The Exchanges

Q Listen, I'm thrilled about it, but I want to start, and for those that missed our first episode, man, you know, Brex is this incredible rocket ship that we see today. Where did it all start in terms of the aha moment for you, and how you came to found Brex?

A Yeah, so, Pedro and I were both originally from Brazil, and we started a payments company back in Brazil in 2013 that we sold to a larger payments company. And we moved to the US. We were already in kind of like B to B financial services. And the problem that we saw that we were trying to solve is the fact that startups had to raise a lot of money and couldn't get a corporate credit card. And that was the first problem that we saw was like, how come you have raised five million dollars and you can't get a card to pay for your SAS and AWS bills? And we did a card that did just that. So that was the original insight back in 2017.

AI assessment note: “startups had to raise a lot of money and couldn't get a corporate credit card”

Q Listen, I'm thrilled about it, but I want to start, and for those that missed our first episode, man, you know, Brex is this incredible rocket ship that we see today. Where did it all start in terms of the aha moment for you, and how you came to found Brex?

A Yeah, so, Pedro and I were both originally from Brazil, and we started a payments company back in Brazil in 2013 that we sold to a larger payments company. And we moved to the US. We were already in kind of like B to B financial services. And the problem that we saw that we were trying to solve is the fact that startups had to raise a lot of money and couldn't get a corporate credit card. And that was the first problem that we saw was like, how come you have raised five million dollars and you can't get a card to pay for your SAS and AWS bills? And we did a card that did just that. So that was the original insight back in 2017.

AI assessment note: “the problem that we saw that we were trying to solve is the fact that startups”

Q I can barely read a tweet, let alone a book, and I don't have ADHD, Henrique, so uh, don't worry about that. The second I have to ask is like, when was that moment of realization for you? I had it investing like five years in, which was a long fucking way in. When did you have that moment of realization, and what was it that caused you to change?

A I think there was this new year's, honestly, I know it has to do, I'll double down the reading story, because it was that moment that I think my co-founder and my best friend were discussing about 30 plus books that they read, and that year it was like, oh my god, they're at 30 something, I'm not at one, that's something wrong. And then I started medicating for ADHD, so I started taking Adderall, and then six months in, I read 17 books in six months, I was like, okay, this is working. But then I realized, even though it was giving me some superpowers, I was becoming more focused and productive in some ways, it was taking away from other superpowers that I had. For example, spontaneity and building relationships and other things that I was good at, but every time I was in a meeting and that meeting wasn't ultra productive, I got super upset. It's like, let me go back to being productive, you know, and that's bad with really building relationships with the team and customers and all that. And I stopped medicating and actually things got a lot better. And I think at that moment that I realized after trying to live like someone else with the medication that I was like, oh, okay, actually like what got me here is my strengths and I should like double down on

AI assessment note: “I think there was this new year's, honestly”

Q Man, 1100 people. When you look at that and hear that, do you ever worry that when you're small and nimble, it's, ah, we can outpace them, we can outpace them, and now, do you worry that with size you lose agility? And how do you think agility?

A Yes, and I'll tell you exactly how it happens. And there's a bunch of nuance to this. And this is a good also to talk about what we're building, but, and I'll give us something around expenses because it's what we're building, but this happens across the company. So when you start your company, there's a lot of trust. Everyone is starting out. You trust everyone, you know, everyone, right? Like everyone is doing the right thing. You have time to check and then start scaling and something bad happens. Again, the expenses idea, like someone goes and buys a 5000 dollar bottle of wine. And you get super pissed. You're like, oh my God, this is not the culture of financial discipline that I'm trying to build. This is not a culture of frugality I'm trying to build. This is like outrageous. And you go to your finance team or CFO and says, make sure this never happens again. So then the finance team is like, okay, okay, I need to do something, you know, like the CEO's pissed, like it doesn't need to happen again. And they implement a process. And that process is supposed to make sure that no one can ever buy a 5000 dollar bottom line again. But then, 99% of the people that weren't buying bottles of wine now have to do this process that slows them down in order to solve for the one percent of times that things go wrong, right? Get to this story that I just told and extrapolate to basical…

AI assessment note: “Yes, and I'll tell you exactly how it happens.”

