The Exchanges

Q The rapid revenue growth. Was there a time when you were like, oh, shit, we're growing fast again, and we're locked into this acquisition?

A I don't think that there was that specific question on my mind. Um, the question that was always on my mind was, are we undershooting the long-term opportunity by being part of another company? And for every founder that's ever thought about selling their company, like, that's the key question that, that they're probably asking themselves. I don't think that most people, like, immediately orient on value, the dollar value of the acquisition. Like, sure, yeah, it reaches a threshold and, and the dollar value, like, starts to make sense. But I think when people really go through that Agony around, um, uh, selling a company. It's much more about, like, am I creating the long-term impact? Am I fulfilling the mission? Am I, am I achieving the vision that I've set out? And for me, it was always about that. You know, making the decision to sell the company to Visa, um, that was, you know, one of, if not actually the hardest decision that I've ever made, um, uh, uh, certainly, certainly in the Pride context.

AI assessment note: “I don't think that there was that specific question on my mind.”

Q Do you remember the moment you made it?

A Oh my gosh, yeah, yeah. It was, um, my leadership team and I, it was, uh, right, Um, ah, we were doing this off-site because we didn't want to be in the office. Um, ah, and we were sitting in my living room. I'd had them all there. We were, like, had this offer, and, and we were going through, like, the pros and cons of it. And, um, you know, we went around. We talked about what people were thinking, and then I kicked them all out, and I was like, look, I need to think. Like, I'm making this call, like, at the end of the day. Like, I've gotten all of your input, and I just need to think. And it was, like, me sitting in my living room. Um, ah, you know, my wife is out of town. I'm just kind of alone sitting there. Um, and ended up making what I think was a 51 49 call to say, like, it's the right answer to sell the business. Um, For a variety of reasons at the time. A year later, we had that same meeting, same group of people sitting in my living room, having the same, same style of conversation. And that was a, like, you know, ninety-nine-one decision. I was, like, pretty certain that the right answer was to walk away. I just wanted to make sure that everyone else was aligned. And what had changed in that innovating period is that our business had grown quite massively. We'd reached this escape velocity, um, and the concept of digital finance had really taken hold of something t…

AI assessment note: “We'd reached this escape velocity, um, and the concept of digital finance had really taken hold”

Q And then you do, like, milestone-based financing, which is, like, hey, if we find sufficient product market fit, We'll open up new resources. How do you think about the next stage post-atomic team?

A Yeah, if you, if you try to over-processize that, then it doesn't really work. Like, a lot of people try to run, like, an internal VC style model, which is like, you know, we'll fund you for a million bucks for a year and we'll figure it out. Yeah, and you can do that, but it becomes over-processized, and then everyone starts to, like, try to hack the process as opposed to, like, really finding the, the unique insight. Um, I'd rather just, like, let people go run at a thing for a while, and, like, usually they will come, like, at least I've found, they will come back and say, hey, this is not gonna work. Or, like, hey, there's something very real here. They might come back in a week and say, like, there's something very real here, and, like, I, I have a customer that's, like, chomping at them to buy it. Like, I really need to fund it now. I don't want them to wait 18 months to come back and ask for more resourcing. Um, on the flip side, uh, you know, no one inside the company wants to go, like, off in a foray for, like, three years finding nothing.

AI assessment note: “if you try to over-processize that, then it doesn't really work”

Q But are they, if they're coming from 10 years with knowledge of the banking sector, they, do you see what I mean?

A Fine, maybe. Um, but I guess what I think is in general, you know, if you have two atomic teams, you throw them at the same problem, if they have like roughly the same skills, they're gonna start from roughly the same place. And one might move faster because they have this knowledge or background or whatever it is. Um, and when that, that has been like one of the things that I've evolved my thinking on quite a lot over the years is like the importance of experience. I think a lot of people worry too much about defensibility In the immediate term and like at the start of a new project, um, and they were far too little about defensibility in the late stages. Um, so as long as, you know, the, the grinder problem, the, the, the difficult, hard hustle problem that you're going after, um, has the ability to be meaningfully differentiated in the long term via network effects or brand or scale or whatever it is, um, then it's great. But, um, if it never has the ability to be differentiated, I mean, you know, be careful with your time.

AI assessment note: “evolved my thinking on quite a lot over the years is like the importance of experience”

Q But are they, if they're coming from 10 years with knowledge of the banking sector, they, do you see what I mean?

