July 2, 2021
Few people understand overlooked markets and opportunities as well as Christopher Schroeder. Under normal conditions of temperature and pressure, you could find Chris having a chat with a founder in Brazil or Pakistan as easily as you'd find him boarding a plane in Egypt or the Philippines. Now, he jokes, he can swing around the world in a day over Zoom.
Chris is a real global citizen, who truly embraces the mindset of giving first and learning from mistakes. For the past few years, he's been advising and investing in driven entrepreneurs in global emerging markets. At Next Billion Ventures, he focuses on South East Asia, Latin America, and the Middle East. His book, Startup Rising: The Entrepreneurial Revolution Remaking the Middle East, is an international bestseller.
As a founder, his startup HealthCentral.com was backed by top tier firms and sold to Remedy Health in 2011. Before that, he also helped The Washington Post enter the digital era as CEO of washingtonpost.newsweek and LegiSlate.com.
Today, Chris shares with us:
Chris, welcome to the podcast. This is a huge pleasure. We only met like a year ago, or I don't know how long ago it was. It feels like it's been a long time, but it hasn't been that long. Thank you for coming on the podcast. And I'm excited to talk to you today. We've got a lot of different topics that I'm looking forward to covering. And so it's a real pleasure to have you on.
Couldn't be more excited, man. Thanks for having me. This was great.
You first reached out because we both wrote a book, right. So there was a kind of a connection there. And then there's another thing we have in common, which is that we're both investing and supporting different regions that are not the classic US or Silicon valley or New York-based ecosystems.
We have a lot in common. I wanted to start off with, just to kick things off, with pulling something from your book. There's a quote that you had, which is: "Big top-down organizations think of people as problems to be solved. Bottom-up organizations think of people as assets to be unleashed." I would love your perspective on: what does a bottom-up organization look like day to day. And can you elaborate a little bit more on that quote from your book.
One of my favorite quotes from the book, actually from an extraordinary woman named Dina Sharif, – who runs a big entrepreneurship program at MIT now, but – she had actually worked with top-down organizations, helping in social impact, work in Africa, and then spent much of her life helping entrepreneurs.
And it's interesting. She talked about top-down organizations, meaning big government, big institutions, banks, and that kind of stuff, big NGOs. They say "You poor people, we here in Washington, or wherever, will solve YOU." But it wasn't so much bottom-up organizations as it was almost a bottom-up mindset, that people who believe at the end of the day, that women and men on the ground have a problem they want to solve in their teeth.
And no one has a better stake at wanting to solve that problem and the people on the ground. And they look around them and everyone around them as an asset to be unleashed. And so in a way, everything you've done, Brian – I got to tell you, as a quick aside, I sat in on your open all-hands meeting today, which was just fantastic. First of all, the fact that you did it open, I think it was fantastic. Cause all-hands meetings are usually internal, but you've particularly articulated the bottom-up because you literally were talking about Latitud as a platform for unleashing entrepreneurs on their terms, getting their needs met on the specific areas that they need them met.
And that's really what we're talking about when we're talking about unleashing the bottom-up because these folks know their backyards, they know their problems, and they just want to do nothing other than just solve them.
Thank you. That means a lot. Yeah. And I'm glad that, you know, we're kind of experimenting here with this. Rich Barton, who's a guy I admire a lot, he always talks about power to the people and that's kind of one of his mantras. How can startups give people more power in the organization and how can we really truly unleash this potential?
Yeah. I mean, it all starts at the premise level, right. And Dina captured a bit of the premise, but it has something that we all, you and I, know as former CEOs, at the end of the day.
The essence of also, which is leadership, which is: do you believe you're surrounded by people who are smarter than you? Do you believe you have people around you who are really thinking about things in different terms that can make the organization better? Do you think it is a we experience or an I experience?
And you wrote all the time in that wonderful book about how it was all about the we. And that's the essence of it. People need to feel free to be wrong. They have to have a wonderment in being wrong and having an ability to put out ideas based on experience of what they see on the ground. Plus data, not just anecdote, that allows us to help them to be unleashed because it unleashes our enterprise in a much more serious way.
Have you seen any cultural challenges globally? You've done a lot of work in the Middle East and Latin America. I can share that being wrong isn't as accepted. And I remember, just to kind of illustrate, that in our early days of Viva Real, we actually had – I wouldn't call it a core value, but something that we described as a behavior that we wanted to promote in the organization... This is in the early days, so it wasn't very eloquent, but we said: don't do stuff you think is stupid.
That was one of the values because there is a hierarchical... I remember the secretary that we hired in the early days, she would call me Don Mr. Brian. And I hated that because, you know, like, just call me Brian! There's this almost unnecessary respect for other people, when some of the greatest ideas that we had at Viva Real came from the intern who discovered Amazon Web Services before anyone else. And then we were able to scale. So how does culture play a factor there and how can we elevate those people to really get them to communicate their ideas and be leaders in an organization?
Two observations about what you're asking. I do stuff with Silicon Valley and invest here in the States, but most of my work, as you pointed out, is in rising markets. And I have a lot of focus in Southeast Asia. Now, some in Latin America, a little bit in Africa, fair bit in the Middle East.