Q I can barely read a tweet, let alone a book, and I don't have ADHD, Henrique, so uh, don't worry about that. The second I have to ask is like, when was that moment of realization for you? I had it investing like five years in, which was a long fucking way in. When did you have that moment of realization, and what was it that caused you to change?

A I think there was this new year's, honestly, I know it has to do, I'll double down the reading story, because it was that moment that I think my co-founder and my best friend were discussing about 30 plus books that they read, and that year it was like, oh my god, they're at 30 something, I'm not at one, that's something wrong. And then I started medicating for ADHD, so I started taking Adderall, and then six months in, I read 17 books in six months, I was like, okay, this is working. But then I realized, even though it was giving me some superpowers, I was becoming more focused and productive in some ways, it was taking away from other superpowers that I had. For example, spontaneity and building relationships and other things that I was good at, but every time I was in a meeting and that meeting wasn't ultra productive, I got super upset. It's like, let me go back to being productive, you know, and that's bad with really building relationships with the team and customers and all that. And I stopped medicating and actually things got a lot better. And I think at that moment that I realized after trying to live like someone else with the medication that I was like, oh, okay, actually like what got me here is my strengths and I should like double down on

AI assessment note: “it was that moment that I think my co-founder and my best friend were discussing”

Q Often it's the VCs, hands up here, who kind of push those great candidates, but also maybe inappropriate candidates on founders. Did you feel An insecurity with your investors, where you ask for permission, maybe because of your age, because of being younger. And I guess, how would you advise founders when it comes to telling, not asking?

A Honestly, we have a lot of problems. That's not one of them. We always manage our investors. It's like, look, you're betting on us to make the right decisions. I want your opinion, and I want your support, but like, this is our company, and we're gonna make what we think is best. Because the reality is, like, if it doesn't work, the accountability's on you anyway. It's not like they're going to take accountability for it. So I think treat your investors with respect, build a relationship with them, get their advice, but make sure that you have the accountability and you have decision making. And we went so many times against what our investors thought we should do. Honestly, some of them at times are right, some are wrong.

AI assessment note: “Honestly, we have a lot of problems. That's not one of them.”

Q Man, 1100 people. When you look at that and hear that, do you ever worry that when you're small and nimble, it's, ah, we can outpace them, we can outpace them, and now, do you worry that with size you lose agility? And how do you think agility?

A Yes, and I'll tell you exactly how it happens. And there's a bunch of nuance to this. And this is a good also to talk about what we're building, but, and I'll give us something around expenses because it's what we're building, but this happens across the company. So when you start your company, there's a lot of trust. Everyone is starting out. You trust everyone, you know, everyone, right? Like everyone is doing the right thing. You have time to check and then start scaling and something bad happens. Again, the expenses idea, like someone goes and buys a 5000 dollar bottle of wine. And you get super pissed. You're like, oh my God, this is not the culture of financial discipline that I'm trying to build. This is not a culture of frugality I'm trying to build. This is like outrageous. And you go to your finance team or CFO and says, make sure this never happens again. So then the finance team is like, okay, okay, I need to do something, you know, like the CEO's pissed, like it doesn't need to happen again. And they implement a process. And that process is supposed to make sure that no one can ever buy a 5000 dollar bottom line again. But then, 99% of the people that weren't buying bottles of wine now have to do this process that slows them down in order to solve for the one percent of times that things go wrong, right? Get to this story that I just told and extrapolate to basical…

AI assessment note: “Yes, and I'll tell you exactly how it happens.”

Q Do you find that having that bluntly realization and awareness really changes your product marketing? Because I love product marketing, but knowing that and then tailoring it does change a lot. How do you think about your product marketing today?

A Yeah, I think that one of the mistakes, if I were to go back, right, and like, think about things we did right to do wrong, First thing we did really right when we started is we had a very simple and clear message. Brex is the corporate card for starters. Absolutely no question what we do and who do we do it for. Then Brex started growing. I think we weren't focusing on too many things. We were doing card. We were doing bank accounts. We were doing bill pay. We were doing expense management. We were trying to serve small businesses. We're trying to serve enterprise. We're trying to focus e-commerce. And then you go to our website and it was super complicated. It's like, what do you do and who are you for? Right? And I think that happened like too quickly. And I think now we're kind of like shifting And I think that's a big thing, you know, around product marketing and just like the product strategy in general, right? Like I think the way we think about the world today is we are going to help your company move faster. I think that's a lot of how we're thinking about our products and how we're going to put into product marketing.

