INTRO: This is part two of my interview with Sharon Rosenberg. If you have not yet listened to part one, that is episode #216, I highly suggest you go back and do that first. It provides some really important context for this episode. Sharon and I have been traveling in Africa together for four months on the remote year program. If you’ interested in learning more about how you can travel the world with a community of remote professionals, I will put a link in the show notes, and you can check out what remote. Year has to offer. They have one-month programs, four-month programs, 12-month programs. And you can get a $100 credit off your first remote year program if you use the link in the show notes. Just go to themaverickshow.com and go to the show notes for this episode to find the link for your 100 remote year cred as well as links to everything else that we’re going to discuss in this episode. If you have already listened to part one, then please enjoy the conclusion of my interview with Sharon Rosenberg.

Matt Bowles: Let’s talk about another place that you and I both love, which is Valparaiso in Chile. You’ve spent, I think, more time in Chile than I have. I was based in Santiago for a month, and I loved everything that I saw about Chile. I mean, I was very enamored by it. I got into Carménère wine when I was in Chile, and I started going to the Pablo Neruda houses. There’s one of them in Santiago; there’s one of them in Valparaiso. There’s a third one I haven’t yet been to; that’s further down the coast. There’s three of them. They’re all open for tourists.

And for folks that don’t know Pablo Neruda, one of the most famous poets of the century, I would say extraordinary poet but also a very high profile left wing political activist who was subsequently expelled and by the way, expelled and went out to this small fishing island in Italy and like just hung out. There’s an amazing movie about it. By the way, if folks haven’t seen the film Il Postino. It’s an Italian language film. If you’ve never seen it, ‘must see’. Must see for two reasons; one, because you love Chile and two, because you love Sicily.

Sharon Rosenberg: Okay.

Matt Bowles: Must see actually went to the island in Sicily where it was shot.

Sharon Rosenberg: Yeah.

Matt Bowles: The filming location. Yeah. Wow. It’s this incredible film and it’s about the actual historical event where Neruda is exiled from Chile, and he goes and lives on this small fishing island in Italy. The film is then a fictionalized version of what may or may not have happened there. But the basis of the film is that Neruda is of course this extraordinary love poet who has all of these adoring fans. And he’s now living on this remote fishing island and there is all this mail that is coming in for him from primarily female admirers of his love poetry. Neruda is married and he’s living with his wife on the island. But he’s getting these bags of mail from these adoring fans.

And there’s this Postman who’s about 18 years old or so. And every day he carries his giant bag of mail out to Neruda and delivers his mail. And the postman comes to understand that this man writes love poetry. And he is getting thousands of letters a day from women that adore his love poetry. And the 18-year-old postman is local guy there in the town. And he has a crush on this local woman. But he doesn’t know how to talk to her, right. He’s too shy. He doesn’t know what to say. And so, he ends up striking up this relationship with Pablo Neruda and basically saying, could you teach me how to write love poetry?

Sharon Rosenberg: Oh, so sweet.

Matt Bowles: So that I can speak to this woman that I have a crush on. Right? And then it’s about the development of this relationship. And Pablo Neruda is teaching him about metaphors and poetry and all this kind of stuff. And it is one of my all-time favorite films. It’s amazing. It’s called Il Postino. It’s in Italian with English subtitles. Absolutely amazing film. Anybody should see it before you go to Chile as context on Neruda and then go to the pub and Neruda houses in Santiago and in Valparaiso, you can go to both of them. They’re amazing audio tours, incredible experiences.

But overall, let’s talk about Valparaiso for people that haven’t been there. I tell people, I mean, there’s a number of reasons why I love it. To your point and similar to Napoli, a gritty port city. But the street art in Valparaiso, I tell people, for me it’s like an open-air art museum. The caliber of the street art that is there. I just walk through the streets and my mind is just absolutely blown.

Sharon Rosenberg: It’s beautiful. And a lot about the climate and the way that it’s built reminded me of San Francisco, that it’s a port city, it’s on the water, it’s got this microclimate that’s different than the rest of Chile. And so, the cold fog comes in and it’s usually cloudy and gray and then it burns off midday and then it comes back in in the evening. So, a lot of it felt close to home, which I think really endeared me to it. But beyond that, it’s bright, it’s colorful, it’s beautiful. There are all these funky buildings stacked on top of each other on this hill. And like you mentioned, street art is just beautiful and really tells the story of the people that live there, which drew me to it.

So, I had first been to Valpo when I was on my second Remote Year program. We were on a four-month program going through Latin America and our first stop was in Santiago, Chile. And as a weekend trip a bunch of us in our group headed out to Valpo and I just fell in love with it. I thought that it was beautiful. I loved the food, I loved the people I talked to, I loved everything about it. And I knew that I wanted to come back in some capacity. And so, the following month we had gone to Medellin and had a crossover event with this other organization called Wi-Fi Tribe.

So similar to Remote Year, they lead digital nomads on one-month excursions to different cities around the world. And I had the opportunity to meet one of their founders there who asked about my opinion of Chile and I shared how much I enjoyed it, but how much I especially enjoyed going to Valpo, which I think influenced him to create a trip there in the end of 2019.

