Pregame Your Launch Before Your App Exists (w/ Amanda Bradford) | E2355

This Week In Startups is made possible by: Odoo: https://odoo.com/twist G2i: https://g2i.co/twist Rippling: https://rippling.ai/twist Plaud: https://plaud.ai/twist Today’s show: Amanda Bradford’s “launch party” for her dating app The League actually extended for months. She “pre-gamed” the app’s formal launch with months of mixers, boat parties, and free events, where the only ticket required for admission was having the app on your phone. By launch day, she had a massive wait list, and still just let in 500 people, who ensure maximum buzz (and FOMO). At LAUNCH’s first-ever Tactical & Practical live event from San Francisco, Amanda walks the crowd through how she built a vetted, two-sided dating marketplace as a solo founder, eventually getting prominent enough to attract the attention of Match Group. (She sold The League for ~$30 million in 2020.) Hear exclusive tips you won’t get anywhere else, like how Amanda used a “fake paywall” to gauge willingness to pay for subscriptions, and how to time your rate of expansion into new markets. Plus, an all-new Flashback segment, featuring Alex and Lon looking back at a classic 2017 interview between Jason and Stripe’s Patrick Collison. Guests Amanda Bradford on X: https://x.com/amandabradford Book a Call with Amanda: https://intro.co/amandabradford The League: https://www.theleague.com/ Patrick Collison on X: https://x.com/patrickc?lang=en Stripe: https://stripe.com/ Relevant Links: The League was called "elitist." Its founder says that was never the case (CNBC): https://www.cnbc.com/2023/10/20/founder-of-the-league-on-dating-ambition-and-that-viral-ad-campaign.html Alex Wilhelm’s Cautious Optimism: https://www.cautiousoptimism.news/ TWiST E723: Patrick Collison (2017): https://www.youtube.com/watch?v=P-NepiMQGvY Timestamps: 0:00 Amanda Bradford on building The League 4:30 Hand-reviewing early applications 6:40 Building an MVP with a rented co-founder 8:56 The VIP approach 13:10 Why Amanda only let in 500 people 15:44 The “Heavy Hitter” fake paywall test 16:44 Odoo: The all-in-one business platform. Your first app is free! Get started today at https://odoo.com/twist 17:46 Why live events are the real unlock 21:35 Controversy as a hook 24:22 Flashback to Patrick Collison in 2017 25:13 Plaud: If your work depends on conversations - interviews, meetings, calls - you need a Plaud NotePin S. You can check it out at https://plaud.ai/twist and use code TWIST for 10% off! 28:13 Stripe: Then vs. Now 30:53 G2i has been recruiting software engineers for over a decade. Go to https://g2i.co/twist to find out how G2i vets engineers, and can help you hire them in days, not weeks. 32:17 Why did PayPal stay PayPal? 37:50 Problem, not a product 44:33 Thanks to our partners at Rippling! Head to https://rippling.ai/twist and get the only AI built to give you full visibility across your startup and take complex actions across your entire business. 45:46 The outage nobody noticed 51:00 Why persistence beats pivoting 52:13 What’s left before a Stripe IPO? Subscribe to our newsletters on Substack: TWiST: https://twistartups.substack.com/ TWiAI: https://www.thisweekinai.ai/ TWiVC: https://thisweekinvc.substack.com/ Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp Follow Lon: X: https://x.com/lons Follow Jason: X: https://twitter.com/Jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis Thank you to our partners: Odoo: The all-in-one business platform. Your first app is free! Get started today at https://Odoo.com/twist G2i has been recruiting software engineers for over a decade. Go to G2i.co/twist to find out how G2i vets engineers, and can help you hire them in days, not weeks. Thanks to our partners at Rippling! Head to https://Rippling.ai/twist and get the only AI built to give you full visibility across your startup and take complex actions across your entire business. Plaud: If your work depends on conversations — interviews, meetings, calls — you need a Plaud NotePin S. You can check it out at https://Plaud.ai/twist and use code TWIST for 10% off! Check out all our partner offers: https://partners.launch.co/

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  Hey, it's Lon. Welcome back to another episode of This Week in Startups. We've got an amazing two-parter for you. First up, from our recent San Francisco Tactical and Practical Event with Launch, we've got Jason presenting an incredible presentation from Amanda Bradford, The League. She's going to walk you through how she used guerrilla marketing tactics and stuff that wouldn't scale in order to grow and find her first customers for The League signing on a foundation of users before the app even launched. It's an amazing talk about how your pre-gaming and your marketing and your event planning has to start way before the app is actually ready to launch. Then, we've got the latest edition of our flashback segment with myself and Alex Wilhelm.

• 0:44Speaker 00

  We're going through a classic interview with Patrick Collison of Stripe. It's very insightful and it's about how Stripe has both changed over the years and how they've stuck to their guns and sort of not becoming a public company and why they've stayed private. Really insightful, lots to talk about with Stripe. So stay tuned right now for a new episode of This Week in Startups with both of those amazing segments.

• 1:08Speaker 01

  Hi, everyone. I'm Amanda Bradford. I built a dating app, sold it to Match Group in 2022. So I'm going to tell you a little bit about my story and how we launched because I think that's kind of the most important part. And especially from what I understand, most of you guys are early-stage founders. So feel free to talk to me afterwards if you want to talk more about the M&A and the scaling and kind of all that stuff, but I'm going to focus on the early-stage story. So just quickly, what I'll go into, a little bit of who I am, what our pitch was, how I built it, and then end with some tactical advice. My story, I went to business school, which I joke is like going to college, part two. And it's very social experience and you meet a lot of people. I think our class of 300 had like 30 couples that started out of that, you know, very tight cohort of people.

• 1:51Speaker 01

  And so one of the reasons that I kind of thought to do this was when I was graduating, I was like, wait, this is crazy. I'm in this pool of amazing, like very eligible people, and now I'm in the real world and they all go away and now you're back to like Tinder. So I was like, why don't I just try to create the kind of the same sort of very close-knit, very ambitious, very, you know, educated cohort with an app so that people don't have to go to business school to meet people. And I, my background was in, I like to call myself like technical enough that engineers don't like me, but not technical enough to do their job, at least in the former days. And so I, you know, I did HTML, JavaScript, CSS, but I wasn't building APIs. So I, I was not like the last, the last speaker who had a co-founder. I was a solo founder.

• 2:36Speaker 01

  So shout out to anybody who's solo founding. Now is the day that you can actually do it a lot easier than in my day. So The League, if anyone hasn't heard of it, we built our product on LinkedIn verification. So we were the very first dating startup to use the LinkedIn API and also to have an admissions-based process where not everybody got in. And that was very controversial at the time. And I spoke about this a little bit, but you know, I think the kind of lightning bolt for me was that it's so easy to meet people when you're in these college environments. You don't really need dating apps. That's why a lot of people pitched me on dating apps for college kids. And I'm like, just go outside, like knock on someone's door on your dorm. It's really not that hard, but when you're actually in the real world, all that stuff goes away. All the infrastructure goes away. You hope to find people at a bar. No one's going to bars.

