Half of 2026 is behind us. We went back through the first six months and split the big commerce and AI stories into two groups, the bold moves and the cold ones.

Start with Anthropic. While the attention stayed on OpenAI, it kept its head down and aimed at one customer, the enterprise buyer. The Snowflake deal landed. Opus shipped over the holidays and picked up real developer momentum. Claude Code gave those developers somewhere to work that wasn't a browser tab. That's a company that knew what it was ignoring.

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

Then Ryan Cohen. He aimed GameStop at eBay, took the board's rejection on the chin, raised his stake to 7.8%, and told anyone listening he wants to own it. Gutsy. The follow-through has been weaker than the opening move.

The cold list is shorter and sadder. eBay's roughly $1.2 billion deal to buy Depop from Etsy is still sitting in regulatory review, and Depop sellers are already watching boost fees jump to 12% and wondering what the integration does to the rest. eBay does not have a great record of making acquisitions work. OpenAI, for its part, backed away from checkout. Commerce has a way of humbling anyone who thinks returns, fraud, and merchant-of-record rules are somebody else's problem.

Unified commerce is a data strategy first and a Shopify decision second. Rick Watson tests that idea with two operators who have lived it. In episode two of the Shopify roundtable series, Rick talks with Elara Verret, Chief Digital and Customer Officer of Reitmans and Max Rolon, CTO of Domaine, about what enterprise retail runs into on the way to unified commerce. They get into the back-end systems large retailers cannot rip out, the staging environment Shopify does not give them, and the BOPUS and promotion gaps that still need work at scale. There is a stack conversation too, covering where a PIM, a dedicated IMS, and orchestration tools earn their place. The panel keeps returning to one idea. The software is rarely what stalls a migration. The people are.

The Big Green Bag Of Promise: Enterprise Shopify Webinar Series is sponsored by Avalara, Domaine, and Pattern.

The Big Green Bag Of Promise: Enterprise Shopify Webinar Series is not sponsored by Shopify.

This week on the Watson Weekly, four stories about who controls what you see and what you buy.

Papa John's wanted to reach you the moment your fridge runs empty, so it bought the data to know when that happens. Instacart supplied it. The company confirms this is the first time it has handed first-party purchase data to a brand outside packaged goods, served on NBCU streaming inventory. The targeting is clever. The results do not exist yet.

Amazon moved Prime Day to June for the first time since 2021. The stated reason is a crowded July. The real reason is a holiday Amazon never has to share. Adobe projected $26.3 billion in spending across the window, but CPI rose 4.2% in May and average order values fell 17%, with more shoppers reaching for buy now, pay later. Read that headline slowly.

The Watson Weekly 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.

FedEx grew revenue 13%. Strip out the fuel surcharge and adjusted operating income grew 3%, with margins down 70 basis points. The company spun off freight on June 1st at the bottom of its cycle and switched its fiscal calendar. The December report covers a seven-month stub year.

Cannes sold agentic commerce for five days on the Riviera. Amazon launched agentic ads on Alexa. Retail media hit a number near $150 billion, according to the people selling it. Capability and intent were everywhere. Proof was not.

Plus the Investor Minute: Redo, Orderful, Walmart's $1.4 billion move on Vibe, Tiger Finance and Glossier, and Bed Bath & Beyond buying a real estate platform.

#watsonweekly #papajohnspizza #instacart #fedex #amazon #cannes

Tourists flew in for the World Cup and went viral filming trips to Buc-ee's and Waffle House. Rick Watson and Jessica Lesesky unpack what that attention is actually worth, then move to two bigger bets.

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

OpenAI is selling ChatGPT as an ad platform, with claims of 900 million weekly users and a target of a $100 billion ad business by 2030. The pitch is conversational intent. The problem is everything the older platforms already learned the hard way about guardrails, minors, and regulated categories.

Then Shopify Editions Spring 2026, where the catalog is suddenly the whole strategy. Shopify wants to be the feed AI shopping agents read from, and Shop Pay is now available on any platform, anywhere. Rick makes the case that this is Shopify finally aiming at Amazon

#watsonweekly #bucees #wafflehouse #worldcup #openai #shopify #ShopifyEditionsSpring2026

Most brands still evaluate enterprise Shopify on license cost. The operators in this conversation evaluate it on opportunity cost, and that reframe changes the whole decision.