Matt Bowles: First of all, shout out to Diego because he’s been on The Maverick Show. So, Maverick Show listeners know Diego, the co-founder of Wi-Fi Tribe. So you went back to Chile, you’ve now been there multiple times. You have been to more places in Chile than I have. You were just recently giving me tips I want to ask you for some tips for the audience because I have not been to a lot of Chile. It is a very long country that goes all the way down the west coast of the bottom part of South America, has a lot of amazing and very different climates, regions, legendary wine countries, legendary national parks and landscapes. To see these incredible, like, we’re talking about gritty port cities with street art. I mean, it really has everything depending on what you’re looking for. It’s very high on my list to go back. I may even go back later this year. Tell me a little bit about outside of Santiago, the capital, and outside of Valparaiso. What were some of the other highlights for you from Chile?

Sharon Rosenberg: Yeah, I think that it is an incredibly diverse country and there’s so much to see in it. One of my favorite parts of Chile was San Pedro de Atacama, or the Atacama Desert, which is up in the north. And they’ve actually used it as a movie set for Mars because it is a red, red desert and natural landscape there is just incredible. So, there’s a national park called Valle de la Luna, Valley of the Moon and aptly named. It looks like you’re walking on the moon. All of the sand and the rock structures and it’s just so beautiful. And there’s this town in San Pedro de Atacama that almost looks like a little gold rush town. There’s this main street that’s dusty and it’s got hotels and saloons and inns and bars and backpackers walking around from this adventure to that. And it’s just such a cool place.

But the highlight of that area and Chile in general, they sell the most telescopes of anywhere else in the world because it’s one of the best places worldwide for stargazing, especially in Atacama because there’s very little light pollution. Unfortunately, when we were there, it was a full moon, so I went out on a stargazing trip. And we’re there, and they have a really powerful telescope and they’re pointing at the sky and we’re looking at everything and we’re just not seeing a lot. And I’m trying to not show that I’m disappointed. My friend who’s from Chile is audibly disappointed. He’s like, oh, it’s usually better. I’m so sick. Sorry. It’s okay. Like, this is. When we’re here, it’s fine. We can see a lot. It’s cool. But I’m a little disappointed.

And we go to sleep, and we need to wake up early in the morning to go to these geysers, because the geysers are Most active at 5 in the morning when it’s cold outside and it’s a three-hour drive away. And so, we woke up at 2ish in the morning to get out there. And by this point in time, the moon has moved to the other side of the planet. And so, as we’re waiting for the car, I look up and I just see the entire arm of the Milky Way, just more stars than I’ve ever seen in my life. And it’s incredible. And we get picked up in the car and we drive out on the way to the geysers. And now we’re out of the city in 10, 15 minutes. And I ask the driver, like, pull over, pull over. And Kat, who also works for Wi-Fi Tribe, was driving us.

And the four of us that are in the car pulled over. And we all just stood outside of the car, silent, looking at the sky. And we can see the whole galaxy. And there’s shooting stars every 30 seconds. They’re everywhere. And I’ve never seen anything like that. We all just stood there in a little haggle looking at the stars, and it was just absolutely breathtaking.

Matt Bowles: It’s so amazing. Well, one of the other places that I know has a really special place in your heart that I want to ask you about is Mexico. I have been to Mexico multiple times, but I have never been to the Day of the Dead. And I want to ask you about, in general, just some of your experiences in Mexico, why it’s so meaningful to you, what you love about it, and then also what your experience was like at the Day of the Dead and what that is for people that have never heard of it. Just explain what it is and why it’s meaningful to you.

Sharon Rosenberg: Sure. I don’t know that I can really put my finger on what it is about Mexico that draws me back there, but I’ve been many times, and I’ve traveled the country extensively. In 2020, I did a road trip from Mexico City to Guadalajara, stopping in every little town along the way, and just found it magical. But yeah, I think that Mexico is so diverse. It’s a lot more than beach towns. The beaches are beautiful too, don’t get me wrong. But there’s so much to experience in Mexico and so much difference from one town to another in culture and food, in language.

And there’s something about Dia de Muertos that I think is a really beautiful holiday and a really beautiful celebration. And unintentionally, I found myself in Mexico for three of them in a row. And my first diagnosis was in Mexico City. And while it was a really fun celebration, we didn’t have a particularly authentic experience, as the parade that goes through Mexico City actually was inspired by the James Bond movie. They did a parade in that movie, and they thought that it would attract tourists or. I’m not really sure how it came about, but the parade did come about after that movie. So, lots of fun. Not super authentic.

The following year, in 2020, I went to Oaxaca. And I have a lot of love for Oaxaca as a city. It is quaint and colorful, and the food is incredible. And I really grew a love for mezcal when I was there. And we had such a unique experience being there in 2020, because after the Pixar movie Coco came out, a lot of tourism started flocking to Oaxaca, specifically around Dia de Muertos. And as locals put it, it had grown to be a large tourist attraction, and it had lost a level of authenticity. But because we were there during the pandemic, we were one of nine tourists there. We met every other tourist, said hello to them. There were very few of us, and, you know, the graveyards were shut. They didn’t have a parade. They didn’t have a lot of these big attractions that people went for. But what we did experience was a lot more authentic. We saw families do sand paintings out front of their homes and decorating their storefronts with marigolds. We saw people celebrating with their families. We had a lot more personal feelings of an experience.

