Matt Bowles: My guest today is Alondo Brewington. He is a software developer, poker player, options trader and martial artist. He has been a full-time digital nomad with no permanent base since 2016 and he has now been to over 40 countries. Alondo is also the host of the Cocoa Nomad podcast where he discusses location, independence and financial freedom as he travels the world.

Alondo, welcome to the show.

Alondo Brewington: Thanks, Matt. Man, it’s really good to be here, man.

Matt Bowles: I am so excited to have you here. We should just start off by setting the scene. You and I are in person today doing this interview from Nairobi, Kenya.

Alondo Brewington: Yeah, it’s a beautiful view as well.

Matt Bowles: This is our fourth country together on the continent of Africa. You and I have been to South Africa, Tanzania, Rwanda, and now we are hanging out in Nairobi, Kenya, which is such an amazing city. But I feel like we should just start this off by reflecting on one of the most incredible experiences that I have had, which you and I had together pretty recently, which is that we did a safari, safari in Tanzania. Can you share a little bit about that? Just for folks that have never been on the safari in general, and certainly people that have never been to the Serengeti in Tanzania, what was that experience like for you? What were some of the highlights?

Alondo Brewington: I mean, it was really mind blowing. I went in with no expectations of what was going to happen other than seeing certain animals and just the views, the expanse, just the sheer size just really blew me away. And when they said, well, we’re going to see this migration, I was like, yeah, okay, we’ll see a few animals along the way. But just blown away by the sheer number of animals and then the wildness of wildlife, I think is probably the best way to put It.

Matt Bowles: It was incredible because we went to the Serengeti, we went to the Ngorongoro crater, which was created millions of years ago. And now, like 25,000 animals live in this enormous. It’s technically a caldera. And we went there, we went through the Serengeti, we did game drives. We saw some incredible animals so close. We had elephants that were walking up literally six inches from our vehicle.

Alondo Brewington: That was a little dicey moment there.

Matt Bowles: I’m like, what’s going to happen next? And we were like, right in the middle of it. But we had cheetahs and lions right next to our vehicle.

Alondo Brewington: Yeah, the sleeping lions was amazing to see. I wasn’t aware that lions and other cats, leopards, slept in trees and they were taking naps and trees. But to just come upon them taking naps in just the middle of the day, no care, no worries. It was amazing. And then the cheetahs, to see those cheetahs, which I thought we were going to attack, I really thought we were going to see cheetahs at full speed, which is all I’ve ever wanted to see.

Matt Bowles: See, we did see some of the cats with their prey. We didn’t see an actual takedown, but we saw, for example, a leopard in a tree who had brought something like a gazelle or whatever it was, brought the gazelle that he had killed up into the tree. And you have the gazelle hanging on a branch and a leopard sleeping like three feet away.

Alondo Brewington: Yeah, it was just incredible because I was thinking about, like, how one that the cats, of course, can climb trees, but then how do you get your food up there? That was not a small animal that was hanging from that tree. And we just missed the lion. We saw the cubs. And when we came around and we saw the lion, was that a buffalo that it took down? But I know she was taking it back to the babies. So, we were just missing probably that live kill.

Matt Bowles: We were in the thick of it, man. And then we saw a crocodile eating a hippopotamus, which was completely wild because apparently crocodiles, they do not attack hippopotami while they are alive because they can’t bite through their skin and all this other kind of stuff. And so, the only way that they eat them is if they die of other causes. And so apparently this hippopotamus had died of, I don’t know, skin disease or something like that. Our guide was explaining. And then you have the crocodiles feeding on the hippopotamus. So, we got to see a whole bunch of really real, raw, actual nature as it was unfolding before us.

Alondo Brewington: Absolutely. The only thing I didn’t see was hippopotamus go Hippopotamus. Because they are known as the animal for which the phrase on sight is like a phrase they are not to be tribal with.

Matt Bowles: Yeah. I mean, a lot of people don’t know that they’re the most dangerous animal in the entire Serengeti in terms of their propensity to kill humans.

Alondo Brewington: Exactly. But I think people are sort of swayed by, like, Disney films of them dancing in tutus or something like that, and that’s just not the case.

Matt Bowles: Exactly. But we were able to get some incredible views of them up close and it was really just remarkable to see everything in its natural habitat. But we’ve been to a number of other countries as well. We’ve been to other places in Tanzania as well. So, I’m curious, I mean, you have now spent a whole bunch of time on this continent just so far this year. What has been your impression in general, your experience on the continent and any other highlights that stand out for you?

Alondo Brewington: So, for me, I think the sheer variety so far has been, like, the biggest thing. Coming into Cape Town, South Africa, which is my first time in this part of the continent, I had only been to Marrakech, Morocco before, which is northern Africa. I was told that Cape Town was Africa Light, as they jokingly refer to it. And I was just like, okay, everything was there. We lived in these really nice apartments. We lived in an area that was full of shopping residents. But then to get out and go to townships and to see other parts of the city and to explore other parts of the countryside. But then to go to Arusha was just such a pivot. Like, it reminded me very much of my first Remote Year journey in 2016. I really felt like I went from this massive urban city to a quote, unquote, real. Now it’s gotten real.

And the activity infrastructure, everything was there, just not at the level that you might get in some of the other cities. So, it dispelled a lot of maybe some mystique or some rumors or stereotypes about, like, oh, everything is backwards. It’s like, it’s slow, but it’s not backwards. It’s loud, it’s dusty, but it’s not backwards. You can get into certain things. The food was really good. I, Richard, was really pleased with a lot more of what I saw. People, you do have to have a skin for if you’re going to be in the middle of a place like Arusha for a lot of the activity the constant hawking of goods and services. If you’re not used to that. And then we go to Rwanda. And Kigali is literally one of the cleanest places I have ever been in my life.

Matt Bowles: Cleaner than any city in the U.S. I’ve ever seen.

Alondo Brewington: Yeah. I mean, this guy, hands down, it’s so funny because we were there, and that Saturday was the last Saturday of the month. And supposedly this monthly cleaning and everybody goes out and for the first part of the morning, until about noon, everyone’s cleaning and the shops are closed. And we’re walking around for the previous few days. What are they going to clean? There’s no trash on the street. There’s nothing like, what do you possibly clean here?

Matt Bowles: It was amazing. They do have the last Saturday of the month; they have this thing where all of the adult residents just voluntarily go out and clean up the city for three hours. Every business is closed. You can’t go anywhere. There’s nothing open. Everyone’s just out cleaning the city. And it was remarkable to your point. I was like, what are they going to clean? Everything is already pristine. Kigali was the cleanest city I’ve seen. I was trying to think if I could compare it to anything. I’m thinking maybe Singapore.

Alondo Brewington: That’s the only. I was going to say the same thing. The only other place I’ve ever been that that was as clean is Singapore.

Matt Bowles: Yeah. And it is widely regarded as the safest city on the continent. And I’m out walking around midnight. There are women with their phones out at midnight walking around texting. Nobody is concerned about anything.

Alondo Brewington: I was never in any sense of danger or like my head was on, you know, normally his on a swivel when I go pretty much anywhere. And like you said, I just walk around at night. The biggest danger is like, when I walk down like this dirt road and slipped. That was it.

Matt Bowles: After the rain.

Alondo Brewington: Yeah, man.

Matt Bowles: So incredible. The experience has been so amazing so far. Well, I would love, at this point, Alondo, just go back a little bit and talk a little bit about your backstory. Just give folks a little bit of context. Can you share a little bit about where you were growing up and the cultural environment where you came up?

