Stripe's John Collison on How Agentic Commerce Will Reshape the Internet

The internet is made for shopping. For years, the main inputs for e-commerce transactions involved targeted ads, algorithmic recommendations, SEO, and lots of mindless scrolling. But agentic commerce might represent a sea change for e-commerce: With the rise of AI agents doing shopping on behalf of consumers, how are retailers going to adapt? John Collison, co-founder of the financial services and payment processing company Stripe, has first-hand experience with all the ways e-commerce has changed in the last decade, and he thinks agentic commerce is going to completely transform the online shopping experience. On this episode, we speak to Collison about how AI has already changed the way consumers make purchasing decisions, why keyword search is a "ridiculous" way to find things to buy, what it means when brands will have to appeal to AI agents as opposed to human buyers, and if AI agents can truly mimic human taste. Subscribe to the Odd Lots NewsletterJoin the conversation: discord.gg/oddlotsSee omnystudio.com/listener for privacy information.

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• 0:00Tracy Alloway?

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• 0:26Speaker 01

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• 1:49Speaker 02

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• 2:27Speaker 02

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• 2:43Joe Weisenthal?

  Hello and welcome to another episode of the Odd Lots Podcast. I'm Joe Weisenthal.

• 2:48Tracy Alloway?

  And I'm Tracy Alloway.

• 2:49Joe Weisenthal?

  So Tracy, another episode where I can mention that I've been vibing. No, but you know what? Here's something that I may have mentioned before.

• 2:57Tracy Alloway?

  I'm sure you have, Joe.

• 2:59Joe Weisenthal?

  But I'm not 100% sure.

• 3:00Tracy Alloway?

  Okay.

• 3:00Joe Weisenthal?

  I think I've mentioned it. It's actually very easy. You just come up with an idea and you type it in English and then it's there. You know, the hardest part? Registering a domain.

• 3:08Tracy Alloway?

  Yeah. You've complained about this.

• 3:10Joe Weisenthal?

  It's so, everything else is so smooth. Right? You just type it in English and then you like have your little app or whatever. And then it's like, oh, I want to put this somewhere on the web. And then you go to like a domain name registrar. I had been using a GoDaddy for a long time. And then it's like, that's it. This field for this field and this field for this field and toggle this and this worker, this pages and the A field and the at field and the B field. And I swear, that's like, it's like so maddening. I just hated it so much. It's so annoying. It's the hardest part of the whole aspect.

• 3:40Tracy Alloway?

  I have terrible memories as well about dealing with Bluehost and things like that. Is this the first time you've ever set up a domain?

• 3:47Joe Weisenthal?

  No, that's the thing. This is the other thing.

• 3:49Tracy Alloway?

  Yeah.

• 3:49Joe Weisenthal?

  I've done it before. Like if I've done it before and it's still incredibly annoying.

• 3:53Tracy Alloway?

  Progress comes slow to domain registration.

• 3:57Joe Weisenthal?

  I mean, there's probably good reason for it to be complicated. You don't want it to switch in the wrong direction. Anyway, I was very excited. It's a couple of weeks ago. It was actually while the two of us were in Madrid. The company Stripe, the payment company, announced that there was going to be some agreement with Cloudflare, which does a lot of web hosting stuff, where you could just have the agent buy a domain name for you. And so you think of one and you just type it in. This domain name and host it there. And I immediately like, oh, my God, I wrote about it in the newsletter. It's like, this would be so, this would have been so nice a month.

• 4:27Tracy Alloway?

  Yet another thing that you will never have to do again.

• 4:29Joe Weisenthal?

  Exactly. Let another.

• 4:31Tracy Alloway?

  So, I mean, I saw the Stripe news and it generated a lot of buzz and it all comes under the umbrella, I guess, of agentic commerce. So this idea that you can have agents that are actually directly transacting on your behalf with other agents or other websites. And I have to say, as someone who shops online a lot, this is the first time I feel disintermediated by AI.

• 4:53Joe Weisenthal?

  I'm, I'm actually particularly excited about this episode because I'm very curious, basically what you specifically will ask as someone, as a person.

• 5:04Tracy Alloway?

  A professional shopper on the web.

• 5:06Joe Weisenthal?

  I was gonna say, as a person of taste.

• 5:08Tracy Alloway?

  Oh, thank you.

• 5:09Joe Weisenthal?

  As a person of taste, I have seen you say scrolling like very nice paper, like websites for wallpapers and things like that. And I'm curious, what does it mean for that if your AI bot two years from now knows you so well? It's like, Tracy, I thought you needed this new wallpaper because you're doing this. I just went ahead and ordered it to you to be delivered tomorrow. This changes the world.

• 5:32Tracy Alloway?

  It brings up so many interesting questions about discoverability and taste, as you mentioned, and also just the nature of the internet. Because when I think about the internet, like a lot of other things, it's basically built to sell you things, whether that's products or information, content, and we know that it also runs on those sales in the sense that a lot of the internet is driven by advertising, which is related to traffic. Obviously, we actually did that episode way back about how the internet runs on millions of like ad auctions.

• 6:03Joe Weisenthal?

  That's right.

• 6:03Tracy Alloway?

  And so this topic of agentic commerce and the payment system, obviously it's of interest to anyone who shops and does stuff online, but it's also really relevant to the actual evolution of the internet.

• 6:16Joe Weisenthal?

  Couldn't agree more. And I would go further and say it's really important for like culture itself. Advertising is a creation of culture. Ads are influential. Ads do all this stuff. What if there's a change in advertising, all this kind of stuff? Anyway. Let's stop hearing from ourselves. We really do have the perfect guest, someone we've wanted to talk to for a long time, someone who is right in the thick of it and all this stuff with agentic commerce and payments. We're going to be speaking with John Collison, the president and co-founder of Stripe. So, John, thank you so much for coming on Odd Lots.