AI assessment note: “I think that's a lot of how we're thinking about our products and how we're going to put into product marketing.”

Q session, because like, and you didn't know this, but like, I'm obviously scaling my teams across media and fun, and I'm many stages behind you, and so I really just wanted to learn from you. So, when we think about leadership, we're both young, I'm sure we both made many mistakes. When it comes to your style of leadership, what are some of the biggest mistakes that you've made, Henrique?

A I think the biggest mistake that I've made is trying to pattern match with people that are too different for me. I think one of the best advice is I got around being a CEO was from, was from Evan Spiegel from Snap. He told me that the most important thing about being a CEO is being authentic to yourself. There's some people that they are like Elon Musk, a type of CEO, right? And can't pattern match. I'm going to try to do everything like Elon Musk does if you're not that kind of personality, that kind of person. And I think for me, I looked at so many other CEOs and I was like, oh my God, I need to do these things. So for example, right, like I was diagnosed with ADHD and I have hard trouble reading, honestly. I don't read a lot of books, but then I was like, oh my God, I feel super bad because I don't read so much, and all these other CEOs, they're reading so many books, they're so intellectual, you know, they seem to be so smart, and I'm here, like, not reading anything. I think, like, trying to be something that I'm not versus just embracing, and the fact is, for me, like, I can't read books, but I learn a lot through people, so I force myself to meet with a lot of interesting people and experts on subjects to be able to learn from them, right, and that's my main mechanism from learning. So as soon as I Admitted my strengths and my weaknesses, and was more authentic around w…

AI assessment note: “the biggest mistake that I've made is trying to pattern match with people”

Q Why did you decide to go to new customers with a new product? Was it just advice? Was it looking for growth in new segments? What was the thinking there?

A I think it was probably overestimating the Our execution ability. We started Brexit with 20 people, and we're like, okay, we have 500 now, so we put 20 for this product, 20 for that product. I mean, that makes sense, right? And that's not how it works. Focus is super important, and I think we probably, we're trying to do too many things at once, so we were like, why not make this one of the bets? One of the five or six or seven things that we're doing. But then there's other than so many competing priorities. It's like, what goes in your homepage of the website? What are your salespeople doing? Where's your management spending time? Because like, you don't have that many Top leaders in a company. Where are they focused on? If you don't make that super clear, your execution just gets, like, slower.

AI assessment note: “I think it was probably overestimating the Our execution ability.”

Q I do have to ask, you've got some incredible people around you. You mentioned some of those names at the beginning. I'm sure you've been given a lot of advice when it comes to scaling the team itself. Is there any key bits of advice that have really stuck with you from some of those mentors, advisors, and investors?

A I think that, you know, one advice that we got that kind of stuck was that someone really good really counts for, like, 10 average people. And I know this sounds, like, kind of obvious, like, a lot of people say this, but I think a lot of people don't apply this in terms of, like, compensation and in terms of, you know, how much effort you're going to do to get them and, like, do whatever it takes to get them. I think that, you know, if you find someone that you think can be like changing for the company, you do whatever it takes to get them on board. And I think a lot of people face that, but they don't do it.

AI assessment note: “one advice that we got that kind of stuck was that someone really good”

Q I do have to ask, you've got some incredible people around you. You mentioned some of those names at the beginning. I'm sure you've been given a lot of advice when it comes to scaling the team itself. Is there any key bits of advice that have really stuck with you from some of those mentors, advisors, and investors?

A I think that, you know, one advice that we got that kind of stuck was that someone really good really counts for, like, 10 average people. And I know this sounds, like, kind of obvious, like, a lot of people say this, but I think a lot of people don't apply this in terms of, like, compensation and in terms of, you know, how much effort you're going to do to get them and, like, do whatever it takes to get them. I think that, you know, if you find someone that you think can be like changing for the company, you do whatever it takes to get them on board. And I think a lot of people face that, but they don't do it.

