Rick Watson and Jessica Lesesky sit down to unpack a busy stretch across tech, shipping, and commerce. They open with Anthropic's confidential IPO filing, submitted to the SEC on June 1st, and what it signals about the AI lab's trajectory. After a $65 billion Series H that pushed its valuation to $965 billion, Anthropic now sits ahead of OpenAI on that measure, and Rick and Jessica dig into how it got there: a revenue run rate that climbed from roughly $10 billion a year ago to about $47 billion by May 2026, helped by a developer-first bet through Claude Code that has made it a serious contender for enterprise spend.

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

From there the conversation turns physical. USPS and DHL have signed a multi-year contract valued at well over $10 billion, with DHL handling pickup, sorting, and transport while USPS covers final-mile delivery. It lands at an awkward moment for the Postal Service, which posted a $9.5 billion loss in fiscal 2025 and whose Postmaster General has warned of a possible cash crisis within a year absent action from Congress.

The last segment covers Salesforce's push to wake up a commerce cloud that had been growing under 2%. The reported Contentful acquisition (somewhere in the $1 to $1.5 billion range) fits a long pattern that runs through MuleSoft, Tableau, Slack, and PredictSpring. Rick and Jessica close on whether the integrated Agentforce suite can hold up against focused players like Shopify.

Rick Watson runs through a busy week in retail. Walmart posted a $177.8 billion quarter, with revenue up 7.3%, U.S. comps up 4.1%, and global e-commerce up 26%, yet free cash flow landed at negative $1.9B as automation capex climbed. Advertising grew 37%, marketplace sales jumped close to 50%, and new shoppers skewed upper-income. At Sam's Club, more trips but smaller baskets.

Authentic Brands Group named a new CEO: founder Jamie Salter moved to executive chairman, and former MGM Resorts chief Matt Maddox took over. ABG holds 50-plus brands, $38B in system-wide sales, and 77% of the company behind Saks, Neiman Marcus, and Bergdorf Goodman. Salter floated an IPO within the year.

At Google I/O 2026, the Universal Cart follows shoppers across Search, Gemini, YouTube, and Gmail, AI Mode crossed a billion monthly users, and native checkout opened to UCP merchants. Kroger hit $16B in e-commerce with a first profit in sight, wages past $20, two senior exits, and 70 to 80 stores planned. Plus an Investor Minute on Global-e, Insider, and Brown-Forman.

This week's episode is sponsored by Avalara. For e-commerce brands, tax compliance grows more complex with every new channel, state, product, and market. Avalara Agentic Tax and Compliance automates the behind-the-scenes work so merchants can offer a smoother checkout, with accurate tax calculations, clearer visibility into tariffs and duties, and fewer surprises when orders arrive. It works with platforms like Shopify, BigCommerce, and WooCommerce, helping teams manage compliance faster and scale with confidence. Learn more at avalara.watsonweekly.com.

Rick Watson and Jessica Lesesky break down Walmart's Q1 numbers and what they say about where retail is heading. Revenue was up 7.3%, U.S. comps rose 4.1%, and global e-commerce grew 26%, but the more telling figures sit elsewhere: advertising up 37% globally and the U.S. marketplace up nearly 50%. Rick and Jessica make the case that Walmart is quietly becoming a digital services business, pulling in wealthier shoppers with celebrity lines and faster delivery, and backing it all with a $1.7 billion-a-year bet on fulfillment automation that Kroger and others will struggle to match.

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

From there the conversation moves to Google I/O and the "agentic" pitch, including a universal cart meant to follow you across Search, YouTube, and Gemini through Google Wallet. Then the happiness index returns for a look at a K-shaped economy, where affluent buyers keep spending (Amex reported 10% growth in card member spending) while a lot of people are cutting back on basics like gas. Rick closes with advice for brands: shrink the gap between deciding and doing. Take out the friction, lean on convenience and automation, and you win the customer.

#WatsonWeekly #Walmart #Retail #Ecommerce #GoogleIO

In this Watson Weekly interview episode, Rick Watson is joined by Lennart Stevens, VP of Product Management for Agentforce Commerce at Salesforce, who walks through Storefront Next, the latest evolution of Salesforce's commerce storefront.

Storefront Next is built for developers and for a world where AI and agentic coding are the default. You can spin up a new storefront inside Business Manager with a click-based setup. Under the hood it runs on Salesforce's Managed Runtime as a hosted headless surface, with an enhanced SCAPI layer that lets apps, kiosks, and other channels pull from the same data. The stack standardizes on React, Shadcn, and Tailwind. Existing customers keep their catalogs, prices, and promotions and surface them through the new API.

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.

Lennart also gets into the agentic tooling (agent shopper, agentic merchandising), quiet AI like product readiness scores that flag missing info without nagging, reusable content blocks and embedded Page Designer components, and turnkey industry templates for retail, cosmetics, and furniture that convert well out of the box. He covers the upgraded CLI, the growing library of skills, and support for UCP as the channel-selling standard.

The whole point: cut the standup busywork so developers spend time on what actually moves the business.

#watsonweekly #agentforce #storefrontnext #agentic

Two big retail earnings reports, two very different stories. Home Depot grew total sales 4.8% to $41.77 billion, but comparable sales barely moved (up 0.6%) and net income slipped to $3.29 billion from $3.43 billion a year ago, a sign of margin pressure. Target posted the louder top line, with net sales up 6.7% to about $25.15 billion and comps up 5.6%. The catch: net income fell 24% to $781 million, and the stock dropped nearly 5% after management guided comps down to roughly 1% for the rest of the year.

On the tech side, Google and Blackstone are launching an AI cloud company with as much as $25 billion behind it, built on Google's own TPU chips to take on Nvidia and CoreWeave. France's Publicis Group bought the data platform LiveRamp for $2.2 billion in cash, a wager on "data co-creation" for AI agents.

And 5 Investor minute stories from the world of venture capital, IPOs, and mergers and acquisitions.

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.

Home Depot just told the market it's treading water, and Rick Watson and Jessica Lesesky dig into why the remodeling boom never showed up. People are tapping their home equity to consolidate debt, not rip out the bathroom. Paint and outdoor are fine. Lumber, flooring, mill work? Not so much. So Home Depot is quietly walking away from the consumer and betting the house on pros, HVAC, and a $700 billion market.

The Watson Weekly 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: TikTok is now the fourth largest health and beauty retailer in the country at $4.4 billion, and the action isn't even in the videos. It's in the comments. We break down why brands should build the conversation first and let the comment section do the selling.

And the one that broke the internet: Everlane sold to Shein for $100 million, down from a $550 to $600 million peak. Common stockholders get nothing. We get into whether Shein actually paid cash for brand equity or just bought itself a respectable-looking front for a not-so-respectable supply chain. Jessica says the quiet part out loud. Rick's head hurts.

Plus a quick read on AI maturity from The Lead conference floor, and why the people who are most "AI-pilled" somehow ended up busier than ever.

#watsonweekend #homedepot #remodel #tiktok #comments #everlane #shein

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.