Building a Travel Business from Costa Rica with Matt Wilson

Matt Wilson

Episode Description

In this episode of the Expat Empire Podcast, we will be hearing from Matt Wilson. Matt is Co-founder and CEO of the travel company for people ages 21-35 Under30Experiences, and author of The Millennial Travel Guidebook. In addition to traveling around the world to lead tours for his business, Matt started going to Costa Rica in 2012 and lived in the town of Quepos until 2019. Matt hosts yoga and fitness retreats in his free time and his personal mission is to help people live more adventurous lives.

In this episode, you will learn:

  • How to leave your complicated and expensive lifestyle behind for a life of travel and adventure
  • Ways to merge your career and travel to create the life you want to live
  • The benefits and challenges of trying to run a business from a small surfing city in Costa Rica 
  • Some BREAKING NEWS about the exciting new cities Under30Experiences will be headed to after the pandemic

…and much more! You can find Matt at:

Eli Hermit produced the music for this episode, please check him out on Bandcamp at

Please leave us a review at more about Expat Empire and schedule your free consulting call to plan your move abroad at!

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Episode Transcript


Welcome to the Expat Empire Podcast, the podcast where you can hear from expats around the world and learn how you can join them.

Hi everyone, thanks for joining us today for the 27th episode of the Expat Empire Podcast. 

Before we jump into today’s interview, I want to remind you that we’re offering free 30-minute consulting calls to anyone interested in moving abroad once the pandemic situation has settled. It’s never too soon to start planning for your next big life change! Whether you’re looking to make your first move abroad, transition into life as a digital nomad, or just want someone to talk to about your moving dreams, we’re ready to help you think about the next steps in your journey. Send us a message at and let us know where you’re dreaming about moving to!

With that said, today we will be hearing from Matt Wilson. Matt is Co-founder and CEO of the travel company for people ages 21-35 Under30Experiences, and author of The Millennial Travel Guidebook. In addition to traveling around the world to lead tours for his business, Matt started going to Costa Rica in 2012 and lived in the town of Quepos until 2019. Matt hosts yoga and fitness retreats in his free time and his personal mission is to help people live more adventurous lives.

Without further ado, let’s start the conversation.


David McNeill: Hey, Matt thanks so much for joining us today on the Expat Empire Podcast.

Matt Wilson: You got it, David. Glad to be here.

David McNeill: Awesome. Well, it’d be great if you could tell us a bit about your background. Where you’re originally from, where around the world you’ve lived so far? Or at least a shortened version of that list, perhaps and where you are right about now, or at least as far as general country or direction that you’re headed?

Matt Wilson: Sure, absolutely. So in 2012, I was living in New York City, just a few years out of college, had been grinding away at a startup that I was working on, a very close friend of mine, and still my co-founder, but And I got invited on a trip to Iceland and I was like, I don’t even really know where Iceland is somewhere in the North Atlantic, I presume. And I had just been working way too many hours in front of my computer needed a little bit of change. I never had the money working on a startup to go and travel. So when the opportunity came along, I said, “Yeah, I should probably take this.” And yeah, I ended up going to Iceland and it was completely mind-blowing. I was standing there on the Eyjafjallajokull volcano with an Icelandic mountain guide and still a friend to this day, named, Siggy and just blown away watching the sunset at like 11:00 pm. And thinking, wow, wait a second, why are all my friends back home in New York City, chained to their desk and everybody just wants to go do the same thing, go to the same bar have the same conversations, and I just needed a serious change.

And so I called Jared, who I mentioned Jared, my co-founder with Under 30 CEO and I said, “Hey, why don’t we try to organize a retreat here to Iceland?” While I was there, I spent three weeks making connections. And I said, “I think we could really pull this off.” And sure enough, we had a large following on Under 30 CEO at the time, about half a million monthly readers at its peak. And we said, “All right, let’s do this.” The first trip went amazing. And the business started rolling from there. Somebody on that trip, said, “Hey, well, I have a business in Costa Rica, you should come down there.” And so I went down there for a month and checked it out. Then Jared happened to be at a random, I don’t know, some charity event at Thomas Edison’s house in New Jersey. I really don’t even remember what it was. Thomas Edison is obviously deceased now. But he said, “Hey, I met these people from Nicaragua doing microfinance work, you should go check out their projects, maybe this is an opportunity for us to get involved.

