Dec. 31, 2019

How To Travel the World Full-Time with Remote Year Founder, Greg Caplan

How To Travel the World Full-Time with Remote Year Founder, Greg Caplan

Greg Caplan is the CEO and Founder of Remote Year, the world's largest work-travel program that started as an email to a friend and went viral with over 50,000 sign-ups in the first few days of launching. Greg has since helped thousands of people travel the world while working remotely.

Greg Caplan is the CEO and Founder of Remote Year, the world's largest work-travel program that started as an email to a friend and went viral with over 50,000 sign ups in the first few days of launching. Greg has since helped thousands of people travel the world while working remotely. A former EY Entrepreneur of the Year and SXSW speaker, today he shares with us how he started Remote Year, what the program offers for people who want to work online and travel, and his predictions for the future of work.

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Transcript

Introduction: Welcome to Badass Digital Nomads, where we're pushing the boundaries of remote work and travel, all while staying grounded with a little bit of old school philosophy, self-development, and business advice from our guests.

 

Kristin:  Today's episode is sponsored by me. Did you know you can now shop my favorite remote work tools, video production equipment, and travel accessories directly from your Amazon account? It's true. Just go to TravelingwithKristin.com/amazon to check out all the products I use and love.  

 

Kristin:    00:00:47    So today I would like to talk about a topic that I have been wanting to talk about for probably about a year and a half now. I've had a draft in my notes on my phone with a list of all of the ways that I think the world will change and life as we know it when everybody can work remotely. And when I say everybody, I mean anybody who wants to work remotely and anybody who has a remote job or anybody who is a knowledge worker, who is in the group of people who will be able to work remotely first.  

 

Greg:    00:01:31    Awesome. I love that topic.  

 

Kristin:    00:01:32    So first I'll introduce you so that people know who you are. So here we have some people on the live stream. So if you're just joining the live stream, then welcome. We have Joy and Abby and some other people will start joining. 'cause I just posted, actually I was going to tweet that we are going live.  

 

Greg:    00:01:52    Awesome.  

 

Kristin:    00:01:53    Because I know you're big on Twitter  

 

Kristin:    00:01:57    First. So Greg and everybody who was watching and listening, this is my 35th podcast of the year. So I was just explaining to everybody how I started it. So basically back in 2000 it was really, yeah, in 2016 I moved from, where was I living? I was nomadic <laugh>. I didn't have a home. I had been living abroad pretty much full-time since I was in college. So since the early two thousands and actually Joy, who's in the live chat right now, we met in 2005 in this little tiny town called Nosara in Costa Rica. And we worked in a real estate office there together with her future husband and their dog, <laugh>. I remember her dog would always be in the office with us. We're just like down the street from the beach. We would go surfing at Sunset and then she taught yoga. So we would go to yoga cloth.  

 

Kristin:    00:02:52    It was a great time of my life, but the internet wasn't very good. And so I think we had like a satellite internet with a hundred kilobytes per second, something like that. And I do remember that Skype had just come out and we were like, wow, this is cool. So anyway, fast forward 10 years, I came back to the US and I realized that I had missed out on a whole lot of pop culture, YouTube and social media and podcasting and all this stuff. So I found out about it 'cause I'm like back in society basically. And I put in my phone like to Google Stitcher podcasts. And this was in 2016. 'cause I was like, Hmm, a podcast that sounds like something that I would wanna do. Like this was really resonating with me. And then, so it's just very like surreal today to be on my 35th episode of this podcast.  

 

Kristin:    00:03:47    And I actually have a list like 80 people long of uh, people that I wanna talk to. And I'm sure this is gonna keep growing as remote work becomes more and more popular. Yeah. So here we are. So this is gonna be my first time I'm gonna read a couple of the, uh, reviews and comments because I actually never ask for reviews and everybody's telling me that that's something that I have to do. So if you're listening or watching right now and you have a Apple Podcast account, then please leave a review because that is the way that people can find it and that is the way it can grow. And yeah, so, and that's the way you can support the channel. So I'll read a, a few reviews from other people. I'll do this, I'll start doing this every episode 'cause I think it's really nice.  

 

Kristin:    00:04:31    S says, thank you for your channels and podcast. I think that they're both the most well thought out, engaging and informative channels for digital nomads. Thank you for the great work. Thanks for that. S Brandon DeLillo commented on my interview with Rolf Potts, who is the, uh, author of the book Vagabonding. He says, best interview with Rolf Potts ever and digging into his core philosophy that I've seen, kudos. And then <laugh> Felipe said, I can't understand why your channel has so few views in such terrific content. So guys, make sure to share my videos more. Cuca Moreno says you make the best videos on living abroad. You and Johnny FD are my two favorites, so much so that I've decided to move to Chiang my next summer for good. Thank you for such good work. You're an inspiration to me and many others. I am sure.  

 

Kristin:    00:05:29    So thank you guys for your nice comments and reviews. If you haven't reviewed the podcast yet, please do so. Let's keep it going. And without further ado, I will introduce Greg who's just hanging out, <laugh> hanging out here. So Greg Kaplan, who is next to me here is the CEO and founder of Remote Year, the world's largest work travel program that started off kind of as just an email and then a one page website where you could put in your email if you wanted to travel around the world and quickly grew to more than 50,000 signups. That's product validation. Greg has since helped thousands of people travel the world while working remotely. He's a former EY entrepreneur of the year speaker at South by Southwest. And today he's gonna share with us how he started Remote Year , how he's helping people and companies distribute and travel and work online all over the world and what his views are on the future of work after having accomplished all of these things. So thank you Greg for joining us.  

 

Greg:    00:06:37    I'm so happy to be here. Thank you for having me.  

 

Kristin:    00:06:39    And where are you right now?  

 

Greg:    00:06:40    I'm in Chicago this week, but I'll head to Mexico for most of, uh, this month and next month. 

 

Kristin:    00:06:46   Oh  cool. I'm in Florida right now, so probably a slightly bit warmer than Chicago. <laugh>. <laugh>,  

 

Greg:    00:06:53    I'm sure  

 

Kristin:    00:06:54    It's weird because it's like 30 degrees in the morning and then 70 degrees in the afternoon. So you know, it's winter in Florida,  

 

Greg:    00:07:01    A little bit of everything.  

 

Kristin:    00:07:02    Yeah, the last time I was in Chicago it was February, so it was not a good time to be there. The whole place was frozen. It was like the tundra <laugh>  

 

Greg:    00:07:12    Definitely stay away from Chicago during that time.  

 

Kristin:    00:07:14    Of year. <laugh>. Yeah, you should be in Thailand or something. We have some more people joining in on the live chat. If you're coming in now, gather your questions for Greg and we'll answer them a little bit later in the show. So Greg, can you tell us, for people who have not heard of Remote Year, what is Remote Year in a nutshell? And can you tell us the story of how it started because you had never really traveled internationally that much when you came up with this idea. And it's such a great example of how something can go from a seed, tiny seed of an idea and take on a life of its own and just change the course of your life and the life of thousands of other people. So let's bring in some context to how this all started.  

