Matt Bowles: I know that you actually started Jelani Gives before you started Jelani Travel, so can you talk about what Jelani Gives is, give us a little bit about the history, and then how that eventually led to the founding of Jelani Travel.
Ashley Company: Yes. So, Jelani Gives started out where I took three girls to Ghana in Christmas of 2013. And it was only because I had a cousin through marriage who owned a school there. And I was like, I could go back to Kenya where I had my transformational birthright experience of going back to my ancestral homeland. And it felt right to start it in Kenya. But I didn’t personally have those relationships my friends from Kenya did. But to actually have a family member who actually owns a school, I knew I wanted to do it in Africa, but I was like, it should be Ghana. A shorter flight. It’s a boarding school at that. So, we already have some places to stay. We would be helping them. It just all made sense.
But I hadn’t been to Ghana yet, so now I had to go to Ghana and figure everything out. And on my way to Ghana, I had a layover in Egypt. So, Egypt was actually my second country in Africa. And I did a day there to see the pyramids. Kept going to Ghana, stayed there for a month, did all the tours. I can think of trying to figure it all out. What would make sense for the girls posting photos, trying to raise money?
They need to come here. Just really setting the groundwork for it. And I started with young people because I was nervous about trying to do something like that for adults, because I’m like, who am I to tell you how to travel? I’m still figuring it out. Whereas for young people, I definitely felt confident enough because I felt like I’d done enough, and I could really help them. And I wanted to expose them to the world. I wanted to help them become global citizens. I wanted them to know that there was more than just their backyard.
And I felt especially passionate about it because my upbringing was that I was able to see the world because of decisions that the matriarchs made in my family with the job that they chose. But what about all these people who were in the same socioeconomic status that I was in, who aren’t in the military, and they don’t have an outlet that will just allow you to travel.
So, I wanted to create a change that I didn’t see. And also, what was so transformative about the year of travel was that while I had a really great experience, I didn’t see anybody else that was black American. I barely saw Americans, but I still saw them. But I didn’t see any black Americans travel. I saw, like, one. And back in this time, there was before Instagram, I saw one black woman. She was from Canada.
So, I was like, there’s all these black people who are indigenous and generationally from all these different countries in Central and South America, but we don’t even know that globally, we’re the majority around the world. In the U.S., we’re always having to check boxes that say we’re the minority. And black people don’t even know, I know I didn’t, that even in Mexico, there’s history. The black people have always been there in so many different ways. I really wanted to create something where they could see that they could see themselves represented by physically bringing them there.
And so, I chose young people first. But what I didn’t realize is that was a huge undertaking, because I also had to raise the money for them. And that meant I had to start a profit, and that meant I had to manage a board. And that just meant so much. And I was completely driven by passion.
And so, I did it, and I did it successfully. But after we did that in 2013, six months later, we went to Trinidad and Tobago, because I had a relationship with the U.S. embassy there. And then we went back a year later to Trinidad and Tobago. And then I was ready to start taking them back to Africa. But during that time period, I had so many adults asking to be chaperones, and I might. I started off with three girls in Ghana. Then we went to five, then we went to ten. But I never had gotten to the point where he had a need for 30 chaperones.
And so, I saw an opportunity. Instead of bending over backward trying to figure out how to raise money for these young people to have these experiences, I could do a separate trip for adults and charge them for that premium service and use the profit from that to support my nonprofit. And so in 2015, I took the first group of adults and they went to Trinidad and Tobago. So, there’s obviously a theme here with how much I love Trinidad and Tobago, but it was also closer. But I already had relationships with the Ministry of Tourism and the U.S. embassy. And so, we started there, but I had this thing in me as I saw that things were positively happening and working with both the youth program and the adults, I was like, but I have to take us back to Africa.
And so, in 2015, I personally went to South Africa because there was a glitch with Etihad. They had a sale, literally, it was like $200 to get to South Africa, and they had to honor it. And so, I went with three of my friends, and that’s when I had that, oh, my God, South Africa is incredible. Why didn’t anybody tell me, I’ve got to bring people here? And I did. By 2016, the very next year, I started bringing both the youth program and the adults there and just kind of have been running both programs ever since.
But then once the pandemic came, I was no longer able to keep raising the funds for the youth program for them to travel. But we changed it to a passport program where we have an online curriculum called passport to cultural freedom that really supports their mindset on how important a passport is, how important it is to be a global citizen, and how important it is to consider Africa travel when you start traveling. And then we sponsor the fees for their U.S. passport. And so right now we have a partnership with a university that we’ll be announcing soon that we’re going to be doing passports for their university, an HBCU of course.
Matt Bowles: Well, I want to ask you about Jelani Travel today. You have curated 600-plus trips and experiences over the last decade. Can you share a little bit about what intentional and purposeful travel means to you and how you’ve integrated that into your company? And then today, who does Jelani Travel serve and what is a Jelani trip going to be like?