• 3:20Speaker 01

  You hope to find people at a gym, but no one wants to talk to anybody at the gym. So it's, it's kind of a terrible environment for meeting people, especially when you compare it to what you just came from and where I had just been. So what I did is I created the same kind of thing. I was like, okay, Stanford is very selective. They only accept like one or two or 3% of people, depending on if you're legacy or not. But my goal was to just have a very vetted community of people that really wanted like a serious relationship. So this was not for the one-night stands. It wasn't hot or not. It was, you know, let me find serious people that are kind of seriously interested in dating. And so the way I designed it was happy hour, which in retrospect is actually a very difficult technical design challenge because we had the entire user base come at 5:00 PM and we would give them three matches or five matches at 5:00. So that was our tagline, five at five.

• 4:05Speaker 01

  And so this was again, you know, contrast this with Tinder where you're just swiping for hours and you're like, you have infinite homework was what I felt like on the other apps. And I was like, I just want one that gives me some a day. I don't have to stay online. You know, we weren't trying to get people to engage and be on the app for 30 minutes. We just wanted to give them very good matches. So it was a little bit very, very different than what the current kind of dating app environment was, where it was sort of all you can swipe. And then what we also differentiated with was besides LinkedIn, we also had the admissions-based applications. So I review, I personally hand-revied every single application and then I hired my best friend to do it. So we joked that she worked the door while I like worked the product. And then we also had a, one of our big features was that we wouldn't match you with people you worked with.

• 4:48Speaker 01

  So I had been doing an internship at Sequoia where I was the only woman. And the last thing I wanted was for all the people that I reported to to like see me on a dating app. So we built it because we used LinkedIn. We could say, don't show me anyone else at Sequoia or anything like that. So that was, you know, a feature guys didn't care about as much, but women really cared about. So, you know, find your niche and find your like power users. And women really gravitated towards the feature that they, you know, if they'd managed a group of people and there were men, they don't want their, their direct reports seeing them on a dating app or vice versa, their, their boss. And then we also did a lot of events and parties, which I'll go into, but that was a big differentiator because we were kind of doing offline back when no one was doing offline. And people really liked the fact that we, you know, they could meet people in real life through the app.

• 5:30Speaker 01

  So here's some of the taglines. We, you know, we really leaned into being like, we are for the ambitious. We're for the picky, you know, it's better to be single than settled. So we have a lot of, you know, kind of brand. We worked really hard on making sure the brand was like very much for people with high standards. And this is our demographic side when we sold. We're, we're much bigger now. But, you know, we, we really focused on people, you know, I had come from an MBA program. So that was obviously my like founding wedge was MBAs. My, my, one of my investors joked that like the first five weeks on the app, he was like, you should just call this MBA date because it's all these MBA women. So go really, go really deep and narrow at the beginning. So ours was sort of the advanced degree people. And then we got finance on it. We got, you know, marketing people on it.

• 6:12Speaker 01

  So we had a lot of tech lawyers, people with advanced degrees and MBAs, of course. And, and we, you know, people were like, oh, it's for the Ivy League. And it wasn't actually for the Ivy League. I mean, I went to Carnegie Mellon. That's not Ivy League. But because the way we named it and the sort of the brand we built, people kind of associated with the Ivy League, which I actually thought was a good thing because we can associate your brand to something that people really understand readily. It helps them get the message across very quickly without having to be like, how is it different? So how I built it, this was a, this was a hard, you know, a hard slog when you're a solo founder, but I basically found an iOS engineer. He built, we only built it in four months. And during those four months, I was basically QA-ing the product, finding bugs, shipping, you know, sending it back to him to change things. And then I also pre-gamed our SF launch.

• 6:57Speaker 01

  So what I mean by pre-game, if none of you guys have been to college, but that was one of the fun parts of other parties is everybody got together to pre-game before the party. And we always joked that the pre-games were more fun than the party. And so that's sort of what I did for the SF launch. I didn't have a big expensive party. I didn't think that we had to have that, like, you know, people coming out of a cake or whatever. People do at these crazy launch parties. We, I just actually had a lot of series of small events beforehand and kind of went door-to-door to collect people on my waitlist. And then we, by, by doing that and by getting the word out beforehand, we even got some press before we launched, which was great because then I could even choose from, you know, the, the kind of the best of the best that had applied for the founding cohort. So you want to build your waitlist before you launch, especially if you're doing a double-sided marketplace. Like I know that I'm a consumer person. I'm sure a lot of you guys are doing B2B,

• 7:42Speaker 01

  but all these things hold for any double-sided marketplace, whether you're in B2B or consumer. Again, you, you never want to have the empty room problem. And so that was like, I really focused on those five months to make sure we did not have the empty room problem in San Francisco, which is where we launched. So you can see here, this is my very first like prototype that I handed to a developer. It ended up being a different developer because I tried going out. I outsourced it at first and then outsourcing doesn't work, at least in my experience. So then I hired someone to sit next to me and actually be kind of like a rented co-founder. He had an equity stake and everything like that, but he was really just there to build the app and give me a proof of concept. And then that was sort of our, our contract was when he gets me into the App Store, his equity vest. So it was, you know, I kind of joked that, yeah, I rented a co-founder for those five months.

• 8:25Speaker 01

  But we, we went really fast. So you can see, you know, I, we only spent five months building the app. And now, you know, in today's day, that's probably like two months, if not even, maybe even shorter. We spent a lot of time on the onboarding before the user gets in. So when they were, you know, when we were still collecting waitlists, you can see I had the countdown, how many women, how many men we needed. People were inviting their friends so they could get the spot. So we showed how selective we were being and it created a sense of urgency when people saw that screen that they should say, oh, wow, I mean, there's only, you know, 50 slots left. I should tell my friends to get in it. And so building your founding user base, this is the, you know, this is the hard part, but most important part, especially again for a double-sided marketplace. But I did the VIP approach. That was where most of my time went, where I was going to tons of events. You basically become, you know, a socialite. If you're not one already, become one

• 9:09Speaker 01

  or find a co-founder who's going to be a socialite. And you're just going out, you're asking people to give feedback on your onboarding. That was my most common way. I went up to people. I said, I just wanted to see like, what do you think about this onboarding? Would you do this? What do you like about the current apps? What do you don't like about the current apps? And they feel really special because they're, you know, you're asking them for their feedback. They're almost being like a design partner to you. And so I called all those users founding members and they were, you know, I was like, if you, yes, I'll give you founding member credit and I'll, you know, you'll get first, uh, first dibs at the, you know, when we launch, you'll be in the first cohort. And so the like door, that's kind of, I call that door-to-door sales. And then I had a bunch of parties, so I wasn't always saying, hey, download my app and just give me feedback. I was like, oh, hey, I'm having a MBA mixer. I'm having a Fleet Week boat party.

• 9:54Speaker 01

  You guys should come. And to do that, you need to have the app on your phone to do that. But I don't, I didn't tell them that until you're at the door and then you have Have to hire someone very good at the door that isn't, that's gonna hold, hold that line and say, you know, you need to have the app on your phone to get in. Um, so I can go and do a little bit of, um, what I did. See here, you can see some of all the different events I did. I did girls feedback and wine night. I did a shopping event after hours. All these things were free. The, um, local business owners. Were like, sure, we'll open this store an hour later. If you're gonna, you know, commit to like $300 in sales. And of course. People, you know, I had like 60 girls there. We spent way over $300. Barry's Boot Camp did the same thing. They had a, uh, they had a. A time slot that nobody was booking, so they gave it to me for free and then I booked it out.

