20VC: Brex's Henrique Dubugras on Advice from Evan Spiegel and Eric Schmidt on CEOship, The Biggest Hiring Mistakes When Scaling, What Everyone Gets Wrong with Product Messaging and When is the Right Time to Launch Secondary Products

Henrique Dubugras is the Founder and CEO @ Brex, the company re-imagining financial systems so every growing company can realize its full potential. To date, Henrique has raised over $1.1BN for Brex from some of the best including Ribbit, Greenoaks, DST, IVP, Caffeinated Capital and Elad Gil to name a few. Henrique is also a board member at Mercado Libre. Prior to co-founding Brex, Henrique co-founded Pagar.me, there he scaled the company to $15BN in GMV and over 100 people before selling the company in 2016. In Today’s Episode with Henrique Dubugras You Will Learn: 1.) The Founding of Brex: What was the founding a-ha moment for Henrique and Pedro with Brex? What advice did Evan Spiegel give Henrique when it comes to being a great CEO? 2.) Hiring: The Trials and Tribulations What have been Henrique's biggest hiring mistakes? How do founders know when they are ready to bring in the seasoned exec vs the younger jack of all trades candidate? What have been Henrique's biggest lessons in what it takes to hire true A* talent? Where does Henrique see other founders make big hiring mistakes? 3.) Product Expansion and Marketing: How does Henrique assess when is the right time to release a second product? What have been Henrique's biggest mistakes and lessons when it comes to product marketing? How can one retain the simplicity of product messaging with scaling the product? Brex expanded the product too far, too fast. How did they walk it back so successfully? 4.) Henrique: The Leader How does Henrique approach his own relationship to money today? How has it changed over time? What luxury expenditure has Henrique made over the last 12 months that he feels is worth it? How does Henrique think about ego management? What does he do to keep his in check? Item’s Mentioned In Today’s Episode with Henrique Dubugras Henrique’s Favourite Book: The Innovator's Solution: Creating and Sustaining Successful Growth

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

• 0:00Harry Stebbings?

  Welcome back. This is 20 VC with me, Harry Stebbings. Now, when I have guests on the show for a second time, I always think a lot about their change and their rate of development from their first show. Henry Ward at Carter stands out for this perspective, but also today's guest was just incredible to see their rate of growth from the first episode. And so with that, I'm thrilled to welcome back a friend in the form of Enrique, founder and CEO at Brex. The company reimagining financial systems so every growing company can realize its full potential. To date, Enrique has raised over 1.1 billion dollars for Brex from some of the very best, including Ribbit, Green Oaks, DST, EVP, Caffeinated Capital, and Elab Deal, to name a few. Enrique is also a board member at Mercado Libre and prior to co-founding Brex, Enrique co-founded Pagarmi.

• 0:42Harry Stebbings?

  There, he scaled the company to 1.5 billion dollars in GMV and over 100 people before selling the company in 2016. But before we dive into the show today, in an increasingly competitive venture capital landscape, it's more important than ever to have the right data to keep your edge. Core Signal's high-quality alternative data is a cornerstone for investors seeking to identify opportunities, quantify startup traction, and assess risk. Leverage more than 20 continuously refreshed data sets collected from public web sources. Used in combination, these sources offer a 360-degree view of any selected company or industry. Head over to coresignal.com/20vc and download a free ebook that explains how VCs today

• 1:24Harry Stebbings?

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• 2:10Harry Stebbings?

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• 2:54Harry Stebbings?

  If you're a founder, you can launch your company at stack.angelist.com/20vc. Whether you're a founder or thunder, you're in great hands with Angel List. But that's enough from me. So now I'm so excited to hand over to a fantastic founder, a friend in the form of Henrique, co-founder and CEO at Brex.

• 3:16Speaker 01

  You have now arrived at your destination.

• 3:19Harry Stebbings?

  Henrique, this is such a joy to do. It's been far too long since our last one, but thank you so much for joining me again today.