Ashley Company: Yeah. So, with Jelani Travel, we actually are very purposeful and intentional. And it started out with group travel, where there was always a service day because it pulled from, just like, my personal belief of wanting to give, just like we’re taking from the experience, wanting to also give back and also understanding how much of a better connection you can make within yourself, but with others, if you locally connect and not just kind of stay on the tourist path, just to not have it just be all about you, it could really be about community and partnership. If you really want to see a place, you have to get to know the people because they make the place.
So, we started out having experiences that centered around that. And over the last eleven years, it has evolved into a majority custom trip based. And so, if there’s a custom trip where that person doesn’t want that, then I’m so good at this thing. I literally can create whatever you want.
So, if you want, you know, you bring your kids and you want nanny service. If you’re looking for a honeymoon experience, it could actually have nothing to do with a service-based type of experience, but that’s how it started. At the end of the day, I am just really passionate about getting people to experience the best of Africa, because I think that they end up seeing the best in themselves, especially people of color and black people. I believe when they change the way that they see Africa, they change the way that they see themselves. And so that intentionality around it is really to give them the experience that they want. But just as an expert and with the experience that I’ve had, I also am able to curate an experience that sometimes they didn’t even know they needed, which usually results in healing.
Just being able to see themselves reflected and represented, even from subconscious things like the billboards and the advertisements, and just things that they wouldn’t necessarily see in the U.S., or the conversations that they get to have about similar struggles or stories of resilience across the dinner table from people who are in the same field as them but have always lived in Africa. Just really intentional experiences that allow them to think differently about the world around them, but also how they’re showing up in the world.
Matt Bowles: I want to ask if you can go a little bit deeper on that. I know that you do keynote speeches on black identity, and you have been going to the continent yourself for well over a decade, as well as taking a lot of other folks from the diaspora to the continent, oftentimes for their first experience, connecting with the continent. So, based on your own experience, but also the experience of others that you’ve been a part of, can you talk a little bit about black identity, maybe your identity to start with, but other people’s as well? If you’ve observed that and how that has evolved since you have started spending so much time on the continent.
Ashley Company: There was a moment when we transitioned from young people traveling with the nonprofit to only focusing on adult travel. And I had a bit of my own identity issue with feeling like I failed them. But I realized our passport program is actually having way more impact and casting a much wider net. So, I just had to reframe my thought process around it.
But what helped me was seeing how healing and how much impact it was having on adults who were having these experiences, who were healing some of their childhood wounds and childhood trauma, some of the effects of the microaggressions at work, and racism, where they feel just liberated and free and just have a moment to breathe differently when they’re able to vacation in Africa. And also, how that affects how they teach their kids and how their families are watching them on social media when they’re posting.
Like, it just has this huge ripple effect that I realized I’m still doing the work that I was called to do. It just looked different. And then the way that I started and the reason why I did it, for me going to the continent, how I identified before then I feel like I identified myself in a positive light, as a black person, as a human, as a woman in the U.S. But there was something missing, and I didn’t understand it. It wasn’t until I went to Kenya, and even until I did that travel in Central and South America, and I saw so many black people who were from there who spoke a different language.
All of that just opened my eyes to see that everything that I’ve been told in the media, I had a strong family structure that would tell me that these things aren’t true, and it helped, and that’s why I felt like I still had a positive identity about myself, but that subconscious negativity all the time, it still wears at you. And so, I didn’t realize that I could stand straighter, that I could walk taller, that I could feel freer until I was traveling, and I was having these conversations. And seeing that I’m not just alone in my community, in the U.S., we’re all having these same kinds of struggles, but seeing how they’re navigating it, seeing, I think, most importantly, how the community helps combat that, which I think we have less of that in the U.S. Because the U.S culture is just so individualistic, so kind of tapping into that, which is why I think travel is so important and can be so liberating because there’s so much, we can learn from others. And vice versa, of course.
Yeah. I think my identity was not necessarily, like, in a negative place, but I just didn’t know what I didn’t know. And the moment that I did, it was like bursting open. I got to yell it from the rooftops. I have to share it with everybody. And so, I started with young people, but then I had to keep going with adults. And I even thought of starting with people, either with children who were like I was when I was a child or adults who are like the people that I grew up around. And then it changed because it kind of caught fire with word of mouth, and we never even ran ads, and we were always sold out because they were having such authentic and beautiful experiences, not just because of the landscapes and the food and everything that I would meticulously curate, but also the community that was being built both with the people on the group.