• 10:36Speaker 01

  Blue Angels Boat Party is really hard to get on a boat during Blue Angels, so I rented that like three, four months in advance and then got, you know, I actually charged people $300 for that. Event. So we didn't, we actually made a couple of grand on that event. So I didn't really spend that much money. On these marketing events, like open bar, I'd say, okay, I'll, I'll buy everybody the first, first, first drink free and then it goes on your card. So it's, it's, you know, you can do these kind of on the, on the cheap. And we actually did all this and then I closed 2 million after we launched. So again, it's in consumer especially, it's very hard to close. Funding without traction before you launch. If you can do it, you're a rock star and, you know, good, good for you, but for the most part. People need to see that users are using it and they like it and they're sticking around. Um, and so that was a big, big.

• 11:20Speaker 01

  How we closed in January was showing that we, you know, people in San Francisco were actually liking it. Here's some of the events I did. I can scroll through these really fast because I'm getting low on time, but. These are all the different events I did. Again, this is all before the app goes live. So just remember that. It's like, we're building the waitlist, building your word of mouth, building. Your kind of founding design partners, whatever you want to call them, founding members. And then we did a lot of press and partnerships today in today's land. This would be influencers also. And here you can see some of the emails I sent to get the word out. So this is my friend who went to Wharton. I didn't go to Wharton, so I had no one to contact there. So I asked him to forward that to his Wharton group of. 350 people. So he did that and then I got another, you know, I got all the Wharton people using it and then.

• 12:01Speaker 01

  These are the press outreach that I did before we launched. This is bold italic. I don't even know if they're around anymore, but. You know, things like Refinery 29, TechCrunch, um, Business Insider. So we, you know, I had friends that had worked in PR and they told me. You know, you need to, here's how you pitch. Here's the people you need to pitch. Um, and there's people that write about dating and you should contact those. So I probably wrote about 30 of these emails and this is very much too long. But it is my first one. I was early days, so I would have shortened it down to like probably a paragraph now, but. You can see at least that, you know, you're kind of telling your story to the people. Um, and trying to get as many people to write about it when you launch. And we did, we got TechCrunch, we got, um, I think that one on the right is Business Insider. But you can see they, you know, everyone seemed to like the angle of, you know, the very elite elitist dating app, which.

• 12:46Speaker 01

  You know, in a way it was a double edged sword because then some people felt like they weren't, um, eligible for it if they didn't go to a fancy school, but. Most of the time they'll, they'll sign up anyway because. Who doesn't want to, you know, be in an exclusive group of smart, educated people that want a relationship? So it did better, you know, it was more good than bad, but. That's definitely, press will take your, we'll take your pitch and make it their own. That's for sure. So on launch day, we opened our gates. I only accepted 500 people. Keep that in mind. In context, we started on 419 people. So similar to the guy who was just before me, he only had, you know, get 10 users. It's like, it's really better to have. 500 people that like are obsessed with your app than trying to open it to like 5,000 people and figure out what, what you're doing wrong. So small is better. And then we just rinse and repeat. We did these all over.

• 13:30Speaker 01

  We were in San Francisco for six months, then we launched New York, six months into San Francisco, and then we were in New York and San Francisco for a full year before we. Launched LA and that, we didn't even have monetization at the beginning. So we added monetization. In that period of time between New York and Los Angeles, but we did, you know, parties at the best rooftop bars. We would work with Soho House. We did partners with, uh, partnerships with the Equinox because they have a place in every city we went to and they would let us have parties there for free, as long as we brought people that weren't Equinox members. So. Again, the partnerships are a really big, um, big help, especially if you're trying to do things on the cheap at the beginning. And these, eventually, once we did stuff with Equinox and we did stuff with Soho House, all these, all these people came inbound to us. So they were like.

• 14:09Speaker 01

  HBO wanted us to do a party for one of their shows. We did a Netflix party for one of their movies that they launched and we helped launch things. So this was a. Again, once people see other good brands next to you, they'll come to you. And then we grew, you know, we weren't, it wasn't exponential growth. It was hard, you know, hard growth, but we, um, we kind of rose. Consistently through the, you know, daily active users and signups and then, um, eventually we launched in 155 cities. The big takeaway is launching other cities. So a lot of founders come to me and are like, oh, we want to go to New York. We want to do this. We want to do this. We want to go international. And I'm like, no, no, no. You still have so much TAM in New York or San Francisco, wherever their first city is. I was like, you need to get better penetration in your first city before. Expanding. Um, and I think you can, in retrospect, we launched 155 cities. If I had to go back in time, I would have capped it at 20 because.

• 14:55Speaker 01

  The revenue from the 21st through the 155th city was negligible and added more complexity to operations. Hiring, I couldn't find a perfect co-founder. If you can, you're, that's amazing. If you can't, just go forward. Don't wait for Mr. Right. Fundraising, same concept with fundraising, uh, show that you have skin in the game before asking for money. So if, if you don't get a yes, say, cool, this ship is, this ship is sailing rather, whether you're in or not. And so I think my investors particularly liked that I was, I was launching already. I was gonna launch, you know, I needed, if they gave me money, that's great, but. I wasn't, you know, like stuck if I didn't get fundraising. And then press, and I would put influencers on this now too, are your best friend if, because they'll do it for free. It's, it's earned media. Um, none of our press costs us money.

• 15:38Speaker 01

  If you can get influencers to tweet about your things or post about your things for free, that's amazing. So try to, you know, do these targeted pitches to these people that have this distribution. And then monetizing, we didn't monetize the first year and a half, but what I did do is a smoke and mirrors thing where I said, do you want to upgrade to heavy hitter? If so, click the button. And then I just said, we charged your card. Now you're a heavy hitter and we gave them the features, but we didn't actually, my engineer didn't even know how to do, uh, you know, billing or anything at that point. So it was a total. Fake out, but we could then see, okay, about 15% of people pushed the button, said they were willing to pay $15. So then when I went to go fundraise, I could say, we did a, you know, we did a, a test.

• 16:16Speaker 01

  And we know that 15% of people, so maybe 13% in reality, um, would, would be up for like a membership fee. So that, that helped people, it helped the investors. Feel okay with the fact that we could monetize even though we hadn't. And then rebuilding your MVP, start earlier than you think. Um, we had a lot of kind of scaling issues when we went to New York and that was part of why we waited so long for LA. But, um, it was definitely an MVP. So, um, as soon as you know that you're getting traction, just. Realize that that's a project you'll probably need to take on.

• 16:45Jason Calacanis?

  Odoo is the all in one management software that brings everything you need into one easy to use platform and founders already know. It's going to save a lot of their valuable time, but I want to spend just a few minutes exploring one of these real apps with you. That you get access to when you sign up for Odoo. Let's check out Odoo Discuss. This is where Odoo brings together all of your text conversations, your voice notes, your documents. And any other updates you have into one easy to scan dashboard. No more deep dive searches trying to find the specific message you remember reading the other day. Or flipping between 18 tabs to make sure every member of the team is up to date. Nope. Odoo helps you record and transcribe meetings and calls right in your sidebar with results.

• 17:27Jason Calacanis?