• 3:25Speaker 02

  Thank you so much for having me. I was excited to be here.

• 3:27Harry Stebbings?

  Listen, I'm thrilled about it, but I want to start, 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?

• 3:39Speaker 02

  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 B2B 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. It's like, how come you have raised $5 million and you can't get a card to pay for your SaaS and AWS bills? And we did a card that did just that. So that was the original insight back in 2017.

• 4:09Harry Stebbings?

  I mean, I love it and it also sounds kind of hilarious that you raised a ton of money and then can't get an account. I wanted to use today, honestly, as a little bit of an advice session because like, and you didn't know this, but like, I'm obviously scaling my teams across media and fund 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, Enrique?

• 4:35Speaker 02

  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 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 are 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. So 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.

• 5:20Speaker 02

  And I'm here like not reading anything. I think like trying to be something that I know versus just embracing. And the fact is for me, I can't read books, but I learned a lot through people. So I forced 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 for learning. So as soon as I admitted my strengths and my weaknesses and was more authentic around what I'm good at, what I'm bad at. And like double down on strengths instead of trying to focus on the weaknesses, everything got better.

• 5:47Harry Stebbings?

  I mean, I totally agree with you. First, I can badly read a tweet, let alone a book, and I don't have ADHD, Enrique. So 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?

• 6:06Speaker 02

  I think there was this New Year's, honestly, I know it has to do with, I'll double down on 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 I 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 those 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 at 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 your really building relationships with the team and customers and all that. And I stopped medicating and actually things got a lot better.

• 6:51Speaker 02

  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 them.

• 7:01Harry Stebbings?

  Can I ask, in terms of like the insecurity there in terms of like, oh, I'm not reading as much as others. When you look at your insecurities today as a leader, what do you think the insecurities that remain are for you that you consistently find yourself grappling with?

• 7:14Speaker 02

  I think the biggest insecurity for me and now Pedro and I, we figured it out and over the years is like, hey, I don't particularly like management. That kind of sucks, right? Like, how can you be a CEO if you don't like managing people? That seems like a core part of the job. And obviously this is me very insecure and then that's how Pedro and I, we kind of found our split around external CEO and internal CEO. Pedro actually loves management and he hates doing a lot of the external stuff that CEOs do. And I don't really like management, but I like a lot of the other jobs a CEO has to do. And we created this partnership that worked super well for us and which both of us can execute our roles and be the best at what we're good at. It still hangs till today, but we learned how to deal with it.

• 7:51Harry Stebbings?

  I mean, totally 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?

• 8:10Speaker 02

  I think executives that only had to work 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 seemed like they could roll up their sleeves. But one of the books I read when I was an adult, and 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.

• 8:51Harry Stebbings?

  Can I ask, how do you determine that plasticity to change to speed of execution changes? In the pre-hire process, what questions can you ask? What signals derive plasticity to not just be rigid to the more incumbent style of working?

• 9:07Speaker 02

  Yeah, there's a bunch of questions, but I think smart executives, they know the answers to all of them. I think it's looking through the experiences, even if at a big company, how to take something off the ground? Or would they always hand it something that was already working and just say, optimize it, make it better? I think like the zero to one or like the changing strategies, right? Like, that's the part that you should dive deep into the experiences and see if they had to do that many times? Or have they just got something that was working and made it incrementally better every year?

• 9:37Harry Stebbings?

  Often it's the VCs who kind of push those great candidates, but also maybe inappropriate candidates on founders. Did you feel an insecurity with your investors where you asked 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?

• 9:55Speaker 02

  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 they want your support, but like, this is our company and we're going to make what we think is best. Because the reality is like, if it doesn't work, the accountability is 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 times are right, some are wrong.

• 10:27Harry Stebbings?

  I love that. This is not one of the problems we have. We spoke about hiring. And one incredible hire that you made recently in the last couple of months was obviously with the new CPO. Tell me, obviously it 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?