I would purposely, like I said, have people come to dinner, have events where people in those places can also connect. And all of it was really healing. And I realized that because it kind of blew up and people were now telling their networks it was extending beyond the people that I know or who was just following me. And so now we had executives and just different people that I wouldn’t necessarily run into who were so excited about having our trips and then even wanting their own custom trips. It’s my milestone birthday or it’s a semi retreat or whatever it is.
And so, I realized that they all need it because we would have very personal moments and there would be tears and there would just be breakthroughs and just conversations. And you just realize at whatever level, financially, education, whatever it is, everybody is still trying to find community. They’re trying to find a sense of belonging. They are trying to heal something. And the community that we create, the experiences that they’re able to have, some of these leaders never take a moment for themselves. So even just not having to think about planning anything, they literally just sign up and they don’t even have to keep paying. They can literally click a button, and it’ll just have a recurring monthly thing. If they don’t have to think about anything, they literally just have to sign up. And then they show up and they can just be there for themselves because oftentimes they’re always there for everyone else and they’re depleted.
So, when they have these experiences, they really can’t tap into their true potential and their full identity and have those deeper conversations and connect on a deeper level because we’ve set it up and made it safe to do so.
Matt Bowles: Well, I have to ask you about your trip to Sierra Leone in 2021. Can you start by giving folks a little bit of historical context about Sierra Leone, your connection with it, and then what the 2021 experience was like?
Ashley Company: Sierra Leone is a place that I did know of because I’m a complete geography geek and I have a personal goal to go to every country in Africa. So, I knew what it was called and where it was, but I did not understand the deep history of it until probably around 2020. I was in the house reading about all kind of stuff during the pandemic, and then I had no idea what my connection was to it until 2021, when I took the African Ancestry DNA test that is completely different from ancestry.com.
African Ancestry is the only black-owned DNA company, and they are the only ones that can determine your match to your tribe. And as a result, Sierra Leone had an historic memorandum and partnership with African Ancestry that said, if you are from one of our identified tribes, we will honor citizenship. And so, I am from the Mende tribe, and I was able to get, in their inaugural, very historical. There was so much press and all these things.
We went to Sierra Leone, and the President himself handed me my green passport, and I mentioned that it’s green because I think that’s so cool. I’m just so used to blue. I’m like, yeah, that’s the one that’s given me so much access to visit West Africa. But it also gave me a kind of another level or sense of identity to feel like, okay, this is a place that will accept me as a citizen. I can vote. I can be involved. I can purchase land differently and with more flexibility. It made me want to look forward to starting a business. It made me commit to going there every year. So, I didn’t want to just get the passport and take off. I really wanted to get to know it more.
And the history is really phenomenal. Another one of resilience, because the capital city is called Freetown, and it’s called that because there were a lot of different Africans from other places that got settled there. Like, this is where you have to be. This is the free area. And so, as a result, the main language is Creole because it’s a mix of there were so many different peoples coming from different areas, but there are some tribes that just hit there the whole time, like the Mende, but it just has such a unique history. And then I knew one person from Sierra Leone, but she had such a traumatic history having to leave there as a child from the war, that she didn’t really want to talk about it. She was actually one of the people that when I got together with the Kenyans and their friends, she was one of their friends, and we all hung out. And so, you know, I had an interaction with somebody years before I ever even knew. Like, oh, I’m from there, too.
Matt Bowles: Can you talk about how you actually got your passport, what the ceremony and experience was like? And then after you got it, what did you do with it? How was it to travel on a Sierra Leone passport?
Ashley Company: Well, as you know, I don’t have the best history with going through borders, but this time, I had crossed a few other borders over land without issue. But now, the first time getting a passport from Africa, from the motherland, that I know is my ancestral homeland was really special and using it for the first time to go to Guinea Conakry, which is its next-door neighbor.
It was hectic because it’s just hectic in general. But them expecting to get a U.S. passport, and I’m handing them one from Sierra Leone, and I was like, yeah, I’m from here, let me cross, you know. So, that was really cool. But just being handed the passport from the president itself, the ceremony, all the good things that they said about wanting to connect their brothers and sisters who were lost during the transatlantic slave trade, it was really emotional.
There were probably 30 of us, and we also dressed to the nines in the most fabulous African attire. And we were just so proud. The sun was shining that day and just felt beautiful, smelled good, smiling from ear to ear. There was a huge processional. There were drums, there was dancing, and the energy was just powerful. There was so much press that people locally were just coming out to greet us, and that felt good. Cause it truly felt like a welcome. They were excited about what was happening in the country, and we also had seminars to really talk about what it can look like to invest and potentially buy homes.
And the ones who wanted to, we immediately got bank accounts and just really got integrated as citizens. And I personally have always wanted to adopt. So that was another part of the conversation where now, as a citizen, I could potentially do that a lot easier than I can in the U.S. and for a lot less, which was also something emotional to just even think about, too, really just a whirlwind of emotions that day. Really proud moments.
