Matt Bowles: Hey, everybody. It’s Matt Bowles. Welcome to the Maverick Show. My guest today is Greg Caplan. He 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. 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 four, six 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 Wi-Fi, as well as connecting participants with locals and planning activities on the ground on each city. Remote Year has now had over 2,500 participants at the time of this recording. Greg, welcome to the show. 

Greg Caplan: Awesome, thank you Matt, so excited to be here. 

Matt: My man, this interview in the works for a while. You and I last hung out in person. I feel like it was Austin, Texas. We were both speaking at the South by Southwest Conference. And we hung out at the speaker dinner there back in March of 2019. 

Greg: Yes, sir. That was so much fun. What a great evening.

Matt: That was awesome, man. Unfortunately, we are not in the same place today to do this interview because I was really hoping you and I could have a bottle of wine in person. But you were gracious enough to jump on from a different continent. I’m actually today in St. Petersburg, Russia. And you are where today?

Greg: I’m in Mexico City, Mexico. And I think this is perfectly fitting for us to do this remotely. 

Matt: That’s actually true. Good point. This is a very fitting interview to do remotely. So, let’s jump into it, man. I’m excited to introduce you. And I’d love to start with your background in terms of I know – by the way, I don’t know if you know this about us that we have this in common. But we were both born in the Chicago land area. I was born in Arlington Heights.

Greg: Very cool.

Matt: And I moved when I was very young, so I can’t claim a whole lot of Chicago heritage, but I do have that as my birthplace. But I know you were born and raised there for most of your life. But I would love to hear your story about how growing up in the Chicago suburbs you became so passionate about travel and interested in other cultures. How did that come about?

Greg: Yeah, I think you hit the nail on the head with the description of my childhood. I grew up in a nice little suburban cul-de-sac in a suburb just north of Chicago. And you could probably picture what that suburban cul-de-sac looked like. It was very safe, very nice, very quiet. But what was unique about my upbringing is that when I was 5 years old, my parents met this guy named Salwin Butler. And Salwin was a great guy. He was in his early 20s, and he was from New Zealand and in the states, needed to find a place to stay for a couple of weeks. So, when my parents met him, they invited him to come and stay at our house. And we had such a good time, really hit it off, so much fun with him staying with us that he ended up staying over five years which was such an unbelievable experience. Basically – I have two brothers. He was like a third brother for that time. Still talk to him fairly regularly. And we had such a good experience inviting Salwin into our house, becoming sort of a part of our family that next we had a whole bunch of people from all over the world living with us for various periods of time. We had Evan from South Africa. Then we had Ben and Daniel, two brothers from Australia for a while – for five years. Then Benji and Luci from – guys from North Africa. And then Aaron and Avery from Russia. We sort of had this hodgepodge of people living with us for extended periods of time throughout my childhood which was awesome. Kind of ended up looking like 14, 15 people around the dinner table every night which was kind of a mini model U.N. of craziness. But that really for me opened my eyes to – I think people say global perspectives, but really just how similar people are all over the world. People, I believe, are fundamentally the same at their core. Everybody loves pizza. Everyone cares about being safe and their family and their friends. And there are difference culturally, but at the core I think people across the world are more similar than they are different. That was a big learning for me throughout that experience. And the other thing growing up in an environment with tons of people all the time, it was loud, it was crazy. It was fun. It was also challenging at times. Six, seven, eight boys sharing a bathroom. But for me it really left a mark on me around community. I loved just being around big groups of people. And whenever I do anything, I start with, “Who am I going to do this with, not what am I going to do.” Because that’s where I really learned to thrive as young as five, 10 years old. 

Matt: That is amazing. Wow. And then as you grew older and you started to travel internationally. At this point in your life with all the travel that you’ve done – let me just start off with a very broad and general question. Why do you, Greg, travel? What do you get out of it? What does travel mean to you at this point in your life?

Greg: Travel is an interesting thing. When I was growing up, we definitely traveled a little bit, but I didn’t have the opportunity to spend extended amounts of time outside the country in any real way. I think when I really sort of caught the itch to see what that was like was probably my junior year of college when all my other friends got to go and study abroad and live abroad for a while. And I went to the business school at the University of Michigan. And they unfortunately didn’t allow for us for whatever reason to study abroad.  But I went and visited a few of my friends abroad in Asia and in Australia. And then another trip I took to visit some other friends across Europe. And I was just so amazed with this life that they were living which was interesting and different and culturally exciting – trying new foods and meeting new people and having this amazing life changing experience. Ever since I got to see this lifestyle that my friends created for themselves while they were just juniors in college, I sort of had this gnawing ambition to someday do that myself. And to be frank, I never really had that opportunity. So, after I graduated from school, I moved back to Chicago which is where I grew up again. And worked there for the next couple of years, but during that entire time I maintained this fantasy of having that kind of rich, exciting experience of meeting people with different backgrounds and tasting the foods of different cultures that are more local and authentic and maybe a little more natural and connected. Understanding the different perspectives of these different people and how they understand the world and understand what is going on was such a romantic idea that I had really kept dreaming about, I guess, for the next few years.

Matt: And then how did the initial concept of Remote Year come about?