Rick Watson opens a three-part series on the business case for enterprise Shopify with three people who have actually run the migration.

Elara Verrett, Chief Digital and Customer Officer at Reitmans made the move to get closer to the customer without standing up an army of engineers.

Renee Halverson, CMO at Marine Layer, has run on the platform for more than a decade and scaled the brand without hiring a CTO to babysit the stack.

Scott Lux, VP of Digital Commerce at Stanley 1913, came from the Salesforce and Demandware world and now uses Shopify to survive high-heat drops, where the only question that matters is how many orders per minute the platform can clear.

The number that came up: one brand cut its tech partner count from 40 to 10. The argument underneath it: a fashion retailer's core competency is retailing, not running a development shop.

It isn't all upside. Scott's warning is blunt. The front end is nimble, but the downstream integrations into OMS and ERP are where "easy" goes to die, so pressure test them before anyone signs. Lara's warning is about people, not software. The agility is real, and most large organizations are not built to absorb it.

One point they all landed on, and it cuts against instinct: standardization beats customization where it counts. Checkout is the example. Shoppers trust the flow they already know, and rebuilding it rarely pays for itself.

The Big Green Bag Of Promise: Enterprise Shopify Webinar Series is sponsored by Avalara, Domaine, and Pattern.

Shopify wants to be the checkout layer under every AI agent, and its Spring 2026 edition shipped 150-plus updates to prove it. Meanwhile air freight spot rates climbed 41% year over year while demand grew 4%. Somebody is paying for that gap.

Shopify Spring 2026: building the plumbing for agents

Checkout now runs inside Microsoft Copilot, paid with Shop Pay. There's a universal commerce protocol built with Google. A new agentic commerce plan lets brands sell across ChatGPT and the Shop app without ever being on Shopify. Native B2B is getting pushed down to every plan, aimed at a $36 trillion market. The bet is clear: own the merchant-of-record layer before the agents do.

Kimberly-Clark: $3 billion to fix the supply chain

Two years into a five-year productivity program. CFO Nelson Urdaneta points to simpler manufacturing, a redrawn distribution network, and more automation. A $1 billion automated DC is going into Beech Island, South Carolina, plus an advanced plant in Ohio. The Kenvue merger closes in the back half and lets them pack trucks tighter by mixing heavy and high-volume goods.

Amazon's Peter DeSantis at VivaTech: AI is nowhere near done

DeSantis says models need to get 100 to 1,000 times more efficient before they're genuinely useful. The next leap comes from speed: a 40-millisecond reaction time to match human conversation. His fix is a flywheel where chips and models get designed together to drop cost and lift performance.

Air freight: 41% up on 4% demand

Spot rates hit $3.40 per kilo in May. Surcharges, fuel swings, and Middle East instability are doing the work, not volume. Northeast Asia is up 39%, Southeast Asia up 33%, and Europe to North America has softened. Most of that cargo is data center hardware and semiconductors.

The Investor Minute contains 5 stories this week.

The Watson Weekly 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.

TikTok Shop moved $4.4 billion in beauty and wellness. Saks wants $9 billion by 2030. Castle claimed $1.4 billion and was worth $16 million. This week is about which numbers actually hold up.

Three companies put big figures on the table. Only one of them earned it, and even that one comes with an asterisk. Rick Watson and Nick Kaplan have a thought provoking conversation on these 3 stories.

TikTok Shop: reach without trust

• Roughly $4.4 billion in wellness and beauty sold since the 2023 launch
• Brand executives call it a "mafia" because of the traffic it forces through them. The honest scorecard is the halo it throws onto Amazon and Ulta, not the checkouts happening inside the app
• Awareness is the strength. The weakness is trust: missing shipping confirmations, sellers you can't place, a buying experience that still feels provisional

The Watson Weekly Weekend edition 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

Saks Global: out of bankruptcy, into a target

• A Texas court approved the Chapter 11 exit plan. Debt cut 75% to about $1.2 billion
• $500 million in fresh financing, paired with a mandate to reach $9 billion in GMV by 2030
• The model that got Saks here is still intact: leveraged, low-margin, carrying expensive real estate. And the vendors who went unpaid earlier this year are not feeling generous

