Matt Bowles: My guest today is Sharon Rosenberg. She is the co-founder of Overlap, the number one digital nomad app that makes it easy for travelers to stay connected to their friends from all over the world. Overlap enables you to keep track of your travel community, get alerts when your travel plans intersect with friends, get recommendations from people that you trust, and make plans to visit your bucket list destinations together. Overlap also enables you to check off each country you’ve been to and watch your travel profile fill in with colors and pins. You can keep trip dates and past travel organized which not only helps you remember your journey, but may also be useful for tax, visa and legal purposes. Originally from Sacramento, California, Sharon has now been a full-time digital nomad with no permanent base for the last five years and has traveled to 56 countries.

Sharon, welcome to the show.

Sharon Rosenberg: Thanks for having me, Matt.

Matt Bowles: I am so excited to have you here. You and I have been hanging out on the amazing continent of Africa for four months together now. We are both on the Remote Year program and currently we are together doing this interview in the city of Dakar, Senegal.

Sharon Rosenberg: We are.

Matt Bowles: And we should further set the scene by noting that we have just opened a bottle of red wine. This is a Saint Emilion from Bordeaux and we are going to be drinking through this throughout the episode. And further, we really need to start by talking about the experience in Dakar that you and I just had together today because as we are recording this and speaking into these microphones, the city is electric.

Sharon Rosenberg: It is. Oh, it was so wonderful. We just watched the Morocco game and the World Cup.

Matt Bowles: We did. Morocco had never been to the quarterfinals of a World Cup before, so it was their first time getting to the quarterfinals and no African team had ever made it past that round to the semifinals of the World Cup. And today Morocco played Portugal in the quarterfinals. They are the final African team in the World Cup, and they beat Portugal in a stunning game. And Morocco is moving on to the semifinals. And so, the entire, entire continent of Africa is absolutely abuzz today, celebrating out in the streets. We happen to watch the game at an Arab restaurant with the Moroccan community that lives in Dakar, Senegal, which made it even that much more special.

Sharon Rosenberg: It was incredible. Yes. We’re at a Lebanese restaurant and everyone is there. You had to reserve a table because it’s a very sought after place to watch this game. And everyone’s wearing their jerseys. And the energy there was just electric when that first goal was scored. Everyone’s standing on the table, everybody’s cheering, they’re dancing, someone was playing a drum. It was just really incredible to be here on the continent for that.

Matt Bowles: And then we walked outside after the game and we were walking over to a coffee shop and the streets were just filled with people with cars, people standing on top of cars, out of the windows, Moroccan flags flying everywhere. It’s just become a giant street party for the rest of the day.

Sharon Rosenberg: Yeah. There’s a big park in the center of town and everybody was gathered there. There are hundreds of people. There are cars driving by, people are waving flags, everyone’s honking their horns. And it was just so cool to stand there and take that in.

Matt Bowles: Let’s talk a little bit about some of your highlights from the previous four months we’ve been here together. We were in Cape Town for about a month. We were in Arusha, Tanzania, for a month. We were in Nairobi, Kenya for a month. Now we’re in Senegal. What have been for you, some of the top highlights of this trip?

Sharon Rosenberg: Yeah, I think everywhere that we’ve been has been drastically different from each other. Unique experiences in every single one of those countries. One of the top things that stands out for me, we did a safari in Tanzania through the Serengeti, the Ngorongoro Crater and the Tarangire Park. And one night we did a camping trip. It was a glamping trip. They’re very nice tents, but we’re staying in these tents. And everybody else had gone out to dinner and I really wanted a shower. So, I was in the tent by myself. I took a shower and I hear this, like, outside the window, like, oh, God, what’s that? And I unzip our tent window, and I open it up and I shine my flashlight out there and there’s this huge hippo standing right outside of our tent, just chowing down on grass.

And I just stood there in shock because hippos can be quite dangerous and faster than you would think. It was just right there. And so, I watched him for a while. And then as his protocol at the camp, you need to radio a guide that’ll come out to your tent and escort you to the restaurant and back. And so, I radio a guide, and they come out, and I go out onto my balcony and I’m getting my shoes on, and they have a confrontation with this hippo. The hippo charges them. They’re waving their hands, trying to look all big, scare them off. The hippo’s snapping his jaws at them. And I’m like, I should go inside. I go back to my tent, and I zip up, and a few minutes later, they come to knock on the door. They’re like, we’re here for you. They’re just totally unfazed. I’m like hippo. They’re like, oh, yeah, we do that all the time.

Matt Bowles: Just another day in the life in that region. That is amazing. It has been really cool to be so close to the animals. I, too, did a safari, not the exact same one that you were on, but a similar one in a similar place and had similar experiences, and it really, really was super special and amazing. I know you first came to this continent, though, about a decade ago. So, you have a long history with this amazing continent. But let’s go back even a little bit further than that just to give some background on you. Can you share a little bit about where you grew up and as you were growing up, how did your initial interest in travel kind of start to develop when you think back and your interest in different cultures and all of that?

