The journey of an entrepreneur is lonely, especially if you’re looking to start a business in Latin America, where opportunities are ripe, but resources are scarce. In his new book, Viva the Entrepreneur, Brian Requarth aims to help demystify the obstacles you’ll face, teach what you won’t learn in business school, and offer you inspiration and encouragement on your journey.

His lessons will show you how to manage your own psychology and your operations, be it working with co-founders, building a culture, or managing a board of directors, and also reveal the secrets of scaling a business in Latin America. You’ll develop an understanding of the most critical parts of an investor term sheet and gain perspective into the inner workings of the venture capital game.

Drew Appelbaum: Hey listeners, my name is Drew Applebaum and I’m excited to be here today with Brian Requarth, author of Viva the Entrepreneur: Founding, Scaling, and Raising Venture Capital in Latin America. Brian, thank you for joining, welcome to The Author Hour Podcast.

Brian Requarth: Hey Drew, thanks for having me on.

Drew Appelbaum: Let’s kick this off, can you give us a rundown of your professional background?

Brian Requarth: Sure, I’m originally from the Bay Area, in Northern California and I went to school in San Diego. Right after school, I didn’t actually study business. I studied Spanish literature which, didn’t really make a whole lot of sense to anyone at the time. People thought I’d maybe become an English teacher or a Spanish teacher.

I ended up getting in my car, drove from California to Costa Rica, bought a one-way ticket to Columbia–there’s usually a woman behind these stories–I met my wife in San Diego. She likes to say she imported me to Columbia. I landed in Columbia at 23 years old, and I in fact did teach English, not Spanish, being in Columbia. That was the start of my entrepreneurial journey.

But I’ve never had a real job. I have basically been building companies since then and that was 17 years ago.

Drew Appelbaum: Now, why was now the time to write this book? Did you have an inspirational moment, did you have an “aha moment” or did you simply have a lot of time on your hands due to the current crisis?

Brian Requarth: I ended up selling my company a few months ago and the company was winding down. We’d been in a transaction for quite some time and so, it was being reviewed by regulatory bodies in Brazil. I had some time, and it was a transition time for me.

I always wanted to share what I’d learned along the way and wish I had a book like this when I started because I made so many mistakes as an entrepreneur. I realized there wasn’t something tailored to the experience of building a company in Latin America, and so that was the inspiration and the motivation for writing the book–to pass along the lessons.

Drew Appelbaum: Now, while you were writing this book, maybe by looking back at your journey or sometimes just through the writing process, you’ll have some learnings or major breakthroughs, did anything like that happen for you?

Brian Requarth: Yeah, absolutely. As I wrote the book, I spoke with many entrepreneurs and listened to the pain points that they had and their experiences. There’s a shared connection as an entrepreneur that is in the struggle, building the business, and following their dream.

I think that the realization I had was that there’s a lot of these examples and stories that need to get out for us to elevate the next generation of startups and companies, to build iconic companies in the region. I think the big realization was that I wasn’t alone in my battle and my journey. I think that I wrote the book because I really empathize with the difficulties of building a  company.

I wanted to share the lessons, but I also wanted to write something that people would feel inspired by and connected to, that they could pick up–sometimes your best day and your worst day is the same day–they would be able to pick up the book and find some solace in knowing that we were successful in our journey, but it wasn’t a straight line.

It was filled with all kinds of ups and downs and twists and turns. That was the realization I had–the importance of sharing that story to provide comfort.

Also, I read a few books that resonated with me during my journey but there was never a book that was really tailored to Latin America. So, I wanted to tell that story so entrepreneurs would have an example that was more local and connected to their experience.

Drew Appelbaum: Right, when you are writing the book, in your mind, who are you writing it for? Could it translate to other markets? Can you take lessons away from the book and use them in the United States market, is it for somebody who hasn’t started their entrepreneurial journey yet, or is it somebody who is already a few steps in?

Brian Requarth: Yeah, absolutely, I think that a lot of the same challenges exist. In the book, I talk a lot about psychology and managing your own psychology as you build your startup, which is relevant for everybody. It’s hard, you’ve got a lot of things to balance, you’ve got a personal life to manage, you’ve got the dynamics of the co-founder relationship.

Those are all things that are highly relevant for any startup, regardless of where they’re located, and we also talked about some of the things such as hiring a team and how to bring on advisors and mentors and investors and those are all things that I think are highly relevant.

However, the examples I gave were obviously more tailored to the experience, whether you’re in Mexico, Columbia, Brazil and, there are obviously portions of the book that are a little bit more adapted to the reality that we live with in Latin America.