And I had been told that actually the most authentic celebration of Dia de Muertos was in Patzcuaro in Michoacan, which is a four-to-five-hour road trip outside of Mexico City. So, I knew that that was where I wanted to be in 2021. And I was in Mexico City for another foreign wedding. It was another awesome experience. But after that, we rented a car and we went out to Pat’s Cuaro, and we got this great Airbnb, lots of festivities happening in town. And we went out to the market, we bought our panda Muertos and our flowers, and we made an offerenda. And we tried to celebrate in the most traditional way, but we didn’t really know where to go or what to do. And we got a message from our Airbnb owner, and he was like, hey, what are you guys doing for the actual day of Dia de Muertos? I don’t really know. We’ll be in town; we’ll figure it out. It’s like, come with me if you want, but come with me. It’s going to be good, okay?

And so, he comes that night and he pick us up and he drives us out of town to these really small, little neighboring towns. And we get to one of them and he parks the car, and we walk for a half hour in. I’m thinking, you know, we would never have found this on our own. He takes us in, and there’s a graveyard and a church, and the graveyard is covered from edge to edge and marigolds. And there’s all of these families sitting at each of the graves. And there’s people. There are mariachis playing music and people drinking Mezcal and pouring one out. There’s Coca Cola bottles and packs of cigarettes and all of these things on top of the graves that their loved ones would have liked. And the sight was just indescribable. It was so beautiful.

And we went up to the top of the church and the bell is ringing, and family saw us there and recognized that we’re not from there and offered to take us over to their gravestones, telling us about their traditions, about who they’re there for, and just really allowed us to observe and to be a part of. It was so emotional. It was so special to be there. And we felt so honored that we were welcomed, that we weren’t intruding in this family event, but that people wanted us there, that they wanted to bring us into this moment and show us this. And it was maybe one of my most special travel moments.

Matt Bowles: It was so amazing. Well, one of the other things that you and I have definitely connected on and bonded over and shared many nights together doing is wine tasting. You are from California, of course, but can you share a little bit about your development of your wine appreciation, where that sort of came from initially? And then you and I both, of course, travel around and intentionally go to amazing wine regions in places like Italy or South Africa or South America, and see beautiful things and drink amazing wines. And we have that in common. But where did that sort of come from? What was that trajectory like for you, and what have been some of your most memorable wine tasting experiences?

Sharon Rosenberg: So, yeah, growing up, my parents have always been wine enthusiasts and have been involved in the Napa scene. But we’re generally strict with me drinking before the age of 21. So, it wasn’t something that I had really been exposed to at home. And I went to UC Santa Barbara, which is known for being a bit of a party school. And so, we drank quite a bit there, but we were not drinking nice wines. We were drinking bagged wine. We were drinking Franzia, playing slapping the bag and doing whatever it is college kids do. And I remember coming home one holiday and being like, mom, dad, I like wine. Like, that’s so great, honey, what are you drinking? Franzia is the best. Oh, no, that won’t do. We’re going to need to educate you.

And so, I studied abroad in South Africa, as I had mentioned, and they have an incredible wine scene there. And they have a wine region called Stellenbosch that we went out as a study abroad group and did a wine taste tasting. And that was my first wine tasting. And we were drinking incredible wines. They were a lot better than Francia. Set my standards to a new level. And one thing that I remember taking away from that too, was that the wine wasn’t expensive. And I asked why we were drinking such a nice bottle that was going for 10, $15. And they told me that wine is meant to be shared. And we don’t price this high because we don’t want this to be so precious. Like, we want you to have a nice bottle of wine to share with your family to open on any occasion. We don’t want to price this out of your range. That would make you only take this out on special occasions.

Like, that’s such a wonderful mentality. I love that. Let’s buy five. And so that was really my exposure to wine was the study abroad trip. And I came back to California. I was of age, and my parents started taking me out to some very nice places in Napa to do some tastings, which elevated my taste. When I got back to Santa Barbara for my senior year of college, I took a wine tasting class, which for some reason counted for college credit.

Matt Bowles: Wow. Go to school in California, folks.

Sharon Rosenberg: I took a sailing class, I took an interpretive dance class, and I took a wine tasting class. And all of those counted for college credit. I really did learn a lot in this wine tasting class. And the teacher noticed my enthusiasm and was like, I have a wine shop in downtown Santa Barbara. I have a tasting room, and I’m looking for people to pour wine there. Would you be interested? It sounds like a great college job. And so, he took me on as an employee, and I was a wine pour on State Street in Santa Barbara. And so, we have what’s known as the urban Wine trail, which is a series of tasting rooms all in a row on State Street where people can go and do tastings.