• 10:50Speaker 02

  Well, I think there's a couple of reasons we hired Karen Deef, right? The first one, we wanted someone that had both B two 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 worked 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.

• 11:35Speaker 02

  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 time, we had a hunch that this would be true, but now that we're working with him for a while, he definitely can tuck in his leaves and do real work. He's definitely like doing real, real work and not just managing from above.

• 12:14Harry Stebbings?

  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?

• 12:27Speaker 02

  Yes, and I'll tell you exactly how it happened. 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 happened 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 $5,000 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 another culture 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.

• 13:10Speaker 02

  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 $5,000 bottle of wine 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 1% of times that things go off, right? Get to this story that I just told and extrapolate to basically everything in the company. That's how companies get slow. And honestly, that is a problem that we started experiencing. We seen, saw so many of our customers experiencing. And we decided to honestly like start building products to solve it because it was kind of like our own need.

• 13:55Harry Stebbings?

  So what is the solution then? To not have that process, to not have the rules and to instill trust at scale? What is the solution then?

• 14:03Speaker 02

  Yeah, I think the cost is considering the cost of flowing down the organization as a counterbalance to the process. I think when a lot of teams make these decisions, they don't consider it's like, okay, like how much it actually costs to lose that $5,000 bottle of wine? Versus how much does it cost to 99% of our people have to do a lot of grunt work with their expenses? Get many approvals and et cetera upfront? And actually like thinking about that cost when making a decision to implement a process. And the reality is like some of these tail events, right? So for example, security, if someone hacks Brex, it's the end of Brex, right? It is worth adding a lot of process to make sure that no one hacks Brex because the 1% of the time it happens, it's the end of the world.

• 14:45Speaker 02

  Someone buying something that they're not supposed to, it's bad, but it's not the end of the world. You know, like there's a cost associated to it. And what we did with our product is that we built a lot of functionality now. So we're launching this product, this will give you some context called Empower. The thesis behind the product is by making the employee experience better around expenses that actually increases compliance. Because the reality today is that people hate doing their expenses. I'm sure you can relate. delay to this, you know, you have to keep all these receipts, you hate doing it, you type everything up like it's a pain, right? So anyway, so like people have like all these receipts, they have to do it and they hate doing it, they're months delayed. And then managers, they get all these approvals and they have no clue, like, you know, no one actually looks at it, they just rubber stamp and say approve because you trust your team, right? So the process is actually not doing that much.

• 15:30Speaker 02

  And then finance teams, they need to be like the money police, they need to be the police who's like checking people and bugging people like, what is this? Why do you do this? And having that role. And what we're doing is we're inverting the whole cycle because things go crazy. Finance teams add even more process, more bureaucracy, gets the employee experience even worse, the manager experience even worse. And it becomes this like negative cycle. What we're doing is we create a product in which like you swipe your card and basically you get the receipts automatically. There's nothing else you can do for the majority of receipts, you don't have to do your expenses. Because you don't have to do your expenses, you're already in compliance. And managers, instead of showing them everything that they need to approve and showing every transaction, we only show them things that are out of policy, right? So they have like three or four things to approve.

• 16:12Speaker 02

  And therefore that creates like a positive flywheel in which, you know, employees are doing their expense on time. Managers are actually a very good layer of review because they have three things to look at and they can say, hey, this is out of policy, this transaction, Harry's team spent a transaction. They're not supposed to fly business class, but they flew business class. And this is the reason why, and you can approve or not approve. But that's the context and you have like one thing to do it. And then, as you can see, the process is focusing on the one or two percent of things that are wrong. Instead of making the 99% do something that they don't need to. So how do you apply that mentality across the entire company?

• 16:44Harry Stebbings?

  Can I be so bold and ask, is this in response to Ram's motto of like, we help you spend less? Theirs is always like, we help you save, we invert the business model, we don't encourage you to spend, we help you save. Is this in response to that, do you think?