A Fine, maybe. Um, but I guess what I think is in general, you know, if you have two atomic teams, you throw them at the same problem, if they have like roughly the same skills, they're gonna start from roughly the same place. And one might move faster because they have this knowledge or background or whatever it is. Um, and when that, that has been like one of the things that I've evolved my thinking on quite a lot over the years is like the importance of experience. I think a lot of people worry too much about defensibility In the immediate term and like at the start of a new project, um, and they were far too little about defensibility in the late stages. Um, so as long as, you know, the, the grinder problem, the, the, the difficult, hard hustle problem that you're going after, um, has the ability to be meaningfully differentiated in the long term via network effects or brand or scale or whatever it is, um, then it's great. But, um, if it never has the ability to be differentiated, I mean, you know, be careful with your time.

AI assessment note: “one might move faster because they have this knowledge or background”

Q But are they, if they're coming from 10 years with knowledge of the banking sector, they, do you see what I mean?

A Fine, maybe. Um, but I guess what I think is in general, you know, if you have two atomic teams, you throw them at the same problem, if they have like roughly the same skills, they're gonna start from roughly the same place. And one might move faster because they have this knowledge or background or whatever it is. Um, and when that, that has been like one of the things that I've evolved my thinking on quite a lot over the years is like the importance of experience. I think a lot of people worry too much about defensibility In the immediate term and like at the start of a new project, um, and they were far too little about defensibility in the late stages. Um, so as long as, you know, the, the grinder problem, the, the, the difficult, hard hustle problem that you're going after, um, has the ability to be meaningfully differentiated in the long term via network effects or brand or scale or whatever it is, um, then it's great. But, um, if it never has the ability to be differentiated, I mean, you know, be careful with your time.

AI assessment note: “one might move faster because they have this knowledge... but people worry too much”

Q And then the final one, if we talk about what could you do twice as fast, think about the next five years for you. What does that look like? And just how big could plan get?

A Oh, I see no ceiling. There's quite a lot of room for growth, and especially as we think about both the ecosystem that's growing in the U.S., the ecosystem that's growing internationally around fintech, and the fact that fintech is becoming not just something that banks do, but it's something that all companies do. Anyone that has a financial relationship with a consumer continues to be a part of fintech, and we're thinking about how do we make the quality of those financial interactions even better every time. Hopefully no ceiling. I see a great deal of growth ahead for the company. My role continues to get more and more interesting, harder and harder in many different ways. And so I'm, I'm just having a lot of fun, and hopefully I'm having as much fun as I am now in five years.

AI assessment note: “Oh, I see no ceiling. There's quite a lot of room for growth”

Q If I asked you in five years time, where would you be exceptional for Plaid to be, and where would be a fail, what would the answer be?

A If anyone can get credit, uh, great access to credit based on the data that they have, uh, with them in their head, um, uh, like, you know, your, your, your, your, your transaction history, so on and so forth, you have the ability to link that based on the data you have in your head, um, uh, that would be a, a huge unlock. Like, I think if financial fraud, which right now, at least in the US, is like growing at an increasing rate, um, if we can have it either flat or, uh, at least like growing at a decreasing rate minimally, ideally like declining, Um, that would be huge. And so, and I think we can, we can very realistically do that. And I think if it's a, you know, a, a, a, a one tap experience to, to apply for a loan. Like that's, that's the threshold that we have. That's the target that we have is like, I want to apply for a loan. Click apply. Do a face ID. Um, great. Your application's submitted. Like that's the goal.

AI assessment note: “That's the target that we have is like, I want to apply for a loan.”

Q Do you remember the moment you made it?

A Oh my gosh, yeah, yeah. It was, um, my leadership team and I, it was, uh, right, Um, ah, we were doing this off-site because we didn't want to be in the office. Um, ah, and we were sitting in my living room. I'd had them all there. We were, like, had this offer, and, and we were going through, like, the pros and cons of it. And, um, you know, we went around. We talked about what people were thinking, and then I kicked them all out, and I was like, look, I need to think. Like, I'm making this call, like, at the end of the day. Like, I've gotten all of your input, and I just need to think. And it was, like, me sitting in my living room. Um, ah, you know, my wife is out of town. I'm just kind of alone sitting there. Um, and ended up making what I think was a 51 49 call to say, like, it's the right answer to sell the business. Um, For a variety of reasons at the time. A year later, we had that same meeting, same group of people sitting in my living room, having the same, same style of conversation. And that was a, like, you know, ninety-nine-one decision. I was, like, pretty certain that the right answer was to walk away. I just wanted to make sure that everyone else was aligned. And what had changed in that innovating period is that our business had grown quite massively. We'd reached this escape velocity, um, and the concept of digital finance had really taken hold of something t…

AI assessment note: “our business had grown quite massively. We'd reached this escape velocity”

Q How do you think about that, though? Because if you want to raise money every three years, say, for example, you're gonna have to raise a chunky round. You're gonna have to either take a lot of dilution, or you're gonna have to have a really inflated price. How did you think about that?

