INTRO: This is part two of my interview with Ross OC Jennings, a traveling bagpiper, world record holder and cultural storyteller. In part one, Ross talked about growing up in China, learning Mandarin, connecting with his Scottish heritage, discovering the bagpipes in the UK and eventually setting out on a quest to play them in every country in the world. He shared some incredible stories about playing for the royal family in Bhutan, on a volcano in Guatemala, on top of the tallest building in the world, and in flight on a commercial airline at 35,000ft. So, if you haven’t yet heard part one, you can go back and listen to it after this one. But right now, in part two, Ross tells the story of meeting and falling in love with his husband Travis and reflects on building a relationship around a life of travel. He talks about living in Guatemala and the Philippines, traveling the world as a gay man and navigating countries where homosexuality is criminalized. Ross also reflects on what the bagpipes taught him about British colonial history, how returning to Shanghai, where he grew up in 2026, affected him, and how he thinks about the concept of home after a lifetime of living across cultures. And finally, we discuss the responsibility of travel content creators, the limitations of achievement-oriented travel goals like visiting every country, and how Ross’s understanding of meaningful travel has evolved over the years. So please enjoy the conclusion of my interview with Ross OC Jennings.

Matt Bowles: Well, let’s bring your husband Travis into this story. A lot of people ask me, both digital nomads as well as people that are curious about the digital nomad lifestyle, isn’t it difficult to find love and partnership in a lifestyle of itinerant world travel? You obviously have done that, so I would love to hear your love story. How did you and Travis initially meet?

Ross OC Jennings: I managed to meet Travis on Instagram. Once you go through all the other apps, you eventually get to Instagram or TikTok nowadays. I remember a photo of mine popped up on his feed. So, he says, I was asking advice for traveling around Indonesia because I’d never been. He did his Peace Corps service in Indonesia. And for those of you listening, the Peace Corps is sort of a government, is a government body that’s part of the US government and they do NGO type work, they teach English, they do medical stuff, etc. And so, Travis was teaching English in East Java, and so he knew Java quite well and Indonesia. I popped up on his feeds. I wanted some advice. He messaged me and I looked at his account. I was thinking, please be gay. He couldn’t tell. Went through all his pictures. And then that’s when we, I don’t know how we started chatting. He actually ghosted me for four days. Well, that’s not really ghosting. He didn’t respond because I was quite flirty. I was like, hey, if you’re ever in London, do you want to grab a beer? And he responds, I’m never in London. Five days later, I was like, hi, it’s me again. We start chatting. We schedule a Skype and we chat for three hours on this Skype. That’s when Skype existed, way before Zoom. And I pitched a gig working with the South African Tourism Board. And I invited him to come. And five, six months later, he met me in South Africa, cape town in February 2016. And that was kind of the start of it. We got on very well. And then we agreed to meet each other in different countries every couple of months. He was living in Chicago at the time I was based in London. So, the next place we met was Sri Lanka. And then we had agreed to meet either in London, Chicago, or somewhere else. And a year and a half of doing that long distance, I then convince him to quit his very secure government job. And that is when we started that travel company I mentioned with this other guy, this photographer. And at the start of 2018 was the first start of our big adventure. We had planned this four- or five-month trip around southern Africa. And at the back of that, that’s when we went to Bhutan. And yeah, we are now what year is it 2026. We’re officially 10 years down the line. And it works. The bagpipes worked.

Matt Bowles: So, looking back on it now, can you share a little bit about how you two built a lifestyle together centered around travel and any tips you might have for people that would love to travel the world with a spouse?

Ross OC Jennings: The honest answer now, with traveling and working on the road with a spouse, with a friend, whatever, business partner, is so different now from what it was 10 years ago, for sure. Five years ago. Yep. Even two years ago, which is crazy. Working on the road, we didn’t set out to be digital nomads. We set out to create a travel media company. We were happy to be based out of the UK, doing gigs and collabs with tourism boards because I’d already done that a bit. Hotel groups. It was very tourism and travel-focused. We worked with this other brilliant photographer. He was like a Nat Geo-level photographer. But after about a year, we all had different ambitions, so we went our own ways. To put it simply, Travis wanted to work back in education. I wanted to start doing trips and maybe do more bagpipe stuff. And Chris was very sort of a solid photographer. So, we broke it apart and went our own ways. Travis and I eventually linked up and worked together. But Travis—this was in 2018, 2019—then got a job working at an international school in Guatemala. And then COVID happened. So, all our travel plans and the travel business that we were trying to build just totally went to shit. And for me, that sucked because everything I was trying to build was blown out of the water. But again, I was very lucky from a country that provided support. I was looked after. We were based in Guatemala at the time, trapped there for a period of time because we couldn’t get out. And I thought, I need to pivot. I can’t travel, do workshops at schools. I didn’t want to do workshops with my bagpipes on Zoom for schools because it just killed the vibe, and I was not in the best headspace. So, I started editing videos, and I made one or two videos, shared them on a Facebook group, and then three or four months later, it got picked up by this online video academy, and they essentially asked me to teach classes on editing videos and social media. And that was such a big saving grace because then I had an income again. I then had a job, and that was a great start for me—learning how to edit videos, work in social media, work online, and actually create more of a brand out of myself and what I was doing.