And what was really special about having that job was that when you’re in the industry in California, if you can show a pay stub, if you can show that you work in the industry, you and a guest get to taste for free. Anyway, as a college student, I really couldn’t afford to be tasting nice wines all the time. But as a perk of this job, I was tasting very, very nice wines and getting an education in California wine while doing it. So that really opened me up to wine as a hobby and it was an excellent college job. So, from that point on, it became an interest of mine. I wouldn’t say that I’m an expert in world wine, but it’s something that I really enjoy as I travel, learning about different wine regions, trying different wines, going tasting. Yeah, learning about the varietals in every country that I go to.

I think one that really stood out to me was Georgia. We talked about this a bit. Georgia claims to be the origin of wine, that this is where wine was invented. And they have some different techniques to make wine that are. It’s quite different than any other wine that you might taste anywhere else. One being for their white wine, putting it in these terracotta pots and burying it, which gives it this very earthy flavor and this different hue and color to it. It’s very different. But yeah, just interesting experiences tasting all sorts of varieties of wine from all over the world.

Matt Bowles: I totally agree. I think it is an incredible part of travel and when you go to a wine producing country, to be able to go and see the beauty of these wine vineyards in these regions and then to just drink this insane wine and learn about this stuff is incredible. And you and I, of course, have had a lot of conversations about that. You’ve been to some of the top ones in the world, Chianti in Italy and other places like that. You were telling me, though, about your experience in Chile during the uprising in 2019. You were in the country for that. What was your experience like during that time?

Sharon Rosenberg: So, as you mentioned, Chile is well known for Carménère and for their wine region in general. And so, we were with Wi-Fi Tribe in Valparaiso. And we were there during 2019, at the end of 2019, which was a time of political uprising. So, we were really unsure when we arrived in Chile. Is this safe? Should we be here? Is this, okay? And my first week, I had come before the program had started and I was in Santiago, and I was visiting a friend there and he was about to move. We were going to a going away party and there were protests in the street. We drove over a fire blockade.

There was a really scary moment where I went to go co-work in a Starbucks near the center of town. And he worked in one of the government buildings. And so, I was staying nearby at a Starbucks. And he sent me a text. Hey, are you indoors? The protests are getting out of hand. They had boarded up the windows and had locked the doors and kept us in there for an hour or two while the protest passed. It was just a really difficult time to be traveling in the country. We were having this wine tasting event as part of the group that we were there. And underneath the building that we were staying in was this event space. And so, a woman had come, and she had brought several bottles for us to try. And we were sitting there sipping wine, and we started to see people running about outside, people pulling on ski masks, like, maybe we should close these garage doors.

And so, they bring down the metal doors and close those, and we start sipping our wines. And she’s describing the flavor notes and we’re swooshing and tasting and we’re hearing hoses outside on the metal doors and people banging on them. And the tear gas starts to leak up under the garage doors and all of our eyes start watering and we’re tearing up and we’re trying to drink the wine like, tastes like pepper. It’s a little smoky note. It’s just the contrast of what was happening outside and what was happening inside was notable.

But I don’t regret being there at that time. It was very interesting politically, what was happening in Chile at that time. And we had such a unique perspective on the news. It looked really scary on the news. It looked like a war was happening. And I was getting a lot of concerned calls from family and friends. Are you in Chile right now? Are you all right? And we were never in danger. We were always okay. But it was so interesting to speak to people both in Santiago and in Valparaiso, about their perspectives about what was going on, about what they were fighting for, about what side they stood on. I think we would have gotten that if we weren’t there in person.

Matt Bowles: Yeah, I think that’s an incredibly important piece of travel is to actually go to these places and actually talk to the people and actually be immersed in these situations and learn about them firsthand. Because it’s very, very different from a lot of the stuff that you’re going to see on the news and all that kind of stuff. So that’s amazing.

Well, you’ve been on multiple remote year programs now, this is your third. You have been on multiple Wi-Fi tribe chapters. You’ve also done some other type of community centric nomadic travel and patronized co living spaces companies like Outsite or hostel networks like Selena and things like that that sort of are alternative ways of bringing travelers together and creating community in different places around the world.

And I’m wondering with all of that diverse over many, many years, can you reflect on that a little bit? And maybe for folks that might even be at the beginning of their nomadic journey and they’re thinking about, I want to go travel the world, but I want to do it and I want to have some type of community connection, I want to have some type of community base, I want to be able to have friends and get hugs and all that kind of stuff. What are some of the differences from some of these types of services organizations? What are some of the advantages of doing some you’ve obviously done of them, and you continue to do all of them. So how should people start thinking about making those choices and how to travel and which company might be right for them to plug in?

Sharon Rosenberg: Yeah, I’ve done quite an extensive variety of nomad programs, and I’ve also traveled solo. And while I really do enjoy traveling solo, I think that anybody that’s interested in travel shouldn’t wait for their friends, shouldn’t wait for someone to give them permission, shouldn’t wait for someone they know to go with them. If you’re ready to go now, go now. And if that means you’re going alone, go alone. It’s not that scary. And you will meet people on the road, you will form the community. Without a doubt, the reason that I’ve done so many of these various nomad programs is because the community makes this sustainable. And as a backpacker, as a solo traveler, if you’re moving in and out of hostels, you’re meeting wonderful people, but they’re transient relationships. And every four or five days you’re going to need to meet new people and have the same surface level conversations. And it’s wonderful and it’s interesting and it’s great to meet so many people, but you’ll burn out. It’s hard to live like that for years and years.