Alondo Brewington: I’d like to think I had a unique experience in terms of how and where I’ve lived. I was born in Philadelphia. My family is originally from North Carolina, rural North Carolina, and has migrated all the way up the Eastern seaboard. So, I have family all up in New York and Philly and all the way up to Connecticut. But my section of the family migrated to Atlanta in the late 70s and so ended up leaving. We left Philly, went down to North Carolina, and went to Atlanta. And because my father was in the military, I ended up moving around a bit. So, I have three places where I primarily I call the Georgia liner. I lived in Atlanta, Georgia, Charleston, South Carolina. And I did spend some time in my parents’ hometown of Goldsboro, North Carolina, where I’ve lived a number of years as well.

Matt Bowles: And can you share a little bit about what the cultural dynamic was like there in terms of like people you were surrounded with? I mean, what were you exposed to? What was it like coming up there?

Alondo Brewington: So, it was interesting because the early phase is Atlanta, going to elementary school there. And for one year or so I lived in the swat. I live in southwest Atlanta. If anybody’s familiar, I went to Kimberly Elementary School. If you know Atlanta right about Tharl, you know where that is. I lived off of Green Bar in Kings Ridge Apartments. And that was an all-black school in the black city, in the black part of town. But then I was having a little trouble, and I went to live with my auntie and uncle on the east side in Decatur and got to live with them.

And it’s like funny, it’s like the parallels to Fresh Prince because I was born west Philly and I did go had one little fight and I ended up living with auntie and uncle and went to a school called Fernbank, where now there’s a museum of natural science and history, there’s a planetarium there. So, it was a very mixed school, and it was very diverse. Ironically though, it wasn’t the most diverse. It was after we moved to Charleston, South Carolina, when my dad joined the Navy, that I actually went to a school and lived in a neighborhood that was the most diverse that I would ever live in until my adult life, and that is in Charleston, South Carolina. I Lived in Northwoods. And at the time we had kids from everywhere. I mean, we had kids from the Philippines, kids from Vietnam. We got of course, black and white kids from the South. There’s Hispanic kids. I don’t know how this happened, honestly, in the early 80s of having this neighborhood that was just this unique, diverse mix of kids in one place. But I am super grateful for it.

Matt Bowles: That’s awesome, man. Well, I also know that music has been a huge part of your life from a very early age. Can share a little bit about the role of music when you are growing up.

Alondo Brewington: So yeah, music was always in the house. It was a big part. So, my father was a big fan of music, but my mother was a singer. I mean, it’s what she did when she wasn’t working. I mean, she would work jobs, but she sang at night. She was in a couple of bands, and she was a jazz and blues singer. And so, she was always working on songs, always had the albums out as you’re going through, and she’s constantly singing. So, I was exposed to a lot of music when I was younger, so I was always listening to RnB. Listen to a lot of pop music, jazz and blues, of course, because that’s what she was singing. She would be singing Billie Holiday; she’d be singing Sarah Vaughn. But then of course, she would do these shows where she would sing pop songs.

And she would even ask, she’s like, kids are listening to this song. Help me learn this song. So, we’d help her learn, like, some of the more popular stuff, because some of the gigs, that’s what people wanted to hear. And then my father was just super-duper into reggae, and particularly Peter Tosh, he also was partial to same things that Peter Tosh was a proponent in piano as well. So, I always jokingly said, I grew up in the clouds long before Google came along.

Matt Bowles: Well, I know that hip-hop culture also had an impact on you as that was arising. Can you share a little bit about that in terms of your interest in breakdancing, in terms of your interest in rap music as that evolved and what that was like at the time?

Alondo Brewington: Yeah, so with all these different diverse music forms I was introduced to, including also new wave and rock music and stuff, hip-hop felt like this new thing growing up that was hour. And I was a dancer as a kid. Like, I love dancing. My mother said I could dance before I could walk. And so, for me, dancing was big. And for a long time, it was just like doing disco dancing and things like that. And then Michael Jackson, of course, I could do like the killer Michael Jackson impersonation at school and everything. But then break dancing happened and I was like, oh, this is my chance to shine, right.

So, at school we would form these little ciphers for lunch in the playground. And there would be a rap battle and there would be a breakdancing battle. And you had your crew. My crew was like, from my neighborhood, my apartment complex. There’s a few of us. And we had, you know, we practiced in front of the stoop. We had cardboard walking around with someone. They had beatboxed. You know, we were on it. And so, it’s like, we’re ready to battle when you go to school. So, I spent a lot of time doing that. And so, for me, the early years of hip hop and breakdancing in particular was a great way for me, as a shy kid, to express himself.

So, for me, it just really meant expression. I distinctly remember breakdancing, and one of the teachers, they finally started paying attention to it, and they’re like, oh, my gosh, I didn’t know you could do any of this stuff. Well, yeah, because I’m quiet most of the time. Nobody knows if I do anything. And hip hop stayed one of those things where I just continually listened to and just became a big fan of. It became an important part, especially back then.

Matt Bowles: Can you talk about the evolution of hip-hop as you were coming up? Because obviously it started in the 70s, and then it really evolved and arced quite a bit. I mean, can you talk about, for example, the first time that you heard Rakim, and then from there, when Outkast came out in Atlanta and sort of some of the different phases of it and how that impacted you?

Alondo Brewington: Yeah. So, when I was young, I remember Sugar Hill Gang. I remember Melle Mel and Furious Five and African Mabata and Soul Sonic Force and stuff like that. But all stuff was coming out of New York. New York was the rap place. So, everything would come down. But rap started to get a little more diverse. You started to see it grow. You would get these sorts of novelty type acts and stuff. I remember hip-hop, like the Fat Boys and the Skinny Boys and the Rapping dude and these kinds of things. And I was a big LL Cool J guy.

The first album I ever owned was LL Cool J’s Radio. The first thing I got, like, I had my own album, ironically, only on two albums that, and my sister and I shared Miami Sound Machine’s conga, which we played incessantly. But I loved LL and KRS. But I remember I was at my grandfather’s spending the summer, and his kid Mike was a DJ, and we went over and he started mixing and playing records. And I heard Rakim. And the flow was, like, so different because rap music was like, you know, you have this simple cadence that most people would do. And then this guy came out and just said, I ain’t no joke. I used to have the mic smoke, man. I’ll slam it when it’s done to make sure it’s broke. I’m like, whoa, hold up, hold up, hold up, wait.

And it was just mind blowing. He was just like, oh, this cat is on Something different. And that’s even in a role where we had Ella, who was great, and krs, who was great, and Coogee Rap, who was great, and Kumo D and. And Big Daddy Kane. But Rakim was something different. And to me, just like, signaled, like, this change of MCs, and you’re just like, oh, we can just play the beat and let this cat go, and that’s it. And so, I really was into for that for a long, long time, and watched it grow. Now, later, in the south, we didn’t really have our own voice, even with breakdancing. I remember, like, the only breakdancing group was in Charleston, was the Port City breakers, that were known, right?

And I entered a dance contest. You know, you could compete at the roller-skating rink. They have these dance contests at roller skating rinks and stuff, because that was our club back then. When you were a teenager, you’re young, the roller-skating rink was the club. So, if you went to Golden Glide or something like that in Atlanta, that’s where you went to dance, meet girls, do all the things. Same thing in Charleston. You get to this phase where the region doesn’t have a voice. And I’m growing up, and by the time I get to high school, we have some local artists. We have Raheem the Dream and MC Shy D and stuff like that. And there’s a group called Success in Effect, and a couple other local rappers.

