up too: the people running companies in this next stretch will need to build things, not just manage the people building things. Omar walked through his own setup, including Claude, a Slack bot he named Omar GPT, and a contract lifecycle tool he wired together himself instead of buying.

Rick Watson talks with Alan Gaffney (CEO, Townchest), Nick Boetcher (Avalara), and Justin Samakow (Mirakl) about what breaks when a marketplace scales.

Townchest runs a "shopping for good" program where schools partner with manufacturers to fund themselves through retail sales. A regional launch created nationwide Nexus exposure within weeks, because supporters of a school in Ohio live in Texas, California, and everywhere else. Alan unpacks the hybrid seller-of-record setup that followed: Townchest carries that role for some partners, not others, and the operational cost runs both ways.

Justin and Nick cover the back-end. Mirakl's Catalog Transformer normalizes supplier data and pushes it into thousands of school storefronts. Avalara's Avi agent assigns tax codes from a global library against the data Mirakl sends through. The two also get into where strict SLA automation earns its keep (auto-deactivating sellers who miss order acceptance) versus where alerts suffice (high return rates).

The Private Storefronts, Shared Suppliers, One Compliance Nightmare webinar was sponsored by Avalara and Mirakl.

Shopify posted its strongest quarter in four years and the stock fell 7%. Rick walks through why Wall Street wasn't impressed, what the LVMH signing actually means for the "Shopify is only for startups" narrative, and the credit-loss line item that's quietly getting bigger.

Also this week:

Amazon Q1: three numbers Wall Street missed, including a $150B grocery run rate and free cash flow down 95%

The Watson Weekly is sponsored by Avalara—the agentic AI platform automating global tax and compliance for leading eCommerce brands. Go to avalaratax.watsonweekly.com for more details.

Alphabet's Universal Commerce Protocol, now signed by Kingfisher, Target, and Wayfair

GameStop's $55.5B bid for eBay, with Ryan Cohen pitching it as "Chewy on steroids"

Investor Minute: PayPal restructure, Recharge buys Skio for $105M, Cognizant grabs Astreya for $600M, Lipton takes a $245M CVC investment, District raises $14.7M seed

Three stories on the table this week, and none of them small.

Saks Global plans to exit Chapter 11 on June 22nd carrying $1.2 billion in debt, with a reorganization plan targeting $9 billion in GMV by fiscal 2030. That's nearly double where they sit today. Rick Watson and Jessica Lesesky walk through the vendor mess (720 brands stopped shipping at the worst of it), the repair work underway, and why exiting bankruptcy this leveraged sets up another round of trouble down the road.

The Watson Weekly Weekend edition is sponsored by Avalara - the agentic AI platform automating global tax and compliance for leading eCommerce brands. For more details: https://avalaratax.watsonweekly.com

Over at Victoria's Secret, Australian investor Brett Blundy's BBRC Worldwide has built a roughly 13% stake and is pushing to remove two directors: chair Donna James and Miriam Naficy. The complaint is acquisitions like Adore Me. CEO Hillary Super is running a "path to potential" plan built around body positivity and a return to the Angels heritage. Fiscal 2025 sales are up 5%. The question is whether that's enough to keep the activist quiet.

Then earnings. Alphabet did $109B in Q1, with Google Cloud growing 63% YoY to a $20B run rate and a $462B backlog. Amazon hit $181B, AWS grew 28% to $37.5B, and the chip business crossed a $20B run rate of its own. Shopify cleared $100B in quarterly GMV for the first time, with operating income up 88% on the back of all the layoffs and restructuring.

The thread underneath all of it: AI compute is getting more expensive, not less. The pricing power is sitting with the infrastructure layer. Amazon, Nvidia, and the LLM owners are collecting the rent. The businesses adopting AI are paying it.

Rick Watson sits down with Mike Hogenmiller, who has spent more than forty years inside home improvement retail and watched the consumer reinvent themselves at least three times.

Mike was at The Home Depot in 2001 when the company quietly acquired a 4,000-customer wholesale distributor in Baton Rouge, LA called Your Other Warehouse. That distributor was, at the time, Amazon's biggest and most profitable home-improvement supplier. The acquisition (plus a later decision to stop opening new stores and make existing assets more productive instead) is how Home Depot got roughly 15 years ahead of its closest competitor on digital fulfillment without ever calling it e-commerce.

The Watson Weekly interview is sponsored by Avalara - the agentic AI platform automating global tax and compliance for leading eCommerce brands. For more details: https://avalaratax.watsonweekly.com.

The story Mike tells about then-CEO Craig Menear is the part most people miss. Home Depot wasn't building an e-commerce business. They were building commerce. The customer decided what they bought, when, where, and how it arrived. Everything else followed from that.

We also get into:

• Why Walmart's culture survives and Target's didn't

• The Sprouts problem and what happens when a specialty grocer stops buying with confidence

• Why every "Amazon of [insert vertical]" pitch ignores the customer

• Where CPG brands keep going wrong inside the store

• The advice Mike gives DTC founders thinking about their first physical stores

H&M just listed on a US online marketplace for the first time, and they picked Nordstrom. Rick Watson and Nick Kaplan break down what that signals about both brands, and why marketplaces with no inventory commitment keep working when standalone marketplaces keep dying.

Next up, GLP-1 hits the bridal industry. 10% of couples planning weddings this year are on a GLP-1, and more than half started the medication specifically for the wedding. Some users drop a clothing size every two to three weeks, which is a problem when a wedding dress takes nine months and costs five figures. Bridal shops are now asking buyers to sign waivers. Rick and Nick widen the conversation into plus-size assortments, the longevity boom in CPG, and why protein and creatine are having a moment.

The Watson Weekly Weekend edition is sponsored by Avalara - the agentic AI platform automating global tax and compliance for leading eCommerce brands. For more details: https://avalaratax.watsonweekly.com

Then the big one: the e-commerce organization of the future. Unilever cut from 3,000 agencies to under 800, saving half a billion dollars. P&G in-housed media for $750M in fee reductions. A retail "season" is now two weeks. Where does the merchant sit in all of this, and is ChatGPT a better buyer than a human? Nick argues the merchant role contracts but never disappears. Rick pushes on whether the 2026 merchant is really just one person editing algorithms instead of product.

Subscribe to the Watson Weekly newsletter at watsonweekly.com.