Matt Bowles: What’s something about Guatemala that you discovered by living there for years that travelers coming through for a week or two usually miss.

Ross OC Jennings: I think if you’re living in a country, you learn way more, of course, than just visiting for one or two weeks. I think when people scoot in and out for a week and a half, they do come close to it, but maybe don’t fully grasp that Guatemala is a very Mayan country. They see it. They see women and men dressed in traditional gear. But I think they don’t totally grasp or understand how big a part of Guatemalan cultural identity that is. These people wearing traditional gear are representing this very ancient Indigenous culture. They are Mayan. A big proportion of the country don’t even speak Spanish as a first language. They speak a Mayan language as a first language and then Spanish as a secondary language. And many people do forget that. So, when you go there, I actually appreciated it because my Spanish wasn’t totally fluent. So, I’m talking to someone who is also speaking Spanish as a second language. They are Guatemalan, yes, but because of their accent and the cadence in which they speak, I often found it very easy to communicate with folk with my heritage. So that’s one thing. Not only that, there are 22 official Mayan groups around the country. It’s not just one Mayan identity. And the other thing, maybe you do learn this depending on the type of traveler you are after one or two weeks, but the Mayan culture and civilization existed thousands of years ago. Yes, we see it in temples, we’ve seen it in movies and stuff. It still exists. It isn’t an identity that’s kind of been trodden out despite different attempts to do so. It’s still very much there. And I think it’s such a rich part of Guatemala’s cultural fabric. And now it’s really nice to see that becoming part of the country’s pride. Sadly, in Spanish, when you’re there, when you hear things, there’s still a lot of racism and a lot of prejudice against Mayan communities, which is awful. Even in swear words, which is horrible. But that is changing, and that is wonderful. Wonderful. And one really lovely thing, the last thing I’ll say about Guatemala, because I do love it as much as I love China: if you are visiting, then take a moment to learn some Mayan languages. It goes down so, so well. There are different Mayan groups there. The largest are Kaqchikel, Qʼeqchiʼ, K’iche’, and learn some of the greetings because it is so appreciated if you say, “How are you?” or “Hello” in one of those languages versus Spanish. Yeah, that would be my one tip for when you’re going to Guatemala.

Matt Bowles: For digital nomads and slow travelers and people that can spend a longer time in one place that haven’t yet been to Guatemala, what would be your recommendations for the best way to experience the country?

Ross OC Jennings: Okay. Of course, if you can do slow travel and spend a good period of time there, get out into the western highlands as much as possible. There’s the standard route, which is often Antigua, Lake Atitlán, and then the northeast, Petén, which is the largest department, slash state. Petén is the jungle, the tropical jungle, where you find the largest Mayan cities that border Mexico. And from there, you can go across to Belize and Mexico and on to the Yucatán. If you’ve ever heard of Chichén Itzá in Mexico, in the Yucatán, Guatemala has these wonderful Mayan temples. They’re like Chichén Itzá, but way better. Sorry, Mexico. Of course, there are plenty, plenty, plenty of Mayan ruins and cities in Mexico, but I do think the extent of what you can find in Guatemala is incredible. Spend a good amount of time up there, yes, but then go into the highlands of Guatemala, that is Antigua, past Lake Atitlán, and into cities like Xela, which is another name for Quetzaltenango. That is, they say, the heart and center of the Mayan heartland, basically in the highlands. And if you explore from there into the smaller villages, you’ll get a sense of how Mayan it is. Lots of villages are very proud and wear their traditional gear. And you’ll see the women still wearing these wonderfully colored blouses. And I love the comparison to Scottish kilt tradition there a little bit, in the sense that every Mayan village and town has its own color and a certain type of embroidery. And when I was there, I eventually got to the point where I could recognize a handful of these colors and embroidery. You can actually recognize where someone comes from and be like, “Oh my God, no way. You’re from San Juan Zacatecas.” And they’ll be like, “How do you know that?” And you’re like, “Well, your blouse, your huipil.” They’re often called huipiles or blusas, blouses. Your huipil is yellow, and it’s got a certain type of embroidery. And once you learn that, it unlocks this other level of awareness when you’re in Guatemala. It gets you to appreciate the country even more.

Matt Bowles: Well, you and Travis now have a base in the Philippines. Why did you choose the Philippines?

Ross OC Jennings: Travis works in international schools still. He did in Guatemala. And then, after a stint there—after three years there—we wanted to stay, but we decided it might be a good opportunity to go elsewhere. So, he applied for different jobs, and Manila came up, one of the international schools here, which is why we moved all the way across the world to another very different, but also very similar, country. The Philippines is a wonderfully unusual Asian country because it’s very Catholic, and it was colonized so many times, which is very sad. So, the country has this strong cultural identity in itself, but it’s littered with different, very Spanish things and very American things because of its history. We never realized it was going to be so similar to Guatemala in many ways, like the processions, the Catholic traditions that appear here, the ceremonies, the slang, the belief system, which is quite interesting. But of course, it’s very unique and very different as well. Long story short, the reason we’re here is because of Travis.

Matt Bowles: What has the experience been like living there as a gay married couple?