Greg: Yeah, so as I said, I graduated from Michigan. And I was actually going to come to Chicago to do consulting. I was recruited to Bain. And I had this amazing opportunity to take 10 months, and I was starting this company, and I met this guy in Chicago, Brad Keywell. He said, “I don’t know if this idea is going to work, but you shouldn’t go into consulting. Come and work for me.” So, I moved to Chicago quickly after graduating and worked in venture capital at his firm with his partner Eric Lefkofsky, called Lightbank. And we were investing in all kinds of things. They actually had just started Groupon before that which had grown to a crazy success. And I was working with them on all kinds of different ideas. And then sort of took one idea that I was working on with a friend and coworker, Brian Ficho, called oBaz which was short for online bazaar. Which was a set of ecommerce tools hoping to make it easier for people to sell online, especially through social channels. We grew that for a couple years and eventually we actually sold that to Groupon. And I spent a year working at Groupon. And it was a great place. I had a lot of fun. But I had always had this dream and this idea of getting out of Chicago, seeing what it felt like to live somewhere else, to really get deep and not just be a tourist, but to kind of feel like a local. And this dream kept gnawing away at me. And in Chicago I’d grown up there. I’d been there for a long time. I was commuting every single day into the same office. And it was just a sea full of desks full of people that were – just a lot of them putting in the time nine to five. And I just wanted to get out of there. I wanted to see the world and go and experience more that it had to offer. So, what I did one day was I decided I wanted to find a job that could support me to do this. So, I could do it for a long period of time. And a question that I get frequently is, “How do you find a remote job that will support this?” And my experience which is all that I have at this point is I didn’t know that remote jobs were even a thing at this point. This was 2014. And I didn’t know that it sort of existed. I guess the industry was just kind of starting. So, what I did was I went out across my network, and I started talking to people about doing some freelance work for them and being able to do that obviously digitally because a lot of freelance work is done digitally. And I talked to a couple friends that I had. And the most important day was one day I went through the process. I was talking to one of my friends who had started a company. And they needed some help with some strategy and some marketing. And I said, “I can help you with that. What I would need to do is it would have to be remote. And here’s the amount of money that I would need.” And we talked through it for a few weeks. And one day he said, “Let’s do it. I’m in. Let’s make this all happen. I’m so excited to work together.” So, that day I was so excited that I finally figured this out. I was ready to quit Groupon and go and take this contract and go and start traveling the world while I worked with this company. But again, whenever I do anything, I start with, “Who am I going to do it with?” So, that night I asked my group of best friends, “Hey, do you guys want to get work that you could also do from anywhere because I just got this contract. Do you also want to get work you can do from anywhere and go travel the world together?” And they all kind of looked at me like I was crazy. Because these were consultants. These were investment bankers. These were more typical, less entrepreneurial minded folks. And they all kind of looked at me like I was crazy and said, “That doesn’t make any sense. We are definitely not going to quit our jobs, find some work that we can do and go travel. We don’t know what you are talking about.” So, a little bit sad that I couldn’t convince my group of friends to pick up and do this with me. The next day while I was thinking through this after sort of trying to understand how I was going to make this all work, I put up a very simple website. And crazily enough I put it on the domain www.remoteyear.com which was sort of my vision of what this would look like. And all it was, was a website with an email sign up box and a couple lines of text. It said, “Who wants to travel together for a year while working remotely?” And there was almost no more information. And so basically, I was going to use this to convince some more adjacent friends – not my core group of friends, to come and travel with me. So, I sent it to a couple other friends over Gchat or over email that I think were a little bit more open to this kind of idea. And then all of a sudden, I started to get these people signing up who I had never heard of before. So, apparently the friends that I sent it to had sent it to some other people because it looked a little bit legit enough to share. And then more people started signing up, and more people started sharing it. And the first day over 1,000 people signed up.

Matt: That’s unbelievable. 

Greg: Totally wild. Totally unexpected. I mean literally insane. And then more people kept talking about it. And at first this one journalist at I think Ink reached out to me and said, “This is really interesting what you are building here. I’d love to write a story about it.” So, she wrote a story about it. And then more people started talking about it. And more people started putting in their email addresses. And then more press started reaching out. And there were more publications in the U.S. And then started to get inbound inquiries from press abroad. And over the next couple of months as this just kind of snowballed, over 50,000 people had signed up all over the world. And at that point, it was still a very simple website with a couple of lines of text and an email signup box. Which is wild and totally unexpected and amazing. And that’s when I started saying, “There’s something more here. There’s something more than maybe my sort of sad attempt to find friends to come travel with me. There’s something that we hit on.” And that’s when we decided to really sort of formalize things and make this into more of a program that can help people who seem to really want to have this kind of experience do that. And at that point, it was very unclear what we were; what we were going to do, how it would work, where we would go, what it would cost, what it would include. Nothing was set. This was just kind of a couple of word and ideas. So, thankfully, one of those friends that I tried to come with me in that original night – his name is Sam Pessen. And he’s been my best friend for the last ten plus years. He was my roommate in Chicago. He actually was a consultant at Bain. So, he’s a super operational focused, detail oriented, amazing human being who actually had an amazing relevant upbringing. He actually grew up as the son of a journalist which means that he was living for a couple years at a time all over the world in different places. So, when he was born his parents were living in China. They actually got kicked out a couple months later while he was a baby because of the – after the Tiananmen Square massacre. They kicked all of the journalists out. And one of his first claims to fame was that he actually, with his mom, were on the cover of the Beijing Times or some Chinese newspaper as they were kicking all the journalists out. He was on the cover of the newspaper as just a toddler – or a baby. And then he lived in D.C. He lived in London. He lived in Jerusalem. So, he kind of is a little bit better of background for starting something like Remote Year. So, anyway long story short. He was my roommate at the time. I had originally invited him to come and travel with me. After he said no, put up the website for Remote Year. It got at all this interest and excitement. And throughout that process we were sitting together on the couch, having whiskeys, talking about how crazy all of this was. He naturally sort of moved into more of the operating capacity. He was thinking through more of the details of where would we go? How would this work? How would we structure this? What would it include? Where would we go – like all these different details that he started putting together. And so naturally as this kind of evolved, it was clear that he was going to help me build this out and make this sort of dream that I had into a reality. And so, we together over the next couple of months really refined all of the sort of high-level details. A funny story, our original itinerary that we had put together was going to 18 places for between two and five weeks each. I don’t know why we decided to do that. But we did. And we had committed to releasing our itinerary on I think it was December 1, 2014. So, a few hours before we had released our itinerary, we were looking at the itinerary and at the last second made a couple changes. Which is wild to think about now that we would do that. But we did. And we changed it from 18 places to 12 places and said it would be better to go to a couple fewer places. And we looked at it and said if we’re going to go for a year, we might as well go to each place for one month. And so that was one of the decisions that ultimately looking back was an unbelievable decision. Thank god we made that decision. Because going to each place for a variable amount of time would have been a total nightmare to plan logistically and do. But I think that speaks to the idea that we were just making decisions on the fly because this was a brand-new idea, brand new way of working and living that we were trying to create some structure behind to help that be a possibility for more people. So, over the next few months we continued to refine exactly how it would work. We eventually said, “Okay, now we have 50,000 people who have signed up. How do we decide who’s going to come? And who were are going to invite to join us?” So, we spent a long time really thinking about how we would decide who would be a good fit for our community. So, we next launched a series of essays that we requested people fill out, “Why they would be a good fit for our community? And why the community would be a good fit for them?” We read through all those essays, and then got on the phone with over 600 people to meet them, to talk to them, to understand what their background was, how they would be a good fit in our community and if this would be a good fit for them. As we sort of went through that group and kept refining more of how this concept would work, we started offering people a place to join our inaugural group. And eventually on June 1, 2015, we all hopped on a plane, us included and our initial group of people, and our first Remote Year began in Prague. Which is an unbelievable thing that people trusted us to get on a plane and show up, and all they had ever seen was that simple website online and had a 30 or a 60 minute video chat, at that time over Skype because Zoom didn’t exist, with two sweaty guys in black t-shirts in their living room in Chicago. Totally wild.

