Why the most popular mobile shopping app is saying No to AI shopping

Good evening. A little later here than planned due to completing my civic duty of jury service.

And boy, there’s been a lot of news over the last few days that I’m following…

First, Google announced on Wednesday morning that users of Gemini and Google AI Mode should start seeing the ability to make purchases directly from Etsy merchants and Wayfair within those AI chats. This is all powered by the Universal Commerce Protocol (UCP) co-created by Google and Shopify, and announced last month. Merchandise from Shopify merchants and Walmart still to come.

Below, you’ll find an example I found out in the wild today. In this case, I used Google AI Mode to ask for recommendations for trading card display cases from Wayfair for my son (you’ll notice a trend later on in the newsletter). I received a few product recommendations, including the one found below, in response.

When I clicked on the product card, the image you see below on the left appeared in a column along the right side of the page. When I clicked on the “Buy” button, a small window featuring the “Review your order” section you see below on the right populated in the middle of the screen. It took about 20 seconds for that module to load, which wasn’t great. I also had to update my credit card and shipping info since it’s been quite a while since I’ve purchased something online with Google Pay. Anyone else try this out?

Separately, Google also said it was testing a new sponsored ad product within its AI Mode “to showcase retailers that offer” the merchandise that had been recommended in a previous user query.

Speaking of ads, ChatGPT started rolling out its much-discussed, in-chat ads for Free and Go users. (Notably, one of the company’s research scientists quit as a result.) Would love to hear from you if you’re testing these ads for your brands and how you’re thinking about this (expensive) opportunity.

On the M&A front, Salesforce acquired Cimulate, a startup selling AI-powered search tech designed to make legacy retail keyword search behave more like a modern AI system, returning better results for both long, conversational queries and short prompts.

You may recognize Cimulate from The Aisle’s 2026 predictions post earlier this year, when its CEO argued that AI is beginning to erode traditional in-store browsing behavior. (I’m not saying a paid Aisle subscription gets you acquired. But I’m not not saying that either.) Tips on the acquisition price welcome.

Lastly, the AI shopping agent Wizard has finally launched publicly after years of private beta testing. The startup, backed heavily by serial e-commerce entrepreneur Marc Lore, has built an AI-powered product recommendation app that it says is purpose-built for shopping. Most product recommendations on Wizard will link you out to a retailer’s own website to complete a purchase, but a partnership with Best Buy allow users to buy some electronics without leaving Wizard. More partnerships to come, the startup says.

Now on to the good stuff…

Last year, my wonderful editor at Fortune magazine, Alexei, had an idea: I should profile Whatnot, a fast-growing “live shopping” app that probably wasn’t getting enough coverage at the time for a startup growing as quickly as it was.

I had been following Whatnot a bit, in part because my son and I had gotten into sports card collecting and that merchandise category is one of the most popular ones on the shopping app. I also had been following the startup because a neutral venture capitalist I trust had told me it was probably the e-commerce startup with the best shot at growing into an online shopping giant.

So I dove in. The headline of my ensuing feature was “Inside the rise of Whatnot, the wildly-entertaining, FOMO-inducing, $5 billion shopping app you’ve never heard of.”

But the “you’ve never heard of” part is getting tougher to say with a straight face. Whatnot recently announced that its sellers combined for $8 billion worth of merchandise sales through the app last year. And as I glance at Apple’s App Store rankings right now, Whatnot currently ranks as the No. 1 most popular shopping app in the U.S. Seriously.

So what about AI? I recently sought out the company’s chief product officer, Tom Verrilli, who previously held a similar role at Twitch, to learn more about when and how Whatnot is integrating with AI tools or AI apps to bolster growth. I have to say some of his answers surprised me.