 

Greg:    00:08:01    That sounds great. So Remote Year, what we do is we operate work travel programs and so we help folks who have jobs that can be done remotely, join up with a community and work remotely from across the world. And we operate in cities all over the world. 12 cities currently four in Latin America, three in Europe, one in Africa, and then four across Asia. So we, we have communities all over the world and if you wanna get involved, just check out RemoteYear.com or feel free to reach out to me directly on Twitter, G Kaplan or just email me greg@remoteyear.com. And so a little bit about Remote Year and how we got started. So I was working in Chicago and I'm from Chicago, grew up in Chicago and it was really, you know, nine to five, I was commuting the same way every single day into a sea of desks full of people that were just kind of uninspired by what they were doing.  

 

Greg:    00:08:53    And I personally just kind of felt stuck. I wanted to get outta Chicago, go see the world, go have some adventure. And the first thing I did was I lined up some work that I could do while I was traveling. And I reached out to my network and over a couple months lined up some work that I could do from anywhere. And step two was to go and start traveling. But personally I didn't wanna do it on my own. Like I was a little bit scared, wanted a community, wanted a group to do it with. So at dinner that night, the day that I lined up my first consulting gig, I asked my friends, Hey, I just got this job I could do from anywhere. Do you guys also wanna get remote work and go travel? And they all kinda looked at me like I was crazy and said, that doesn't make any sense.  

 

Greg:    00:09:38    I dunno what you're talking about. Uh, we're not gonna go with you. And so the next day, basically when I couldn't convince my friends to come and have this adventure with me, I put up a website and it said, who wants to travel to together for a year while working remotely? And it was kind of my personal sad attempt to find friends to have this experience with just, uh, a cry to the internet. Does anyone wanna do this with me? And I sent the link to a couple friends and apparently they sent it to some other friends and it just kind of went viral from there. The first day over a thousand people signed up, just totally unexpected. And then over the next few months, over 50,000 people signed up. And that's when I sort of said, wow, there's, there's something bigger here. There's something that seems to be striking a chord with this group of people across the internet, and what if we made this into something a little bit more than just a group of friends traveling and, and really put a process behind it and really build out, remote you into an organization that could support people having this kind of experience.  

 

Greg:    00:10:37    Um, and at that time we didn't know what it would be or how it would work or where we would go, but the, the idea seemed to strike a chord with folks since then, we've been really building over the last four years our global operations, our community, our experience to really in a meaningful way help people with this core promise of being successful working remotely while traveling the world is part of a community. And you know, both those things are very, you know, new and, and different things that have been done before. Like you said, your experience, you know, you were working remotely but the internet was not good enough. It was really hard to stay connected. The tools and technologies weren't in place. And for us, that's a humongous component of what we're doing is helping people really stay connected in a meaningful way so they can really get great work done.  

 

Greg:    00:11:24    And the other part is community, right? I started this journey because I was looking for a community to have this experience together with, and ultimately that's what we've created. We have a community right now of over 3000 people who have joined our programs and it is so special what has come outta that community? We've had lots of people get married, lots of people start companies, people build these relationships. When you touch down into almost any city across the world now, you could go on our remote nation Slack and you could find other people in our community that are there, spend some time with them, make those connections, hang out, have some fun. It is just so powerful what we, what we've created.  

 

Kristin:    00:12:03    Yeah, I just wanna say that I heard about Remote Year in 2015. Is that when you started it?  

 

Greg:    00:12:10    That's right. We started in the middle of 2015, our first program began.  

 

Kristin:    00:12:14    So it's really interesting because, so Joy and I, who are Joy is on the live chat right now. We worked technically remotely because we were in a remote area just but we were expats so we were living and working in Costa Rica. We weren't traveling while working. Like we still had to go there to do our jobs and certainly the infrastructure didn't allow for that at the time, but there was no terminology over like remote work and digital nomads. Although I did find out that the book Digital Nomad was written in 1997 when I was like a freshman in high school. So that's kind of crazy that it was out for this whole time, but nobody knew about it and they nailed it by the way. They like predicted everything, the two writers. But when I came back to the US for like, it was about a year and a half.  

 

Kristin:    00:13:00    So I got back in late 2015 and early 2016 and I was actually, I think I applied for Remote Year because very cool. The value proposition that I saw after having lived and worked abroad for so many years is somebody can take care of all of the logistics for me and all I have to do is focus on work and having fun. And that is huge. Coming from someone who owns an international relocation company, my job is to help people do what you like, basically what you guys are doing, but individually and for like longer periods of time or no, about the same period of time, like anywhere from a month to a few years or even more. So it's like even having the skills to relocate myself and relocate other people, I was attracted to the idea of having someone else plan everything for me so I didn't have to do it and so I could focus on helping other people. So how is remote Ear a way for people who are brand new to traveling to kind of get their feet wet when it comes to like the digital nomad and remote work lifestyle, but then also like OG people like me, how does that all come together and what are the benefits that you offer to people everywhere on the spectrum from novices to expert vagabonds?  

 

Greg:    00:14:26    Definitely. So I think there's three core components. The first one is remote work and putting yourself in a situation that you can work remotely to have this kind of experience. The second one is the infrastructure to really make that a successful experience. And the third one is community and joining together with a group of people who are like-minded in a similar stage to be supportive of your professional success and to be part of your life while you're doing that. So to unpack those three, the first one is how do you set yourself up to find a situation where you can work remotely? And there's really two ways to do that. The first one is to keep your existing employment and convert that into, uh, permission to have this kind of experience. And the second is to get a new job that you can do remotely.  

 

Greg:    00:15:11    And we really focus in our efforts on helping people take their current employment and convince that relationship to help them and support them throughout this kind of journey. And so we actually have a full-time team whose sole job it is to work with folks who have a job that's not currently full-time remote and put the business case forward, explain how it's all gonna work, and get permission to come on a work travel program. And they've been really, really successful with it. Over half the people that they work with get permission to come. So if you wanna do that, feel free to reach out. And we have a team that's really expert in helping you do that. And so that's the first thing that we do. The second thing that we do is provide the seamless infrastructure for you to be successful working remotely while having this life-changing amazing experience living abroad and traveling.  

 

Greg:    00:16:00    And that requires number one, most importantly connectivity. Number two, seamless infrastructure. That means we have awesome apartments, that means we have great coworking spaces. We do all of the travel and logistics, so people are only going on the weekends, there's no issues that arise. And we also plan the events and activities to support you having fun, but doing it in a way that is around your normal work schedule. And so we have that infrastructure in place that really is specifically built to help people doing work travel programs, not travel programs and not sort of living abroad for, for other reasons. And so for, for that very specific use case, we've built out the exact perfect infrastructure for that kind of person. You know, that that's been a really long journey for us to learn from our thousands of people that have done it. How does that work?  

 

Greg:    00:16:50    How, what do we need to do? What does the right commute look like? What does the right apartment look like? How should we set up the workspace for people to be successful? And that's been an unbelievable journey for us. And now I'm very confident we have the right infrastructure to support people with this intention in mind. And the third thing is really the community. And that I think is the most magical thing about Remote Year is we have a whole community of people on the same page, right? They wanna be working hard, getting their great work done, being inspired, being connected, supporting each other, being successful. And also they wanna have a great time. They wanna get deeply immersed in these cultures and communities on the ground. They wanna meet other people, they want to really have an immersive, authentic experience. And that community that you can do that as a part of is very different than doing it as part of a backpacker community or as part of, uh, a traveling community or a local community which is a little bit different and has different needs and wants. And so the helping people figure out their work situation, having the infrastructure to be successful and finally joining up with a community that's like-minded on the same page and very curious and driven is so critical. And I think that's what we've created at Remote Year to help people do this as effectively and successfully as possible, so.