All of them are very unique in their cultures and history and geographies. But what is astounding to me, Brian, is how much they share among them. In the problems they face and the opportunities they face just by being in a rising market. And this certainly is in the case of navigating last mile logistics, educating hundreds of millions of people who've never had a bank account to be able now to engage in financial inclusion, how to navigate regulation, which is uncertain... but a big one is the one that you're talking about, which is culture. And many of these places where I experienced, there's not really a culture of failure. I mean, many of these young people came up, their parents told them "you gotta be an engineer, you gotta be a doctor or you gotta be something that's really clear and understandable."
And all I can say is that even here in America, we love to say we love failure. Well, the fact is we don't love failure. Failure sucks at every level. But it is a learning. And failure as learning is a paradigm and cultural shift, which I've actually seen happening more and more, almost uniformly around the world.
And that I think in part is twofold. One is just the sense that transparency is a good thing. We should talk about our failures because we can learn about them. And if you talk about it, I'm willing to talk about it. And the second one is what you wrote about and what you lived in the company that you built overal,l is how you walk is what matters.
If you shoot someone for making a mistake, the culture knows that you can't make mistakes or at least talk about mistakes openly. You embrace – again, have a wonderment of saying "wow, I was wrong about that. And now look at what I learned. Look what I can do with what just happened." Well, that signal gets out there as well.
I think the nuance you said is unbelievably important, which is, you don't want people to be sloppy. You don't want people to be ill-prepared. And frankly, I don't like to have people make the same mistake twice. But even then, if there's learning and people are open about it and they say, "look, here's what went wrong, I understand what went wrong and here's how I'm going to fix it, here's what I learned" – that tends to be viral, frankly. It just tends to have other people feel safe and comfortable and embrace the same.
I liked that. And on the top of culture, I'm a big fan of Ben Horowitz. And the book What You Do is Who You Are is just one of the most relevant books I've read on culture and business.
Dead on. There are maybe three books in my life that I wish I had when I was running companies. Two of his books are top of those three. And it's just because he gets it and understands it so well, as you say.
How did you become such a voracious reader? You consume books like crazy. I think I heard a podcast where you were reading this insane volume of books. How do you make that happen? I like to read, I've been reading a lot to my kids every day. But it's hard to sit down and pile through these books. What does that come from for you?
First of all, what a blessing that you're doing that for your children. Cause they'll be readers because of that. It's something they'll do. And I love books and I read a lot of books, but I read all the time anyway. I mean, I just read blog posts and I read obviously emails where people are having thoughtful exchanges. My WhatsApp is full of of thoughtful exchanges. So it's all about processing, but to books per se, I look at every book as another life I get to live.
And I learned so much from them in what I read. Mostly I read nonfiction and history, but a little bit of fiction. And every one of them helps me think about the world in a different way. It helps me piece together things. And it really is about discipline. I've been blessed as a fast reader. But I had a very good friend, a great entrepreneur, actually in Silicon Valley, who a couple of years ago, told me that he reads a hundred books a year.
He just makes a number and he hits it. And up until then I was reading one a week. And I said, you know, "from now on, I'm going to write a hundred a year." And I just fit it in. I just made it happen. I don't do social media or other things until I've read a hundred pages or whatever it is. And then before COVID, with the nature of the work that I do, I'm flying a quarter of a million miles a year. I could bang out two or three books on a trip. Now it takes a little bit more discipline, but I love it. I am rewarded, I think I see the world differently.
And speaking of books. So you wrote Startup Rising: the Entrepreneurial Revolution Remaking the Middle East. I want to talk about global companies.
Etsy bought Elo7, the Etsy of Brazil. I think a good example would be Uber. They had trouble penetrating the Middle East and they ended up buying Careem. Why do you think that is? And how do you think it relates to this local advantage that companies have?
Yeah. I mean, Uber is an incredibly interesting story.
It's a fantastic company. The CEO is a friend and I think one of the great executives alive today. But you know, in a way, there was something I'll call the "old American playbook." If you and I were having this conversation 10 years ago, maybe a little bit less, the playbook was: if society has a lot of smart device access, American companies show up and they kind of win. I mean with software, they come in. So the Facebook of anywhere, the Instagram of anywhere, the WhatsApp of anywhere were Facebook or Instagram or WhatsApp, because we're not alternatives. And the one-stop shop solution seemed pretty good. And it is what it was.
Well, this has changed dramatically in the last years, because what has happened in this universal access to super computing is that people can get things on their terms – stuff that they understand. Talent is in their backyard. They understand the backyard in ways that Americans or other people flying in can never fully understand.
And I think in many ways Uber in Southeast Asia, even before the Middle East, where they effectively had to pull out and take a stake in Grab – this was a major, major turning point, I think in global technology history. Because it made clear that not only is talent everywhere, but if you understand the needs of the ground, you've got an ability to understand nuances some of times it's very, very simple.
So I'll give you a very clear example of this. I remember Careem, in the Middle East, did a very simple thing. They launched the ability for people to use cash in the app. And for those who know, – and this is true in other rising markets – in the Middle East, there's a long history of people not wanting to use a credit card online, maybe didn't have a credit card.
And so even if you talked about the largest e-commerce player, their most transactions were COD (Cash on Delivery). So this was the tradition. I'll never forget because Mudassir and the team of Careem, who were astounding, said "we're going to lean into this. We know this is what the market wants and needs it."
