Matt Bowles: My guest today is Ashley Company. She is a social entrepreneur, storyteller, activist, and the founder of Jelani Travel, which has curated over 600 cultural immersion and service trips to Africa and elsewhere around the world. She is also the founder of Jelani Gives, which spearheads initiatives to sponsor U.S. passport fees for young adults facing financial constraints. Ashley is a sought-after keynote speaker on topics including Black Identity, Africa Tourism, Solo Travel, Cultural Competence, and Women in Entrepreneurship. She has been featured in Travel and Leisure, CNBC, Africa, Forbes, Essence, and many others that you would know. Originally from the U.S., Ashley is committed to fostering cultural understanding and social impact around the world, and she has now spent time in over 100 countries, including 30 countries on the continent of Africa.

Ashley, welcome to the show.

Ashley Company: Thank you so much. I’m so excited to be here.

Matt Bowles: I am so excited to have you here. Let’s just start off, though, by setting the scene and talking about where we are recording from today and the fact that we have agreed to make this a wine night. It’s sort of the Aperitivo hour now. So, we have just poured our wine and we’re going to be drinking through it as we chat into the evening. I am actually in the Blue Ridge Mountains of Asheville, North Carolina, and I have just opened a bottle of red wine from the Canary Islands in Spain. So, I’m going to be drinking through that tonight.

Where are you, though, Ashley? And what are you drinking?

Ashley Company: Yes, I’m actually drinking some Chenin Blanc from South Africa. And I am on the stolen land of the indigenous people of the Susquehannock people, also known as Baltimore, Maryland.

Matt Bowles: Baltimore, Maryland, big up. One of my favorite cities in the U.S., and that wine from South Africa, I feel like we should just start talking about that. You and I have both spent a lot of time in South Africa, and we’ve been drinking a lot of wine in South Africa, too.

For people who do not know about the wine region of Stellenbosch, Franschhoek, the whole South African wine region, which produces, in my opinion, some of the best New World wines on the planet. Can you share a little bit about some of your experiences in the South African wine country? What is it like, both from a visual perspective and an experience traveling there? And also, what are the wines like?

Ashley Company: Yeah, in South Africa, the Western Cape specifically is the most famous area known as wine country. And it’s one of the key things that had me sold. Like, okay, I have to start bringing people here. You always hear about wine in France, wine in Italy, and I’m just like, people are missing out on this hidden treasure. And the wines are just so robust and learning about it and just being in the wine cellar is just the full experience.

But especially the landscapes, because you have the mountainous areas as a backdrop and then these beautiful vineyards down below and the architecture of these pristine farmhouses, all the way to mansions, you name it. I mean, you just feel like you’re in the middle of a story, some type of romantic comedy. I actually do a lot of anniversary trips there. Girls’ trips, guys trips, whatever it is everybody can enjoy. Enjoy the scenery, the landscape, and the wines. Not to mention the food as well, the pairings are great.

Matt Bowles: Yeah. If you haven’t tried South African wines, you really should dip into them. And most wine stores will at least have some South African wines. And so, if you have a pretty good wine store near you, just go in and ask them about the South African wines. They’ll help you to navigate it. You’ll find some unique varietals like Pinotage, which you’re not going to find in other places.

And you can start sort of exploring some of them, but they are really spectacular and a fun region to dip into if you have not experienced those wines yet. But I love just traveling for wine and integrating these wine experiences into my travels. Whether I’m going to, like, old world places like Italy and France and those kinds of spots, or if I’m going to Argentina, go out to the Mendoza region and this kind of stuff. Do you also integrate wine travel into your experiences, Ashley?

Ashley Company: 100%. It’s one of my favorite things to do. I’m always like, okay, what are the world wonders? Let me check that box. But then also, does this region of the world have wine? If so, that’s one of the top things I’m doing when I’m there. And now it’s gotten to the point where, how interactive or what type of experience can I get in that wine country?

So, in Mendoza, I really loved doing a biking tour to each winery. You know, a little boozy biking. It’s pretty fun with those beautiful backdrops and sunsets and the malbec of it all, you know?