AI assessment note: “one advice that we got that kind of stuck was that someone really good”

Q with you there and. Some incredible people you've got around the table. The final element on the fundraising was the one hundred and twenty five million dollar basis round. Can I ask, with such an injection of capital, how does one think about Capital efficiency today. You mentioned about kind of not touching the series B when you raise the series C. How do you think about capital efficiency today?

A I think that for a fintech company, just having a big balance sheet is very important, right? So a part of the money raised is just, you know, to sit there for a rainy day. I think that, you know, having that is super important. In terms of capital efficiency, I think that, you know, you should save on some stuff and like not save on others. So for example, I think like you shouldn't save on employee comp. If there's good people and you want to hire them, like, and you have to raise everyone else's salary just to hire this person because, you know, they're more comp and you need to be fair to everybody, like, do it. Don't save on that. But try to hire maybe less people, um, and do, you know, have your people work more and don't spend on, you know, a lot of, like, stupid stuff, like sculptures in the office and, you know, expensive furniture and stuff like that, right? Like, Be frugal with things that don't matter, but people is the thing that matters the most, so I say invest in that.

AI assessment note: “In terms of capital efficiency, I think that, you know, you should save on some”

Q kind of hiring. One incredible hire that you made recently in the last couple of months was obviously with the new CPO. Tell me, obviously you came from incredible tenure at Facebook. The question I have is, like, what does it take to attract world-class talent like this, and why did you decide now was the right time to bring in that tenured, incredible-logoed exec, and now being that time?

A Well, I think there's a couple reasons we hired Karandeep, right? The first one, we wanted someone that had both B to B and consumer experience, which I think was very important for us, because with what we're building now, and I'll chat about it a little bit later, but It's incredibly focused on both the end user, the employee and employees and managers, but also the controllers and the admins and the finance team, right? Like there's this two pieces of the product. So we wanted someone who like had experience and kind of like doing both. So that's what I think one of the main reasons we hired him. And two, I think like he works super well with us. He was an engineer by background that also ran product, but he also, I think biggest plus a lot of smart product engineering people is that he was actually a GM. So he had like sales and marketing and like P and L accountability. That was like a huge deal for us because it wasn't like he was just doing his product there and hoping that people signed up. He had like real sales accountability, which makes him very good at the trade-offs between product engineering and customers, you know, which I think is a reality for a lot of startups. And I think the reason that now is the time we're at scale, you know, we're like 1100 people like EPD org is 600 people. We need processes. We need systems. We need like all of that. But at the same t…

AI assessment note: “the reason that now is the time we're at scale”

Q kind of hiring. One incredible hire that you made recently in the last couple of months was obviously with the new CPO. Tell me, obviously you came from incredible tenure at Facebook. The question I have is, like, what does it take to attract world-class talent like this, and why did you decide now was the right time to bring in that tenured, incredible-logoed exec, and now being that time?

A Well, I think there's a couple reasons we hired Karandeep, right? The first one, we wanted someone that had both B to B and consumer experience, which I think was very important for us, because with what we're building now, and I'll chat about it a little bit later, but It's incredibly focused on both the end user, the employee and employees and managers, but also the controllers and the admins and the finance team, right? Like there's this two pieces of the product. So we wanted someone who like had experience and kind of like doing both. So that's what I think one of the main reasons we hired him. And two, I think like he works super well with us. He was an engineer by background that also ran product, but he also, I think biggest plus a lot of smart product engineering people is that he was actually a GM. So he had like sales and marketing and like P and L accountability. That was like a huge deal for us because it wasn't like he was just doing his product there and hoping that people signed up. He had like real sales accountability, which makes him very good at the trade-offs between product engineering and customers, you know, which I think is a reality for a lot of startups. And I think the reason that now is the time we're at scale, you know, we're like 1100 people like EPD org is 600 people. We need processes. We need systems. We need like all of that. But at the same t…

AI assessment note: “the reason that now is the time we're at scale, you know, we're like 1100”

Q the same, and I think a challenge for me was when I looked at my hiring, which was not Great. Consistently across the board in the media company, transparently years ago, and it was very challenging. When we think about hiring mistakes, I think they're often the most prominent also just for early stage founders. What are some of the biggest hiring mistakes that you think you've made on reflection?