Sharon Rosenberg: Yeah, so I grew up in Sacramento, California, and I grew up in the same family home my whole life. So, all the pets are buried in the backyard. From a few months after I was born to when I left for college. I grew up in this home. And so, a lot of fond memories in Sacramento. But I was fortunate that my parents, when I was younger, took me traveling a little bit. I remember a trip to Puerto Rico when I was in fourth grade. It was a business trip of my father’s that they were allowed to bring family to. And so, yeah, I remember this trip really fondly of going somewhere that was so different. And there were these frogs called Koki frogs that make the sound of Koki, Koki. Trying different foods and seeing the beaches, seeing the jungle, and just what a cool experience that was. And then we did a Europe trip when I was younger, and I did a French language exchange program at the end of high school.

So, I think that those early experiences definitely ignited the travel bug for me a little bit. And then I had a few later experiences in my adult life. So, I chose to study abroad in Cape Town in South Africa when I was in college. And I wasn’t proficient enough in any second language to study abroad somewhere that wasn’t native English speaking. And so that limited my choices a bit. And I had a lot of other friends that were doing Europe. And because I had had the fortune of going to Europe before with my family, I wanted to do something really different, and South Africa was a choice. And I reflected on world history that I had learned in school and saw that there was a gap around Africa, that a lot of our world history was European history. I really didn’t know much about the continent or the country, so I thought that it would be a really wonderful opportunity to learn.

Matt Bowles: And so, you went to Cape Town? Well, before I went to Cape Town, my first time going there was in 2015. I lived there for a month, and I’ve been back multiple times. You and I were just there together this year. But when you went that very first time, under the pretext that you just described, what was that trip like for you at that age? What did you go there wanting to learn? What did you leave with? And what impact do you think that had on you?

Sharon Rosenberg: Yeah, I think that trip was very impactful for me. I was there for six months, and I think the amount of different cultures that coexist in Cape Town was something that I found really interesting and that really excited me. I remember going to an ATM for the first time and seeing how many different languages were listed as options for how I could withdraw money, but just realizing, yeah. How many different cultures were coexisting there. And when you say a Cape Town accent, it could mean so many different things because it’s such a colorful mix of people that live there, so many different foods, so many different influences. So, I really loved experiencing all of that.

Matt Bowles: And when you were thinking that the history of Africa, the history of South Africa, that isn’t really taught very much in American schools, and I can certainly attest to that, that I didn’t learn very much about it either. When you went there and you immersed for six months, what did you come away with in terms of either historical knowledge or cultural political awareness? What do you think were some of the big picture takeaways from that trip?

Sharon Rosenberg: Yeah, I went to South Africa not knowing what the apartheid was, and I’m embarrassed to say that but it just wasn’t covered in our curriculum, or if it was, it was glazed over. It really was not something that I knew about. And so, I felt incredibly ignorant when I got there. And it was discussed quite a bit. And I was like, raising my hand slowly, can somebody fill me in? What is the apartheid? And so, I learned a lot about it.

But as part of my curriculum, I needed to take a South African history class. And we learned about the Khoikhoi and the San, and we learned about the British colonists, the Dutch colonists, the Boer wars, the Great Trek, all of these different historical events that took place there that I had been completely ignorant to that wasn’t covered in our world history that we learned in the States. And then I also took a lot of other really fun cultural classes. I took a Xhosa class. I took an Afro Caribbean dance class. I took African film classes and African theater classes, and really just immersed myself in the culture there. I learned so much in my six months there.

Matt Bowles: And then after that experience, you go back to California and then what? Can you trace a little bit of your personal, professional career trajectory from there and what ultimately led you back to what would become your digital nomad life?

Sharon Rosenberg: Sure. So, I came back to California, and I was in a sorority, and I saw this opportunity. So, we have a recruitment event called Rush, and it’s a massive event where everybody interested in joining a Greek house, sort of interviews with these different houses, and the way that that process is managed, at least in Santa Barbara in 2013, was very manual on paper. And I saw an opportunity to create an app. And so, I went out on Fiverr, and I found some developers, and I was like, hey, I have this idea. And I outlined my business plan, and they’re like, that’s great. We can build it. Send us the designs. It’s like, okay, I need to find a graphic designer to help me design this. And I contacted a friend of a friend who’s studying graphic design, like, hey, could you help me design this app? She’s like, you know, that’s really not a graphic design job.

That’s a product design job or a UX UI design job, which turned me on for the first time to that even being a career path, because at the time, I’m studying film and media studies and theater with an emphasis in scenic design. So, my goal at this time is to be a set designer for film and tv. But on the side, I’m working on this app, and I’m teaching myself how to design an app. I’m learning how to use Adobe tools. I’m watching YouTube tutorials. I’m learning about this whole space. Meanwhile, I graduate, I move down to LA, and I’m doing everything I can to immerse myself in the entertainment industry. So, I am doing set dressing with a mentor that’s a set designer. I am working as a professional background actor three to four days a week.

So, I’m in Maroon 5 music videos. I’m in a Zac Efron movie. I’m on a few episodes of Glee dancing around in the background. And I’m doing everything I can to be on set. So, I’m babysitting directors and kids. I’m doing documentary research on weird things people do with their ashes when they die and moose clubs and order of the Elk and all of these offbeat things that I’m documentary researching. I had to infiltrate a chat room to uncover a black market for fertility drugs, doing all these weird, offbeat things to just try to get my in in the entertainment industry. And I have this mentor that I was fortunate enough. She was really straight with me. And after some months, she asked me how passionate I was about set design. It’s like, why? Like, well, it’s just a very difficult industry to make it into.