Matt Bowles: And a lot of the grapes that they grow in the new world, such as in South America, originally came from France. So, the Malbec grape and the Carménère grape that they grow in Chile, or the Tannat grape that they grow in Uruguay, these are all French grapes. But then when you go to France and you taste the wines that are made from those grapes, a lot of times a, they won’t even make 100% wine from those grapes. Cause a lot of them are just sort of used in blends. But if you do find them, like, if you have a Malbec from Cahors in France, it’ll taste pretty different from the Malbecs from Argentina.

So, it’s such a fun thing to just go around the world, and then you just learn about this stuff. Like, almost all of my wine knowledge that I have is just literally from going on tours in different parts of the world and just listening to this stuff, and then you learn about it, and it’s just such a fun way to learn new stuff, but also drink amazing wines and also have unbelievable scenery.

Ashley Company: I mean, it’s a win-win. And to your point, I’m also always learning as I’m traveling and going on different wine tours, because at one point, I didn’t realize that there was even such a thing. I knew there was red, white, rose’, right? But then I’m learning when I’m in New Zealand that there’s orange wine, and I’m learning in Morocco that there’s gray wine and there’s green wine in Portugal, and I’m like, okay, there’s more color, way more than I even knew, and I’m here for it all.

Matt Bowles: It’s amazing. And then, like you said, you can start setting up epic trips around wine-related events. So, in Bordeaux, in France, they do this festival once every two years. And I went to it back in 2018, and it was, like this mind-blowing festival where they have all of these tall ships come in and just park right along the waterfront, which look like pirate ships, you know? And then they have, like, a hundred grand Cru wineries. Just bring down, like, two vintages, and you can just go in and do this tasting, and it’s just like, I mean, it was completely insane.

And then I went out to Burgundy, which is, like, the birthplace of the Pinot Noir grape, and there’s, like, thousands of years of wine history there. And so, you’re just in these places, and you’re like, what is my life right now? It’s just crazy. But you can really plan interesting travel around wine events. I went a few years ago to Alba, Italy, in the Piemonte region, because there they have the international White Truffle festival. And I didn’t know much about truffles at the time, but it was sort of, like, shortly after the pandemic.  So, a friend of mine and I were just like, we need to emerge from not traveling, and we need to emerge in style. I mean, we need to do something like over the top.

And so, we went to the international White Truffle Festival in Alba for a month. Let’s just go for a month and we’ll post up. And Alba is at the base of both the Barolo and the Barbaresco wine regions, which are two of the best wines in all of Italy. So, we’re just there for a month, and they have these truffle sensory appreciation classes. You can take it.  So, you learn about truffles and how to smell them and how all this different kind of stuff, and then you’re just eating truffles and drinking Barolo for like a month, and it’s just completely insane. But you learn so much when you go to these culinary events, and you go on these wine tours. And it really provides a fun way, I think, to plan some travel highlights around the world as you go.

Ashley Company: Oh, yeah, absolutely. I mean, even on some of our trips in South Africa, one of their famous ones is the food and wine festival, but they also have sparkling wine festivals that they kind of pair up with their polo classics. Anytime that twine time is a good.

Matt Bowles: That’s what’s up. Well, I want to start off a little bit with your story. You’ve now been to over 100 countries. I want to rewind the tape way back and give folks a little bit of context on you and your journey and your story. And I would love to start all the way back and ask if you can share a little bit about where you grew up and what your earliest memories of international travel were for you as a young kid.

Ashley Company: Sure. So, my grandmother actually had my mom at 16, and she eventually used the military as a way to kind of propel her in being able to support her family and have a steady job. But that job also came with the benefit of travel every three years or so. And so, at one point, she was stationed in Adana, Turkey, and then I came along not too long after because my mom ended up having me at 19. And she also joined the military as a way to kind of help her. And so, at seven, I was actually going to visit my grandparents for the summer, and they were based in Turkey at that time. So that was my first and earliest international travel, which really, I’m sure, sparked a seed that changed my life and will hopefully change the world.

Matt Bowles: Well, I know that also as a kid, after your turkey trips, you ended up going and living in Korea. Can you share how old you were at that time in the context? And then when you think back, what impact did that have on you. What was it like for you at that age?

Ashley Company: Yeah, I think something significant that both my grandparents and my mom did was with the military, having them move to these places. There were still military bases that they could have lived on and just kind of been very insulated with American culture, but they both decided to live on the economy outside of the military posts and in actual local traditional housing and also having local neighbors. I can remember being seven years old and learning how to count to ten in Turkish so that I can play hide and seek with my neighbors.