A I think executives that only had worked at big companies, and I think we were probably too early for them. I know this sounds cliche. We thought we weren't going to make these hires, but we did, because they seem like they could roll up their sleeves. But one of the books I read when I was on Adderall, I thought it was super good. Talks about this concept of the role being a university, right? Like what courses has this person taken? We need a people who are very fast to change and pivot because if we're changing strategies, changing direction, evolving, like we need someone who's very fast. And I think we hired a bunch of people for a while that were just very good at scaling, getting something that's working and making it bigger. And we had so much change of recs and strategy and direction. A lot of people couldn't keep up with the change.

AI assessment note: “I think executives that only had worked at big companies”

Q Do you find that having that bluntly realization and awareness really changes your product marketing? Because I love product marketing, but knowing that and then tailoring it does change a lot. How do you think about your product marketing today?

A Yeah, I think that one of the mistakes, if I were to go back, right, and like, think about things we did right to do wrong, First thing we did really right when we started is we had a very simple and clear message. Brex is the corporate card for starters. Absolutely no question what we do and who do we do it for. Then Brex started growing. I think we weren't focusing on too many things. We were doing card. We were doing bank accounts. We were doing bill pay. We were doing expense management. We were trying to serve small businesses. We're trying to serve enterprise. We're trying to focus e-commerce. And then you go to our website and it was super complicated. It's like, what do you do and who are you for? Right? And I think that happened like too quickly. And I think now we're kind of like shifting And I think that's a big thing, you know, around product marketing and just like the product strategy in general, right? Like I think the way we think about the world today is we are going to help your company move faster. I think that's a lot of how we're thinking about our products and how we're going to put into product marketing.

AI assessment note: “the way we think about the world today is we are going to help your company move faster”

Q with you there and. Some incredible people you've got around the table. The final element on the fundraising was the one hundred and twenty five million dollar basis round. Can I ask, with such an injection of capital, how does one think about Capital efficiency today. You mentioned about kind of not touching the series B when you raise the series C. How do you think about capital efficiency today?

A I think that for a fintech company, just having a big balance sheet is very important, right? So a part of the money raised is just, you know, to sit there for a rainy day. I think that, you know, having that is super important. In terms of capital efficiency, I think that, you know, you should save on some stuff and like not save on others. So for example, I think like you shouldn't save on employee comp. If there's good people and you want to hire them, like, and you have to raise everyone else's salary just to hire this person because, you know, they're more comp and you need to be fair to everybody, like, do it. Don't save on that. But try to hire maybe less people, um, and do, you know, have your people work more and don't spend on, you know, a lot of, like, stupid stuff, like sculptures in the office and, you know, expensive furniture and stuff like that, right? Like, Be frugal with things that don't matter, but people is the thing that matters the most, so I say invest in that.

AI assessment note: “In terms of capital efficiency, I think that, you know, you should save on some stuff”

Q the founding team there, I do want to move a layer beneath to the team itself, obviously the element that drives all companies, the people behind them. You've seen growth almost like never before seen with Brex, including the team. So a question from one of your own team and your CFO, Michael, how do you think about hiring the very best And specifically, how has that changed over time?

A It definitely evolves. I think, you know, when you start working for the first time, I don't think this is true for everybody, but it's definitely true for us and a lot of our friends. You think that everyone that's good is kind of similar to you and your friends that you admire, right? So you kind of have this mold of people that, you know, hey, this person, you know, he's like book smart, and he has this, and he has that, and you know, so he's probably good. And You start, you undervalue probably like leadership and management. And I think sometimes you actually overvalue experience because, you know, you don't know how to measure a lot of these things. So I think it's definitely a process that has evolved a lot. It wasn't like a straightforward thing, but I think it's like someone good in programming. My last company is someone good today. The way I think about it today is I think there's a few things, but I think the thing I most look at is career delta. So where did they, you know, start and where are they based on like, how much time are they working? You know, things like that. So if you know, if they're like out of college, you know, I want to see like, what did they do in college or before college that let them get there? You know, like that was like above the expectation. If there's five years out of work, like what did they do that was really good in those five years…

AI assessment note: “The way I think about it today is... the thing I most look at is career delta”

Q the founding team there, I do want to move a layer beneath to the team itself, obviously the element that drives all companies, the people behind them. You've seen growth almost like never before seen with Brex, including the team. So a question from one of your own team and your CFO, Michael, how do you think about hiring the very best And specifically, how has that changed over time?