And there’s a strong likelihood that you’re going to need to be financially supported by your family, by a boyfriend, by someone, or be working side jobs for many, many years to really make it in this position. Are you passionate about this? Like, yeah. No, not really. And so, I decided it was time to leave la. I needed to pursue something else. And I had many friends from college that moved up to the Bay Area. There were a lot of opportunities for millennials in tech at that time. And so, I made the move up of there and got a position at Yelp doing cold call sales. So, I was calling 100 small businesses a day asking if they wanted to buy ad space for Yelp, and I knew that this wasn’t it either. This was not my passion.

I struggled every single day. I didn’t want to go to work. It felt like a jail sentence. It’s like, this cannot be what adulting is. I can’t do this forever. And so, I thought back to that project that I did as a student and product design. It’s like, you know what? Working in startups is really fun. I love this culture around Yelp and around San Francisco startups and the barista upstairs and the pool table, and everybody’s young and innovative, and this is exciting. Cold call sales, isn’t it? For me, I want to transition into design. So, I did boot camp and I moved into design.

Matt Bowles: And then how did you eventually discover this whole concept of the digital nomad lifestyle?

Sharon Rosenberg: So, through this Bootcamp, they really encouraged us to go to these networking events. And we’re in the city, we’re in the right place for it. We’re going to all of these network events, rubbing elbows, shaking hands. And as it turned out, the way that I actually got my first job out of Bootcamp, and I was the first in my cohort to get a product design job, which was really exciting and, I think encouraging for the other people in my cohort. I was at my favorite bar in San Francisco. It’s called Butter. It’s a trailer park themed bar in Soma. And I was there just dancing and somebody approached me and just cold was like, hey, do you like travel? Like, yeah, I like traveling. Do you like design? What do you do? Yeah, I’m a designer. Like, great. I work for the startup. We’re hiring a designer in the travel space. You want to interview? Sure, I do. And that was how I got my first design gig.

And through that, they had me doing market research for high income millennials in the travel space, which this is 2015. There’s not a lot of high-income millennials at this time. But the area I was researching was quite narrow. And as part of that research project, I uncovered digital nomadism as a concept. And I had never heard of anything like this before. And as I was reading more about it, it said that the best roles for people that want to do this are developers and designers. And as it just so happened, I just trained to become a product designer. I am perfectly positioned to go do this thing. And so, I metaphorically threw a dart at a calendar and said, in a year’s time, that’s what I want to be doing. I want to be a digital nomad.

Matt Bowles: And your digital nomad life has been really incredible. You’ve done a lot of amazing things. You’ve been very intentional about doing a lot of amazing things and connecting with and immersing yourself in cultures in really particularly substantive ways. I think I want to ask you about the first time you went to an Indian wedding in India. And just for the context of how that entire experience came about and then the impact that that ultimately had on you.

Sharon Rosenberg: Sure. So, I had met someone out one night in San Francisco, and we had gone on a couple of dates, and he took me skydiving, which felt like a crazy thing to do on a third date. I was Showing it to my friends. I was like, should I do this? Do you want to do it? Yeah, I really want to do it. Okay, let’s go. So, I went skydiving with him and that was an incredible experience. And as we’re driving home after that event, he tells me that one of his best friends is about to get married in India. He’s about to go, would I want to go with him? I was like, would it be crazy if I said yes? But I really wanted to. It was somewhere that had always been on my bucket list.

And going with someone from the country is always the way to see a country and the way to immerse in the culture. And it just felt right. And so, I said yes, but can my roommate come? I brought my roommate as a buffer because we weren’t really dating yet and I wasn’t sure if I wanted to. And like, can I bring my best friend? He’s like, yeah, sure, let’s go to India. And so, we did. And to be honest, getting off the plane was the first time I had ever felt culture shock. I got out and Mumbai can really assault the senses. Not necessarily in a negative way, but there’s just a lot. You come out and your eyes sting and it smells like smoke and there’s chaos. It’s busy and it’s full of traffic and there’s constant honking. And I came out of the airport and just looked at a different world. I was like, what is this? This is so cool.

And so, yeah, we stayed at my boyfriend at the time’s family’s home. They took us out to go buy some formal saris to wear at the wedding, took us around Mumbai, did a tour of the slums, which I had just read the book Shantaram I wanted to read in advance of getting to India. And so, I felt like that provided some really interesting context for being there and walking around and experiencing all the sights and smells. So, then we go to the wedding. And for anyone who’s ever been to an Indian wedding, you know that it’s a multi-day event. This one was four days of different events. And it was elaborate. The groom comes in on a horse, there’s a parade, there’s a brass band, we’re waving rupees. We just had the most incredible time.

But I think some of the funny stories that came from that were the culture that we took in, but also some of the faux pas that we realized after we did them. So, for example, there’s a Mehendi ceremony that is a traditional part of An Indian wedding, which is getting your hands henna’s and having the patterns done, and they separate off the women to do that. And so, we’re over there getting our hands all done up, and they’re doing these really elaborate designs. And we’re trying to drink our lemonades without touching them with our hands, which is really difficult. We couldn’t get our hands wet for two or three hours while it sets. And my friend comes to the door, and I see him and I’m so excited. And I run up to him and I jump, and I hug him, and he spins me around. And everyone just stares at us with their jaws on the floor because men aren’t supposed to be at that ceremony. And certainly not touching people. No displays of affection. So, he knew better, too. But that was the first, like, oops moment.