And then the same when I was twelve in South Korea, living on the mattress, on the floor the way that they do, and using the bathrooms traditionally how they are, whereas five minutes down the road on the base, they would still build the bathrooms and all the housing American style. So, you just got a different experience. And there was also culturally, from a safety perspective, children were just respected and honored in a way that you could easily and safely hop in a taxi, go downtown, walk around, find ice cream, go eat.

You could do this at twelve years old where a lot of places in the US you couldn’t, or you shouldn’t. And so I just was able to explore and just learn so much at such a young age and also really get to know about other people that were just seem so different. And then you learn like, there’s so much we have in common. And I think that was a beautiful way to shape my character.

Matt Bowles: Well, I also want to ask, as you were coming up, what your college experience was like. I know you went to Hampton.

Ashley Company: Yes.

Matt Bowles: Yes. I want to ask about your experience. First of all, choosing an HBCU in general, and maybe if you can explain just for our international listeners that might not be familiar with that acronym and the history of HBCUs and the significance, can you share a little bit about your decision to go to an HBCU in general and then what your experience at Hampton was like?

Ashley Company: Sure. When I went to Hampton, one of the main reasons was because it was an HBCU, which is a Historically Black College or University. And my upbringing in Augusta, Georgia, even though I had moved around a lot, I stayed there the longest. That is where the accent stuck, and that’s where I claim as home. Being there, I actually went to a high school that was predominantly black, and I just kind of wanted to keep that party going. It was just, it felt like such a good and safe experience and to know that I could get my higher education and still be in that type of setting. But moreover, still a university where there were so many people from so many different types of walks of life that I could meet.

And the other consideration that I had about going to Hampton was that it was outside of Georgia, so that I would still be stretching and, you know, going somewhere different. And it was a little scary, you know when you’re 17 and you’re trying to figure out how you’re going to be so far away from home. But I also was a little bit used to it, having lived all over the world with family, and it was the best decision I’ve made in my life. I still continuously see the benefits from it with the relationships that I have in my personal and professional network in my career. I always tell people that going to an HBCU is the gift that keeps on giving, and that’s something that I wish that all black people could actually have the opportunity to do, especially if they want to go to college.

Matt Bowles: Well, I also want to ask you a little bit about your career trajectory and the path that you initially started on before you pivoted to entrepreneurship. Can you talk about that professional direction post-college and then also how travel came back into your life and the first solo trip you ended up taking.

Ashley Company: When I was at Hampton University, our president had a really good relationship with PepsiCo, and so they were always recruiting. And it wasn’t my initial thing to want to work for them, but I was actually in the second round of interviews to work with MBA. I wanted to work with NBA cares or at their headquarters office in New Jersey. And when that didn’t happen, I was like, okay, I need to probably look at some other things. And so because Pepsi was recruiting so heavily, they had this college-to-corporate hire program.

So, I got in and they had a need in Raleigh, North Carolina. So, I ended up working with them, which was great because it was an incredible leadership experience, especially with a Fortune 50 company. And I thought that once I get three or four years under my belt, that would make me really competitive for an MBA application to go to business school. But while I was there working, the first thing that I did was, now I have a little money and it wasn’t much vacation time, but it was a little bit.

So, I was like, let me go on a trip. And I was really excited because I’m turning 25. It’s a milestone birthday. I got my two best friends and I’m like, hey, let’s go. And we’re like, where should we go? And I found out that there was places with really good deals was the Dominican Republic. So, I was like, let’s do that. We’ll be at a resort. We’ll blah, blah. It’ll be so exciting. And literally, at the very last minute, both of them couldn’t go. And they literally had legit reasons. Couldn’t even be mad. Like, one had a clerkship with a judge you couldn’t pass up. Like, it still boiled down to, what are you going to do? Are you going to just stay at home and just celebrate your birthday in North Carolina, where you don’t know anyone, really, except your coworkers?

Or are you just going to go there, and face your fears? You don’t have to leave the resort. You can just stay at the resort, but at least you’ll have some good food. I was just, like, weighing the options. I was like, this is scary, but I’ve traveled before. I’ve never traveled by myself, but I can do this. I did this at seven years old. Again, it wasn’t by myself, but I was like, Ashley, you can do this. And it was one of the best decisions I ever made because when I got there, I actually fell so in love with Latin culture. The people are so nice. I eventually did end up leaving the resort just because of a lot of the people who were working at the resort that I met, and they were like, well, if you want to party, if you want to hang out with us, or you want to connect? You know, I just trusted my gut, and it was great because they treated me like family to the point where I was like, I’m coming back here, and I’m not going to stay on the resort. I’m going to stay with y’all.

