This Week in Startups
00:44:20 · Alex Wilhelm, Jason Calacanis
[00:44:20] S3: 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 gonna go the way you think it is. So listen closely to what Patrick has to say here. [00:44:35] S2: 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. You can break down all of that revenue by region, by customer size. All of that important information is gonna 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?
00:44:35 · Jason Calacanis, Patrick Collison
[00:44:35] S2: 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. You can break down all of that revenue by region, by customer size. All of that important information is gonna 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? [00:45:48] S4: The moment where you're like, [00:45:50] S2: this is
00:45:50 · Patrick Collison
[00:45:50] S4: Yeah, not going to so there was a moment very early on, you know, now, sort of Stripe is replicated across 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. Six And months in, we still ourselves, of course, took it very seriously, and the fact that our customers were relying upon us for the revenue was a big deal for us, right? And so my pager went off at 4AM one night, and the API was down. And again, this is not like a social media app or something, right? This is the conduit for our customers' revenue, so it was a big deal. And so I remember kind of immediately heading to the office, we lived very close to the office, I was at the office within five minutes, know, four or 5AM, 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, nominally they had redundancy and multiple Internet connections, had been misconfigured, and so it was all down. And so we had multiple servers, but the underlying uplink connection was broken, and so upshot being API was down, and we couldn't do anything about it. And it was amazingly painful, right? Because the thing is down, you sort of want to be furiously typing, fixing, getting it back up, whatever, and you just couldn't have to wait on hold, we're getting these kind of forlorn updates in the data center every fifteen minutes. That's kind of their progress in fixing it. Eventually, and you know, this felt like one of the longest eight hour periods of my life. It was almost literally eight hours. They sort of got a new switch and they replaced it, 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.
00:47:52 · Jason Calacanis, Patrick Collison, Alex Wilhelm
[00:47:52] S2: Wow. Dodged a butt. [00:47:55] S4: Anyway, Kevan, some of that was good news, but, you know, as I reflected on it, I realized that it was actually kind of existentially bad news. [00:48:02] S3: Oh my gosh. What a 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 quest founders can do these days. At that time, far fewer. But the the lack of of being yelled at as a very dark moment, thought, was a really good encapsulation of the founder journey because either way, he was gonna feel bad. Either he was gonna get yelled at and feel bad, but it turns out there's something that's even worse, Lawn, which is being ignored because no one cared.
00:48:34 · Lon Harris
[00:48:34] S0: 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 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 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. And it it 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, 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 who's ever tried to build anything on the internet can tell you like the attention economy is rough and it takes no prisoners. And like you are you are up against, like, a a million other things for everybody's two seconds of, focus.
00:50:00 · Alex Wilhelm, Lon Harris
[00:50:00] S3: So that dead on lawn. 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 make it into 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 they tend to 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 Yeah. Didn't stop what is now this $100,000,000,000 behemoth that runs a big chunk of the world. Also, did you catch the number you said, the 2% number that only 2% of transactions were online total? [00:50:50] S0: I did catch [00:50:50] S3: that. Pair that now with 2% of global GDP passes through Stripe alone. [00:50:56] S0: Wow. So they became the 2% that they originally detected. Yeah. [00:51:00] S3: That's why I I wanted to get to that number because I wanted to to bring it back here because I think it's such a good indication of just how much growth the company is seeing in the, in