And there was another moment in one of the later parties. The wedding was in Nagpur, and it might be something specific to Nagpur, but there are kind of a traveling tribe of eunuchs that come. And when I say eunuch, I don’t mean that they were castrated. They’re people that are Middlesex, and they’re sort of outcasted from Indian society. And so, they’ve found their place in this tradition where they come to births and weddings, and they come, and they dance in the front yard. And the family allows them to do that for a little bit, and then they pay them some money and they go on their way. But you’re not supposed to dance with them. We didn’t know. And we had been learning how to dance through this entire event.

People are pulling us in and teaching us, you know, different dance moves. And when that happened, we ran out and danced with them just like we had been learning from everyone again, jaws on the floor. And our friend, like, pulled us away. They’re like, don’t do that. Don’t do that. We’re like, oh, sorry. So many different, like learning experiences at this event about the way that different cultures operate. There was another tradition where the bride’s family, after the wedding ceremony, comes around and feeds you. And the bride’s family hand, like, spoon, feeds everybody at the wedding. And you just sit there, and you open your mouth, and you eat.

And it would be very rude to not take what was offered. So regardless of how full you are, regardless of if things don’t agree with you, you must sit there and eat. That was another. Another interesting part of the wedding. But we just had so much fun. And I really feel like a foreign wedding is the best way to be Immersed in a culture, everybody, all the aunties and uncles took it upon themselves to come up to us and talk to us and point out different foods we should, try and teach us different dance moves and explain what different people are wearing and different roles and what’s going on in each part of the ceremony. And I just felt really adopted by everybody at this wedding. It was so wonderful.

Matt Bowles: Well, I know you have been pretty intentional about having those types of experiences. And you’ve also been to local weddings in places like Morocco and Singapore and Taiwan and Mexico. Can you share a little bit about any highlights from some of those other spots and why that is such an important thing for you on your travels?

Sharon Rosenberg: Of course. So, at this Indian wedding, I met a couple of people that would then go on to have other weddings and invite me. I met Lynn and Tom, who are Vietnamese, and they were going to get married in two months from that Indian wedding. And so, I came back to San Francisco, and I came back to my office job, and I felt really stuck. I feel like I lived so much life in the few days, the month that I was in India. I was living so much life in each of those days. Then this drudgery in the office, sitting down and clocking for my eight hours. And all I could think about was being back out in the world. And so, when I had this opportunity to go to Vietnam two months later and go to this wedding, I did everything I could to be there.

Another thing that was going on was this travel company that I was working at had unlimited PTO, which was wonderful. But for many people that have been in that experience, oftentimes you don’t get to take as much PTO if you’re in one of those setups. But I had started to realize that we were running out of Runway and the company wouldn’t be around for so much longer. So, I really wanted to take advantage of that. And I presented it to my boss, like, hey, my best friends are getting married in Vietnam and I have to go. You have got to go to it. He’s like, okay, come back soon, I guess. And so, I booked a three-week trip and I left.

Matt Bowles: That’s so amazing. And how was the Vietnam experience?

Sharon Rosenberg: Absolutely incredible. So, this wedding was a three partner, and Lynn and Tom were kind enough to actually put me in the wedding. I was a bridesmaid. And they did this because my friends that I was traveling with were groomsmen, and they wanted me to be included in all of the wedding parties and to be as involved as they were, which was so kind of them to do.

So, I get there, and I have a custom ao dai fit, which is the traditional Vietnamese outfit. They’re so beautiful. They’re made of silk. And we go to the first ceremony, which is a traditional ceremony at the family’s house. And there’s a procession. We’re all holding gifts in front of the front lawn. They have a traditional ceremony in the house. And then we go to the big wedding party that is at a hotel at the center of Ho Chi Minh City that they’ve rented out. Performer gets on stage that somebody told me was the Vietnamese Justin Bieber. He’s a teenage favorite. He’s a celebrity. Everybody knows him. He sings several numbers. Everybody’s really excited that he’s there.

There’s a sand painter that is like a projector, and he’s painting images in the sand of a girl that becomes a woman that grows up and gets married. It was very emotional. It was a single tier kind of moment. Just a beautiful wedding party. And then for the third event, they bussed their 50 closest friends down to Mine, which is a beach town in the south of Vietnam, to have a beachfront wedding with the western style wedding with the big white gown and a seafood buffet and absolutely beautiful. But again, just such an incredible way to be immersed in that culture and to try local foods and to see local traditions, to wear local costume. I just felt so honored to be a part of that.

Matt Bowles: What an incredible experience. And then I have to ask, what ended up happening with the company that you were working for?

Sharon Rosenberg: So, on our bus down to Moine, there’s music playing and everybody’s drinking beers and having a good time on this bus. And I’m at the back of the bus trying to plan my life because I had seen a text the night prior on my phone from a coworker asking, do you want me to grab the cactus off of your desk? I was like, what? She’s like, oh, you didn’t hear. The company’s folded. There’s no more Trivana. Oh, shoot. Okay. So, all of the sudden, I had no urgency to return back to San Francisco. Francisco. And since I had taken this big flight out here to Asia, I wanted to really take advantage of that and see more while I was over there. And so, I was trying haphazardly to plan the rest of my trip.

