Matt: Hey, everybody. It’s Matt Bowles here and our guest today is Kristin Wilson. She is a location independent business owner and a fulltime digital nomad who has lived in over 50 countries. She knew she was an entrepreneur from an early age when she won the fifth-grade spelling bee but proceeded to fail all of her career inventory tests throughout middle school. So, she decided to chart her own course, make money from lemonade stands, and pursue her passion for surfing.

By age 21, she had completed her MBA and won the National Surfing Championship in the NSSA College Division. She then went into real estate, moved to Costa Rica, and proceeded to sell tens of millions of dollars of real estate in Central America over the next six years and was featured on House Hunters International. In 2011, she founded PokerRefugees.com and she has internationally relocated over 1,000 online poker players, sports bettors, and others to 25 countries.

She’s been featured on ESPN, Bloomberg, the New York Times, and many other media outlets. Kristin runs her business remotely as she travels the world – documenting her adventures and travel tips on her popular video blog Traveling with Kristin, and she also runs the rapidly growing Facebook group, Long-term Digital Nomad Success. Kristin, welcome to the show.

Kristin: Thanks, Matt.

Matt: So, you and I met fairly recently – it was over the last month – and we met on a boat in the middle of the Mediterranean Sea.

Kristin: That’s correct. I think it was, actually, almost the last day, sadly.

Matt: It was and it was unfortunate because we started talking to each other and then we ended up and it was like 2:00 or 3:00 in the morning and we were still talking to each other. We were like, “How is it possible that we literally didn’t meet each other until the last day?”

Kristin: Yeah. I was at dinner and a mutual friend was referring to, I think, your presentation or workshop or one of your meetups and I was like, “Oh, who is that? I missed that” because, of course, the cruise was so action-packed that you couldn’t go to everything. So, you could probably only go to a small amount of it and I hadn’t even heard your name yet somehow. So, she introduced us and then, from there, we all just talked from dinner into the early morning hours. I’m really glad that we got to connect at the end.

Matt: Yeah, me too. But then by the time at the end of the conversation, we were like, “How is it possible that we haven’t been having these conversations every day on this boat?” I said, “But I definitely want to make sure that I get you on the podcast” because that one conversation I was just super impressed with so much stuff about you. So, let’s just start with this. Maybe tell us a little bit about your lifestyle, what it looks like, maybe the last year or so what your trajectory has been just so people can get an understanding of what your lifestyle actually looks like.

Kristin: Sure. So, my love for travel came at a very young age – as far back as I can remember – probably elementary school. So, I had already been traveling a lot – as much as I could – from the time I was around 18 and I could do whatever I wanted at that point, technically speaking. So, I had studied abroad in college and ended up taking a job in Costa Rica in 2005 and just basically stayed there. That was the traditional model of being an expat or an expatriate – somebody who lives in another country – and it wasn’t until I started my company, Poker Refugees, once I got a year or so into that that I realized, of course, at that point the technology had changed significantly between 2005 and 2011.

So, in 2012, I realized that I didn’t really need to stay in the same place. I had been living in Costa Rica or Nicaragua for years and I really missed traveling. I would only go places a couple times a year. So, I decided to start traveling fulltime in January 2013 and I really haven’t stopped since then. It’s very comfortable for me to live in pretty much any country and work from anywhere. It just feels like second nature. There’s been a little bit of an ebb and a flow where I’ve gone back to the U.S. and set up a bit of a home base, but I have been completely location independent again for about the past year.

So, for a couple years there – I would say 2015, 2016 – I would stay in the U.S. about 50 percent of the time and then travel for 50 percent of the time. I was just traveling so much that it didn’t really make sense to keep a home base. So, for the past year, I’ve been mostly in Europe just basically spending anywhere from a week to a month in each destination. Currently, I am based in Bulgaria.

Matt: What types of places though have you been over the last year and what types of things have you done and experienced? One of the things that I’ve been very impressed with about you as you started to tell me your itinerary or trajectory is how you really architect an epic lifestyle, right? I mean you focus on lifestyle design and you do it at a particularly high level. So, if you’re comfortable sharing some of the highlights of the things you experienced over the last year or so, I think that would be amazing.

Kristin: Sure, yeah. So, one of the things that I love about this lifestyle is just that you can basically design it how you see fit. I really cherish being able to spend a lot of quality time with friends and family because of this lifestyle. So, I end up having the opportunity to go on a lot of really fun trips but working at the same time. So, at this point, so many of my friends and, of course, my family members they know my lifestyle. They know how much I travel. So, every time somebody gets a week vacation or a two-week vacation or something is happening in the family, they invite me to go.

So, just in the past year, a friend invited me on a business trip to the Philippines. So, we traveled through the Philippines and Thailand and then she went back to work and I continued on staying in Thailand longer, went to Bali, then went to visit a friend in Australia and just kind of would bounce around because the more years that you’re in this lifestyle, the more friends you end up having everywhere in the world. So, even though if you’re traveling by yourself, you’re never really alone because you end up having connections, acquaintances, or even really good friends in almost every country that you go to or every city that you go to.

So, some of the other trips that I went on in the past year I think maybe the pace was a bit faster than it should have been because I was kind of – at the end of the year – I was kind of exhausted. But let’s see. I went to Iceland three times for different reasons like for weddings, to go with a friend, just different opportunities kept coming up. I went to St. Lucia with a friend who has a timeshare there and we got about 30 people together to rent out this big villa in St. Lucia and sailing around and things like that. I spent my birthday in Italy, which is someplace that I hadn’t been for 17 years.

So, the very first time I went out of the country was to Italy when I graduated from high school and then I ended up back there 50 countries later. So, that was really fun. I went with a friend to Positano and all along the Amalfi Coast and, of course, Rome. Let’s see, what else did I do? Some friends and I rented sailboats, catamarans, and sailed around Croatia for a week. I would also balance these social trips with trips by myself. So, I think that’s really important – which maybe we can talk about later – is how to sustain this kind of lifestyle long-term. So, it’s not like every trip is necessarily back-to-back, although some of them are.

From Italy, I went to Croatia and then, from there, on a road trip through the Balkans and then, from there, to Serbia also with friends. So, sometimes they can be strung together, but also you have to know yourself and know when you can have that ebb and flow. So, to kind of reconnect in between trips, I would go places by myself and it would be somewhere like Estonia where I went on my own, solo road trip into the forests and stayed in Tallinn and just had a really relaxing, quiet time in nature. I spent about a month in Kraków and throughout Poland.

And then when you’re ready for some fun again – well, it’s still fun either way but – then I went to Oktoberfest, for example, in Munich and got to experience that. Even though I went by myself, there were so many people I knew there from different countries around the world. So, I got to connect with different people on different days and that was really great as well. Then, I ended the year in Costa Rica in a large luxury vacation home filled with my Poker clients. So, a lot of my poker playing clients are also big on sites like YouTube and Twitch, which is the live streaming platform for online gamers.

And so sometimes when I put together houses with groups of my clients, they’ll actually invite me to come and hang out or stay there as well because we live very parallel lives and similar lifestyles. So, I spent the last six weeks of last year in Costa Rica with eight of my clients who were all working online. We’re sharing expenses, sharing a maid, sharing a private chef. I taught them surf lessons. We shot a house tour so we would be doing videos, live streaming all sorts of things. So, that’s a really fun way to balance different aspects of work and fun and collaboration together.

Then, this year has been keeping up with the pace. I started off in Las Vegas because why not? My sister lives there, actually – and then went to Japan for the ski week with snowboarding in a town called Niseko, which is on the northern island of Japan, and actually has the highest annual snowfall in the world. I really love Japan, but also broke my thumb snowboarding. So, I ended up staying in Japan for about two and a half months and then I flew from Japan to Spain to meet up with people for the Nomad cruise.

