Winners and Losers From ChatGPT's Shopping Launch

In this podcast, Motley Fool contributors Travis Hoium, Lou Whiteman and Rachel Warren discuss:

• ChatGPT's shopping launch.
• Winners in agentic shopping.
• Losers in agentic shopping.
• How big tech will adjust to the new world of commerce.

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A full transcript is below.

This podcast was recorded on Oct. 01, 2025.

Travis Hoium: Are AI agents, the future of shopping? Motley Fool Money starts now. Welcome to Motley Fool Money. I'm Travis Hoium joined by Lou Whiteman and Rachel Warren, and we have to talk about the big topic of the week. That is OpenAI's announcement that they are going to allow shopping within ChatGPT. Don't even have to leave ChatGPT to buy your Etsy orders and stuff from Shopify. Rachel, there's a lot going on here. What did we learn about this? Is this something that people want? It seems like the industry in AI has been talking about this as a phenomenal use case. As I see early examples, I'm a little bit skeptical, but I'm willing to be swayed, o what are your thoughts on shopping within ChatGPT?

Rachel Warren: Yeah, this is honestly fascinating to me, and I think, particularly as we have watched online shopping and what that looks like for consumers evolve so much over the last few years. I do think we're going to have to see how comfortable users are actually using ChatGPT to shop. How many people are actually going to do that? I'm not convinced, but I do think we could see this become a new normal if the interest in adoption is there, but, how does this work? OpenAI has launched this new shopping feature. It's called Instant Checkout allows users to purchase products directly within a chatGPT conversation. Let's say you put into ChatGPT best running shoes for under $100. Well, then ChatGPT would pull up a product that supports whatever you were looking for. You get to see a buy button that would appear, and you could actually review shipping, payment information, complete the purchase all without leaving the chat interface. As you mentioned, you know, this is first launching with Etsy sellers.

Travis Hoium: This is powered by Stripe. Which is the same company that powers Shopify shop pay. Just to put some context, this is there is a playbook here from the quick checkout.

Rachel Warren: Yeah, and I think it's a good point you raised because essentially, they are relying on proven infrastructure. I do think it was an interesting choice that they chose to launch with Etsy sellers. They're soon also planning to be available to a really extensive number of brands on the Shopify platform like. Skims and Spanks, but as you mentioned, this offering, it's powered by a protocol that was developed by Stripe and OpenAI and basically, it uses AI agents to act as purchasers on behalf of consumers. How is this monetizable? OpenAI is going to take a small fee from merchants. The service is free for users. Right now, you could only purchase one item using this service, but OpenAI has said they plan to expand in the future. It's very early days, but I don't know, I'm intrigued.

Travis Hoium: Lou, you and I are probably not the early adopters here with AI and shopping, but there does seem to be something too. I'm looking for this kind of item. Tell me when it's under $40. There's value there, but is this going to replace something like a Google search? I think that's the big question.

Lou Whiteman: Well, I think at its heart, this is the long awaited, we've all talked about how is Google under threat from AI because searches will move to AI? This is fact playing out in theory. I'm skeptical, though. For one thing, for now at least, it is a closed garden. You're only going to get access to the people who the retailers that partner with ChatGPT the ones that accept their open protocol, little names like Amazon and Walmart, at least for now, aren't involved. It's only going to be as good as the choices that are there. The bigger thing, though, and this is the big AI problem. It's garbage in garbage out or how good is, if you ask for best running shoes under $100, the AI isn't going to test running shoes. They are just going to find the reviews. Now, I know, like if you right now do a Google search, like best gifts for an 18-year-old girl going off to college or something, you're going to get a pretty generic clickbait list 300 times coming up girls like flowers. There's just something silly like that. If that is what is feeding these models, if it's just that clickbait that's all over the web anyway, is this really going to be your personal assistant, or is it just going to be another disappointing option? I don't know.

Travis Hoium: The incentives are interesting, too. Google, the incentives are who is going to pay for the ad placement. Now when you do a Google search, whether you're on a mobile device or whether you're on a computer, the first things you're going to see are all ads, but generally, those line up with what the top search results are, from an organic search perspective, too. They're just squeezing more margin out. Same thing happens with Meta. I think that's a company I want to touch on in a bit, but that's a discovery tool for things that I didn't know that I wanted, there does seem to, be some tension here in the way that people naturally shop and the way that people have learned to shop online and how this is going to work. Rachel, is there going to be a learning curve with using something like ChatGPT to shop and where it's useful and where it's not?