But cats like Jermaine Dupri were just getting started. Tip wasn’t even around at the time. There was no TI and then these cats started coming out of southwest Atlanta, and you start hearing, like, oh, because we had RnB art. It’s like TLC was local in there. In fact, left. I went to high school when a good friend of mine, she went to Maze. And so, you would hear, but you know who these people were. But when rap came on the scene, they came on the scene in Atlanta with the Dungeon Family, and you’re just like, oh. And as Andre 3000 famously said, the South’s got something to say. And it was really a big moment of pride. I remember seeing the video for Southern Playlistic, and we got airplay, and it was just like, yes, this is us. We’re here. Listen, See us. We’re not just copycats. We’re not just mimicking the west coast or New York or whatever. We got our own thing.

Matt Bowles: And then as you were coming up in Atlanta and going to college and all of that kind of stuff, because you were part of some of the really iconic Things that were emerging at the time, the emergence of Freaknik and going to some of these iconic places like 112 and some of this stuff. Can you share a little bit about the scene in Atlanta at the time and how that was to experience it then?

Alondo Brewington: Yeah, I have to say, like, my college years, I was in the right place at the right time a lot. My freshman year at Georgia Tech, we won a national title in football. We just came off a Final Four baseball team, golf team. Everything is doing great. The Braves are playing well to go to the World Series. The Falcons got Deion Prime, Tom Sanders. Things are cooking. And then locally, with the music scene blowing up, we have these clubs that became really popular. Peacock was a hot spot. Club XS was this place that was always jumping. Then 112 became the spot to go to, in addition to this other spot I used to go to a lot called the Warehouse.

And so, it was really a great time. And it was at that time that Freak Nik blew up. My sophomore or junior year, my roommates and some friends were hanging out in the dorms on North Ave. And someone comes into the room and they’re like, hey, we need to go to Piedmont Park. And I’m like, what? It’s like, yeah, there’s something going on over there. So, we hop into the car. Like four or five of us piled into a car, we drive to Piedmont Park. Oh, my gosh, wait a minute. Something really is popping off here. So we go back to the dorm, we’re like, hey, everybody, let’s go. Everybody needs to get to Piedmont. It wasn’t the first big year. It was the first year that had any rumblings. The next year we were prepared. We rented a car, and we had like drinks and stuff and packed in the trunk, ice, all this stuff. We were ready to go. And that’s when the city discovered Freaknik and went, what in the actual hell is this? Because 100,000 people just ended up on the city that week.

Matt Bowles: That’s incredible, man. And then what was it like? Like, for people that have never heard of it, what was it?

Alondo Brewington: As I shared with you one time, as the cop told me, as I’m surfing on top of a car, you’re not in Daytona Beach. Get the hell out of the car. But it felt like that. It was like we took Daytona beach and Panama City beach and Virginia Beach and brought it to Atlanta, but with the Atlanta city vibe. Because in the daytime we were in the parks hanging out, mainly Piedmont. And it was cruising. It was cruising around. You’re cruising Around Monroe, you’re cruising around these avenues, Piedmont. And then at night, its Club time, Club Excess 112, wherever there was a party popping off.

And of course, a lot of times we’re young, we’re not trying to pay a bunch of money. We’re parking lot pimping, as they say, right. So, we just out in the parking lot meeting people. I literally remember these girls. I was driving by the Georgia Dome. I saw these girls driving their car. I’m driving my car. I just park my car, get out, start talking to them. I’m like, stop traffic. Just literally stop traffic. Did not care. I was like, this is what we’re here to do. We’re going to have a good time.

Matt Bowles: And at that time, too, I mean, weren’t you rubbing shoulders with all of these different artists that were coming up? You mentioned you would run into Big Boi from Outkast eventually around the city and this kind of stuff. Didn’t you have a night where you bumped into Tupac back in the day? Yeah.

Alondo Brewington: So that was October 30, 1993. That was the night we bumped into each other. He wasn’t in a great mood. I wasn’t necessarily in a great mood. I was trying to have a good time. We both got into respective fights. Mine didn’t involve gunfire with any off-duty police, but I actually ended up getting into a fight in the club with my roommate. My roommate and I with some other people. It wasn’t my fault. I was really trying to have a good time, but you know how that goes. One in, all in. So, Tupac was there, he left early. Clearly didn’t look like he was in the best mood. And the history is known what happened that night.

Matt Bowles: So, what did this for people that have no idea what happened that night, what did happen that night? And then what was your encounter with him?

Alondo Brewington: My encounter was brief.

Matt Bowles: Yeah.

Alondo Brewington: Mine kind of was like, what’s up with this dude? And I looked up for a second, I didn’t even realize who it was until I looked up. I’m like, oh, shit. Like, it’s Tupac. But later that night, he gets into it with some off duty cops and there’s like a shooting, but it eventually ends up, like blowing over in a big way. Because I don’t think he was at fault necessarily when it all came out. It’s like these guys never identify themselves and that kind of stuff. So, my fight was a little different. My roommate bumped into something. Next thing you know, it was five in two. I Was never happier to see bouncers throw us out of a club because we were about to get really, really beat down.

Matt Bowles: Yeah, I mean, that was a historic night. I mean, anybody that looks up the history of Tupac and all that kind of stuff will certainly see that night. So that is pretty wild that you had a run in with him prior to all of that stuff going down. And obviously you remember the date, of course, for that reason. So, I want to talk to you also a little bit about how your interest in world travel developed and how your first sort of international travel began.

Alondo Brewington: It started off really slowly, honestly, as a kid when I was at that school in Charleston, they’re very diverse school. My homeroom teacher, Mrs. Addis Flugel, may she rest in peace, was also my Spanish teacher. And she had posters of Mexico and Spain and Argentina in the classroom and just talked about these places. And she was from Argentina, and I wanted to go to these Spanish speaking places. Then of course, this is a kid’s dream, right? I’m sitting in the middle of this like a seventh grader who may never even leave. I’d never Left like this three-state area at this point in my life. So later I had a trip for work. I went to Canada, which, I don’t know, people count. Do you count Canada when you go to Canada?

Matt Bowles: Sure, we’ll count Canada. Depending on where you go, there’s all sorts of different types of diversity you can experience in Canada.

Alondo Brewington: It’s true, I’m just joking. But in 2002, I actually finally made a trip that I wanted to make and that was to go to Spain. I spent three months learning Spanish. I went to a language school. I spent a lot of time traveling around. Well, not just the country, but I traveled to other countries in that time. And that was my first real taste of not just travel but also having friends and roommates from different countries. So, one of my friends was from Brazil. His roommate one was from Ecuador. Another one was from the UK, so it was one Australian. So, it’s like really getting a mix of different people and where they’re coming from a different background. And it was really neat. And we did a road trip together. It was a ton of fun. We took a road trip to Lisbon and back with no plans, no itinerary, and no place to stay one night. Cause we slept outside on the beach one night.

Matt Bowles: What impact do you think that that trip had on you moving forward?

Alondo Brewington: For me, it was eye opening. I got to see life outside of what I’d known in the States. I was introduced to the siesta, which became a huge part of my life now I live by it. And I was like, oh, this is interesting. Like, they close in the middle of the day, they shut down the shops. People go home and eat, they sleep, and then they open up later. And then the night they’re up again. They’re like, things go until later in the night and everybody’s out. Like you go in Spain, families, everyone’s out at night. My favorite restaurant in Malaga on the beach was a place called Los Cuñao. Great paella, great Boquerón’s, good fish.

But they didn’t even have their first seat until about 9:30. And there’s a line of people waiting to get in. And they typically would do two seating. So, by 11 o’clock they were doing a second seating. So, it’s like, oh, not only is this a different style, but people are also enjoying life differently. They have a different pace. Family time and friend time are important. We’re not rushing. You’re not sitting, eating over a sink, or grabbing some fast food. There’s another way to enjoy your day. That was huge. And I’m like, I want more of this. I want more of this.

