The AI triumphs–and pitfalls–at a $5 billion online marketplace

Good evening.

I hope those of you enjoying summer are getting outside to soak up the last few weeks of the season. I’m trying my best to squeeze some of that in even while working on exciting plans for both the present and future versions of The Aisle. More soon.

Some quick hits on what has caught my attention this week at the intersection of AI and commerce. Then we’ll get to one of my favorite interviews of the year in the Center Aisle section below.

First, friend of The Aisle and e-commerce analyst Joe Kaziukenas spotted a new shopping format within ChatGPT today, starring Best Buy and a checkout experience that allows users to purchase a product without leaving the AI chat. I tested it out and was able to recreate the experience. In my search, some Best Buy listings within ChatGPT still linked out to Best Buy’s own website, while others featured a “Checkout” button like this one.

Kaziukenas said this experience was built using ChatGPT’s “plug-in” tools, formerly known as ChatGPT apps. I’ve reached out to OpenAI for more info.

Note that when I reached the payment page, the fine print revealed that “By continuing, you agree to save your information for future purchases within OpenAI.”

Maybe not a big deal to most, but I found it odd that not only was that feature not based on opting in, but that there didn’t appear to be an option to opt out from storing your payment info either. Perhaps something to consider for the person who takes the role of “Product Manager, Shopping” that’s currently open at the company.

Elsewhere, one of Stripe’s top execs, Will Gaybrick, sat for a wide-ranging podcast interview. While he acknowledged that agentic commerce in the most technical sense has not taken off yet, he predicted that, eventually, “checkout pages will go away.”

For now, he said he might be most excited about the role of AI agents in B-to-B payments. Which is a nice segue to today’s main feature.

Finally, I was happy to chat this week with my former Fortune colleague and fellow journalist Sharon Goldman for the podcast of her new media company, Ground Level AI. We discussed why I launched The Aisle, how the last nine months have been a wake-up call for some companies building in this space, and the storylines, trends, and innovations I'm most excited to cover going forward.

You can listen here.

Now on to the good stuff…

I first learned about Faire many years ago. It's a nine-year-old online wholesale marketplace, valued most recently at $5 billion, whose customers are independent retailers and brick-and-mortar shops.

But I admit that I have not previously covered it closely, which says more about me than the company. Basically, I’ve had a bit of an aversion to covering B-to-B e-commerce other than stories about brands’ relationships with major retailers like Amazon and Walmart. The B-to-B industry didn’t do anything wrong to me, but I have often just found storylines in B-to-C commerce more compelling.

I’ve recently decided that’s ridiculous. After all, it’s a monstrous space. Amazon Business, for example, announced recently that it was on track for more than $60 billion in annual revenue. More importantly, I’ve come across more and more industry leaders in the past year who are incredibly excited about the role AI technologies can play in modernizing how businesses buy and sell from each other. Not in the future. But right now.

And Faire is one of the more innovative companies in the space. So I recently interviewed Max Rhodes, the company’s co-founder and CEO, in what I found to be a very candid and compelling conversation.

Rhodes explained in detail why the biggest driver of his company's growth actually has a lot to do with “old-school AI,” not Large Language Models. But he also reveals where LLMs are actually pulling their weight, where they still fall short, and what has to change before he trusts one to power the “holy grail” tool he really wants to launch for his retailer customers. Plus, some insights on both the pros and shortcomings of the AI coding boom.

I’ve edited the conversation for both clarity and length. Hope you enjoy it as much as I did.