Rachel Warren: I do think there's a learning curve, and it is interesting because you see it taking what we as shoppers and consumers are used to with, say, doing a Google search for a particular product, clicking on an item we like, and then, going to check out. I think it's taking that process a beyond what consumers are used to, and I think that's where it remains to be seen, is that something that really resonates with people when they're shopping for various products? I think it could be very possibly the next evolution in retail and what shopping looks like, but I don't think that that's something that would necessarily be exclusive to OpenAI's ChatGPT, which I know we're going to talk about more in a bit in terms of how other companies are integrating these AI features. I think that's important to note. It's not just OpenAI. I think they're just probably the most prominent example right now.

Lou Whiteman: The other real question here is, I think this is incremental. It doesn't feel like a new paradigm. It feels like, again, like I say, a different form of Google Search, or maybe if it's done well, a better form of search. How do you even if it is better, how do you change consumer behavior on something like this? Even if you've built a better mouse trap, and the jury's out on that, how do you stop me from doing what I've been doing for ten years? That to me is the big challenge they face. They are really going to have to have a wow product, I think, to do that, and we'll see. Maybe it is.

Travis Hoium: Well, we're going to see who Lou and Rachel think are the winners and losers of this announcement and how this is going to play out in the tech industry in just a second. You're listening to Motley Fool Money.

Welcome back to Motley Fool Money. I want to get to the positive side of the OpenAI shopping announcement and who we think the winners are. Lou, I want to start with you, this is going to potentially be disruptive to a lot of companies, but there are going to be companies who are going to be able to take advantage, and maybe it's that long tale of retailers, it's tough to find consumers if you're not in a pig box retailer. Is that where there's opportunities for investors today with this announcement and maybe other AI shopping agents coming on the?

Lou Whiteman: I can see why retailers would want to do this, because you're right. Right now, Google Ad word searches the ways they're doing it. There's no perfect way out there right now so why wouldn't you try to extend things? I think juries still out whether or not they are actual winners over time with this, because, again, a lot has to go right. I think there's a lot of ifs there. If this catches on, if it dries more traffic, if it converts, there's a lot of potential. There's not a lot of clear things. The real winners for me here are the consumers, because I think, if these agents do give you better ability to price shop, I don't know if that's great for the retailers, but I do see a world where a pretty simple thing for agents to do is to just monitor prices and to let you know when something that you looked at is cheaper, so that's great for me. It might crush margins elsewhere, but it's great for me as a consumer.

Travis Hoium: Lou has the consumer as the winner. Rachel, where do you think there's opportunities?

Rachel Warren: I think there's opportunities a few different ways. Obviously, the first companies that come to mind here are the ones that were mentioned in this announcement, Etsy, Shopify. I'm quite a lot more bullish on Shopify just as a business as a whole and as a direct beneficiary of these trends than Etsy really for a variety of reasons, and we also saw, you know, shares of Etsy, go up really significantly about 16% after this announcement, and then plunge down by the end of the day. I do think that there's a lot of opportunity here for really traditional retailers, too. There was a study that came out this last month that showed that generative AI platforms are already driving a lot of referral traffic to some of these companies. ChatGPT accounted for about 21% of Walmart's incoming traffic in August. You can think of companies like eBay that could benefit here, maybe target, that could foreseeably be winners from adoption of this technology on the backend, right, helping to really, I think, automate some of their infrastructure behind the scenes. There's a payment angle to this, too. Companies like PayPal, Visa, Mastercard, they're developing a lot specialized infrastructure and toolkits for AI agents to process secure autonomous payments. For me, and maybe this is where I differ from Lou a little bit. I think there's a real benefit here to improve the infrastructure of retailers and payment processors. I don't think we're living in a world where most consumers want, for example, an AI agent to do their shopping for them, but if you want to automate that core infrastructure or make maybe shopping easier, there's a value proposition there.

Lou Whiteman: But is this winning or is it just a shift? Because for the payment people, Mastercard, Visa and PayPal, are they going to get more business out of this, or is it just they're already getting a ton of business. It seems like same volumes from a different source. Similar to the retailers. It has to be right now, this source of traffic is shifting. Is the traffic higher quality? Does the traffic convert more? Or is it just that, this is a story of maybe simple search losing share to AI to be a winner here? I think there has to actually be incremental gains either in volumes and conversion, something like that. It could be that AI just gives you better recommendations, so therefore, they convert to sales better. Again, I think a lot of that's going to be the data that it's training off of, and that is what the search data, you know, so there's a fine line there. Etsy was up 16% on the news, but then gave up most of that the next day Shopify was on that same press release went up less. I don't think that is because Shopify would benefit less. I think it's more just, Etsy investors are more desperate to hear they're involved in this. I think there's a lot of hype here. There's a lot of potential, but I think we just have to see.