Matt Bowles: I agree, man. I mean, Spain has a tendency to do that to people that go there. I mean, I can remember my first time going to Spain and figuring out how the whole siesta thing worked. And it was like I was wandering around looking for spots for lunch, and I’m seeing all these people out there eating lunch and they’re sharing like a bottle of red wine for lunch between two people, and all these people are doing it. And finally, I was talking to some local people. I said, you guys drink a bottle of red wine for lunch every day? Like, yeah. I said, doesn’t it make you exhausted in the afternoon? And they’re like, yeah, that’s why we have a siesta. I was like, this now makes perfect sense to me. And then dinner’s at 10:30, and then people go enjoy the nightlife and then they go to sleep and then they do it. I was like, this makes perfect sense.

Alondo Brewington: Yeah, I adopted it, and I tried to make it work. When I returned to the States with less-than-optimal results. And then I just realized that I needed to go the other way. I needed to make my life fit instead of the other way around.

Matt Bowles: Well, I know that you later then did a study abroad program. You went back to some different spots in Europe. Can you talk a little bit about that experience?

Alondo Brewington: Yeah. So, I went to grad school in 2005. And for my study abroad portion, which is at the end, in 2007, was a study abroad in the Czech Republic and Hungary studying transitional economies. And for me it was the next opportunity I got to go abroad seeing another side of Europe, because it wasn’t as advanced. They were coming out of an oppressive regime and people were adopting entrepreneurship. They talked about companies coming in. I got to meet and talk to both large companies like Microsoft and even smaller outfits and smaller startups and incubators and like, this is how we’re trying to change the mindset and move forward with our businesses and economically. So, it showed me that transition takes work, takes capital, takes time, and it takes a change in how you think.

Matt Bowles: You eventually decided to do a Remote Year program. You actually did a Remote Year program, a 12-month program before I did. You did the second one ever. You were on Battuta. And I have some very good friends that did Battuta as well. So, I know it was a really amazing group. But can you talk a little bit about your transition to being able to work remotely and then your choice to become a nomad and start traveling the world?

Alondo Brewington: Yeah, so I started working remotely fairly early. Well, so my first actual opportunity to do work remotely was in 2002 in Malaga. I used to do contract work for a hospital in Rockdale County, Georgia. And I used to use a tool called Crystal Reports. Anybody that’s old enough will know. And I would do the reports and send them back to the hospital via email. And that was how I continued to make a little bit of money while I was still abroad. Fast forward to 2010, I was back into contract work, doing work remotely, but not necessarily far flung. So, our clients were in Atlanta, but we were working out of a local co working space or cafes. And that’s what started my mini nomadic journey. So, what I started doing, friend Warren and I, we started a podcast in 2010 called the Digital Nomad Podcast.

And we had this thing that we would talk about. It was mostly about productivity, but we had this thing that I just said, let’s not record a single episode from the same location. One of us had to move and be somewhere else. So, I was already migrating around between my home in North Carolina, my apartment in Atlanta, and occasionally going out to Florida. And traveling around doing various things in Florida. Warren was doing something very similar. So, we managed it for a while. We kind of hit a wall, as you do with podcasts. We got about 10- or 12-episodes in. Okay, what do we want to talk about now? Because it just Sounds like everybody else’s productivity podcast. So that was my first podcast. I did a second one later that was about iOS development, because that’s my specialty. I do iOS development. I was on that one for a few years. But for me, the nomadic part was important because I could do all of these things no matter where I was.

And so, I was nomadic. I would spend some time in Atlanta, and I would go to North Carolina, my house. I would stay for a couple of weeks, maybe a month or so, then maybe I’d go down to Florida and stay in Miami for a couple of weeks. We’ll drive around. And then I started planning these trips around, theme trips. I would do a poker theme trip where I play poker around. I did a barbecue theme trip where I ate barbecue in a big loop from North Carolina all the way out to Austin, Texas and back. I did golf loops. I would play golf in all these different places. I was experimenting with change of location, still working, getting work done, figuring out ways to, oh, this place has good Internet. Here’s a public library I can go to that has free Internet. Here’s a cafe, work for a few hours, get in the car, drive for a couple of hours, that kind of thing.

Matt Bowles: And then when you decide to take that nomad journey international and travel the world and be itinerant without a permanent base, can you talk about that choice?

Alondo Brewington: Yeah, that was really Remote Year, because initially that wasn’t even my plan. My plan was to have what, you know, most people would describe as a gap year. I was going to go do the 12 months of Remote Year, come back to North Carolina, open up a co working space, and that was what I wanted to do. In fact, my plan during the year was just to study all the different co-working spaces we were in during that year and just try to learn, like, oh, what’s the best way to make community? What’s the best way to use space? You know, I even had a space that I was already trying to buy. I had the layout, I had it sketched out.

I’m like, okay, so at this space, I’m like, let me use Remote Year to have this great travel experience. But also, if it impacts the layout and where do I put the desk? Do I need a coffee bar? Doing all these things? And about four months in, something changed. And it was like, I really do like doing this as a lifestyle. And I don’t know if I want to stop. By month six, I knew, and my uncle came over. I met him in Barcelona, and I told him that this is June of 2016, I want to sell my house. I don’t want to live here anymore. Let’s make that happen. And that was it. I went back two months later; I sold one of my cars. I sold all the stuff in the house, furniture, my washer and dryer. Actually, I sold my second car to my uncle. I tried to sell the house that day. If I could have gotten that person to buy the house, I would have given her a low-ball price. I said, if you give me X amount of dollars, you can have the house and everything in it. As I was done, I was ready. I realized at that point I’d seen enough. I was convinced.

Matt Bowles: And then when the Remote Year program ended, which was a 12-month program where Remote Year, the company takes care of all the accommodations and co working space access and flights to all the different places and everything. When that program ended and you decided you wanted to maintain this lifestyle, how did you then go about structuring your nomadic lifestyle from there?

Alondo Brewington: So, the first part of that was I did feel the need to slow down because as part of that Remote Year program, the 12 month program, you’re in a different country every month. And that is a pace that can really be tiring if you’re packing up your stuff every four or five weeks going to a completely different country. Maybe there’s a different language, there’s different cultural rules to learn, different things to navigate. So, month 13, a lot of us from our group went to Bali, spent a month there, kind of like extending the party a little bit longer. But after that I settled in. I went back to Thailand, I went to Chiang Mai and I’m living there for like five months, just staying there until the summer. And so, I try to create a little bit of stability or consistency while I’m on the road and traveling now. At the end of that, I realized that I do like to mix it up because in the next two or three months I was all over the place again. I was back in Europe. I went to like six or seven different countries in Europe. And then I finally, eventually made my way down to Morocco by September. October.

Matt Bowles: Well, I know that Mexico also has a really special place in your heart. And I love Mexico as well. Can you share a little bit about what you love about Mexico?

Alondo Brewington: I never thought Mexico would be a place that I would even visit. It was a country to the south, neighbor to the south of the U.S. but it was never on the radar. And one month I think I was in Colombia, I was in Medellin, and someone from Roi Remote Year said hey, why don’t you come hang out, check us out for a little bit. I was like, okay, I’ll come. So, I spent two weeks in Playa del Carmen and then I spent two weeks in Mexico City. Supposedly I supposed to be in two weeks in Mexico City. I looked up, I was at the end of my six-month visa on arrival. I fell in love with Mexico City. I didn’t expect it just came out of like nowhere, that everything just worked for me. It’s a massive city. There are tons of stuff to do. It is the most walkable city I’ve ever lived in. I walk everywhere in Mexico City. I have a rule. If it’s not raining and it’s less than an hour to get there, I’m walking.