• 16:59Speaker 02

  Ramp was always like something super interesting for us because it was the first competitor that was like an insurgent, someone who was coming and growing. That wasn't like the, the big guy, JP Morgan and American Express. And, and we started thinking about, it's always blog posts or sites, they seem to be growing, like, are we doing something wrong? Is this spend less thing makes sense? Like, maybe we should just do that, right? Like, it seems to be working. For them. And then we had really an idea. Let's go talk to our customers. Let's go ask our customers. What are their problems actually are? And we went to the mindset almost of like, we're gonna hear them say, especially a little bit larger customers. We're gonna hear them say, oh, my God, yes, I'm trying to reduce my spend. I'm trying to spend less. My credit card bills are too high.

• 17:39Speaker 02

  I'm trying to reduce it. And when we actually talked to them, what they said is like, yeah, I can like reduce my credit card bill for five percent. Like, that doesn't change my business. Like, that doesn't change my life on reducing my credit card bills for a little bit. The problem is becoming big and slow. It's exactly what you said. The more people I hire, the slower I am. My employees hate the experience of doing expenses. Like, a lot of people just hate, they think, they have this feeling of that they're distrusted, right? Like, they have this feeling that, hey, they're treating me like I'm trying to steal money from the company with all this bureaucracy and all this process. And finally, it seems like I hate being the person that implements a process that prevents people from doing good work. I want to be the person that implements a process that allows people to do their work.

• 18:19Speaker 02

  And then that's when we said, actually, no, what they're doing doesn't make any sense for a lot of our customers, maybe for their customers. The direction that makes sense in the product and the expense is helping companies move faster. That's what matters for a lot of our customers, and that's the direction that we're going.

• 18:33Harry Stebbings?

  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?

• 18:46Speaker 02

  Yeah, I think that one of the mistakes, if I were to go back and like, really 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 startups. 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 are you doing? Who are you for? Right? And I think that happened like too quickly. And I think now we're kind of like shifting back. 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.

• 19:30Speaker 02

  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 gonna put it in the product marketing.

• 19:39Harry Stebbings?

  When you look back at that and the learnings associated, how do you advise founders on the right time to expand product line? You can always go deeper, you can always get more customers for one product. There's always more customers and then there's the right time and there's a wrong time to expand product line. How do you advise them on when's the right time to expand?

• 19:56Speaker 02

  And we didn't do this, by the way. I think that if you're expanding to it's the same customer that you're serving with a product that makes your current product better. Because that product exists, so you're gaining not only you're selling this new product, but your old product is better because you have this new product. And it's the same customer. I think that that's like a good expansion and you should do it whenever you feel that your core product is getting to a mature state. If you're trying to go with a new product to a new set of customers that you don't serve today, which honestly is what we did. That's really hard. That's like starting a company from scratch.

• 20:32Harry Stebbings?

  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?

• 20:39Speaker 02

  I think it was probably overestimating our execution ability. We started Brex with 20 people and we're like, okay, we have 500 now, so 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 were 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.

• 21:18Harry Stebbings?

  So I see this a lot with boards that I'm on and the truth behind it most often is bluntly a lack of confidence. And a risk mitigation strategy of shit, I don't actually know which one's gonna hit. So if I have these six teams of 20 and across six different products, one will hit or two will hit and we'll be okay.

• 21:38Speaker 02

  Yeah.

• 21:38Harry Stebbings?

  And that tends to be the Reason, the lack of confidence in conviction.

• 21:42Speaker 02

  Yeah. I agree with that. And I'll tell you exactly what happened for us is like when a company grows, you start having so many problems that talking to customers starts like not being like a super big priority. Now I talk to customers a lot and I force myself to talk to customers like every week. But like, I think for a good year and a half, I just had so many things going on with fundraising and hiring and providing all these things that you just forget to talk to customers. And I think it's only by talking to customers that you build a real conviction. And sometime last year, Peter and I, okay, like this is like crazy. So we're going to spend weeks now talking to customers like many every week. And that's, I think, when we built a lot of conviction to say, hey, actually, we're not going to focus on all these things. All these things are not the priority. Priority is now this, and we have full conviction and let's focus and execute.