• 6:45Speaker 04

  Great to be here.

• 6:46Joe Weisenthal?

  I'm very excited. Buzzwords, et cetera. What is, quote, "agentic commerce," unquote?

• 6:53Speaker 04

  Yeah, so there's a bit of a definitional question, but broadly, it is AI buying something for you. And we think about it in two categories. One is on the consumer side of things. This is where you were skeptical whether Tracy will ever be an adopter, where you research something in ChatGPT or Claude or what have you, and then go buy it there or have it buy it for you. But then the second is your Cloudflare example, and so it's B2B or developer-led agentic commerce, where you're just trying to have Claude code do something for you, and as part of it, it needs to buy resources. And we can talk about that because they're quite different.

• 7:28Joe Weisenthal?

  Yeah, Tracy, and we'll get to this, but the resources is another thing I've whined about, which is that when you do an API key, you're like, have an ID and you're like, oh, you have to go to the web, and then sometimes you have to enter a credit card number. That's really annoying, et cetera. But we'll get into that. But that is another big element of it that I feel like is getting closer to being solved.

• 7:47Tracy Alloway?

  Okay, well, on this credit card point, I mean, the history of online payments is basically a continuous elimination of the friction, right? And going from I have to enter my credit card details to I have to log into PayPal to now I can just basically click a button, whether it's Apple Pay or something else. Is agentic commerce, is this just another leg of the frictionless process, or is something fundamental, in your view, changing here?

• 8:16Speaker 04

  Both. So, part of agentic commerce is just reducing the friction. And you're right that the general direction of travel over time, you go back to the introduction of credit cards when the earliest adopters of computer networks, and then the originally commerce, and now, like you're saying, wallets like Apple Pay and Google Pay, and we have a product called Link and things like that. There's generally been this elimination of friction. Our view is that at a very minimum, we're going to see, and Tracy, I think this is where you can maybe get behind us, is leave aside any agent decision making that's happening. Just the final step of buying something, you know, you might have researched a product in an AI app before where you're going back and forth. I was trying to buy a bike case recently to travel with my bike and you're asking all these questions hard versus soft.

• 9:01Speaker 04

  And do you need to take off the handlebars and what's the right one? It's finding all these cool little niche brands. I think it's actually quite good for smaller merchants, by the way, because you have the ability for them to be discovered that they mightn't have had otherwise. But anyway, when you find the product at the very end, do you really then want to go and be filling out all these web form fields and things like that? Or do you want to just say, yeah, that sounds good. Buy it for me in this size. And our bet is that people will want the lower friction option. I think in the history of technology, the lower friction option tends to win out. And so we think that clearly will happen and is happening to some degree already. It's just the agent filling out the forms for you.

• 9:40Speaker 04

  I think where you get this interesting question is, and when people hear agent to commerce, I think their mind jumps to the agent actually having some autonomy and doing some decision making for you. I think there the problem is people somehow jump to the examples. Anyone who talks about this phenomenon, they pick terrible examples. They're like, oh, the agent will book, you know, all the activities on your vacation for you. It's like people think about, they daydream about their vacation all year.

• 10:06Tracy Alloway?

  Yeah, that's the fun part. Researching and booking is the fun part.

• 10:10Speaker 04

  That's a fun part, or similarly with women's fashion. It's like the whole point is the scrolling, not just the buying. And so people pick these, you know, super enjoy, like it's the robots taking the jobs and people want to keep those scrolling jobs. And so when you think about robots having autonomy, I would instead proffer some examples where you really don't need to be. You give the AI a recipe and say, buy the things that we need to make this tonight. And yeah, the AI can probably guess that you have salt and you have garlic at home, but you need the ground pork. Or again, then migrating to the B two B example, no one needs to configure yet another domain and go through all those forms.

• 10:51Speaker 04

  If Claude Code can work with Cloudflare to buy the domain for you and set it up, I think Joe will be much happier and not feel like he's missed out on a valuable life experience.

• 10:59Joe Weisenthal?

  I want to talk more about the B2B stuff, but let's for a moment stick around on the B2C element because I think there are gradations of this. So one is just another elimination of the friction layer. At the far end of the spectrum, conceivably, there will be things where the AI truly does anticipatory buy you things that you didn't know you need, etc. And then there might be like some middle. I saw this screenshot recently and I couldn't find it before the episode. Someone tweeted it, but some retailer, I think it was a shoe retailer, had put a bunch of shoes on their website, but instead of like putting any brand names on the shoe, like we would say like a Nike Pegasus or a Nike Air Jordan, all of the shoes

• 11:41Joe Weisenthal?

  were like hiking boot that's good for semi-serious hiker. Do you see this currently, currently where we are on the agentic commerce trajectory? Do you see this currently where there's already a change in how retailers are presenting or displaying or promoting their wares such that they're more attuned for what the chatbot would identify or the AI would identify as cool versus what a human influenced by brands would pick up as cool?

• 12:11Speaker 04

  Yes and no. I mean, there's definitely changes. I think some of the stuff that's most notable is often not the most relevant. It's a little bit, it sounds like what you're describing is a little bit like the Thai restaurant called Thai Food near me.

• 12:23Joe Weisenthal?

  That's right, yeah.

