This week on the Watson Weekly weekend edition, Rick Watson and Jessica Lesesky discuss: Shopify pushes its buyback to $5 billion while every other tech giant pours cash into AI. We ask the obvious question: built for the AI era, or built for the next earnings call? Then Apple's new Siri arrives at WWDC running on Google Gemini, a roughly $1 billion-a-year arrangement that sits next to the $20 billion Google already pays to be Apple's default search. And Anthropic drops a memo on three possible AI futures on its way to an IPO, with Rick putting the whole thing on an 18-month-to-two-year clock.

The Watson Weekly Weekend episode is sponsored by Avalara. Avalara integrates with platforms like Shopify, BigCommerce, and WooCommerce. Learn more at avalara.watsonweekly.com

Software agents are now the highest-converting shoppers on the web, and most stores are built to lock them out. Rick Watson sit down with Stripe's Danny Smith, who leads global agentic commerce solution architecture, to work through what changes when your buyer is a piece of software.

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.

They cover why agents convert about 4x better than humans, why two-thirds of agent checkouts fail on sites built for people, and the four ways merchants can let agents pay, from approving every purchase by hand up to agents transacting with each other directly. Danny closes with three concrete moves to make now, starting with treating your robots.txt like a doorman instead of a bouncer.

It's June 8th, 2026, and Rick Watson breaks down the week's e-commerce news with his usual habit: put the press release down and look at the calendar.

This week: Amazon yanks Prime Day forward to June 23rd–26th and blames the World Cup and America's 250th birthday. Rick isn't buying it. With Q2 closing June 30th and a nervous consumer pulling back, this looks like a P&L decision aimed squarely at Walmart's grocery turf.

Then FedEx Freight starts trading on its own as FDXF and the new CEO promises to "leapfrog" the competition. The stock closed down 7% on day one. Rick stress-tests that word against the actual target: 15% operating margin by 2029, up from roughly 12 today. That's catching up, not leaping.

This week's episode 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.

Plus Anthropic's confidential IPO filing and why "confidentially" is the word everyone's skipping. The growth is real and genuinely insane, but most of the eye-popping numbers are run rate, the real annual figure is $10 billion, and the gross-margin question under 5 gigawatts of Amazon-funded compute is the one nobody can answer yet.

And the ShipStation Global merger: WEX and Auctane combine into a 3-billion-shipment Thoma Bravo roll-up. Rick's read on whether welding a freight desk to label-printing software actually holds together.

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.

Christina Hagopian has spent 24 years running her own brand strategy and creative practice. In this episode she joins Rick Watson to explain why a brand is far more than a logo: it's what people think and feel about you before your message ever lands, and it has to trace back to a company's actual mission, vision, and values.

She and Rick talk through the real and the overstated parts of AI in marketing. It earns its keep on brainstorming, competitive audits, brand voice, and rough first drafts of positioning or naming. It falls down on original, trademarkable work because it leans on the average of what's already out there, and Christina describes a case where it couldn't get something as specific as REM sleep brain waves right for a medical site. Her argument: AI replaces average design, not designers.

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 throughline is differentiation. In a crowded digital space, a clear point of view is what gets you noticed, and a strong brand is the foundation everything else stands on. You have one either way. The only question is whether you've built it on purpose.

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