Then, after that continued traveling with everybody throughout Greece and then, from Athens, flew to Bulgaria. I have a lot, of course, still planned for the rest of the year because opportunities are always coming up and there are so many Digital Nomad events, conferences, co-living situations, co-work-cations if you will. So, it’s going to be a really exciting year and I’m looking forward to, of course, always the next destination and the next Nomad cruise as well. So, that is kind of a summary of the last year.

Matt: And right now, I am in Valencia, Spain and you are in Bulgaria?

Kristin: Mm-hmm.

Matt: So, I’m just sort of positioning us here for the listeners. I’m excited for the year too and, hopefully, our paths will cross again as they did last month. I’m sure we will see each other at some point for the rest of the year. Maybe, actually, let’s take this opportunity – since you just gave that overview – for talking a little bit about that because I want to get into the entrepreneurship stuff with you as well, but maybe right now we could talk a little bit about the sustainability stuff because I know your presentation on the Nomad cruise was about how to sustain this lifestyle long-term.

I think that’s a really, really important topic for folks – even for folks that are newer or just getting into this scene or the lifestyle or they’re considering the lifestyle. One of the things that I think people’s mind initially goes to is, “Well, what’s the long-term prospect for this kind of thing?” People who are already into it come across different sorts of challenges in different ways. So, I think the way that you’ve put together some of your concepts for sustaining this kind of lifestyle that you just described are really, really important. So, maybe we should just go into that right now. Can you start talking about what some of those sustainability pillars are for long-term nomad life?

Kristin: Sure. So, this is definitely – as you mentioned – something that is really important for people who are already in the lifestyle, and who are just starting, and who haven’t started yet because it gives them an idea of what they can expect. I know that it’s relevant for people who’ve been in it for five or 10 years because I’ve been living abroad for over 13 years. I know that my friends and peers and other people who I’ve been around for the same amount of time are all still struggling with the same things.

So, when I was preparing for my workshop, I was thinking really far back into the nature of humans and humanity and our genetics themselves because no matter how fast technology changes or how modern we think we are in our lifestyle now, we still aren’t that far removed from human history, in general. I mean it’s only been a few decades really that all of this innovation has been happening at such a fast rate. So, there’s just right now – not only for digital nomads but for just people on the planet in general – there’s a pretty big disconnect between what we need to be healthy and happy and our modern day reality.

Of course, that’s because of technology. So, technology makes our lives better, but also causes some challenges that need to be addressed – so things like being inactive from sitting at the computer all day. People are struggling with a lot of mental health issues, anxiety, depression, and just burnout because we’re using our brains for our work instead of our physical bodies, which is what it has been like for such a long time.

So, I was going back and looking at that disconnect and then how it’s expanded when you get to the digital nomad realm because not only do we have to deal with the same things that everybody else is dealing with who’s alive right now, but it’s also magnified because we are at the beginning of the adoption. We’re early adopters of this cycle and there’s not a lot of support. There are not very many companies or products or solutions for the specific problems that we have. So, we are making it up as we go along. We’re defining success for ourselves. We’re creating solutions for our own issues on the way.

There’s just not really an infrastructure built for people in this lifestyle. So, I think that is a really important point before even getting into the reasons why people fail and then, of course, how they can succeed because we can’t look at that until we see what the challenges and the problems are. So, the first thing is just to really give ourselves a break because we are the first ones to be figuring this out kind of on our own terms. And then the things that will help us in the future, that’s all kind of catching up to where we are now. So, the main factors that I identified of where things go wrong – and sometimes this happens before it even starts – is there are basically four things – so, a lack of money.

There’s cultural inflexibility, as I call it, so just a problem adapting to new cultures. There’s the loneliness factor which, of course, is something with which people also struggle in their life before becoming digital nomads. And then there’s a lack of clarity. So, for lack of funds, for example, you’ve seen probably on the internet or you’ve maybe heard people talking about how they just said, “F it.” I don’t know if we can cuss on your podcast, but they just bought a one-way ticket somewhere, quit their jobs. You know you’ve heard of that kind of story, right?

Matt: Yeah, of course. Yes, Kristin, you’re more than welcome to cuss on my podcast.

Kristin: Okay. So, they’re like, “Fuck it. I’m leaving this job. I hate it. I’m going to take a one-way ticket to Bali or Thailand and I’m going to figure it out.” So many people do that and that’s the first step on your way to failure in sustainability in this lifestyle – so running out of money, cultural inflexibility. People who kind of live in a bubble and never really get integrated with the community for whatever reason. It could even be that they’re not spending enough time in each of the places that they’re going to.

They’re just going through their bucket list checking things off and partying with other digital nomads or backpackers or things like that and they don’t even realize for months and sometimes years that they never really connected with the places that they were because they were going too fast and then, loneliness. I think loneliness is a mindset and you can feel lonely even if you have a family and a partner and everything looks good on paper. You can still feel lonely, but this is exacerbated when you’re traveling around the world by yourself. With a lack of clarity, it’s really tied in with the lack of funds.

When you have people who want to become digital nomads, but they think they know in their brain why they want to do it, but they don’t actually have a connection between travel and what one of my favorite authors, Cal Newport, calls a unifying career mission, for example. So, they don’t have their “why” very clear as to why they’re doing this. Sometimes I think people subconsciously think that everything’s going to be better when they travel because they’re running away from problems and they’re going to get a new perspective and it’s going to be better once X, Y, and Z happen.

Typically, traveling causes or creates the opportunity or the space for more problems to come into play. So, that’s a whole other story in itself. So, there’s just a lack of clarity on why they’re doing it, also, where they’re going, how they’re going to fund it, how long they’re going to fund it. So, what ends up happening is after a certain amount of time goes by – and it’s different for everybody – they just start to realize that maybe they haven’t formed deep connections. Maybe they didn’t even expect to, but they didn’t know that was missing until after the fact and they’re struggling with paying their bills.

So, they’re stuck in a certain number of destinations that they can afford. They don’t know where they’re going next. People just end up being really ungrounded and they start questioning why they’re doing this. And this is where you see on YouTube and on social media now because it’s been a few years that this lifestyle has been more mainstream. You start seeing headlines like “Being a digital nomad is a scam” or “It’s not sustainable” or all sorts of other negative headlines and things like that. I think that’s because of the reasons that I mentioned.

So, people don’t really know why they’re there or where they’re going and it’s this kind of either quarter-life crisis or midlife crisis that starts showing back up in the digital nomad lifestyle itself. So, those are some of the ways that things can go wrong, but then it’s also, of course, important to talk about the sustainable part. So, to kind of counteract those things, I think identifying why you’re doing that is super important and that’s in your business and also in your life especially if you’re ready to take your life outside of your old life – so outside of your comfort zone, outside of your hometown, outside of your support circle of friends and family – and go out into the world by yourself.

So, besides establishing why you’re doing it and then creating a logistical plan to back it up and be successful long-term, you also have to have a job. You have to have proven income streams and –if you don’t have your own business or an employer that lets you work remotely – then you need to have a lot of diversified revenue streams so that you can support yourself if you lose some of them. This is another thing that people do is they go somewhere and then they think they’re going to figure it out once they get there, but they don’t take into consideration how much work it’s going to be.

One of the things – actually the main thing – that all of my clients have had in common – whether they were poker players or corporate executives or digital nomads or any other type of employee or retiree – is they all had jobs or they all had reliable revenue sources that they knew exactly how much money they were going to be making every month.

So, that’s something that especially the younger digital nomads don’t necessarily have. And then another thing that came up – because I actually talked to and interviewed a lot of my friends and clients who had been abroad for five, ten, 15 years about what they felt like made them the most successful and helped them to keep going for so many years – and being open-minded and laid back and kind of rolling with the punches was one of the main things. I think that counteracts the kind of cultural inflexibility.