Unique to Latin America

Drew Appelbaum: What does this book bring that other books on the subject do not?

Brian Requarth: There aren’t really any books that are written specifically tailored to this part of the world–Latin America. The intricacies of how things are done in Latin America, the experience of what it’s like building a company in Latin America, it’s a pretty unique book from that standpoint.

There haven’t been as many success stories in the region, it’s still early and nascent in the life of entrepreneurship. It has been around forever obviously, but the whole venture capital ecosystem is at an early stage in the region and I wanted to shed light on what that’s like in Latin America. So, it is a unique book in that sense because there aren’t really any books like it.

If you go on Amazon and you search for books around startups and venture capital, you’re going to find a lot but you’re not going to find any that talk about the challenges and the opportunities in Latin America and it is a region with over 700 million people.

There’s a lot talked about in the US or in Europe but there’s not a lot of things that are tailored to this experience.

Drew Appelbaum: If you could narrow it down to just a few bullet points, because I’m sure there’s a lot out there, what is the major difference between starting a business in Latin America and starting a business in the United States?

Brian Requarth: You know, there are two parts to it, the first one is, obviously, being in Latin America, it comes with a lot of bureaucracy and a lot of challenges. But that actually presents an amazing opportunity because there are friction points on your journey, whether you’re buying a car, whether you’re buying a house. Those things actually operate in a lot more efficient manner in the US or in Europe.

This book really highlights some of the opportunities, some of the challenges in raising capital in the region. As an example, I ended up building a company that was a Delaware C-corp, which is the standard thing for a venture-backed company in the US. The reason why I did that is that that was the general wisdom that most US investors understood and that resulted in us losing a hundred million dollars in value because we didn’t have the right company structure.

That’s just an example of one small detail but that had a huge impact. So, I cover things about the right structure to have for a venture-backed company–that’s an example. Then also, how to manage the ecosystem, how to bring on the right investors, and what investors think about and look at. So, those are all examples of things that are covered in the book that I think are unique to the region, and important to go in with eyes wide open.

Building a Team

Drew Appelbaum: Now, a lot of authors feel the need to write the book, because they want to impart some knowledge but also because that knowledge came from making mistakes in the past. Can you share one mistake that’s top of mind that you’ve made and tell us what the lesson learned was and how it guided your journey moving forward?

Brian Requarth: I just mentioned a pretty big one, skimping on legal and accounting was definitely a pretty big mistake because it ended up having a price tag of a hundred million dollars.

What comes to mind is not understanding the dynamics of how venture capital works and understanding the psychology of the investor. One example that I can give is that when I went out to raise money, I randomly would contact any investor. I didn’t do the research to properly understand, “Is this the right investor for my business? Is it the right stage or sector? What have they invested in that indicates they might be interested in my opportunity?” I think that really just like building a framework for how to think about capital raising is something that, I made some very rookie mistakes on my journey there.

Team building also–I remember in the early days, as we started our company, I ended up hiring an executive who was flashy, who had an amazing brand associated with them, and worked at a successful big company. But it really wasn’t the right fit for the early-stage challenges that we needed.

On day two, it was, “I need to build the team because I’m not actually operational or I don’t execute, I have a team.” That was a mistake is that often, founders are drawn into thinking, “Oh, I can bring this person on board because they have all these experiences.” When in reality, you have to make sure that you’re hiring someone that can get the job done that you need today, not in two years.

Drew Appelbaum: Now, let’s dig into the actual part of being an entrepreneur. Right from the beginning, what kind of person does it take to be an entrepreneur?

Brian Requarth: I think that you have to be motivated to solve a really big problem. You have to have unparalleled persistence and perseverance. The hustle and scrappiness are just essential because so many things aren’t going to go your way and you’re going to need to adapt and overcome as you’re on your journey.

I’d say that the single most important quality of an entrepreneur is the willingness and desire and determination to figure it out. You need to go after a big problem. This book is really tailored to those that want to build venture-backed companies.

There’s plenty of different forms of entrepreneurship. If you’ve got a bakery in your hometown, you’re an entrepreneur. But this book is a different type of book, this book is written for those that want to build businesses on a massive scale that transform industries and sectors. Latin America’s full of opportunities for just that.

Drew Appelbaum: Would you encourage this life on others? Or is it simply too hectic?

Brian Requarth: You know, I don’t think I’d trade being an entrepreneur for anything. I’m filled with energy as I figure out challenges and overcome what seem to be really hard obstacles in my way.