Ross OC Jennings: The Philippines, on paper, it doesn’t look like it’s going to be the most LGBTQ-friendly country, but it actually is. It’s a very gay country. It’s a very gay-friendly country. Of course, we’re handed the foreigner privilege cards, and there’s even an acronym for that. If you’re a foreigner in the Philippines, there’s a slightly derogatory term. You are an AFAM. So, I often just outwardly refer to myself as an AFAM, a foreigner assigned in Manila. And I think that harks back to the days of U.S. occupation and a certain type of individual here. I call myself that because perhaps I want to show people, I am aware of my presence here. On top of that, I do really enjoy the gay culture, queer culture here, LGBTQ culture. It’s very visible. I don’t want to speak for the experience of queer Filipinos, gay Filipinos, trans Filipinos, but I’ve seen people here existing visibly, proudly. Maybe not more proudly than Europe or North America, but just existing and getting on with their lives. And people don’t seem to make such a big deal out of them just being themselves. Very sadly, in many other parts of the world, the trans community is treated as a battering ram, which is just so awful. Of course, I don’t watch and I don’t understand a lot of Filipino news, so I don’t know what it’s like to be trans, a trans Filipino person here. However, I’ve encountered and interacted with and met more trans people in the Philippines than I have in any other country. And I think that’s a start, which I think is wonderful. Of course, I’m in Manila, which is a very liberal, open city. As for other aspects of LGBTQ culture, our marriage is not recognized here, which is very sad. However, I like to think that things will progress over the next 10, 20 years in the Philippines and laws might change. And we’ve seen it in other neighboring countries and regions in Southeast Asia, with Thailand legalizing same-sex marriage, Nepal, I think, civil partnerships, even Taiwan recognizing same-sex marriage. So, I think things will change.

Matt Bowles: So, for you, reflecting back on traveling to 117 countries, how has being gay impacted the way that you’ve experienced the world?

Ross OC Jennings: I would say I’m very lucky because I’m what’s called a cis gay man. I’m what is supposedly deemed as straight-passing. Also, I’m white. I can navigate through the world very easily. The world’s been designed so that we can get by easy-peasy, which is very unfair. So, it has not been hard. I’m not going to say that at all. Of course, there are things at the back of my mind I’m aware of, but I’m not going to go, “Oh, no. My time in Mozambique was really bad because I was traveling there with Travis as my husband.” We had to be safe, and it’s at the back of our minds, but we were fine. At the end of the day, I can’t imagine what it would be like if we weren’t straight-passing, or if we were perhaps trans, or in another body, or acted in a different way. We were fine. And often, Travis and I, when we’re traveling, make sure we have these conversations about our experiences there. And I don’t know why, but we often seem to find ourselves in situations where we’re meeting folks that are part of our community from those countries. And I think that’s really cool. And I also think that’s perhaps because the tourism industry allows that.

Matt Bowles: Do you intentionally seek out the local LGBT communities when traveling, and can you share maybe a memorable connection that you’ve made around the world?

Ross OC Jennings: We don’t actively seek it out. We aren’t going to clubs, and we aren’t going to spaces maybe where uniquely LGBTQ folks would hang out. However, we are so open that, I don’t know, we just always seem to either attract it by chance or by default. I do like to think that the tourism industry is very liberal and open-minded, and I maybe think it’s a bit of a saving grace for different communities in some countries around the world. And based on the amount, the frequency of people I’ve met working in hotels, working in tourism as guides, it seems perhaps if you’re part of the LGBTQ community from a country, maybe you gravitate toward the tourism industry because you might be interacting with foreigners with maybe more liberal ideas, so you can be yourself. I’m not saying that’s a rule, but perhaps that’s why this has happened. And Travis and I love to have those conversations with people if they feel comfortable. We don’t want to out someone, but if we feel comfortable, we will talk about ourselves as being a couple. And then often we found, as a result of that, a guide, a local, an individual has opened up themselves and shared about what it’s like for them in that particular country. And I think that’s really cool because that is backdoor diplomacy. A government or a culture might be deemed in a certain way, but those types of conversations are really important because it does give people hope. If you’re a queer person from a very conservative country and you’re losing hope, that’s awful, and that’s so sad. But to know that there is the option of finding someone I can love or be with, and I’m not alone, I’m not a weirdo, and what I am is actually natural, I think that’s quite important. And on top of that, maybe more importantly, is having those conversations with people that are not part of our community. In Kyrgyzstan last year, we had a guide with his kid driving us around the country, and he was wonderful. Such a great guide. He’d worked with the IMF, the UN, he’d now worked in tourism at a small lodge, and he drove us around, and we’re having such great conversations. And towards the end of the trip, we just felt safe and open enough to tell him that we’re a couple. And we said, “I don’t know if you’ve guessed or not.” And he said he didn’t guess. And he had no idea that we were a couple, which we found quite shocking. And he was curious to learn more, and we were very open to answer his questions. And we were sharing with him that, look, this is an example of a queer relationship. If you have any questions or prejudices that you have, you’re welcome to ask us about that. And I think that is equally as important.

Matt Bowles: What do Western LGBTQ travelers sometimes fail to understand about queer life in other parts of the world?