So I put on my backpack and I went from Costa Rica and Nicaragua. I really had no idea before that trip where Nicaragua even was and so I started traveling like that so, typical backpacker/digital nomad in his mid-20s. The place that I kept coming back to was Costa Rica, even though I went to Indonesia, and I’ve spent a lot of time in Bali, I’ve probably been there six or seven times over the last eight years and Thailand. I would design our Under30Experiences trips to Peru and Machu Picchu, in Colombia and Brazil to Ireland, and I was the original tour guide, and I would help make these connections.

So anyway, I traveled a whole lot but I kept coming back to Costa Rica because I just loved the place. It’s a little bit more developed whereas as opposed to Nicaragua you have a pretty consistent internet, pretty consistent power system. Once you get set up, and you kind of know what you’re doing there. There was a bus there that I really enjoyed riding and that was accessible. Things were within walking distance, the beaches were great, I was just learning how to surf and yeah, I just loved the place. I love the jungle, the energy etcetera. I spent six months in Paris, cities are not for me but Paris is one hell of a city. And yeah, I would not hesitate to go to any of these places that I’ve named, and really try to spend some time but basically from 2012 to 2019, I called Costa Rica home.

I recently moved to Austin, Texas in 2019. I picked up a wife along the way who loves to travel as well. And yes, she really felt a lot more comfortable having our child in the States. She gets her passport, instantly. I know that you’re supposed to be able to get the child’s passport when you’re a US citizen living abroad, but it’s not always that easy or as I heard, don’t expect a parade when you come back for the child so there was that. And then also just insurance, yeah, I’ve always had US health insurance through my company so we wanted the best medical care and all that for the birth of the baby. And David, I’m almost done here with this roundabout of the last decade or so. But then, of course, we ended up having a COVID baby. So in the middle of COVID or not even the middle at the very beginning when it was a little bit more scary, and they weren’t even sure if I was going to be allowed to be there for the birth of my child. Luckily, I was.

But yeah, we were living in Austin and that is where Under30Experiences was based but once all that happened, even though we had a dozen people there in office, we said, “Okay, it’s remote work time, like the rest of the world.” And there was no reason to be in a city. And so I wanted to come up to New England and be closer to family. And so now I’m looking out the window at snow, which has been an adjustment, but I am getting some little bit of skiing and some cold weather surfing in this winter, in addition to raising a child. So I know that was quite a bit, but honestly, we’re just waiting out COVID kind of quarantining, and we’ll be on to our venture soon, hopefully, child in tow.

David McNeill: Yes, exactly. Big changes it sounds like it’s been a very exciting and productive time, lots of stuff going on, good that you can be around family as well in this situation. And I think we’re all eagerly anticipating the thought of the current travel and the digital nomad and all this good stuff that’s going on right now. So I think all of the listeners are right with you on that. But it’s great to hear that you’ve made good use of the time, let’s say.

Matt Wilson: Absolutely.

David McNeill: So, it sounds like you’ve really enjoyed Costa Rica ultimately, back in 2012. I guess that was the next trip that you took after Iceland, is that right?

Matt Wilson: Yes, that was the next trip, I flew back to New York, put my mattress on the curb. I really didn’t have a lot of stuff anyway. And I said, “All right, let’s go.” And yeah, I went down to Costa Rica for a month. And as I fell in love with it there, I had some other plans and went to Nicaragua and went to Indonesia, Singapore, Dubai, I think, on that trip, but my intention was to come back to Costa Rica for the winter. Because when you just go somewhere and you say, “Ah, this is for me,” it was that feeling.

David McNeill: That’s great. And especially that you found it so early in your travels. So as you’ve made that adjustment, essentially in moving from New York to a brand new country like that, and so soon, it seems right after you, let’s say kind of, “discovered traveling,” what was that experience like for you to really pick up everything and move and essentially not look back?

Matt Wilson: It was so freeing. So I was one of the lucky people who saw The Four Hour Workweek on a bookshelf in Barnes & Noble in between my junior and senior year of college while I was in Chicago, working at a hedge fund. And I was like, “Oh, I don’t have to work in finance. Yeah, this is really interesting stuff that this guy is talking about.” So I was all in on the internet at that point. And so it was never well, I’ll say that I always thought that I had to be rich to be able to go and travel the world and that my focus would be on my career, etcetera, etcetera but when I was able to merge those two things, life got a whole lot better. And I’m barely a shell of the person I was at that time. In New York, I was very stressed out, very high-strung. And at that time, around 2010, I started practicing a little bit of yoga just to, honestly, I think it was to recover after a workout. And then I realized, oh, this is kind of relaxing. I should probably do more of this because I’m a stressed-out startup founder.