And I know a lot of people won’t necessarily do that, but like, I lived in Del Valle and my friends, a lot of people live in La Condesa and Roman and these other places. I would just walk. I would walk from Dubai all the way up to Conesa and just hang out and then I would walk back home. And similar to what you said in Kigali, walking around, I’ve walked around all hours of the night in Mexico City. Now, I will say this. Of course, there is a side to the city where I think you can do this even at night. There are other parts of the city where I would absolutely recommend you not do that at night. So just a bit of a disclaimer of relative safety depending on the neighborhood, but I’ve never felt unsafe there.

Matt Bowles: Well, you have a number of different interests, hobbies, passions, pursuits that you do as you travel around the world. I want to dive into a few of them, maybe just trace the lineages, because I know some of them go back to your pre nomad days. But can you talk about the role of martial arts in your life and sort of share a little bit about your trajectory with the martial arts?

Alondo Brewington: So martial arts, actually my love of them started when I was very young as a child, because I love kung fu movies and my dad and I used to sit and watch kung fu theater. Bruce Lee was the man. We just watched all the Bruce Lee movies. I remember one of the first movies I ever saw as a child was when my father took me to go see a Bruce Lee movie. But we’re also boxing fans. My grandfather talked incessantly about Joe Louis and his six-inch jab. That’s all I heard about. Joe Louis’s jab was iconic. My dad, we grew up at that time of just the best welterweight, lightweights of all time. Sugar Ray Leonard, Thomas Hearns, Roberto Durand, Wilford Benitez, Marvin Hagg. I mean, it was just on and on and on and on. I got to watch all these great fights, and so I learned a lot.

So those two things. But I didn’t get to participate because I had a mother who was really opposed to me doing any of that. I’m surprised she let me play football, honestly. So, I did get to play football, but martial arts were, like, out. So, I didn’t get to do as a practice practitioner until I got to college and I studied aikido. And then I studied a couple other arts, like Vietnamese kickboxing. And then I got to actually start boxing. Later in life, I joined a gym called Art of Atlanta Boxing. Johnny Gant was the owner and the trainer at the gym. Johnny Gantt fought Sugar Ray back in the early 80s. He also passed away earlier this year, but he was the first.

And it was literally like training in a kung fu movie. It’s like, you go in and it’s like in Karate Kid where he has Danielson, like, just do this one thing and get frustrated. I was only allowed to throw jabs. That was the only punch I was allowed to throw when I first went. For weeks and weeks and weeks that Johnny was just like, jab. Everything’s off the jab. That’s all you’re allowed to do. And I would slip sometimes and try to throw a right hand when I thought he wasn’t looking. Man, his eyes were all over that gym. Because every time he would just be like, nope, the jab. And relax, relax, relax. Those big things. Like, you got to relax.

And I learned that in martial arts of any kind, and maybe even a lot of sports, relaxation is speed and power. People are tense because they’re bringing all this emotion when they fight because they’re not practiced, they’re not calm. And I’m bringing a little Eastern stuff in here. I know because I’m influenced by some of that stuff, but the Zen of it and just settling in. And when you relax, you’re faster. You can think, you can see, you can react. Everything like they say in sports, everything slows down.

Matt Bowles: And then can you talk about when you eventually discovered mixed martial arts, and you started doing some of that?

Alondo Brewington: So, I guess about two years of training at the boxing gym, I wasn’t allowed to fight. And then somebody told me why. Like, I was talking to one of the heavyweights I used to get in the ring with, and he told me, he’s like, yeah, Johnny’s never going to let you represent the gym because you’re not here enough. And I was like, well, how often do I have to be here? It’s like, you have to be here at least five or six days a week. And I’m like, I got a job, man. And I work for a big law firm. I got to do this. I can’t be here that much. So, I left and joined another gym, a martial arts academy on the north side of town. Francis Fong, if anybody is in. And they had mixed martial arts training, and they were like, oh, you can absolutely train, and you can fight. You can fight and represent our gym them. So, I started training to fight. And so that’s how I discovered mixed martial arts. I studied jeet kune do, I studied Wing Chun, I studied Brazilian jiu jitsu. That’s where I got into Muay Thai. And I discovered capoeira. So those are the two that would stick with me for until now that I was introduced to.

Matt Bowles: Can you share a little bit about what capoeira is, sort of the history, the cultural significance of it, just for people that are not familiar?

Alondo Brewington: Oh, absolutely. I love it. So, capoeira is an art form that basically came to Brazil by way of Africa because enslaved people were not allowed to train. So, what they did was they hid the training in a dance. Some people call it dance fighting, but they misunderstand that. The purpose of that was to hide it so it didn’t look like people were training. And so, there’s music aspect to it and instruments you play. But make no mistake, I mean, there are real strikes, real kicks, real takedowns, and all of this stuff that’s in there. And I love it because it’s just a beautiful embodiment of it. And it was my introduction into learning this whole other culture and uniting things with other Capoeiras that I meet when I travel. It’s just this instant bond. You’re like, oh, play Capoeira.

And it’s like, I’ve been places to just hop into a Jorah and just start playing. And you’re always participating, even inside the hara playing. You’re clapping, you’re singing, you’re playing an instrument. It’s a very communal thing. It was mind blowing because I was doing all this MMA training, and this trainer, Sule, invited me to come out on this day to train capoeira. And the first thing he said was, he started playing music. He says, do a cartwheel. I’m like, dude, I haven’t done a cartwheel since I was like 12. What are you talking about? But the acrobatics were a part of that. And it just changed my perception on like I was setting all these hard, physical, punchy, chokey martial arts, and there’s this very free, liberal, expressive game that you’re communicating with this other person you’re playing.

And there’s a rule when you study cap wedding in these groups, if someone gets hurt, if you’re not playing the harder versions, if someone gets hit, it’s both people’s fault. Because it’s communication, it is a dialogue. I throw a kick, I throw a move, you dodge, vice versa. And you’re just learning. You’re doing different things and it’s just fun to play.

Matt Bowles: One of your favorite quotes is never give a sword to a man that can’t dance. First of all, who said that? What’s the origin? What was the original meaning? But then why does that resonate so much with you?

Alondo Brewington: So, it’s treated Confucius. It’s a Confucian saying. And when I was in college, I have a really good friend, my brother Raheem and I were. We bonded over the study of philosophy and religion and so was really into reading Tao Te Ching and reading Confucius and reading these things. So that was my off ramp. And it resonates with me because I see this tension. I see an anger in a lot of people. Even within the martial arts in the gym, you see the bravado. And I’m like, you don’t dance, you don’t let yourself live fully and freely, because once you do that, you don’t reach for that one tool, that weapon all the time. A man who dances, it can be women. But it’s just. That’s the phrase that you learn, this expression of emotion and the full range when you allow yourself as a human being, the freedom, the full range of emotions. It’s amazing the transformation it takes.

Matt Bowles: What were some of your most memorable martial arts experiences around the world as you’ve traveled to some of the places where you’ve been able to do that.

Alondo Brewington: One of the coolest was just like, I was literally just walking down the street in Lisbon and there was a hotter right there. And just instantly being able to just jump in, they were just come in, buy into the game. And I’m just like putting my bag down. And I did that again in Amsterdam. We’re on a trip in Amsterdam, walking down the street, another Hata. I just jump in and just start playing. And it’s just like, oh, this is great. The other one, and this is going to show up later in. One of my favorite places, is training Muay Thai in Koh Phangan. I just absolutely love, love, love, love these instructors are so good. Professional fighters are there. Like, there’s all levels, beginners, doesn’t matter.