And by coincidence, I was with some of the top brass of Uber at the same time. And they didn't quite mock it, but they kind of mocked it. They were sorta like "that's playing for the 20th century. We're playing for the 21st century. Everyone's going to just order online and that's the end of it." But lo and behold, someone understood something about the ground, that the ground really, really appreciated.
And you start with something as simple as that, and you take care of sensitivities. Things like Ramadan and other occasions, or how people move money or engage with each other. You then sit on something that outsiders are foolish not to realize that it could be something that would put them back on their heels competitively.
And I think that's the new – we've gone from the old American playbook to what I'll call the new global playbook.
Rising markets. I like how you frame these markets around the world. And tell us a little bit more about how you became this global citizen. I consider myself a global citizen as well.
And you didn't grow up abroad. You grew up in the States, but in the Middle East, Southeast Asia, your name is popping up. I'm involved with Endeavor, so I have this global network because of Endeavor, and it's like, everyone kind of seems to just know you! How did this happen?
And what is your interest of like looking around the world and being part
Well, thank you for saying that. And I'm an enormous fan of what Endeavor has done with entrepreneurs on the ground. I've been very close to them for a decade in any way that I can be. But there's a simple answer to it with a caveat.
And the answer is: I've always been – probably instilled by my parents – a global citizen. I mean, I've been curious about what's happening around the world. I learned at a very young age, just traveling with a tourist lens, that when you're on the ground, things look very, very different than what you see here. And that for whatever attempts there might be in the media and elsewhere to put a lens on what's happening around the world, the ground is very different. The nuance is unbelievable. Individuals think and act differently in very powerful ways. And it was very humbling very early. So I always did that. The companies I ran as an intrapreneur Washingtonpost.com and then ran healthcentral.com, my own group. These were, by nature, global companies. But more importantly, I outsource technology, like many gringos do, to rising markets from Argentina.
But unlike many of the gringos, I actually visited some of my partners. And you see on the ground that you don't know anything, you just don't know anything. And you learn that talent is everywhere, but also market needs are different. And you start looking at folks and you say to yourself, whatever's happened here is going to happen on its own terms elsewhere.
And this is going to be one of the most important things that have happened in global innovation and economy in our lifetime. So it became clear to me, particularly when I began to lead into the Middle East, that if this is happening here, it's happening everywhere. And when the world has smart devices in their pockets, all of us as civilians, as society members, as business people, as innovators, we need to understand what those ramifications are and see how we can help unleash its own potential across the spectrum. The caveat is I admire you and I'm jealous of you. Because what you've done is you went deep. You went into a place and you learned it and became a part of it with tremendous respect and affection.
I tend to be someone who's more of a portfolio of my travels. The good news is I have this interesting pattern recognition that I can bring to bear from multiple locations, but I pay a terrible price in not understanding much in the depth, which is why I just kind of keep my mouth shut. I asked a lot of questions and I get to meet people like you, who helped set me straight as I began to explore this kind of new era that we're in.
I think the pattern recognition is super valuable and we've often thought about how some of the trends happening in Southeast Asia are more relevant to LatAm. How are VCs in the US starting to think about the global opportunities? I'm in a group, a WhatsApp chat, that was started yesterday. Marc Andreessen is in the chat and meeting entrepreneurs from Latin America.
It's like... that seems very different than what I remember when I was begging entrepreneurs to look at the region. So what's the perspective that you think that investors typically didn't look outside of their region or even the US?
In a way, it's a variation on the theme of the old American playbook and the new global playbook.
But now on the venture side, accelerated tremendously by COVID. I think the reality is that even some of the most adamant "I will invest 50 miles from Sandhill road" mentality are looking at how great talent wants to stay home. They're looking at virtualness can work. They know that now there's blue chip investment appearing around the world on the grounds term that you could partner with.
And the time has come to think a little bit differently about it. Now, I think many still are very stubborn about a lot of the opportunity are being here. Others have been taking very interesting toll holds, where they're effectively saying "If we know this entrepreneur, maybe she was in Y Combinator or maybe she was a former entrepreneur in America. Now she's gone home to Mexico. So we know her, we like her and by the way, Brian Requarth, or Kaszek, or someone's investing in them. And it's a space that we understand, let's start understanding it. We can start making some bets in this way." And of course, in the case of Latin America, some of these bets are looking unbelievably lucrative, which makes people start saying things like, well, if it's starting to work in Latin America, how can I take this idea and strategy elsewhere?
My experience has been that a lot of people have been rallying and looking more than deploying. But these things tend to have a hockey stick to them. And so people are showing up in deals that I never thought they would show up in to look at them now. Some of them pull back. Some of them are about to write the checks.
I think a year from now, we're going to see this thing as an entirely different dynamic. Some will probably remain heavily American-focused. Most of them may remain heavily American-focused. But when they understand a set... I mean, if you understand FinTech, you really really know it well, and I've seen the best of the best, and maybe you have some comfort in Latin America or somewhere else.
It's not a huge leap to say," I can take that knowledge with the right entrepreneur and the right co-author on the ground and grab a whole different kind of opportunity going forward." You'd be foolish not to. And I think we're going to look at this year as a tipping point. I think we're going to look at Nubank as a tipping point, particularly in FinTech.