So, something that these programs offer is a more sustainable community, people that you’re going to see again, people that you can get to know at a deeper level and that will travel with you for some time. So, I began my journey with Remote Year, and Remote Year offers longer form programs. So, all the programs I’ve done with Remote Year have been four months. You can also do a full year long program. They’re starting to offer shorter programs. But I think that four months is a really nice, sweet spot to get to know the people that you’re traveling with and to experience a region. Remote Year caters a lot for you. So, it comes with a local team of people that are from that country that help to integrate you with that local culture, with that language, with events happening in the area. It comes with a co-working space. It takes care of all the travel in between countries on your program.

Wi-Fi Tribe differs a little bit in that they are one-month programs at a time. There’s a program leader, but there’s not a city team. And then all of the events or activities that you might do are self-planned by the group. That takes a little bit more work. But it’s also a really wonderful group bonding experience to sit down on Tribal Tuesday, which is a Tuesday that is designated where everybody gets together. You might order pizza; you all get to one place, and you just talk about the upcoming weekend. What are we going to do, what are we going to plan, who’s going to do what. And because it’s all self-planned, sometimes things go wrong. Sometimes you end up on a weird adventure. And those are the best bonding moments is kind of figuring it out in the chaos with the group that you’re with. And so, I really value that.

Selena is a chain of hostiles that also has a co-working space as a part of it. Sometimes I compare Selena to Starbucks. Is it the best cup of coffee that you’re going to have? No. Is it the most local experience that you’re going to have? No. Is it consistent and the Internet’s going to work? Absolutely. And so, I think that that is a big value in that chain is that it is very catered towards digital nomads in that they have a co working space where the Internet will work and where that’s a priority. So that enables you without question to work in places like the jungle of Costa Rica, where the city’s power might go out, but the satellite Internet at the Salina will still work.

And so, it really opens doors for a variety of exotic locations. And then Outsite is also a co living space. Co living meaning that other travelers, digital nomads, longer term visitors, will book a stay here. Sometimes there’s a minimum stay of three weeks or a month. They guarantee a workspace; they guarantee working Wi-Fi. Sometimes there’s a community manager there to try to instigate activity. But really, it’s just providing community to do things with. And so, I’ve stayed at the outsight in San Jose del Cabo. I’ve stayed at the outside in Lisbon and Fuerteventura and Mexico City. And I found really wonderful community there.

Matt Bowles: Well, I got to ask you about one more co-living space that you have coming up in your future plans, which sounds completely insane, and I literally learned about it from you. It’s called the Swiss Escape. What is that all about, Sharon, what are you going to do later this year?

Sharon Rosenberg: I’m so excited. So, the Swiss Escape is a co living space up in the Swiss Alps and it is a co living space centered around skiing. Looks like a cabin, like a lodge, and I’m very excited for that one. And as a Californian, I haven’t spent a lot of time in cold, so I’m bracing myself to do two months on a ski trip through the snow in Bansko, Bulgaria, and then in the French and Swiss Alps. And I’m just hoping that my ski skills will come back to me, trusting that they will. And I think it’s going to be a great time.

Matt Bowles: That’s going to be absolutely unbelievable. You’re going, by the way, with Dani Dirks, who Maverick Show listeners know as well because she’s been on the show. So, the two of you are going to have an unbelievable time that is going to be absolutely amazing. All right. At this point, you’ve been traveling the world for five years. You’ve been plugging into all these different communities, multiple remote your groups, multiple Wi-Fi Tribe chapters, all these meeting people at all these different co living spaces. You have a massive network of nomads that you know. I want to ask you now about founding the Overlap platform, the Overlap app. Can you start off with what was the origin, the motivation, the impetus, the story that led to you deciding that you needed to find this app?

Sharon Rosenberg: Sure. So, I’ve been traveling for five years. I’ve met so many incredible people through all of the programs that I had just mentioned. And most of these programs have an internal platform for communication. But I really didn’t have a way to stay in touch with all of the people across all of these programs that I’ve met. And I found myself disappointed by the current existing tools, which are Instagram. I would see, oh, I’m in Spain, somebody else is in Spain. And I reached out. I’m like, are you here? I’m here. They’re like, ah, I’m posting these pictures later. I was there two weeks ago. I wish I knew. And it just kept hitting a wall with all of these missed connections.

And my community of nomads is always out in the world, always moving. And I wanted a way to keep track of that community and find opportunities to see those people again. And there just weren’t existing solutions that I thought were working for this problem. So that’s where the idea had come from, was how can I create a platform that will let me know when my plans will cross over with other people in the community and afford me opportunities to see these people again. So, I started designing out this app in December of 2020 and I reached out on the Remote Year Slack and asked about any developers that might be interested in founding a project with me. And Nicholas Savardounas reached out and said, hey, I’m a developer. I’m really interested in this project, I would love to know more.