And that’s the thing I love about it. Any dojo, any training ground that I think is really good is an open, safe space for training. And it’s a welcoming safe space for training. So, you don’t have to come in and you don’t have to worry about proving anything. But when you’re training, you’re sparring, you can trust your sparring partner to improve you without hurting you. And by hurting, I mean hitting you and attacking you in a way that you’re not ready for. You’re going to get some soreness. You need to get touched up a little bit. Let’s just. That makes you stronger. We still need to improve each other. It’s in a safe space. It’s within boundaries.

And so, in Copenhagen, just getting in the first stage, like, look, you get in the ring, he’s getting the ring. Start sparring. This is it. Best takedown I’ve ever had, though. I was sparring a guy your size, and he wasn’t respecting this kind of ethos. He was getting a little chippy, and I was like, I’m looking at the instructor. It’s like, yo, you’re going to get in here and do something. Finally, I just like, boom, next week, take him down. And it’s like he dropped like a sack of potatoes. I just cherished it. I was like, all right. See, that’s why we don’t get out of hand, and we keep it light. He says 60%.

Matt Bowles: Well, one of the other things that you do when you travel is you play poker specifically. No limit Texas hold’em. We just walked by a casino in Nairobi, Kenya, that has no limit Texas hold’em. And I know you are going to be hitting that up while we’re here, but can you share a little bit about what you love about poker, why it’s important to you, and what some of your experiences have been around the world playing poker?

Alondo Brewington: Oh, they’ve been really cool. So, I was introduced to poker, doing the big Texas hold’em, like, ramp up. I’m probably what you would call, like, a moneymaker, kid. Like, I saw Chris Moneymaker win, and I want to play this. And everybody was playing. It seemed like there were, like, these free poker nights at restaurants on a weekly basis. You could go around and play. So, I wasn’t even playing for money. I was just playing because I love the game and its an easy game to learn, but mastering is. I don’t think you ever mastered a game, right. I like it because there are two parts to it, right? You can play as a completely analytical player, playing the numbers and the odds and just going like, these are my algos and these are the pot odds. And now the new thing is the poker ranges, which didn’t exist when I started playing. When I started playing, you tried to put person on one hand, like all this person’s got jack, queen off.

But now it’s like a range of hands that could possibly be playing and you kind of whittle that down as you go. But I started playing and then I started playing for money. I started playing these private games, rounding basically around Atlanta and a lot of games until those got shut down. And then I just started traveling. I started again, like one of my nomadic things was I would play poker rooms in Vegas, Biloxi, Mississippi, dog tracks in Florida, like Gretna and in Jacksonville, playing in Jacksonville. And then when I started traveling internationally, I started looking for places to play. So, like for instance, in Lima, Peru, found a nice room in Uruguay, I found a poker room, played a WPT tournament in Marrakesh. Just like started saying, okay, I don’t have to quit doing this just because I’m traveling. They’re not everywhere and the games are a little bit different, but I do enjoy it.

Matt Bowles: Well, another thing that you do, which hopefully we’ll be able to go together and support you at some point on this trip, is that you dabble in stand-up comedy, and you perform around the world in different places as you travel. Hopefully we’ll get to do that here shortly on this trip. But can you share a little bit about that trajectory? Because as I go through your different, different hobbies and skill sets and things that you do, there’s just this massive range of things. Martial arts, poker, stand-up comedy. I mean, these are incredibly diverse spaces. I don’t think I know anyone else that performs in all of these spaces simultaneously. So, I think it’s an incredible range. And I’m curious for you what attracted you to stand-up comedy and what does that mean to you?

Alondo Brewington: I was a huge fan of standup comedy as a kid. I watched with my dad; my dad was a big Richard Pryor guy. But as a kid we got cable, and it was 24 hours. I was watching MTV. I didn’t believe they played videos for 24 hours a day. So, I stayed up 24 hours to just see that they did it. Having trust issues. I’m an Atlanta Falcons fan, so that’ll explain it. But I used to sit up late and watch George Carlin. He used to have these. HBO used to play his stand up a lot. And I really connected with the way he did. I mean, Richard’s the goat. He’s an all-time great. There’s no denying it. But I never thought I could do what Richard Pryor did. I wasn’t that kind of funny.

Even just hanging out with friends, there’s always kids who are naturally funny. Carlin hit it a little differently, though. And it spoke to me. I was like, oh, he’s talking about stuff. I like to talk about stuff. I like to be humorous when I’m talking about stuff because I think it’s like the teaspoon of sugar helps the medicine go down. Hey, I can talk about this in a way that gets people to think, but the laughter kind of softens so we can get into it. And so, he’s been my all-time favorite, just all-time favorite. And then I just love standup comedy, like across the board, how life moves you as you’re nomadic and moving from one thing to another, one interest to another, nomadically is. I was playing poker in Jacksonville, and I ran a professional comic. Chris Buck is sitting next to Chris. We started talking about our favorite comics. We both love Bill Burr. We started just talking about Bill Burr, like, oh, do you remember this joke? It’s like, whatever.

And then he’s like, hey, man, it’s like, I’m a comic and I host open mic. You want to come and give it a shot? I’d always thought about it, but it’s one of those fearful things, right? It’s like, man, I want to be on stage in front of people. What if I’m not funny? What if they boo all these things? And he said, don’t worry about it, just come out. It’s a small place. It was a little coffee shop. So, I go home, I watch YouTube videos of Greg Geraldo on how to do stand up, and I write a set. The first night, the coffee shop, there’s only seven people there. Like three are comics. I chicken out. At the last minute I went back out. I can’t do it. But I was so upset with myself that I said, I’m going to do it the next night. Chris says, don’t worry, come to Rain dogs. I’m hosting that one. I’ll give you a spot. So, I do that. I fortify myself.

I go to a Rain dogs packed house, like 70 people in this place now I’m like, I probably should have done it for the first time with a smaller crowd. But I get up there, I do my set, and it crushes the very first time. I cannot explain the sheer elation and validation from a crowd of people that are laughing at stuff that you have to say, like that it felt so good. So, I’m feeling great. When I step off stage, he gives me a light. Chris says, enjoy it, because you’re going to eat shit next time. It happens to everybody. You’re going to bomb. And he was 100% right. The next two times I went up, it was so bad. It was so bad. I was like, oh, this is what bombing feels like. But it’s a very good experience. And I wasn’t doing it consistently. And I went back in Playa del Carmen last year, and another professional comic came down. He started an open mic night. So, I decided to do it again. And that’s the set that you saw, was the set that I did there. And I’m now I’m looking to just do some more because I’m always writing jokes, and so I’m just constantly like, oh, I think something’s funny. If it’s timely, I write a joke. I really want to do more on stage. I’m looking for open mics right now here in Nairobi.

Matt Bowles: Yeah, man, we definitely got to get you one. And I do see you writing those jokes, and it’s so cool because you pick up different inspiration for material from your world travels, which I really appreciate. You and I were talking about our appreciation for Russell Peters, for example, who has just this massive range of international, diverse cultural humor that he can deploy in large part because he has traveled the world so extensively. He has immersed himself in so many different cultures on purpose. He has such a connection, and it’s just amazing to watch him do that. And so, as you and I are traveling around, I’m watching you writing stuff down like, he’s writing jokes, he’s got material, he just heard something or whatever. And so, I’m super excited to see your set, man. I hope we find you that spot, man. We’re all going to be looking for it.

Alondo Brewington: Absolutely, man. I’m looking forward to it as well.