 

Kristin:    00:18:07    How do you specifically help people find remote jobs? Because this is something that is such a struggle and I know that you guys started with one year periods where it was like 12 month program, one group of people you would go to a different location every month. And then I see now that you offer shorter programs, is it four months or two months? How many different programs do you have now?  

 

Greg:    00:18:33    We have, uh, work travel programs of all different lengths everywhere from one month to 12 months now. And different itineraries go to different locations in different amounts of time. So depending on what someone's looking for, we will, we'll find the right itinerary for them, but as short as a month and as long as a year.  

 

Kristin:    00:18:47    Okay. So people could theoretically, like if you're listening, you could keep your same job, go travel for a month just to get a different experience. And there's a lot of different benefits to this, you know, well Greg can tell us some of them, but getting more creativity and inspiration in different countries, expanding your professional network and I mean, just being more productive. There's all of these studies that show that people who work remotely can be more productive and just giving yourself a chance for breakthroughs. So having these short experiences can be personally beneficial. It can be fun and it can also have professional attributes and help your company, but then there's also a group of people who need to quit their job in order to travel or need to change jobs or something like that. And I'm sure that as the years went on, you had a lot of people who were like, I wanna come on this, but my boss won't let me do it.  

 

Kristin:    00:19:45    What can I do? Like how can you help me? So how does remote ear help people find jobs? And then also what is kind of the burden of proof, as it were for companies, for employers? How do you convince them or how do the remote ear citizens, how do they convince their employers to let them work remotely? Like what is this hurdle that we have to get over? Is it a cultural block? Is it just business as usual? Is it a psychological thing that people have against it? So yeah, I guess that's, whoops, that's kind of a two-sided question. But yeah, how do you help people find jobs and then how do we convince all of the business owners in the world that this is a thing that people should be able to do, let us live.  

 

Greg:    00:20:36    <laugh>. Uh, that's great. So I think there's a few questions in there. The first one is, uh, how do we help people actually figure out the right remote work situation for themselves? And we really try to prioritize people staying in their current role. And so we have a lot of support that we provide people to make the business case to their current employer to be able to come on the program. And how do we do that? It's, it's really, there's a couple different stakeholders. The first one is your direct manager and their concerns are always around how are we gonna make sure you're able to get your work done effectively, right? And so what we like to do is really go piece by piece, line by line with people around what are they currently doing, how does it work and how will it work when they are doing it remotely?  

 

Greg:    00:21:20    And we have some frameworks that we have and business case templates that we have around exactly how that works around the communications, around their productivity, around their connectivity of their work product, things like that to really lay out the case, like most of the things that I do already are digital and help spell that out for folks and explain for the things that are gonna be a little different. Here's how we'll be very proactive and make those even better from a remote environment rather than in person. And generally managers are comfortable with that. They can understand how this is all gonna work. And then the next piece of it is, um, more of the HR side. How does this work from uh, immigration perspective in visas? How does this work from a taxation perspective? What does healthcare look like on the road? Or all these different things where the HR org is supporting the employee. We have best practices from hundreds of companies that have given permission for their people to go and how they set it up, how they think about it and how they mitigate all that liability. And so we have a whole process now also set up to help navigate through those HR and tactical operational questions that come as a sort of second piece usually after the productivity piece.  

 

Kristin:    00:22:28    Are you going to companies and like lobbying to help, you know, kind of change the corporate culture around remote work because some people don't even really know about it?  

 

Greg:    00:22:39    Definitely. Uh, we have lots of conversations with companies about remote work holistically and as a subset, remote remote work travel programs, you will be surprised more and more companies across the world are really thinking critically and strategically about flexible work. People are demanding it, the tools are in place and the best companies are really starting to lean into it in a meaningful way. And I think you're starting to see that go mainstream so much so that now 52% of the US working population works at least part-time remotely. Yeah, so this is, this is become a mainstream thing very recently, you know, that is only part-time remotely. So less people are actually working full-time remote. But it is an emerging trend that every boardroom across the world is starting to have a conversation around, um, because the technology allows for it and the best talent is really just demanding it. But while people are going through that journey, a lot of times will come into the conversation and, and work with them and say, Hey, we, we can help you. We've seen lots of other orgs and how they've done it, what the pitfalls were, what their successes were, and help them kind of think about it. Um, so we have a lot of those conversations ongoing.  

 

Kristin:    00:23:48    Why do you think it's important for people at large to have an international experience living abroad? Because when I trace back to my why for like why I am doing this podcast, why I started a YouTube channel, why I started a company to help people do this, it was like at the core, I just wanted to help people do what they wanna do. Just to realize that you can live in an alternative way and that you don't have to follow any specific rules or guidelines. Just kind of like giving people permission to live differently. And that has really driven me since the, you know, early to mid two thousands because the first time I studied abroad it was 2002 and I cried on the airplane. Like I was so scared. And then I got off. And the first 24 to 48 hours were terrifying as it can be. I'm sure anyone who's moved abroad by themselves for the first time is the first few days are awful. And then it was like the best thing ever. And I was like, why didn't anyone tell me I could do this? So what do you think after having been to so many countries, why do you think it's important for everybody to have at least one month living in a foreign country?  

 

Greg:    00:25:09    Yeah. Well our, it always starts with our mission. And our mission is pretty ambitious, but it's to make a more peaceful and productive world. And the way we try to do that is by fostering authentic connections amongst diverse groups of people. And we believe at our core humans are all the same. Um, and that's a pretty fundamental belief that people with very different experiences from across the world are the same and all humans are one. And it's so important to us that people have that realization and understanding that people across the world are not their enemy. They are their brothers, right? And they need to be thoughtful about them and be more empathetic and understanding of those folks. And only together united can humans rise up to support each other and be productive together and attack some of the larger existential questions that we have as a species.  

 

Greg:    00:26:02    Things like global warming, it's really hard with the, when it's a tragedy of the commons and everyone's responsible and, and that means no one's responsible. So we think that by helping people have access to this kind of experience living in a country across the world, and really understanding the similarity and oneness and connectivity that they have with people from very different experiences, then they can start to understand the connection between all of humanity and how we're all similar and should be treated with empathy and understanding and respect. And then we could start working together more peacefully and productively as a whole global community. And so that's really what we believe having that exp experience does. And that's why we're working every day to make that accessible and possible to more and more people, which is so core to what Remote Year is, right? Remote Year is working while traveling and that makes this kind of experience accessible to people who can't just afford to pay for that out of their savings, which most people in our generation don't even have. Yeah. Um, so that's what the core innovation of Remoter is, is to have that kind of experience in a way that you can do sustainably financially. Awesome. And that's really what we're all about.  

 

Kristin:    00:27:11    Yeah. And we're, well, we'll talk a little bit at the end about the, the prices and like how much it costs to do this because people have this idea that to travel internationally is so expensive when in some cases they can spend less per month than they would if they just lived at home <laugh>, which is something else I found out in my first semester studying abroad. I was like, well actually my second semester in Australia, I was like, I'm living on the beach in Australia. At the time the currency exchange rate was really good for like half the cost of living in my dorm in Orlando. And this is crazy and nobody <laugh> knows about it. So yeah, I agree with what you said and I think that that's something that has taken many years before it really sunk in for me because we are kind of bred from a young age, like it's a small world, but also everybody looks different.  