The driving force for doing it, it’s not the exit, it’s not the money. It’s the motivation to go tackle something and make a difference and see your idea come to fruition and change how things work. If that lines up with your MO, your modus operandi, and how you see the world, then you’re probably possessed to be an entrepreneur. In my case, I’ll always be an entrepreneur and I’ll always be building businesses. I feel like it’s my DNA.

But if you’re on the fence about it, if you find yourself highly motivated to solve a specific problem, I wouldn’t become an entrepreneur just to become an entrepreneur. I would be centered around solving a really critical problem that you just can’t stop thinking about.

Solving a Problem

Drew Appelbaum: Can you talk about the sacrifices that an entrepreneur has to make? Specifically, during the early journey.

Brian Requarth: Yeah, well, in my case, I didn’t have access to capital, I didn’t really know a lot of people, I didn’t go to a top business school that had a network attached to it. Early sacrifices–my wife and I slept on the couch of my co-founder’s apartment–in his little one-bedroom apartment, we slept in the living room.

I remember, thinking twice in the early days about spending $4 on coffee because things are tight. There’s definitely a sacrifice involved–you might be looking around and seeing your friends making a lot more money than you at that time because it requires a lot of time to ramp up.

It’s obviously something that requires a lot of fortitude and focus and desire to make it happen and it definitely comes with sacrifice but in my view, it’s all about the journey and the journey is definitely worth the price that you might have to pay.

In the grand scheme of things, they are usually small sacrifices. Of course, some people are in different positions where financially, maybe they have a bit more privilege and they can afford to do it. There are different levels of sacrifice for different people and that’s something that needs to be noted.

But at the end of the day, when you’re determined and you’re driven to solve a problem, the sacrifices seem small in retrospect.

Drew Appelbaum: You mentioned the journey of an entrepreneur and in the early days, you’re sacrificing a lot, including even a daily coffee. Eventually, you have more hurdles along the way and if you pass that first phase, you get to a spot where you’re bringing on higher-level employees, senior leaders, and creating high-level partnerships.

Can you talk about what you looked for in those higher-level partnerships and maybe a little bit about the relationship that you had with your co-founder?

Brian Requarth: Yeah, absolutely. Starting with the co-founder dynamic at the base, it’s just so critical to have amazing communication and that’s something that you build over time. When you start working with someone, you’re figuring each other out, you’re figuring out what their strengths are, what’s important to them, what their values are.

Obviously, the values or I call them virtues in the book, ideally line up and you’ve got a shared vision about the type of business that you want to build. But really, it’s just about investing in that relationship and laying the right groundwork to make sure that your motivations are aligned with why you’re building the business. I think that is something really critical. Co-founder disputes are one of the biggest startup killers because maybe one founder wants to sell the company and maybe one founder is building it for the wrong motivation or motivation that doesn’t align with your motivation. I think that investing in the early discovery and being really candid and authentic with why you’re building the business and making sure there’s alignment there from day one is super important.

Regarding the early team, what I think is the number one priority is to find people that have the motivations and that buy into the vision of what you’re building. It is really about their motivation and their desire to achieve what you’re setting out to do as a company, regardless of how smart or how amazing they might be, if they’re not hungry to go after what you’re setting out to do as an entrepreneur, you are not going to have the right DNA as a company. Remember, all of those early people that join your effort to tackle this big idea, become multipliers for everyone else that comes on.

It’s really the base layer and the foundation for people to come because, after the first 30, 40 hires those people are setting the tone. So, if you get that wrong in the beginning, you’re setting yourself up for a bit of a challenge because fixing culture is quite a challenging thing to do when you’re larger.

We would be very candid with the first hires we made. We would let people know, “This is not going to be the easiest job you’ve ever had.” Almost to the point that if they still wanted to work with us, they were really, really bought into the vision and what we were trying to build.

Drew Appelbaum: Now, you talk about the vision, you talk about culture and values and you talked about, it might be easier sometimes to find the philosophy of choosing the values for your company by saying what you’re not going to do in your business rather than what you want your values to be. Can you talk about that strategy and what it looks like?

Brian Requarth: Well, I think that in terms of focus for the business, there is a challenge as you build your business. Entrepreneurs naturally want to chase a lot of bright and shiny lights. There are so many opportunities, your mind is racing on a hundred different things that you could be building, but as an entrepreneur, you need to have very strong discipline That’s what a lot of people talk about product-market fit, and to focus on those key things that are going to really drive value for your business.