A We kind of did what felt natural for the company and what felt right for us. Um, my dig is, like, money is a resource. When you need the resource, you should go get the resource. Um, and you should do it, yes, of course, in the most efficient way that you possibly can, but for a certain amount of time, we just didn't need the resource. You know, we weren't spending a ton, or like, like, our business was profitable in the early days. Like, not intentionally, it just happened to be. Um, and so we were like, oh, we don't, we don't need the money resource. Like, money is not the tool that we need to use in order to solve the next challenge. Then later, it became the tool, so we wanted to raise more money.

AI assessment note: “When you need the resource, you should go get the resource.”

Q On the experience side, are there areas where more experience is dangerous?

A Always. I love recruiting. One of my favorite things to do. I started out hating recruiting. Um, and it was one of those things where I realized that if I didn't become good at it, and if I didn't learn to love it, then I was gonna be, you know, I would build a terrible company, because, uh, you, you, you read, uh, any, any business book, we'd go do great, right? First is, do you have the right people on the bus? Second is, what the heck are you building? Uh, but first is, like, get the people right. And I realized if I, if I, if I didn't start to enjoy recruiting, then that would be a challenge for me. So I went deep in, like, I figured out to kind of, like, convince myself, tricked myself in all these different ways to, like, love, love, love recruiting. Um, the key for me was, um, I'm super competitive, uh, I like games, um, and, uh, recruiting is a win-loss game. Can I get this person to want to work at my company? Can I find the best person? Um, and then pretty quickly I will know, yes, they accepted an offer, they didn't accept the offer. So for me now, it's like this intense form of competition with myself on, can I find the, find the person, like I love the hunt, um, and then can I convince them to join me?

AI assessment note: “Always. I love recruiting. One of my favorite things to do.”

Q What has been the biggest hiring mistake that you've made and how have you changed as a result of it?

A Sometimes you get really annoyed with a search that's been going on for a long time, and you're like, I just need to hire someone, and sometimes that's actually true, um, and often that will lead you to make a mistake. But let's imagine, I'm an early stage company, um, I can't find the right accountant, um, but I just need an accountant. At some point, you're actually right, yeah, you actually do just need an accountant, um, uh, but chances are that hire that you're gonna make is not the right one, and you have to, like, dig yourself out of that later, so, like, usually it's been the, like, I really actually just need this job to get done for a little while, Um, and I know I'm gonna have to go back and fix it later, but that's okay.

AI assessment note: “usually it's been the, like, I really actually just need this job to get done”

Q On the experience side, are there areas where more experience is dangerous?

A Always. I love recruiting. One of my favorite things to do. I started out hating recruiting. Um, and it was one of those things where I realized that if I didn't become good at it, and if I didn't learn to love it, then I was gonna be, you know, I would build a terrible company, because, uh, you, you, you read, uh, any, any business book, we'd go do great, right? First is, do you have the right people on the bus? Second is, what the heck are you building? Uh, but first is, like, get the people right. And I realized if I, if I, if I didn't start to enjoy recruiting, then that would be a challenge for me. So I went deep in, like, I figured out to kind of, like, convince myself, tricked myself in all these different ways to, like, love, love, love recruiting. Um, the key for me was, um, I'm super competitive, uh, I like games, um, and, uh, recruiting is a win-loss game. Can I get this person to want to work at my company? Can I find the best person? Um, and then pretty quickly I will know, yes, they accepted an offer, they didn't accept the offer. So for me now, it's like this intense form of competition with myself on, can I find the, find the person, like I love the hunt, um, and then can I convince them to join me?

AI assessment note: “Always. I love recruiting. One of my favorite things to do.”

Q On the experience side, are there areas where more experience is dangerous?

A Always. I love recruiting. One of my favorite things to do. I started out hating recruiting. Um, and it was one of those things where I realized that if I didn't become good at it, and if I didn't learn to love it, then I was gonna be, you know, I would build a terrible company, because, uh, you, you, you read, uh, any, any business book, we'd go do great, right? First is, do you have the right people on the bus? Second is, what the heck are you building? Uh, but first is, like, get the people right. And I realized if I, if I, if I didn't start to enjoy recruiting, then that would be a challenge for me. So I went deep in, like, I figured out to kind of, like, convince myself, tricked myself in all these different ways to, like, love, love, love recruiting. Um, the key for me was, um, I'm super competitive, uh, I like games, um, and, uh, recruiting is a win-loss game. Can I get this person to want to work at my company? Can I find the best person? Um, and then pretty quickly I will know, yes, they accepted an offer, they didn't accept the offer. So for me now, it's like this intense form of competition with myself on, can I find the, find the person, like I love the hunt, um, and then can I convince them to join me?

AI assessment note: “Always. I love recruiting. One of my favorite things to do.”