 

Kristin:    00:28:03    Everyone wears different clothes. We have to be afraid of what's different from us. And I've been to over 60 countries now and there's still countries that I haven't been to because I think I have a subconscious fear of a certain country. But it's literally like every human being. I don't wanna say all people are the same, but every personality of every single one of your best friends and family members is represented in every city, state, country around the world. It's like you have the funny people, you have the nerdy people, you have the people who cook, you have like the police officer, the lawyer, you have like all these personalities and all these careers and, and life purposes represented in each place. And I just really wish that the news <laugh> the mainstream media would portray people realistically instead of making it like all about us versus them. So I really love that, that you said that. And I'm interested to know, for the people who have gone on Remote Year who are traveling abroad for the first time, how have you observed their attitudes changing and their perceptions changing of what they thought before they arrived in a certain country? 'cause you've watched like hundreds or thousands of people go through this. Uh, how, how is it different from like before they get to a new country, let's say they're in Slovenia or Bolivia or something versus after that month that they spent there?  

 

Greg:    00:29:36    Yeah, definitely. And when I say everyone's the same, I don't mean everyone is the same in every single way, but when I say everyone's the same, what I mean is that people across the world all have the same hopes and fears and dreams and they care about their family and their safety. They, it, it's, there's a lot more that we have in common than we have different, and that should be celebrated and understood rather than thinking about what divides us. We should be thinking about what connects us. And I think that's really an important, um, so I, I think one story that I had personally, um, during the first year of Remote Year was really eye-opening and that that was, we were in Istanbul and at this time in Istanbul there was a little bit of unrest happening and a lot of folks were getting messages from their families, Hey, you're in Istanbul right now.  

 

Greg:    00:30:20    There's been some terrorist activity. How do you think about this? Are you safe? What's going on? And the, there was a lot of folks that were getting messages from their family about the safety that was going on with the situation on the ground. Yeah. And I was out at dinner with a couple new friends that I made that were Turkish and we were hanging out, we were talking and you know, our personal stories came up and they said, where are you from? And I said, well, I'm from Chicago. And the guy paused and he looked at me for a second and said, wow, Chicago, isn't it dangerous there,  

 

Speaker 3    00:30:54    <laugh>?  

 

Greg:    00:30:56    And the the reality was like, it was an eye-opening experience for me because yes, like you're seeing all these news reports all the time about all the violence that's happening in Chicago and it is real and it is palpable and it is a dangerous place. But for my family who is back in Chicago, they're saying, you're in Istanbul, isn't it dangerous over there, <laugh>? And it was just an incredible experience to think about. They're all just reading these headlines, which are, you know, portraying the, in a lot of cases the worst possible outlook and perspective on a place. And you know, there's this saying, if it bleeds, it leads, right? Like you yeah, you only hear about the violence and, and the reality is we're living in a time now where, um, human inflicted violence is at an all time low, right? But we're hearing about it more than we ever have.  

 

Greg:    00:31:42    And so there's this perception that we have that places that we haven't been to are so dangerous when the reality is they're probably not that much safer or more dangerous than where you're used to being. You just don't have as much familiarity. And so it's really easy to sort of get tricked by the fili familiarity bias of the danger that's happening in these places and thinking those people are very different. They're, they're living in fear and living in danger and they're living in these very difficult conditions. Um, and it makes it easy then to see them as others and you know, support policies that are aggressive or antagonistic or doing all these things that are just not in your best interest or their best interest because you have that misunderstanding. And so that experience for me was, you know, really eye-opening personally around that perception that people have literally of each other across the world because they don't have that understanding, that empathy and that that awareness.  

 

Kristin:    00:32:41    It's so true. And it really permeates every geographical region. Like when I lived in Costa Rica, they were at odds with Nicaragua. So it was people in Costa Rica said, don't go there, it's dangerous. And then when I am in Nicaragua, they're like, don't go to Mexico. It's dangerous. And then <laugh> Yeah, it's like, you know, no matter where you are. And also yesterday, so I don't watch the mainstream news very often, but I just was like eating breakfast. I turned it on, you know, making coffee and I overhear them talking about the escalating violence in Mexico and that 20 people were shot and it's like this epidemic and the drug war. And I was like, how are the US news anchors going to come on and say that Mexico is dangerous when we just had our 400th mass shooting? They have, don't go to London because there was a stabbing and on the other hand, 20 people were shot in Mexico. I'm like, how many people were shot today in like Oklahoma or whatev, you know, <laugh>. Like, it's just so crazy.  

 

Greg:    00:33:46    Totally. Yeah. And I, I think that that that fear is really what fuels a lot of problems in the world, right? People have that fear and they think of others as different. And that's why we believe by exposing people to authentic human interaction with people that are different than them is a really important lever for making the world a more peaceful and productive place. Yeah. And, and that's something that we wanna continue to enable for folks because you know, we all know people who haven't had the opportunity to have those kind of experiences and they have more fear than anybody else and they probably also have less understanding, less awareness and less acceptance of people who are different than them. And so that's what we're really trying to engender and foster is that empathy, that understanding and awareness, um, so that the world can operate much more peacefully and productively.  

 

Kristin:    00:34:38    I honestly think, like it sounds cliche, but I think that is the only way out of the situation that we're in with all of these global problems. And last winter actually, I'd had a, a sit down interview on the nomad cruise as we were floating over the equator. It was so surreal, um, with a guy named Vlad from Russia and we were talking about changing the perspective like from a geopolitical view of countries with borders to like one global planet because we're so connected now with technology. Everything is so interrelated and interconnected like economies, the climate, the environment. Like we can't approach it from the old way. It just simply won't work. And so I, I really do hope that Remote Year and these other work travel programs and just the whole mindset just helps to change. Actually I'll ask you in a little bit about this remote nation, but first, if anybody ever does get this question from your friends and family, like isn't it dangerous wherever it is that you're going? Because no matter where it is, I'm sure somebody thinks it's dangerous. This is the rebuttal that I have used many times and it shuts people right up. I say it's not any more dangerous than the Walmart parking lot. And they're like, Hmm, good point. Okay. Especially at night, don't walk through the Walmart parking lot at night. So yeah, people can't really argue with that. So that just pretty much lets it go  

 

Greg:    00:36:06    For sure  

 

Kristin:    00:36:07    <laugh>. But what would you say to the people who, who say that digital nomads and remote workers are privileged, which I think is true to an extent, but that we're privileged, we're from developed countries, we don't integrate with the local communities where we travel, we isolate ourselves. This is a big critique of international remote workers in places like Lisbon and Bali. So how are you guys trying to attack that and change it?  

 

Greg:    00:36:43    First of all, it definitely is a privilege. It's something that a lot of people want and they prioritize doing that. And what Remote Year, year's all about is enabling more people to have that privilege. And there's a lot of folks that we haven't yet enabled to have that kind of experience and opportunity that we would love to someday figure out how to do that because this is an amazing life changing experience, but is definitely something that is still a privilege and will continue to be a privilege that we wanna continue to make possible for more and more people. Um, so that's number one on that side, I think. Absolutely. Yes. And on the other side is how do we be good members of the communities that we're in right when we are going to different locations? And the reality is people throughout all of human history have been immigrants.  