And that path really brought me to Costa Rica and to Peru and Bali and a lot of those places in my early travels, where I just saw different ways of living. People were not just in big cities and stressed out all the time. And you don’t have to go to the jungle and just practice yoga and learn how to meditate to realize this. I mean, you can go to France and realize, yeah, these people generally prioritize getting their baguettes in the morning and sitting outside at lunch and taking an hour and a half and just enjoying life. And so that became a huge thing to me. And of course, there’s a lot of when you’re surfing, you’re much more connected to nature, you’re literally riding the waves that the earth is somehow producing when you think about it is pretty wild. But yeah, I just loved it. And I said, “Okay, this feels good. I want to do more of this and I’m not going to look back.” So it was pretty easy.

David McNeill: Right. And how long had you been running Under 30 CEO up until that point and how much later after this sort of started in 2012? Or maybe that is when it started with the Under30Experiences?

Matt Wilson: Yes, so we had been running Under 30 CEO for three or four years. It was not a big business at the time, I’m sure we were doing lower six figures. But it wasn’t like we had all this money we just had normal-person salaries. And a normal person’s salary to get by in New York is a poor person’s salary, right? You’re barely scraping by, I was living in a, who knows, 500 square foot apartment with another guy. And it was a very nice apartment so we’re paying an extraordinary amount of money to be there. And so the numbers were just not really adding up. And then I realized, Oh, wait, I can backpack around the world and adopt minimalism. I don’t care about these granite countertops. I’m 25 years old I want to go see the world. And I’ll do it on the cheap and stay in hostels and stuff like that. So that was in my early days of travel. That’s what it was all about.

David McNeill: Right. And did you have a plan when you would arrive in a new city as far as maybe you had a reason for being there outside of just wanting to see the place? Maybe you had those business meetings or opportunities for investment or things like that, that you were looking into but did you have everything kind of booked and planned or did you just play it by ear for the whole month or however long that you were there?

Matt Wilson: I bet the listeners can take a guess after hearing me talk for 13 minutes. But no, I didn’t have much of a plan. It was really about going with the flow. I know it sounds cliché, but when you travel like that, you really get to stay in the places that you enjoy and meet people and say, “Oh, yeah, I do want to spend time here.” I mean, I wouldn’t have connected with my wife if I wouldn’t have said, “Okay, yeah, I’m going to stick around here for a week, because there’s a woman here who I want to get to know.” So that’s the payoff for not having booked things in advance is literally, I mean, the opportunity of a lifetime. So yeah, no, I didn’t have a lot booked but I would maybe have a general idea of where I wanted to go. I would also ask people in the hostels where I was staying, “Hey, what should I check out?” And that kind of gets a little old after a while, now I’m 35 so I try not to hang out in hostels, and have those same conversations, because once you’ve traveled for years, it’s like, okay, people are going to be complaining about Costa Rica is too expensive.

And, Oh we should have gone here or I don’t know, it’s just the same kind of conversation. Yeah, you know what I’m talking about. Along the backpacker trail, but I spent my first season up in Tamarindo which is a world-famous surf break. So that’s why I was there, where I had a friend who told me that’s where I should go, really. But then the next season, I said, “Ah, this place was a little overrun.” I think like, there’s just too many backpackers and it’s too much of a party place, and you get the drugs and all that stuff that comes in there. And I said, “Let me head to a more quiet place.” And somebody suggested the town of Quepos or Manuel Antonio where the jungle meets the beach and it is just a little bit more laid back now the surf isn’t as good. Nothing’s perfect, but the vibe of that place and the community there was really awesome. So no, to answer your original question, I didn’t have a lot booked to end, of course, I would meet locals and figure out who I needed to know but that was all just through, kind of, boots on the ground networking if you will.

David McNeill: Yeah, that makes sense. And it sounds like a good strategy, especially for long-term travel and being the most open to different experiences. I’m curious how you got into surfing originally or even just giving it a try, let alone making it an important part of your life.

Matt Wilson: Yeah, so I’ve skied since I was, I don’t know, two years old or something. My dad got me on skis early and I’d always been interested in surfing. But growing up on the East Coast, the waves in the summer are not good. And so I don’t know growing up, I just never thought you could go and get a wetsuit and surf. It wasn’t very popular 20 years ago like it’s fairly popular now to go out on a freezing cold day and go surfing. And I guess I didn’t even realize that until I was a surfer. But yes, I had been surfing a handful of times before and it was something that I wanted to get better at. But once I had the opportunity in Costa Rica, where there’s a huge surf culture, and it’s your opportunity to fit in with the locals as well, which I really appreciate and so I really tried to get away from the beaten tourist path as best as I could.