Matt Bowles: All right, so now you have no job, you are in Vietnam. You do not need to go back to the United States. So, what do you do?

Sharon Rosenberg: Well, I very haphazardly planned a trip around Asia, and my original flight path was to go through Kunming, China, on the way back to San Francisco. And I was going to do this with my boyfriend at the time. And we were going to get off the plane at 11:12 at night, come into a hostel in the city, hopefully find a night market. And so, I didn’t want to let him do this alone because that would be really shitty of me to let him go to Kunming by himself, do this night market thing all by himself and go back home without me.

So, I was like, you know, I’m not getting refunded for that flight. Regardless, I’m going to come with you. We’re going to have this really fun time one night in Kunming and then you’re going to go home. I’m going to go back to Vietnam. And so, as I’m haphazardly researching, I see that there is a 72-hour transfer visa to go through China. That’s so great. What else is there to do in Kunming? Oh, as it turns out, there’s a rock forest and some really cool natural parks and formations and things that I can go see while I’m in the area.

So, I plan a more or less three-day trip in Kunming and then I’m going to go back to Vietnam and resume my travels. So, we get there and it’s late at night and we’re going through immigration, and they asked to see our exit flight. And I show the officer my flight to Vietnam, and he asks for my Chinese visa, to which I’m like, no, no, no, 72-hour transfer visa. And I point, there’s a sign above me, I point at it, and he looks down at my flight path and says, this isn’t a transfer. You’re going back to where you came from. You need to have a visa, or you can’t enter the country. And so, I panic, and I pulled out my original flight to California, like, oh, I’m so sorry, that was silly me, wrong paper. Here take this. And I think that he’ll just stamp me, but he writes in the time that my flight’s supposed to take off, which is in about 24 hours.

And so, I panic a little bit. I’m like, either I stand here and explain what I’ve just done and risk either getting sent off to California or Vietnam right now, or I just show up in three days and play dumb American girl and this is going to be totally fine. This is going to blow over. I’m taking a picture of the 72-hour transfer visa sign this will be fine. And so, we leave the airport, and we get a cab, and the town is an hour away from the airport. So, we get all the way out there, we check into our hostel, we ask if there’s any night market nearby. She’s like, yeah, just around the corner. Head out there.

So, we go, and quaint a little night market and we get some noodles and we’re having some dinner. And from the distance we hear this bumping music. What’s that? And this is a Monday night in a very non touristic town and we’re down for an adventure. We’re out here. So, we follow the music, and we see this nondescript door with a bodyguard standing out front of it looking very cross. And we point at the door. We’re like eh, us in there. It’s like. And he opens the door and what we see inside there, confetti are coming down from the ceiling. There are hundreds of people. There’s a DJ on the stage with her cape blowing in the wind. There are towers of like stacked champagne glasses, people playing dice games at the bar.

Just so unexpected, like a steampunk themed bar. And we walked in there and it felt like the whole bar turned around and looked at us. This white girl, an Indian guy enter the bar, and it felt like this little like screech of the record, you know. And everybody stares at us and then keeps going about their business. And somebody like takes us and pulls us over to their table and we’re google translating vodka soda. They’re like, yeah, they’re feeding us drinks off of their table and we’re just having the best time and we’re making friends, and we’re google translating things, and they take us to a different bar, and they take us to a different bar, and we end up on this little piece together bar crawl.

And we’ve got all these new friends and we’re just going out on a Monday night in Kunming, and we go back to our hotel, and we sleep for a few hours. My boyfriend wakes up at 4 in the morning to go take his flight. And I wake up at an appropriate hour to go check into a dorm room and they ask for my passport to check me into the dorm room, which I didn’t anticipate. And I show it to them, and they flip over to the page that the visa is on, and they see that it expires before the next evening. And they’re like, we can’t check you in. It’s like, oh, I had no idea. It was going to expire. Oh, no, what do I do? And so, she tells me there’s an immigration office in town. You’re going to need to go there and see if they can extend your visa. Like, okay, great.

And so, I went out in Kunming. I’m all by myself and it looks totally different by day. It is a cold, gray day. The city’s very dismal looking and just gray and blocky and everybody’s heads down, going to work and shuffling. And I’m trying to figure out how to get anywhere. I can’t use Google Maps because of the Chinese firewall. I can’t use any app that’s familiar to me. I have a paper map. I’m trying to match the Chinese characters with the symbols that I see on street signs. I somehow managed to more or less get to the immigration office. A really nice old gentleman takes my hand and walks me directly there. I offer to pay him, and he just touches his hand to his heart. He’s like, no. He gives me a hug and walks away. And I am very thankful to that older gentleman that helped me find the immigration office.

And I get there and I’m sitting in line for a long time. They all break for lunch. I go to a museum. I come back; nobody speaks English. I find someone that does. They try to help me. They can’t help me. I need to go back to the hostel. The hostel gets on the phone with the US Embassy, who gets on the phone with immigration. And they’re all translating. And basically, what they’re saying is that I have purposefully tricked the Chinese government. I falsified the information that I showed the visa agent. I showed them a flight that I had no intention of taking.