  Automatically updated once they're ready. Yes, Odoo Discuss built into the platform. So if you're still cobbling together your back office across five different apps. Get started today at Odoo.com slash twist and your first app is free. That's the right price. That's O D O O dot com slash twist. Give it a shot. Let's do an exercise here. If it's a dating app for elite customers. Yeah, everybody wants to meet them because they can afford an Equinox or they can afford, uh, being a member of Soho House. They can afford a John Vervatos outfit. So let's double click on this because the real live events is I think the, the real unlock here.

• 18:06Speaker 01

  Yeah.

• 18:06Jason Calacanis?

  And you could kind of expand it and make it the whole talk. So that's my ask for the next one. So real world, driving customers, building community and just getting pressed. There's something really great there. Do it for. Replit, a, a bunch of developers and then I want you to do it for, uh, the Salesforce. It is a SaaS product, right?

• 18:30Speaker 01

  Yep.

• 18:30Jason Calacanis?

  So how do you do it for those two groups of people?

• 18:33Speaker 01

  Marco of the book on Dreamforce. I used to work at Salesforce. So that was a, a big, a big part of his strategy is getting everyone together and they could talk to other people that also were admins of Salesforce. So he had, you know, he had like the first sort of developer, developer meets sales conference together. For Replit, I mean, I think developers like to meet other developers. And it's similar to like how NBA singles wanted to meet other NBA singles. You find sort of a niche of the developers that maybe it's hard to find. People that are specialized in this one thing and you could create a meetup for them or, I know, you know, like a startup hackathon or something that they get a hundred thousand dollars or. If you're a startup, maybe it's $10,000, but you get, you know, some sort of award and a trophy.

• 19:12Speaker 01

  But I think, yeah, it's finding what those, that group of people like, what their need is around, like who they're wanting to connect with that they can't. Maybe it's investors and. Developers that want to meet those people. And so then you bring in, you ask Jason to see if he can bring in some investors that want to come to the event. So, you know, use your network, but find out like what it, what it is that they're, they're not getting. And for our demographic, it was, they weren't getting like curated sort of mixers. You were going to a bar and everybody was either in a relationship or too old or too young. It was like the Goldilocks thing. So if I could get everybody who's like same age.

• 19:43Jason Calacanis?

  Ah, so this is key. The hit rate in it. So if you're here. Is anybody in the room not a founder? Anybody here not a founder?

• 19:53Speaker 01

  Okay. Oh, good. We'd have to kick you out.

• 19:56Jason Calacanis?

  People on my team are investors. Um, so. It is, if you, if you're here and you're talking to somebody, they're 100% a founder. That's actually kind of a great thing. So now I guess the way I can make this better is I could tell people I'm going to have 75 early driven founders here and I could offer to have 10 investors.

• 20:14Speaker 01

  Early stage because it's hard to get early, find early stage.

• 20:16Jason Calacanis?

  And then that could make the post networking even, even better. But so, okay, I'm unpacking it. Step one.

• 20:23Speaker 00

  Everybody in the room has to be a match, so to speak. That's one thing.

• 20:29Speaker 01

  Yeah, I mean, I guess in the like target demographic of what you're going after, if you're going after, I don't know, rock climbers or something for some outdoorsy app, then yes, you would want to.

• 20:37Speaker 00

  Okay, now, how do you get it to convert to a press hit? And how do you get it to convert to a customer? Let's unpack those, and we have a good example, I think we're working here, which is, you know, say, Replid or some dev tool. You got the hack.

• 20:52Speaker 01

  Just give me the hardest one, dev tools.

• 20:54Speaker 00

  Well, that's what I was trying to do. I mean, if you did it for, if I asked you to do it for a probiotic soda, that's also pretty hard.

• 21:01Speaker 01

  Yeah, yeah, yeah.

• 21:01Speaker 00

  So do probiotic soda.

• 21:02Speaker 01

  So I mean, we, so our example for us was we, you know, we would do some PR stunts. Like, we had a helicopter, we had a party in Montauk in upstate New York, and we had, we flew people out on Blade, which is this like, you know, elite helicopter that people take to the Hamptons. And we put three, uh, three dates, three, three blind dates on that. And then we invite, you invite press. So that's the, that's the trick is you got to invite press to your party. Obviously, give them a free ticket. Tell them there's going to be all these interesting people that they're going to cover. Maybe if you have some sort of out there thing that might be controversial, it's good to kind of mix that in. Maybe you have, I don't know, Replid is doing something that, I don't know, they're going to copy OpenAI or they're going to go head to head against.

• 21:41Speaker 00

  That would be actually a good one, if you add a little controversy. This, what is, um, not distilling or deconstruction, but a reverse engineering.

• 21:51Speaker 01

  Yeah.

• 21:51Speaker 00

  Is it reverse engineering? Is there a better term for it?

• 21:55Speaker 00

  Distilling.

• 21:55Speaker 01

  Yeah, that's a good example. You could have like.

• 21:57Speaker 00

  You could be like, oh, we're going to have a distillation of Photoshop, best distillation of Grand Theft Auto or something as a competition. And you could actually watch people distill a piece of software.

• 22:07Speaker 01

  And then the best hit will be like Silicon Valley engineers.

• 22:10Jason Calacanis?

  Distills Photoshop, kills trillion dollar company.

• 22:12Speaker 01

  Meet up together to overthrow the rest of the tech industry and it's us against big tech.

• 22:17Speaker 00

  All right, so I think this was too easy for you. Do prob, the probiotic soda. It's make it hard.

• 22:22Speaker 01

  I guess, I guess you would, you know, you'd find the people that are really into the probiotics and have all this.

• 22:26Speaker 00

  That's health, healthy people.

• 22:28Speaker 01

  Well, yeah, not everybody believes in all that stuff, but, um, I would, yeah, you would find your influencers that focus on this space, right? Obviously invite them if you can, but if you want to have someone that has a talk about, maybe there's different, there's, you know, different schools of thought on probiotics. Should it be in a drink? Or maybe it should be in an injectable? Maybe it should be in a pill? And are there new pills coming out that think the soda has too much sugar in it? Or whatever it might be. And so I think having, again, like fostering debates and like more of a, I don't know, like a, what do they call it? A salon of where people are exchanging ideas that are like maybe a little hot takes, I guess, I would say.

• 23:04Speaker 00

  Yeah, like actually probably the adjacencies would be, those people would be into those glucose monitors.

• 23:10Speaker 01

  Yeah.

• 23:10Speaker 00

  They would be into GLPs, which means if they were into those things, they would be into like a Brian Johnson.

• 23:16Speaker 01

  They might not be into drinking your probiotics. I think there's some people that.

• 23:19Speaker 00

  There's probably some people, yeah, Brian Johnson might want a suppository or something. I don't know.

• 23:23Speaker 01

  Right.

• 23:24Speaker 00

  He's into kind of weird stuff.

• 23:26Speaker 01

  Or like implanting poop inside you from someone else. Like that's a hot, that's a weird one.

• 23:30Speaker 00

  That's why I'm bringing it up.

• 23:31Speaker 01

  That would be good to show the press, like this guy is showing how he inserted someone else's feces and it made him healthier.

• 23:37Speaker 00

  Took a turn.

• 23:38Speaker 01

  No, that's Brian Johnson.

• 23:39Speaker 00

  But that's what we're trying to do is try to bait the press.

• 23:42Speaker 01

  Yeah, yeah, yeah. So you want to show them that that's sort of like a weirdness in your group or whatever.