So, when you are living in a foreign country to just be able to be more flexible and more patient with the way things work and more accepting of the differences, especially if you’re establishing a business, opening a bank account, working with local people, things like that. And then another huge thing was finding your own community or tribe or support system, which really counteracts that point I talked about for loneliness.

So, so many of the people – everybody – miss their friends, miss their families, and the way that they were able to keep going and keep traveling without just being really homesick forever is to either create their own family or find a like-minded community and create a support system wherever they go. That can be done in a few different ways and I think the most common ways are to slow travel so that you’re spending three months, six months, one year, two years or more in any given destination so that you can really meet people. And then also digitally, there are so many groups now, communities, retreats, conferences, and ways to meet other digital nomads.

So, if you’re not going to meet regular people in the place that you’re living, you now have the opportunity to meet other transient people so that you can kind of create a global network of friends and never really feel like you’re alone and not supported. So, of course, my workshop was 90 minutes long.

So, that’s a really small summary of kind of the problems and the solutions, but the main formula for success is to just have a really clear, defining mission for why you’re going to go location independent, having a good plan, having reliable funding, having a good self-awareness and giving yourself space to reflect on what you’re doing and why, again checking in with yourself, having a flexible, positive mindset, having a community, and then, of course, also putting in the work. So, you have to work a lot unless you have some independent income streams that you don’t need to maintain in some way. But a lot of people don’t work enough. So, that would be the other tip.

I think if you have those six things covered and you revisit them on a regular basis, then you can just continue as long as you want and also keeping in mind that you don’t have to do it forever. You can always go back home or wherever home is. You can always choose to make a place in your home and stay there. You don’t have to be perpetually traveling as a digital nomad. You can do it while you’re enjoying it. But if you’re following this sort of success map and you are recognizing warning signs for when you’re not happy and when things aren’t working, you can say, “Hey, let me take a break. Let me reconsider my lifestyle.”

Maybe it’s time to change it up a little bit for a while because you can always go back home and you could always decide to start traveling again. So, it’s just kind of knowing yourself and knowing your limits and recognizing when things change, proactively trying to resolve any problems, and just basically repeating that throughout. There’s no – like you were saying – no one end game for everybody. This lifestyle is evolving all the time. So, there’s not one outcome that you have to achieve in the end. It’s one of those like the journey is the destination things. So, just as long as you’re enjoying the journey, just keep doing it and understand what you can change and what you can’t.

I think you can definitely find an equal or superior level of happiness than you can in the regular kind of more constricted lifestyle that we are brought up to believe that we have to have. So, it’s just being able to have the choices and the freedom that we have and then also appreciate it and keep it in perspective so that freedom doesn’t become a trap in the lifestyle itself if that makes sense.

Matt: Definitely. I think those are really important tips. In my own digital nomad journey – and as you know – I have been fulltime location independent, outside of the United States, since 2013 as well. I’ve lived in over 45 countries just in the last five years. I discovered some of those different points that you made kind of as I went along, right? I didn’t start my journey by saying, “Okay, today I’m going to be a digital nomad and ready, set, go.”

Exactly, it sort of evolved. I had a vision for the concept of location independence from the beginning because I read Four Hour Workweek by Tim Ferriss in 2007 when it came out and that was at a transitionary moment for me in my life when I had just been fired from my job. I had decided I was going to start a business and figure that out and go the entrepreneurial route. I read the book and I was like, “Okay, I’m building a business with a location independent infrastructure and that’s what I’m going to do.” I worked really hard to do that, but I didn’t utilize the location independence for long-term, international, itinerant stuff.

I was basically based in Los Angeles because I like Los Angeles and I was in a relationship with someone in Los Angeles and that was a cool city. I didn’t have any business purposes there per se because I built a location independent business. So, I wasn’t leveraging the location independence to do the international stuff, but I was seeing the value in that freedom of mobility. I could just go home for the holidays and spend a month with my parents if I wanted. I didn’t have any geographic restrictions on me. But to your point about the building up the stream of income first, I definitely had done that.

I had built that up and I had a functioning location independent business. Then, it was just my relationship partner at the time needed to leave the country. She was doing a Ph.D. at UCLA at the time and she needed to go do her dissertation research in Egypt. So, she’s like, “I need to go to Cairo for the year.” I was like, “Cool. Let’s roll.” So, we just went to Egypt for the year. At the time, we put all our stuff in storage and got rid of all our stuff. I was just thinking, “Oh, maybe we’ll come back after the year to LA. So, it will be just a year away.” But then the next year, she had to write her dissertation and she had a year to do that.

We were like, “Well, we don’t really need to go back to LA for you to do that. Why don’t we just pick our top five places in the world that we’d love to live and rent Airbnbs for two months at a time, you know?” We were like, “Cool.” So, then we went and did that and then – all of a sudden – we’re in Rio de Janeiro and Cape Town, South Africa, and all these super cool places, right? So, it just sort of evolved in this way where it wasn’t like, “Okay, now we’re going to be digital nomads.” It was based on some of her stuff and then we were incorporating the lifestyle design.

Then eventually she and I broke up and I decided that I wanted to continue traveling, but I had the main challenge that I saw before me at that time was what you were talking about with the social isolation and the loneliness, right? Because even though I was traveling the world with one other person, we were moving around and we were not effectively and meaningfully plugging into broader social communities in those areas. To be honest, I wasn’t even aware that those social communities may have existed or how to even begin doing that.

So, then in 2016 – after we broke up – I joined a program called Remote Year, which is one of now many businesses that are coming into this space to cater to these types of needs and these types of voids and these types of challenges, right? So, this was a program where you sign up for a full year and you go and travel the world with somewhere between 30 and 60 people who all have remote jobs of some kind. They could be employees that work remotely, they could be business owners, they could be freelancers or whatever else, but they have a location independent income stream and the company Remote Year takes the entire group.

You travel together for the whole year with the same people and you live in a different city each month for 12 months and they take care of all the accommodations and the co-working space and 24/7 access to WiFi – which they have technicians to make sure it’s working and everything – and they take care of all your international airfare. So, they take all that logistical stuff and handle that for you. But even more importantly, the most important thing to me – the value that I got out of that experience the most – was the community because I was with the same people for one year and we saw the world together. We explored the world together.

They were all interesting people, passionate about travel, had been able to somehow create a location independent lifestyle for themselves and that was just a really amazing experience. So, when I had that, I realized like, “Wow, there are ways to really solve for any of these problems that you might feel.” Now there are a number of companies in the space that are creating really cool, interesting opportunities for digital nomads to solve for these problems. So, when people are thinking about this lifestyle, “Should I get into it? Can I sustain it? Is it long-term?”

I think just having a vision of what that ecosystem currently look like with programs like Remote Year. I’ve also done some travel with other programs too. There’s a program called Hacker Paradise that I was in Vietnam with for a month earlier this year. I’m going to go back and I’m going to go to Japan and Korea with them later this year. It’s another example of another program. But the other thing is I went to Chiang Mai for seven weeks and I plugged into the community that’s there and that’s an amazingly well-organized social community that you could just show up and walk in and be included in that. But in my early part of my journey, I had no idea that any of that stuff existed, you know?

Kristin: Yeah. Oh, there’s so much to unpack there because I first heard about Remote Year in 2015 I think when they were doing their first one and I thought, “This is going to solve so many problems” because it solves the problem of just having to plan your own travel, which is so time-consuming and definitely not the best use of almost anyone’s time. I plan travel for a living for other people. So, when I’m planning it for myself, it’s just basically taking away from my income.

So, it’s so great to just show up somewhere – whether it’s one year or one month – and WiFi Tribe or one of the places similar to Remote Year. As you mentioned, there are a lot of companies now because they handle – Basically, you get an instant group of friends. You don’t have to worry about internet and you don’t have to worry about where you’re going to live. It’s typically more affordable than it would be if you were doing short-term travel by yourself. I mean Remote Year not as much, but I usually end up spending more money if I’m just hotel hopping and Airbnb hopping, rather than if I ’m staying at one co-living place at a time.