I went back to work, and now I had this wanderlust that was different. It’s probably the moment that I started counting down my days. I have to get back there. So, I actually visited a couple more times by myself, but with them, I now have friends there, and I just learned so much about their way of life. Obviously looking completely different than the resorts that we were on. As an example, on the roof is where we would take showers, and it would be in a huge tub or tank of water, and they would cut open the top of a two-liter bottle, and you would use that to get the water out and just pour it over you. That was your shower. And then you would lather up, and everybody else would do it on top of their roofs, too. So, you could technically see each other. And I’m, like, nervous about, this is crazy. In America, we never get naked in front of anybody or that type of thing. So, I’m literally washing under my clothes, and the first night, right? Because I’m like, this is insane. Y’all are crazy.

But then by the second night, you do as the Romans do and you’re just comfortable, and it’s so liberating, and everything was so familial, and community based, and I just felt like I had another family, and I knew that I wanted to experience more of this. And so that’s when I started teaching myself Spanish because I also wanted to communicate better with them. And I’m still going back to work, but I probably have another year. I’m going to save a little bit more, and I’m probably going to travel some more, especially because I was getting up to the point where I felt like I had enough leadership experience so that I could take a gap year and then go to business school. It’s what I thought I was going to do.

Matt Bowles: Well, I know that your very first trip to the continent of Africa also was a big, transformative, impactful moment in your life. And I’m wondering, in the context of this story, if you can share how that trip came about, what the context was, and then what that experience was like for you.

Ashley Company: Yes, I was working at Pepsi, I was responsible for over 300 small and large format stores across Raleigh and Durham area, and also Chapel Hill. And so, if you ask me what fan I am, I was whatever fan of whoever’s district I was in at that time because we had big rival schools with UNC and Duke there. But I covered all of that territory. And so, part of my job was driving to different stores every day and checking on my full-time employees who were delivering products. And as a result, lunch would usually be whatever I’m passing by.

But because I have been traveling since seven in places like Turkey and Korea, I really love ethnic cuisine and different foods from all over. And so, I noticed this Kenyan restaurant along my way, and I had never seen that. The only African food I might have seen possibly would have been Ethiopian. And so, I was like, wow, I’m even thinking, like, where is Kenya? But I know it’s in Africa, but whatever it is, I want to taste this food because, you know, food is a way to travel.

So, I was like, let me just have this experience. And it was great because I had no idea what was on the menu. And I remember asking the waiter, it was a family-owned business, so he was the son of, of the owner, and he was giving me some tips on what to order, what his favorite things were. He was just really friendly, and he asked questions, and I was like, yeah, I haven’t been living here that long, and he was like, well, you should come to our parties. We host parties here in the evening. So, I went to a party with them, and he introduced me to his sisters.

We just hung out that whole night because they could party. That’s another thing that I learned. And so, it was late into the morning, then we went to IHOP, and we just became fast friends because now it’s six in the morning. We’ve eaten at IHOP. Now, I invited them to my apartment where we had a pool, and we just literally just hung out. It was like six of us. They had all been friends for years, and they just welcomed me right in. And so, within three weeks, they were like, do you want to go with us to Kenya? We’re going home for a wedding. And I’m like, absolutely. However, they had been asking their friends, because they also went to an HBCU at North Carolina A and T. And they had been asking their friends all through the years, people who they had known much longer, to come with them. And nobody ever did. Nobody ever took them up on it.

And so, they thought, we were going to ask. But she’s not serious. Nobody’s ever been serious. They didn’t know me. They didn’t know my background. I booked the ticket that week, and so it was so great. And I just think about how God has ordered my steps in so many ways that I don’t even realize until the moment. Because part of them feeling comfortable with me being there is wondering, how am I going to integrate with their customs and traditions? Will she be able to handle whatever? And I remember one of the places that we went, they didn’t have running water. So, again, it wasn’t on the roof, but in the tub of the bathroom. They had something like a tank similar to that cut-off two-liter bottle. They had a pot, and they would use that to take a shower whenever the shower wasn’t running. And they were so worried about me.