And if I am not out by my allotted 24 hours, I face three weeks of jail time. I face a hefty fine, and I might be barred from reentry to China for the rest of my life, even as a layover. So, at the point that they’ve delivered this information to me, I have about two hours left to go and the airport’s an hour away. I’m 26. This is pre nomading. This is before a lot of my solo travel. And I just have a meltdown in the lobby of this hostel. And this nice Dutch couple sees me and they’re like, are you packed? No, go do that. We’re going to try to help you with the flight.

Matt Bowles: Thank you.

Sharon Rosenberg: And so, they’re on the VPN on the hostel computer. I’m throwing my shit in a bag. I tried to do laundry. So, everything’s wet. So, I’m just putting wet clothes in my suitcase. I come back down. They tried their best. They couldn’t find me on a flight. I use the VPN to get a Skype call through to my parents, who bless them for picking up at three in the morning. And the WI fi is breaking up. She can barely hear what I’m saying. Like, I jail flight. Help.

Matt Bowles: Love.

Sharon Rosenberg: I don’t know what she’s heard, but I hope that she’s heard something. I have to hang up. I have to get to the airport now. Like the clock is ticking. So, I throw all my stuff in a cab, we go out to the airport. I connect to the WI FI at the Kunming airport. And I see that my mom has bought me a ticket to Bangkok, Thailand. Wonderful. I get on the plane and there’s a medical emergency and they’re taking everybody off of the plane. I’m standing there holding the armrests like, I will not leave this plane. I will not get off of it. They’re like, ma’am, you’re past security. You’re an international. It’s fine. No, you will pry my lifeless body off of this plane. I’m sitting here.

So, they unloaded the rest of the plane, except for me, took care of the emergency and reloaded everybody back onto it. And that was how I did not go to jail. But the rest of my travel around Asia was amazing. I made it back to Vietnam. I ended up on this camping trip inside of a cave. It’s a one day hike out to a cave and you get into a cave and there’s an ocean and tents that they set up inside of the cave. I say an ocean, but it’s like a, like a beach. It was a very cool experience. Went from Phong Nha to Hanoi to Ha Long Bay. I went to Hong Kong and then I made my way back to San Francisco jobless and ready to start anew.

Matt Bowles: Yes. So, what did you do professionally, career wise? At this point, you’ve had enough travel experience to know that you wanted to do the nomad life. But you don’t have a job at this point. So, what was your next move?

Sharon Rosenberg: So, I’m looking for my next gig. I know that I want something remote, but it is 2018, it’s early 2018, and it’s hard to find remote work at this time. And so, I’m applying for things. And what comes through is a contract job with Pacific Gas and Electric in San Francisco. And this is the primary utility company for most of California. And so, I joined a team there that’s building internal tools, mostly for linemen to locate overhead and underground gas and electric facilities. It’s interesting work. It’s not my dream job, but I’m searching and searching even while I’m at this job, trying to find remote work, and it’s just not panning out. And it occurs to me part of our team is working remotely from Seattle. We’re already doing our meetings digitally.

Perhaps I could pitch my boss on me going remote. And around this time, I learned about this company called Remote Year. I think I saw an ad on Instagram. I wanted to learn more. I go to an info night out in Oakland, and they tell me that they’ll send me a pitch deck to explain what this program is to my employer and to show the benefits that it would be for me and for them if I joined this program. And I thought that it would be a lot easier of a pitch to tell my boss, hey, I’m going on this organized networking event where Internet and housing will be taken care of for me so that all I need to do is concentrate on getting my work done. And that was an easy sell. My boss was really supportive, and I was totally shocked that she had said yes. I couldn’t believe that I was going to go on this trip.

So, I’m checking out all of my equipment with it, I’m crossing my T’s and dotting my I’s and make sure that I am good to go on this trip, everything’s aligned, I’ve packed up all of my things. And I found out a couple of weeks before that my boss is quitting. And that was very surprising. And so, I wasn’t sure now if my plans have been foiled, if this is still going to happen. And she pulls me aside and says, you know, the one person I was worried about affecting by this career move was you. I want to make sure that you’re still good to go and that everybody knows our agreement. And so, we talk to all the higher ups, we talk to other departments. She makes sure that people are aware of our agreement. And then I leave for my trip.

Matt Bowles: And let’s talk about your first Remote Year trip. So, I did my first Remote Year trip. It was a 12-month program. That’s of course why the company is called Remote Year, because initially they only offered the 12-month programs I did. Mine started in late 2016, went all the way around the world with a community of extraordinary people, and we ended in late 2017. Was when our program ended, you started your program in 2018, but you did a four-month program instead of a 12-month program. Where did you go and how was your first Remote Year experience?

Sharon Rosenberg: Yeah, so I was one of the first four-month programs that they offered. And our program leader was Travis King. Shout out.

Matt Bowles: Shout out. Maverick Show listeners know Travis King because he has been on The Maverick Show. Amazing human being.

Sharon Rosenberg: And he wrote an incredible book. If you haven’t read it yet, go check it out. So, Travis was our program leader. We were a group of about 35 digital nomads that set off across Europe. So, we started in Split, Croatia, we went to Prague and Czech Republic. We went to Valencia, Spain and we finished in Sofia, Bulgaria. I had an amazing trip. I really enjoyed it. Every country was so different from each other and our group was fantastic. A lot of different people from different walks of life. I began the trip professionally. Things started to fall apart.