• 12:24Speaker 04

  You know, do best in the SEO. But I think what we see as a kind of maybe a more interesting direction of travel is again, what's happening already, some amount of the form fields being filled out for you and kind of the friction reduction and a huge amount of, again, I presume you guys have both done this, is research in AI apps. And you know, the way I would frame that is just keyword search is ridiculous. It's ridiculous that we got to the year 2026 relying on keyword search where that makes sense for buying a book or a DVD where you know the title of the book or DVD that you're trying to buy. But that's about the limit of keyword search. And so the fact that anyone was trying to buy furniture or clothes or anything like that, and there was this text box at the top of the website where you put

• 13:07Speaker 04

  in your keywords. It's like, that's just, that's not how anyone shops in the real world, things like that. And so we're seeing this AI powered research where people can explore a product space and start to give constraints. And you have this textual Search interface, but you end up with kind of much higher quality search where it's like, okay, I have a spot in this room where I'm looking for a piece of furniture that's this wide max and this high because I need to fit it in there. That's the kind of thing that's just much better suited to the AI modality. So you see different kinds of product research possible. And like we said, it's very helpful to smaller brands because people aren't necessarily stuck behind the traditional aggregators anymore. They can break out. And again, I have found

• 13:48Speaker 04

  in my little research projects that I have done, find you often get these small brands surfaced that you might not have heard of before. And so we think it's actually probably quite good for the dynamism.

• 13:59Tracy Alloway?

  Well, let me ask Joe's question in a slightly different way, which is if we assume that in the future, if I'm a business selling something online, previously I was selling to humans more or less, like maybe I'd optimize for Google search results or whatever, but like mostly I'm trying to appeal to humans. And now I'm trying to appeal more to agents. What is optimizing for agents actually look like?

• 14:25Speaker 04

  Part of it is similar to traditional SEO, right? So you want to be legible to those agents. You want to be discovered by them. But part of what, at least I've seen, is that the AIs have pretty good taste. Joe, I don't know if you found this in your vibe coding. By the way, Joe, I'm reminded of it. It's sort of like the old joke, how do you know if someone vibe codes? They tell you about it. Exactly. Guilty, guilty. And again, I'm guessing you found that the AIs are very tasteful at picking libraries and picking specific subcomponents to use. And similarly, in our kind of early experience of the agentic commerce, they're quite tasteful in finding tools that suit the job pretty well.

• 15:07Speaker 04

  And so I think you may get this more efficient market phenomenon where at least in picking coding libraries or something like that, the AIs are have quite like I find when I do stuff, they're discovering libraries that are perfect for the job that I hadn't even heard of or something like that. I think you're starting to see the same phenomenon with products where, again, I have had the experience of, you know, I was trying to find a travel adapter and I found it from this tiny company that I had never heard of, but it's doing exactly what I want, where it's like an integrated travel adapter and power brick. It's really good. And I would never have come across that company otherwise.

• 15:37Joe Weisenthal?

  This is incredibly important because, as I mentioned in the beginning, advertising creates culture. It's part of culture, especially iconic advertising. And maybe it'll be a little while before the Nikes of the world, the Nikes and Apples of the world, they're going to be advertising for a long time. But do you see this eventually as sort of like? One of the things I think that the internet appreciates about Stripe as a company is you and your brother's commitment to interesting discussions of economics and so forth. And you talk about econ history. There are great debates about whether ad spending is a huge dead weight loss on the economy or whether it's something positive, et cetera. And I'm curious, could you see a sort of post-advertising future, you know,

• 16:21Joe Weisenthal?

  at some point on the horizon?

• 16:24Speaker 04

  No, I think we're quite skeptical of that for two reasons. One, again, with agentic commerce, we don't think the human goes away and the human in the loop goes away. And there's a huge amount of agentic commerce that can happen like we're describing, where you still have the human as the end decider. And so it will likely be the case that if you are searching for something, if you have a new microphone for the Odd Lots studio, you might ask it to go research and it'll present three or four different options with different trade-offs. There's no right microphone that's going to be kind of cost trade-off and things like that. And then ultimately, you will make a call and it'll go buy it for you. And when you make that call, some brand preference you have, oh, sure,

• 17:07Speaker 04

  I just know that they're like the ones with the really good sound quality. Not clear why you have that association. Maybe there's some advertising in there somewhere. But so we think brand preference and as part of that advertising will clearly stick around because again, it's definitely not going to be the case that agentic commerce means no humans make buying decisions. That's absolutely not our case. But again, this may be a good example. You want to buy new microphones for the studio. You do a lot of AI research. You then have a human decide and then you do a lot of AI execution. And so it's AI on both sides and then human decision-making in the middle. Brand affinity really matters in that world. The other thing, of course, is commerce can be directed or undirected. Where the directed side, like I was saying, I'm trying to buy a bike case. It's like, this is a thing that I I know I need to go do, I'm going to go do some research.

• 17:49Speaker 04

  Previously, you know, a Google ad might have been relevant to me, whereas now it's what appears in the AI search results. Obviously, that does remove some advertising, but for now at least, maybe some of the AI apps at least choose to bring back some advertising in those cases. But then a lot of shopping is undirected where you're scrolling Instagram and the joke goes that these days on Instagram, the ads are better than the organic content because they've gotten so good with the targeting and there's nice reassuring things that you might want to buy. And there that is advertising and people are going to stay scrolling social apps and finding cool products they want to buy. So I wouldn't be short advertising in this world.

• 18:39Tracy Alloway?

  There are some market stories where you want every detail. Joe and I have made quite a few podcasts on that basis, but sometimes you've only got 10 minutes and just want to know what's moving markets fast. That's the Barclays Brief podcast. Every week, experts from Barclays Markets and Research get you up to speed on what's happening and what to watch next. Concise, focused and brief. Search Barclays Brief wherever you get your podcasts.