I mean, when Warren Buffett leans in there at a level in a FinTech company outside of the borders of the United States., you know that people are realizing that the world covered in supercomputing and talent everywhere has to be understood in different terms.
Yeah. I remember her texting you that same day, that announcement.
And we're like, it's a game-changer. What do you think are some of the big opportunities in rising markets that maybe privilege or bias won't allow most people to see?
I have strong views on this, which some people counter with. And it's also something I like, which some classic venture capitalists don't like.
I like a lot of these enterprises which are solving very thorny, physical problems and getting it right and using technology to layer on scalability and lower margins and extension of reach. And of course they're beginning to build data, which will allow all sorts of extensions of products overall.
So for example, Americans don't understand that places like Latin America and Africa, anywhere from 50% to 90% of all retail sales, are done in mom and pop shops – who now are beholden to maybe a couple of middlemen or in the case of, for example, Kenya, have to walk two hours every morning to one wholesale market to get some inventory for that day, which if they stock out, they can't get more until the next day.
There's no data involved in this. They don't have basic CRM tools to help manage their business and think about it in a more sophisticated level, they're highly fragmented. All of that is begging for solution that at one level understands the dynamics on the ground that I've described.
But once you use technology, you can do all sorts of amazing things to make that scalable. And then finally, there are entrepreneurs around the world – you see them in Latin America, but they're all over the world – that are sitting on water, becoming massive unique data sets. They understand things that governments don't understand and other traditional players don't understand. They're not getting worked up about credit scoring in a traditional sense, the way the big banks do. They have something better than credit story, which is data and the ability to really understand what people will do. And they understand one other element, which I'm not sure we in America understand quite to the same degree.
And that is the power of social credibility and trust. What I mean by that is you've just got a different kind of influencer in markets who are not necessarily having a million followers on Instagram, so that can have its value. They may have 300 or 400 followers in an SME WhatsApp chat, all of whom think of them as a leader.
And if they start using a service or if they start moving money in a certain way or whatever, and they think that's trustworthy, they will trust it. Or if they start lending money, they don't want to screw the person that they want. They'll pay back that loan. And I think one of the things that's just being unleashed at scale is this deep sense of community and trust, which has always been essential in the physical world. But technology is allowing it to be unleashed in a more scalable way.
The smartest enterprises I know get up in the morning and go to bed at night thinking to crack that in a very different way than the States, frankly, probably in a different way often than even places like China now.
Yeah, that's fascinating. I mean, data does play an important role there. And I think there's a common thread here that we're seeing in this conversation, which is – and this is natural in most other markets outside the US, where there's a trend to tropicalize or copy and paste certain solutions. But the biggest value that's being unleashed is those companies that are solving those local problems, doing it in a thoughtful way that really understands the local intricacies and dynamics. I mentioned your book, Startup Rising, and you focus on the Middle East, but having had experiences in other regions of the world where "Americans won't go", how do you think those observations from your book relate specifically to Latin America?
Two quick observations. I've never loved the term – just to your earlier observation – copycat. It's always used as a pejorative word. There's risk in early days in any market that's rising, but again, the best entrepreneurs didn't merely copy and paste something that happened elsewhere. They understood local nuance, even that in a general experience with e-commerce or whatever, they've understood that nuance. But I agree with you that the ones that are solving really large, thorny problems that are unique to their markets, I think are very powerful.
In the experience that I had in writing Startup Rising – and I thought about this all the time when I was reading your book, and I loved your book because, in a way, it had an element of a tour of the ecosystem. But the tour that you gave was through your experience. It's what you lived and navigated through that encapturing many themes. In many respects, your book and my book, you can almost plug and play it to any rising market with different individuals, different names, and different ecosystem leaders. And there's again, nuance to each of them. But this ability to have success breeds success, to be able to rely on these trust networks, to gather around ecosystem leaders. And usually, they're not that many in a given community who are literally trying to help entrepreneurs be unleashed and to help them to compensate for where there are weaknesses.
And so they can either fix those or they can create their own versions of solutions to them. It's completely familiar territory. As I finished that book, I began to tour elsewhere in the world. I'm like: "Of course there's a massive difference from different places, but so much of it was completely familiar."
And again, in a way, not familiar that we often see in the west. Interestingly, about a year and a half ago, I spent a month in China and what I found among some of the Chinese successful juggernauts, like Ant and Alibaba and whatever, is that they actually understood the language of rising markets because they had just been one.
And so they could understand some of this nuance and would often talk to other entrepreneurs about this nuance, in a way that I still think we in the west don't fully appreciate as much as we need to.
It's totally true. I experienced the same thing when I went to Beijing, Hangzhou and Shanghai several years ago with a group of entrepreneurs from Brazil. And there was definitely an affinity there. So, when I published my book and I had it in print, I remember reading through it a month later. And I'm like, there's already things where I wish I would've said this a little bit differently.
It's like, you never get the book out because you want it to communicate exactly. But at some point you just gotta go with it. If you were to write another edition of Startup Rising today, how would you contradict yourself compared to the first version? What are the things that you realized?