Matt: Well, my good friend Trevor Gerhardt who was part of that inaugural group, the OGs. And I think he was literally the first single person to get off the plane in Prague. Tell us the story of how – exactly what you just said. He’s like, “I signed up on some website and gave somebody $5,000.00 and bought a ticket to Prague. I sure hope somebody else is going to show up here and I didn’t just get scammed.” But obviously I think it was you personally who was waiting there at the airport with the Remote Year banner and all of that stuff. But could you take us back to that time when that materialized and it became real – the excitement there, but also the business challenges and trying to fulfill on such a huge offering which I can only imagine how insanely cumbersome that must have been the first time. And then maybe take us from that first –what was the difference between the first Remote Year group and today? Now I was on Libertatum which was group number seven. So, we went – I did the 12-month remote year program of a little over a year after you launched the first one mine started. So, there was obviously some progress between one and seven. But between seven and today, there has just been an enormous amount of quality control and infrastructure building and all that kind of stuff. So, I would love to get your perspective on how the first ever group went and then what the lessons were from that. And how evolved the company until today.

Greg: Sure, so I’ll take you back one step before that. So, like I said, when early days Sam and I started building together what this would look like. It became clear as we were talking to folks and starting to plan out the first Remote Year that the two of us would not be able to do this alone. And we brought on our initial group of our team – our initial team of six people. And there were four other folks. There were Will and Trish who were vaguely brought on to help with what we call the operations. We had Hannah who was our community manager for our first program. Now we call it program leader. And we also brought on Jesse Gross to help with all kinds of things and in particular thinking about some of the future work stuff and how we work with companies. Because that’s been a focus since the beginning.

Matt: Greg, just to give people context. Like how old your whole team was at this time? Just the age range of you guys so people can get a context.

Greg: Yeah, we were definitely a green bunch. Sam and I were both 25 when we began. And then Jesse, Trish, Will and Hannah were all within two or three years of that. So, everybody in their early to late 20s trying to figure out how to make this all work. 

Matt: Exactly. All right go ahead. Just wanted that context. 

Greg: Totally. So, we brought that team together. And ironically, we were working remotely because these were all folks were just saying, “This is exciting. This is interesting. I just want to help out however I can.” They were helping out with all kinds of random things before we kind of brought them onto the team. Will actually was still working with Accenture the first few months of Remote Year as he’s also part of our team which was a wild experience for him. He was working his butt off at that point with a job at Accenture and being part of the team building and on Remote Year. And so, we all converged in Prague about a month early before the first program began. And ironically, we were a fully remote company. And at that moment became a collocated company for a short period of time trying to build Remote Year. So, we got to Prague about a month early for what we called setup. We had built the relationships with most of our accommodation’s providers. We built our relationships with a coworking space called Locus. But we were coming in to check and make sure they had all the things we needed to deliver on the promises we made. So, we created all these checklists and all these processes. From just intuition to try to hopefully take these hotels and apartments and dorms and coworking spaces that we’d found through making connections online. And hopefully to ensure that they met some level of standard and specifications that we were setting for ourselves to try and make an infrastructure and experience and a program that could help people be successful, work remotely while traveling the world for a year. And so, after a couple weeks of what we called setup, then we were in the moment getting ready for people to start landing. So, we were creating process. We asked everybody to send us their flights of when they’d be getting into Prague. And they were getting in at various times between Saturday, Sunday, and Monday of that first week of the program. And so, we decided what we would do is we would wait for them at the airport with two of us, Hannah and I, waited at the airport. We made a sign that said, “Remote Year, welcome to Prague.” And we were the greeting crew. And so, whenever people landed, we tracked their flights. We’d meet them at the exit with our sign. And we’d run from area to area of the Prague Airport greeting people. And then we’d bring them to a little sprinter bus that we had the next team waiting for to bring people from the airport batched with a couple folks that also got in. Get to know each other, meet each other, and then print them to their accommodations. So, that first group – like you said, Trevor was the first one to land. We had our little jinky sign that we held up. We met him for the first time in person. And we gave him a hug. And we brought him over to the bus to meet a couple other Remotes who were landing shortly after him. That was sort of the start of our first program Remote Year.

Matt: And how did the first year go? And what were some of the challenges in the first year? What were some of the lessons that you learned? And then how did you build it from 2015 until today? What’s been the evolution?

Greg: So, that first month we just had such a great time. It was such a high. We were all so excited about this group of people were amazing. We were doing all these fun activities and events. We were pioneering this new future of living and working. And it was just so much fun and exciting. Prague in June, as I’m sure you know, is beautiful. We were having the best time. And then we were transitioning from Prague which was the first month to Ljubljana. And Ljubljana is a beautiful city, and our events team went there and the accommodations that we found were a student housing facility right in the downtown area of Ljubljana. But it’s sort of a Soviet feeling student housing facility, and so we transitioned from Prague to Ljubljana. And it was a bus ride – about an eight-hour bus ride that took us from Prague to Ljubljana. And we left in the morning – we were a little bit late getting out. The bus ride took a little bit longer. People were tired from a long day of travel. We got there at night. And everyone kind of got off the bus, and it was dark out and the building looked kind of dreary. And everyone sort of got in there and looked around – and it was kind of dank looking especially at night. And you could feel the mood of the group sort of start to deflate. And people sort of altogether recognized this is going to be a year. We committed to a year. It’s a long time. These guys – the last place I stayed might have been nice, but this place looks like it’s not so great. Like, “What did I get myself into? Am I really okay with this?” And so that first year as we evolved into that month in Ljubljana which was July, a record setting heatwave. And a student housing place that was not so nice and didn’t have HVAC or air conditioning. So, people were hot, and they were uncomfortable. And there were a lot of little things that definitely made it difficult to be successful working remotely and having a good time. Even though the city was beautiful, there were some challenges with the workspace. There were a lot of challenges with the housing. And the sentiment of the community started to really move toward a move negative feeling that month. And that was sort of the beginning of a much more skeptical, a much more difficult process that happened throughout the rest of the next few months with that group. They were excited about living and working but starting to get increasingly frustrated with the fact that we didn’t know the right way to plan perfectly in all of these places. We were in some accommodations that were hit or miss. We were in some workspaces that had some problems. We had all kinds of things that frankly a group of six Americans running around the world trying to set up and hospitality experiences that were catered to folks being successful for working remotely didn’t always go that well, to be honest. And throughout that year – that group was an amazing group of people, most of them stuck with us throughout the entire journey. And just through sheer will and faith they stuck with us. And the crazy thing is that although that was challenging and difficult throughout many periods of time, that was just an amazing group of people. They are so connected to each other. So many of them I have such a great relationship with still today. We learned a lot. Taking that forward, that year was really can we make this happen? Is this even possible? And then the theme of the year after that was, “How do we really build this into something that is a little bit more institutionalized, a little bit more structured and a little bit more reliable?” Like what is the right way to do all of these things. So, we had our core offering. We are offering housing. We are offering workspace. We are offering events and activities. We are offering community, and we are offering travel. And I think the next year we really then had the opportunity to bring on a much larger team to really build out, “What does that mean? How do we offer and build housing that can help people be successful working remotely, to have a great local immersive experience, authentically but also consistently? How do we do that with travel and workspace and events and activities.” So, that next year as we had more communities join our program, it was really about how do we take this sort of really wild, bleeding edge complex experience and make it something that is a little bit more streamlined and consistent and high quality for people throughout their experience. 