I didn’t do Remote Year because I wasn’t ready to commit to the whole year because I had other things going on and I had already been in the lifestyle for a while, but I have now stayed at Rome, co-living in Japan, and I’ve joined the WiFi Tribe. So, I’m planning on doing a couple of those chapters. I’ve looked at Hacker Paradise and some of the other ones. So, I think that’s a really exciting thing on the horizon.

Well, it’s here now, but it’s just going to grow because I remember seeing back in the old days when Nomad – It wasn’t even Nomad List yet. It was the Nomad List Slack Forum from maybe 2013 or something like that and I remember somebody posted in there, “How do we solve housing for digital nomads because there are so many problems with that because you basically only, in the world, have a market of houses or properties for sale for long-term rent, sublets, or vacation rentals?” Digital nomads don’t really fit into any of those categories or were looking for midterm, affordable rent and we’re not going places for a week vacation paying a premium, but we don’t necessarily want to sign a one-year lease.

So, it’s really cool to see how this co-living, co-working dynamic has solved the housing problem in a lot of ways, but also solved the related problems with the lifestyle like loneliness and things like that. If we get a critical mass, which is definitely happening I think in the next couple years. I mean if there are millions, hundreds of millions of people living a location independent lifestyle – whether they’re in their home base or traveling around – I think we can have that global network and that global community that doesn’t necessarily have roots in any one place.

It will just be such a big community that it won’t be any different from being a citizen of a country or a resident in a specific town because it will just be so well-connected and so big. Don’t you agree?

Matt: I totally agree. The more you travel around and the more of those types of programs and experiences that you have and the events that you participate in and things like that, it really is amazing like that Nomad cruise that we just went on, right? There were 250 digital nomads. I think the next one they’re going to try for a lot more than that and you just show up and it’s like everybody wants to meet you. They want to get to know you. They want to hang out with you – whether it’s to have fun with you and laugh and go dancing and do stuff – or whether it’s to talk about business ideas and they’re interested in what you’re doing and can help you with stuff or whatever it may be.

But you have people that want to engage with you, get to know you on a meaningful level, and then go explore cool places with you. That is also what I am experiencing when I go and plug into these different places that I go. So, now the way I’m structuring my lifestyle is, “I’m going to go to this city here and this city there and this city there” but I’m kind of doing it mostly – I do some of the stuff where it’s like a few friends.

We’ll go and do this cool stuff like we’re going to go through the wine country in France and do some cool stuff like that but, for the most part, when I’m doing longer term stuff, I’m doing it as part of these live-work communities. So, I know that as soon as I land in a city that I’ve never been to, I’m immediately going to have a group of people. They know I’m coming. They want to meet me. They want to hang out with me. They want to explore the city with me. You just have solved for that social isolation problem. I mean it’s amazing.

Kristin: Yeah. And another thing for your listeners who haven’t experienced this type of lifestyle yet or even digital nomads who are still on their own and haven’t dipped their toe into this co-living is it’s so inclusive like you were saying. I don’t know if – even in the community – we’ve really dove into this topic so much because if you think of when you were living in LA or when you’re living in your hometown, you do get in a routine and you do end up with kind of a fixed social circle. You have to make a real effort to meet new people. If you’re living in America, who do you hang out with?

It’s like your friends maybe from school, from college, your coworkers, people you meet maybe at the gym, or if you’re a parent maybe with other parents – you have kids the same age – but it’s a little bit limited. People aren’t necessarily in the disposition and the mindset to just talk to strangers, to strike up a conversation with people, and then dive so deep so fast. You go into a Starbucks, no one’s talking to each other. Even when I go back to the States, I kind of get back into that routine and have my handful of friends or I see them at yoga class or whatever. But my friend group only expands if you really make an effort to maybe meet mutual friends of other friends or go to meetup groups and things like that.

It does tend to stay pretty surface level like, “Oh, so, what do you do for work?” because that’s the first question everyone always asks. It just kind of stays in that zone, whereas in this co-living, digital nomad, location independent community, it’s unprecedented I think to have a community of complete strangers that just right off the bat have an understanding. They don’t care how old you are. They don’t care what you look like. They don’t care how much money you have. They don’t care what your job is. They don’t care what color your skin is. They literally don’t care. Can you think of another place or another situation in life where that happens?

Matt: Yeah, I totally agree. It’s been really amazing for me to experience that and it’s been really exciting to see the growth in that digital nomad ecosystem and just the places you can go around the world and plug into those communities and how interconnected things are today. But I want to also, Kristin, transition now a little bit and talk about your entrepreneurial journey.

The first thing maybe where we could start as you tell your story that stood out to me – because I related to it from my own entrepreneurial journey – is that there are multiple points in your trajectory and your path where you had to pivot or change course either because something happened and befell you and blocked the path that you were on and you needed to or because an opportunity arose and you saw a different way to go about doing something.

You seized upon that opportunity. I think that one of the most important lessons for entrepreneurs or for people who want to get into that game or change something in their life, I feel like there are a lot of times a lot of inertia or they feel like they have to stay on the same path that they’re on. One of the things that certainly happened in my life is that I’ve had to just – when something befalls you or stops your path – you just have to figure out a way to pivot and to go a different direction or to see an opportunity and to take it.

So, I think you really embody that spirit pretty well. I would love for you to just maybe talk a little bit about your journey. Maybe start us back in your college or even pre-college period and maybe start talking about your passion for surfing and talk a little bit about that and then you could go from there and where that led you on your journey.

Kristin: Yeah. So, I started surfing in high school and I didn’t know how much I would love it. It kind of became my life. And if anyone surfs, you know what I mean. It’s not just a sport or an activity that you do, but it kind of becomes your identity. There’s this whole subculture around surfing. So, I got really serious about that and started competing and everything but – at the same time – I was always really good at school and always got good grades. So, I was very dedicated to my coursework in college and getting straight As and things like that.

But the one thing that I could never shake throughout that time was the anxiety and angst around choosing a major because I feel like in the U.S. – at least at that time and probably still today – there’s this finality to picking a major. I didn’t know at 16, 17, 18 what I wanted to do with the rest of my life and I think it’s funny – now that I’m in my mid-30s – and I still hear people my dad’s age and older who are talking about what are they going to do when they grow up? So, I think that’s something that everyone can relate to. But for a teenager, you don’t know that yet. You just know that soon you’re going to graduate and you have to either get a job or go to college.

Pretty much as soon as you get to college, you need to have an idea of the type of track that you want to go with. So, in college, I changed my major so many times that – by the time I graduated – I had enough credits for two separate college degrees. So, I started college in, I think, eleventh-grade doing dual enrollment classes. I had about a year of college done before I even got to where I studied, which was UCF Central Florida in Orlando.

Yeah, I ended up with enough credits for two college degrees and only one major and no minors. So, that can just kind of set the stage for all of the different directions that I was going in. That was kind of going to be foreshadowing the different directions that my career would go in, right?

Matt: Yeah. I totally relate to that, by the way, because in college I was just taking all of these different electives that I was interested in and then they were like, “You have to pick a major.” I was like, “But I don’t want to. I just want to keep picking interesting classes and taking them all.”

Kristin: Yeah. There should be some other major that that would work. I guess there are liberal arts or liberal studies, but that just seems like the major who can’t decide. Also, at this point, whatever major you choose you don’t even really need to work in that specific industry. To put things in context back then, I didn’t have a laptop. I didn’t have a laptop until grad school. So, it’s a lot different for the kids that are in school today because they can even start their side hustle during high school or college with the internet, but we didn’t necessarily have that option.

