This Week in Startups
00:28:16 · Patrick Collison, Alex Wilhelm, Jason Calacanis
[00:28:16] S4: That's right. [00:28:16] S3: Alright. So, Lan, here we saw Patrick talk about, I I would say billions of GMV. I think he's what he's talking about there. Thousands of businesses, 700 employees. Okay. So I went through and I pulled out the Stripe numbers from both the end of 2025 and the midway point of 2026. So it's a little bit different as you might imagine. In 2025, the company did drop the number. They processed $1,900,000,000,000, so not billions, but several trillion dollars worth of GMV, and that was up 34% compared to the year before and worked out to about 1.6% of global GDP. Now, if you look forward to the first half of this year, Stripe is now processing about 2% of global GDP. They announced 5,000,000 businesses on the platform, and the revenue in the first half of this year was up 41%. So what I just love about this is here we have a successful founder of entrepreneurs doing great things, really good company scaling, hundreds of employees, really proud of the numbers, and it was just an absolute pit squeak compared to where it is now today. [00:29:17] S2: Very impressive.
00:29:17 · Jason Calacanis, Lon Harris, Alex Wilhelm
[00:29:17] S2: Very impressive. [00:29:18] S0: I mean, it's also interesting how disclosure and transparency shifts over time. When Stripe was still up and comers, startup, you know, underdog, they were like, we don't we don't really like to give out metrics. Like, we don't... We we gotta we gotta protect what we're doing, and we don't wanna prying eyes. And, you know, obviously, today, they're publicly reporting they've got valuations, and, yeah, every... And we know a lot more about what's going on inside Stripe, but also the Collisons themselves are routinely on podcast. They've got, I think, the cheeky pint. They've got their own. There's a there's a lot more discussion publicly about what's happening at Stripe, the larger that they've grown over the years. [00:29:57] S3: Oh, absolutely. In fact, I believe they built the cheeky pint set just for that show. So that might show just how the scale has changed from going to someone else's event to making your own fake pub so you can have your own podcast, I think shows the biggest [00:30:09] S0: scale of the company. You mean reality TV? That's finding out that the pawn stars pawn shop is not a real pawn shop. Like, you're you're [00:30:15] S3: It's like learning that the real housewives of Rhode Island are not really, indicative of the average, housemaker in the state. You know? Chalkyly enough.
00:30:15 · Alex Wilhelm, Lon Harris
[00:30:15] S3: It's like learning that the real housewives of Rhode Island are not really, indicative of the average, housemaker in the state. You know? Chalkyly enough. [00:30:22] S0: I don't think anybody thought that. I think he might have been the only one who thought that. Alright. So, I do think we should move on to our next clip. Jason tried desperately to get Patrick to bag on PayPal, one of the Stripes' key rivals back in 2017. Of course, Patrick did not take the bait. Particularly funny to look at now, with all of the PayPal, Stripe acquisition talk of late. These two companies obviously have remained in one another's orbit and of interest to one another ever since. Let's take a look at this clip.
00:30:54 · Jason Calacanis
[00:30:54] S2: AI has changed everything about how software gets built, and that includes how you hire the best engineers and developers. It's not about lead code rankings anymore. No. You need to know how well candidates understand working alongside AI or maybe even SI, superintelligence. You need to know how they're gonna direct these agents, evaluate their output, and most importantly, look for mistakes and make sure that the code is tight before you deploy it. And our friends at g two I can help. G two I has been recruiting software engineers for over a decade, and their vetting process has evolved and adjusted to how engineers actually work today. They're not just asking candidates if they use AI. Well, of course, everyone's using AI. My mom's using it. My brother's using it. My kids are using it. No. G two I is evaluating how well they use AI tools to boost their productivity and effectiveness at writing code, at deploying. The focus stays on technical judgment. You don't want a staffing agency that looks for AI first on a resume and calls it a day. Nope. You need somebody who tests for it. The best way to know if somebody is good at a task is to watch them do the task. So go to g2i.co/twist. Book a call and find out how g two I vets their own engineers so you can confidently hire them in just days, not weeks or months. That's g2i.co/twist. PayPal was just horrific to deal with. Every time I tried to get into my account, didn't work. Every time we tried to accept money from people, it didn't work. Everybody would tell me the same thing. Do you have PayPal? I have one. Oh, can I tell you? It's locked. And I can't get anybody on the customer support line, and I have $2,000 in there, but I can't get into my... Anybody have customer support problems with PayPal, raise your hand? It's a whole lot. He just raised their hand. It was just like this very... They seem to have figured it out since, but there was this very dark period where nobody was running PayPal. Was that what led you to have that opportunity to zip in there?
00:32:48 · Patrick Collison
[00:32:48] S4: Well, look, I don't want to speak ill of any particular company, but, we heard from our friends, and from people around us building companies and so on, that some of the companies they worked with were occasionally suboptimal. But you know, it's easy to kind of focus on PayPal, I think that's actually, know, obviously they're pretty large and established and so on, but it certainly was not just them, and that sort of when we look to our friends, people we knew running companies and so on, and most actually weren't building on PayPal. Maybe perhaps in part for those reasons or others, or I don't know, but most of them weren't. Most of them were building on these legacy players, like they were working with banks, they were working with gateways, processors, of stuff like this, right? And they were sort of looking to buy essentially a technology service from them, right? I mean, they wanted APIs for sort of turning credit card numbers or whatever the payment instrument was into money in their bank account, right? That's kind of the service they were looking to buy. But these companies, which were, again, providing an AWS like service in terms of the core nature of it, you know, they were not equipped to be AWS. They were not equipped to sort of provide flexible APIs or to, you know, to to to enable people to really iterate.
00:33:53 · Alex Wilhelm
[00:33:53] S3: I absolutely love that clip because there's a bit of a historical echo here, Lon. I... I'll let you talk about the acquisition that didn't happen in a second. But if you go back to 2017 and you look at the stock price of PayPal at the time, it ranged from about $40 a share at the start of the year all the way up to about $80. But it was about 55 in the middle of the year, and it's currently at about $55 per share. So at the time, PayPal is probably worth about what it is now, $4,850,000,000,000 dollars. It's gone up. It's gone down. It's back to where it was. In the meantime, Stripe has just been churning along.