I see a lot of companies that scale too early or build a large team in the beginning when they really haven’t figured out what they actually are supposed to be building and what the real opportunity is. I think that is something that happens oftentimes with that key team at the beginning of six to eight people, that’s really working hard to figure out what it is that’s going to build value in the company.

Whether it is what customers are communicating that they want and starting to buy, or you are starting to see that early traction. I think that is something that is really important, and you have to strike the balance of being able to test those things–that once you figure it out, that you nail it before you scale it. Those are the things that you’re going to need to really home in on in the early days.

I think that the culture of that is really hard when you’ve built a larger team. An early-stage company is constantly pivoting, it is constantly changing until you find that product-market fit. So, you don’t want to have people that are uncomfortable with uncertainty. That’s why people typically that come from a larger company don’t adapt well to the whiplash that exists when you’re in the early days, trying to figure out exactly what the business is and what it’s going to become. So, I think that is a really critical point is to make sure people align well with that. The right type of people that can handle that uncertainty in the early days.

Drew Appelbaum: I think what’s really interesting about your story is that you start from the beginning of starting your own company and again, all the hurdles and the successes and some failures along the way. Then you switch gears and you are actually the investor now and you’re a VC, you invest in companies in Lat-Am. Can you talk about when you were an entrepreneur, what you were looking for with investors and now as someone who invests, what you look for in companies?

Brian Requarth: I guess I can qualify as a VC today even though I am more of just an angel that likes to help entrepreneurs. This all organically started mainly because in Latin America, it is a small community of people that are reinvesting in the ecosystem. Where in the US, you’ve got a lot of entrepreneurs that have sold their companies and then are reinvesting in the next generation.

You know, people refer to the PayPal Mafia as an example of that. Really, this just organically started because as an entrepreneur, I was building Viva Real and I had some success at raising capital. Then I would have friends that would reach out and say, “Hey, how did you do that? How did you raise the money? Who is the best investor I should be talking to? Who is a good fit for what I’m building?”

I would end up making intros or giving advice and I ended up accidentally becoming an investor–there is the classic saying if you ask for advice, and you might get some money, or you ask for some money, you might get some advice. So, I ended up investing in some of those companies when they would ask for my help because I would learn more about the business. Me becoming an investor was very accidental and it happened naturally.

So, answering your question about what I look for now. I still want to build companies, and I’m currently building something right now and still trying to figure out what it’s going to become. But I am very focused on early-stage entrepreneurs and that challenging moment of ideation, to your first customers.

So, what I really look for–I guess a good analogy is the fishing analogy. If you’re fishing, you want to go where there’s lots of fish, so that’s like a large market. A big lake with a density of fish is a good place to be fishing. You want to look at who is fishing, so is this team really, really experienced, have they been through different experiences before that would give them some unique insight into the problem they’re solving? You might want to look at who is fishing next to them, which maybe isn’t quite as important as the market size and market opportunity and the team.

I’d say team is probably the number one thing in the early days. I’ve invested in a handful of companies that maybe haven’t even figured out what they’re building yet but the team is so stellar. They just have this look in their eye that shows that they’re determined to figure something out and make it happen.

Those are the primary things that I look for as an angel investor. I shun the idea of calling myself a VC because I’m a founder at heart. But ultimately, as I invest in more companies in the region, right now it’s just my own capital but, we plan on raising some additional capital from other entrepreneurs to help build the next generation of iconic companies in the region. Those are the main things that I look at–team and then market opportunity.

Make It Happen

Drew Appelbaum: Now, is there anything though, in particular, that a business owner can say that will catch your ear? What’s the one thing you’re looking for when they say, “Our business is doing this,” that will just say, “Here’s the checkbook.”

Brian Requarth: Yeah, some investors only invest at companies that have very predictable revenue, or those that are referred to more as later-stage investors. I go so early that oftentimes, sometimes it’s just a PowerPoint presentation. That’s a fun place to be in because you’re essentially just betting on talent and betting on people.

I think that the things that I look for in individuals and of course, I do invest in companies that have revenue and growth. I think the thing that I would look for and if I look back at the investments I’ve recently made, what are the things that would be a turn on, so to speak, for me? It’s those founders that can’t really keep up with the demand for their products. That is obviously a very strong sign when you’re just so overwhelmed with the demand for what you’re building. You need to accelerate from a standpoint of maybe hiring more engineers to double down on the product.

I invested in a company, which is building the bank for under-banked and un-banked women globally, starting in Latin America. When I talked to Emma, the founder and CEO, she had 70,000 women on her waitlist to join her as she built this bank, and she didn’t even have a product yet.