So, I brought him on as my first co-founder and one of his very close friends, Jason Hu, who I have actually met both in Chiang Mai and in Buenos Aires. They were traveling together at the time, and I believe they were in Sofia, Bulgaria. Jason had just shattered his leg, so he had just come back from the hospital. He was going to be in bed for a period of time and also happened to be a developer and seemed to have a lot of free time on his hands. So, we were looking for someone to assist with the backend. Nick was like, hey, I got a great buddy. He’s here. What do you think about bringing Jason onto the team? Sounds like a great idea. And that’s how we became a team of co-founders.

And so, both Jason and Nick are Remote Year graduates and thoroughly understand the nomad experience. They’ve both been nomads themselves for years and have been instrumental in bringing this vision to life and contributing to the features that exist in the app today. And so, it would not be here without them. And I think we’re an amazing team and I’m excited to see where things go.

Matt Bowles: I love hearing about these Remote Year connections. You also know and have listened to the episode that I did with Majid Majalid, who founded an app as a side hustle while he was on a Remote Year program called Chipper Cash for Cross Border Money Transfer in Africa, which now five years later is valuated at $2 billion. So, this kind of stuff happens. People start stuff on Remote Year, they meet people on Remote Year, they found things on Remote Year and they blow up and do big things. And so, I love to hear that story. Let’s talk a little bit about what Overlap actually does.

So, I’m a Big fan of the app. I’m a user of it. I have just now opened it on my phone. You and I can both look at this, and I want to sort of describe this for folks and just kind of talk them through what this offers. So, I’ve opened up the Overlap app on my phone. I’ve already, of course, set up my profile. So here I can see that it shows where I am right now. It shows I’m in Dakar, Senegal. It shows how many countries I have visited, because I entered that into the app when I set up the profile. So, it says I’ve been to 77 countries. It shows me the percentage of the world that those 77 countries represent, which is only 30% of the world. I’m not even a third of the way there, Sharon.

In all of my travels. And then it shows me how many friends I have on the app. So, if I want to click over to my connections, I can see the list of all of the people, including you, that I am friends with on this app. So, it’s people like you, people like Dani Dirks and other nomad friends of mine are all friends of mine on this app. And so, the cool thing that I like about that is that it also now has a map feature. So, I click over to the map feature, and I can actually see if I am on the world map and I toggle it to current. I can see where those nomad friends of mine currently are in the world. So, I can see the image of my different friends. And I can see some of them are here in Africa with me of course. Some of them are in Asia. Some of them are in North America. Some of them are all over the place. And I can actually see where my friends are currently.

Then the other feature that I love is that the world map also has an upcoming feature. And I can actually pick a particular date range. So, if I want to say, where are my friends going to be in January? Let’s say from the week of January 7th to January 14th, maybe I have a free week. Where are my friends going to be? I can click that. And my friends, it shows me where they are going to be in the future on that particular week all over the world. So that is an amazing feature. That is really, really cool.

Sharon Rosenberg: Yeah. One of the features that we’re most excited about is that it will show you where you’re going to cross paths with friends. So, you add all of your upcoming travel plans and if you’re connected with anybody that’s going to be in the Same place at the same time, you’ll get a notification saying that you will be there, you’re crossing paths, please meet up. Likewise, you fill out a wish list. So, if, say, Matt is going to go to Iceland, he makes plans. And I have been dying to go to Iceland. I want to see the Northern lights. That’s a real example. It will tell me that Matt’s made plans. I want to go. I should reach out to him and see if I can hop on those. When you set up a new trip, it asks if you want recommendations for that place.

So, if I’m going somewhere brand new that I’ve never been before and I know maybe my connections have been, I’ll leave that box checked and my connections that have been there will receive a notification asking to provide me with any recs that they have for that city.

Matt Bowles: That is so awesome. Yeah. So, I’m just looking here, for example, so I’ve inputted my upcoming trips into Overlap. So, for example, I’m going to be in Accra, in Ghana for the New Year’s Eve week. You are going to be there as well, of course. We’re going to hit a couple amazing afrobeat festivals together. But what I can do is I can click into that trip, and it automatically populates and shows me which other friends of mine are going to be there. So, I can see that our friend Dani Dirks, of course, is also going to be there, right. And you can see who else is going to be in those places at the same time. Or you can just look and see where other people are going to be that week. So, I can just say where in the world are my friends going to be that week? And I can see some other people are going to be in other places in Africa. So, I would know, maybe I could hit them up and see if they want to come through.

Sharon Rosenberg: So that’s the current state of the app. There’s a lot of work in progress. We are currently building a feed to see in real time as all of your friends are planning new trips. Also, a forum so that you can ask your travel community about recommendations about ideas, places you want to go, and get people to join you on a group trip. Really just create a single source for you and your friends to share information about travel and upcoming trips. So, we’re really excited for what we have in store.

Matt Bowles: That’s super, super cool. And I love this wish list concept. Basically, like bucket list. What are some places that I want to do that I want to hit? And so, I can just type in, oh, I want to go to this country, that country, this country, that country. You can even add some text about what you want to do there. If you want to go on a scuba diving trip there, you want to go hiking there, you want to go see this really cool thing and then your friends can see that and then you can say, oh, this other person also wants to go to this country. And then you can start planning trips together and coordinating and stuff like that. So that’s also a really cool feature.