Matt Bowles: Well, I want to ask you about some of the currently available trips that you offer to the continent. I was looking through your itineraries, and I was just like, wow. I was smiling through all of the different places that you take people. I think there are so many amazing opportunities, and I’m hoping you can just share a few of them. I think maybe the one I want to start by asking you about is your trip to Ghana, Togo, and Benin.
You know, of course, how much I love Ghana. You and I were both at Detty December watching Burna Boy together in 2022, which was amazing. But I have actually not been to Togo or to Benin. Can you share a little bit, for example, about people that would like to experience that trip and what that itinerary looks like and what there is to do in Togo and Benin in particular? Cause I haven’t been, and I’m looking forward to going.
Ashley Company: You can literally drive through Togo from border to border, and probably two to 3 hours. And both Togo and Benin are French speaking. One of the most popular shows that could highlight it if you wanted to get some background on it, is a Netflix special that came out not that long ago called high on a hog, and it breaks down the food, but also some of the history and interconnections between southern cuisine and African Americans with Benin.
It is also, I find, quite similar, and I don’t want any people from Togo, or Benin to get mad at me, but I only say similar to Ghana in the sense that if you really think about borders in general, these are made up names and invisible borders that were organized by Europeans who came together at a convention in Berlin to say, this is how we’re spreading it out, and you get this land, and you get this land. So, the borders aren’t really real from a national perspective, you know, I get it, but they literally cut through the people in their area.
So, if you go to the border of Togo and Ghana, the way people are there on both sides, and they’re speaking the same language, even though one speaks French and Ghana speaks English because of, again, that conference. So, it’s similar in the sense that you can find some of the same exact foods because they’re the same exact people and they’re in the same exact landscape. It’s just these invisible borders. But I think it’s cool to go to because it’s more of an extension, and they do have French influence, and it is still a different place.
So, there’s going to be different waterfalls you can experience. There’s going to be different more stretch of coast that you can experience, and just different histories. I think if you kind of want an extension of that, I would recommend it. If you’re just somebody who’s like, I like to stay in a place for a long time and really get to know all the different nuances of the place, then you could potentially go to one or two without going to the other, whereas that wasn’t my experience. I spent most of my time in Ghana, and then I spent a short amount of time in Togo and Benin, and I really loved it.
Another movie from the perspective of Benin is Woman King, and there’s a place called Weeda that if you watch woman king, you’ll see where the uprising is, and it talks about the history of the woman warrior. And what’s really cool I think my favorite thing to see in Benin is in the city center. There is this huge statue of one of the woman kings, if you will, one of the warriors. And I’ve never seen anything like that. We usually see statues of men, or if you do see statues of women, they just might look more angelic. They don’t necessarily look like warriors, but she looks like the most warrior of warriors and also really huge. It’s not just like a simple statue. And she’s bronzed and it’s right on the beach, so you can see as the sun sets. And, yes, it’s super dynamic. It’ll actually remind you, Matt, of the Renaissance monument in Dakar. But just think just the woman, and the woman is the warrior. It’s incredible.
Matt Bowles: Let’s talk about your trip to Senegal. As you know, Dakar is one of my favorite cities in the world. I have been back three times. I’ve spent at least three months in Senegal. I just keep going back. And you have a trip to Senegal, and on that trip, you also take people to The Gambia. I have not yet been to The Gambia. One of the things I love about your itineraries, I’m just looking through these. I’m like, these are some of my favorite places that I talk about on the podcast all the time. And now there’s a way for people to go and experience them with you because you have these amazing trips There. So, what is your trip to Senegal and the Gambia like? What can people expect from that?
Ashley Company: Yeah. So with Senegal, there’s so much to see, and especially if I design a custom itinerary, I love to talk to people about what their vision is and, you know, kind of their quirks and what they love, and so that we can really just, you know, optimize that and make sure we’re getting the best of what the country has to offer and what they’re looking for. But like on our general itinerary that you would find on our website; you would spend a good amount of time in Dakar because Dakar is special.
A lot of our audience are people that love shopping. And so, the fashion in Dakar is just amazing to the point where even Chanel, the house of Chanel, actually had a huge fashion show and conference in Dakar, which was the first time on the continent, and that wasn’t that long ago. But even from a cultural and artistic perspective, there are so many greats who are doing so many different forms of art that you can find there, and art residences, and the food is amazing. So, from a culinary art perspective, some of my favorite food is actually from Senegal.
And I remember I did a cooking class there. Actually, when I went there, I had just someone who told me to call her auntie. She just showed me how to cook the food that we were about to eat in her home, and it was literally pounding everything from scratch. Some of those signature meals take hours to prepare, and you really get a sense of appreciation for just how delicious it is because you understand how much work goes into it. So, I think as a tourist on the itinerary, we always make sure to include those signature meals, not that you have to cook them, but that you get to experience just how delicious it is.