• 23:47Speaker 00

  Well, actually, you bring that up because did anybody see these peptide parties? Silicon Valley story trend? Every, who saw that story trend on social? Yeah, it looks like a third of the audience, a quarter of the audience. That was like an example. They did a peptide party.

• 24:00Speaker 01

  Right.

• 24:01Speaker 00

  And they're like, yeah, people are shooting each other up. And you're like, with heroin? They're like, no peptides, it's even worse.

• 24:08Speaker 01

  Right.

• 24:09Speaker 00

  Your ACL is never going to feel better. Your torn ACL will feel great. All right, let's give it up for Megan. Well done.

• 24:22Speaker 00

  No Jason Calacanis today. He's traveling the world, doing many impressive events, but you do have me, Lon Harris. I'm here in the studio and calling in from the East Coast, our old friend. He's back again, Alex Wilhelm. Thanks so much for being here, Alex.

• 24:37Speaker 03

  Oh, it was such a treat. I love being Diet Coke Jason Standen. It's my favorite job to play.

• 24:42Speaker 00

  You're full sugar Coke Jason Standen. How dare you.

• 24:45Speaker 03

  Oh, you're very sweet, Lon.

• 24:46Speaker 00

  Before we get any further into the show, we're going to be looking back at some very classic, beloved, iconic twist clips from, both from the year 2017, funny enough. And then we, Alex and I like to revisit these classic moments and then see what new conclusions, new ideas we could draw from these fascinating deep dives with some of our favorite founders of years past, obviously full of tactical and practical advice you can apply even today if you are running a company. But before we get into all that, I do want to call attention to this device that you can see hanging here on my lapel, on, on the side of my jacket. That, of course, is a Plod note pin. If you just tap it, a little light comes on and it starts recording everything that's

• 25:30Speaker 00

  going on around you, everyone speaking. Amazing for transcribing your meetings or discussions you're having with team members in the moment, the, anything that you don't want to forget, you just recorded the Plod. It goes onto the Plod app, it goes onto the web. It's, they've got summaries, they've got transcripts, they could turn it into whatever you want. Meeting notes, a lesson plan, if you're a teacher, whatever you want. It's a very impressive product. Alex, you played around with, you got a Plod pin.

• 25:57Speaker 03

  Oh, I've used Plod quite a bit. I mean, what I use it for is actually recording arguments with my spouse. So then later on, I can feed it into a LLM judge and then decide who was more or less in the wrong. It's really great for your marriage, too. Hundred percent.

• 26:09Speaker 00

  Getting a lot of insight into Alex's 2028 divorce proceedings. I don't do that. That was a joke. Don't do that. But if you do want to get good, positive, healthy relationship uses out of your Plod pin, go to plaud.ai/twist, use the code TWIST, and they're going to give you 10% off your Plod note pin. Thanks so much. We applaud Plod, as Jason likes to say.

• 26:33Speaker 03

  Yes, we do. Now, we're going to look at some interviews, Lon, that I think are very important to put into context because we often talk to leading CEOs in the moment, when they have just done the latest thing, and we don't have context about what happened afterwards. So I love to rewind the clock about a decade to some truly iconic companies to see what they were talking about in the past, what were we curious about? And then how does their progress line up with where we are now? So who's first?

• 27:00Speaker 00

  So first, we're going to take a look at this classic moment from Jason and Patrick Collison of Stripe. This was originally published on April 11th, 2017. It was filmed at the Launch Festival 2017. This was Twist, episode 723, for those of you keeping track by number.

• 27:18Speaker 03

  And we're going to kick off with a clip in which they talk about the metrics that Stripe was seeing at the time. And then we're going to have a fun little comparison to where the company is today. Roll the tape.

• 27:28Jason Calacanis?

  You've got a brand new product.

• 27:30Speaker 03

  That's right.

• 27:30Jason Calacanis?

  And we're going to show a video, but I wanted to start just maybe giving people a little context and the history of the company. What's the footprint of Stripe today?

• 27:39Speaker 04

  So we're, we don't disclose many metrics about the business, but we say we handle now billions of dollars of sort of aggregate revenue every year for sort of all the companies building on the platform. And, you know, we've many thousands of companies building on top of it, but we don't disclose the, the exact figures. One thing that's now the case because of Atlas, as Prady just mentioned, and I think is, is super cool, is we, we now work with companies in about 124 countries. And so basically, we now work with companies in just most countries.

• 28:11Jason Calacanis?

  How many people work at the firm, generally speaking?

• 28:13Speaker 04

  We're about to hit 700.

• 28:15Jason Calacanis?

  700?

• 28:16Speaker 04

  That's right.

• 28:16Speaker 03

  All right, so Lon, here we saw Patrick talk about, 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 $1.9 trillion, 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.

• 28:58Speaker 03

  They announced 5 million 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, entrepreneurs doing great things, really good company, scaling hundreds of employees, really proud of the numbers, and it was just an absolute pipsqueak compared to where it is now today. Very impressive.

• 29:18Speaker 00

  I mean, it's also interesting how disclosure and transparency shifts over time. When Stripe was still up and comer, startup, you know, underdog, they were like, we don't, we don't really like to give out metrics. Like, we don't, we gotta, we gotta protect what we're doing and we don't want to pry eyes. And, you know, obviously today, they're publicly reporting, they've got valuations, and we know a lot more about what's going on inside Stripe. But also, the colossals themselves are routinely on podcasts, they've got, I think, the Cheeky Pint, they've got their own. There's, there's a lot more discussion publicly about what's happening at Stripe, the larger that they've grown over the years.

• 29:57Speaker 03

  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 scale of the company.

• 30:09Speaker 00

  You mean reality TV? That's like finding out that the Pawn Stars Pawn Shop is not a real pawn shop. Like, you're

• 30:15Speaker 03

  It's like learning that the Real Housewives of Rhode Island are not really indicative of the average housemaker in the state. Talking to you enough.

• 30:22Speaker 00

  I don't think anybody thought that. I think you might have been the only one who thought that. All right. So I think we should move on to our next clip. Jason tried desperately to get Patrick to bag on PayPal, one of Stripe's 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.

• 30:54Jason Calacanis?

  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 going to 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 G2I can help. G2I 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

• 31:35Jason Calacanis?

  using AI. My mom's using it. My brother's using it. My kids are using it. No. G2I 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 G2I 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,

• 32:20Jason Calacanis?

  it didn't work. Every time we tried to accept money from people, it didn't work. And then they would, everybody would tell me the same thing. I have PayPal, I have one. Oh, can I, 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 where you ran? It's the whole, he just raised it. There 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.

• 32:43Speaker 04

  Right.

• 32:44Jason Calacanis?

  Was that what led you to have that opportunity to zip in there?

• 32:47Speaker 04

  Well, look, don't want to speak ill of any particular company, but yeah, 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 so optimal. But, but, you know, it's easy to kind of focus on PayPal. And I think that's actually, you know, obviously they're, they're pretty large and established and so on. But it certainly was not just them. And that's sort of when we look to our friends, people we knew running companies and so on, and most of them 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're working with gateways, processors, sort of stuff like this, right? And they were sort of looking to, you know, to buy

• 33:29Speaker 04

  sort of 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, you know, 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 enable people to really iterate.