So, I was going above and beyond to prove that I could do this work remotely. I was working longer hours, later shifts. I was working considerably more than I was in the office and I was getting great feedback on that. I was having performance reviews with the various teams that I was designing for, and everybody was so impressed with how communicative I was and how much work was getting done. However, at this time, remote work just was not widely accepted. And because the person that had agreed to letting me go remote was no longer there to stand by their decision. Things started to crumble when there was a reorg within the company, and I got a message from a stand in supervisor that asked if they could get on a call.

And all of the sudden, within a 15-minute conversation, I didn’t have a job anymore. I didn’t have two weeks’ notice, I didn’t have severance, I didn’t have anything. And so, I emerged from my bedroom sort of shocked. And this is in Prague. I had two roommates at the time, I had Tiani and Ms. Carol. And I really needed both of them to get through this moment as they took drastically different approaches. So, Ms. Carol gave me a big hug and she was like, this is just the universe’s way of pointing you in a different direction and it’s all going to be okay. And you got this.

And Tiani looked at me and she goes, fuck that shit, let’s get drunk. Took me out to a Burlesque. And I really needed the yin and yang of their approaches to get me through that time.

Matt Bowles: That’s so amazing. The Remote Year communities are just so absolutely incredible. Incredible. I mean everybody that finished my program and went through the 12 months with me is family for life. To this day, I see them all around the world, continue to travel with them and everything else. So that’s so amazing to hear these stories. So, your program, though, went to what were the four cities that you went to, and where did the program end up?

Sharon Rosenberg: We went to Split, Croatia. We went to Prague and Czech Republic. We went to Valencia, Spain, and we finished in Sofia, Bulgaria.

Matt Bowles: All right, so let’s talk about Bulgaria. I have been to Bulgaria a couple times. I have spent well over a month in Bansko, Bulgaria. How was your experience in Bulgaria?

Sharon Rosenberg: I had such a wonderful time in Bulgaria, and it’s actually my favorite European country, which is a bold claim. And to back that up, I’ll say that it is the country that surprised me the most. Sofia was the one city on our itinerary that I didn’t know anything about. I was totally unfamiliar with it, and I didn’t do any research prior to getting there. I just wanted to arrive and be surprised. And what I really loved about Sophia was a number of things, but I’m a big fan of speakeasies. I think that speaking is super fun. I love hunting, the thrill of the hunt, the adventure of needing to know a password or where it is or what the door looks like and going through these steps and these stages to find this little wonderful hole in the wall.

And the best way that I can describe Sofia is as speakeasy as a city. It’s gritty on the outside, its funky post-Soviet graffiti, and it’s a textured city. But there’s so many wonderful hidden gems within it, and you just need to know the right alleyway to turn down or the weird door to knock on, and you’ll find such interesting, wonderful places there. And the other thing that I loved about it was it was one of the only places we went that I didn’t hear people speaking English or having American accents. When I walked down the main street, it felt really immersive, and it felt great to be the only American walking around and that people were excited to see us. Thank you so much for visiting our country. Come eat here, do this. Meet my grandson. People were so friendly and so excited that we were there, and that was the first time in Europe that me.

Matt Bowles: Had experienced that you and I have so many similar travel preferences and priorities. You and I actually went to an amazing Speakeasy together, in Cape Town earlier this year, which was absolutely incredible. One of my favorite speakeasies in Cape Town. We have also, though, reminisced about a lot of the types of places that we like to go to or the types of cities that we appreciate. And sometimes they’re not always appreciated the same by every traveler.

And so that was one of the things, I think, that you and I connected about. Let’s stay in Europe here. And let me ask you about your experience, experiences in Italy. I know you’ve spent a lot of time there and that you have a lot of appreciation for the country. Tell me some of your favorite places in Italy and then tell me also what you love about Napoli.

Sharon Rosenberg: Yeah. So, in line with having a lot of similar tastes in cities, I call it texture, some would call it grit. But I like a city that kind of has a funky interest in it, that’s not so pristine, or Disneyland Main Street. I want to know where the people live. I want something raw and real. And there’s certainly places in Italy that offer that. For one, Palermo. I was just in for a month with Wi-Fi Tribe in June. I had an incredible time in Palermo.

I thought the food was excellent, the wine was excellent, the people were awesome, the beaches were beautiful, the markets were so interesting. We had this little produce market that would be set up nearby our apartment that I would go to almost every day and go and get a coffee, go get an espresso, go get some pastries, some vegetables. And I loved having that as my morning tradition was like, for a Euro, they would juice, fresh orange juice for me, and there is just nothing better.

Matt Bowles: So amazing. And in terms of a city that is so historically and politically and culturally rich, I spent about a month there. I was actually based in Ortega, which is the old city in Syracuse, which is insane. But I went and spent some time in Palermo as well. And then I went out to the Aeolian Islands and then did the west coast and went to Archie and Sausage. I mean, just castles on cliffs and dramatic stuff like that. But the amazing grit and authenticity and just the cultural milieu and the historical richness of Palermo was just unbelievable. I remember going on a street food tour, and it was a tour that, through food, gave you the entire cultural, political and economic class history of Palermo.