Sharon Rosenberg: And we’ve been building this with digital nomads in mind. So, we’ve been really excited about all of the feedback that our users have provided us. And if you give this app a try and you have new feature ideas or you see a bug or there’s something that you think could be working better, just type anything in the feedback form you can find in the menu. Upvote ideas that you like. Give us recommendations. We’re building this for this community, and we want your feedback. And we’ve been so thrilled with how much feedback we’ve already received and are building this for you guys. So please share what you think.

Matt Bowles: I love it. Well, you know, you got my feedback. I’ve already shared with you a couple pieces of feedback and you’ve already taken them into account and your team has, I think, already even fixed them or implemented them, which has been really cool to see. But yeah, it’s really amazing. There are thousands of people on this app right now. I was just looking at your app today. You have hundreds of friends on this thing and so it also has an in-app messaging feature. If you’re going to be somewhere, either someone else is and you want to coordinate with them or one of your friends was there earlier, you can ask them for recommendations about the place too, which is a really cool thing. So yeah, big fan of this and it’s incredible to see how quickly you guys are developing, you’re adding more features. Sort of the vision for this app over the next year, two-year time horizon. How are you envisioning this evolving?

Sharon Rosenberg: We want this to be the platform for travelers to meet other travelers in the area, to find second degree connections, and to create community to travel. So, we’re looking to build out features that are going to help our users find people they already know, meet people that are going to be on a similar path, meet people with shared interests, and even to book digital nomad programs or book further travel on our platform that aligns with their interest and with their wish list. So, we’re looking to build out lots of features that are going to be useful not only to the digital nomad community, but to backpackers, to van lifers, to people that travel for business, to all sorts of frequent travelers.

Matt Bowles: So, cool. Love this. All right, so, Sharon, how can people get this app and start using it?

Sharon Rosenberg: It’s available on the app store and the Google Play Store. If you search for Overlap –  nomads and travelers or even just Overlap, it should come up.

Matt Bowles: We’re also going to put a direct link in the show notes so you can just go to one place at themaverickshow.com and go to the show notes for this episode. There you’ll see the direct link to Overlap. Put the website up there and where you can go and download the app for totally free. So absolutely nothing to lose. You can connect with me immediately, download the Overlap app, look me up and reach out to me. Connect with me on Overlap would be super, super fun to do that. And then you’ll have your very first friend, which will be me, and then connect and see who else you might know that’s on there. But super, super cool platform and really excited with what you guys are doing with this.

Sharon, let me ask you one more question and then we’ll wrap this up and move into the lightning round. When you think back about all the travel that you have done over these years, people you’ve met, experiences that you’ve had, how has all of this impacted you as a person? Why are you continuing to do more traveling at this point in your life? What does travel mean to you?

Sharon Rosenberg: I think I get a lot from it. I learn and grow so much every day in a way that when I was living in one place, I felt stagnant. I felt like I was living a very repetitive lifestyle. And by traveling, every day is different. I am in a new environment, I’m meeting new people, I’m learning languages, I’m climbing mountains, and I’m starting businesses. I’m living such a varied lifestyle and meeting incredible people that inspire me along the way like you met.

Matt Bowles: Aw.

Sharon Rosenberg: I can’t imagine ever stopping. I’m getting so much from this lifestyle and it’s just so wonderful.

Matt Bowles: Amazing. I think that’s an amazing place to end the main portion of this interview. And at this point, Sharon, are you ready to move in to the lightning round?

Sharon Rosenberg: Let’s do it.

Matt Bowles: Let’s do it. All right. What is one book that has impacted you that you would recommend other people should check out?

Sharon Rosenberg: One that comes to mind, it’s called Know My Name by Chanel Miller. It’s a heavy one. A woman that wrote it, she was the same year as me at UC Santa Barbara. And it’s about the Stanford sexual assault case that happened in 2016. And she writes in detail about the whole process of taking this to court and how difficult that was. But she was a particularly influential person in that she was an advocate that actually changed a lot of these court processes around how victims of sexual harassment and assault go to trial. And I follow her on Instagram. She’s also an artist. She does illustrations. I think she’s just such an interesting, inspirational person and a very powerful writer.

Matt Bowles: Wow. I have not read that book, but that is really an important topic. So, we’re definitely going to link that up in the show notes as well. Sharon, if you could have dinner with anyone who’s currently alive today that you’ve never met, just you and that person for an evening of dinner and conversation, who would you choose?

Sharon Rosenberg: I think Trevor Noah would be a fun one. I recently read Born a Crime. Incredible book. Required reading before going to South Africa. And I also think the Daily show is hysterical. Sad that he’s not doing it anymore. But I always get the sound bites on my Instagram from recent episodes, and I would love to have dinner with him.

Matt Bowles: That would be an amazing dinner. All right, Sharon, what is one travel hack that you use that you can recommend to people?