First of all, you're absolutely right. When you write a book that's tech-enabled, it's already overtaken by events of the day it comes out. And the last edition of this book came out I think four years ago. So it's completely mood at many levels. I think that the construct of what is happening. The question of what is going to happen when there are supercomputers in massive numbers of people's pockets and what that can unleash in talent, in innovation and the desire of people who want to make an impact in their societies. It's almost unchangeable. I think the thing that is changeable is that it's happened so much farther and faster and larger than I predicted at the time. In some respects, the book was too timid. The first edition came out in 2013 or 2014. People thought I was crazy to talk about a hopeful scenario in this part of the world.
And there are still many, many problems. There are many difficulties as there are in every part of the world. But when you focus on the bottom-up where we started this conversation, the caliber of talent, the quantity of talent, the problems that they understand the training they've had... the Kareem employees now, who are spinning off and doing their own startups and all, are night and day.
And I'm not sure if I missed it, cause it wasn't there yet, but there's just a whole lot that's happened. That is a dwarf did and has gone off in its own direction.
It's moving fast. Undoubtedly. So one other question I have: I've observed something about you and it's very aligned with the philosophy we have at Latitud, which is to try to really cultivate this give-first mentality. And we met relatively recently, but you've just been so helpful in a lot of ways. And it's probably connected. Maybe I'm answering my own question, but it's probably connected to why a lot of people know you. It's because you have this mentality of creating value for others. Philosophically, there's so much value in creating value for other people and really seems like you practice that.
I mean, there may be some deep-seated explanation that I've never accessed or thought about, someone could dig out of me. But a couple of perhaps obvious observations, I think you and I have shared this in other conversations:
I've never had a success that's not been built on the shoulders of people who took the time, who spent time with me, even if I was down or out, and was willing to believe in me and helped me think through things in a way, very often and very powerfully. Not necessarily tell me what to do, but help unpack the noise in my head to be able to do it.
And it was very profound for me. And I feel that it's always something that I try to do, and I never tell people what to do. I will talk to them, ask questions and, you know, help them unpack it. Secondly, I get a tremendous amount of passion and joy from watching people actualize their individual aspirations to make an impact.
It is something that I've always enjoyed. Selfishly. I learn a lot from it. I take those lessons into other things that I do or I build, or I invest in overall. But I actually just simply just get fired up. In COVID, which was just such a terrible period, obviously in so many ways, and then stopping to travel... you know, Zoom is very efficient, but really soulless.
And yet I think that got me through COVID because every day I was with a dozen people who just had it in their teeth to solve a problem and wanted to figure out a way to do it. Selfishly it was incredibly inspiring and helpful to me. So I think that's an element of it, but overall, honestly, Brian, why are we here?
To make another dollar or to take another chip off the table or to f... why are we here? And I think we're here to kind of make some impact and make some change and contribute our verse. And sometimes you do that individually, which is fantastic, but there's so many people that are doing it, that everyone we touch is an opportunity to be able to do more of that. I just leave it just with a quick note. I remember a couple of years ago there was a Facebook meme or one of social media. I can't remember what it was, where someone was posting: Write when you met me and something you remembered about me. And so I just did it.
I posted it and I expected I'd get five wise-ass friends talking about some foolish thing I did in college or whatever. And I was very struck, Brian, because I got like 200 comments from people I knew, but not that well, each of whom had a very, very, what seemed to me small moment that was hugely impactful on them.
It was a time when I just gave them the time of day when they weren't getting it from someone else, where they were going through a personal thing as a CEO, I helped them with it. Or I simply ask them a question to help clear their head. And two things occurred to me. I don't say that to say I'm a great guy, but two things occurred to me with that.
One is: the small stuff matters and it's so painless to do. And secondly, if that's true, if it's true that those good moments are strong, then the opposite is true. When I ignore somebody, if I don't return their email, if I'm disrespectful to someone, if I'm dismissive to someone I'm actually taking away from that potential.
I'm hardly perfect in this, but I'm deeply committed to it.
I like the revelation there on both sides, the impact that you can create. I'm struggling a little bit these last couple of weeks and months. I really want to get back to everybody and try to help everybody.
How do you scale your impact, Chris? Cause you've clearly done that somehow because your name always comes up. Literally, on my last interview I think I maybe quoted you in one of the podcasts. I said something that referred to you and a random entrepreneur in Mexico was like, "oh yeah, Chris."
And he just picked it up right off where I left off. So like, how are you able to scale that? And how do you get from drowning out with -- I don't think you should prioritize only people that are super relevant because you also never know, and at one point I wasn't relevant. And so there's the underdogs out there that you want to help also.
How have you personally been able to scale that over the years?
The answer is, I don't believe I have it all. And this is an incredible pain for me. I'm not good at saying no, though I am good at once I get to know, it's usually pretty fast and efficient and I keep the door open. But the fact is if I get a random text on LinkedIn or WhatsApp, certainly if someone I respect asks me to talk to somebody, I do it without thinking twice.
And you know, if I get a thoughtful note from someone, whether they want investment or they just simply want to brainstorm a little bit, it's extremely hard for me not to want to do it. And I don't have a great answer to it. I mean, each week I kind of navigate what my coming schedule is.
I leave holes for it and I do have some general areas that I focus on and I try to keep that as kind of my north star. But you and I need to spend more time on this one and help each other because I don't have a great answer to it and I want to figure it out.
Yeah. I've been thinking about the problem more and as we scale our community, like how do we go about doing that? How do you scale advice?