• 33:53Speaker 03

  I absolutely love that clip because there's a bit of a historical echo here, Lon. 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 was probably worth about what it is now, $48, $50 billion. It's gone up, it's gone down, it's back to where it was. And in the meantime, Stripe has just been churning along.

• 34:24Speaker 00

  Yeah. Of course, as, as, as we sort of teased, Stripe and Advent International made a joint offer to acquire PayPal for about $60.50 a share. That would have valued it at about $53 billion, a little bit more. But, you know, it did not, that, that was from mid-July. We so far don't have an update from PayPal. It looks like maybe that particular deal has sort of stalled out. Just, you know, in retrospect, funny, nine years after these comments, that they sort of came back around to each other. The other thing I think that is so fascinating is, not only has PayPal remained like sort of consistently valued in, in all of that time, a very long time in the technology world, but it's so fundamentally the same offering. I mean, it just, it's like PayPal always stayed PayPal. They didn't,

• 35:09Speaker 00

  all these other fintech revolutions have happened. I've now got, you know, I had the PayPal app on my phone this whole time. Now I've got CalShe next to it. Now I've got Zelle next to it. Now I've got Venmo next to it. Now I've got Robinhood next to it. And it's like, why didn't PayPal become any of those other things? It's sort of a fascinating question.

• 35:30Speaker 03

  I mean, I think you're describing what, like, the entire opportunity for startups. Because what does a startup do? They go into a market where the incumbent is lacking, say, or they invent a new market. In this case, I think what startup did was a bit of both, attacking incumbents and creating something that was new. You saw Patrick in that clip talk about how some companies want to be like the AWS for payments, but they don't have the actual tech for it. So clearly, they were improving the tech, but also doing something that we've seen before, much better. And the market will respond. So if you look at the most recent results, Lon, if you look at PayPal's second quarter results from this year, revenues were up 5% year over year, which is essentially zero after inflation, if you want to do that.

• 36:09Speaker 00

  Might as well be nothing, yeah.

• 36:10Speaker 03

  Might as well be nothing. I think this is just the risk. You know, a large company spends more time defending its cash flows than it does innovating. And sometimes you can see an incumbent that was built as a disruptor originally fall prey to the same foibles that caught up their previous generation's competitors. Another example of this recently, I would say, Amazon blocking Muse and Instinct and other agents for being able to interact with its website because it wants to charge ad dollars against human eyeballs, not facilitate machine transactions. Mistake. Fundamental mistake that will bite them in the backside.

• 36:42Speaker 00

  Yeah, we said that on the show. There was like a, there was a clip going around that we put on social about Jason, I think it was with me talking about this. And people got so, they were like, it obviously makes sense that Amazon would like, why would you guys even expect Amazon to like, play along? Like, they want you to use their own agent. And it's like, it doesn't, it doesn't, the moment you try to do it, and then you can't buy something off of Amazon with your agent, and you get frustrated, that's the moment it becomes a mistake. Like, they should be facilitating any way you want to buy things. They're Amazon, that's what they do. They sell you things in an easy, direct fashion. That's like the whole bit.

• 37:16Speaker 03

  They should have the world's biggest hook outside for my agents to hook on to. They should accept any possible type of payment that I want. They should have an intelligent way to handle my permissions. And you know what company would support that? Stripe.

• 37:28Speaker 00

  Stripe.

• 37:28Speaker 03

  Who was working on a gigantic payment.

• 37:30Speaker 00

  Exactly.

• 37:31Speaker 03

  So it's, it's fun to see people that were right, stay right. And I'm really glad that they didn't buy PayPal. Because I think that deal looked really dumb from the outside. I'm sure there was more logic to it. But I'd rather have Stripe unencumbered than Stripe dragging PayPal behind it like the alien in Independence Day.

• 37:49Speaker 00

  Okay, there you go. Took a second, but I got there. Let's move on to our next clip. This is, we promised up top, I don't like to promise things at the top of YouTube videos that we're not going to deliver, folks. So we're about to deliver. This is, I think, a really good piece of tactical and practical advice for founders, coming from arguably one of the great founders of the modern technology era. Hard to make that argument. Let's take a look, Zach, at this next clip about how good ideas don't always seem intuitively great when you first have them.

• 38:21Speaker 04

  Over the course of that summer, basically, and again, I think there's kind of maybe a lesson here where, you know, I think a lot of really good ideas really don't seem particularly great or big upfront. Again, certainly, speaking from personal experience, Stripe did not. But over the course of working on it that summer and sort of thinking about it and so on, we kind of came to shift from sort of thinking about it merely as this nice little tool for developers that kind of makes their lives easier initially, which is kind of what we started out with, to kind of realizing that, well, when you sort of survey the broader landscape, it's not just that it sort of sucks for developers to have to sort of integrate payments initially into their website or service or whatever, but that like the whole edifice is broken, right?

• 39:02Speaker 04

  I mean, 2% at the time, 2% of all consumer spending took place on the internet. And it's like, why is it so low? Why is it so insanely difficult for any company to do anything that touches online transactions? When we went, we talked to a midsize company or a large company. It's like, you know, what's your experience of just like dealing with business and the internet? And they would, you know, they would spend half an hour telling us about sort of the markets they couldn't serve and their fraud challenges and the things they couldn't integrate. And just, you know, we came to appreciate that sort of what we thought was kind of a, you know, this little pond was actually kind of this much larger ocean. And so we see that summer, we kind of made two decisions to drop out of school, or, you know, as our mom can use to prefer, we call it to take, you know, a leave of absence.

• 39:43Speaker 04

  And then, and then secondly, we had to go, you know, raise some initial money from Sam Altman and Peter Thiel and Sequoia and a couple of others.

• 39:51Speaker 00

  Yeah, so I mean, this is, I'm writing these daily Substack tactical and practical posts. You can check them out, twi startups.substack.com if you're curious. And this, variations on this topic have come up so frequently throughout, not just this week in startups history, but any other tech founder startup podcasts that you watch. The idea that a lot of people think that when you come up with an idea for a business, the very first thing you do is make a product. Like, I've figured out a product that people need and I'm going to build it. And today, this is so especially true because you can literally just tell your agent or Claude, like, here's the tool I have an idea for, let's build it together.

• 40:35Speaker 00

  And, and what this and so many other founders come back to is really when you come up with a, with a business idea, you've figured out there's a problem. Like, here is a problem people have, it needs solving. I want to be the person that can facilitate the solution to this. But without getting your hands dirty, building things, talking to your future customers, learning everything you can, you probably don't know the exact right solution. It's probably going to take iterations and education and research to really crack, how do you solve the problem in the way that the people who are going to use your solution are going to come back to and repeat use over and over again. So like, I think that's kind of what a lot of this gets to is that you're, you're not ready

• 41:20Speaker 00

  to build your finish, like, let's build Stripe today because I figured out there's a need for Stripe. It's like, okay, now you've got to do a lot of what Patrick talks about in this clip. Now you've got to like, talk to all of the people who run banks and financial institutions who understand what's missing now. And then, in the future, you will know what you need to build that actually solves the real contextual problems that exist.

• 41:45Speaker 03

  Yeah, whenever I hear a story like this from a founder, I'm always, one, impressed at their ability to just work on things that are non-obvious, non-consensus and difficult. Because that's kind of like, you're out in the field by yourself digging a hole. Like, it's not exactly a fun place to be.