And one of my huge motivations for going to Costa Rica was to learn Spanish. Then you just have something to talk about, like I was never into American soccer or soccer. I was never into that before I started traveling but if you want to have a conversation with someone abroad, that’s one of the easiest things to sit down at a bar and chat with somebody and practice your Spanish and all that. So yeah, I’d always been interested in surfing and then I just got hooked. And I like to try to learn new skills, brain health and neurology is a big passion of mine. My grandfather and my dad both passed away from nerve degenerative diseases and so I want to keep myself really sharp. And I want to make sure that I am learning new skills and developing new muscle memory. Yeah, so I’m still on that path with surfing but trying to learn tons of other things as well.

David McNeill: Yeah, definitely. I’d love to hear a bit about your journey of learning Spanish, of course, you had those opportunities to speak about football, about surfing about all these different things with the locals there in Costa Rica. But did you have other studies or more formal training in classes or online or anything like that?

Matt Wilson: Well, I had probably what a lot of the listeners had, which was seventh, eighth, ninth and half of the 10th grade Spanish until I dropped it because I was degenerate. Now, I wasn’t really degenerate, maybe quasi degenerate, but I didn’t think that this would ever be useful in the future. Honestly, it was grammar. I really enjoyed speaking Spanish back then. But the grammar just got hard and it required to study and that wasn’t my thing when I was 15. So I really just try to learn as best as possible by speaking with people, of course, you can talk to the surfers talk to people about soccer, going on dates is a great way, just sitting at the bar, once you loosen up a little bit after a drink or two, then you start to not be so robotic about your foreign language, and you just kind of let it flow. You’re more relaxed, you’re not worried about sounding dumb, you’re not doing so much translating in your head, you’re more just speaking.

And I think it’s important for people to know not to worry, learn how to speak correctly, of course, but don’t worry so much about sounding silly or try not to be timid with it. As you can tell, nobody would describe me as shy. I would go up to people because the challenge is they want to practice their English. So especially in a lot of Latin American countries, and ones with good education systems where they do know, a fair amount of English. So they’ll want to practise English with you, which is not so much what I found in a country like Spain. Yeah, so I would just tell them straight out in Spanish that I wasn’t here in this country to speak English. Now, I would put it nicer. But I would just ask them like, “Hey, can I practice my Spanish with you?” Because I’m really trying to learn, and pretty much people would be cool with it.

Then my rule became, alright, if I… I don’t want to get this backward but if their English was better than my Spanish, I would say, “Okay, yeah, well, we can speak in English.” But eventually, I got to a level where my Spanish is now almost always better than most people in say Costa Rica’s English. And then once you get to be friends with people, it just becomes a preference. And you can be you make a friend, and sometimes they want to speak in English and that’s fine. You can’t just …I run into this with my wife, you can’t just monopolize the language. She wants to practice her English and I want to practice my Spanish. So yeah, it’s been a long journey. But of course, I did some Duolingo and some Rosetta Stone and what else? I watched a lot of sports in Spanish or any TV. I would watch the news in Spanish, just basic stuff change my phone all in Spanish. And yeah, just try to get fully immersed in the language.

David McNeill: Right. Well, after studying it in middle school and high school, and then thinking, I’m not sure if this is really going to be useful. I guess you didn’t really have thought of maybe I should try a different language now that I’m going to be living somewhere long term, you were pretty sure that you wanted to stick with Spanish and just be in that environment, which would help you to indeed improve more organically.

Matt Wilson: Yeah, I had a baseline. So it’s kind of like to switch back to the surfing example or skiing and snowboarding is a better example. So if you already ski, you should probably just go and ski and not try to learn how to snowboard because you’re going to have a lot of painful moments in the beginning of snowboarding. So, I have snowboarded, but that was just when I was bored of skiing because it wasn’t that fun for me to start over as a beginner. Now I do speak basic French, and I speak pretty good Portuñol which is just a practice for anybody who doesn’t know of changing your Spanish into Portuguese. So there’s a lot of little tricks that you can pick up on and languages are pretty similar. And so yeah, I can get around. And I’ve studied a little bit of Japanese, a little bit of Indonesian, when I go to places I really do try to speak, in Taiwan, as I can at least say thank you in Mandarin. I won’t do it on the podcast and embarrass myself. I tried to speak as much as I can.

David McNeill: Sure. And you talked about making friends and it sounds like you were successful, in the end with making some good friends locally. How was your friend group in terms of the mix between locals and foreigners? And did it change at all over the seven or so years that you’ve lived in Costa Rica?