One question I had is about the transition from being an operator to an investor. You mentioned a second ago that you're good at asking questions and you don't tell the entrepreneurs what to do. Was that difficult being in the operator's seat? You understand the inner workings of how to run a business.
And now you're in this other role where it's like, you've got to give the space to the entrepreneur. Do you ever feel like "I just want to give them the answer" or is that something that you've learned, being more Socratic with how you work with entrepreneurs?
Part of it is that the people who were most effective helping me were the ones who didn't try to tell me what to do and had that engagement.
Also, I've been angel investing and mentoring young people for a long time. So it wasn't like it was a complete pivot, but I must say, when I really was out of my last company and began to do this more proactively, there are times -- maybe I don't want to tell them what to do, but I'm sort of chomping at the bit to trade places with them.
There are times with certain entrepreneurs, I think to myself "why I wish I was doing that, that's just awesome." And then there are other times when I get a phone call at 2am and when we're over, I can say "I get to go to bed, but you do not."
And that's kind of humbling, but one of the things... There's a great historian named Robert Cero, who wrote these amazing books about Lyndon Johnson and another huge figure in New York called Robert Moses. He's one of the great interviewers in that profession that I've ever had experience with. And there's something that he does when he goes to interview people.
There are so many things he wants to say, and so many analogies he wants to make and whatsoever, but he opens up his pad or whatever uses the interview and he writes SU at the top of it. And that stands for "shut up." And so there are times when I write SU before I'm meeting with someone so I know that I got to shut up, I really got to listen. I got to pause and not make it about me and not talk about what I would do in your shoes or to, you know, do at it. And my batting average is probably better now than the first year after I sold the company, but it's still not perfect.
Are you kind of a history buff? I feel like you draw a lot of connections with history. Is that something that you've... when you go into these deep readings, is that a part of what you read? A lot of times we've had conversations and I just hear you piece together some historical event and you seamlessly thread it with current reality. What's up with that?
Well, I mean, I do love it, and I was a history major, you know, as a kid and all. Churchill used to say that in all the lessons of statecraft, you must study history, with always a risk that if you study too much history or if you feel too tied to it, you miss obviously all the things which are different. But it's no different. You've been an athlete, I've been an athlete. I mean, at the end of the day, you learn from the bad games, you learn from the mistakes you make in a play. And it's no different with history.
I find that particularly in all the traveling I do. Making the effort to get some of the context in what's going on in Singapore, Indonesia, or Brazil or wherever I go. And to have the respect of trying to get at least some of that context is very helpful.
I think people on the ground appreciate that you have a sensitivity of where they've been and what is happening. And you have a little bit of a language of where forces may be pressing people in the decisions that they make. Again, I think the risk is that you can become too blue to it.
And the old, famous cliche that history doesn't repeat itself sometimes it rhymes, is probably about right. But I have found it highly instructive in a way to kind of step back and reflect contextually. And the best thing about history at all, particularly in biography is: I don't believe human nature has changed that much in the last 2000 years.
And there are certainly things that you can read about in terms of leadership and leaders or how people have allowed themselves to be trapped by their own hubris to make mistakes. That was instructive to me when I've been in bigger companies, as it was when I had 10 people under my watch. And so a lot of that is very concretely valuable in and of itself.
You've got a lot of experience and you obviously worked with people that helped you. Because you've got this same thought process of helping other people. Who are the people that had influence on you and what were the biggest lessons that you took away from those relationships?
Most of the people that have helped me certainly in the younger part of my career are people that you would not necessarily know, but were touched in my life and took a real interest in me in that kind of way. Now, it's interesting, cause I'm of the age now where I'm sort of becoming a wise man of some sorts, my mentors, the people I rely on are my age or younger very often.
And they're just folks that are... you know, every time I'm with you, Brian, I learn something. I look at the world differently, not just Latin America, just for spending time with you. And so in many ways that's the kind of thing and I'm just blessed by having some people. Some of them are well known. Some of they're not very well known – who, when I spend time with them and I ask them questions where they share their experiences, we brainstorm.
It's very powerful, but I must say that probably throughout my life it's been the example. It's almost like Ben Horowitz's book again, it's almost the example as much as the words of the deeds.
So I had this one boss that again, that nobody will know, as a kid. I worked right out of school to pay off student loans and just get a bit of a grounding in business, being a history major. I worked for 18 months in investment banking and it was one of those a hundred-hour weeks. I was proud to work three nights without sleep and everything else. And I did a very big proposal for a group for a huge piece of business, and I kind of led it and I did it and I went three days without sleep.
And I've never been more proud. And when they came back from the meeting, the head boss called me in the office. I assumed to give me a bonus and give me all sorts of kudos. And he looked at me and he said: "Chris, you're a great professional and you care. But sometimes you move too quickly and you're probably not getting enough sleep, and you got to watch it because you made a mistake." And then I defended myself. There's no way I made a mistake and everything else.
He proceeded to show me one piece of paper. The minute I looked at it, I realized I not only made a mistake, I've made a finance 101 mistake. It couldn't have been more basic or more stupid. It made it seem like I didn't know the difference between a balance sheet and income statement.