• 22:26Harry Stebbings?

  You mentioned that you almost take in terms of going too broad, too early and overestimating execution ability. And now very kind of brilliantly bringing it back and you've done it very well. For those that have done the expansion and haven't brought it back yet, what advice would you give them in terms of what it takes to go back a step and simplify again?

• 22:46Speaker 02

  I got this advice from Eric Schmidt, like spend 90% of your time or 90% of your revenues. I think that a lot of companies, when they get to some scale, some things aren't working. And sometimes it's important to understand what's working as much as what's not working. If you did a lot of bets, you'll find things that are working. Just cut out the rest and focus on that.

• 23:05Harry Stebbings?

  My question to you, how long do you give those bets? This is the hardest one for me. Is it six months or is it a year? And you don't want to leave what we call in the UK like a smelly fish to dry. Do you know what I mean? You don't want to give it too long, but you also don't want to give it too short.

• 23:20Speaker 02

  I would say that it's hard to give a general framework, but I would say that you can have some small teams working on it in the side. The problem is like you need to make them like fairly independent to make it work. It can't, it needs to be like in a way that like you have the whole company priority. And it's fine to have a few bets on the side like going. Problem is when you have too many company priorities. So the two pizza team thing that Amazon has, I think it works to the extent that it doesn't, it can work in a siloed way. If your bets need like core platform. Investment, right? Like he needs the entire company to mobilize to make it happen. Then I would say like, hey, sequence it, like choose one. It's not that you're never going to do this bet again, just like you need a sequence set. Frank Slutman, the new book, he was, he talks a lot about making things sequential instead of parallel.

• 24:05Speaker 02

  So I think that's like a big lesson that he already knew. Hope, I wish his book was out a few years earlier, but I think it's true.

• 24:11Harry Stebbings?

  That is, I agree. I did read that book. I have to say it was probably one of the very few that I have read. A lot of these strategic decisions are decided at the board. You're now on the board of Mali, obviously with Marcos, incredible company, incredible entrepreneur. What have been some big takeaways for you from being on the board? And how has it changed your view of leadership?

• 24:29Speaker 02

  It's been very interesting to be on the board, honestly. I joined because I really like Marcos and the team and I love Latin America. So it's like a way to stay connected, but I feel that I learned so much about what are good things about a board? What are bad things about a board? And I have other friends that are on other boards and some other friends. They say that the board meeting is all about talking about the public markets and how the market is going to react, all this. And I haven't heard in the Mali board, one discussion about the markets, one discussion about investors and the share price. It's all product and strategy, product and strategy, product and strategy. And I think that's super inspiring. Like we want to have a public company board that we talk about product and strategy and not about what's the flavor of the day of the market. So I think that's a big learning for me.

• 25:11Harry Stebbings?

  Has it changed how you approach board management today with Brex?

• 25:15Speaker 02

  I think so. Being on the other side, I now see it 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 like obviously not nearly as much confidence in the business than 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 maybe more open, I think.

• 25:48Harry Stebbings?

  So that's one final one that I am just too interested by and it's one that I think about a lot as we grow up and as we do well luckily. But it's like relationships to money in particular. Well, there's a couple, but relationships to money is one. How do you think about your relationship to money and has it changed over time?

• 26:02Speaker 02

  I think for me, both in the company and personally, I think it changed over time. Coming from Brazil, money was very scarce, right? Both personally and in the company. Saving it and preserving it and like it was the main thing. Hey, let's make sure it doesn't run out. And that was the sentiment. So I need to accumulate money to save. So I have like this peace of mind, right? I have this like insurance that things are gonna go well. And then you, we grow and we get to a point where like, look, yeah, we have like many years, like we're not gonna pay, not pay our credit card next month, right? And I think the best use of money is growth, both for the company and then personally. I have no issue spending money to go to a trip to meet someone that I'm gonna learn a ton from, right? Like I have no issue hiring someone to teach me something that I'm very interested in.