So, from the food and the arts and then the history, you’ll also visit Goree Island and go to what they call the house of slaves and learn the history there. They have a door of no return. And also, outside of just experiencing the city, it’s only been a few years now they have the African civilizations museum. But then once you’re finished with the city area, the popular place to go is Saly because it’s known for its pristine beaches, beach parties. It’s a beach town. So, you just have that more relaxing experience there. And it’s not that far away from Lac Rose, which is the Pink Lake, which is a cool experience where you literally see a body of water that is pink most of the year, which is really phenomenal. But you learn about the history of that.
But you can also travel even deeper. Like I said, on our custom trips, you wanted to go to the desert in Lompoul and spend the night riding camels, that type of thing. So, there’s so much to experience. And there’s other cities that are known for festivals, like Saint Louis. And if you keep going, one of my favorite things I think a lot of people love to do is as you get closer to The Gambian border, there’s an area where you can actually walk with the lions. And what I like about them is that they don’t drug them or sedate them or anything just so that you can walk with them. They’ve just raised them since they were cubs, so they’re used to humans, and so you can actually be around them without danger, but then also without hurting them.
Matt Bowles: Well, I love the array of places, and some of these are specific trips on specific dates that people can sign up for as well as your custom trip options. So, you take people, if they want to go to Seychelles, or if they want to do northern Africa and see Egypt and Morocco, or if they want to go to East Africa and see Kenya and Zanzibar, or if they want to go to South Africa and drink some of this amazing wine we’ve been talking about, and also see Zambia and Zimbabwe. While they’re there, you have all of these different options that are curated with your obviously ten years of personal experience and personal contacts that you’ve developed there and everything else. So how can people get more information about the trips and options to plug into a Jelani Travel trip?
Ashley Company: Well, the best thing to do is go to our website at gojelanitravel.com, but every time I do interviews, I always like to give people my Personal Instagram because I’d love to know whatever your questions are. Just let me know you came from your show and just reach out to me directly. I love to connect with the listeners and help however I can so you can follow me at @ashleyncompany_ and yes, Company really is my last name.
Matt Bowles: Love that. We’re going to link it up in the show notes, of course, so folks can just go to one place at themaverickshow.com and go to the show notes for this episode and get the direct links there.
Ashley, I want to ask you a couple questions, sort of behind the scenes, just entrepreneur to entrepreneur, because we’ve got a lot of business owners and aspiring business owners that listen to the podcast. Can you share a little bit, just reflecting back over the last decade about your transition into entrepreneurship from a traditional corporate job and then how you built and scaled Jelani Travel over the last decade. Can you give us some behind the scenes, maybe tips and lessons on how you did that?
Ashley Company: Yeah, I think the main way that I was able to create a business is to just do it. You have to launch the thing before you can ever truly analyze it. And after you analyze it, that’s the only way that you then be able to optimize it. And so just not getting, what is it called? Like analysis, paralysis, and overthinking. These are all the things of which I do, but in that moment, I had to just not do that and just put it out there, and then I can make it better and better. And so done is always going to be better than perfect. If I was just waiting for it to be perfect, I’d still be on year one instead of year eleven.
What that looked like for me is I didn’t need to have a plan in order to say, what kind of business can I start that can last for ten years? It was I see a need you definitely want to be solving some type of problem, but I want to work on that right now. And I’ll keep growing and hopefully it’ll keep being that way. But the thing about entrepreneurship is it can just take you on a journey in so many different ways where it might be something that you end up selling way before then but can look a lot of different ways.
And so just starting, I think, is the biggest tip. Don’t be afraid to just start. And then the biggest thing that is a lesson learned is not to do it all yourself. Get help. It’s actually better if you can pay for something, to pay somebody who can do it way faster, and it’ll just free up the part that you are good at to do that even better. That’s definitely a hard lesson.
So, if you don’t listen to anything else, definitely listen to that. But for me, once I did start the company, it really was on a, let’s just see what happens, because I really thought that I would go to business school so they could just teach me whatever I need to know to be successful. But at the time, there were so many things happening that felt racially negative and traumatic in the U.S. that I felt like I had to start right now because I felt like this was going to be a way that I could help more people feel liberated, and I just have to figure it out. And so, I was driven by that.
So that helped me just start right away and I don’t have to have all the answers. And then I also ran into some opposition where I wasn’t getting support from people that I thought that I should. And I didn’t let that stop me either. I was like, okay, I’ll fund this. I’ll figure this out. But I think there’s a difference between you trying to reach out and get support and not getting it versus you not trying at all and you refusing to get help and pay for help. Pay for good help. That’s two different things. You really have to do both.