Matt: And how did you guys end up doing that? So, today when someone joins Remote Year, what does the experience look like versus the first one with the OGs today. When people join Remote Year for an upcoming trip, what does the quality control, the economy of scale, the infrastructure, what does the experience look like today? What have you guys been able to do with those lessons you learned?

Greg: Sure. So, it starts even at the beginning of the journey. And our program placement team, we call them program consultants because that’s really what they are. So, when people come to us and want to come on our program, the first most important thing is we spend a lot of time with people making sure that our program is a good fit for them, and they are a good fit for joining one of our programs. And that’s everything from their professional situation, their work situation and also their motivations. Why do they want to come on the program? What are they hoping to get out of it? And then beyond understanding what is a good fit for our program based on a couple of years and thousands of people, the next thing we do is we help people actually then take the next step. So, before everyone had to figure out their own professional situation on their own, and from day one there have been a whole lot of people who’ve said, “I’d like for you guys to help me figure that out.” So, over the last year and a half, we’ve actually built an entire team who we call the Employer Solutions Team. And their whole job is to help people that want to come on our programs and work full time for a company go through the process of getting permission together hand in hand, to get permission from their employer. So, we have built out best practices from all the thousands of people who have done this and bring them to bear, and help people really navigate that process successfully. And we have a really high success rate with people who actually want to go through that process and get that permission. And able to actually do it through the processes we built out. And that’s been a really exciting evolution for us as an organization to help more people make this a reality. 

Matt: Awesome. 

Greg: Yep. So, the next part of their journey when someone wants to come on our program is onboarding. So, they decided to come on the program, then all these questions arise. And from day one, there’s been a lot of consistency in these questions. Right? What do I do with my apartment? How do I think about packing? What immunizations do I need? What visas do I need? How do I think about healthcare on the road? How do I think about insurance? How do I think about all these different things? And again, we’ve had thousands of people come on our programs. And we also have a full-time team as well on – what we call the onboarding team, to help people go through all the different processes to get themselves ready to go and embark on this journey which is a very complex thing to do. And our initial group of people all had to kind of figure it out themselves. But we’ve centralized a lot of those learnings and processes into whole big set of resources and an entire team to help people actually then go from deciding to go on our program and making that as seamless as possible to actually begin the program. So, that’s the second thing we do. And a big part of that in addition to all the logistics is meeting your community. So, we actually have a bunch of different ways digitally that we bring the community of people together to start getting to know each other. And planning and having fun and building relationships before they actually set foot on the ground on the first day of their program. Because at the core of everything we do at Remote Year, ever since the start of the first day, the core of Remote Year has been people having this experience together. And that’s what’s really unique about traveling with Remote Year versus doing it on your own is that you are joining this community, which is so hard to communicate the value of, but is for me so foundational to what makes this exciting and fun and also comfortable and safe and a little bit more familiar.

Matt: Yeah, that was the primary motive for me day one as soon as I saw what you were offering. Because I had already been a full-time digital nomad with no permanent base for two and a half years prior to doing Remote Year. And as I was traveling around the world – and I was in a relationship at the time for those two and a half years. I was traveling around with my partner. And then she and I ended up breaking up. And I was like, “Well, I’d really love to keep traveling because I love this lifestyle. But I urgently need to reinsert myself into a community. Like, I need people around me.” I was really a mass social void. And I had heard about Remote Year. So, I immediately went to the website, and I was like, “This is it. This is the solution for me. This is exactly what I need right now. I can keep traveling, and I can do it with a community of 50 plus people who are going to travel with me for the entire year and be together with me. That’s exactly what I need right now. I can keep traveling, and I can do it with a community of 50 plus people that are going to travel with me for the entire year and be together with me. That’s exactly what I need.” And that’s literally – I mean by far – logistics are nice, and you handle this for me. And all of that stuff is nice, but it’s totally secondary for me. The community was the whole game.

Greg: 100 percent. And you know my experience was the same. I was getting ready to go travel, and I was really yearning for a community. And it just didn’t exist out there. There wasn’t a way for me to do that. And that sort of personal need is why I put up that somewhat sad website that has become Remote Year. So, that I think is the core. And I think that community number one makes travel more palatable, more comfortable in a lot of ways. And then also the relationships that I have built and that most people in this community have built through that shared experience is just so different than any kind of relationship that can be built I think at any other point in people’s post childhood career. Like after school there’s almost no opportunity for people to have these kinds of experiences and build these kinds of relationships. Which I think is one of the most special things about Remote Year. 

Matt: 100 percent. And these are the types of conversations that I have with people. And I say to people that live in a particular city, I say, “Think about your top three closest friends that you have in your city, not including people that work in your office, right? Your top three friends. How often do you actually see them physically in person?” Right? And maybe you take your number one friend out of the equation. How often do you see friends number two and three? And most people are like, “Once every three weeks or maybe once a month maybe we get a coffee, we get a dinner, or we catch up.” This kind of thing. I’m like, “Right, exactly. So, you see like your closest two or three friends once every two to four weeks. So, you see them maybe 12 to 24 times a year.” On Remote Year, you see these people every single day for 365 consecutive days. Like the depth of the relationships and of the connection is just absolutely incredible. And with our group, everybody that finished that program through 12 months, that’s family for life. We still have two years after the program finished a group chat where we message each other literally every day. I mean people I’m messaging every day in our group chat. It’s family for life. And we continue to connect up around the world and see each other in organized trips together and all that kind of stuff. And it’s just absolutely magical; truly, truly special experience because of the depth of that. It’s just so unique to be able to do that as an adult. To be able to have that kind of community building opportunity, it’s just truly incredible.

Greg: I agree with that 100 percent. And that is the key of Remote Year. It’s hard to communicate to people who haven’t experienced it. And we’ve been trying to figure out ways to do that. But to be honest, it’s just such a complex special unique thing that it’s unbelievable.

Matt: And the thing is it’s not just that you are seeing people with a high level of frequency, but you are experiencing extraordinary things together. 

Greg: Exactly.

Matt: Right? So, you are seeing the world, and you are having lifechanging experiences. So, you’re conquering fear barriers. You are having totally new and exciting and exhilarating experiences. You’re going through hard times in life and being there for each other. It’s this entire rollercoaster of life. Of course, regular life plus all this amazing, extraordinary things that you are doing and experiencing together. And that connects you and creates such a meaningful community bond. It is truly an amazing experience. Best year of my life I tell people was the year I did Remote Year for sure.