 

Greg:    00:37:31    They've been wandering, um, you know, before agriculture for the first 50,000 years of humanity it was hunter gatherers wandering the world and that's how humans populated the earth. I think ever since the beginning of time there has been a tendency of folks to stay with people that are more familiar to them. And so that's something that in all cases you have to work to break down those walls and build bridges and unite people. And so that's, that's something that we work really hard on because it is comfortable and natural for people to spend more time with folks that are more familiar to them. And it's really challenging to go and extend an olive branch and meet folks that are different than you. And so we have teams who are in on the ground in each location and one of their core responsibilities is to give people seamless opportunities to meet folks from the local community to give back through volunteering, to have networking opportunities, to have educational opportunities, to have social opportunities and get to know those folks because while you're there for a period of time, it's, it's pretty hard on your own to break into that.  

 

Greg:    00:38:41    And that's one of the core things that we try to do is to not only build the community amongst the people who are traveling, but also give them really easy opportunities to get to know folks in those local communities in ways that are not super forced but are seamless and comfortable because, you know, it's, it's not easy to do on your own even when it is something that you really want to do and try to prioritize.  

 

Kristin:    00:39:04    Yeah, I mean I'm guilty of that. Like I wish that I did more kinds of community service and things. Sometimes I, I feel like suffering human suffering comes when we spend too much time thinking about what we're doing individually and not helping other people. And so how are some of like the specific ways that you guys have gotten involved with the community? Because I know from relocating people, a lot of them have said like, I wanna give back, I wanna do community service. I send them like a list of things they can do. They never do it. They never take language classes. So yeah. What are some of the ways that you guys are facilitating that?  

 

Greg:    00:39:45    Yeah, we, we think that every community has different needs and we have a team from that community who can really get deep and understand what the needs are of those local communities. Um, and they look a little bit different everywhere we go. So in some places we'll have a relationship with a local dog shelter and in some places they have an issue where they need homes built for low income community members and we will participate in building those homes. And in other places we get more involved with maybe a, a river that has pollution and litter and things like that. And so we like to understand from the communities that we're in and from people that we have on our team within those communities, what are the best places for us to give back? How, what are the needs that this community has? And then we'll develop relationships with those local, not-for-profits and have a more structured, ongoing relationship.  

 

Greg:    00:40:36    So whenever groups come into the community, they're able to have a very seamless way to give back without a big lift. And we do it all together. So it's a lot more fun and it's a lot easier than just, you know, having a place that you can go and you have to go figure it on your own. We plan the whole experience, we make it super easy for people to do. And that goes back to the idea of playing this stuff around people's work schedule so they don't have to do a big lift to make that a reality. It's just something that's on their calendar, they have accessible to them without any planning or overhead and they just get to go and enjoy it. Um, they get to give back, they get to make an impact and, and not really spend too much time on the planning or the follow up, but really just get to make that impact when they, you know, have the time to do it.  

 

Kristin:    00:41:20    Yeah, and I think, I think I still will go on, uh, one of the remote ear trips because it, it's, it is still like kind of a trend right now, but it's not really a trend. And I know that you're like a little bit of an an anthropologist because I did Google you and read a lot of your stuff and we are seeing eye to eye on a lot of the same things. Fellow remote work research nerd, <laugh> <laugh>. So one of the things that I've noticed that is a trend but also something that I think is built into human DNA is tribal communal living. Yep. And obviously roaming and wandering around the world. But the way that we're seeing that manifest in in present day modern society is through co-living spaces, services and remote travel programs where there is a service provider that's offering to take care of pesky errands and house chores and personal stuff.  

 

Kristin:    00:42:19    For example, one of my friends lives at the entrepreneur house in San Diego where they actually have like a minimum you have to have a, a minimum of a million dollars a year in revenue to apply to live there. It's like kind of like living in a mastermind in a high level mastermind, but the rent, it's not that expensive. I think it's like $2,000 a month or something like that, or 2,500 a month, but it includes all of your food your utilities made every other day, all kinds of things kind of packaged in together so that you don't have to worry about it, you can just focus on having fun working on your projects and your side hustles and things like that. And then on another level, we have co-living spaces all over the world that are starting at really affordable prices, like 400 bucks a month or something where you can also get access to those services built in so you don't have to worry about doing like maintenance and stuff. And then you have remote travel programs that are starting to package that in together too. So do you see this as kind of a coming back to the roots of society or is this just a passing trend or, you know, yeah. Is this something that is like natural to human beings? You know, they used to say it takes a village to raise a child and then now everyone just lives in separate boxes with separate SUVs and separate sets of monthly bills. So like what do you have to say about that?  

 

Greg:    00:43:49    Yeah, I, I I like to think about um, the history with a longer term view to try to understand what is natural and not natural for humans. Because I think it is pretty telling. And like I said, for humans been around for about 50,000 years, for about 45 of those 50,000 years humans were wandering, right? They had this, this innate itch to see what was beyond the horizon and they would wander and they would look for food and they would do that together. And only during the advent of the agricultural revolution when people started to cultivate crops and have to stay in one place to do that, did they put down roots and stay in one location. Um, and so I think it is a long enough period of time that that can be a natural state of things. But the way that that we've evolved is that for a lot of human history we were way more nomadic and we were way more curious about what's what else is out there.  

 

Greg:    00:44:48    Um, and I think even during the last 5,000 years, people have actually been fairly nomadic compared to what you would expect. Immigration's been a core feature of, um, humans over that last 5,000 years as they've migrated across the world and for all different reasons, a lot of them, economics, some of them political, some of them religious, all kinds of things like that. So it is sort of a natural order of things. And then over the last maybe a hundred or 200 years living situations have also evolved pretty rapidly, right? People used to live intergenerationally on one plot of land, um, and then over the last 50 or a hundred years people lived, uh, for most of their lives in one home, right? So you, home ownership was a core feature of the last 50 years. Um, and our generation is way less stable than that, right?  

 

Greg:    00:45:37    Way more open to owning a home and then selling it, moving into a new one or even renting multiple different locations for just a year at a time. Um, and I think you're seeing sort of a next evolution of the atomizing of land ownership, um, going from hundreds of years to tens or dozens of years to years. And now we're seeing one more opportunities for folks to have a location that is home for a much shorter period of time, of months up to years through different rental formats. And I think this co-living model ultimately to me is interesting from two components. One is that it makes it very easy to move, right? You can have, it's because they come furnished and they're available month to month or week to week or day to day. You can realistically move much more frequently, um, and do it in a way that makes sense 'cause they're not bringing your furniture along with you and things like that.  

 

Greg:    00:46:34    And the other component of it is it reintroduces this dynamic of community and I think we're only at the early stages the, you know, the top of the first inning of what that's gonna become. Um, there's all kinds of different models that are being set up around how co-living works. And some of them are stay in this city, have a much smaller personal space, but a large community space is one model. Um, another model is just available sort of on a shorter timeline that's burnished and interesting. Another is to join the community and travel around. And I think there's all kinds of different takes on what what does that mean and what is the value of it for each of the people? And I think it's only just beginning, like we're gonna see all kinds of new things we can't even dream up today, um, as the internet makes it more feasible and attainable to really make that happen in new and interesting and exciting ways. I have no idea where that's gonna go. Um, but I'm very excited to watch that unfold.  