So, even when I graduated, I finally majored in International Business and studied abroad a couple times and really got a feel for what it was like to live abroad and fell in love with just the whole concept of it. So, I’ve been living in foreign countries since age 20. So, it’s been about almost 15 years total I think. But I still didn’t know what I wanted to do for work. I knew I loved traveling, graduated with honors, whatever. So, instead of getting a job, I went to grad school.

So, it turned out to be a pretty good option because getting an MBA – even though I did it in a nine-month period and I think it would have been ideal to go get some work experience, come back, and take my time with it – but I do think that it helped give me the tools to think strategically and differently than an undergraduate degree does. So, if anyone’s thinking about that, then that was something helpful. Again, I kept hitting these walls. So, graduating from college I didn’t know what I wanted to do.

Then graduating from grad school a year later, I still didn’t know what I wanted to do. Something really kind of life-altering, I guess, happened in between when I started grad school and I finished grad school, which pretty much changed the whole trajectory for my life as it relates to surfing and my career. So, I actually have never said this publicly, but I burned out. You know that career burnout that people tend to get in their 30s or 40s?

Matt: Yeah.

Kristin: I got that kind of burnout at 21 in grad school where I was running on such little fuel. I was burning the candle at both ends, all that good stuff, with an internship. I was a graduate assistant. I was working part-time, going to school full time, and just probably drinking too much coffee.

I was sponsored by an energy drink company, so I was drinking the sugar free equivalent of Red Bull every day and I ended up having a grand mal seizure in an airport – in the Atlanta airport, actually – on my way to Costa Rica for a charity event and just woke up on the floor of the airport with all of these people around me and, long story short, actually, I didn’t even know what happened. They still put me on the plane in a wheelchair. It wasn’t until I got back from that weekend that I turned on my cell phone – because that’s when we had the Nokia phones or the Razor flip phones.

So, I powered on my cell phone to call my brother and tell him what happened and somebody in the airport recognized me and came up to me, interrupted the phone call I was having with my brother to tell him what happened. They were like, “Oh, you’re the girl who has epilepsy. How are you doing?” I was like, “Excuse me, what? I thought I just passed out or something and they’re like, “No.” He’s like, “I’m a doctor. I was going to a conference. I came through the airport and you fell on top of me basically.”

Now, he was at the airport in the same terminal four days later going on vacation with his wife and he saw me. So, it was a complete zero percent chance that happened, but that is the only reason why I even knew I had a seizure. So, that completely changed everything for me because it put health in perspective and it showed the dangers of what I was preparing for mentally, which were these 60 to 80 hour weeks in corporate America, right?

Matt: Yeah.

Kristin: So, that kind of changed everything because after going through testing and everything, they did diagnose me with epilepsy and they took my driver’s license away. So, I’m 21 in grad school, with no driver’s license. They told me I couldn’t surf for six months and it was just the worst. It was the worst time. It was the worst feeling. I felt completely helpless and I was so lost and I didn’t know what to do. It wasn’t until years later that now, I think if that didn’t happen I probably would have continued with the status quo and who knows? Who knows what would have happened? I don’t know.

So, actually, I would say that pretty much ended my surfing career because I won the Eastern Championship and the National Championship in 2004 and then I had the seizure. Actually, I think it was the same year. I think it was a few months later. Yeah, so that summer I won everything and then by October, I couldn’t even surf anymore. So, when I graduated from grad school, I was pretty depressed. I didn’t know what I was going to do and I was really depressed with the options that were available to me because I didn’t graduate from an Ivy League school. So, I didn’t have that type of career placement and just by random chance, somebody tracked me down.

So, it was when I was in high school, I was a lifeguard and one of the guys I worked with his older brother had moved to Costa Rica to start some real estate companies and – through word of mouth – he heard or maybe – Did I have Facebook yet? I didn’t even have Facebook at that time. I don’t know. Somehow he found out that I studied abroad in Costa Rica and spoke Spanish and he reached out to me and offered me a job to help me open an office for a Coldwell Banker franchise in a little town called Nosara in Costa Rica.

So, that is what started my journey of living in Costa Rica. Of course, I thought I would only do that for – I was still brainwashed. I thought, “I’ll just do this for a year and then go back to my real life in America.”

Matt: Was that your first experience with real estate? He just offered you that job and then you were like, “Oh, real estate. I never thought about that before, but it sounds like a good plan to go to Costa Rica and learn about real estate.”

Kristin: Yeah. And you know I didn’t even really think it was that good of an idea. I wasn’t interested in real estate. It had never crossed my mind before, but this proved to be a good lesson as well because I developed a skillset in something that I didn’t necessarily love and I didn’t have a passion for. But it helped me set a foundation for the company that I was going to launch seven years later that I hadn’t invented yet or hadn’t had that idea yet.

So, the only reason I took the job was basically because I knew I loved Costa Rica and I knew I loved traveling and I had had this seizure and physical burnout and my family agreed that I probably needed to calm down and maybe go somewhere that wasn’t such a stressful environment. So, that was really nice to be able to live there for a few years and live on the beach and go surfing. I actually was able to get my license back and go surfing again and do yoga. I took a lot of side jobs like teaching surf lessons and working at a bar and restaurant and things like that to get by until the real estate took off.

Yeah, so that kind of snowballed through the years and brought me to Nicaragua and then back to Costa Rica. But during that whole time, as you said, even though from the outside my life looked perfect – like I was making six figures, I was living in paradise – I just still didn’t love what I was doing. So, I changed companies, I changed countries, I started working for myself outside of a company just on my own. It was kind of a rollercoaster. In 2009, I was kind of at my wit’s end. I was like, “I hate this. I don’t want to do it anymore, but I like my life, but I don’t like my job” and I ended up going to Bali for a month with no money.

I was like, “I’m just going to figure things out and just think about it.” That was one of the best months of my life and that put things into perspective that, “You don’t need to have a lot of money to experience this feeling of bliss.” So, on one hand, I was broke in Bali kind of searching for meaning and then I had just come from the real estate industry where people who were 40 years older than me – who had saved money their entire lives and had millions of dollars in the bank – were moving to Costa Rica to replicate the life that I had as a 22-year-old with no money or it would come and go.

So, that also stuck in my mind because I thought, “All these people are waiting decades and saving all of this money to do something that they could do with way less money.” So, it made me realize you don’t have to be rich to travel and you don’t have to be rich to live abroad.

Matt: Definitely and it’s usually most of the places in the world if you’re coming from the United States or if you’re coming from the United Kingdom or if you’re coming from Australia or if you’re coming from any of those types of countries, most places in the world are significantly less expensive than the United States – both in terms of accommodations and in terms of food and in terms of pretty much everything. And so you can really architect an amazing international lifestyle where you can even travel around pretty frequently and be pretty itinerant and – even with all of your international airfare included – you can usually do it in a way that is lower than the cost of living in a major city in the United States.

Kristin: Yeah. And that became just normal to me. So, people would always say like, “Oh, when are you coming back and how are you doing this?” I was just like, “This is my life. I’m not going back anywhere because my life is wherever I am. It’s not separate. It doesn’t matter where I am geographically.” That was around the same time the Four Hour Work Week came out, which was 2007, which I completely, randomly saw in a Barnes and Nobel during a one-week trip to the U.S. to visit my family. I just saw it in the back corner of a Barnes and Nobel on the UCF campus and I just saw the cover of it out of the corner of my eye.

I’m like, “That looks interesting” and I picked it up and I had no idea it would become this cult classic that I wish, at the time of reading that, that I took more into consideration the principles that Tim Ferriss was talking about because I definitely identified with everything that he was talking about, but I did not have an automated income. My income was very much me in person showing properties, making deals happen, getting listings, and just very physical work that I was very tied to that location.