Ross OC Jennings: Some LGBTQ travelers, when they go into certain parts of the world, maybe forget that there are queer communities and LGBT communities in every country we go to. We have to be very careful not to come with our version of what it’s like to be queer, what it’s like to be gay, what it’s like to be part of our community, and place that upon another culture. We’re not the ones that hold the standard. There’s not one way to be gay, there’s not one way to be queer, to be trans. There are different ways. And there’s even a term for this, and it’s called pink imperialism. We have to be very careful not to impose our way of doing it onto other cultures because it might not be right for them in that context. Given the religion, given the culture, it might not be safe to do so. We also have to remember some of these countries, let’s say a country that has only existed for 50 years or 40 years. How can we impose our concept of what we are living like onto that country when it is just still working things out? And yes, I think there’s a time and a place for fierce activism. Absolutely. But we do have to be careful that we don’t experience a guttural, intense clapback, which can actually be detrimental to our community. Sometimes things do just take a bit of time, and backdoor diplomacy is the way to go. Soft diplomacy, conversations, educating people, sitting down, having good conversations with them, rather than being like, this is my culture, you have to do it like I want to do it. That can be very dangerous.

Matt Bowles: You have traveled through a number of countries where homosexuality is criminalized. How do you navigate that? Not only in terms of safety, but also in terms of deciding how much of yourself to reveal.

Ross OC Jennings: Now that I’m older, I want to play it safe. I’ve got a partner, so I think about things in a different way. I think about my safety from the point of view of Travis, too. And if something happened to me, if I feel safe to do so, then I will share. Because I think it’s partly my duty to share what it’s like to be me if people are open to learning about it, like in the case of Kyrgyzstan. And I don’t want to say names or countries because I don’t want to put people out there that haven’t asked to be put out there. But in the Gulf, in particular, Gulf countries—the UAE, Kuwait, Qatar, Oman, Saudi Arabia—I’ve had fantastically interesting conversations, sad but wonderful conversations, where I’ve had people open up to me in the most brilliant way because I’ve opened up to them. Do I feel safe doing that? Yes, absolutely, in those countries. Some places, no, I wouldn’t do so just because you never know what might happen. How do I navigate it? A simple, really simple example is if Travis and I are traveling together in a very conservative place, the go-to is that we’ll be given a room with twin beds. If we feel safe to do so, we will ask for a double bed. Because I think it’s important to make people aware that we exist. If we don’t feel safe to do so, we’ll just leave it. In one case, in northern Mozambique, which is very Muslim, there’s an island called the Island of Mozambique, and we were working with a lodge there. We were put in one villa and given two beds. We weren’t quite sure how to play it. So, every morning, we would wake up and just mess up the other bed. I’d lie in it and make a bed angel. And then, throughout the week, we became quite close with the managers of the hotel, and they said, “Hey, you guys, just a bit of feedback. We’ve clocked you, but I want to let you know that what you did was quite sensible in messing up both beds, because the staff came back and reported on the first morning, ‘They’re not sleeping in the same bed.'” And they said, “As much as I hate to say it, they would have treated you very differently had they clocked that.” Which is sad, but again, we’re not going to let that ruin our time there. And also, we’re safe, we’re fine. Boohoo. It’s not the end of the world in that space. Perhaps it would have been an opportunity to maybe bring it up, but we didn’t feel it was our place to do so.

Matt Bowles: Well, I have heard you talk about the country of Mozambique eventually winning a very special place in your heart and choosing to return their multiple times. Can you talk about why and how that country became so special to you?

Ross OC Jennings: I first went to Mozambique in 2018, at the end of that three, four months that we worked in Southern Africa, all the way from Namibia across to Mozambique. I didn’t know anything about its history. I didn’t know anything about what to expect. It’s also a former Portuguese colony, so it was an introduction into what Portugal had done to the world, and has done to the world. So then diving into that part of colonial history was fascinating, because I know in the UK we don’t learn even about British colonial history. I know why—it’s shameful, and people don’t know how to navigate it, which I think is a shame. So, we definitely don’t learn about Portugal’s impact on the world. And so, Mozambique, being a former Portuguese colony, the history it’s gone through since independence, what it’s gone through is crazy. But also, just the beauty of it and the ethnic makeup is so different to what I’d experienced. My first encounter with it was in Portugal. I was playing the bagpipes randomly in the Azores Islands, actually on the highest point of Portugal, an extinct volcano called Pico. I think some music festival wanted me to play the bagpipes on top in January, February, I can’t remember what year, but I hiked up, played the bagpipes on top. And then this lady I met later that day had been born on the Island of Mozambique. And I remember thinking, how about—that’s not an island, it’s a country. And she’s like, “It’s an island.” And she took out Google Maps and zoomed into this tiny point, and I was like, oh, I know nothing about this country, let alone this little island. So that’s kind of the first memory peg. And then, skip a year or two later, and we made it to this island, Ilha de Moçambique, the Island of Mozambique, which gave its name to the entire country in a very roundabout way. And the history is just bonkers. It’s so beautiful, it’s so sad, it’s so phenomenal that I ended up going back a few times. And if you ever have the chance to go somewhere else in Southern Africa, I implore you to visit Mozambique also. Great food.