Matt Bowles: What types of techniques have you developed for optimizing your time and being able to choose the highest leverage places to devote your time and your limited energy each day? Because I feel like as business owners, that’s an important thing that comes with time. And so, I’m curious now, ten years into your company, how you do that. What does your daily structure look like and how have you decided where to put your energy and then what to outsource and delegate?
Ashley Company: The thing that I found that helped me the most was doing a brain dump of everything that I do. And if you’re starting out, when I first started out, I was a solopreneur. So, you really are doing a lot of things yourself, and you really have to get it on paper. What is everything that you’re responsible for and that you’re actually doing it instead of just running on autopilot and just doing a little bit of this and a little bit of that, and you have no structure.
So, if you just write it all down, it becomes manageable to actually structure and look and put everything that you wrote down in quadrants. And the most important quadrant is what are the things that are actually making you money. And then you also have to look at a quadrant of what are the things that are taking up the most time. And from there, even if it’s taking up a lot of time, if it’s making you money, those are the things that you have to prioritize. But also, once you break those things out, it’ll be easier to figure out what you need to delegate.
But another thing that people don’t necessarily do is also identify out of all of those things, what are the things that you just hate. It doesn’t matter whether it’s making you money or it’s making you no money, you just don’t want to do it. If it’s that much of a mental block for you, in essence, it is still holding you up from making money because you’re going to keep procrastinating on it and it’s going to get in the way or it’s going to keep you from, you know, what’s on your list. And so, you’re like, I’m not doing anything today because I have so much to do. When you really could just delegate those things and feel free to only work on those one to three, like core things that, again, you need to put your attention on, either because you haven’t found the right team for it yet, or because it’s the thing making you the most money. And so, you need to pay the most attention to it.
Matt Bowles: How do you deal with stress as an entrepreneur? Every business owner I’ve ever talked to is familiar with what we call the entrepreneurial roller coaster, which goes up and boy, does it go down. In those downswings of the entrepreneurial roller coaster, how do you manage stress and continue moving forward with your business?
Ashley Company: My stresses have been people. I have to deal a lot with people. I have people that are clients, that these people are on the trip, so a lot of times they don’t know each other. And then I also have to manage the personalities and cultural complexities of my vendors and contractors in different countries, especially from female male perspective. Being an American, being a woman, I need to get things done, but I need to get it done in a way that’s effective. That can be stressful. I think those are probably the ways in which that stressed me out.
But when you pose that question, the first thing that immediately popped into my mind when I was the most stressed, I have ever been was surviving a global travel ban during the pandemic. You’re literally telling me I can’t do anything. And the payment platform that we were using completely held all of our money because they didn’t know what was happening either. That was a very stressful time. And how do I manage it? I think just like in life in general, I don’t know that this is the best for everybody, but I have a, okay, what’s the worst-case scenario and how do I walk myself through that? How will I move through this? How would I figure this out?
And once I do, then I feel calmer. And obviously, the worst case typically never happens, but I have a solve for it. And so, I feel like I can handle anything because I figured out what I thought was the worst-case thing. Like, I’ve gotten myself the panic down from this worst-case scenario situation. So, I’m not panicking over this anymore. I can just move ahead with what’s actually being presented to me, and that kind of works for me.
Matt Bowles: Well, I also want to ask, just reflecting on ten years of traveling to The Continent and taking people to The Continent and having social impact being a core part of what you do and what you’ve oftentimes integrated into a lot of your trips, how have your thoughts on navigating around some of the challenges of voluntourism or some of the pitfalls of voluntourism, like the savior complex and things that often come into play when, for example, American folks are going to the continent for the first time and so on and so forth. What have you observed over the last decade? What are your thoughts and reflections on that today? And maybe any tips you have for people that would like to contribute positively but don’t want to fall into some of the problems that are sometimes associated with that.
Ashley Company: It is a delicate balance of wanting to do the right thing, but potentially doing it the wrong way. And so, I think the most important thing that I’ve learned, and I even had to do myself, was always lead with what it is they need. Ask the people, whoever you’re trying to support or serve, what it is they want to see, what they need, how they would feel most supported. And then also, if it’s a bigger organization that you’re building or a bigger business, then you also want to make sure you’re incorporating whoever you’re serving into the leadership, so that even from just asking them what they need, whatever you’re hearing and how you’re interpreting that the leadership would need to be on both sides so that you just don’t miss the mark.
And so, for example, in my business, we were doing a service project. And so, the very first one, the reason why I got the idea to do it when I was just traveling solo in Colombia as a Christmas project or passing out Christmas gifts was because the year before at Pepsi, I didn’t know anybody there. My family wasn’t in North Carolina. So, I just wanted to give kids gifts. It was literally what I wanted to do. I’m like, I’m by myself on Christmas and I’m always driving these neighborhoods where more of my routes where my guys drove every day. So, I knew the neighborhoods where I always see kids out. I literally just went there, passed out gifts. That felt good to me. Luckily, it felt good for the kids.