So, this is something that I struggled with for years because maybe there is a possibility that I could have thought of some other ideas of what to do, but I was so stuck in the habit of real estate that – even after this kind of epiphany moment that I had in Bali – I still ended up coming back to Costa Rica and then taking another job in real estate because it was what I knew. It was a comfort zone. So, even though I was traveling to all these different countries, living out of my comfort zone, I was still stuck somehow in the comfort zone of my career.

So, that was the fourth time I think I reinvented myself within the same industry and for another year or year and a half – I think it was like another year – then I decided, “Okay, I have to actually make some moves.” At that point, it had been about six, seven years. So, that’s when I decided, “I’m done.”

Matt: Yeah. Now tell me the story, though, about it because you’ve never actually told me the story about how you got on House Hunters International and who the clients were that you were there with and how that whole thing played out. What was that like?

Kristin: So, I guess House Hunters is still a pretty popular show and I really loved it because it was basically mimicking my life. So, it resonated with me a lot because I was watching other people doing the same thing in different countries around the world and I just thought, “Why don’t I try to get on the show?” I think they were looking for people. So, I sent in a video which is – actually, it’s still on Vimeo – which is really embarrassing.

I think I need to remove it – just auditioning for the show and they really liked it and we actually went through a big casting process where I had to submit the profiles of a lot of different clients because they have so many different demographic requirements for the buyers, which a lot of people probably don’t know. So, we knew we were going to do the show. We just didn’t know who it would be. And so what they do is a deal that has already happened and they recreate it. So, in the end, they were real estate clients of my firm, but they weren’t my clients.

They were my friend’s clients, but they were friends of mine and, actually, they were my clients for rentals, but the house that they bought, they didn’t buy through me and they bought five properties. So, we recreated that and the client was a Lord – so a royal basically – from Denmark. So, here we had Danish royalty and his fiancé who was a model from Brazil. So, they were just this beautiful couple also living kind of as digital nomads because he was working in finance and she could model from anywhere. So, that was 2011.

So, it was still way before people were really talking about digital nomads. That was really fun. It still runs and people will contact me on Facebook and say, “Hey, I saw your House Hunters episode” and they asked me to do it a couple more times. But, to be honest, they don’t really pay you. I think I got, I don’t know, it was not that much – maybe a few hundred dollars – and it took months of planning and then three or four days to film.

So, even though it was fun, I felt like it was a kind of closure for my career in real estate that I could have this little piece of my history there to just kind of bring everything together and I really wanted to show an authentic perspective of what it was like to buy real estate in that area because I felt like a lot of the stuff on TV was a little bit fake. So, I really wanted to bring all my experience into this 20 minute TV show. So, I’m glad I did it.

Matt: Yeah, that’s amazing. Well, you’ll have to let me know where I can watch it because I definitely want to see that episode and if there happens to be a link or something like that, we can definitely share it in the show notes because I’m sure that would be amazing. But yeah, that’s incredible to leave that and now you have that kind of historical, archival piece that will be there about you and your contributions in that period of your life, which is really amazing.

So, then let’s talk about from there, the transition. How did Poker Refugees come about and how did you see the opportunity for it? Maybe you could talk a little bit about what it is and the business model that you designed there.

Kristin: So, this is, I think, an important takeaway for people who might be involved in a lot of different things. They might have a lot of different interests and maybe they’re feeling a little bit lost and they’re just not sure how or when things are going to come together. So, I had made a plan that I was going to exit the real estate industry, move back to the U.S. in July of 2011. This was my New Year’s resolution. It’s like, “Okay, I’m just going to work another six months or so and then consciously plan a move back to the U.S., change into a different career” because I just felt like I had been doing the same thing for so long.

So, by April something happened, which is called the Poker Black Friday, which is where the U.S. Department of Justice shut down or seized a lot of the websites of online gaming operators that were based offshore, but offering services to customers in the United States. So, this created a really big problem for many people because I think there were millions – like 11 or 15 million U.S. customers – on these poker sites and they got cut off from the sites. Of course, a lot of them were recreational players, but a good amount of them were professionals.

And the only reason I knew that this kind of economy existed – this online poker economy – is because a lot of those sites, or most of them, were based in Costa Rica for whatever reason – maybe taxes or good regulations or whatever. So, I knew a lot of the people who worked in those companies and I was aware of the dynamic of the online poker players and the companies. So, kind of overnight, these companies had to stop their operations and I knew that the mindset of professional poker players and sports bettors wouldn’t be that they are just going to stop making money because they were making tons of money. They were doing a job that they loved. They were working online from home.

They had complete freedom and they were mostly in their 20s, 30s, just having a blast and loving life. And so I thought, “Well, they’re going to have to leave the U.S. because it could take years, if not decades, if ever for the U.S. to regulate online poker in a way that they can make a living doing the same thing.” So, I was already helping retired people and expats and executives and multinational employees relocate to Central America. So, I thought, “Why don’t I just help poker players?” So, that’s how I came up with the idea for Poker Refugees and Sports Refugees and it was this really perfect marriage of all of the years of my background. So, everything started to make sense.

The studying abroad at age 20, learning Spanish, living in all these different countries, stumbling through and crawling my way up the learning curve of how to live abroad and how to do everything from opening a bank account to setting up your utilities and things like that, and also my business background. So, I just combined all of those skills and that expertise into relocation packages that were specifically for this really, really narrow niche market. That was in 2011 and I’m still doing it today. So, yeah, it’s been an amazing time with completely life-changing experience.

From the day that I launched the company, I think within an hour I got a phone call to my cell phone from ESPN wanting to interview me and it just took off from there and I learned so much about online business and it allowed me to travel remotely and yeah, just completely changed my life. It’s been a lot of work and a long road, but I’m really glad that I took that risk even when nobody else understood my idea. They didn’t understand the business model. They didn’t think it would be successful for more than three months or six months and now it’s in the seventh year.

So, another takeaway – to go back to the real estate – is that it’s also become a comfort zone the same way that real estate is because it’s my company, it’s my idea. I implemented everything. So, people say that their companies are like their babies. So, it’s been a personal challenge for me to also try to grow and learn from new facets of the industry or incorporate more things like the online business world and online marketing and everything continues to evolve.

So, over the past year or so, that’s also what I’ve been doing just to continue to challenge myself and to create new products and services that can be accessible and beneficial to people outside of the online gaming industry because, of course, that’s such a small niche market. Now there’s such a greater need for people of every industry to be able to travel freely and live and work abroad.

The whole reason I started Poker Refugees was because I felt so compelled to promote the lifestyle in the same way that Tim Ferriss with the Four Hour Work Week. I just wanted to help as many people as possible because I knew that they would see the light once they got out and, of course, so much has happened. Guys who were living in their parents’ basement in Kansas now have two kids and are living on the beach in Mexico or something. So, it’s just something that was so controversial at the time is now so commonplace and it’s amazing to see.

More and more people now – it’s going to be millions of people who are, if not already – who are seeing that they can live life on their own terms and be completely free financially, geographically, in their career, and just kind of create it as they go along. So, you can never see every step in the road, but you can sometimes see the next step and the next step. Even if you feel like you’re just going really slow or stumbling along, sometimes you look back and you see how everything fit together so perfectly that you could have never planned it that way.

Matt: Right. And at the time, a lot of times it seems like a setback or it seems like a major problem or a challenge or an obstacle but then, when you are able to navigate around it or take a different opportunity or see a different path – all of a sudden – there are a lot of transferable skills and experiences and it all builds up and culminates if you just have the confidence to continue to follow the path that’s being laid out before you.

Kristin: Yeah. And for these guys, I mean people were saying that they were suicidal. This was a massive, massive problem because some of the companies went under and went out of business and some people had millions of dollars – their whole life savings, hundreds of thousands of dollars – tied up in different sites and some of them never got the money back, depending on which site they had the money on. Some of them got paid back by other companies which merged or acquired some companies and it kind of worked itself out, but it took years and it never completely worked out.