• 42:00Speaker 00

  Yeah.

• 42:01Speaker 03

  But also, the willingness to have patience. I mean, if you think about the current startup world today, Lon, every time you see one of those revenue charts, everyone's trying to be the fastest to 100 million or the fastest to a billion in recurring revenue, whatever, whatever. Everyone's obsessed with what have you done the last 30 days? And how can I measure it? And how can I instrument it? And how can I put that against other things to benchmark it? This seems like a slower process, a bigger problem. Yes, it did take a while, but think about the result they got out of this. I mean, this is a 100-ish billion dollar company now, but they had to go out there and ask questions. I just, I hope that there's still room for founders like the Colisons, who do things that take time to get launched, get rolling and become unstoppable, to build up that inertia versus the companies today that are just kind of going from zero to hero overnight.

• 42:47Speaker 03

  And I worry that they're going to go back from hero to zero in the same timeframe in some cases.

• 42:50Speaker 00

  Yeah, I feel like it's, it's probably like a pendulum swing. Like, right now, things are just in this incredibly like, we figured out what a few of the key AI bottlenecks are and everybody is just pouring into those niches. Like, okay, we need like faster, more efficient inference. Like, everybody try to do that, we know that's a problem. You know, so I think we'll probably wait a little while and then we'll get back to like, we have to do a little bit more legwork to figure out exactly what these bottlenecks and obstacles are to the next iteration of our AI agents. Because I'm assuming it's all going to be AI from now on.

• 43:25Speaker 03

  I do just want to add a caveat though. I'm not trying to say that today's companies that are growing quickly are not valuable, aren't doing something cool.

• 43:31Speaker 00

  Right, of course.

• 43:31Speaker 03

  I just appreciate that there was a time when you could do the equivalent of messing about in the garage longer. And I think that's something that, that we don't want to lose in the broader startup conversation.

• 43:42Speaker 00

  I'm reminded of Clu, Q L O O, who's been on this week in AI a few times recently, Alex Elias, a great founder. They predated AI, they were already trying to figure out recommendation engines and algorithms. And then AI came along and it's like, oh, this technology is even better. Like, let's just adopt that. And like, that's been a fascinating process to sort of follow is like, becoming this AI company. Because obviously, AI is good at recommendation engines and put in a lot of data about what you like and it spits out, here's what else you'll like. And, you know, it just reinvented that business, but he's been building that business all along.

• 44:20Speaker 03

  Yeah, no, I love it. Now, my last clip from this interview comes when we're talking about the darkest moment in Stripe's history. And the story is not going to go the way you think it is. So listen closely to what Patrick has to say here.

• 44:35Jason Calacanis?

  Here's a common founder scenario. You're looking over your sales numbers at the end of the quarter. And hey, your team, they're at risk of meeting their quota. This kind of thing happens all the time. You can't figure out what the specific problem is without taking a closer look at all of the data. Not long ago, that meant pulling it all in from across the entire organization, a time-consuming ordeal. But now today, there's Rippling AI. Rippling is already built on your real-time people and business data. That means Rippling AI pulls metrics from both their data and your CRM into one dashboard. And then you get to see how close you are to hitting quota. And you can figure out the root of the problem of why you're not getting there. Maybe it's the marketing, maybe it's the targets they're going after.

• 45:18Jason Calacanis?

  You can break down all of that, revenue by region, by customer size. All of that important information is going to be at your fingertips in seconds with Rippling AI. When you're running a company, you have important questions that need immediate answers. That means ASAP, as in right now, as in yesterday. So if you're ready to rule your business, head to rippling.ai/twist to get the only AI built to give you full visibility and take complex actions across your startup. What was the darkest moment? The moment where you're like, this is not going to work.

• 45:51Speaker 04

  Yeah, so there was a moment very early on. And so, you know, now sort of Stripe is replicated across, you know, multiple data centers and invested kind of a huge amount in redundancy and availability and failover capacity and everything else, right? That was not the case, you know, four months in, call it. Maybe it was a little bit more, maybe it was six months in. And, and six months in, you know, we still ourselves, of course, you know, took it very seriously. And the fact that sort of our customers relying upon us for, for their revenue was, you know, was a big deal for us, right? And so my pager went off at 4:00 AM one night. And, you know, the API was down. And, and again, this is not like a, a social media app or something, right? This is the conduit for our customers' revenue.

• 46:36Speaker 04

  So it was a big deal. And so I remember kind of immediately heading to the office. We lived, you know, very close to the office. I was at the office within five minutes, you know, 4:00 or 5:00 AM, and started to kind of try to figure out, diagnose what was going wrong. And it turned out that sort of an upstream switch at our data center had failed. And, and you know, nominally, they had redundancy and multiple internet connections, but it had been misconfigured and so it was all down. And so we had multiple servers, but like the, the underlying uplink connection was broken. And then so, you know, upshot being API was down and we couldn't do anything about it.

• 47:08Speaker 04

  And it was amazingly painful, right? Because, you know, the thing is down. You sort of want to be kind of furiously typing, you know, fixing, getting it back up, whatever. And you just couldn't, had to, you know, wait on hold. And we were getting these kind of forlorn updates from the data center every 15 minutes. That's kind of their progress in fixing it. Eventually, and you know, this felt like one of the longest, you know, eight hour periods of my life. It was almost literally eight hours. They sort of got a new switch and they replaced it and the whole thing came back up. But that's not why it was the darkest moment. The darkest moment, of course, was because I was bracing myself for the deluge in complaints and dissatisfied customers and anger and vitriol and everything else. And, you know, 1pm rolled around and as far as I could tell, nobody had cared or noticed.

• 47:52Jason Calacanis?

  Wow, dodged a bullet.

• 47:55Speaker 04

  Anyway, come on, some of that was good news, but you know, as I reflected on it, I realized it was actually kind of existentially bad news.

• 48:02Speaker 03

  Oh my gosh, what a brutal story. So a couple of learnings from that. One, early on, super hands-on founders, very close to the office, they were not on a jet, they were not at a conference, they were building. I think there's a little, a lot of side quests founders can do these days. At that time, far fewer. But the, the lack of being yelled at as a very dark moment, I thought was a really good encapsulation of the founder journey because either way, he was going to feel bad, either he was going to get yelled at and feel bad, but it turns out there's something that's even worse, Lon, which is being ignored because no one cared.

• 48:33Speaker 00

  Yeah, I mean, I think that's, that's like the, you know, the crux of the story is like, we all, we all imagine, we're all walking around all day, like thinking about how embarrassing the stuff we've said or did are, like what a bad job we're doing. Like, we're all very hard on ourselves all day. You're imagining other people are judging you or criticizing you or like watching you and being like, oh, this idiot. And really, Jason and I have talked about this many times, nobody else is thinking about you in the world. Like, if, if, right now, if you went and like, looked up every single person who you've ever met and their thoughts, like such a tiny fraction of that thought would be about you and anything you've done, good or bad.

• 49:16Speaker 00

  And it could be, it could be freeing in some ways, but when you're starting a company, it could be a real struggle because you're like desperate for attention and eyeballs and it's so hard to get people's attention and eyeballs. I mean, especially like if you are in a crowded marketplace or you're trying to get the attention of, you know, like anybody who's like busy, and this was 2017, it's exponentially harder in 2026. There's so many more distractions today than there ever were. Like, it's, it's real, somebody, anybody who's ever tried to build anything on the internet can tell you, like, the attention economy is rough and it takes no prisoners. So like, you are, you are up against like a million other things for everybody's two seconds of focus.