When I was in Colombia a year later, traveling, I was like, let me do this again, because that felt good to me. And I’m assuming this is going to feel good for the kids. And it did. But once I actually formally started the company the next year, I asked the school, what do they want? And they just so happen to be a Christian school. And they asked, could you do gifts? And then what kind of gifts do you want? They said, “We want dolls and soccer balls”.
I’m so glad I asked because that’s so important to them because I wouldn’t have brought that because as an American, we don’t typically care as much about soccer / football. And so that helps. And then as I worked with other places, we never end up doing a Christmas project again or Christmas gifts because the needs were different. I always use the practice of asking them what it is they want. And so, they would say maybe one group, or one trip would say hygiene product, like we would just bring them what they want. And I just think that’s good practice because colonizing your giving approach is not the way to do it. I’m going to just tell you what you need because of what I think are from my lens. And I think that’s a good way to approach it. And especially how I felt good about just the area of volunteerism in general because I had seen some problematic practices with other organizations, with the whole savior complex.
What I also noticed is that part of the reason why I started the company, I wasn’t seeing a lot of black Americans travel in the first place. And so, as a result, when young people or whatever organizations we were giving aid to during our service project, I also noticed that they had never seen black Americans or people that looked like them, period. Black people, period. Coming in the service capacity, I thought it was actually healthy to see if you’re going to get some support, to see a group of black people that look like you saying, “Hey, we care about you”.
I even put on the shirt Jelani Women Cares, and we explain why we did these shirts, because we just want you to know that we’re far away. And I know your only image of Americans are what you saw on tv, and what you saw on tv were just movies, so you really weren’t seeing black people. We want you to know that we’re here. We think about you. We care about you. And I think it had a healthier outcome for them as opposed to the savior. I think it kind of, like, balanced whatever the savior conflicts that they might feel, because, like, they could see themselves represented and know that they could potentially be in those positions because they would talk about their work and make other connections and can see, we want to support you, but we also were in positions like you before, and you can feel motivated and inspired that you could be like us one day because they would ask those types of questions.
Matt Bowles: Ashley, when you think back on all of your travels that we’ve been talking about for over a decade, all the way back to that Dominican Republic trip and everything that’s happened since then, what impact do you think all of these travels to 100 plus countries have had on you as a person?
Ashley Company: The totality of my travels has changed the way that I see the world, but I think it was changing the way that I saw the world from a young age and just more growth, more evolution. But now, more recently, I feel we’re always rediscovering and evolving. And I just think that my travels have really changed how I see myself in so many multifaceted parts of my identity because I identify as a free black woman from Augusta, Georgia, but I also identify as a proud Sierra Leone. And I also identify as an activist and somebody who wants to help liberate the world through travel, because I believe if we were connected more, just as humans across these invisible borders, we really could change the world. And it starts with changing ourselves. So, I’ve just seen how travel has changed me, and I want to just continue on that path of doing that in a way that can help others.
Matt Bowles: Well, for people listening, that would like to hang out with you and me in person together, we are both going to be at Black Travel Summit in Fort Lauderdale, Florida, which is taking place October 10 to the 13th, 2024. I have not yet been to the Black Travel Summit event you have been last year. So, I’d love for you to share a little bit about your experience at black travel summit and what folks can expect if they want to come hang out with us this year.
Ashley Company: Oh, yeah. It’s going to be a great time. I was so excited to even find out about it. One of the things that I hate to admit through this long journey of entrepreneurship, it only until recently, like the last few years, that I even started going to travel conferences. And I just feel like that’s such a shame. I should have been going. I should have known. But it doesn’t matter, because what Anita and the team have created at the Black Travel Summit was so special last year. I’m just like, I’m so glad I know now. And so, if this is your first time hearing about it, I’m just so glad you know now. Don’t make a mistake. You definitely want to get your tickets, you want to get your spot, because it was just so much fun. It was invigorating.
You learn so much, but the people that you meet and just the way that they think about conferences, like, you get information, but there’s also a yacht party. Who would have thought of that? Or a yacht brunch. And then there’s a gala, an awards gala. There’s just so many different aspects. It’s not just what I used to think about when I was in a corporate. Going to conferences where you’re just simply in a room that’s too cold and just getting information put down your throat. Like, there’s really cool conversations being moderated by yours truly, and it’s just a really good experience. And I remember sitting in the audience thinking, I am so glad to be in this space, learning what I’m learning, connecting with people, and to now also be on the stage and being able to help facilitate a great experience for everybody. I’m really excited about that, too.