Greg: That’s awesome. One of my big regrets in life is that starting Remote Year meant I could never truly be a remote and be on one of the programs because I would always have this staff hat on. I would love nothing more than the opportunity to actually be a real full member of one of these communities because it’s just such a magical thing. And I’ve only been able to observe it from the sidelines which is such a shame.

Matt: Let’s go a little bit deeper, Greg, into Remote Year as you’ve built out the company and sort of thought deeper about what you really wanted the company and experience and the community to be about. I just want to start off by reading from your website your mission statement and your values. And then give you an opportunity to kind of talk about those. It says, “Our mission is to create a more peaceful and productive world by fostering genuine human connections across diverse cultures and people.” And then your values are, “Work life flexibility. Global perspective. Empathy, community, being present and dreaming.” Do you want to share anything about those?

Greg: Yeah. I think our mission has always been something that is super core to what we believe in and why we are doing what we’re doing. From the early days, it always felt like what we were doing was good. And it took us a little bit of time to formalize why we thought what we were doing was good. And at the root of it kept coming back to this idea that the unique mix of remote work and travel has empowering opportunity, right? It empowers people who otherwise wouldn’t have the opportunity to have this experience otherwise to have this experience. And what this means is that it makes this kind of global living, global travel accessible to a much larger group of people. And that is I think the core of what we are about. And the question has always been, “Why is that good?” Giving people this accessibility to have this opportunity. And if you think all the way back to the beginning of humanity, right? Humans have started as a uniquely social being. Humans were not – they didn’t have the sharpest claws. They didn’t have the longest teeth. They weren’t the biggest animals, but they were super successful as a species because they were able to work collaboratively together in social structures. And that’s the most profound thing about humanity. And so, it started as small groups of hunter gatherers, a dozen or a couple dozen other gatherers working together for protecting each other from threats and for helping each other find food and sustenance. So, working together for safety and for productivity in a way. And over the course of the history of humanity, that nature of humanity has continued to evolve and expand. First it was hunter and gatherers in a few dozen, then it you had people organizing with agriculture into communities of a few hundred. And then city states of a few thousand. And over time those structures evolved again for people to collaborate over a much larger group of people through new social structures and devices they built like money and laws and writing and standardized communication that allowed these structures to get larger and larger. And what that was doing was it expanded this notion of us. And this notion of us was us versus them. Us was this group of 12 people and them was everybody else that could be a threat. And then us was this group of 1,000 people and them was everybody else and animals and everything that could be a threat. And the notion of us then expanded again from city states to nation states of a few hundred thousand people. And then millions of people and then you have these things like the U.N. and G7 and – that expand the notion of us amongst even larger ideologies to include billions of people now today. Right? And this notion of us throughout the course of humanity has been expanding fairly linearly. There are definitely some reversions, and it goes down as people put up new divisions and borders. But I think the general arc of humanity is this constantly evolving and expanding notion of this idea of us. And what us means is people that are on my team and similar to me in a way that we can work together in order for us to be more sustainable and thrive as a community. And them has always been the enemy, the other. And I think as we look towards that trend, I believe eventually this notion of us is going to span the entirety of humanity. And the reason why I believe that is as you look towards the long arc of history, that’s been the direction things have evolved. And I think that the threats are no longer other humans like they used to be, but they are much more existential. They are things like global warming. They are things like mass disease and hunger. And all of these big problems that humanity needs to band together into a much larger notion of us than we have today in order to attack those things collaboratively together. And so, if you believe that is the larger arc of where humanity is going, then the question is, “How do we get there?” And I believe the only way for humanity to work together peacefully and productively is for everybody on the planet to have these kinds of profound experiences where they understand the similarity and connectedness of all humans on the planet. And I think that’s exactly what Remote Year does. It gives people the accessibility to have the opportunity to go and live across the world in a very different place, to have the core insight that the people there are just like me. 

Matt: Can you also talk about the positive impact initiative – maybe you can even start by thinking about this broadly in terms of what are the ethics associated with international travel in terms of being an environmentally responsible, socially responsible traveler. And how has Remote Year integrated that into the program through the positive impact initiatives. Maybe just talk a little bit about that.

Greg: Sure. So, I think there are definitely some complications with travel. There are also lots of benefit. Travel is one of the largest industries in the world and contributes meaningfully to lots of different economies. But the challenges are definitely real, and they are profound. The environmental impact is one. The more important one that we like to think about is the community impact and how do tourists become valuable members of the communities they travel to? And that’s something we spend a lot of time on. And positive impact, being a positive community members of the communities that we are in is very, very important to us. And because of that, we don’t do sort of positive impact on a global scale. We don’t believe positive impact should be done on a global scale. We do it on a local scale. And so, we have teams in each of the cities who are super patriotic and excited about their communities. And they spend a lot of time in the community in understanding what they problems are through talking to people. And understanding how we can be valuable members of those communities. And so, in each of the communities we are in – we are in 12 different communities right now. We have different relationships on the ground with different causes. And in some places that is things like building houses. And we did a humongous contribution in Peru where we built a bunch of houses because they were having all kinds of problems after a large flooding incident. And in some other places like Mexico City there’s a whole lot of stray dogs. And that’s a cause that our local team is passionate about. And we have people go into a local dog shelter and spend some time with the dogs, go take them for walks because there is just a humongous amount of them locally in Mexico City. So, we have these relationships on the ground long term with causes and with organizations that we can contribute to as an organization but also make that opportunity available to our remotes throughout each month while they are on the ground. And sometimes that looks like doing things that are more manual labor; painting walls, doing construction, walking dogs. And a lot of times that’s getting in there and learning about these organizations and what their needs are. And it could be things like building a marketing plan, building a fundraising plan, helping them build out their website and their CRM strategy. And so, we have these amazing thoughtful, intelligent, skilled people who are going all over the world. A lot of times they actually contribute the unique skills that they have to really level up these local organizations that are combating pressing, really meaningful local challenges that are happening while they are in each city for the month they are there. 

Matt: One of the things that was really amazing to me on my very first month of Remote Year which was in Kuala Lumpur Malaysia is you don’t really know anybody. You’re just kind of meeting people still the first week. And they offered us the very first week this positive impact opportunity. It was like, “How many people want to go and volunteer to teach these refugee kids in this school of refugees locally there in Kuala Lumpur. And literally I think like everyone’s hands went up. They were like, “Oh, I’ll volunteer,” like the whole entire group. And so, it was amazingly inspiring to me to see how much people want to contribute. And either through a Remote Year company organized connections and infrastructure or even independently. I remember that the Yugan group that I got to hang out with. When I was an alumni, I got to hang out with them a bit. And when they went down to Colombia and just started doing this massive house building project probably similar to the one you mentioned in Peru. But this one was in Colombia for homeless and disadvantaged people at the behest of the local community obviously. And just launched this massive thing. And people from all these different Remote Year groups started contributing money and started supporting it. And it just became this huge thing. And so, it’s been really, really exciting to see how passionate the number of people are that do Remote Year for contributing to the different areas where they go.