• 19:06Speaker 05

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• 19:35Tracy Alloway?

  You mentioned machine readability earlier. Talk to us about the actual process of converting your catalog into something that an agent can actually read and how standardized that is at the moment and how standardized you expect it to be in the future. And then also, like, if you're standardizing for machine readability, I feel like it's difficult to capture some of what might make a product interesting. It's difficult to like code the actual vibes of a product, even with LLMs. I just find there's something difficult to capture. So talk to us about how you make you make it so that agents fully understand what is available to them.

• 20:14Speaker 04

  Yeah, so there's two levels here. The first is just being known in the same way that you'd be known to humans. Because obviously, all the L L M's have read the whole internet. That's what they're trained on. And they can do web searches. And so if you have good product pages that are informative and lay out the details of what the product does, if you have reviews, you know, if there's like a bunch of wire cutter reviews, things like that. You've probably seen this in searches where, you know, the A I app will say, you know, people love this product and they say X, Y, Z. But they've read the whole internet. And so being known, you know, I'm a big deal on the internet helps with the A I apps as it does for humans. That's kind of step one. Step two, and where Stripe gets more involved, is you need a lot of the mechanical wiring up

• 20:59Speaker 04

  so that the A I's can do stuff that are more programmatic. And this is where our agentic commerce suite that we, you know, had an announcement about. And this is what we're working on with Google and Microsoft and Meta and, you know, OpenAI and all those folks to actually do some of the commerce wiring up. And there, I'd say it's two things. One is you need a machine compatible way to get the very latest information about the product details. So it's one thing for the A I to have in its training run, maybe a year ago, read the whole internet and know that this product is good. You need to be able to tell the A I, is it still on sale, what SKUs are in stock, which sizes we have right now and things like that.

• 21:40Speaker 04

  And so that kind of up to date, being able to make real time calls to the seller so that the A I has fresh, correct information that it can present. That's thing one. And then thing two is wiring up the agentic checkout so the A I can actually buy it. And here you get into a bunch of boring like payments details, but for example, you want the customer to be able to buy a safe credit card, but you don't want to be.

• 22:01Joe Weisenthal?

  You're not allowed to describe details as boring on Odd Lots.

• 22:05Speaker 04

  On Odd Lots, there's no such thing as boring details. This is the boring details podcast.

• 22:08Joe Weisenthal?

  Yeah, so talk, start, yeah, keep going.

• 22:11Tracy Alloway?

  Start.

• 22:11Speaker 04

  Okay, so then for actually kind of handling a three way transaction where there's you in Chat G P T buying a product from this merchant or something like that, we're facilitating that transaction. And there you want to be. You don't want to be reentering your payment details on each website. At the same time, you don't want to be flinging your payment details around across different websites. And so we've built all the wiring up and also don't forget a lot of websites have historically bots used to be a bad thing. They used to discriminate bots. They would have bot protections and things like that. Whereas now it's like, okay, no, we actually want agents to be able to do this. And so you're unwinding some of the bot protections and having a little TSA pre for the bots that we work with, a way to kind of securely transfer a one-time use payment credential and things like this. There's a lot of wiring up beneath the scenes that businesses have to do.

• 22:56Joe Weisenthal?

  This is actually maybe like a good spot to slightly seg over into the B two B element of agentic commerce. Cause this gets to another thing that I think about, you know, I know one of the things that available training data is literally just looking at user mouse behavior, right? Because then theoretically, the AI model can go to a website and click the buttons just the way a human wants. But it all, it seems silly to me. Like ultimately, if we're building a human, we're building websites for human use and then a bot's going to actually scrape them. Why not just actually build it for bots in the first place? What are we seeing there? What are you seeing from retailers where the fundamental experience, is it going to be reshaped such that what we call the UX, the user experience is not really, the you is not the person, but the you is the bot.

• 23:46Joe Weisenthal?

  And is that changing how the internet is just going to look?

• 23:51Speaker 04

  So you're getting to a very core debate that's happening in AI right now, like some of these kind of questions at the frontier of AI as to where things go for practical purposes. But one of them is when you think about AI adoption for real world tasks, there's almost a race between maybe we make the world consumable by AI and we make the websites friendly for AIs to navigate and things like that. Or maybe just the AIs get good enough at unstructured computer use that you give them a desktop and you give them a mouse and a keyboard and there's no backwards compatibility that we built, but they just end up figuring it out anyway. And it feels like over the next year or two. Or maybe three, this question will be resolved.

• 24:36Speaker 04

  Right now, a lot of people, including us, are working on making the Stripe dashboard, merchant website, things like that, consumable by the AIs. And what that means basically is text, where the AIs are very good at working with text. And so you need a textual interface for a bunch of things that previously might have been clicking around on a website. But maybe.

• 24:58Joe Weisenthal?

  Sorry, just to be clear, this reminds me a little bit about the debate whether like apps in the app store should be skeuomorphic or not. But just to be clear, Stripe is kind of taking a bet on the other side that actually the websites that look like they're designed for humans will not be the way to place your, where to place your chips.

• 25:19Speaker 04

  Well, it's an option, right? Because if the AIs get really good at computer use quickly, then it's good, you know, then we have that answer. And you're seeing this a little bit when people get their open claw to go buy something and it's running on their Mac mini at home. The merchant might say, oh, but I don't have an agentic interface. It's like, well, we bought it anyway. The claw just went and did it and used a headless browser. And so you don't need to do anything to enable the computer use world because the whole point is that it's fully backwards compatible with the current world. But in the meantime, I think people want to have these really powerful agentic experiences. It's a bit of a race, right? I think businesses correctly want to be the first ones to capture all this demand. Because I think it'd be the case if you start getting presented results in an AI app. And it's like, okay, here are a bunch of options. This one you can just click buy now and it'll arrive in two days.