Travis Hoium: Lou, do you think there's an opportunity for a lower take rate from that discovery side of things? If you think about Etsy and Shopify in particular, they've grown a lot on things like Instagram ads. The problem is Instagram is really good at monetizing their business and squeezing out a lot of that margin for themselves leaving these smaller retailers in particular with, you know, relatively modest margins. You can decide what your margins are going to be based on what your ad spend is going to be the initial launch is going to have a relatively low take rate for ChatGPT and OpenAI, from everything that we've heard. That could help those margins. Short term, then the question becomes, do we see the squeeze that we've had with something like Meta's family of apps over the past ten years where they just keep increasing that take rate over time. Is there almost like a short term benefit, potentially because this is a new distribution, new discovery model that's relatively low cost? And then maybe those dynamics change over the next decade?

Lou Whiteman: It's very possible. I do think that what I feel more certain about is that if there is a margin expansion, it's going to be temporary, because that would imply that the OpenAI product actually works. OpenAI has, what, commitments to spend, I don't know, $1 trillion or so in the years to come. It's not like they can afford to let other people, get fat off margins, maybe, but again, I think all this is premised on the fact that it is a good enough product that gets us to switch our habits, and that by itself is a big hurdle.

Travis Hoium: We're going to talk about the companies that are going to be negatively impacted in just a moment. You're listening to Motley Fool Money.

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Travis Hoium: As shifts in shopping change, if we do move to more AI agents, whether it's in ChatGPT or another AI agent engine, there are going to be some losers out there, and we saw this with the shift to more online shopping over the past 20 years. Companies like Sears that used to be dominant are now effectively almost gone. Rachel, I want to start with you. Where do you see companies that could potentially be under threat because of something like OpenAI shopping?

Rachel Warren: I think one of the things that we've been hearing a lot is that this could be a major type of disruptive technology to some of the big tech players, right, like Alphabets Google and Amazon. I'll talk about that a little bit. I'm personally very bullish on these companies, but I do think as a long term investor, it is good to look at the bare side of things. There's this concept that AI agents that handle foreseeably the entire search to purchase process, that could erode the search ad revenue that powers Alphabets Google. Now, I will say, Alphabet has predicted this threat. You know, Google's been developing a new shopping assistant experience using AI that's accessible within their search products AI mode. They have their Gemini AI that they've combined with their shopping graph, which indexes over 50 billion product listings that they have been working to develop their own feature. I think that's something to bear in mind when you're looking at that cupiy. Another one, of course, there's this idea that agentic AI shopping could present really unique threats to Amazon's dominant position, maybe weakening the Walled Garden. This idea that maybe if external AI agents could crawl the catalog, compare prices, without a customer even visiting Amazon, that they would lose control over their journey. The argument, I would say to the flip side of that is, first of all, Amazon has incredible economies of scale, and they're building their own native AI shopping tools. I think that includes, as well, their agentic checkout feature. I think the issue will be that retailers or companies that lack robust AI strategies, they're going to struggle to compete, but you've got businesses like Alphabet, like Amazon and others that have tremendous capital backing them up incredibly well known and trusted platforms. I don't think we need to be sounding the alarm that these entities are just going to go away because of OpenAI's ChatGPT rolling out new features.

Travis Hoium: Lou, a couple of things that I want to just highlight that Rachel pointed Amazon has been talking for years about the growth in their ad business. That is basically capturing a larger percentage of the shopping that's going on on the Amazon platform. This could potentially you don't need an agent doesn't need to see ads. Google's entire business is basically ads so is that where the threat is? Is we go from a world where advertising is really important to the agents don't need ads, and it's how the crawler works, how the model works that's more important, and some of these big tech companies do see pressure.

Lou Whiteman: Let's separate them because I think it's a different answer for both. For Google, Google's core business, yes, it's ads, but it's basically Google's core business is funneling consumers to a retailer or to a destination. I think that that can cross over into an AI world, using Gemini, using Google's products. Yes, right now, that is in the form of ads. That's how they monetize it. It could easily be just referral or whatever we're talking about.

Travis Hoium: This would be the example of they were founded on just giving you the answer, not serving you ads. We're almost moving more to that direction. Hey, I want a great pair of shoes. Just go buy it for me. Maybe Google is best place to do it.