Matt Wilson: That’s a good question. So in a country like Costa Rica, and if you live in a touristy location, right, if you want to live at one of the nicest beaches, well, then yeah. Other people have beaten you to it and so in my town, there were people from Italy and from Argentina, and of course, a lot of people from the US and Canada. But there were people from Eastern Europe, there were people from all over the world, there was a Japanese lady, right? And so, of course, most of those people would speak English and then also Spanish. But first, I made a real concerted effort just to talk to locals just to make local friends and that was it. And of course, you’re going to pick up the people who are similar to you just by, I don’t know, you just get attracted to other people who you can really relate to on that level where, okay, you grew up in a similar area. I mean, one of my close friends in Costa Rica, right, is from Los Angeles, and we had very similar lives.

And so when you’re living somewhere as an expat, yeah, expats do gravitate towards each other, because you have so much in common. And you are foreigners, as much as you like to try to fit in and all of that there are certain challenges that you’re up against being outside of your home country, and those people can relate. And I like to go out to bars and watch American football, right, because that’s what I grew up doing. So yeah, of course, I would make a bunch of friends in there and 90% of the people who were watching American football were North Americans. So surprise, surprise but yeah, I mean, I’ll say this, the collection of people that I was able to meet was very diverse. So there were North Americans who moved to Costa Rica that was working off the books for like $3 an hour in Costa Rica as bartenders and stuff like that, right? So that was very interesting to me, whether you agree with that practice or not, right? Then some of the people that I was closest to, like I had a basically a Costa Rican dad, and he worked for me, he was our caretaker and driver. And he did a ton of stuff for us but I’m still in contact, we were in contact with him yesterday. And then I had, like, surf bum friends and friends that I made from boxing and Jiu-Jitsu and other stuff that I was involved with down there. And then I was also friends with owners of the hotels and of water rafting companies. And yes, so just a very broad range of people. But where I chose to live, everyone was really into the outdoors and so that was kind of the common thread. So it was very easy for me to make friends down there.

David McNeill: Well, it sounds like you lived an extremely ideal life, let’s put it that way, tons of outdoor activities, nature, fun sports, drinks, speaking Spanish, all that good stuff. So if there’s anything about your life that wasn’t ideal, or just some challenges of living in Costa Rica, or that part of the world, or even the city that you were in, it’d be interesting to hear about that as well if there’s any stories or insights that you could share.

Matt Wilson: Yes, I’m glad that you brought this up because the grass is always greener on the other side. And it was an ideal life for me, but it was not without its challenges. I mean, where do you even begin? Okay, so things just don’t operate like they do in developed countries in the developing world. So go to the bank, and there might be a massive line or bureaucracy. I started a business in Costa Rica, we had a Costa Rican company, and that was just a mess as far as all the bureaucratic stuff, the payroll that we had to do, paying into their social security program. Like I basically needed to start carrying around a pen-like I was the 1970s, businessman to sign documents and it was just ridiculous.

And I would have loved to spend more time surfing and not so much time in accountants and lawyers’ offices in Costa Rica. So I won’t do that again. So those were some big challenges. Like I said, okay, yeah, I could get 100 megabyte Internet at my house but there were also the days when I was renting cheap places and didn’t know what was going on and I couldn’t just WhatsApp the cable guy. That actually was a huge plus because once you get to know people, everything works on WhatsApp down there, and you can text the pharmacist and the pharmacist will just bring you your stuff in a small town or they’ll send somebody on a motorcycle to deliver it to you. But before you know how all that stuff works, you’re absolutely dumbfounded and things just take forever. And eventually, I started paying somebody to be able to go and run errands for me in town because my time working on my business was really suffering because I was spending all this time waiting in line. Like, one ATM in town only dispensed $100 and there was another that spit out $400. And so on top of the bank fees, like that stuff is just pretty annoying after a while. So that’s a big challenge.

You are, of course away from your friends and family but that’s not a uniquely Costa Rican problem. I lived in rural Costa Rica so I was 2 1/2 hours away from the International Airport. That was a challenge. You could take a puddle jumper to San Jose but those things are not for the faint of heart. And they don’t fly when it’s not good weather and half the year is the rainy season. So it was strictly summertime or Costa Rican summertime, which is right now we’re recording this I said there was snow herein, in New England. So yeah, it was definitely challenging down there on a lot of different levels. That probably doesn’t even crack the surface. I guess I’ll say the medical system is very good but again, you live in a small town. So it’s just different.