 

Kristin:    00:47:31    Yeah, I think the big takeaway of what you just said is that the modern way of designing a daily life is not completely fulfilling. I think we can say that with a high degree of certainty that, you know, whether it's the white picket fence or whatever it is, whatever dream life that's been implanted in your head from a young age, it's not necessarily all it's cracked up to be. And we can look back at the nature of humanity over tens of thousands of years and recognize those tendencies in ourselves. The tendency to want to wander, you know, to dream, to walk, to be around people, to not feel lonely. Like these are all like inherently human characteristics. And I think it's a matter of everybody giving themselves permission to be okay that they want to live in a different way than maybe they have lived their adult life to date.  

 

Kristin:    00:48:37    And, um, I wanna get to some of the questions from the live chat and also the lightning round. But before I do that on this note, I wanna read this quote to you and I think it's perfect for this topic of conversation. I would love to get your perspective on it and I will cite the source. So this is an article on Medium called Welcome to the New Midlife Crisis. And yeah, I've already read the article twice, but it's basically the gist of it is from a developed country, let's say the US so middle aged US citizen, like upper middle class, let's say, people who've done everything right, you know, followed all the rules, the wife, the kids, the two cars, the nice house, the Pottery barn stuff inside the job, the promotions, the recognition. It's like going through all of these life rituals and then finding out that that doesn't matter.  

 

Kristin:    00:49:39    It's like how many times do we have to relearn that lesson? And so there's this quote, it says this, the midpoint of life represents the moment of maximal conflict between our drive to seek external solutions to our emotional dilemmas and our recognition that ultimately they don't work in the rough patch. We are forced to realize often against our will that the life building activities of youth, job relationship, children house have not taken care of what's unresolved within. And then she goes on to say, it is never possible to have it all. You will in fact miss out on or lose some things that might have been very meaningful to you. These disappointments are a feature, not a bug of a well-lived life. And I think both of us are in our thirties. You came from a very strict, uh, corporate background or traditional corporate background in Chicago, high stress job, commuting to work, sitting there with all the other cubicles. And now your life has looked completely different through choices that you made. So what does that quote represent to you and what message would you like to share with people who might be sitting in that midpoint of life? Because not all remote workers or digital nomads are 18-year-old backpackers, you know, with a laptop. Some of them are in their fifties, sixties, seventies. What is the message you wanna share with people to help them feel like they're not alone in this kind of dip? Yeah,  

 

Greg:    00:51:20    I mean definitely it was, it's a, it's a thing that lots of people feel. They feel stuck like they have this itch to go and, and try new things and meet new people and explore the world. And it's really unbelievable that we're living in a time where that's possible. Where remote work makes that a reality. Culturally, like you said, it's, it's on the forefront. It's something that is a little bit, um, on the bleeding edge but can be done if it's something that you prioritize and if it's something that you wanna do, that's what remote you're set up to, to help with. And so if it's something you're interested in exploring, um, and it's something you are thinking might be something that is for you, feel free to reach out to me directly. I'm happy to chat with whoever. 'cause it's a strong passion of mine to make this type of experience a reality for as many people as it possibly can because it changed my life and I think it's gonna piece by piece change many people's lives and eventually hopefully make the world a more peaceful and productive place.  

 

Kristin:    00:52:16    Yeah, just to think of sitting in the, in the office building in a frozen Chicago thinking that there has to be more to life than this after you have a good high paying job and all of the comforts, you know, modern aid comforts that we, that we get to experience that we're very fortunate to have. Sometimes you're happier with less of that and more of the immersion and just connection with what's going on in the world. So  

 

Greg:    00:52:45    Definitely  

 

Kristin:    00:52:46    Love that. Um, so we do have some questions from the live chat if anybody else has any, feel free to hop in at any point. Joy is asking if you have any plans for a remote family. So she would love to set up a place with her husband and their kids so that they had like an online homeschool sort of thing and they could experience this without the additional logistical demands of moving a family.  

 

Greg:    00:53:14    We have actually heard that a whole lot, joy. Um, I'm glad you asked. We don't have a timeline set up, but it is something that we've thought a lot about and would love to set up as soon as we can. Probably, probably not in the next few months, but it is near the top of our list to set that up. There are a whole bunch of different considerations logistically, um, safety, health, schooling that we have to figure out. So there are, we have a list of unanswered questions, um, and we've had conversations with lots of folks like you to help us start to answer a few of them, but we're not there yet. So as we do have those answers and we get to a point where we feel comfortable providing that experience of as well as we possibly can, and we hope to roll that out at some point in the future.  

 

Kristin:    00:53:57    Nice. That would be great to see because that is a big thing that holds people back from traveling. It's just, it's just a lot. I know people do it, but it's still too much. And then I also noticed that you guys are building out your own coworking spaces. We talk about coworking and flexible work a lot on the show. And I made kind of an audacious prediction the other day where I said that I think that the flexible work industry is completely underestimated as far as the shift away from like traditional leasing into flexible leasing. And of course it's a pain in the butt to go out into the world or it's becoming easier with things like the coworker Global Pass and all the coworking spaces popping up. But why did you guys feel like you needed to take it upon yourself to pick up, like or lease or buy buildings and then build them out for Remote Year people.  

 

Greg:    00:54:58    Yeah, we've actually been doing that since almost day one. When we started in 2015, coworking was pretty nascent. Um, and especially internationally outside the US there was not coworking spaces to the quality that we wanted in the locations that we needed. And so in a lot of those cases, we had to build our own coworking spaces to support what we were looking for. For our community, that is less and less the case as coworking has become more and more common. Um, so we only do that when we feel like we have to, uh, we would rather partner with an existing coworking space because they have the infrastructure in place that they've already built out. Um, and we have really, really rigorous criteria for selecting that. But also they have the, an existing community and tapping into that local community that's existing in the coworking space is a really strong value to people on Remote Year to make those local connections that we talked about.  

 

Greg:    00:55:48    So we like to partner when it is possible, but if there doesn't exist the right space, then we will build it out like we have done in on the beach in Split, Croatia, which is unbelievable. We did it in the neighborhood we wanted to be in, in Lisbon. We did it before actually in Kuala Lumpur, but we actually found other coworking spaces that emerge that we've now moved into because they now exist in the way that we'd like them. So we, we aren't doing that because it's, you know, super strategic for how we're thinking about providing this amazing experience. But we do it when we need to because it doesn't exist in the places that we wanna bring people to.  

 

Kristin:    00:56:25    Yeah, I think, I mean, sometimes if it doesn't exist, you have to make it yourself and that's totally okay. And then there's one other question before the lightning round. One of the predictions I made in this article was that eventually I think we're gonna have some sort of a global citizenship, global passport, global taxation system because a lot of people are living in like a parallel universe where they're kind of like not a resident or a citizen. Well, they're citizens of somewhere, but they're just kind of floating around. And I know that you guys call your alumni of the Remote Year program remote citizens of a remote nation. And I just find that to be just a very, like, visually, like that's something that I see happening organically with everybody who's kind of moving into this more nomadic way of lifestyle. So can you talk about how that works and why that's a benefit to people who have gone through this experience?  