Online gaming is still not completely regulated in the U.S. and it’s state-by-state and there are all these things. So, to go from these people who had absolutely no option – they were in such dire straits that the only thing that they could do was leave the country and try to start over from zero. So, I think that’s pretty profound that those people had that courage to take a leap, but maybe also they didn’t see many other options. So, some people went back to school, some people tried to get regular jobs, some people tried to play live poker, and some of them moved abroad.

So, it was really fulfilling to help play a part in turning a super negative, dramatic situation into a positive – both symbolically from my life, from how I ended up in Costa Rica to begin with, through helping these 20 something-year-old mostly guys who most of them never even had a passport – to go from that to a couple years later people sending me messages from South Korea like, “Hey, Kristin. I just wanted to thank you for everything. Now I’m in Asia.” And they just got that courage and deeper self-knowledge and resilience to be able to start expanding their mind and their boundaries and physically going to other parts of the world because they had that confidence.

Matt: Yeah, that’s amazing. So, can you talk a little bit about the business building aspect of it – maybe a little bit behind the scenes, the entrepreneurship business building track – in terms of how, for example, you scaled your business. How did you build infrastructure for your business? Did you start hiring people, outsourcing things, building some kind of a team around it? What was, at the business owner and founder, what was your trajectory in that way?

Kristin: Yes. The business was a totally new concept. So, there was no roadmap. There was nothing that I could follow. The closest thing would have been some sort of corporate relocation company, but I was just a small, sole proprietor. So, I really just created it out of thin air and built it as I went along. So, it took me a few months to get everything planned where I felt comfortable launching it. Then, once I launched it, we continued to reinvent the wheel a few times until we got the policies and procedures down. So, as with most things, you start out without any policies and then – as things happen – you start creating systems and processes to try to streamline things and make sure everything’s going well.

So, I did hire about five people in the first couple months – an assistant, a general manager – just a lot of support staff because there was so much communication, property searches, a lot of non-saleable activities. So, that’s basically what my business is made up of to this day because when you’re moving human beings to different countries, you can’t really get many economies of scale. Everything’s quite one-on-one and everybody’s different. Everyone is from a different country going to a different country with a different budget, with different needs. So, we do have a structure for each relocation, but it’s extremely customized within that.

So, after I hired all those people in the beginning, I realized that I was spending more time managing my staff – or equal time managing the staff and running the business. So, I was getting back to working these 12 hour plus days and I knew from my previous experiences that was not sustainable. So, over the first year or so, I got things more streamlined and systematized that I could just keep a smaller team and have it mostly subcontractors. So, right now, everything is pretty much based off of 37signals Basecamp platform, which is a project management system. I don’t even have any fulltime staff anymore.

Matt: You use outsourced independent contractors and that sort of thing?

Kristin: Yup. So, once I switched to an outsourcing model from a fulltime model, the number of hours I worked every day went down and my revenue went up – which didn’t make sense – but that’s what happened. So, now because we move people to so many countries, I’ll have translators, drivers, concierge people, local guides that I can hire on a contract basis whenever we have somebody going to that destination because it’s really hard to forecast how many people are going to want to go to Costa Rica, who’s going to Thailand, who’s going to Malta. So, yeah, I basically run everything from Basecamp and Highrise CRM system on my computer.

Matt: I think that makes a lot of sense and I think the lowering of fixed overhead and orienting it towards those types of customized projects and independent contractor type relationships I think can often make a lot of sense for business owners. So, I think those are really good lessons. Let me ask you another question. As a business owner, the entrepreneurial journey can get pretty stressful and it can get pretty challenging at different times.

I want to just ask you for some of the techniques that you use for things like time management and productivity – as well as things like stress reduction and those types of things. How do you structure your day and how do you deal with high-stress situations that occur in the business environment?

Kristin: Yeah. It’s so important and it’s something that continues to evolve for me over the years because I think our energy levels change and just as we get older we learn more and more about ourselves and our business. So, I’m always tweaking my daily routine and my morning routine. Right now, I think I have it pretty dialed in. So, the biggest things that have helped me be successful are to make sure that I’m traveling at a sustainable pace and rate because – when you’re going really fast – you will just inevitably spend too much time traveling or planning travel or packing and unpacking. It’s just a huge waste of time.

So, I think people need to be really strategic with how often they’re moving around and where they’re going – just getting set up and getting settled in. So, I try to stay in places for at least a month or so – ideally more – or even just to have a home base and then it’s less energy to take a side trip when you don’t have to bring everything you own with you. So, a perfect situation, which I pretty much have right now in Bulgaria because I’m in control of my environment and I’m living by myself, but around other digital nomads and our co-working space.

So, I just try to focus on going to bed early, limiting going out late at night – which can be hard when you’re in a really fun city – and getting up early and spending the first couple hours of my day doing my most important tasks. It sounds really simple and I know a lot of people have heard this before, but I don’t know, I don’t think people realize how addicted to stimuli they are from their phones and their email and things like that. I started to feel like my days were becoming too controlled by WhatsApp messages and emails and inputs coming in all day long.

So, I changed everything to where I try to wake up between 5:00 and 5:30 and I have a really set morning routine that includes meditation that is sometimes short – anywhere from five minutes to 30 minutes – a ritual where it’s like meditate, do some activity, or sometimes I’ll just do a quick workout in my living room or something like that. Sometimes I’ll go for a run – like 20 minutes – not too long because if you work out in the morning and it takes you 30 minutes to go to work out and then an hour or whatever and then coming back and taking a shower, that can take out two or three hours out of your day already.

So, I try to keep that workout really short and then make some coffee – always Bulletproof, MCT oil, something like that – and I work on – for the next two to three hours – the most important things that are going to take the most amount of focus. That has allowed me to be so much more productive than if I just start out with putting out fires or opening my inbox or looking at notifications for things. So, I don’t look at social media until later in the afternoon because it’s just a downward spiral, but by the time I get that done and then I have lunch and then I work on email and things like that – like more shallow work tasks – because everybody gets that afternoon dip and that’s my least creative, least awake time of day.

So, in the later hours of the day, I’ll do things that are less cognitively challenging and that’s been working for me really well. But the one thing that has kind of taken things to a new level – which I copied from Benjamin Hardy who’s been the most read person on Medium, I believe – I took his journaling course. I used to journal when I was a kid, but I didn’t ever do it in my adult career after college because think of how much you’re writing in college anyway and then you’re working and you’re tired and the last thing you feel like doing is writing.

But I took Ben Hardy’s journaling course at the beginning of the year and now I’ve been journaling every day. It has allowed me to better track my progress towards my goals and I’ve been able to create things and complete them at a faster rate than I was before because I’m constantly reminding myself of what my priorities are and I’m scheduling things into small tasks during the week. I’m just daily writing about what I did, what I didn’t get done, what I want to do, what’s still left on the list. So, that’s really helped me to get through things a lot faster.

So, I would say my main tip for people is to just throw your phone on the other side of the room. Your phone is kind of your enemy and everything is there. You know you can have 100 apps on your phone, but if you can just get the first half of your day – get through the first half of your day – with your most important stuff, then you can relax and have that productive feeling at the end of the day.

Matt: Yeah, I totally agree with that. I think that is outstanding advice and I think if a lot of people listen to very productive people speak about their productivity habits, I think they will find a lot of similarity with what you just said. So, with that Kristin, are you ready for some lightning round questions?

Kristin: I’m ready.

Matt: Let’s do it.

Announcer: The lightning round.

Matt: All right. What is the top book that you would recommend to people – maybe a book that has influenced you or has impacted you profoundly on your journey? What would be your top book recommendation?

Kristin: Let’s see. My top book, my favorite book right now that I’ve already read twice this year, is The Obstacle Is The Way by Ryan Holiday. I love it.

Matt: Okay. What is your top app or productivity tool that you’re currently using that you would recommend?