So I could call the doctor on a Friday afternoon and say,” Hey, I need a prescription filled, I totally forgot about this.” Could be 4:55 pm, “Can you wait a second I’ll just come down and pick up the prescription real quick?” And the doctor says, ‘Sure, yeah, no problem,” because we just knew each other, I would probably see this guy surfing. So it’s that kind of town, or a dentist, for example, you can get a consultation for free, he’ll look at your mouth and tell you whether you have a cavity or not a cavity. And here’s how much it’ll cost. And you can’t sit down to the doctor and our dentists in the United States, they’re not going to give you the time a day without forking over a couple of $100 at least. But then if you want to go to see a specialist, you’re 2 1/2 hours to San Jose, and then you got to be doing this at a hospital. And yeah, the treatment is pretty good, but it’s not the best. So plenty of challenges I could go on for that for a while.

David McNeill: Well, it’s good to definitely see both sides. But even within the context of living in Costa Rica, where there are people that you knew, I’m assuming that were living in the big city, which I guess is San Jose. And did they have a vastly different experience on some of those fronts, especially as it relates to things like the healthcare system and that the experience around that or of course, maybe being closer indeed to the International Airport. Just curious if there’s any flavor insight that you had from talking to other people living in different parts of the country?

Matt Wilson: Yes. So Costa Rica is unique in that, well, let’s say this, I didn’t enjoy going to San Jose, because I want to live in Costa Rica because it was by the beach and by the jungle, I really avoided going to San Jose as much as possible. So one interesting thing in that country is they don’t have addresses. So everything is directional in Spanish, of course. So they’ll be like, after the banana tree, take a right and three doors up on your left or half a mile after this landmark, and it’ll be on your right go up the driveway, etcetera. So, they actually had a volunteer program where the locals mapped the entire city of San Jose, four Waze because the traffic was so bad, Waze the App owned by Google. So the locals mapped the whole city and now Waze works really well but traffic is still horrible there and so they just don’t have great infrastructure. So I didn’t want to go and get stuck in traffic jams and all that.

It’s not a great walking city, there are plenty of people who live there who are expats and there are job opportunities. It’s a pretty educated population. And so a lot of big companies, right, you might get connected. If you push Spanish, when you call Apple and you want to speak to someone in Spanish, there’s a good chance that you’ll be speaking to someone in San Jose, a lot of tech companies are set up there for those types of reasons. And so you could get transferred there if you worked at a company like that. It’s not out of the realm of possibilities. And that’s a good local experience. Yeah, it’s probably a more local experience, and yeah, you just kind of figure it out. But yes, living in rural Costa Rica was much more difficult. And that was self-imposed, of course.

David McNeill: Sure. How did you see the country and maybe specifically, the city changed over the years that you live there if you saw any meaningful changes at all?

Matt Wilson: I would say, well, things got more expensive. That’s one but inflation is an issue pretty much globally, as far as I can tell, or at least here in the United States, we may experience quite a bit of inflation, depending on how it’s measured. But it’s very, very slow down there. So it’s kind of the same old story, except the town just got a little bit more developed. Or there was a road, for example, and this was right before I moved there but there was a road to a cool little town called Dominical and that used to be a dirt road. And then they paved it, but this is like a major highway that was dirt. So they’re finally getting around to paving roads.

And I, of course, wanted to keep it a sleepy little dusty Costa Rican town, but you can’t fight change. So I think it’s up against the same things that we’re up against everywhere with change. But specifically down there, I was very active in trying to get people to conserve the natural environment, and not just put up huge hotels everywhere because that was, obviously for environmental reasons. I love that town because there were three different types of monkeys, two different types of sloths, tons of wildlife, so I felt very passionate about protecting it. And if I could leave a positive mark on a place where I spent a lot of time I really did my best while I was down there.

David McNeill: Yeah, for sure. So it sounds like even if people are considering moving there today, or of course, once all this situation settles, it’ll still be a good place for people to move to. You don’t think the things that attracted you, there in the beginning, have changed too much to make it, maybe you should steer clear or try a different city instead?

Matt Wilson: No, absolutely not. Yeah, I would say, people, yeah, check out Costa Rica. I don’t want to pump it too hard because then all my friends down there, you know they’re like, “Come on this place is overrun with gringos now.” But a lot of people who had been there for 25 years, of course, that’s what they were saying. But I wasn’t quite there long enough to see huge dramatic changes. I’ll tell everybody this, a lot of expats in places, especially in Latin America, they’re kind of, I’ll use the word again but salty “gringos” where they’re just like, kind of disgruntled, and they left the States for a reason. And so a lot of times those people loved it’s a small town. Everybody loves to complain about everything so there’s that. But I will say there are lots of positive people in the community and a lot of young people we’re very conscious and eco-friendly and we’re moving there for that reason.