Matt Bowles: Well, I want to ask you now about some of your reflections on the cross-cultural connections that you’ve been able to establish through playing the bagpipes in all of these different countries around the world. Travelers are often told to try to blend in when they travel, or adopt local customs or garb or things like this. You have essentially spent 12 years doing the exact opposite—walking into communities, wearing a kilt, carrying the bagpipes. What has that taught you?

Ross OC Jennings: Yes, we’re often taught when you’re visiting a new place to be subtle, respectful, mindful of taking up too much space. And yes, as you’ve said, I’ve kind of done the exact opposite, with a kilt on, playing the bagpipes. My aim has never been to rage-bait people or to shove what I’m doing down people’s throats, but to use the music and national dress as a cultural catalyst to connect with people in a different way. Perhaps when I first started, I was not as sensitive as I am now. I would never want to make someone feel uncomfortable. I would never want to just post something or create a video just for the sake of it. It taught me a lot about myself and the space that I take up and how I should navigate the world. And it also allows me these wonderful connections with people that perhaps might not have otherwise happened. If you’re walking down the street wearing a kilt and someone walks past you, no matter where you are, they might clock it. Even in Scotland, it happens in Edinburgh, which is normal. People will stare because it’s a different sight. You don’t see kilts so much anymore. A man essentially wearing a skirt—and kilts look wonderful. Dudes look great in a hardware in a kilt. It’s such a wonderful visual. But I think that for any national dress, if a Bhutanese man walked down the street in London wearing their go—and actually I saw that once—I crossed the road to walk past this guy and say hi to him because I wanted to be like, “You look so amazing.” If you wore a thobe through New York, you would look amazing. National dress does that. I think it’s cool because it’s a conversation starter. The instrument, bagpipes, on top of it—music is the language of love. Maybe not with all bagpipe tunes, because you might be like, “The language of shut the hell up” sometimes, but it’s got me through doors and opened up interactions in these really lovely ways. Like that interaction with the police people. Maybe I would have been not arrested, but they would have made me feel very uncomfortable and taken away my driving license. But the bagpipes kind of saved me from it. I’ve been invited into interactions or events more often than not. I’ve had people open up in different ways. In Bahrain, for example, I was playing the bagpipes in the souk in Manama, and I finished playing the bagpipes and I was about to hop into a cab when these two ladies wearing full niqab, which is when faces are covered—one of them, or the woman in front of me, opened up, lifted up her niqab, looked at me, and was like, “Remember my face.” I doubt that would have happened had I not been wearing a kilt and playing the bagpipes.

Matt Bowles: So, have you found similarities between the traditional Scottish kilt and other local garb from around the world in cultures in South America, Africa, Asia and so forth?

Ross OC Jennings: Yes. The concept of wrapping a piece of cloth around you and hoiking it up above the knee or by the knee is universal. Skirts are universal. It’s an easy way of adorning something, covering yourself up. So, although the way the kilt looks, and how it sits, and how heavy it is maybe unique to Scotland, perhaps, the concept of that is very similar. You wear a lungi in South Asia, maybe that’s down to your ankle. Though other places might wear something closer to a tunic. Or, like I said, in Bhutan, you wear a go, which is hooked up. So, there are many similarities in styles of national dress. The other thing is tartan, the pattern that is on kilts. In North America, it’s often called plaid, which is just another way of knowing it—the square, checkered pattern. You see that in so many places around the world, weirdly in school uniforms. And I don’t understand why Japanese school uniforms have tartan. Guatemalan school uniforms have tartan in them. However, I think it’s just maybe out of coincidence that they’re square patterns, because the square pattern is easy to replicate. The whole garb, like the socks, shoes, et cetera. I’ve learned more about Scottish traditional gear and learned about lots of Indigenous traditional dress as a result of it, too. And it’s made me, I suppose, appreciate things even more and how important it is to preserve that.

Matt Bowles: Have there been times when playing the bagpipes turned out not to be well received in a particular place?

Ross OC Jennings: Yes, a few times. One time, playing the bagpipes in the Netherlands, I was just playing on the canal and this dude comes out of his office and just starts screaming at me. And you know what? Don’t blame him. He’s probably having a bad day, and the last thing he wants is an annoying bagpiper. I think in Amsterdam, they get quite used to visiting stag dudes, so they’re probably quite fed up with another annoying British person on holiday causing a ruckus. So that was one. So that was a good, like, okay, good point. Sorry, I’ll move on. And the other one, which was maybe more jarring because it happened early on—the first year of me traveling—was when I was in Tanzania. I wanted to get a shot of me playing the bagpipes with Kilimanjaro in the background. So, I went to Moshi. And I didn’t have enough time to do the hike, and probably wasn’t fit enough anyway. So, I thought, okay, next step, let’s just play the bagpipes on Mount Kilimanjaro. Let’s go to the foothills. And it was rainy season, so you couldn’t see much anyway, so I stayed for a couple of nights at this guest house. And then I wanted to do a tour to at least meet people and learn a bit more about where I was. And in this one village we went to, maybe it was part of the tour, but I was the only person there. These ladies were singing and dancing and wearing their traditional kanga as well. And I thought, okay, this is lovely. If you’re going to do this for me, I would love to be able to do that for you. So, I offered to play the bagpipes for them. I didn’t have my kilt, but I had my bagpipes with me. So, I played for them all. And a lot of them were laughing, they were in hysterics because they thought it was the ugliest thing they’ve ever heard. But there was this one lady who was as stony-faced as anything, honestly, face like thunder. And she was one of the older women, and I thought, God, have I offended her, or what’s up? So, I asked my guide to ask what’s up with her. She was noticeably grumpy, and he, after chatting with her, turns around and goes, “Oh, she’s not the biggest fan of that sound because the last time she heard that was before Tanzanian independence.” And that’s kind of when it hit me that this instrument has positive, great connotations for me. But I’ve gone and done that thing which, at that time, I wasn’t that aware of. I’ve gone and taken this very loud instrument, which has connotations, and kind of shoved it down someone’s throat in a way that they didn’t want to hear it. Or maybe it’s brought up memories that were not the best. So that was maybe the start of my better self-awareness.