Greg: I totally agree. That Yugan Build project was one of the most inspiring things I’ve ever seen before. And the community I think is so powerful in collaborating. I think that example you brought up of all the different communities contributing to that Yugan initiative is also one of the most special things. It’s crazy that there’s people who’ve never met each other but have been connected through this shared experience of Remote Year and have these digital platforms to connect and collaborate are able to come together and make something like that project happen. It definitely speaks to the passion that we have across the community for giving back and for contributing, but also for how cool it is and how powerful that shared experience and that community that has evolved on top of it. 

Matt: Can you talk a little bit about the citizen program? Because I think one of the things that I’m always talking to people about when they ask me about Remote Year, in addition to talking about the actual 12 months and the people in your group, and this is what the experience is like. The much larger, much longer-term picture of things is that you are becoming part of a massive now 2,500 plus people global nomadic ecosystem that is connected in really extraordinary ways. Can you talk a little bit about what that citizen program is as well as sort of what the nation is and how the slack channels are structured?

Greg: Yeah, sure. So, we call our community the Remote Nation. And this is – I created a very intentional framing. We believe in ourselves sort of as a large community of people who are distributed all over the world. But we call it Remote Nation because we are a very intentional community in that way. And when people finish their program, they become what we call a citizen in that Remote Nation. And that terminology is very intentional because we believe that connectivity between these people should feel like they are part of that same nation, that same nationality. We have this unbelievable community of people that have finished our programs and are part of that nation or citizens of that nation. And over the last few years, we’ve been really building out what are the opportunities for people as citizens to continue to stay connected to that community. And we’ve spent a lot of time building out that opportunity. It started with what we call global access. And that was the opportunity to join in with any of our communities on a month-to-month basis wherever we had them available. And our citizens are some of the best influencers in our community. They come in; they get to meet everybody. Everybody gets to learn from them. They get to build these relationships. And that was just incredibly successful. Lots and lots of people were doing that. But the citizens said, “We want more. We are already meeting up with each other. We are already connecting with each other locally. We are already planning all kinds of positive impact, and we are doing all kinds of different things like organizing dinners and having networking events and having shared activities. So, we spent a lot of time talking to them and understanding how we can support that excitement, support that community in more interesting and profound ways. The next thing we launched what we call Citizen Houses. And that’s where we bring people together for specific times in places that we don’t have existing communities. And that is in sometimes beach locations. That’s sometimes mountains. That’s skiing. That’s all kinds of really interesting and exciting things. But the core of that is a community of people coming together. And we’ve gotten great response from that. People are really excited to do more of that. And so, we have a whole bunch more that we’re planning around that. The next thing people wanted to do as part of this Remote Nation, as citizens of our Remote Nation, was come together in a larger format. And so, we actually rented an entire camp outside of New York City for everyone to come together and spend a few days meeting each other, having fun, connecting, collaborating. I’m so excited to see what that looks like. That’s happening in just a couple weeks, the second week of September, which has been really awesome. We’ll have a couple hundred people coming to that. I’m coming to that. It’s going to be so much fun. And the citizen’s opportunity to connect people and continue to build – Matt, we talked about this when we were together in Austin. I have a long term dream of having clubhouses in cities all over the world for our nation to use to come together and build relationships and have fun and do all kinds of things that are professionally focused and adventure focused to really continue to build the community and have ways for them to connect and to meet and to stay engaged with our nation. 

Matt: Well, it’s amazing too because everyone is on slack. And so as soon as you get into Remote Year, your group has a slack channel. But then you can join all these other slack channels. And then when you are an alumni, you have access to the entire nation. And people are just creating all of these different slack channels based on shared interests. So, who is interested in scuba diving? And there’s global scuba diving trips being planned. Or who’s interested in entrepreneurship? And who’s interested in this? All of these different things are going on. And the other thing that is amazing is how you can use that to connect with people anywhere around the world. I was just two weeks ago in Tbilisi, Georgia. Had never been there, it was my first time there. And I knew one person that I was meeting there. Katy Fowler from Battuta was going to meet me there. And I knew that she was going to be there. So, she and I were just going to go Tbilisi together. And I just threw a message out on the Remote Year citizen’s channel. I said, “Hey, is anybody else in Tbilisi?” Ten citizens, Greg, were in Tbilisi the exact same week that I was there. We had a dinner with 10 Remote Year citizens in Tippalesse. And similarly, last year I was going to Nairobi, Kenya which these are not cities Remote Year has ever been to, has anything to do with, is not in anyway involved with. I was going to Nairobi, Kenya and just threw something up on the citizen channel. I said, “Hey, does anybody happen to be in Nairobi, Kenya in September?” And six people were like, “Oh, I’ll be in Nairobi.” And we had a six-person dinner in Nairobi. So, the way that the ecosystem of the whole community globally is just evolving is just incredible. Because now everywhere I go there are people no matter where it is.

Greg: Yeah, it’s unbelievable. That’s so cool. I can’t believe there were 10 people there. That is wild. I think that is so true that the main way this community comes together is digitally. We use slack for that. And it’s so cool that anywhere you go that there’s people in this community that are there and also willing to spend some time together and are going to be interesting and fun and share that experience. One thing that we do that I actually love also is dinners around the world. We organize across the world one night every few months a dinner around the world. And we have people in every city no matter where they are all come together and have dinner together. And we take pictures, and we send them around. It’s just such a fun thing to do to all sort of connect wherever we happen to be. I think there’s a lot of really exciting opportunity for us to continue building that community and supporting it in interesting ways. I’d love to create chapters in cities that we have more density of citizens in to have more opportunities for them to stay involved, to get to know each other, to do fun things together. And that’s something that I would love to start building out as we look towards the future. 

Matt: Awesome. I also want to ask you about another initiative that Remote Year has undertaken, the diversity, equity, and inclusion initiative. And I was wondering if you could talk about that in terms of what inspired that, why that came about and what you mean specifically by diversity, equity, and inclusion. And what that looks like for Remote Year moving forward.