David McNeill: Yeah, I can imagine so. So I’d love to switch gears a little bit and talk about your business. So you started there, I believe in Costa Rica, Under30Experiences and it sounds like it’s more focused on travel and of course, I guess people under 30. But it’d be great to hear a bit about the development of the business. You talked in the beginning about how it started but how did it really grow into being such a large organization doing tours across all different parts of the world?

Matt Wilson: Sure. So we’re open to people ages 21 to 35. And when I came back from Iceland, really what I wanted to build was a community of people who would like to travel and that focus on community is really kind of what’s important to us. And let’s see, yes, so originally, as I said, I was kind of the guide and then I would be in charge of hiring our trip leaders and finding locals that could run these trips for us and scouting out the hotels and making sure the logistics worked properly. And of course, I ran as many trips as I possibly could myself because I was having a blast. And then it just spread like wildfire because of word of mouth. And eventually, we saw ourselves for a couple of years on the Inc. 5000 List of Fastest-Growing Private Companies in America. And our philosophy was always, ‘Show people the time of their life and they will tell their friends.’  And of course, it’s way easier these days to tell your friends, because we’re all connected by social media. It’s not just what you talk about on Thanksgiving. Of course, it’s the most exciting thing they did all year most people so of course, they talked about it over the holidays and with their immediate friends and whatever. But yeah, it was quite a wild ride. And of course, we had a major hang-up with COVID but we are just waiting to get back slowly but surely. We’re opening up trips, Costa Rica is open, Peru’s going to be open very soon, country Belize is open for us. We made a big pivot this summer to focus on US national parks, where we could be appropriately socially distanced, people were staying in single tents. And yes, still getting together but doing it as safely as possible.

Then another thing that really helped our growth was having community meet-ups in these local cities. So if you went on a trip to Thailand, you could go back to the city of I don’t know, say you’re from Kansas City, you could go and meet other people who have traveled with Under30Experiences in Kansas City, and maybe you go for a happy hour with them. Maybe you do some type of cultural activity, it could be a movie night in the park, or it could be going kayaking at a local state park or who knows what going hiking. But that was the idea is to connect those people back with them together. And well, you can imagine what happens at these meet-ups is everybody’s gushing about the trip that they went on, and the energy is infectious. So maybe I shouldn’t use the word infectious during a pandemic. Anyway, we’re not doing these meet-ups right now, unfortunately, but with the vaccine and everything that 2021 and 2022 have to offer, the future is promising. And I know we’ll get back to travel, I mean, people can’t stay cooped up forever we just want to do things as safely as possible and play our role.

David McNeill: Yeah, absolutely. And I’m sure there’s even more pent-up demand than the growth. I’m sure you’ll see that through the next year or so. So I’m excited for the future of the company and seeing how it grows even further. Are there any destinations that you’re considering that are still on the bucket list as far as having a tour within the company?

Matt Wilson: Yes. Well, insider info here you go, David for the Expat Empire no, that’s okay, I will let it out of the bag. So we’re looking right now at Jordan. We’re looking, yeah, at Croatia, looking to launch a Morocco trip. Those are three off the top of my head. I think we’re going to wait for 2022 to go to Alaska. And if the Canadians ever let us Americans back in, we’re probably going to get up to Banff in that area of Canada. So yeah, we’ve got some stuff up our sleeve for sure. I mean, I can’t wait to get back out and travel. Yeah, that’s one thing.

David McNeill: Yeah, I took a trip to Jordan, and I absolutely loved it. So as I’m sure you know, there’s tons of stuff to see there, very nice people. I just absolutely loved the trip. So I’m sure that people are going to really enjoy that when the trips are still going even when they come back. Are you still going on lots of them? Or are the pulls of being a CEO, keeping, and of course, the family as well, keeping you more grounded, let’s say, in one place as opposed to the jet setter?

Matt Wilson: I haven’t been on a trip and a little while but my wife and I we’re doing yoga retreats that we were set, okay, if we want to focus on some trips, what are we going to do, and maybe something that we can do together. And so that’s what we were running for a while. Hopefully, those come back as well. My wife has 1500 hours of yoga teacher training. Yes. So I would help coordinate and put those things together. And I also love yoga so those were my main focus. But I’m hoping to get to some of these new destinations because I can proudly say I’ve been to almost every place that we sell on our website, but Jordan, Croatia, and Morocco are three places that I need to get to just so I can at least keep up with our community members and stay relevant here. As I’ve mentioned, I’m aging out myself, 35.

David McNeill: Exactly.