And I was like, oh, you have no idea. I was just butt naked on a rooftop doing this like it was nothing. And then back in my corporate job the next week, and they were even like, let me heat up this water for you so that it could at least be warm. I’m like, oh, this is nothing. I don’t need it heated up. So, they were like, oh, my gosh, she’s one of us. This is great. And so just those different moments, I had no idea was leading up to how I could be able to navigate Kenya or just the relationships that I was able to build and the trust I was able to build because I had other experiences, and it just kind of built that muscle memory and that travel muscle for when I would continue to travel throughout Africa alone and the confidence to do so, because I felt like I could face anything. Because I faced different things and with ease and excitement, because I had the opportunity to just be in those spaces that a lot of people often either look down upon or scared of or just don’t look at at all.

Matt Bowles: So, I want to talk about your transition out of your corporate job. Can you talk about that in the context of this Kenya trip and then what you did immediately after you left, what the plan was?

Ashley Company: Absolutely. So, while at Pepsi, when my Kenyan friends asked me to go to Kenya, what they also didn’t know is not only was I serious and I’m booking this ticket, but they helped become the catalyst of me turning in my resignation. Because I already knew that I had about a year left where I wanted to continue to save, and I wanted to continue to teach myself Spanish because I had plans to take a gap year before I went to business school. And I wanted to travel all of Central America and South America. But I kept pushing it off, month by month, week by week. I would always find an excuse, like, well, let me wait until this quarter so that I can get maybe this bonus, or let me wait until this moment.

And when they asked me to go to this wedding, they had certain dates, and they were also going to be there for a month. And, you know, in the US, we don’t get a month. Especially if you haven’t worked for a lot of years, you don’t get that much time off. So not only did I have to say yes to the opportunity, but I also had to say, that this has to be the time that I’m going to turn in my resignation because I’m not going to have enough PTO (pay time off). And so, I did. So, the date of the flight was the date that I put on my resignation letter which I obviously turned in two weeks before. And that really helped support the whole trajectory. The whole. It was like, now it’s showtime.

Matt Bowles: So, what was this gap year that you had envisioned and designed for yourself? So, after you got back from Kenya, what were the next moves?

Ashley Company: So, the next thing after the Kenya trip was to basically do the original plan, which was to travel all through Central and South America, from Mexico all the way down to Argentina. I didn’t know exactly how long it would take or how much it would take. I was nervous about that. So, I didn’t know if I would do every single country or not. But eventually, I did end up doing every country. And obviously, the more that I was out there, the better that my Spanish got, the more people that I met. Then you learn, because I was backpacking, too, and I was also couch surfing, and I was meeting people in hostels. And sometimes we would end up traveling together, and then we might break off and there might be another group of people who met randomly in Nicaragua.

Now we’re traveling together, and that all was a whole new world to me. And it was blowing my mind because even the term itself of gap year, it was probably more so something I learned when I was out there meeting other Canadians or Europeans, because it just wasn’t language that I heard used in the U.S. I just knew I was about to take a while before I was like, I’m going to take advantage of this time before I would go to business school. And that’s really what I was calling it. But I learned, like, that was a gap year that I created for myself.

Matt Bowles: Well, I want to ask you about some of your experiences during that year. I know that you currently run trips to Colombia. That is one of the destinations, obviously, you hit on that backpacking trip, and you continue to go back to and take other people, too, and show them how to experience Colombia. One of the places that I want to ask you about in Colombia that I have actually not yet been to, and I’ve spent a few months in Colombia, probably about four months in Colombia, and I’ve still not been here. And I know it is prominent on your itinerary is San Basilio de Palenque. And for people that have not heard about that, and they don’t know the history of what that is, can you share a little bit about the context and explain that, but also talk about your experience there?

Ashley Company: So, in Colombia, there’s always been this draw that has brought me back, and it’s always been one of my favorite places in the world. And I think it’s because of Palenque and the history of San Basilio de Palenque. So, the history is the freedom story. There were these different Palenque’s, actually, all around Colombia, and Palenque really just meant, like, a walled area. And it’s really walled with vegetation. It’s not anything with infrastructure, anything that’s built up. It’s a walled community that is like a fence where it’s really hard to get in, and it can keep you hidden.