Kristin: I have two really, really small ones. One is the Focus page extension on Chrome because I know everybody opens tons of apps and you can’t avoid looking at this blank page asking you what your number one priority is for the day. So, it forces you to prioritize. And then also the saving grace that has changed my life and made me a happier person is a timeline blocker for Facebook.

There are a ton of different ones and it basically deletes your newsfeed. So, if you have to go on Facebook for work – which many people do and messages and things like that – in place of a distracting newsfeed, which you have to try not to look at, is a motivational quote or something like that. I’ve had it for about a year and a half now and it saves me so much time.

Matt: Okay, cool. So, what is your favorite podcast that you listen to or blog that you read?

Kristin: I love J.L.D.’s Entrepreneur On Fire because I know he’s doing different formats now, but that 20 to 30 minute consistent format is really easy to digest and I always get something of value from that. And my favorite blog is probably Ben Hardy.

Matt: Okay. What are your top three favorite destinations to which you have ever traveled?

Kristin: Well, one of them I think you mentioned earlier, the wine country in France. I have to say that’s such a magical place. I did a road trip from Biarritz through Saint-Émilion and Bordeaux and I was just pinching myself the whole time. Another one is kind of a rogue destination. In the very southwestern corner of Costa Rica – south of Pavones, the big surf spot – there’s a little place called Punta Banco. I don’t even know if it’s a town really, but it’s just a small area on the border between Costa Rica and Panama.

It’s one of the highest concentrations of plant and animal life in the world and you just feel like you’re in a little mini-sphere of the earth. It’s so surreal to be there. It’s like blue water and white sand and there are no people around.

Matt: Wow. I have not been there, but I will definitely need to put that on my list. That was not even on my radar at all. So, that’s very cool.

Kristin: It’s very idyllic and you’ll see toucans flying around and things like that. It’s nice. Then, my third favorite destination probably for living – well, I don’t know if I’d want to live in the wine country or in Puta Banco – but for the highest quality of life, I’ve gone back and forth a few times between Vancouver in Canada and Amsterdam. I think even though the weather is not the best in the world, they just have such a great culture there, open-minded, friendly people, so pleasant, water, nature, technology, infrastructure. It’s like everything you need is there – good food.

Matt: Awesome, awesome. Those are good picks. I’m definitely also going to hit you up for recommendations on the French wine country because I’m planning to do that next month. So, I will hit you up offline for specifics on that, but I love that’s in your top three.

Kristin: I got you.

Matt: I figured you would. All right, the next question is what are your top three bucket list travel destinations that you have not yet been to that are right at the top of your list at this point?

Kristin: So, Cape Town – which is kind of trending right now – but it’s been on my list for a really long time and I had a plane ticket there in February and I had to cancel it because of my snowboarding accident. So, I’m thinking of going there later this year. Also, kind of similar with the Vancouver/Amsterdam vibe, I’ve heard a lot about Copenhagen and it’s supposed to be one of the best qualities of life in the world and just a really nice place to be. I love riding my bicycle around cities.

So, I’ve been wanting to go to Denmark for a while and I’ve been everywhere around it, but I’ve never been to Denmark. Then another place that I’ve been super close to, but haven’t actually been – it’s not very exotic – but from a historical perspective, when I travel as a digital nomad I really love going to museums and things like that. I’ve kind of been so interested in the World War I frontlines region in France and Belgium. So, I really want to go there as a side trip to check out all of that history.

Matt: Awesome. Okay, last lightning round question. If you could have dinner with any celebrity or author or public figure, who would you choose and why?

Kristin: I would have to say, Marcus Aurelius, the former Roman Emperor. For anyone who’s familiar with stoicism and if you’ve read The Obstacle Is The Way also you would know. I mean he’s a hero and his writings and his thoughts, they transcend time, and I really relate so much to what he wrote back then. It’s just so surreal to read the writings of somebody who was so powerful and to see that they were thinking about and struggling with the same things that we are today in 2018.

Matt: Awesome. Cool. Okay, Kristin, so I want people to be able to connect with you in a couple different ways. You are putting out a whole bunch of amazing content. I have subscribed to your YouTube channel and I’ve just started following your Traveling With Kristin videos – which are amazing. So, I want you to be able to tell people a little bit about that, what you’re doing with the channel, what they can expect, and then how they can follow you there and other places as well.

Kristin: Yes. So, the Traveling with Kristin YouTube channel I just started really in the past six months and it has blogs, travel videos, digital nomad tips, and digital nomad destinations. I just posted my first podcast video on there. I’m doing a lot of live streams. It just has basically everything that I’m learning about or that I’m doing or recommending and helping other people to achieve a location independent lifestyle is there on Facebook at Traveling with Kristin, Instagram, and YouTube. And then to be able to connect with people more directly, I created a group called Long-Term Digital Nomad Success on Facebook.

So, I’m really engaging a lot with the communities. It’s something that I’ve lived and breathed for so many years now. So, my next focus is just helping more people to live life on their own terms – whatever that means for them – and to flatten the learning curve to get started in the lifestyle. So, there are a lot of resources and courses and things that I’m developing right now that I’m really excited to release out there into the world.

Matt: Awesome. Well, you are putting out incredible and really important content. I’m a member of the Long-Term Digital Nomad Success Group in Facebook and I’ve been very impressed with the extent to which you have – not just posted cool stuff but – engaged with people. People need help or advice on where they are in their journey and you’ll just type a comment to them and make a suggestion they’ll appreciate and it will add value to them. You’re definitely super engaged. I really appreciate being a member of the group and would definitely encourage anybody else who’s interested to join that as well.

So, what we’ll do is we’ll put the links to your YouTube channel and some of your other social media in the show notes so people can just go there to the show notes page and can just grab all of that stuff. So, we’ll aggregate it for you and make it super easy to connect with Kristin, but definitely, somebody that you want to be following if you’re at all interested in the world travel, digital nomad lifestyle, or just entrepreneurship and business building in general. So, Kristin, thank you so much for being here. It was awesome talking with you.

Kristin: Thank you so much for having me and if there are any other fellow nerds out there listening, I’m going to be taking a deep dive – actually just launched my page on Medium – which I’ll give you the link for that as well. So, if you want to get really deep into these digital nomad topics and connect them philosophically and academically, I’m going to be getting really into these topics in writing for people who are more into reading versus the videos and the social media stuff. I just thought of that. I’ll make sure to give you that too. I just launched it yesterday.

Matt: That’s awesome. I’m super excited to check that out and yeah, just send over the link to that and we’ll put that in the show notes as well so people can have access to that. That sounds amazing. I look forward to checking it out. Thank you again for being here, Kristin.

Kristin: Thanks so much, Matt. I hope to see you soon for a glass of wine.

Matt: Let’s do that very soon. Have a great one.

Kristin: Bye, bye.

Announcer 1: Be sure to visit the show notes page at TheMaverickShow.com for direct links to all the books, people, and resources mentioned in this episode. You’ll find all that and much more at TheMaverickShow.com.

Announcer 2: Would you like to get Maverick Investor Group’s white paper on real estate investing for digital nomads, how to buy U.S. rental properties from anywhere in the world and finance an epic international lifestyle? Just go to The MaverickShow.com/nomad. The report is totally free and available for you now at TheMaverickShow.com/nomad.

Announcer 3: Do you want to learn how to travel the world for a year plus with carry on luggage only and look good while you’re doing it? Go to TheMaverickShow.com/packing to see a free recorded webinar and learn exactly how Matt does it. He shows you the luggage he uses, the specific items he packs, and the travel brands he likes most. Even if you’re just looking to go on shorter trips but pack more efficiently and eliminate your checked luggage, you won’t want to miss this. You can watch the free recorded webinar at TheMaverickShow.com/packing.

[End of Audio]

Duration: 101 minutes