I was completely crestfallen because I had this blue-chip team going to a blue-chip company with stupid work. Now that boss frankly, could have fired me on the spot. He certainly could have reamed me out. And he got it, he looked at the expression on my face and he said, "We're here to learn. And together we'll learn. This is a bad mistake. I have no doubt you'll never ever make it again. And you ought to see what the lessons are, and we'll talk more about them going forward. But I want you to know I believe in you, but you know, this is going to be a big moment for you if you allow it to be so."
I mean, that had a 50 times multiplier effect on who I was, what kind of boss I became, how I thought about the work that I did, than almost anything that someone sort of showed me or told me to do or something that I read in a book.
Those are formative moments, right. In a young person's career. And it's easy to get upset, but it takes energy to help the person evolve and it clearly left an impression on you.
What advice do you have for young entrepreneurs, budding entrepreneurs that are trying to surround themselves with people that have more experience that can guide them? You know, I was fortunate to have a handful of mentors over the years, but what advice do you have about someone seeking out mentorship?
I think there's two elements to it, in my experience in things that I've seen or also what I'm receptive to when I get to meet people in this way. And one is maybe an overarching theme: it's a sense of humility. I mean, are you really willing to map and understand and look at yourself in the mirror?
What is it that you really don't know? Where are you weak? Where are the questions that you have? What are things that your company is missing? What might be happening in the ecosystem that might be missing? But to really be concrete and humble and direct in what it is that you need. And therefore, when you invite someone to become part of your life, you're aiming at them, you're being useful to their time.
You're also being clear about the kind of needs that you've had. You know, your friend David at Nubank, I've heard told many times that he's just been exceptional and sort of saying, "here's what I've got. And here's what I know I don't got." And by 'got', I'm going to find the people that I can get around me, that I could really learn and listen, ask questions and move forward. Then it goes to the second element beyond humility, which is a sense of reciprocity because at the end of the day, I learned as much from that entrepreneur and that spirit as she's going to learn from me. And yet we both learned tremendous amounts together and I have infinite time for you.
And so when I meet people in good conscience who: have a very clear idea of what they are, they've got tenacity and energy, you can slow them down, but you can't stop them. They have some audacity, they may even have some hubris, but at the same time, they have this humility to know what they don't know or ask the questions to help get them there – I'll do everything I can to help them. And I know that over time it will become a friendship where we're both teaching each other and helping each other.
Yeah, I think that's really well described. I look at kind of the moments where I was able to benefit from a relationship, from someone else, that helped me. Those moments where I really acknowledge that I needed help.
And in the moments where I got in situations where maybe I was arrogant or something, usually that stems from insecurity. I think that when someone really truly has that kind of balance of humility and hubris, somewhere in the middle. That's a good place to be, because you've got the confidence of what you're doing and the conviction about what you're doing, but at the same time you realize that it takes a village.
Speaking of village, I've got Ben [Casnocha] coming up pretty soon on the podcast. And you're part of that network as well. I'm excited to have Ben on because you have to have humility to be inspired by other people. I look at a lot of what we're doing at Latitud. Some of the inspiration is a mix of YC, a mix of angel list, village global, on deck.
If you don't have the humility to be like, "listen, I want to learn from other people", it's a dramatic limitation on what you can do. I'm curious as to how some of these relationships have formed and you've become a resource for investors globally. Because many investors, as you said before, they're not comfortable looking at these other markets. The markets "where Americans won't go." How do you serve as a resource for those entrepreneurs, those investors that are looking in those other places? And how do you think we can decentralize more and have more spread out support networks across the, not just Latin America, but the world.
It's interesting. And this ties to something that we were just talking about before, because people talk about this kind of social engagement and this idea of being both humble, but at the same time, audacious. Humble in knowing that there are things that you do not know, and they will bite you. But audacious in being undaunted by them and going after them.
Sometimes people think this is something soft or fuzzy. Elon did a tweet, not long ago. He said – and I can't remember exactly what he said, but effectively, he said – "if you need someone around you, then you're not a great entrepreneur" or whatever. It's just ridiculous. But it does have an element of toughness to it.
And the thing which is powerful in the people who have been most helpful to me, and I, and others – and I think Village Global and you are a perfect example – is that tough love is a part of this calculus. I mean, what someone is seeking for is also blunt honesty. You may not tell them what to do, but you may tell them where they're bullshitting you.
That kind of sense that this is not a game that we're playing, but this is something that's highly demanding with a tradable amount of pressure on you. But at the same time, you got to look at those hearts. I think it is a really powerful element of it. Sometimes we can have conversations like this and you can think, "well, a great network means a great fun and social thing."
It's wonderful when that's an element of it, but there are also a lot of hard truths that are elements of it, of people who've been there who are sharing those experiences. And one of the reasons I consider Ben one of my closest friends, and I've loved Dan for many years, and Eric, and some of the other people on Village Global is that there's this mix of respectfulness and thoughtfulness.
But they are no-nonsense. They know what is true and what's not true. They may present it in a questioning way or whatever way, but it's complete clarity on how they think, how they have an expectation of people around them. And therefore by definition, they surround themselves with now hundreds, if not a thousand, members of their network – all of whom are very accomplished and very smart and very no-nonsense. And there are total honesty and total integrity, but they know part of integrity means discipline and strength and directness. And that's one of the things that I admire so much about what you were building in Latitud and with the best examples of what I'll call, for lack of a better term, ecosystem enablers,really bring to the team.