• 26:45Speaker 02

  Like I think money, both for the company and personally allows for growth, right? It's a fuel to grow. I think that's the way I think about it, both personally and for the business.

• 26:54Harry Stebbings?

  Are there any other things which you now spend on that you didn't before? Could be for growth or could be for enjoyment. Like mine, I have a PT, personal trainer. He's egregiously expensive. Like he's got an hourly rate that's higher than mine and yours, but he's fantastic and it's worth it for me. Are there any others that actually you found it is worth it?

• 27:12Speaker 02

  I think after work from home, before it didn't make sense, but after work from home, having a chef changed my life completely. I eat so healthy and before COVID, I was like serving out, driving off deliveries like cold and it's hard. And I think that now, I think my health increased a lot because of it. So I think it's the best investment.

• 27:30Harry Stebbings?

  No, listen totally. The final one I promise is just like relationship with ego as well. How do you think about your own ego and how do you think about ego management?

• 27:39Speaker 02

  Totally. And look, man, I've been having this problem since I'm 14, right? Like first time I was in the press, you know, in Brazil, saying I'm the genius and the next whatever, you know, I was 14. And you have all these smart people and journalists, you start believing it, right? You're like, okay, like, yeah, I believe it. I think the important piece about ego is like understanding that you're not immune. It can't happen to you. You, right? Like you can't think you're too much of yourself. So I think about is like, how do I build the systems and checks and balances? That if that is the case, I have people and systems around me that keep me on check and tell me if it's happening. I have a few people in my life that I had very intentional conversations saying, hey, if you think I'm having like ego problems, like you need to tell me and I'm gonna listen.

• 28:22Speaker 02

  And I think you need those people and checks and balances. It's hard for you to know yourself if it's happening to you.

• 28:27Harry Stebbings?

  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? Do you go for specific or just kind of broad?

• 28:38Speaker 02

  I think for me is 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 wanna 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 wanna 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. It's not true. Like it happens to everyone. And I think having people that can be like your rational angels. So like, make sure that, you know, this is actually the thing.

• 29:22Speaker 02

  Or you're just trying to do whatever you wanna do, I think is important.

• 29:24Harry Stebbings?

  That's the hardest thing for me. I always say, well, actually, when you break it down, it makes sense for these three reasons. And that's why I'm doing it. You're like.

• 29:31Speaker 02

  Yeah.

• 29:32Harry Stebbings?

  Tell me, final, final, final one. Head versus heart. When you have those decisions, do you listen to your head or your heart?

• 29:38Speaker 02

  I've become more intuitive over time. I used to be very focused on rationality and how to become more rational. I'm like less that now. Historically, all of the heart decisions have been better than the head decisions. So I would say more heart these days.

• 29:52Harry Stebbings?

  All my worst mistakes investing wise have been because I thought too much. Which is probably worrying for the investing world, but I do want to move into my favourite, Henry Gay, which is a quick fire answer. I say a short statement, you give me your immediate thoughts. Does that sound okay?

• 30:06Speaker 02

  That sounds okay.

• 30:07Harry Stebbings?

  Listen, we mentioned the reading earlier quite a few times, but I am interested. When you think back on the books you've read, which stand out most to you?

• 30:13Speaker 02

  I think business wise, one calls innovative solution. I think likewise atomic habits are probably the two favourite ones.

• 30:20Harry Stebbings?

  What's the hardest element of your role with Brex today?

• 30:23Speaker 02

  Focus. You have limited hours. The company has a lot of stuff going on. How do you spend your time?

• 30:28Harry Stebbings?

  Tell me, what would you most like to change about the world of startups?

• 30:30Speaker 02

  I want it to become more distributed.