Greg: Sure. At our core, Remote Year is all about inclusion. It’s about having these experiences where you can understand and empathize with people from all different backgrounds and experiences. That being said, diversity, equity and inclusion is very hard. It is challenging. And to be frank, Remote Year was started by an American, me. Our team is very healthy amount of Americans. And we do have people from all over the world on our team, but there are a big number of Americans on the team. And we’ve created a product offering that is fairly focused on Americans because that’s the background of a lot of the folks on our essentially marketing team and our content team and things like that. And so, we definitely have had less diversity across our team and our programs than we potentially could have. And that means at times we haven’t created as inclusive an environment as we possibly could. And to be honest with you, we’ve got negative feedback on that at times from different people who would like a more inclusive and a more diverse community of people on our team and within our communities. And that’s very hard to hear. And it takes a lot of sort of self-awareness to take in and understand and listen. And as we’ve been listening, we’ve been hearing that there definitely have been instances where we have not created an inclusive environment for everybody, and it’s been challenging for folks at times. And so, we decided over the last few years to double down on our investment and our focus on creating an inclusive environment for people no matter what their background or experience is. And that starts with learning and listening and understanding how we’re not being as inclusive as possible. And second is we brought in experts, external experts, to help us build content and curriculum and trainings for both our teams and for our communities. Every new community goes through an inclusivity training at the beginning of their program. And then we have different structures to help reinforce that notion of inclusivity throughout everybody’s journey. So, it’s a focus that we’ve had. It’s something that we’re working everyday to continue to evolve, but we’re definitely conscious of the fact that we’re not perfect. We don’t think that we’ll ever be perfect. And that means that we always have to keep working on it and building and evolving.

Matt: And can you talk a little bit about what some of the results of that have been and some of the development that you’ve ultimately implemented. I guess both in terms of internal hiring as well as the community dynamic in terms of the Remote Year groups. And as well as people’s experiences on the ground in different cities and what those local city specific orientations look like. What is that now – what are we four years after the founding of Remote year? What today does the diversity, equity and inclusion experience look like?

Greg: Yeah, so a big part of that is we start every program off with a deeper training. And we also have a touchpoint before people get to each city where we have a city preview, and we bring them up to speed with the different things that they should understand and know about each of those cultures. And a part of that is understanding some of the DEI concerns and differences amongst different cultures. And we do definitely facilitate that also within our communities as well as their relationship to the external community they are in. It’s hard to measure the results of DEI. I don’t think there is sort of a super metric or key performance indicator that sort of shows that we’ve created a more inclusive culture. But definitely we have seen that the number of complaints have definitely diminished. And the feedback qualitatively on these initiatives has been really, really positive. And we think that we are anecdotally are moving in the right direction. But I don’t think there is sort of a milestone that we’re going to hit where we are going to say, “All right, we’ve accomplished that. We now have created an inclusive environment, and the work here is done.”

Matt: Right, it’s an ongoing process for sure. Let’s talk a little bit now about how you see the trends in terms of the future of remote work. And what are we experiencing right now at this point in history? Is this a permanent macro shift in terms of moving towards more remote work. How big do you see the market now, and how big do you see it getting for let’s say Remote Year’s offering for example?

Greg: I love this topic. I think about the changing dynamics in the workforce all the time. And I think it’s definitely a mega trend. When people talk about the future of work, frequently they talk about technology, right? Productivity is moving to the cloud. Communication is going digital. We are doing a podcast across the world through a web browser which is kind of wild. And that’s sort of the way most work happens. Everything is getting automated. So, technology is having this profound effect on work across the board. But I think the more important trend that is actually happening is cultural. And what I mean by that is that increasingly in a world where technology enables people to be more effective and more impactful than they’ve ever been, it comes back to work is people doing things, right? And increasingly the best people have more of an impact than they’ve ever had. And so, what that means for companies is that they need to figure out how to recruit, retain and engage the very best people. That is the most important way to win in today’s business environment. And if you ask the best people, “What do you want?” They want to work where they want, when they want, how they want and on things that they find inspiring. And that is the critical thing that is happening I believe in the workplace today and the talent wars that are happening. So, the best people by demanding to work when they want, where they want and how they want are getting that from employers who are fighting and battling each other to attract those top people. And the way increasingly that these companies are doing it is they are offering different levels and different kinds of flexibility for those top performers. And what that’s doing is it’s causing the best companies to make a pretty critical decision. Either get onboard with the flexible workstyle the best people are demanding. Or lose out on top talent that will go to some other competitor that will eventually win against you because of the top talent they are able to recruit. And so, what that’s doing is it’s taking this conversation around flexibility of all kinds and it’s elevating it from what used to be the bowels of the HR department and elevating it now into the board room of companies across the world. And these companies over and over again are making the decision to embrace this kind of flexibility in new and interesting ways to attract and retain the best people. And it’s then percolating down into companywide policies or process or procedure that is impacting more and more people. And it’s become quickly something that is now not done on the fringes but has become mainstream. So much so that now 52 percent of the U.S. working population now works at least part time remotely. And part time remote is defined by at least one day a month working out of the office. So, what we are seeing is that this way of working, this flexible, distributed, remote way of working is quickly becoming a mainstream thing. And I think as we look towards the future, it’s only going to become more in demand by the top people and down. And more and more companies are going to utilize this as a way to recruit and retain them. And it’s just going to become the way we do work.

Matt: Can you give some examples? I know some pretty large companies have connected with you guys and actually offered the Remote Year opportunity to potential talent that they are trying to recruit as a benefit. Can you give some examples of how that’s gone for what companies? 

Greg: Sure. So, we’ve had people participate in our programs from a few hundred different companies which is so cool to see. And it’s in some cases gone incredibly well, and in some cases, there’s been some issues. And I think most of the issues that have stemmed from this is that there are too many people that want to do it. Sometimes a company will offer this to some of their top performers, and then a whole bunch of people want to join the experience. And the company then gets a little bit scared of what that reality could look like if they are not ready to make that full leap. And they have in some cases pulled back on it. But in most cases what we see is people have gone on the programs, they’ve been successful doing their job. They’ve been getting promotions. They’ve been getting all kinds of great feedback. And we’ve seen more and more people coming from a lot of those same companies. We’ve actually seen much growing percentage of people on our programs coming from companies that have already had people on the programs. Over the last few years, that number of people has been growing over time. So, a lot of the companies have been successful. And in most cases what we’ve been seeing is it comes from somebody who wants to come on the program. They work with the company to get that permission. They blaze the path for opportunity for more folks to come, and then we see more and more people from some of those companies start to join. I think another interesting thing as we talk about the future of work and how that works within companies – you know, once a company gets to certain size, maybe 100 people, they usually don’t all work together in the same office. They have two offices. They have some people be remote. And what that means is that the organization is therefore distributed. And that means that their base case, their expected form of communication, is digital. Right? If you are not all in the same office or even if you are in the same office and you are more than a few desks over, the way that you communicate is digital. Right? You are on phone calls. You are on video chats. Maybe you’ll come together for some meetings. But if you’re all not collocated, that doesn’t work in most cases. So, companies increasingly are already distributed, and they already are communicating digitally. So, migrating from that to being comfortable with people being remote full time is actually from a tactical perspective not that different. And you are seeing more and more companies start to understand that even though they do have some vestiges of their culture and their management and their process that aren’t comfortable with it. More and more companies are starting to get comfortable with it and be okay with people having the flexibility that they want and need.