And so actually, during the 16th and 17th century, where there are these colonial powers who are enslaving African people there. If somebody was able to escape and manage to get into one of these walled areas, it would be a lot easier to fight them off. So, there were different areas all around, but the only one that stood the test of time was San Basilio de Palenque, and it was founded by an African, his name is Benkos Biohó. And what’s so special about it is because they were so cut off, they were able to keep their tradition. So, there’s a lot of the Bantu language in their new dialect. So, there’s. It’s a Spanish base and an African Bantu language.

Whenever you’re able to have your language, some of their spiritual practices, the way that they view life and death and burials and funerals, they’re able to keep and hold on to all of that. And so, there’s actually been a recognition of those people to where even before they abolished slavery, they said, these people are free because they tried to come in and take them back. But again, because of the way that these Palenques were set up, it was really hard to get in. So, while they’re trying to make their way in, these people are already there and familiar with it, and they’re able to create a defense that defeated these soldiers from Colombia. Like, they literally would go out in droves and never come back. So, they were defeating them. And so eventually, the powers to be the kings, whoever the president, was saying, stop going out there. Let’s form a treaty. Let’s form something to let them just be free over here, and we’ll keep the people who we can control over here.

And all the way to this day, that’s the only Palenque that survived. And so now you can go there while we’re all free, and actually as tourists, and you can experience the drumming, the dance, the food, the language, the joy. I think it’s just a really powerful story that not just hearing it, but to be there and experience it, is really special. It’s not that far away, so you can take a day trip and have that experience. And it’s something that I’m really passionate about, people being able to have that experience.

So, I do a lot of custom trips, but it’s rare that we would do a trip that does not include it. They would have to really, like, say, no, we don’t want to go. Once I tell them about it, they’re like, I didn’t even know about that. Thank you so much. Please sign us up. And it’s usually always the number one highlight, and there’s a lot of highlights in Cartagena that you can experience from the beautiful beaches, the island, and the old city. But they always say that that experience is truly special.

Matt Bowles: Yeah, it’s top of my list for what I want to do the next time that I’m in Colombia. So, I love that you take people there. Now, the other experience that I have ask you about going back to this backpacking trip is after Colombia, you went to Venezuela. Can you share a little bit about your experience going from Colombia to Venezuela and what your experience there was like?

Ashley Company: Yeah. So, you know, backpacking through all of Central and South America, and as a backpacker, most of the time I was taking buses everywhere. The only time I took a flight is you pretty much have to take a flight or a boat from Panama to Colombia just because of how it’s structured and trying to make my way to Venezuela, I took a bus, and there was perceived danger at the borders with drug cartel. I didn’t know any of this at the time, but I took the evening bus, and I don’t remember how many hours, but it’s a lot of hours away to get to Caracas, which is the capital.

And so, at whatever point we were going through the border, it was late at night. It could have easily been midnight or 1:00 in the morning. And so those small border control offices were closed. And because it was a very local bus, the bus driver and everybody just assumed everybody there was either from Colombia or Venezuela, and they don’t need the same type of permissions or passport stamp to travel in between their neighboring countries.

And so, they kept going. And I didn’t realize until I woke up and I’m in Caracas that my passport wasn’t stamped. And even when I woke up, it wasn’t the first thing on my mind. So, I’m just getting out. I’m like, hey, isn’t there some type of border or something that we’re going to do or anything? And they were like, what do you mean?

And obviously, my Spanish was pretty decent, but it wasn’t that good when I’m in a panic and when other people are just finished a long bus ride and they’re just trying to get home, nothing is really clear. And again, I was backpacking. So, I reached out to somebody I was couch surfing with. It was a couple, and they were coming to pick me up. I was explaining to them what happened. They were like, this is actually really bad. And I was like, what do I do now? And they were like, well, you could go back to that border. But they were like, that’s a dangerous border. That’s why they didn’t stop in the first place.

And they thought that they knew somebody they were going to just try to figure out. But we also didn’t really have the time because they had invited me to their mother’s home, which is in Kumana on the coast. So, Caracas was just supposed to be a one-night stop, and then we were supposed to keep traveling. And they knew somebody at the border there, so they were like, we’re going to go talk to them. And they did. That didn’t work. And the real issue is I’m already in the country, right? So, it’s really about what’s going to happen when I leave. And also, at the time, President Chavez was sick and just not around, and it was causing tension and issues, and there was a lot of police checkpoints, and he shortly after, did die.