Sharon Rosenberg: So, I’m not sure how many people know about this, and I was thinking it was more mainstream than maybe it is, but eSIMs. So, an eSIM is a SIM card that you don’t physically have, and there’s apps like Airalo, which we can maybe link to, where you can download a sim, either for a specific country, for a region or a continent, I believe. And you’re able to install it, and it’s a data package only, but you are able to top it up on this app. You don’t need to deal with dialing a number, listening to an operator in a different language, picking a complicated package. It’s very easy to pick your data, see your usage, and top it up. Going forward I believe that there will no longer be SIM card slots on iPhones. And so, this is going to be something that will need to be more mainstream. But I have been using it for about a year and a half, and it saved me a lot of time running to mini marts or going to cell phone stores with my passport and doing these lengthy processes when you can just download an eSIM.

Matt Bowles: All right, Sharon, knowing everything that you know now, if you could go back in time and give one piece of advice to your 18-year-old self, what would you say to 18-year-old Sharon?

Sharon Rosenberg: I wouldn’t tell 18-year-old Sharon a thing, I think that every step that she took, every misstep, every path that she went down that didn’t lead me in a straight line was really important in taking me on the journey that I went on. And I think that all of it was important.

Matt Bowles: Awesome. All right, Sharon, of all the places you’ve now been, what are your top three favorite travel destinations you would most recommend other people should check out?

Sharon Rosenberg: I loved Sofia, Bulgaria. I think that that’s a really interesting city. And I recommend going in the summer. I went in August, and it was sunflower season in August, so it’s actually the number one producer of sunflower oil in Europe. And the entire countryside is yellow with flowers at that time of year. It is gorgeous. I recently went to Dahab in Egypt, which not only is a hub for scuba diving, but just as a charming beachside town. On this beautiful promenade you can walk down with restaurants and cafes and just a wonderful culture and everything’s laid back and calm and chill. And you’re looking out at the Red Sea. You can see Jordan across the way, you can see Israel across the way. Just a gorgeous region.

And the last one that I would pick, I’m going to give Essaouira a shout out because Morocco just won today and Morocco’s on my mind and I really loved my experience in Morocco. As wonderful as Marrakech is, it’s a chaotic, hectic city. You’re walking through the medina and there’s donkeys and people trying to sell you things and motorcycles. And Essaouira is such a respite from that. It’s calm at seaside, it’s charming, charming white buildings with blue doors and fishermen and just chill, chill times. Really love it there.

Matt Bowles: Totally agree. I recommend it to everybody that goes to Morocco.

All right, Sharon, final question. What are your top three bucket list destinations, places you’ve not yet been highest on your list you most want to see?

Sharon Rosenberg: I really need to see the northern lights. I’m not sure if that’s going to be in Iceland. Lapland is another place to see it. It’s going to require me going somewhere very cold in the dead of winter, so I’m bracing myself for that. But given my upcoming travel, at least I’ll be packed for it. So maybe that’s in my near future. I really need to get to Japan. I’ve heard so many wonderful things about the culture, about the food. I cannot wait to go there. It’s been closed for the last several years because of COVID but it has been reopened now, and as soon as I’m afforded the opportunity to get over there, I will be doing that. And I’ve recently learned about a lake where you can swim with jellyfish that don’t sting. Where is that, Matt?

Matt Bowles: That is in the island nation of Palau.

Sharon Rosenberg: That has recently made my bucket list. Just didn’t know you could do that, but you can.

Matt Bowles: This is why we travel, you see, because we sit around talking about epic bucket list travel destinations, and we always learn things. This is literally why I ask every guest for this, because they’re always saying things to me, and I was like, ooh, I want to do that either with the bucket list or with the favorite travel places. I’m always learning from people. And this is an amazing part about immersing with nomads that prioritize travel to really cool places.

Sharon Rosenberg: You would think the more that you travel, you’ve seen everything, you’ve done everything. And it’s quite the opposite. The more that I travel, the more people I meet, the more places I’m aware of that I just have to go to.

Matt Bowles: 100% totally agree. All right, Sharon, at this point, I want you to let folks know how they can find you, connect with you, follow you on social media and learn more about Overlap. How do you want people to come into your world?

Sharon Rosenberg: Sure. You can find me on Instagram at where.is.sharon. You can see where I am and Overlap at hello.overlap. You can find more information about Overlap on www.overlap-app.com and you can find our app in the App store or in the Play Store. Overlap, nomads and travelers.

Matt Bowles: Amazing. We are going to link all of this up in the show notes. So very easy. Just go to one place at themaverickshow.com, go to the show notes for this episode. There you’re going to find the website for Overlap, how to download the app, how to find and follow Sharon, all that good stuff. Be sure that you download the app and then follow me right away. Connect with me. I’ll be your first friend. And it’s a really fun, awesome app. It’s really exciting, the speed at which you guys are building it, developing new features and all that kind of stuff. And really cool how you’re soliciting feedback from nomads on it. So super happy to be one of the early users and super excited to see where it goes.

Sharon, thank you so much for being on the show. This was amazing.

Sharon Rosenberg: Thanks for having me, Matt. This was fun.

Matt Bowles: All right, good night, everybody.

Sharon Rosenberg: Good night.