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.

Every big commerce name put up growth in the first half of 2026. Rick's question is what it cost them.

Shopify had its best quarter in years and passed $100 billion in GMV, though loan losses at Shopify Capital crept up over the same stretch. Amazon beat estimates and then turned around and spent $44.2 billion in three months on AI infrastructure. UPS is doing something stranger. It's shrinking revenue on purpose, walking away from Amazon volume and booking about $1.2 billion in separation costs to chase higher-margin work. Walmart's real growth engine now looks like advertising. FedEx spun off its freight business and is trying to pull a billion dollars of cost out of the network. And PayPal keeps moving more money while the profitable part of the business sits nearly flat.

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.

None of that shows up in a headline growth number. Rick's case is that the cash flow does, and that it separates the companies actually getting healthier from the ones renting the look of it.

#watsonweekly #shopify #amazon #ups #walmart #fedex #paypal

The era of the weird, different storefront is over. On Shopify, design that converts beats design that surprises.

That is the argument in the third and final episode of our Enterprise Shopify series. Rick Watson sits down with Elara Verret, Chief Digital and Customer Officer at Reitmans, and Isaac Newton, Co-Founder of Pattern (part of Domaine).

Reitmans is a 100-year-old retailer with roughly 400 stores. It moved its flagship onto Shopify in under a year. Elara's own team had scoped that work at two to three years.

The conversation stays specific. Why the enterprise case for Shopify is agility and focus rather than cost cutting. Where customization earns its keep and where it just leaves you a maintenance bill. What happens when merchants start editing the storefront in VS Code and someone has to ask, politely, to turn off their Sidekick access. And the plateau Isaac sees over and over: brands that grew fast three to five years ago, then watched a dozen copycats erase what made them different.

Headless comes up. Both have opinions.

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.