It just caused a lot of political and economic issues. And so, it just was a heightened time to already be there. So that with all the police checks, if they asked for my passport, I could have also had a problem just even being there. And so, it was kind of like this situation where I’m trying to lay low but also experience the place. And I also can’t have that much fun because in the back of my head, I’m like, what’s going to happen on the day that I leave? And I remember writing a letter to my family, and I gave it to this girl, send this if something happens, if I don’t get to make it out or whatever, you can let them know where I am that I’m sorry. And I just was so scared because they had told me about instances where they personally had been interrogated and they knew other people that had been interrogated in the airports. And it’s not like U.S. interrogation. It could be so much worse.

And part they said that it could be so much worse as an American because of how Americans treat them when they are in a similar situation. So, they were like, they might not take any mercy on me, you, and just giving me the worst-case scenarios. And so, I’m freaking out. And then we’re trying to strategize a plan, and they’re like, you could try to bribe them. You could try to just give them a little bit of money, but that could also piss them off. So, you have to be careful with that. And so we came up with this plan, like, just put a little bit of money in the passport. That way, if they are down for the bribe, they’ll just take it. If they’re not, I can just act like, oh, I didn’t know that was there. So, I considered that they were like, you could try the tears, but I don’t know if I could just cry on the spot. I don’t know if that’ll even work. I don’t know if they’ll care about that.

And so, I had all these different strategies running in my mind as I’m in the line ready to leave, and every time it got a little closer to one of the officers, and I’m like, which officer am I going to get? Am I going to get a woman or a man? Which one would be better? Would this woman understand my plight? Would a man just feel bad for me as, like, a damsel in distress? What’s my best strategy? And eventually, I ended up getting a man, but I know I just can’t cry on the spot. And I cannot tell if he’s even going to notice because I had plenty of stakes. Like, maybe he won’t even notice. And he starts looking up at me, then looking back down, then looking up, and I knew at that moment, like, he’s trying to figure out what’s going on. So, I’m like, should I handle money? Should I not? All these things are going through my head, and I’m just like, I don’t know what to do. And he called somebody over, and I was so worried about trying to figure out how I can cry on demand, but once he called somebody over, the waterworks just flooded. I was so freaked out and so scared and so traumatized and sad, like, what’s about to happen to me? I didn’t have to fake it. Those were real tears.

And they were like, calm down. They called some other people over, which made me cry even more. Eventually, they were just talking to each other and figuring out, and I explained the situation, and I even tried to show them that you can see the date that I even came into Colombia. So, you can tell that I have not been in Venezuela that long, like, more than I should have been. They just didn’t stamp me again with the language barrier, the tension, all the things.

Eventually, they just kept looking at each other, kept talking to each other. I couldn’t tell what they were saying, like, three or four of them. And they would leave one by one, until finally the guy who was still holding my passport handed it to me, and he was like, you can go. Don’t do this again. Don’t do this again in our country. And I was just like, no problem. Thank you so much. So, I got out of there and, you know, lesson learned. Just, you know, figure out how to get your passport stamped when you come in. It’s not a game.

Matt Bowles: Well, let’s talk about where you flew from Venezuela, because I know that this destination has played subsequently a massive part in your life. So, can you talk about where you went from Venezuela and what that experience was like?

Ashley Company: Absolutely. So, my final destination from that flight was the amazing Trinidad and Tobago. I love my sweet TT. That was my first time there and I’ve been back at a minimum ten times since. I go almost every year. At one point I was going twice a year, and it was for the carnival. During that time, I was literally getting there for the carnival. And it was my first carnival experience in general. And it just so happens to be the best carnival in the world. I don’t care what anybody else tells you, that is the best place. And coming from such a, “Oh my God, what’s going to happen to me? Tell my mama I love her” moment to the best carnival in the world. It was amazing. Like a complete ultimate low to an amazing high. And I’ll never forget that experience. The whole twelve months was just unbelievable.

Matt Bowles: So, explain what Trinidad Carnival is like. I have a bunch of Trini friends that have been trying to get me to come. I have not yet been super high on my list. I have been to carnival in Rio de Janeiro, in Brazil and some other places, but tell folks like me that have never been what makes it so unique, so special, and has such an important standing in your view of carnival celebrations.