• 26:04Speaker 04

  Or this one, you have to go to the website and click around, blah, blah, blah, blah. I think you'll start seeing some consumer preference for the ones that click one, kind of like on Amazon. When there's like a seller that has Amazon Prime in the third party sellers, you're way more likely to pick that. And Amazon has done studies on this. You can imagine an analogous world within the AI apps where the businesses that support agentic commerce sooner outperform the ones that don't.

• 26:27Tracy Alloway?

  Can you talk to us about how agentic commerce could impact prices? And we all know that already, when people are researching for products, you might put in a prompt saying like, "Find me the cheapest pair of, I don't know, sneakers that fit the following standard." And so you could imagine a world where lots and lots of consumers are being driven to the cheapest possible option for their needs. And you could also imagine a world where maybe shops start to respond with more sophisticated price pack architecture, maybe dynamic pricing or something like that, which makes me wonder if the future is just going to be bots negotiating with each other over price endlessly.

• 27:07Speaker 04

  I think it's a bit, I mean, we can all speculate. I think it's a bit too early to have realized data there because, one, it's an early phenomenon. And obviously, secondly, the leading edge of AI apps is quite high income, which is not necessarily representative of what the durable equilibrium will be. The one that we think about a lot is microtransactions are probably going to be now possible. And so you probably have this whole segment of commerce that previously wasn't open. Because microtransactions, they never work or never have worked historically because of the kind of mental load of deciding. There's no point at selling Bloomberg articles for, you know, 40 cents each because by the time you've decided, you might as well just have bought a day pass

• 27:52Speaker 04

  or a subscription or something like that. However, if Bloomberg, and actually, I would love if Bloomberg had a proper API for their data. Because if you want to do anything involving finance, when you're vibe coding, it'd be really handy to have the Bloomberg data. And the terminal is not exactly at the right interface for AI. But selling Bloomberg data by the SIP. So it's like, okay, we're doing a query about the Strait of Hormuz. Let's pull in the Bloomberg data for that. And you pay whatever, a small amount for that one little data request. That's a microtransaction that could actually happen. So that's the big effect that we think the time is finally there because the mental load has traditionally been too high for humans. But AIs love overthinking things. They love scrutinizing every little decision. And so we might as well do that.

• 28:30Tracy Alloway?

  This is something I've been thinking about as well. If microtransactions become frictionless, right? Do people try to monetize more and more content such that basically like you're kind of paying a tax to browse the internet?

• 28:41Joe Weisenthal?

  By the way, John, I just want to let you know, I don't know if you know this, but Bloomberg has actually delegated some of these big strategic questions to me and Tracy. So they've actually said, no, the podcasters should get to decide. So we could, we could actually talk about this.

• 28:55Speaker 04

  If you guys could put word in with Mike and the crew, that just, I would like my, my coding agents to be able to talk to Bloomberg, to do data access. That would be really helpful.

• 29:04Tracy Alloway?

  We're messaging him right now.

• 29:06Joe Weisenthal?

  But no, this actually, once again, perfectly segues to my next question. One of the things I hear from, I've heard for years from my software developer friends, they use this binary, free as in beer or free as in speech, right? So there's like software that you can download for free and that's, you know, that's free as in beer, but then free can also mean sort of like you can do anything you want with it, free as in speech. I'm wondering on this point, whether we need a third sort of one, free as in roaming, free roaming, because every piece of data is theoretically valuable to a model maker. And every interaction with a piece of data, which maybe is called metadata, that's all, that interaction activity is also very valuable, et cetera. And I'm curious, given that every interaction and

• 29:49Joe Weisenthal?

  any version of that is valuable, are we going to be at the end of the sort of free roaming internet? Or we, where we always just be paying these billionth of a cent microtransactions, which theoretically become doable and reasonable, as we just sort of go along the internet, surf the web, because this is all very valuable information that's theoretically being exposed?

• 30:13Speaker 04

  I don't think AI is causing the end of the free roaming internet, because there's always been a lot of proprietary stuff, newspaper paywalls. I don't remember a free roaming Bloomberg that I could read without paying, even pre the AI era.

• 30:29Joe Weisenthal?

  Get the subscription, man. You could afford, just get the, get the terminal. Okay, sorry. I feel like I know you really want our terminal. Anyway, sorry, keep going.

• 30:38Speaker 04

  Yes. So there's always been a lot of proprietary stuff on the kind of consumer side where, you know, this content is only available behind a paywall. And then, again, to the data point, there's Bloomberg and FactSet and FMP and, you know, all these different providers. And so I think what all the providers are thinking about is, how do I make this stuff available to the AI without just necessarily making it available for free? Yeah. And so what that looks like with the data owners is content licensing deals, right? Reddit now makes a lot of money from selling the Reddit data because you have all this, like, super interesting human discussion. You have the various media publishers either kind of suing or doing partnerships with or both the AI companies. We are very interested in data providers generally, like we did a demo of Sessions as to how, you know, you

• 31:22Speaker 04

  could do a financial research project with your coding agent buying the information it needs to put together the PDF answer. But we're quite early in that journey. But no, I think there's been lots of proprietary data for a long time. And so it's more about how do we open that up to AI agents? I'm not sure you'd see that much of a constriction on what's available on the free internet.

• 31:42Tracy Alloway?