A It definitely evolves. I think, you know, when you start working for the first time, I don't think this is true for everybody, but it's definitely true for us and a lot of our friends. You think that everyone that's good is kind of similar to you and your friends that you admire, right? So you kind of have this mold of people that, you know, hey, this person, you know, he's like book smart, and he has this, and he has that, and you know, so he's probably good. And You start, you undervalue probably like leadership and management. And I think sometimes you actually overvalue experience because, you know, you don't know how to measure a lot of these things. So I think it's definitely a process that has evolved a lot. It wasn't like a straightforward thing, but I think it's like someone good in programming. My last company is someone good today. The way I think about it today is I think there's a few things, but I think the thing I most look at is career delta. So where did they, you know, start and where are they based on like, how much time are they working? You know, things like that. So if you know, if they're like out of college, you know, I want to see like, what did they do in college or before college that let them get there? You know, like that was like above the expectation. If there's five years out of work, like what did they do that was really good in those five years…

AI assessment note: “the thing I most look at is career delta”

Q Has it changed how you approach board management today with Brax?

A I think so. Being on the other side, I now see, I was like, oh, wow, there's all these things that I'm seeing that I feel that I can share that they're not seeing because they're in the day-to-day. And I think I'm now more open to People from the outside that are seeing things and sharing with me that I may not see because I wasn't that seat. Does that make sense? Like before I was like, no, it doesn't make sense. Like people have no confidence in the business or what they say. And now I'm like, obviously not nearly as much confidence in the business as the management. I feel I have like some interesting ideas. So that's probably true on the other side too. You know, there's probably people that can give me like super interesting insights that I should consider a lot more. So it made me more open, I think.

AI assessment note: “I think so. Being on the other side... So it made me more open”

Q Why did you decide to go to new customers with a new product? Was it just advice? Was it looking for growth in new segments? What was the thinking there?

A I think it was probably overestimating the Our execution ability. We started Brexit with 20 people, and we're like, okay, we have 500 now, so we put 20 for this product, 20 for that product. I mean, that makes sense, right? And that's not how it works. Focus is super important, and I think we probably, we're trying to do too many things at once, so we were like, why not make this one of the bets? One of the five or six or seven things that we're doing. But then there's other than so many competing priorities. It's like, what goes in your homepage of the website? What are your salespeople doing? Where's your management spending time? Because like, you don't have that many Top leaders in a company. Where are they focused on? If you don't make that super clear, your execution just gets, like, slower.

AI assessment note: “I think it was probably overestimating the Our execution ability.”

Q Has it changed how you approach board management today with Brax?

A I think so. Being on the other side, I now see, I was like, oh, wow, there's all these things that I'm seeing that I feel that I can share that they're not seeing because they're in the day-to-day. And I think I'm now more open to People from the outside that are seeing things and sharing with me that I may not see because I wasn't that seat. Does that make sense? Like before I was like, no, it doesn't make sense. Like people have no confidence in the business or what they say. And now I'm like, obviously not nearly as much confidence in the business as the management. I feel I have like some interesting ideas. So that's probably true on the other side too. You know, there's probably people that can give me like super interesting insights that I should consider a lot more. So it made me more open, I think.

AI assessment note: “So it made me more open, I think.”

Q Is it, like, specific, like, hey, I'm raising X and X, am I doing it for my ego, or is it more general, do you feel like I'm getting ahead of my skis here? Like, do you go specific, or just kind of broad?

A I think for me, it's like, I think about a decision, and I think they already know me super well, so they're like, okay, like, let's think about this. Like, do you really want to do this, or is it like an ego thing, you know, and whenever they bring that up, I'm like, okay, let me really think about this, right, because a lot of times, very smart people, this is the thing about smart people, they rationalize anything, but the reality is, like, intuition comes first, rationality comes second, so you want to do something first, because of whatever, like, you're feeling like it, and then you create some, like, narrative in your head to justify it, and that's very normal, it happens to everyone. The problem is, like, you can't think you're immune to it, you're too rational, I'm too rational, like, that never happens to It's not true. Like, it happens for everyone. And I think having people that can be, like, your rational angels to, like, make sure that, you know, this is actually the thing, or you're just trying to do whatever you want to do, I think is important.