CaaStle (Gwynnie Bee): a $1.4 billion fiction

• The rental subscription business once known as Gwynnie Bee was sold as a $1.4 billion company. The real number was around $16 million
• Founder Christine Hunsicker admitted to securities fraud in March
• The part that should worry everyone: professional investors and auditors missed invented financials. One investor was reportedly paid off to stay quiet, and audit documents from a recognizable firm were falsified

What ties these together is how cheap a number is to produce and how hard the thing underneath it is to fake. TikTok has the reach but hasn't built the trust. Saks has the target but not yet the model to hit it. CaaStle had neither and sold the story anyway. The question worth sitting with: how many of the valuations you read this week are closer to Saks, and how many are closer to CaaStle?

Salesforce renamed Commerce Cloud to Agentforce Commerce and calls this its biggest release in years. Rebrand, or substance? Nitin Mangtani makes the case.

Every enterprise vendor is bolting "agentic" onto its roadmap this year. Salesforce went further and renamed the whole product. Nitin Mangtani, who runs Commerce and Retail Cloud, came on to defend the release line by line.

We get into Storefront Next, the new storefront meant to serve both the merchant who wants clicks and prompts out of the box and the developer writing code with AI-native tools. The agentic layer: a search engine built on shopper intent instead of keywords, native chat, a ChatGPT catalog integration going live in June, and a shopper agent that's supposed to behave like the associate you'd get in a good store. The B2B story the B2C headlines tend to bury, including round-trip quoting, multicart, and a buying flow that runs on WhatsApp. And modern POS, where the bet is that systems nobody has rethought in twenty years are finally worth rebuilding.

Nitin came in through the PredictSpring acquisition two years ago and ran Google's shopping team back in the early 2000s, so he's watched the discovery layer move before. His line throughout: technology for its own sake is worthless. Tie it to ROI and a better customer experience, or don't ship it.

So I pushed on the question every merchant on the platform is actually asking. Hear Agentforce Commerce, Storefront Next, and a ChatGPT integration in the same week, and what changes for you, and how soon? Listen and decide whether the rebrand earns the airtime.

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.

She told investors $440M. The real number was $15.7M. This week: the CaaStle fraud, Walmart's Subway play, and Shopify's $5B bet.

In this episode:

Walmart + Subway. Walmart folded Subway into its delivery app, with express orders coming off the Subway counters already sitting inside its stores. Live now in six states (Connecticut, Florida, Georgia, Ohio, Pennsylvania, Texas), with roughly 1,400 locations targeted by end of summer. Flat delivery fee, in-store menu pricing, 30 minutes or less. It rides on the Spark drivers and drones Walmart is already paying for, pointed straight at Uber Eats and DoorDash.

The CaaStle fraud. CaaStle told investors it booked $440 million in net revenue for fiscal 2023. The real figure was $15.7 million. Founder and CEO Christine Hunsicker confessed to doctoring the financials on a video call with her board in December 2024, then kept her job for three more months while investors heard nothing. She controlled that board. Co-founder Jaswinder Pal "JP" Singh sold $6 million in stock back to the company around the time investors started asking questions. Hunsicker pleaded guilty to securities fraud in March, admitting she defrauded investors of $283 million, and she's scheduled for sentencing this summer.

Apple rents the brains. At WWDC on June 8, Apple introduced Siri AI: a rebuild that reads what's on your screen, pulls context from your messages and email, and takes actions across apps. The part Apple said less about is who's powering it. Reporting puts Apple at more than $1 billion a year to Google for a custom Gemini model running Siri's cloud features. The China rollout waits on regulators. For a company that has spent decades insisting it owns its entire stack, renting the model from a rival is the real headline. Tim Cook hands the company to John Ternus in September.

Shopify's $5 billion vote. Shopify added $3 billion to its repurchase program on June 2, taking total authorization to $5 billion. Buybacks usually get read as "we've run out of ideas." Then Q1 revenue rose 34% to $3.2 billion and merchants cleared $100 billion in GMV for the second quarter in a row. Decide for yourself which signal you believe.

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