  But just to push back on that a little bit, there's also been a lot of free stuff on the internet. And one of the reasons it's been free is because of traffic and advertising. And so if that's not going to get as much advertising or traffic anymore, because everything is going through an LLM platform and people just aren't linking back directly, the temptation would be to try to make up that revenue by charging for the actual content.

• 32:07Speaker 04

  Yeah, but that assumes that what the AIs want to browse and what the humans want to browse will be the same thing. And I'm not sure that'll necessarily be the case, where it'll still be the case that, say, for media properties, you know, that is aimed at human consumption. And so they'll do fine with the advertising revenue they had. Maybe they have some incremental revenue that they can get from the AI stuff. And then, I mean, maybe you're right, that the really crummy aggregator pages where it's like top 10 lists, you know, you Google something and you get some SEO'd page and there's like a million Taboola ads on it that you're trying to click through and the pop over takes over your screen. Maybe those sites have a harder time, but I don't think anyone's going to really.

• 32:53Speaker 04

  Be too sad about that.

• 32:54Joe Weisenthal?

  But you've talked about this yourself, I think in a recent speech you gave. It's actually depressing to me because now, thanks to the vibe coding apps, there's a bunch of stuff I would have liked to build, say, around Twitter data, right? And there was an actual era in which a lot of these social platforms are very open with their APIs, et cetera. And now everything's sort of shut down, so you can't even really, you know, unless I wanted to spend thousands of dollars, you couldn't really build like an app that does something with someone's Twitter account, et cetera. And I think you talked about this in your recent speech. Doesn't this further accelerate the move of everyone to just sort of clamp down and allow people to roam their site and slurp up data?

• 33:34Speaker 04

  Yes, but just to clarify, the human roaming has, you know, you can still browse Reddit for free, you can still browse Twitter for free. What they're clamping down on, in some cases, is AI training scraping, where they want to put a toll on that. And maybe they didn't kind of intend for all that information to be kind of freely available to the AI apps. And there, you can argue whether that should be freely available to OpenAI and Google and everyone like that, or they should have to pay for it. But it's not the case that our very important intellectual commons of Reddit and X and all the other asylums that we like to frequent are going away for us as humans.

• 34:29Speaker 05

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• 34:58Joe Weisenthal?

  You know, you talk about microtransactions and people have been talking about microtransactions for literally decades, probably. And the example you gave, oh, why can't we just buy an article for 50 cents? I think there's various reasons why that never took off. But one aspect is just the cost of a transaction. And theoretically, particularly with like stable coins, you could have almost free transactions. Are you seeing actual use of stable coins in sort of B2B transactions because the sheer cost is so low? Like, where do stable coins come into this?

• 35:33Speaker 04

  Yeah, you're right that when you have this pay by the SIP model, you obviously just can't, economically speaking, have kind of a, an individual card transaction per, per usage. And by the way, this is the economic model of the AI economy because you have marginal costs for each token. And so no one really offers an all you can eat plan. You can subscribe to ChatGPT or Claude or something like that, and you'll have a plan and you'll eventually hit usage limits. Or you can pay on an API basis and you know, you'll top up with some amount of credits and then burn down the tokens. But everyone charges per usage at some level. And so then what do you do? And the kind of common mode which we power a lot

• 36:18Speaker 04

  of is kind of this usage based billing. We actually bought a company called Metronome to power that where you track credits, right? And so that kind of telco billing, you have your card on file and then you track credits. We are quite excited about what you're referencing, which is stable coins for this. You're asking that kind of how much are we seeing of it right now? Not that much yet, but we're building out all the infrastructure for it. The place where I think stable coins could be really exciting is you don't have to then go have a relationship with all these services. And so if you want to vibe code a little website and you're like, okay, I'm going to buy the domain from Cloudflare and host on Vercel and all these things, you know, you've had the experience of you have to go and sign up for all these services and do these things. And we think that experience of signing up

• 37:01Speaker 04

  for all these services should go away. And so we are making it where you don't need to do that. And paying via stable coins could be one way where you pay per web request or you know, per individual use, very small amounts, and you don't have to go sign up for a whole bunch of different services.

• 37:17Tracy Alloway?

  So I realize that agentic commerce is a spectrum of services, everything from just simply filling out a form to giving an agent a certain amount of wallet spend and saying, go off and figure out my life for me and spend the following on whatever. Everyone also likes to talk about bots going wild, right? And going rogue. And so I imagine if you are giving an agent a certain amount of money and telling it to spend in a certain way, instruction specificity can vary. But what happens if things go bad? Or what happens if you're simply dissatisfied with the choice that the agent makes? Whose fault is that? Like, where does the liability actually lie?

• 37:59Speaker 04

  I think this concern is quite overstated because, one, the agents can do a huge amount of useful work for you while there's still a human in the loop. And so imagine if Claude Code asks you, are you OK if I spend this amount? And you just have to hit enter? That's much better than the experience of signing up for a service and clicking around the web face and things like that. So you've still saved a huge amount of time, even if you're kind of reviewing the transaction. Similarly, again, the consumer use case, the way we suggest people visualize agentic commerce is you still have a human in the loop deciding, making the final decision of both what thing I buy and am I OK spending this much money? But the AIs can still be hugely beneficial as part of your shopping journey, even if you're as a human signing off on that transaction.

• 38:44Speaker 04

  And then you get a bit into delegated authority. It's kind of like, you know, we run a, you know, at Stripe, a large company, and we spend billions of dollars a year, and there's lots of delegated authority. You might say, what if you have one crazy person who makes a bad spending decision? And we occasionally have that. And, you know, how do you solve it? It's like, I don't know, give people spending limits on how much they can spend, and you, you know, whack them on the knuckles if they do something really crazy. And you just solve it with kind of sensible limits and delegated authority and approval process. And it's kind of the same with an agent.

