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18 Nov 2025 Cheeky Pint Satya Nadella describes how lessons from Microsoft’s history apply to today’s boom

“I think then what's exciting is that again, Pinterest played with commerce quite a few years back, maybe 10 years back. It hasn't taken off as a huge thing, but now if you have all the merchants who are offering their product catalogs as part of this protocol, then social sites like Pinterest and Instagram and Twitter get another run at this kind of commerce experience because you've way more merchant support and adoption for it than you had the first time around.”

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Recorded
18 Nov 2025
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Cheeky Pint

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…uper early customers that we have. We launched a few weeks back in ChatGPT as well, that it has to work. And again, the data is already bearing that out because it's so much easier as an end customer. Yeah, I've been talking about it. I'm a bit of a cricket nut, so I am always searching for something. And the problem is whether it's Amazon or Walmart or what have you, the search experience sometimes is hard on the site. So interestingly enough, these chat experiences first are fantastic. And the fact that they point back to the catalog, I mean the catalog is still king, but now if I can marry the checkout and the catalog, and that to me is where I think the seamlessness— Do you have any experiences, I've found versions of this. I'm curious if you've had experiences where for product research using an AI app is so much better than keyword-based search. It's amazing that up to last year we thought keyword-based search was an acceptable way to hunt for anything. Yeah. And the seller, the bottom line is, it's kind of like it is creating a custom catalog for you. I mean, the response is not like a SERP. We were buying furniture in our house and we were just saying, “Oh yeah, we have this much space available in this spot. What do you think is a good piece that would look good in that spot that meets these dimensions and things like that.” But it's crazy that we weren't doing that previously. You know what I mean? And so all this customization, being able to give vibes, general aesthetics, I'm looking for something slightly higher-end, but not super fancy. It's crazy that you weren't able to— By the way, that's just the other crazy, crazy thing. My wife's an architect, and so she sort of has this Copilot notebook in which she has all these architectural pictures and so on. And you can ask it quite high-level reasoning questions on what I should put in there. So it's able to take an architectural sketch, a drawing, and then take a public catalog of furniture and put those things together and reason about it. And that type of stuff is pretty magical. there. So it's able to take an architectural sketch, a drawing, and then take a public catalog of furniture and put those things together and reason about it. And that type of stuff is pretty magical. Our view on this, we are as really AI-pilled when it comes to commerce at Stripe, and we think a huge amount will move here. And all the merchant conversations we're having are bearing that out. And the way I think about it is that if you are doing open-ended discovery: “Oh, I'm interested in an outfit to buy for this occasion. I don’t know exactly what I want.” AI will be so much better at helping you with that than the current experiences where you're clicking through a list of search results or something like that, and then if you're doing targeted search where I'm looking for a specific object that meets these needs, I want this component for my bike. Then also being able to specify with AI the exact parameters of the search you have will be much better. You're like, “Wait, if you're taking all of the undirected discovery and if you're also taking all of the highly directed search, isn't that just all commerce that happens on the internet?” I think the only thing that's left that's out of that is like recurring staples. I need to order more pet food. That feels to me like the least affected, though of course, you have to discover the brand of pet food at some point originally, but yeah, that's kind how we're thinking about it and again, Etsy has been an awesome first partner because all the products are custom, right? Yeah, that makes a ton of sense to me. I mean the discovery part, which obviously people like Instagram and others have done a great job. So the question is, what's the discovery layer? That's one of the obviously personalized discovery layer inspiration for product. What Pinterest has done is interesting, so some layer like that married with this conversational interface. Well, and of course it'll be a rising tide that lifts all boats, where part of what we're doing with this is making merchant's product catalogs remotely discoverable and inventory and everything like that. And then remotely purchasable, where you don't necessarily have to go through the whole flow on their site and everything like that. You can just do it inside the magic wand Copilot experience. And so that is at the raw nuts and bolts level, what we are doing and what we're wiring up. I think then what's exciting is that again, Pinterest played with commerce quite a few years back, maybe 10 years back. It hasn't taken off as a huge thing, but now if you have all the merchants who are offering their product catalogs as part of this protocol, then social sites like Pinterest and Instagram and Twitter get another run at this kind of commerce experience because you've way more merchant support and adoption for it than you had the first time around. cial sites like Pinterest and Instagram and Twitter get another run at this kind of commerce experience because you've way more merchant support and adoption for it than you had the first time around. And we have a project called the NLWeb, and the idea to really take every catalog of every merchant and give it essentially a website, an NLWeb interface that then an agent can talk to, to be able to interrogate and get the deep search, so to speak. Because today in some sense, one of the biggest challenges is the quality of the catalog and the ability to use reasoning to do a deep search. If you can solve that, then to your point, every product will find its query. Yes, we're building out this platform in agentic commerce where we have some open source protocols like our Agentic Commerce Protocol. We obviously have the regular Stripe products people are using us for. It's particularly kind of tricky from a payments point of view because you're looking to have an AI app do payments on behalf of other people across all these different sites on the web without probably sharing all your payment details all across the web. This is an interesting payment thing that we're doing. Anyway, we're looking to build a platform business in agentic commerce. You guys seem to know a thing or two. What advice would you have for us as we build in this very nascent space, but when there’s clearly product market fit? I mean I think you have done that, which is one of the things that I would think is, what does it mean to participate in this agentic workflow for every merchant? So every merchant now will have to sort of come to someone like Stripe and say, “Hey, I have a catalog, I have a checkout. Please get me to meet agents in the most friction-free way.” And that done tastefully is why I would think I would hire Stripe for. And I think the merchant onboarding, because I'm assuming the long tail of merchants being able to click and say, “Hey, enable me for agentic commerce” is going to be the thing that's going to drive. Because the good news here is there is going to be multiple. I mean obviously ChatGPT is the big one, but there's going to be, I mean Google's going to be there. We are going to be there, Meta will be there, Perplexity, there's going to be a lot of competition. There's going to be a lot of front doors as aggregators, but the more interesting thing is they themselves will, on their website, or on their mobile app, will want to support natural language queries. And so all of that being enabled for or my own agents will go interrogate those things. So I think that that's the key thing to be challenged, or rather really solved well. Because going to a small merchant and saying, “Hey, you go stand up an MCP server, do this protocol, that protocol…” What's the “easy” button?…

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