Ashley Company: So, since you’ve been to Rio, that one is typically like, if you just googled best one, that one is the one that probably pops up. And I think it’s because of the amount of people or the amount of roadshow that they do. But when you’re talking about a just nonstop party that you don’t have to go to dance class in schools to be a part of the way that it is in Rio, you can just show up and sit and party nonstop. They literally say no sleep, no behavior. Different phrases that let you know it’s just a nonstop party from.

I mean, they actually party all month, but the partying really goes for a week strong. And on the most specific days start with my favorite day, which is Juve Sunday, but it’s technically Monday morning because you really get out there about three in the morning on Monday morning, and you party until the sun comes up. You’re on the road moving with trucks and the trucks either have bars to pass you, drinks constantly because it’s unlimited, or there are trucks that have speakers only because it’s blasting music. And as the sun starts to come up, that’s just a beautiful feeling to be having those vibes with so many different people, but they’re also throwing mud powder, paint, water, and so you’re really getting dirty. But it’s just like this epic feeling.

And then it doesn’t stop because now you’re going from basically two in the morning to about seven in the morning, and you just go to your hotel or wherever to shower. And everybody knows if you played duvet, because somewhere you’re going to miss either behind your ear, behind your leg, there’s going to be a little bit of paint somewhere, but you get all dressed up into probably like for the women, like some type of bathing suit or some type of short shorts or tights or something like that. And you do carnival Monday, which is the practice for Carnival Tuesday, where you really get the glitz and glamour of your actual costume and feathers.

But on Monday it can start as early as nine, but you just got finished at seven, so you don’t sleep. It’s just constant, nonstop until probably about seven or 08:00 p.m. that night, on Monday. And you wake up the next morning and you do it all over again. But super glamorous. And I’m tired just thinking about it, but it’s so much fun and the vibes and the beat of the drums just keep you going.

Matt Bowles: So, when you reflect back on that year of traveling all through Central and South America and closing it out with the Trinidad carnival, what impact do you think that that year of backpacking and couch surfing and having all of these different experiences had on you? And how did that ultimately shape your trajectory and your passions?

Ashley Company: I think even as we talk about my life timeline of travel and experiences, there were always these little pieces of my steps kind of being ordered for what I was meant to do and my purpose. But that year specifically was the year that I absolutely built the framework for my company. And I had no idea at that time what exactly the company would be. And I certainly had no idea that I’d still be doing it full-time, 100%, for eleven years. At the time, it was just building relationships, learning, becoming actually an expert in travel, traveling so many different types of ways, figuring out all the hacks to make it easier for people, to help people, and then also just really transforming my personal life and how I saw the world and how I wanted to contribute to it, because all of those countries that I was going to in Central and South America, I was also volunteering in just like, randomly on my own, not with an organization. I would just walk up to a school if I was in a very rural area and I would just ask, is there anything I can do to help?

They would say, yes, we would love if you could help teach English or whatever it was, or somebody might direct me, and they might say, well, we have a monkey sanctuary here in Costa Rica. We need volunteers. And I would go, whatever it was, I would just try to help in each country, country. Because I just was personally passionate about it. And then by the time I got to Columbia, it was Christmas time. And so, I asked my friends and family if they wanted to donate to just help me buy more toys. I was going to buy some regardless, but if they wanted to add to it, I could buy more.

And on Christmas, actually in Palenque, I traveled there by myself and just passed them out. And that was a really beautiful experience. But what I really, it was helping the framework, because when I started the company a year later, it was actually during Christmas time, and we did a Christmas project. I took what I learned, what worked, what made it easy, what could have been better. I used the pictures from Columbia to help raise more money, to do it on a bigger scale with young people in Ghana the next year at Christmas. And so, it really shifted everything because it was like that foundational period to create my company and to help me see that I actually don’t need to go to business school at the end of this year. I need to start this now. And I think that was the biggest piece.

Matt Bowles: All right, we’re going to pause here and call that the end of part one. Everything we have discussed will be in one place in the show notes. Just go to themaverickshow.com and go to the show notes for this episode. There you’re going to find all of the ways to follow, contact and connect with Ashley, as well as direct links to everything we have discussed in this episode. It’s going to be at one place at themaverickshow.com, go to the show notes for this episode. And remember to tune into the next episode to hear the conclusion of my interview with Ashley Company. Good night, everybody.