Lou Whiteman: At the end of the day, Google's about connecting someone who has a desire to someone who can fulfill that, and whether I think that can take different forms. Amazon, though, is interesting. As the name implies, Amazon is supposed to be that one stop shop. Why do we use Amazon? Because I can get everything. I can get everything from roach traps to the new sweatshirt, to the kids new bike all at one place, and so I do think that there could be a foundational threat here, just if your chatbot is that same Amazon. It has all of the world in there, and you can do a one stop there. A couple of other thoughts for retailers, I don't know if I'm worried about retail losers if they don't have a good AI strategy. I feel like this is almost allowing them to punt their AI strategy. They can just sign up with OpenAI or something like that, and they can outsource that. And that's good enough. A couple of other losers I worry about. I mentioned I think retailers can be losers if this just becomes a margin instruction tool. I think I said consumers are winner. The one thing to watch here is say we end up in a world where Etsy and Shopify sign exclusives with OpenAI, and they aren't exclusives now. And then Gemini comes along and signs an exclusive with, I don't know, Target or someone like that, and so, all of a sudden, we have just walled gardens. Right now, I can Google search and get the universe. What if these things become a turf war and you have an effect, like a bunch of different wall gardens, so I have to go check OpenAI, and then I'll go over to Gemini to see. Well, then you just have an agent to check the agents. It would come to that. There's a lot of ways this can go wrong, and we are early days. At the end of the day, this, again, maybe I'm not visionary enough, but I just see this as a subtle shift from how we search for products that we're interested in today versus how we will. I do think companies have to adapt to that, but I do think that most of the incumbents are more than capable of doing.

Travis Hoium: I want to get quick thoughts on one of the things that has been interesting over the past 20 years is companies like Shopify enabling retailers to reach a wider audience that they wouldn't otherwise have in physical stores, but that actually came with a different need, which is reaching customers through things like ads on Instagram, ads on Google. There's a huge business in that advertising space. Does this potentially enable new business models where maybe I can have a product, and all I have to do is put a good description, maybe an image or two on the web or on ChatGPT's servers, and now it gets indexed and we don't have to go through this advertising layer that we have in the past. Is that potentially something that we're moving to, Lou, or am I overthinking this?

Lou Whiteman: I think we're a ways off. Like I said, I'm not going to go sell my shop if I on the idea that we don't need it anymore. I think there are still retail is a complex business, and there are a lot of tools that serve. I think we're a long way off till OpenAI just becomes my go to or any of these become my go to vendor. I still think just that again, to use the word that foundational vendor that's going to provide a ton of different services, including access to chat to agents. I think that's the way of the near term future, anyway.

Travis Hoium: Well, this is definitely something we're going to have to watch going forward. I do want to ask you quickly, and I'll start with you, Rachel. We got a couple of announcements of AI, social video products, OpenAIs Sora came out yesterday as we're recording metas, vibes are out. These are actually only AI videos. Sora is a little bit goofy because they're trying to make it a social video that is made with AI, so we can make videos that are having Lou dancing in the streets or something like that, but is this potentially, an interesting way for them to grow in media and in video or are these throwing spaghetti at the wall, and nothing's going stick at least quite.

Rachel Warren: I think it's somewhere in the middle. The Sora app and then Meta vibes, the app that launched from Meta. It's basically these feeds of AI generated videos. With Sora, apparently, you can insert yourself into a video and you can include synced audio, but essentially, this new idea of social AI generated videos on these social media platforms. I think it is a little bit of spaghetti to the wall. We've talked about this before. It's giving me a little bit of Meta verse vibes. This is something that users are actually going to want to adopt?

Travis Hoium: That's not a compliment.

Rachel Warren: No, it's not. I could be wrong. Now, there could be use cases here, say for advertisers. Maybe this is a great platform for advertising. I think right now this is very much in the experimental stage. I think companies are trying to see what works, what resonates with consumers, and I would expect a lot more of that in the next few years.

Travis Hoium: What we can tell right now is these companies are trying to figure out what they're going to do with all these AI models. They're getting better, but what does the future look like? It feels like we're in that, early smartphone days we're figuring out how apps work and how to make money or early Internet days where there is a bunch of ideas. Yeah, Lou.

Lou Whiteman: Can I just say to Sam Altman and to Mark Zuckerberg the same thing I used to say to my daughter? Just because you can doesn't mean you should.

Travis Hoium: But we're happy that they're trying something. It's true. Well, this is obviously something we're going to be talking about a lot in the future, because AI is definitely not going anywhere, given the like Lou said, trillion dollar or so of investment that's going in just to keep OpenAI fed. Tomorrow, we're going to be talking about why you shouldn't panic about the government shutdown which officially happened overnight.

As always, people on the program may have interest in the stocks they talk about in the Motley Fool may have formal recommendations for or against, so don't buy or sell stocks based solely on what you hear. All personal finance content follows Motley Fool editorial standards and is not approved by advertisers. Advertisements are sponsored content and provided for informational purposes only. To see our full advertising disclosure, please check out our show notes. For Lou Whiteman, Rachel Warren, Dan Boyd behind the glass, and the entire Motley Fool team, I'm Travis Hoium. Thanks for listening to Motley Fool Money. We'll see you here tomorrow.