Matt Bowles: Well, let’s talk about your podcast. You and I actually both launched our podcast in the same year, 2018. Your current podcast, I should say, because you mentioned you have done a couple previous ones before that, but your current one, Cocoa Nomad, can You talk a little bit about what the podcast is about, what inspired you to start it, and what people can expect from the show.

Alondo Brewington: So, I never wanted to be a travel blogger, but I also wanted to share my experience and talk about my journey in the nomadic journey. So, I decided after a few years of doing this, to start talking about location independence was the primary focus when I started living in different countries, working from different places, and I wanted to share that and encourage other people to do the same. And then I realized that the financial component was important. I’ve seen a lot of people get out here on this road, man, and don’t have a way to finance it, and they’re gone, they’re back home. It’s not because they don’t want to keep traveling, is that you have to be able to sustain yourself. So, I really made a conscious effort to start talking a little bit more about financial independence in addition to location independence. But I talked about what I think are important factors.

So, I have these three metrics that I think are very important whether you travel or not that I think are really important for financial health. So, I like to talk about that and then just talk about the things that help you when you’re on the road, when you’re working. Sustaining work is very important because you have to manage your time, energy, and attention, because you’re being pulled to all these wonderful things that you want to do, these places you want to see. And if you’re not careful, your mind share will be occupied, and you won’t get the work done that you need to get done to also sustain your ability. Because even if it’s not the money, if you’re not productive in the way you need to do your business or for the job that you have, I’ve seen people get called back. They’re like, hey, we’ve tried this, but your productivity is slipping. We need you back physically in the office.

And I believe that remote work really can work. I think it should be available to more people who can do it. I think more companies need to be open to it and give people freedom of time to work when they’re at their best. I am able to do that now and it’s been incredibly helpful for me.

Matt Bowles: Can you share some of your tips and philosophy on pursuing financial freedom in particular?

Alondo Brewington: Yeah. So, I say the three things that are most important wherever you are is your savings rate. First off, for every dollar that comes in, how many of those dollars don’t go right back out to pay for something. The second One is your investment return rate, whatever investment vehicles you decide to do. I’m not encouraging anybody to do anything risky. You can do anything very conservative. But you want to make sure that when you’ve taken those hard-earned dollars and pulled them in, have those go out and make some friends and bring them back, it’s a good way to sustain it. And then the other one is a metric that I like to, and I borrow this from startups because I’ve worked with quite a few of them and that’s runway. So, if everything goes sideways for you, you start losing. And I’ve had this happen. Clients are not paying, clients go away, jobs go away.

How long can you sustain yourself? Because that breeds the confidence to keep going. And if you do this in balance, what you can do is say, okay, I’ve got runway for six months. So, if I do lose these clients, I’m confident that I can start getting clients and build another stream of revenue within three months. I’m not feeling that pressure. The pressure can just ruin. It takes so much care of your mind, and you can be worried about things that you miss out on a lot of joy. It’s a thief of joy. And so, if you can provide yourself with that, it does so much for your mental state, which I think is important because you have got to deal with a lot of stuff out here. Language barriers, cultural barriers, the price of street chicken, who knows. And you want to give yourself the full capacity to both enjoy and withstand the vagaries of travel and international life.

Matt Bowles: Well, one of the streams of income that you have been focused on for the last year plus is trading options. And I know it’s a relatively newish endeavor for you, meaning the last year plus time frame. And I’m curious if you can share a little bit about that. You actually co facilitated a workshop for our group that’s here together on options trading and your lessons and reflections on it and sort of teaching other people on it. And I’m wondering if you can share maybe one why you like that particular space for you, but also how you approach a new revenue stream investment strategy when you go to learn about something. So back when you started this, when you said, okay, I’m going to approach this space and I’m going to attempt to learn about it and develop a skill level so that I can make this a profitable endeavor for me. What has been your approach over the last year plus to doing that? And maybe some things that might be applicable if you decide to pursue some other area.

Alondo Brewington: So, this is where I think you’ll see some of the connective tissue of all these disparate interests, and that is there’s a modicum of risk, right? There’s risk involved that is attractive to me. There’s risk in the ring, there’s risk of the poker table, there’s risk in travel. But I’ve learned that risk doesn’t have to be scary. The first thing you always need to do is understand. The more you understand something, the more comfortable you are. But like I said, getting in the ring and sparring on day one, you learn that punches don’t hurt as bad as you think they are. It’s like football. You play football, everybody talks about, get that first hit in, man. You get that first hit, that first tackle, that first punch. Now you’re ready to rock. You are ready to rock. Same thing in the ring. I get hit solid one good time, focused, ready to go.

Because the fear of the unknown is off the table, you start traveling into your first country. So, for me, options represent that. It’s understanding risk and understanding how money moves in a way that I never understood before. So, it’s like this. If you’re a real estate person and you know what wholesaling is, right? So, I go out and I find this deal, and then I go sell this deal to somebody else. And when I saw the equivalent in options, I went, hey, that’s just wholesaling. Or when someone says, oh, I’m going to get a hold of these shares of stock, and then I’m going to basically rent them out to somebody else, I’m like, this is somebody renting and then putting it on Airbnb.

So, I saw the parallels and going like, okay, now, there’s differences, of course, and there’s benefits that you don’t get with trading, that you absolutely get with real estate, but there’s mobility in it that I like I’m in and out really quickly. So, I like that, too, because I’m a nomad. I want to graze in this land, and then I want to move on. I’m in Tanzania, but I’m migrating. I’m going on my way to Kenya. I got to get. I got to follow the wildebeest and the zebra, so it gets you there. And so, for me, the first thing that I like to do is immerse myself, whether it was language. I went to Spain; I immersed myself in the language. Because of all those years of sitting in a classroom trying to figure out how to find the auto boost or puerto rico baño doesn’t get you there. You need to be in it.

You have to have investment of some kind into something to make it real. When the punches are real, you pay attention. It’s easy. When there’s nothing on the line, you can. Maybe you take more chances, too. You can play risk. Riskier when there’s no real cost, but you learn. And options has allowed me to do that. But it’s also made me pay more attention more closely to the market and how companies make money, how the overall market moves and underlying economic factors. And it fits within my life because it’s mobile in a way that other things aren’t mobile. I can. All these things I can do as a nomad are just sort of reinforcing for me, this lifestyle style.

Matt Bowles: Let me ask you one more question, Alondo, and then we’ll wrap this up and move into the Lightning Round. When you think back about all of the travel experiences that you’ve now had at this point in your life, what has been the impact on you of all of that travel? What does travel mean to you?

Alondo Brewington: Two things, validation and freedom. When I was a kid, I was always trying to fit into these different places and being moved around. And I always felt weird because, again, I always had the disparate interest. I’m not driving myself to any of these places. I was validated. I could go to a place and say, oh, people do enjoy this. I’m not an oddball. And even just liking to travel, I found other travelers. We’re not oddballs because we like this lifestyle. It’s like, it’s normal nomads. It felt so good to be on the safari. And I was at one of the gates and I was talking to a gentleman, and he said, you like the massage? And I was like, yes. I’m like Masai. They’re nomadic, they move around. I didn’t even know that they had, like, houses. They don’t carry a lot of stuff because they have stuff where they need to go. Travel light, travel often. It’s like, all right, cool. Second is just freedom. The freedom to be who I wanted to be is to validate that it’s like, I’m free and I don’t have to fit into a mold.

Matt Bowles: Awesome. All right, Alondo, at this point, are you ready to move in to the Lightning Round?

Alondo Brewington: Let’s get it.

Matt Bowles: Let’s do it.