AI assessment note: “do you really want to do this, or is it like an ego thing”

Q Is it, like, specific, like, hey, I'm raising X and X, am I doing it for my ego, or is it more general, do you feel like I'm getting ahead of my skis here? Like, do you go specific, or just kind of broad?

A I think for me, it's like, I think about a decision, and I think they already know me super well, so they're like, okay, like, let's think about this. Like, do you really want to do this, or is it like an ego thing, you know, and whenever they bring that up, I'm like, okay, let me really think about this, right, because a lot of times, very smart people, this is the thing about smart people, they rationalize anything, but the reality is, like, intuition comes first, rationality comes second, so you want to do something first, because of whatever, like, you're feeling like it, and then you create some, like, narrative in your head to justify it, and that's very normal, it happens to everyone. The problem is, like, you can't think you're immune to it, you're too rational, I'm too rational, like, that never happens to It's not true. Like, it happens for everyone. And I think having people that can be, like, your rational angels to, like, make sure that, you know, this is actually the thing, or you're just trying to do whatever you want to do, I think is important.

AI assessment note: “I think for me, it's like, I think about a decision”

Q Can I ask, the biggest problem that I face is determining what to say yes and no to and how to prioritize my time. How do you determine what to say yes to versus what to reject as CEO today?

A So, you know, in that thing about things you have to improve, I think I may say yes to too many things. So I'm not sure if I'm the best role model for that. So many things happen very serendipitously. So for example, like our CFO, Michael, we met because he was The brother-in-law of my Stanford professor brought in a lawyer whose girlfriend worked at a company that, you know, he worked. Like, it was so random, and I might have not taken that meeting and maybe not met him, right? And he's like, you know, been super great for the company. So sometimes, like, you know, I always keep thinking about what could have happened, but that's probably not the most productive way to think about it.

AI assessment note: “I think I may say yes to too many things. So many things happen very serendipitously.”

Q I do have to ask, is that not kind of suffering unnecessary dilution then? And also, will the best partners who can write for you, so to speak, will they not always be there if they are right for you? And that's almost quite a good litmus test.

A I think that, you know, that's why I say when the price is right, if someone, you know, We always kind of had an idea of where we wanted the price to be, and we kind of, like, always were very transparent about that. So I don't know if this is a formula that people can use it or not, but the way we always fundraise is like, hey, we went there and we said, hey, this is kind of the price we want, and we're going to work until we get to a point where this works. And a lot of times people are okay, like we can do it now, right? Instead of letting the market decide what the price is, I don't know if that's like a formula that, you know, is the most optimal, but But we always found it to be the most transparent instead of, you know, negotiating back and forth and saying, like, hey, you know, this VC gave me that, that VC gave me this, please match it, and kind of, you know, just kind of, like, negotiate on price. I think that creates, like, a bad relationship with the VC. We were just very transparent, like, hey, like, this is the price we won. We're going to choose, basically, you know, how much a partner can help, and, you know, let's move on.

AI assessment note: “We were just very transparent, like, hey, like, this is the price we won.”

Q I do have to ask, is that not kind of suffering unnecessary dilution then? And also, will the best partners who can write for you, so to speak, will they not always be there if they are right for you? And that's almost quite a good litmus test.

A I think that, you know, that's why I say when the price is right, if someone, you know, We always kind of had an idea of where we wanted the price to be, and we kind of, like, always were very transparent about that. So I don't know if this is a formula that people can use it or not, but the way we always fundraise is like, hey, we went there and we said, hey, this is kind of the price we want, and we're going to work until we get to a point where this works. And a lot of times people are okay, like we can do it now, right? Instead of letting the market decide what the price is, I don't know if that's like a formula that, you know, is the most optimal, but But we always found it to be the most transparent instead of, you know, negotiating back and forth and saying, like, hey, you know, this VC gave me that, that VC gave me this, please match it, and kind of, you know, just kind of, like, negotiate on price. I think that creates, like, a bad relationship with the VC. We were just very transparent, like, hey, like, this is the price we won. We're going to choose, basically, you know, how much a partner can help, and, you know, let's move on.

AI assessment note: “the way we always fundraise is like, hey, we went there and we said”