Matt Bowles: Well, for any Maverick Show listeners that would like to join me and Ashley and a whole bunch of other Maverick Show guests that are also rolling up this year, we have a 10% discount for you. And you can get that just by going to themaverickshow.com/bts. That stands for Black Travel Summit and then just enter the code: Maverick. And that will give you a 10% discount on your ticket. So come through, hang out with us. If you do grab a ticket, just shoot me a DM on Instagram at mattbowlesmaverick. Let me know that you’re coming too, and we’ll make plans to link up, and you get to hang out with a whole bunch of amazing maverick show guests.
Ashley, I think that is a great place to end the main portion of this interview. And at this point, are you ready to move in to the lightning round?
Ashley Company: Okay, let’s do it.
Matt Bowles: Let’s do it. All right. What is one book that you would recommend that people should read?
Ashley Company: The one that I’m excited about right now. There’s a trilogy, an Orisha trilogy by Tomi Adeyemi. And her third one just came out. So, it’s like Children of Blood and Bone, Children of Virtue and Vengeance. And the one now that just came out that I’m so excited to get my hands on is the Children of Anarchy. So that’s what I recommend. Read what I’m reading.
Matt Bowles: All right, who is one person currently alive today that you, you’ve never met that you would most love to have dinner with? Just you and that person for an evening of dinner and conversation.
Ashley Company: So, I’m going to manifest that I would have dinner with Fawn Weaver because I just recently started following her, and she’s a black woman billionaire, and I think there’s only six of them, so I think she’s number six. But I actually have been following her business journey as an entrepreneur, and I really loved her story, and she’s just also really inspirational, even her personal life. So, I would love to pick her brain at dinner.
Matt Bowles: All right, Ashley, knowing everything that you know now, if you could go back in time and give one piece of advice to your 18-year-old self, what would you say to 18-year-old Ashley?
Ashley Company: 18-year-old Ashley? I would absolutely tell her to go study abroad. I was worried about missing some significant experiences in actual college. That happens, particularly at HBCUs. And I was worried about missing it because you never know when it’s going to happen. I should have just went to study abroad because that in itself is one of those once in a lifetime things.
Matt Bowles: All right, of all the places that you have now traveled, what are three of your favorite destinations that you would most recommend? Other people should definitely check out, for sure.
Ashley Company: Tanzania or Tanzania, depending on how you want to say it. Colombia. I love Colombia. And New Zealand. New Zealand is just breathtaking.
Matt Bowles: All right, what are your top three bucket list destinations? These are places you have not yet been highest on your list. You’d most love to see.
Ashley Company: I would love to see the summit of Kilimanjaro in Tanzania. I would love to visit Jacmel, Labadie and Cap-Haitien in Haiti. I’ve been wanting to go there for years, and I would love to go to Antarctica on a very, very luxurious cruise.
Matt Bowles: Amazing. As you know, I have summited Kilimanjaro a couple years ago, and I know you, you are planning a trip to do that. So, we will keep in touch about that. And I am happy to give you as many tips and as much support as I can along your journey. I am super excited for that.
All right, Ashley, we have now come to the most important question of this interview. I’m about to ask you to name your top five hip-hop emcees of all time. But before you name your five, can you share a little bit about what hip-hop music has meant to you and why you love hip-hop?
Ashley Company: I love hip hop because the rhythm sounds good. I think the lyricism can, like, take you like, oh, my gosh. I didn’t realize it had this many different meanings. You could just be so clever with it and just the rhythm of being able to rap it. I love the history of what I learned about it being something that feels like a part of my community, a part of my culture. Those are the things that I think I like about hip-hop.
Matt Bowles: All right, Ashley, who are your Top Five?
Ashley Company: My number one, hands down, is Tupac Shakur. And then I also really like Foxy Brown. I really like Andre 3000 for sure. I love Kendrick Lamar. And then I think Lauryn Hill.
Matt Bowles: Ms Lauryn Hill, rounding out the top five. I love that. All right, Ashley, at this point, I want you to let folks know one more time how they can find you and follow you on social media and learn more about the opportunities to join a Jelani travel trip.
Ashley Company: Yes. So, you can go to gojelanitravel.com. You can follow me at ashleyncompany or my website at ashleyncompany.com.
Matt Bowles: All right, we’re going to link all of that up in the show notes so you can just go to one place@themavrickshow.com. There we’re going to have all the ways to follow. And I connect with Ashley. We’re going to have direct links to Jelani Travels so you can see the specific itineraries of all of her trips, which are frickin amazing. I suggest you go and check them out, and we’re going to have the special link for how to connect with us in person at Black Travel Summitand get a 10% discount. That’s at themaverickshow.com/bts, but it’ll also be linked up in the show notes for this episode.
Ashley, this was amazing. Thank you so much for coming on the show.
Ashley Company: Thank you for having me.
Matt Bowles: All right, good night, everybody.