Alondo Brewington: The Lightning Round.

Matt Bowles: What is one book that has significantly impacted you over the years you’d most.

Alondo Brewington: Recommend people check out, I would say, one of the most recent ones, actually, by Annie Duke, who’s a Former professional poker player and the book is Thinking in Bets. Reframing your thought process the best. One of the most impactful things she says in this book and was in an interview before I read the book was about dating. She said, go on a date and if it’s not going well, leap before the appetizer comes. Fold the hand but play a lot of hands. She also said date against type. So, it’s like try things that aren’t your thing because you don’t know enough to know what is your thing, whether it’s in another person or if it’s in a country. I did that with Mexico. Mexico wasn’t my thing. Then Mexico ended being one of my favorite places on the planet. It you got to start reframing. And so, for me, that book is really impactful for that. Awesome.

Matt Bowles: All right, what is one travel hack that you use you can recommend to people?

Alondo Brewington: I’m a big proponent of carrying two things all the time. A waterproof backpack, small and quick dry towel. The waterproof backpack is my day pack. It’s my gym bag; it’s my laundry bag. It’s versatile because it’s waterproof. I take it to this, my beach bag. And that waterproof towel dries really quickly. So, when I make a mess or I’m sweating, it’s versatile. Cleansing dries quickly.

Matt Bowles: If you could go back in time, knowing everything that you know now and give one piece of advice to your 18-year-old self, what would you say to 18-year-old Alondo?

Alondo Brewington: Be wrong more often. It’ll get you further than being right.

Matt Bowles: All right, of all the places you have traveled at this point, what are your top three favorite travel destinations that you’d most recommend people check out?

Alondo Brewington: Well, number one is Mexico City. I’m like, it’s just, just, I love that city. Copenhagen, Thailand, I really love. There’s peace to it. The food is great. I love riding a scooter around that island. And then Lisbon. Lisbon, Portugal is like one of my favorite cities. I love being there. I love returning.

Matt Bowles: All right, what are your top three bucket list destinations? Places you’ve not yet been highest on your list, you’d most love to see.

Alondo Brewington: Right now it is the Pyramids in Giza, it’s Petra and then Labella in Ethiopia. And I’m hoping to get all three of those done soon.

Matt Bowles: Amazing. All right, Alonda, we’ve now come to the most important question in this interview. I am about to ask you for you to name your top 5 hip-hop emcees of all Time. But before I do that, let me just ask you to share a little bit about what hip hop music means to you, why you love it.

Alondo Brewington: To me, it’s just an expression. It was rebel music. I mean, it was literally the post punk music is exactly what it is. And having people talk about things for me was very educational. Listening growing up with Public Enemy, even Rage with Zack de la Rocha, like, just really having something to say. Talib Kweli. There are MCs that have things to say, but you can also have fun. I’m a big Hammer fan. People talk crap about Hammer. I like to dance. I’m like, yo, dancing is an integral part of hip-hop. And I got into bait with somebody online a while back about this, you know? Cause they wanted to poo poo the dancing. I’m like, no kid and play and Big Daddy Kane had dancers. MC Light was dancing. Like to say dances in a part. People always hear you put some respect on her name. You know what I’m saying? So, yeah.

Matt Bowles: All right, Alondo, who are your top five?

Alondo Brewington: I’m not really big on individual MCs. My big thing is the duo. Okay, give you my top duo.

Matt Bowles: Go ahead, brother.

Alondo Brewington: These are all groups. Some of them contain some of my favorite MCs, though number one is top of the list De La Soul. The first time I heard 3 Feet High and Rising again, the validation that I could be different. And these guys were different. And Past Tense is one of my favorite MCs, period. He would be in the top five individuals if I had one. The next is A Tribe Called Quest. Again, the Native Tongues was like, again, jazz this different. The way they use jazz in the samples in a way that almost nobody was doing. I mean, you would get a little bit of that a little bit later with Nas. And why am I drawing a blank on from Gangster.

Matt Bowles: Guru.

Alondo Brewington: Yeah, Guru from Gangstar. And then next is the hometown duo. Man, they got something to say. Outkast, Southern Playlistic was just everything. Their albums they’re just solid. Every single one, they just keep bringing it. And they stopped when they wanted to. Man, they did shout out to those two. Big boy, if I ever catch you on the bowling alley again, man, I’m going to try to. The fourth is Little Brother, heavily influenced by some of the aforementioned groups. But again, coming out of Dirty Durham has something to say in the South. And being from that whole Carolina plus Georgia thing, I love seeing artists come out. And Fonte is just again, just the way he weaves. I just love it. And then the last one is the wild card. It’s the best rap group that doesn’t exist, and that’s Method man and Redman. Dude, when those two combine, it is just the best to me, because of their styles, you know, Redman’s just. Just out there and that’s just bringing it. I mean, you know, if you Wu Tang, he just brings it. And so, I just love them together. It’s just one of the best.

Matt Bowles: I just saw Redman live unexpectedly in 2019. I was at the south by Southwest conference in Austin, and I was there in the capacity. I was presenting on a panel on digital entrepreneurship, type of panel. And at south by Southwest, of course, they have music festival. Everybody who’s everybody’s there. And I didn’t really understand this until I went, but the number of 90s hip hop megastars that were just there walking around, performing at different things, all of this. So, I go to this, this DJ show and it has like big name DJs, just Blaze and Jazzy Jeff and all of these people. So, it’s a big name lineup, but it’s only billed as a DJ show.

So, we’re there, and I’m there with these other hip hop DJ friends of mine. And we’re like, right in the front. It’s standing room, but it’s. We’re right in the front, like a few feet from the stage. And then just Blaze is on and he just starts to talk. He’s like, yeah, I just called up one of my homies from New Jersey to see if he would be willing to come out where everybody’s looking around, be like, like, no way. Redman comes on stage, I’m three feet from him unannounced, and he just spits for 45 minutes. This puts on an entire show. It was one of the most unbelievable things I’ve ever seen because I remember when his first album dropped in 1992, I remember it came out. I had it. It was such a significant thing. And then this many years later, I see him and he’s three feet away from me. Unbelievable.

Alondo Brewington: Yeah. I also remember exactly where I was when Redman’s first album dropped. We played that thing on repeat, like, a lot. It was so just like when he flipped it in Korean, I was like, oh, this dude is crazy. It was like bananas. You know, he’s a skydiver also.

Matt Bowles: I did not know that.

Alondo Brewington: He’s done like 90 jumps.

Matt Bowles: Wow.

Alondo Brewington: Yeah. He’s again, very interest, man. People give the freedom to just express and be, man. I just think it’s a wonderful thing.

Matt Bowles: That’s an amazing brother. Well Alondo, at this point I want you to let folks know how they can find you, how they can follow your journey on social media, how they can listen to the Cocoa Nomad podcast. How do you want people to come into your world?

Alondo Brewington: I am the Cocoa Nomad on all the things you can find the Cocoa Nomad podcast. You can find me on YouTube at the Cocoa Nomad, Instagram, the Cocoa Nomad, Twitter, all the things. I try to be consistent and so any way you want to engage like feel free, questions, comments, whatever.

Matt Bowles: We are going to link all that up in the show notes so folks could just go to one place at themaverickshow.com go to the show notes for this episode. There you will find all of Alondo’s social media handles, links to his podcast and links to everything he has mentioned and recommended on this episode as well. It will be all at one place at themaverickshow.com.

Alondo, this was amazing brother. Thank you for coming on the show.

Alondo Brewington: Thanks for having me, man. I’m really excited. I was happy to be here.

Matt Bowles: All right, good night, everybody.