• 39:12Joe Weisenthal?

  Well, this gets me to a question I wanted to ask about running a big company in the age of AI. Things are changing insanely fastly. Fast. Fastly?

• 39:22Tracy Alloway?

  Fast.

• 39:22Joe Weisenthal?

  Things are changing, I'm sorry. Things are changing extremely fast. And there are certain things that people were excited about last year that didn't fizzle out. And the same way, there are certain things that people got really excited about, even in December 2025, that became the next hot thing. For Stripe specifically or for a company, how do you think about, say, like, okay, here is a thing that we want to exploit. Here is a moment and we want to take advantage of it and we're going to build the thing for this moment. Versus we want to allocate resources for anticipating what's going to be the thing 24 months from now. Explore where this is going. How do you think about the sort of resource allocation between exploring and exploiting

• 40:05Joe Weisenthal?

  in such a fast moving environment from the corporate standpoint?

• 40:09Speaker 04

  I would say you need to be very flexible because as you were saying, if your information is three months out of date or six months out of date, it's just woefully old. And so we try to be pretty flexible. And I know there's AI somehow brings out a desire for thought leadership in people.

• 40:25Joe Weisenthal?

  Yes.

• 40:26Speaker 04

  Oh, my God. Everyone. Very grand pronouns, but yeah. And just, I don't know, like, we have more questions than answers and we're trying to figure it out as we go through. So that's one is kind of having the right level of humility. The second thing is you kind of need to have the, similarly, the right level of AI psychosis, that the dose makes the poison, where you need to really believe in the capabilities of the models. But you also have to be willing to reason about the limits. And so to give you an example, really amazing at writing codes and huge productivity uplift there. If you try to do anything, I don't know if you guys have tried to do anything like a financial analysis with the models. They're just horrible at numbers, innumerate. And they can kind of fool you because they can put together or something that they can build a really nice spreadsheet. But you're like, but the numbers just go completely wrong halfway through the spreadsheet.

• 41:11Speaker 04

  Oh, great point. You're absolutely right. And so you need to have kind of a bit of a fingertip sense for what the models are good at versus bad at. I kind of think of this in, you split up the company into the traditional, you know, this R and D, go to market and G and A. And if you think about the different domains, they work quite differently. Within engineering, engineers have always been passionate about tools and better tools and.

• 41:35Speaker 04

  Any kind of a half self-respecting engineer is very eagerly adopting AI. You don't get too many laggards. And so we have seen a huge amount of adoption within the software engineering at Stripe. That's going really quickly. I don't think we're at the end stage, but we're pretty like that machine, I would say, is pretty well set up to be in this self-improving loop. Because the people who are kind of doing the engineering day in, day out also think about how can I better automate this process? How can I use AI to to make it work faster? And so a lot of bugs that are fixed at Stripe, no one ever opens an editor for them. They just hit the fix this bug button in the interface and that's done identically. So that that's software engineering.

• 42:13Speaker 04

  On sales and kind of go to market, what helps you is that it is the most measurable domain inside of tech companies and companies broadly. And so you can reason about the specific productivity of a specific salesperson in a way that you can't with a software engineer or a lawyer or something where any kind of metric there is very subject to Goodhart's law. Whereas with go to market, it's measurable. And so we have seen at Stripe, at least our sellers are super into AI. They're adopting it very eagerly and you can't ascribe causality in the productivity numbers, but the productivity numbers are very good. The place where I think it's trickiest is within the other general functions. You think about legal and finance and risk and things like that.

• 42:57Speaker 04

  And there, there is a lot of AI happening, but it's just tricky because one, there's a huge amount of infrastructure work that needs to happen. It's like, okay, we actually have to get this financial data into a form where it's usable by the AIs. And we used to keep it under lock and key and now we need to kind of load it in a way that the AI can use. So we had a big infrastructure build at Stripe to make the data usable to the AIs, but also kind of keep it locked down appropriately and things like that. And then, like I said, the AIs are just uneven in which domains they are good at. And so if it is a coding problem or if it could be turned into a coding problem, very good at that. The public tax code and the public legal code, they're very good at that because it's text that they've been trained on.

• 43:36Speaker 04

  But working with, I would say, specific financial data at Stripe or kind of specific internal stuff that we have, that's just kind of harder to get good results out. It's not impossible and the models will improve a lot, but I would say that is kind of the trickiest domain to get great results.

• 43:49Tracy Alloway?

  So just going back to the beginning of this conversation, we talked about how the internet basically runs on commerce. And if the nature of that commerce is changing, you would expect some impact on the internet. We've been asking you various questions about that. But I'm just going to ask you very directly, what is your sort of broad vision of the internet in the world of agentic commerce?

• 44:13Speaker 04

  We're very excited for the intelligence explosion. And so in our pocket of the internet, we are seeing much more entrepreneurship happening. That shows up in the numbers. So to give you a sense, new business creation on Stripe in Q1 was up 71% year over year. That business generally is not growing that quickly. It's like the leading edge numbers are seeing much more business creation. You see this in other numbers, too. So the App Store, like, number of app launches was quite flat for many, many years. And now it's seeing kind of similar growth to that. And so there are going to be many, many fruits

• 44:54Speaker 04

  of the intelligence explosion. But we get quite excited about the idea that you have more people creating companies. And maybe you get more dynamism, right? We talked about some of the effects where, you know, you'll maybe see more price competition. If you work at a big company and you think, hey, the way we are doing this is really silly. I could do it so much better. The bar to you being able to quit the company and develop a competing better offering is now lower because you have more power available to you. You can recruit the intelligence that's available to you. And so our prediction is that you get more economic dynamism, which we're already seeing in our leading edge numbers. You know, we're seeing more startup formation. But we talked about this at Stripe

• 45:36Speaker 04

  Sessions, you know, kind of in a Kosian sense, maybe you see smaller firms and more of them because it's easier for them to coordinate each other.