That to me was like, ding-ding. One, I love the financial inclusion aspect of it and the mission. You could just see in her eyes that she’s going to solve this problem and she’s going to make it happen. That is an anecdote of something that I think would illustrate what you were asking about. Literally, on the first call, I was like, “I’m in.” It was a 45-minute conversation, and I asked her for wiring instructions at the end. That to me is an example of something that just made me move.

Drew Appelbaum: That’s a dream for a founder right there. Now, what I really like about your book is that you talk about your journey and you talk about that you’ve had a lot of success, but you are not pushing it. You really go a little existential and you ask the readers to ask themselves a few questions to find their reason for being, and they have to ask themselves what do they love, what are they good at, what does the world need from you, and realistically, what can you get paid for?

How did you come to these questions and are they just a luxury? Can you really be successful and go through life by answering these questions and moving on the answers?

Brian Requarth: It’s a good question. First of all, it’s the framework that I use. Maybe I’m in a position where I can sit back and take the time to do that. I understand that it is not realistic for everybody and that’s okay. If you are going after something just because you think it’s an amazing opportunity and you want to build a business and that’s your motivation, I think that can work and that’s fine.

Maybe it is a bit idealistic the way I’m thinking about it. But it is true to me and true to the moment that I am going through right now as I think about my next decade of what I want to sink my teeth into. I do sincerely believe that if you find the balance of those things that you love and what the world needs and what you can get paid for and what you’re good at–and you can actually string those all together into what you’re building, I do think that your impact will be greater.

Because, as you face your first obstacle and it’s going to be hard no matter what, but if you really, really are doing what you love, for example, then you are definitely going to figure out, you are going to find a way. I don’t think it’s a criteria that’s necessary for every founder.

You know, the other day I talked to a founder who is building the infrastructure layer for Internet access in Latin America, bringing the cost of access down to under two dollars for people that don’t have unlimited Internet access, and that’s hundreds of millions of people. The person happens to have an amazing skill set that allows them to do that. I think it’s a huge opportunity because it’s an enormous market and so that founder happened to do that.

I think that the companies that are going to be transformative on the scale of really changing society, I think that they’ll have those things. Now, not every company that I invest in is going to transform society and leave an indelible mark upon a country for a century. That’s obviously the dream when you are looking for opportunities. You want to find more companies like that, and I think the best companies fit that category, but it doesn’t have to be a requirement for me to be involved.

Drew Appelbaum: That makes sense but Brian, writing a book and one like this one, which is super thorough, we really just touched on the surface here today, it is going to help so many business professionals, and writing a book like this is no small feat. I want to say congratulations on publishing your book.

Brian Requarth: Thank you, it was quite the process and I was happy to partner with Scribe in that process, which was great support for me, and it was quite the learning experience to try to put everything down into a condensed version of how I see the world and the opportunity in the region.

Drew Appelbaum: I do have one last hot seat question for you, so I pre-apologize but if you had to narrow it down and if readers could take only one thing away from the book, what would you want it to be?

Brian Requarth: My objective for the book is a couple of things. One, I really want to help entrepreneurs navigate the challenges, the perils, the opportunities of this journey of building a company. So, I hope the one takeaway is that it becomes a little less lonely for you by at least learning from the lessons that I lived over the last decade in the region.

Connected to that, this region of the world is not top of mind for many people. But with an enormous population, an enormous amount of concentrated talent, many world-class companies are going to come out from this region. So, I think that those entrepreneurs that are at the early stages, that hopefully, will think a little bit bigger about what they’re building, not just think about their city or their country but think a little bit more on a global scale.

I hope that that is something that founder’s takeaway when they read this book and they’re on that journey that maybe they think a little bit bigger. You know, it costs the same to dream small and dream big as one entrepreneur, Jorge Paulo Lemann, says in Brazil, so you might as well dream big. So, I hope that is the result of this book.

Drew Appelbaum: Brian, it’s been a pleasure and I’m excited for people to check out the book. Everyone, the book is called, Viva the Entrepreneur, and you can find it on Amazon. Brian, besides checking out the book, where can people connect with you?

Brian Requarth: Sure, I’m probably most accessible on Twitter so find me on Twitter. It’s just my name, Brian Requarth, that’s my handle and you can also reach me on LinkedIn, which is a little bit harder to probably connect there because it is not quite as direct. Then also, please go to, and there you can learn more information about the next thing that I am building.

Drew Appelbaum: Brian, thank you so much for coming on the show today. Congratulations again on the book and best of luck with everything.

Brian Requarth: Hey, thank you. I appreciate it. It was a pleasure to chat with you.