• 30:32Harry Stebbings?

  How would you most like to be described by your team? This is like three to five words which surmise you and your leadership.

• 30:38Speaker 02

  Compassion. I think trustworthy. I think energetic. I think thoughtful and I think crazy.

• 30:47Harry Stebbings?

  Oh, I like it. I love the paradox of the last two, thoughtful and crazy. Tell me, what's your biggest weakness and what are you doing to change it?

• 30:54Speaker 02

  Honestly, man, I think sometimes I get, I have like ego stuff, ego problems and I need my systems to bring me back down to earth.

• 31:00Harry Stebbings?

  Man, I totally agree. And I always think like 99% of the time you're angry is because of ego or insecurity on your own behalf. Tell me, next 10 years for you and for Brex is 2032. Where is Brex and what do you want the next 10 years?

• 31:13Speaker 02

  I think Brex is the financial operating system for businesses around the world, number one. And I would love to in 10 years, people know that it's a reality that if you use Brex, your company moves a lot faster and you win. I think that's the, what I would love to give Brex to do. It's like if you use Brex, you will win because they're going to move faster. If that's true and we're helping a lot of our customers win, I think that's winning for us.

• 31:36Harry Stebbings?

  Henry Gay, this has been such a joy to do. Honestly, man, I love our discussions. I can't thank you enough for putting up with me using you as a therapist and a counselor. But really, I loved it. So thank you so much.

• 31:46Speaker 02

  Thank you so much for having me. I had a blast.

• 31:50Harry Stebbings?

  I have to say, I really do love my relationship with Enrique. A wonderful person, incredible company being built and such exciting times ahead for Brax. If you'd like to see more from us behind the scenes, of course you can on 20vc.com. But before we leave you today. In an increasingly competitive venture capital landscape, it's more important than ever to have the right data to keep your edge. Core Signal's high-quality, alternative data is a cornerstone for investors seeking to identify opportunities, quantify startup traction and assess risk. Leverage more than 20 continuously refreshed data sets collected from public web sources. Used in combination, these sources offer a 360-degree view of any selected company or industry. Head over to coresignal.com/20vc and download a free ebook that explains how VCs today

• 32:35Harry Stebbings?

  use alternative data to outperform their competition. That's coresignal.com/20vc. And speaking of incredible tools like Core Signal, that from websites and online stores to marketing tools and analysis, Squarespace is the all-in-one platform to build a beautiful online presence and run your business. There are three things for me that really stood out about Squarespace. First, mobile-optimized websites. All websites are optimized for mobile in a way that content automatically just adjusts so beautifully, so your site looks great on any device. Pretty awesome. Second is the email campaigns. Squarespace makes it super easy to grow and engage your audience with Squarespace email campaigns. And finally, SEO tools. Squarespace takes the guesswork out of SEO, so you'll get found in search by more people more often.

• 33:19Harry Stebbings?

  And if that wasn't good enough, go to Squarespace.com/20vc for a free trial. And when you're ready to launch, use the offer code 20vc and you'll save 10% off your first purchase of a website or a domain name. And last but by no means least, the incredible team at Angel List. They've been a key partner for me in managing my investments. I love using the Angel List platform because it abstracts away all the complexity and operational burden of fund management. So whether you're running SPVs, a traditional venture fund like me, or even a rolling fund, Angel List has you covered. I'm also, though, super excited about their new product, Angel List Stack, which is purpose-built for founders. With Angel List Stack, you can create a fundraising-ready startup in just a few clicks. Angel List handles your company's incorporation, banking, cap table and fundraising process all in one single place.

• 34:03Harry Stebbings?

  This allows founders to focus on building. If you're a founder, you can launch your company at stack.angelist.com/20vc. Whether you're a founder or thunder, you're in great hands with Angel List.

• 34:14Speaker 01

  As always, I so appreciate all the support and I cannot wait to bring you an exceptional set of episodes next week.