 

Greg:    00:57:29    Definitely. I think there's a few components of that. Number one most importantly is the community. Um, the community of people that come on our programs, um, have this very unique connection to each other and we develop that connection digitally on our Slack community. And so people are able to remain connected digitally well after the program ends with that community. And so that's super huge that that relationship that you build. Relationship number two is, there's actually from a tax perspective for people who do a year long program and they're US citizens, there's this thing called FEIE, which is foreign earned income exemption, which means that people actually are exempt from paying income tax on their first hundred thousand dollars of earnings if they spend at least 330 outta 365 consecutive days outside of the country. And so from a technical perspective and a tax perspective, people actually are citizens of the remote nation because they're not in a very pragmatic sense paying tax in the us. Um, which is I think a really interesting opportunity that having this kind of travel experience opens up and is a humongous cost savings for folks doing a program like Remote Year or doing remote  

 

Kristin:    00:58:44    Year. Yeah, like, like this video, if you've ever gotten the FEIE exclusion, who's in that club?  

 

Greg:    00:58:50    <laugh>. And the third one is, you know, what, what does this become like? What, what does that ultimate look like? And I think as we look to the future, countries are gonna start to realize that labor is actually an asset and not a liability. And humans are an asset and not a liability. And countries will eventually start to compete to attract folks who are living and working in these countries, whether that be domestically or remotely. And I think we're gonna move to a world soon where we actually have declining populations rather than growing populations. You're starting to see that in places like Japan and Italy and some other countries. And I think as we get over the next few decades, we're actually gonna start to see populations start to decline in a lot of countries and they're gonna start to compete for more population. And so they're gonna be trying their best to figure out the right suite of government services and offerings to attract more people rather than make it competitive through their complex immigration processes and policies. And so we're, I believe start, see, gonna start to see governments creating the right set of opportunities for people to come there for short, medium, long periods of time and be citizens for a shorter duration rather than for life. And they'll become then citizens of the world who can go to places when the governments have the right offering for them. So they will exist mostly digitally and they'll be in different places, but they'll have countries competing for them rather than, um, having these arduous processes for getting into countries.  

 

Kristin:    01:00:28    Yeah. If you're listening or watching this right now, just embrace your power because we are in the midst. I think Greg and I agree of seeing a shift in the power balance between employers, employees, and governments and citizens. And it's not like some sort of violent revolution. No. It's just an owning of our natural worth and value as human beings. And we are seeing this start as tech companies start competing for talent all over the world, offering tons of benefits. We have something like 99% of people want flexible work and the people who have it don't consider it a benefit, but just a requirement, a, a necessity. And then we have company or countries like Estonia, Lithuania, Qatar, Japan, a lot of countries coming up with either some sort of new remote entrepreneur visa or e residency scheme. And soon we will have a, I think a citizenship category because if they have citizenship categories for retirees, they're definitely gonna have them for remote workers.  

 

Kristin:    01:01:38    And the small agile tech savvy companies are gonna be the first ones to do that. So if you're on the cusp of thinking you might want a lifestyle like this or thinking that it's for you, don't just, you know, wait around for people to say you can do it because the writing's already on the wall. And I think that there's enough opportunities now that people can seek them out and then you can still be an early adopter. And then in the next few years we're gonna see like, I think a critical mass, like a tipping point where it goes from being like really weird to like, oh, everybody can do it, or it's just normal. It's just gonna be the same thing as if you're like, I work in digital marketing, like I live, you know, in Croatia or whatever. They'll just be like, oh, okay. So speaking of, uh, travel though, let's get to the lightning round. I've held you over the, over the one hour time slot. Okay. Let's start out with, uh, what is your morning beverage of choice  

 

Greg:    01:02:36    <laugh>? I try not to drink too much caffeine, so I only drink it a couple days a month. Um, when I do, it's just green tea. Um, but mostly water. I like to stay hydrated and hydration's a personal passion of mine. I like to remind people to hydrate. If you're watching this, make sure to go out, get some water and stay hydrated.  

 

Kristin:    01:02:55    I am a, a large proponent of Hydro Flask who does not sponsor this podcast. However, you can purchase a Hydro Flask in my Amazon store at TravelingwithKristin.com/amazon and get all of my favorite remote work tools and travel tools. I drink tons of water and I've actually lost a ton of water bottles because I leave them all over the world. But, um, yes, water, very important. I'm jealous that you don't drink caffeine 'cause I'm super addicted. <laugh>, um, Mac or PC  

 

Greg:    01:03:26    A Mac, uh, I don't think it really matters as much anymore 'cause almost everything's in the browser and cloud-based anyway. But I feel like Apple's done such a good job making these machines work well and also the heirs are pretty cheap. So I'm a Mac guy. Yeah,  

 

Kristin:    01:03:40    My mom just got one. My mom and my 93-year-old grandma have MacBook heirs so nice. The world we live in. What is your favorite piece of digital nomad or tech luggage or a backpack?  

 

Greg:    01:03:56    You know, it's funny, I, all these people get so into like packing lists and what they have. I keep it so simple. I just have, uh, a little carry-on suitcase and a simple North Face backpack. I, I don't know, I'm not, I don't super geek out about that stuff. I like to keep it super generic and I don't have that many clothes, so pretty easy to put a couple black T-shirts and a couple pairs of jeans and a sweatshirt into a a bag. So unfortunately, I don't know. I would love one, one Hope, uh, request for gear is I would love a computer that has an extendable screen. So if you think about like the screen, not just sticking along the keyboard, but like moving up so when you're sitting there you can look straight up and be a little bit more ergonomic without the whole like laptop stand and keyboard.  

 

Kristin:    01:04:42    Yeah, that is awesome because I currently have my laptop on a laptop stand and I have a separate keyboard, which I am using. And, and every time I go in a coffee shop, people ask me what it is <laugh>, and it's the roost, the roost stand or the rooster stand. And it's also in my Amazon store. I get people stopping me every day 'cause I, they're like, you have such good posture. I'm like, it's this plastic contraption, <laugh>. Anyway. What is your favorite remote work tool or app that you depend on a lot?  

 

Greg:    01:05:15    Yeah. I think the, the best remote work tool and app is just the same tools as everyone uses like email and Google apps and all these cloud-based productivity things. But, um, the new ones that are a little bit interesting, which probably aren't so new anymore, is things like Zoom for like really, really high quality video calls and slack for inner team connectivity. That that's pretty cool. I think there's, there's some interesting new tools, emerging tools like Parable for guiding Seamless standup calls pro and retros, uh, which I think is is really cool to put some process in place for some of these more tactical, um, type of things. And, and another thing that I've been looking at a lot, which is very cool for remote work is the GitLab launched their um, handbook and Basecamp just launched one as well, which basically explains how they do work.  

 

Greg:    01:06:13    Um, and they document it in a really thoughtful way. Um, which I think is so cool because companies who aren't remote should be doing this. Yeah. Um, and having very dynamic examples and explanations of how they do things. Um, but remote workforces people to be way more thoughtful and, and way more clear and concise with how they communicate. And so those companies I think are on the forefront on how they organize. Um, but I think all companies will eventually have to utilize the same tools as remote work companies. Just, it'll take 'em a little bit longer 'cause they rest on their laurels with this co-located mentality.  