Matt Bowles: So how did that prompt your learning journey about the history of the bagpipes and especially your attention to the history of colonialism and global power dynamics?

Ross OC Jennings: That’s when I started realizing, I suppose, that yes, bagpipes are not just Scottish. Why are they recognized around the world? Okay, British Empire. We’ve had this huge impact around the world. In a negative context, yes, I was aware of it, but maybe not on every single level. And the memory of that is probably quite traumatizing for people, so they might not want to be reminded of that. Just because this is a happy instrument for me doesn’t mean that’s the case for everyone else. On top of that, though, bagpipes have been introduced and reintroduced into places in a very interesting way. So, I’ll give you an example. In Southeast Asia, Malaysia, which was a former British colony—British Malaya, Singapore—to a lot of Southeast Asian countries, the bagpipes were reintroduced into the military, but also into something called the Scouts. So, in Malaysia, there’s a Scouts group, which I think is a Christian association. And when I was playing the bagpipes in Penang, I can’t remember how this happened, but I managed to connect with some of these Scouts one evening. And there were these Malaysian fellas, these two guys who were ethnically Tamil but Malaysian, brought up in Sarawak, spoke Malay, Tamil, Mandarin Chinese, very little English. And they could play the bagpipes. And we were able to play the same 10 tunes. Having never met each other before, having never practiced together, we were just like, “Highland Cathedral, let’s do this,” or “Scotland the Brave, let’s do this.” And it was this really bizarre, interesting moment, because how useful is it that I was able to speak to them in Mandarin? I thought that was great. But also, we were able to connect with the bagpipes, this very Scottish instrument, in Malaysia. In Penang, the same thing happened a couple of years ago. I was traveling with a good friend of mine in the highlands of Uttarakhand. We went to this village in the Himalayas called Munsyari. And in Munsyari, they have different folk music and folk songs. And what they’ve done, as a result of British influence, they’ve adopted and taken the Scottish Highland bagpipes, the bagpipes I play, and brought them into their own culture. So, they play their traditional tunes with the Great Highland bagpipes, and they wear their own traditional gear. I just think that’s so cool. They’ve taken this foreign thing, this colonizer’s instrument, adapted it, tweaked it, made it their own, and now it’s very much their own instrument. And I think, how cool is that?

Matt Bowles: Well, I know that you have now evolved your interest about the origins of various different things into a YouTube show called so Where’s It From? Can you talk about the concept of the show, how this came about, and give some examples of the types of episodes you’ve done so far?

Ross OC Jennings: My YouTube channel is called So Where’s it From? and it’s about the extraordinary stories of ordinary things. I came up with the idea when I lived in Guatemala. I was filming for a charity in the north of Guatemala, the cardamom-growing region, and I remember thinking, cardamom has no business in Guatemala. Why is it here? What on earth is cardamom doing here? I’ve never seen it in the food. I’ve seen some candy on the side of the street, but, like, why? And that forced me to then be like, well, maybe cardamom comes from here. Actually, that would be a cool story. No, it comes from India, southern South Asia. And then I did a bit of digging and thought, okay, this was introduced here as a cash crop, and it’s this invisible pillar of the Guatemalan economy, which is bizarre. From that point, and I think maybe from way earlier on, the whole “Where’s the bagpipes from?” thing, I started to formulate this concept in my mind, or this maybe lack of knowledge that we’ve all forgotten where things come from. So, I wanted to start creating videos about where stuff comes from. And nothing happened until a couple of years ago, when I thought, if I don’t do it now, then it’s never going to happen. So, I rebranded my YouTube channel, started moving away from just bagpipe-y travel-type stuff, and I thought, I want to do something which turns travel content into travel educational content and takes people on a journey using a familiar thing that’s in our kitchens, in our lives, that we take for granted, and takes them to somewhere they never imagined they would be taken. Could do, for example, apples. Maybe, Matt, you know, where do apples come from? The viewer, ask yourself if you maybe know this already. Have a think: where do apples come from? I was asked that question by my dad’s friend a couple of years ago, and he handed me a book and he said, “Open the front page.” And I opened it, and it showed a picture of a wild apple forest in Kazakhstan. And that blew my mind. I was like, oh my God, that’s crazy. Because if you’re from the States, Canada, Australia, Japan, you think, well, apples have always been here, haven’t they? Turns out all apples can be genetically traced to the Tian Shan Mountains of Kazakhstan. And last year I pitched this YouTube channel video idea to the tourism board in Kazakhstan, and they supported me on filming an episode. So, it’s a new channel. I’m still a small creator. I’m learning lots, still learning how to tell stories, edit videos, do all of this. YouTube is a new world for me, but it’s so gratifying. And for the first time—hold on, this is cheesy—for the first time, a couple of weeks ago, honestly, Matt, I thought to myself, I know what I’m doing, finally. And I feel like it’s my duty—not my duty—I really want to tell these stories because I’ve been so lucky to travel around the world, and if I can change people’s perception of a thing that they use, do, and encourage someone to visit somewhere in a different way than, wow, I’ve sort of done my job. And my most recent episode on apples seems to have done that. It’s done really well. And the conversations that are happening underneath, the questions, and the curiosity have just been mind-blowingly eye-opening, but also heartwarming. People have been so lovely, not just complimenting but also challenging as well. And I think that’s important—challenging me on stuff, on information that I’ve shared, facts that I’ve shared. And it’s just been really cool. And I’ve had people chatting to each other, people that are interested in apple growing and grafting, and all these different worlds that I knew nothing about have really enjoyed the video. So, it’s given me this big tick to justify the amount of time and money I’ve spent doing this and perhaps for what I’m going for. And I’m going for an Emmy, Matt. I’m going for it.