Matt Wilson: It’s not a hard stop. We don’t kick people out or anything. But eventually, I’ll be the creepy old guy or just the old guy. I’m not creepy.

David McNeill: Just the old guy. The old well-traveled guy.

Matt Wilson: Exactly.

David McNeill: Right on and I’d love to also hear about a book that you’ve put out called, The Millennial Travel Guidebook, and just hear your thoughts on how it all came together? What made you decide to write it, what is your goal with putting it out there is and what you hope people get out of the book ultimately?

Matt Wilson: Awesome. Well, I will say, if people have listened to this far in the interview, they’ve heard that I’m incredibly passionate about travel and the life-changing effects that it’s had on me and the trajectory of my life. But I want to pay that forward to other people. And that was the point of Under30Experiences and I love to write and I have plenty of stories, but more than travel stories, which I pepper in, of course, to keep things light and interesting. I really just wanted a guidebook for people who want to get from their couch to wherever they want to go and give them very best practices from how to save on hotels and flights and things like this, to how to get set up with the credit card miles, your credit card points, your frequent flyer miles, and best practices for staying safe while you’re abroad. Navigating visa issues for tourists, of course, and yeah, just everything people would need to know. The subtitle of the book is, Escape More, Spend Less and Make Travel a Priority in Your Life. And yeah, it’s available on Amazon would love for people to check it out. It has a lot of value. And yeah, we’d love to know what people think.

David McNeill: Cool. It sounds great. Definitely put links for your businesses for the book for, of course, your podcasts as well, everything in the show notes the show. But before we wrap up here, I’d love to know if you have any general advice for people looking to maybe move to Costa Rica, or even have a trip there to see if that’s the place for them or even just about living abroad in general. Of course, you’ve shared a lot of great advice so far. But if you have any parting thoughts or wisdom to share, it would be great.

Matt Wilson: I would say go and explore and see some stuff. And before you settle down, I guess I could use a dating analogy, right? Go and see some stuff and try out some places and see what really strikes you. There’s no reason just to say, “I’ve got to go to Costa Rica, that’s the place for me.” Now, I would encourage everybody to participate in the Slow Travel Movement if they can. So go and spend a while if you have that time off or just go on a week-long trip. I mean, that’s fine, too. That’s enough to know if you want to spend more time there, right. But I had friends down there, for example, who actually my buddy from Los Angeles, who I was saying, I don’t think he’d been to any other countries. He just said, “I want to move to Costa Rica,” granted, he had kids, and he said, “That’s what I want to do. I want to move my kids to Costa Rica, I want to give them that experience of living abroad, they’re going to learn Spanish,” etcetera, etcetera.

But he would always hear about my travels, he said, “Oh, man, I want to go there,” but at that point, it was he was kind of tied down. So yeah, I would say go and explore the world, especially if you’re young take vantage of the remote work possibilities, privileges that you have. If you don’t have them look at a way to become a freelancer or start a business. But again, I would say, take it slow. In the beginning, especially if you’re young, you’re going to want to see everything, and you can burn yourself out quickly, especially if you’re trying to make a living doing it. Because I went from a stressed-out startup founder in New York in front of my computer and then all of a sudden, I was a stressed-out backpacker, and I was going about it the wrong way. And so I would also say the last thing is to go and try to book a month-long stay if you can somewhere because then you’re going to be able to take advantage of lower rents, right. Instead of spending $200 a night on a hotel room and you can be spending much, much less on local housing for a month. And then you can figure out what’s the deal with the grocery store and then you’re going to be able to make your travel budget go further.

David McNeill: Yeah. All wonderful advice thanks for sharing that. How can our listeners find out more about you and what you’re doing?

Matt Wilson: Sure. So the best way, of course, is our website And if people want to reach out to me personally, the best place is probably Instagram, my handle is @mattwilsontv.  And yeah, I’d love to engage with people and to be part of your community, David.

David McNeill: Awesome. Thank you so much, Matt, for all of your stories and interesting, yeah, examples, anecdotes, advice from today’s conversation. I’m sure the listeners really appreciate it as well and I’ll have all those links in the show notes. Look forward to keeping in touch and stay safe, take care and see you somewhere around the world hopefully one of these days.

Matt Wilson: Sounds good, David. Thanks a lot.


Thanks to Matt for sharing his story with us. You can find the full transcript for this episode at

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As the founder of Expat Empire, David McNeill is focused on inspiring people to move abroad and showing them how to do it. David started Expat Empire because he has a genuine passion for living abroad. He left the United States in 2014 and has since lived in Tokyo, Berlin, and Porto.