 

Kristin:    01:06:46    Yeah, sometimes companies don't realize that they are basically remote, whether you're in the same building, it might be an eight story building and every, like, you don't even see people who are outside of your office or your floor and then, or whether you're working in the same town but in different offices or in different countries. Like it's kind of the same. What is your, do you have any like travel ritual or indulgence like maybe at the airport or airplane? Like what is something that you like to do when you travel? Yeah,  

 

Greg:    01:07:20    My favorite thing that I like to do anywhere that I am is get outside and walk around. Um, and so the way that I like to see a city and stay active and keep my focus is to, is to, to really walk around and explore a new place. And so I like to walk five to 10 miles a day. And the way that I do that, which is a little bit indulgent for me, is that I try to prioritize many calls that I do to be video calls, but I, I do a couple calls, um, over voice and get nice data packages so that I can take the calls while I'm walking around a city, which for me is, is one of the best ways to stay in shape, to stay focused and engaged and also to get to explore and enjoy the sounds and the smells and the sites, uh, of a new  

 

Kristin:    01:08:04    Place. I agree. Actually, you just hit both of my next questions, which were how to stay healthy while you're traveling and what is the best way to see a city really fast. And I think you just hit the nail on the head. There's, in my opinion, nothing better than just like wandering through a new city. And I am definitely famous for taking my phone calls like that, whether I'm walking down the beach outside or in a, in a different country. So Love that. What is your favorite destination for leisure travel and what is your favorite destination as a remote work hub?  

 

Greg:    01:08:37    There's so many great locations and I think one of the, one of the best parts is to be able to see new and different, interesting, exciting places. So I do try to get to new spots, but one place I've been going back to again and again so I'll have to bring it up is Mexico City. It's just an incredible city. Great weather, great food, great people architecture and beautiful urban environment with trees everywhere. A really, really special place for me personally. And that's I think, more of a place to, to work remotely and hang out and spend time, which is unbelievable. And one place you really can't beat Southwest Europe spending time in Spain or Portugal or Italy. It's just such a magical place to be. Yeah. They just have such a unique culture and I think that's a great place for me to spend some time, relax, eat good food, have a good time.  

 

Kristin:    01:09:26    I agree. I was journaling the other day and like asking myself some questions out of this book and I was like, yeah, if I were to take some self-care time and take time off work, I would probably plant myself in southwest France or like somewhere in Italy and like a vineyard or <laugh> on the beach or something, which we can totally do. It's just up to us if we decide to go and do it. We're probably both workaholics. We'll take one more question from Corey. And this is actually a, a lead into, to end the interview, we need to know some more data about Remote Year and the cost. Cory's asking how much cash do you have to have saved to be able to start living this way? And then also would like to ask like what are the kind of the monthly prices of Remote Year? And um, guys, I have a link in the video description where you can get $200 off. Um, so if you wanna check it out, it it'll be there for you. That's  

 

Greg:    01:10:22    Awesome. And also if you wanna learn more about Remote Year, feel free to reach out to me personally directly, just greg@remoteyear.com. Happy to chat with anyone who wants to learn more. Um, and Corey, great question on the, on the cost. I think Remote Year was really set up for accessibility, right? To make this type of thing possible for people out of their ongoing monthly paycheck. Um, and we've seen people participating, earning all various ranges. I think you probably need to be in the 30 plus thousand dollars a year range for this to, to work for you. And we've definitely seen people do that effectively and sort of on up from there. But we, at Remote Year we have an ongoing payment of $2,000 and then a down payment depending on what your program is. Our one month programs are a little bit different because it's just one, one payment and they range in the 3000 plus range. So it, it really depends what you're trying to do, how you're thinking about it. But what we like to do is have people participating who don't need to have that much cash saved but are really thinking about being productive, continue to earn money while having this kind of experience.  

 

Kristin:    01:11:29    Cool. So it kind of pays for itself.  

 

Greg:    01:11:32    Yeah, exactly. And we have tools in place again to help you figure out your professional situation. Um, and we really prioritize helping you do that with your current employment.  

 

Kristin:    01:11:40    Nice. I have your website up here, RemoteYear.com where you can read more and work in tropical places. It looks really fun. I need to, um, get over there. Maybe we could do some kind of a swap Greg <laugh> pitching myself on my podcast. <laugh>.  

 

Greg:    01:12:01    Definitely. That would be fun.  

 

Kristin:    01:12:02    I'll make some, I'll make some videos for you maybe next year. Um, I actually didn't, I forget what happened, why I didn't go, but I think I just had other stuff coming up and this has happened to me. I have applied for Remote Year. I'm actually friends with the founder of Wifi Tribe and so, and I also am aware of Hacker Paradise, like there's all these cool work travel programs and I can somehow never seem to coordinate to be in the right country at the right time, but I'm gonna have to make it happen 'cause it just looks so much fun. And I've done a lot of co-living and been to a lot of like digital nomad conferences and events and I've made lifelong friends. I set a goal, actually didn't meet a single remote worker, only expats until 2018 in January of 2018.  

 

Kristin:    01:12:55    I made it my goal to meet as many people in this lifestyle as possible. And I met over a thousand people in one year <laugh> because I went to so many, so many of us. That's wild. So yeah, if you don't, if you're not proactive about it though, you could just kind of drift around without, without a community. So that community guys is so important. So thank you all for hanging out with us today and participating in the live chat. It's been so good to just engage with everybody here with Joy and Abby, Corey Tech, lots of cool people. Walt is in here. Walt and Teklordz are my longtime Patreon patron. So thank you guys and thank you to everybody listening. Leave a review, check out the show notes page for links to everything that we talked about on this episode. And Greg, stay warm over there in Chicago. I hope that we get to intersect somewhere in the near future and thanks for all of the inspiring work that you're doing and helping people become remote citizens of the world.  

 

Greg:    01:13:59    Awesome. This was so much fun. Thank you so much for having me.  

 

Kristin:    01:14:02    You're welcome. See you soon.  

 

Greg:    01:14:04    Definitely. Thank you. 

 

Kristin:    01:14:06    Bye guys. Thanks so much for listening to help support this podcast and help it grow. Please leave a review in the Apple podcast store and send this or your favorite episode to a friend for weekly travel videos, live streams, and even more interviews. Make sure to subscribe to my YouTube channels at youtube.com/digitalnomad and Traveling with Kristin. See you soon. 



Greg Caplan Profile Photo

Greg Caplan

CEO and Co-Founder of Spot Meetings

Greg Caplan is the co-founder and CEO of Remote Year, the world’s largest international work-travel program. After building his first company and having it acquired by Groupon, Greg then founded Remote Year in 2015, which went on to raise $12 million in their Series A round, and now has over 110 employees around the world, generates. Remote Year enables location-independent professionals to live and work in different cities around the world as part of an immersive cultural and community experience. Participants get to work and live like a local for 4, 6, or 12 months in some of the world’s most vibrant cities with a group of other professionals from different backgrounds and industries. For a monthly fee, Remote Year plans all the logistics including flights, accommodations, workspace access with 24/7 wifi, as well as connecting you with locals and planning activities on the ground in each city. And Remote Year has now over 2,500 participants at the time of this recording. Currently, Greg is now the CEO and Co-Founder of Spot Meetings.