Matt Bowles: Well, I have learned a lot from your show. I will tell you that. I have had most of my experiences eating dragon fruit in Asia. And then I watched your video about dragon fruit and I realized that’s not from Asia.

Ross OC Jennings: Very true. It is not. I grew up thinking, of course this thing’s from Asia with a name Lala that and I’m slightly insinuated it in my video. But perhaps it was this big marketing ploy to get us to eat this fruit because in Guatemala and Mexico, where it comes from definitely ain’t called dragon fruit, but it definitely has a nicer ring to it than Pitahaya.

Matt Bowles: Well, I love the way that you are doing the shows and incorporating the history and the fun facts of things that most people didn’t know, and then how you incorporate the travel and the global perspective and all that stuff into one place. So, we will definitely link that up so that people can check it out in the show notes. I want to also ask you about your experience returning to China, returning to Shanghai earlier this year, which is 30 years after you originally moved there at six years old in 1996. I’m curious for you, what were you feeling when you went back and spent time there earlier this year? How much of a cultural connection did you still feel to it?

Ross OC Jennings: As a family, my parents left in 2018. We did a big family gathering in 2017 to kind of say goodbye, pack up the house. And then my parents left bit by bit over the next year until 2018. So, I hadn’t been back for nine years. I didn’t really have much interest in going back. I wanted to go everywhere else because I’d grown up there. I traveled lots, and I wanted to do other things. But then, living nearby in the Philippines, what, an hour and a half flight away, a friend of mine, one of my best pals, who I usually travel with once a year, called Manya, he wanted to always travel there with me. He thought, if I’m going to China, I want you to take me there, and I want you to show me what was your home, your experience of it. But I also want to do all the touristy stuff. So, I planned a trip, and we went there this year in April 2026, and I started planning the trip last year, and it just made me realize how much China has been part of my life and my family’s life. And I started to really yearn for it and miss it. And visiting this year was both a nostalgic, heartwarming experience. Yes, maybe frustrating in some sort of ways. Sad. And I thought about this after I left—the metaphor that I like to share. Visiting Shanghai was like visiting an old relative with dementia, because you recognize them. I recognize Shanghai. Shanghai did not recognize me. And why would it, as a part of my life? Shanghai wasn’t going to be like, “Oh, yes, cool, you’re back.” Of course, it’s not. But it’s just a weird feeling because it’s changed so much, and nothing of our family life and my experience was still there. Really, things have changed. I even went back to our old house. I stood outside and just burst into tears. And my friend Manya was like, “This is bizarre because I’m looking at a bunch of bricks, but you’re looking at a bunch of bricks that is hugely tied to your upbringing.” And the house had been painted. It’d been very different. They were renovating it, so it looked very different, but it was still familiar in a way. And that’s fine. I’m not complaining. It’s how it is. It was nice to go back. I actually really enjoyed visiting other cities that I hadn’t been to since I was a kid. We went to Beijing. Beijing’s a big tourist city. Not my favorite place because it’s just so vast. But I hadn’t been to Chengdu in years, and I fell in flipping love with Chengdu. We had such a great time there. Fun to walk around, get about. Chinas changed so much in the nine years since I’ve not been there. Everything’s app-focused on your phone, and it is just so incredible and impressive how things work, how things function, and how smooth everything seems to flow compared to the rest of the world. Getting on trains, things leaving on time in the UK—not a chance. So, I loved it, and I cannot wait to get back.

Matt Bowles: So, reflecting back on it now, how did Shanghai and China impact and shape the person that you are today?