I mean, what a truly spectacular city. But I feel like a lot of people overlook cities like that. This is one of the things that I appreciated about you so much when we started talking about travel. You and I can go out onto the Amalfi coast and stay in Positano and appreciate it for all that it is and then go to Napoli and love spending time in Napoli, for all that it is. And it’s not the same thing as Positano, but it’s not less than Positano. It’s different and it’s amazing.

Sharon Rosenberg: Sure, in Sicily there’s Taormina, there’s Cefalu, there’s these really beautiful historic towns that are just pristine and gorgeous, but I was happy to have visited those. And then to be living in Palermo, there’s just something a little bit more raw and a real feeling about it. And it was an incredibly diverse city too. As you mentioned, every civilization has moved through Palermo at some point. History is varied and you see it in the people. And I just thought that that was something very unique about it.

And then something that I really loved about Napoli was walking down the street and there are these narrow, winding streets and they’re tight and these little smart cars are moving through them, and somebody hasn’t picked up the trash in three days because it’s run by the Mafia, but it’s fine. And it smells like pizza, and it smells like fish and grandma’s yelling out the window and there’s just so many wonderful things that are all happening at once. And I just thought that it was such an amazing, interesting rush of culture walking around there.

Matt Bowles: And if you actually take the time to go on the historical walking tours and to learn the history of that city and then you go and eat the food, arguably the best food in the entire country of Italy in Napoli, arguably the case. And if you’re willing to stand online, because it’s the only way you’re going to get into the top pizza places. But if you are willing to stand online and actually go into these pizza places, my mind was blown that a human being was somehow able to make a piece of food that tasted as good as it did when I was eating pizza and Napoli. And then you start learning the history. I remember I went to Sorbello.

Arguably, again, what is the single best pizza place in Naples? That’s a little bit contested, but certainly this was consensus top three for sure. And there’s always a three-hour line to get in. There are no reservations. And so, the only way you could wait in line for less than three hours was if you got there for the first seating. So, it opens at 5 and if you’re willing to get there at 3:30, you can stand in line for 90 minutes instead of 3 hours. I was like, done, I’ll do it. So, you get in, but then you start learning the history about how this dude like had to fight off the Italian mafia to keep his pizza place open. And this whole, like, unbelievable. I mean, it’s just like the history and the politics and the culture is so rich. And then you’re just learning about it while you’re eating food. That is literally blowing my mind as I’m eating it.

Sharon Rosenberg: I think food tours are a wonderful travel hack in that food tours inevitably are a historical tour because there’s so much history in the food and what people are eating. And they generally will share with your history around you, but you’re being bribed by food, food at every stop. So, like, a long walking tour can be draining. But on a food tour, you learn the same amount and you get fed the whole way.

Matt Bowles: And you often learn. If it’s a good food tour, you learn really nuanced and important things about the political and economic history of the place that you’re in. For example, I went on a street food tour of Palermo, and one of the things that you do is you go on this tour and when you eat something, they’re explaining to you where did this come from? Now, sometimes it’s a cultural influence. Oh, this was influenced by the Greeks. This was influenced by the Arabs. You know, this was. And a lot of people don’t know this stuff until they go there, right? Like, I can remember, I’m in Sicily and somebody’s like, oh, this is where Archimedes was born. Archimedes, right, the famous Greek dude that invented the lever. This is where Archimedes was born.

And somebody on our tour is like, oh, when did he move to Greece? No, he was born here. He lived his whole life, and he died here. This was part of Greece when Archimedes was alive, right? And we were like, oh, I didn’t know that. Or like, oh, the language that was spoken in Sicily was Arabic for over 100 years. Sicilian Arabic, right? And then like, oh. And so, then you’re eating the food and they’re explaining, oh, this comes from the Greek tradition, this comes from the Arabic tradition. And they’re giving you history class too, right? Because, like, you go to a street food vendor like, oh, this is a spleen sandwich, or this is something that’s made from a part of the animal that wasn’t eaten in restaurants.

So, they would put it outside, and then they would prepare it this way and serve it to the poor people who couldn’t afford to go into the restaurant. And so you start to learn this whole history of politics and the class dynamics and the cultural influences and everything else. And you come away from a food tour and you have this understanding of the city that you couldn’t have gotten from reading like three books on it.

All right, we are going to pause here and call that the end of Part one. If you are interested in getting more information on a Remote Year program like the one that Sharon and I are on together right now, I will put a link in the next episode that will give you a $100 credit towards your first Remote Year program. And if you’ve listened to the last 10 or so Maverick Show episodes, you’ve met a number of other people that are also on the same Remote Year program that Sharon and I are currently on. So, Alondo Brewington, Tammer Abiyu, Jessea Lu, Dr. Aprile Andelle, I didn’t know any of these people before the Remote Year program. This year we all wound up on the same program. I met them all and you have heard a number of them on the podcast. So, these are the types of people that you will meet on a Remote Year program. And if you’re interested in learning more about that, you can do one-month programs, four-month programs, 12-month programs, whatever is the best fit for you if you want to travel the world with other remote professionals as a community. So, I’ll put that link in the show notes. It’ll give you $100 credit towards your first Remote Year program. And be sure to tune in to the next episode to hear the conclusion of my interview with Sharon Rosenberg. Good night, everybody.