• 50:00Speaker 03

  So that, dead on, Lon. But also, we mentioned earlier, the ease now with which people can, can make stuff, right? You can prototype faster, launch company faster, which means that your ability to have a lead on the competition has gone down. Anything you do can be replicated to some degree pretty quickly. And then you're not only competing with the world to pay attention to your genre and your idea, but also to compete with other people that are now just following in your footsteps. I've kind of roughly called this, everyone's building the same startup, because it kind of converge a little bit these days. But yeah, I, I cannot imagine how they managed to get up off the mat after they got the service back up and no one noticed, but I'm really glad that they did because that early face plant, I think we can call it, didn't stop what is now this $100 billion behemoth that runs a big chunk of the world.

• 50:44Speaker 03

  Also, did you catch the number, he said, the 2% number? That only 2% of transactions were online total?

• 50:49Speaker 00

  I did catch that.

• 50:51Speaker 03

  Pair that now with 2% of global GDP passes through Stripe alone.

• 50:55Speaker 00

  Wow, so they became the 2% that they originally detected, yeah.

• 51:00Speaker 03

  That's why I wanted to get to that number, because I wanted to bring it back here, because I think it's such a good indication of just how much the growth the company has seen in the, in recent years.

• 51:07Speaker 00

  Yeah, it's, it's an old adage. I mean, we hear it from the VCs on our roundtables all the time. It's like the, the founders who win, they're not necessarily like the smartest, or they had the best idea, or they had the best advisors. It was, you know, they, they, they were the most persistent. Like, they hung in there the longest, they didn't give up. Everybody else pivoted to four different ideas and they just stuck to their guns and stuck to their vision and, you know, held, held to what they really believed in and persevered. And I think that's like the huge takeaway here is like, yeah, I'm sure there was a moment there after that day where the Stripe guys were like, people don't want Stripe, you know, like we, we went down a whole day, nobody noticed, nobody cared, like they're

• 51:49Speaker 00

  not using our service, we should make something else, you know, like what about a chat GPT wrapper? It was, it was too early for that, but you know what I mean?

• 51:57Speaker 03

  I bet it wasn't a single cheeky pint that got them through that. I bet it was a number of pints.

• 52:03Speaker 00

  Yeah, cheeky's pint is how you do, is how you pluralize.

• 52:07Speaker 03

  No, it's not AirPods Pro, stop it.

• 52:09Speaker 00

  It's not. All right, we got one more, we've got one more Stripe clip and then I promise we will move along. This one, I gotta say, I feel like it's less like practically useful in the moment and it's more just funny because of the nine years that has progressed since this was shot and now retrospective, looking back on it. But here is Patrick talking to Jason about why in 2017, despite lots of pressure, Stripe did not want to go public. And we're actually planning, don't know if you've heard about this, they're planning on putting off going public as long as possible. Here's Patrick.

• 52:44Jason Calacanis?

  Just generally.

• 52:46Speaker 04

  We, we're going to hold off for as long as possible from partaking in them in that, so genuinely, the, you know, from our standpoint, instead of Atlas, I think is a good example of this, you know, there, as we think about the idea of growing the GDP of the internet, I mean, there are, there are so many things that, you know, we want to invest in on that front, they're just going to take a long time to come to fruition. And, you know, of course, you know, there are good examples, there are some good examples of companies that, that I think have done a good job of sort of maintaining really long-term time horizons while being in the public markets, you know, Amazon being the kind of most famous and prominent example. On the other hand, if you, if you look at the kind of Amazon's early history, you know, they had an incredibly turbulent time for sort of their, their first couple of years as a public company.

• 53:29Speaker 04

  Instead of now, 2017, you know, Amazon is up whatever, 50% year over year. Exactly, it, it all looks great, but sort of, they really had a tough time in the beginning. And so I, I, I think there's, and you know, this is a broader kind of structural challenge across the industry, but I, I, I think being a public company certainly does not stop you from taking a really long-term time horizon, but it does make it more difficult.

• 53:48Jason Calacanis?

  And so much more difficult. And you have all your employees looking at a stock price every day, which Bill Gurley said there, when he was an analyst, he was, wrote a paper to try to get the employees to stop, Amazon's employees specifically, to stop looking at the stock price and focus on work.

• 54:02Speaker 04

  And I'm sure that worked, you know, just as well as you might think, but, but, you know, from our standpoint, you know, we, I think being a public company kind of makes sense when you've reached sort of, you know, some, some kind of, some point of, some point of stability, some plateau of, you know, you, you've done the stuff that you at least initially set out to. And we feel like we haven't, we're, we're still very early in sort of this trajectory that we first established. And just because we work with startups and technology companies, you know, they themselves have lengthy trajectories. And so, you know, this is just going to have to be, when you're building infrastructure, you know, there's just long time horizons involved.

• 54:38Speaker 00

  Boo.

• 54:39Jason Calacanis?

  Yeah.

• 54:40Speaker 00

  Boo. Yeah, you're, you're number one IPO fan who follows them like sports, so I understand that must be frustrating, but I think it's a really fascinating answer to look back on now, like, so does that mean that even a decade or so after this, they still feel like our work here is not yet done? Like, what is left that Stripe needs to conquer before they feel ready to go public?

• 55:03Speaker 03

  Well, they held off when they were being pressured and now they're too big to pressure. What are you gonna do? You're gonna go tell the Collison brothers to do something? They're gonna tell you to take a hike. Light wings, they're like, I mean, they're worth, what, 10, 15 billion apiece? They run this huge company. I presume they have some form of voting control or protections thereof and they don't want to go public, so tough. Now, they are intelligent about this, there are tender offers, there are things that they do to provide some liquidity, but I want to actually push back because I feel like he reached for a relatively uninspiring example there. Patrick's not here to defend himself, so I'm not going to take this too far. But I will say that like saying that Amazon had a little bit of a struggling time early

• 55:46Speaker 03

  on its public life and therefore Stripe shouldn't go public is forgetting when Amazon went public and what happened next, which was the dot com crash. So I'm sure it was probably tough for a lot of public companies. I don't think Amazon's struggles were because of that. And also, other public companies that have grown to their size while being public, Microsoft, Apple, Alphabet. I mean, so to me, if you look at the big companies out there, Nvidia, they all did 95% of their growth while public and it worked great. So maybe something has changed, Patrick, and I think what has changed is your ability as a founder to say no to going public, but I, I have always found it to be a specious complaint.

• 56:25Speaker 00

  We love a spicy take. I'm going to send this to him and hopefully he'll respond and then this episode goes viral.

• 56:30Speaker 03

  Don't, don't get me in trouble on X. I don't want to have all of his fans attacking me like, what if you've never built a company more than?

• 56:35Speaker 00

  I wouldn't do it that way. We have very nice fans. Everybody out there, don't attack Alex or Patrick Collison on X.

• 56:40Speaker 03

  Yes, send all your hate mail to [email protected].

• 56:43Speaker 00

  Thank you, yeah, put that out there. All right, I think, I think we're good. I think we're good on Stripe.