Matt: So, is Remote Year as a company in terms of you conceptualizing your sales and marketing strategy moving forward, is it more of a B2B strategy where you are targeting companies and encouraging them to send their employees to you? Or is it more of a bottom up B2C strategy where you are talking to the employees directly and trying to get them to convince their employer to let them go? Which direction do you see more trending as you move forward with your sales and marketing strategy?

Greg: Yeah, we continue to see most of the interest and excitement from employees who really want to do this. And they then are armed with the tools that we’ve built, and they team that we have to help them go and get that permission to do this. We haven’t really cracked the nut yet fully on how to get companies to really promote this as a perk to win the culture and talent war. We think that there are going to be – there are some right now, but I think as we look towards the future, this is going to become table stakes for companies to have as part of their people ops strategy. They are going to recruit with it saying this is an opportunity. They will retain with it by saying people once they’ve been around for X, Y, Z amount of time and they’ve achieved a certain level of performance reviews can have an opportunity like going on Remote Year or a Remote year specifically. And I think this is going to be an opportunity if they are retaining folks to really invest in making them the future leaders of their company because of all the professional growth that happens on our programs. But we have been working on that. We haven’t fully cracked the nut on how to really build that into companies who are at a strategic level who can be promoting this to their workforce. We do believe long term that is the vision. But as we think about the next steps in the near term, we are pretty focused on where we are seeing lots of interest and excitement which still continues to come from employees who want to do this. 

Matt: Awesome. Greg, are you ready for the lightning round?

Greg: Let’s do it. Awesome.

Matt: All right. What is one book that has influenced you over the years that you would most recommend to people?

Greg: Oh, man. I love reading. And I think reading on the road with a Kindle is one of the best things ever. We actually had a shared Kindle account for our team until we got to like 100 people, and they shut us off. One of my favorite books that – I think about anthropology. I think about humans a lot and how they work, and how they change. It is Sapiens, an incredible book. I definitely recommend reading that book, and you should check it out. 

Matt: Awesome. What is one travel hack that you use that you would recommend to people?

Greg: Travel is all about going into environments that are different and interesting. Whenever I travel, I like to figure out the things that for me are comfortable and nice. So, one thing that I do whenever I get to a new place, especially when it’s an Airbnb or a Remote Year apartment or somewhere that has a kitchen, I like to go and get a dozen eggs. Because one of the things that makes me feel comfortable in the morning – wake up, fry up a couple eggs and eat those. Get the day started on the right foot. It’s a great travel hack for me to find some level of continuity for wherever I go. The other thing that I love to do is I love to walk. I love to walk around cities. And I try to spend as much time as I can outside, moving, being active and seeing different places. I try to walk 10 miles a day. Sometimes a challenge, sometimes it works. But it’s a great way to see a city. It’s a great way to get active. And it’s a great way to get acclimated to a new environment.

Matt: Awesome. What is one stress reduction technique that you have?

Greg: I think it’s going back to the same thing. I love to spend a lot of time walking. Whenever I travel, I spend a lot of time walking in whatever – I’m based in Mexico City these days. I walk around Mexico City as much as I can as well. It gets you moving. It gets your heart rate going. I would highly recommend people spend more time walking than they do. I don’t know what the science is, but I’m sure more will come out about the benefits of spending a lot of time walking. 

Matt: Awesome. Last two questions, Greg. What are your top three travel destinations? Favorite places you’ve ever been of all time that you’d recommend?

Greg: Oh, man. Top three is so challenging. I think anywhere you go there is so much unique, rich local culture. And we are in this amazing time where you have accessibility to getting into that and experiencing it authentically and these unbelievable opportunities. I can’t say that there are any three that are more special than others. But I would say in terms of recently, I have been spending a lot of time in Mexico City, unbelievable food, unbelievable culture. I spent a lot of time in Lisbon. The Portuguese culture is amazing, and they have great seafood, great wine, great people. That’s another unbelievable place to check out. Another one that – I was a few weeks ago in Lima, Peru. If you haven’t had ceviche in Lima, you got to get there. You got to try it. The Peruvian culture is incredible. There are so many cool activities; hiking the Inca Trail, unbelievable place to be.

Matt: Awesome, man. Last question. What are your top three bucket list destinations that you’ve never been to that you most want to go?

Greg: Oh, man. Bucket list destinations. Well, you are in Russia right now. I have never been to Russia. I don’t know that it’s a bucket list destination, but somewhere that I’ve been interested to check out because of some of the culture differences. I’m hopeful that I have the opportunity to go there at some point. I haven’t yet. I looked into it at one point, and I think there was some visa stuff. So, Russia would be very, very cool that I haven’t been to. I spent a lot of time across Asia, but I haven’t been to some of the larger cities that I think sound really cool and would love to check out. And I’m not such a big adventure person, but I think going to Antarctica would be just unbelievable at some point in my life if I had the opportunity. 

Matt: I love it, man. All right, Greg. Thank you so much for being on the show. I want to let you know how people can get ahold of you if they want to follow you on social media, if they want to learn more about Remote Year. And I understand for the Maverick Show listeners that we’ve got a link for them where if they are interested in doing the program, they can actually get a $200.00 discount on the program if they go through that link. So, we are going to put that up in the show notes. But beyond that, if they want to learn more about Remote Year or follow you on social media, how do they connect with you?

Greg: That’s awesome. If you want to connect with me, you can just email me directly; greg@remoteyear.com. I love getting emails. I love meeting people. Feel free to reach out directly. If you want to follow me – I don’t post that much on Instagram, but I do like to tweet. I tweet mostly about the future of work, remote work, and travel. And I’m at GDCaplan. Look forward to connecting with you over email or on Twitter. 

Matt: Awesome, Greg. Thanks so much for being here my man. This was a blast. 

Greg: Thank you so much, Matt. 

Matt: Thanks, buddy. Good night everybody.

Male Speaker: Be sure to visit the show notes page at www.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 www.TheMaverickShow.com. 

Male Speaker: Would you like to get Maverick Investor Group’s whitepaper 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 www.TheMaverickShow.com/nomad. The report is totally free and available for you now at www.TheMaverickShow.com/nomad. 

Female Speaker: Do you want to learn how to travel the world for a year plus with carry-on luggage only and look good while you are doing it? Go to the www.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 are 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 www.TheMaverickShow.com/packing. 

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Duration: 80 minutes