The tough love is super important when you've got the trust layer. And you've got the trust layer. If you don't have the trust layer... I've talked about this on the podcast before, but there's this framework for cohesive teams where you've got the base layer of trust. If you have trust, you can have conflict. If you have conflict, you have commitment.
Once you have commitment, you can have accountability. And then ultimately, you get results at the top of the pyramid. And that tough love... I think about the moments in my journey where some of the hard conversations that happened, I knew the person cared about me.
That's just so important because when you understand that the person has your best interest at heart, you can be more receptive also in taking that tough love. What's some tough love that you've given or received at some point? You don't have to tell the exact situation where the person is. That kind of changed the course of either where that person went or where you went?
Well, I think the example I gave you from my own personal experience was plenty of tough love.
He was gracious as can be. But it was very, very crystal clear. He was actually an old Naval officer and it was very clear every element of his dynamic. Frankly, his disappointment, but also his encouragement. I've had many of those over the years, many of them. But I'll tell you, I really pretty much never raised my voice at a business professional.
My kids may disagree from some occasions when they were little, but that's never constructive. But when, on the rare occasion I have, – and most often than not, they're actually pre-planned – they actually send a signal. They send a signal that "I got to pay double attention to what Chris is saying. And I'd have to really reflect on it and it almost snaps to get attention, to make sure that everybody's hearing each other overall.
And I've had to deliver some very, very tough messages to entrepreneurs. I usually put velvet on the hammer. But I can think of a couple of occasions where I didn't yell at them, but I sort of laid down the law in no uncertain ways that were different than my normal style. And it caught their attention. Frankly, it was almost a tool of focus, which we're still... the one instance I'm thinking about right now, I couldn't have more affection for him and would invest in him tomorrow, almost sight unseen. And I think he feels the same way, but that was a dynamic that I think was helpful to him.
It reminds me of– I have a mentor, Greg Waldorf, who was an early investor.
He had a very calm temperament all the time. So when his voice rises just a little bit, all of a sudden you're paying attention. You know that there's something serious there. But at the end of the day, it's about caring for the person and then giving them that support and sometimes they need the love. Sometimes they need a little feedback or whatever it is.
Chris, this has been super enjoyable. I gotta say, I've really sincerely enjoyed the relationship that we've built in a short amount of time. And also I'm just impressed with the crispness of your communication.
Every time we talk, it doesn't have to be a long conversation, it's packed with dense topics in a very clear format. In fact, whenever I have conversations with someone where I'm like, "I wish other people could hear that conversation" – that's when I'm like, "I have to invite them on the podcast."
So this is an example of that and I think I've got a lot to learn from you. We didn't get into much about your investing, what you're spending your time and energy on. Would love to continue to build on our relationship.
I think what's great is in this conversation, we kind of touched on many of the themes that of course affect the way that I invest in. I certainly am opportunistic in my angel, like every angel investor. If I can go side by side with a great opportunity, almost anywhere in the States, I look at it. But really 80% of my life is answering the question of what is happening to these amazing markets, in emerging markets – and what they share and what they learn and what is being unleashed.
Brian, when you reduce it, in the most reductionist, this unleashing of technology, this unleashing of innovation, it's effectively nearly 3 billion new customers who have appeared in the last five years. And they themselves are bettering their businesses, or getting credit for the first time, or building their own companies and this sort of amazing flywheel.
And so I just love being in hubs. I think of them as hubs. Singapore for Southeast Asia, Brazil, São Paulo, Mexico city for Latin America, Dubai for the middle east and Nairobi and maybe Lagos in Africa. And I just love to find great entrepreneurs who are taking deep thorny problems, understanding what is the local edge and are layering on technology in powerful ways. I love a lot of B2B solutions. I love FinTech, particularly, as it's facilitating credit to small businesses, because that's exactly what's needed in these markets. I love these, uh, B2B marketplaces.
These are things I just love and they're going to be longer slogs. But they are affecting literally billions of new customers. And I think they'll be a whole new generation of very successful enterprises.
Just for those founders that are listening: when you're coming in, and you come in early? Check size, co-investing, leading... give us the quick rundown on your investment thesis there.
It's typically been pretty early. Sort of in the quarter of a million to a million seed or pre-seed, and participating in A. But one of the blessings I have is in the relationships that I have, and I've been putting together SPVs in the A round and other things quite easily. And with some very good people. I actually will piece together folks who I think have a real expertise in whatever it is that the woman is trying to solve in her company.
And I can put together a quick partnership that could be helpful to that as well. So I don't think I'm gonna be doing series D anytime soon, but I have some pretty good – to use your word – latitude in how I think about things in that way. But the sweet spot is a $500k to $2 million-size.
Well, if I was an entrepreneur looking for some money, I think that you would be that someone I'd want on my team, given your experience, philosophy and value adds. So hopefully we can do some deals together here shortly.
There's no question we will.
And it's great to have you as part of our network.
Well, it's an honor to be with you and I can't congratulate you enough on all that you've done, but more importantly, what you're laying out for the impact of the future. I think Latin America will look different and I think your model will be taken elsewhere because of what you've done and what you're accomplishing now. So thanks for giving me the time.
Thank you, man. Super enjoyable.
Thank you so much.