• 45:44Joe Weisenthal?

  John, I have like a million more questions for you, but I'm aware of the time. So let's just leave it there. This was such a treat. Really enjoyed getting the chance to talk and would love to have you back sometime.

• 45:55Speaker 04

  Absolutely. Would love it.

• 46:08Joe Weisenthal?

  Tracy, I really thought that conversation was super interesting. I mean, just to start, there is a lot here. This is a big deal. I think where it's going to go, the question of whether just commerce directly, and then also your question of the internet more broadly. There's some pretty big questions and pretty big implications from which way some of this stuff unfolds.

• 46:29Tracy Alloway?

  Yeah, and I'm glad that John appreciates the enjoyability of scrolling.

• 46:34Joe Weisenthal?

  The human in the loop.

• 46:35Tracy Alloway?

  Yeah, well, yes, absolutely. I do have questions about, I guess, discoverability when it comes to agents. So everyone by now knows the example of you go on Netflix. The first video or movie TV series you ever watch is incredibly important because the algorithm sort of builds itself around that one choice. And if you watch something stupid, then forever and ever, it's going to like pinpoint you has this one demographic. So there is a tendency for algos to sort of cluster among like recognizable patterns. So it becomes harder to discover new things, new products. I will say some algos obviously do it better than others. YouTube's algorithm, I find like actually really phenomenal for resurfacing or for surfacing new things.

• 47:19Joe Weisenthal?

  Well, within LLMs itself, I find memory to be a very double edged sword, which is on some level, I do think it's more useful when it knows a little bit about the context of the user. But there'll be times when it'll shoehorn any, like you did a query six months ago and it'll try to bring it back around to that. I think there's a lot there. I think there's a lot there with the future of advertising. We're just setting us at what is the equivalent of SEO in the LLM? We should probably do an episode from the perspective of retailers that are really having to think about how they surface within.

• 47:51Tracy Alloway?

  Totally. So that, that in itself is a huge shift. If you're a retailer and now you're trying to target bots as well as humans. And then the overall question of what happens to the internet in this new world, like. I tend to be very cynical about the overall direction of the internet and just assume that every new advance in technology is going to make it worse. But like, you could see a future where the ability to do seamless microtransactions basically means that like everyone starts charging for their content for their APIs. And so you actually have to pay a fee to be on the internet.

• 48:26Joe Weisenthal?

  This is what I mean, like, the end of freeism roaming, I think, is an interesting question. I also just personally, I find it very validating that like, I'm not crazy that actually like being able to do something in a dome, like buying a domain name is something that people, other people thought needed to be solved. You know what I'm saying? So like, some of these things seem very specific that Stripe announced in the last couple weeks, related to both the domain name question, they're related to being able to pay an API directly, rather than go to a website and enter your credit card and stuff like that for credits or whatever. I found these things to be very annoying and big deals. And I'm sort of glad that I feel less crazy. Like, actually, these are annoying things within the new contemporary landscape.

• 49:09Tracy Alloway?

  Absolutely. And speaking of annoying things, I also feel like a big chunk of the future is going to be bots, just like negotiating with each other. And I've already heard in the insurance sphere, you know, you've heard of insurers using AI to like bulk deny claims, right? And then I've heard of new AI startups or existing companies using AI to contest the insurers.

• 49:32Joe Weisenthal?

  Yeah, of course.

• 49:33Tracy Alloway?

  Pushback. And so it just feels like it's just going to be bots, like.

• 49:36Joe Weisenthal?

  The only moneymakers are going to be chip companies in Korea, because they're everyone's going to be having to get more powerful chips. And old boomer landlords in San Francisco, because the employees of OpenAI and Anthropic need a place to live.

• 49:52Tracy Alloway?

  And healthcare.

• 49:53Joe Weisenthal?

  Yeah.

• 49:54Tracy Alloway?

  All right. Shall we leave it there?

• 49:55Joe Weisenthal?

  Let's leave it there.

• 49:56Tracy Alloway?

  This has been another episode of the Odd Lots Podcast. I'm Tracy Alloway. You can follow me at Tracy Alloway.

• 50:01Joe Weisenthal?

  And I'm Joe Weisenthal. You can follow me at theStalwart. Follow our guest, John Collison. He's at collision. Follow our producers, Carmen Rodriguez at Carmen Erman, Dashal Bennett at Dashbot, Cale Brooks at Cale Brooks, and Kevin Lozano at Kevin Lloyd Lozano. And for more Odd Lots content, go to Bloomberg.com/oddlots, receive a daily newsletter and all of our episodes. And you can chat about all of these topics 24/7 in our Discord, discord.gg/oddlots.

• 50:27Tracy Alloway?

  And if you enjoy Odd Lots, if you like it when we talk about the future of the internet, then please leave us a positive review on your favorite podcast platform. And remember, if you are a Bloomberg subscriber, you can listen to all of our episodes absolutely ad-free. All you need to do is find the Bloomberg channel on Apple Podcasts and follow the instructions there. Thanks for listening.

• 51:17Speaker 06

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• 51:47Speaker 06

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• 51:56Speaker 07

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• 52:12Tracy Alloway?

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