Ross OC Jennings: There’s so many levels to it. One, having your home be a place that’s not ethnically where your home is. Like many immigrants have that same sense. If you’re an immigrant to any country, you’re growing up in a society that is not where you’re from, supposedly. So, there’s one side of that, I suppose. The other thing is maybe an appreciation of this ancient culture that we do take for granted. In Europe and North America, you’re told there’s one way of doing things, and there’s one way that the world should be run and how society should grow and be constructed. China is doing it in its own way, and we’re seeing the impact of that, and we’re seeing how society does evolve, how society does interact with each other. I’m not saying one is necessarily way better than the other. There are just different ways of doing things. And in China, it just seems like there’s no other way of doing it. On a very simple level, there’s just so many people in China all at the same time. If it didn’t work so efficiently, I think people would get upset. So, it has to work like that. It has to work like that. And so, the government makes sure it does. Things are valued very differently. East Asian culture, and even the Chinese diaspora around the world, you often see in Chinese communities, they value things in a very different way. To Western societies, you are a part of your society. You are not the be-all and end-all. The world doesn’t revolve around you. You’re a little cog in a bigger machine. So that’s maybe impacted how I try and navigate things. I don’t expect the world to move for me. Why should I? And often I think maybe in European culture, North America, you think that they will do, and you’re taught you can do whatever you want. That’s wonderful. Those are great messages. But bear in mind that you are part of a greater thing and a greater good. And that is part of maybe the belief system of not just China, but different cultures in Asia and East Asia. And I hold that in my mind a lot. How has it shaped me? Maybe from an early age, the chance and opportunity to speak other languages that are vastly different from English has maybe shaped my brain in a very different way to how it would be if you were only brought up with one language, too. And now I suppose I seek Chinese culture and aspects of that no matter where I go, even though I’m not ethnically Chinese. I find it fascinating and hyper-interesting to see the Chinese Diaspora in Panama, the Caribbean, South America, Europe. And I think it’s fascinating and something that we don’t learn about in Europe, because why would we?

Matt Bowles: Ross, how do you currently think about the concept of home? What does that mean to you today?

Ross OC Jennings: Home can mean many things. I think I am very lucky that I do feel at home in many locations, but I also do feel like a foreigner in all those locations at the same time. And home is tied to identity. Home is tied to culture, ethnicity. Everyone’s brought up in very different ways. But for me, I do feel very at home in Scotland. In the UK, my family home, I feel at home there. I didn’t know how important that was to me until COVID happened in Guatemala. And I remember talking to somebody—I think it was actually an interview or a podcast—and they asked me, “Do you miss Scotland?” And I burst into tears. It came out of nowhere. And that’s when it hit me how much I really value that part of my heritage and being able to call Scotland my home. Unfortunately, though, in Scotland, I don’t often get treated like I’m from there because of my accent. I’ve got a very English accent, so I feel nervous about that. And when I’m speaking and I say I’m Scottish to someone from Scotland, sometimes the immediate reaction is, “No, you’re not from Scotland. You’re not from here.” And I get where they’re coming from. I haven’t been through the same experiences that they have, but I’ve chosen that place as my home. And sometimes you do need that. I feel very at home also in China, but I know I will always be a foreigner. My first home with Travis was Guatemala, and I will always have that strong connection to that country, whether I like it or not. I have so much love for it. One of our best friends is from Guatemala, who we talk to every day. She’s my sister at this point. And in all those places, I would be happy to leave a toothbrush.

Matt Bowles: So, you’ve gone from documenting your own adventures to telling stories about other people’s cultures and traditions. What responsibility do you think content creators have to the people and places they make content about?

Ross OC Jennings: Content creators have a huge responsibility in how they shape a narrative or tell someone else’s story, especially if it’s not your own story. Now, the way that social media is evolving and has evolved over the past year or two years, it’s often for virality rather than for content. And that doesn’t necessarily pull the best parts out of humans. So, people do things for the wrong reasons. And maybe that’s always been the case with fame and the media and news, et cetera. People love to be shocked, and shocking stuff does do well. It’s not my quote, and it’s a cheesy quote: “With great power comes great responsibility.” But it’s true. If you’ve got a lot of followers and people are listening to you, you’ve got a responsibility to make sure what you’re doing has some sort of moral compass to it. I’m not a huge creator, but I’ve taken the stance that with my So Where’s It From? videos on YouTube, I won’t include a fact unless the fact can be verified three times and from reputable sources. Of course, I use AI tools to help me fact-check stuff and pull up certain facts. But often, if you click through to those resources, sometimes resources will be pulled from an article, a blog post, which is not like a peer-reviewed study. And it’s shocking how easy it is to twist stuff. So, I try and make sure facts and things are backed up from studies and scientists, people that actually have degrees in things. Otherwise, I won’t share it. So, when you are telling someone’s story, provide them the platform so they can tell that story rather than you shaping it. And I’ve really learned this from my next video, the next script I’m writing for my upcoming episodes on nutmeg. Nutmeg has a wonderful history and sad, awful history related to its trade around the world. And there’s a genocide involved in it. I didn’t know that, and that is awful. So, learning how to communicate that and how best to communicate that story, because it’s not my story to tell, has been an interesting learning curve. And the last thing there is, history is always written by the victors, isn’t it? So, in the past 1,200 years, we’ve had all these colonial powers around the world rewriting and reshaping history and facts and information. And we’ve got to be very careful because, in many places—for example, in Indonesia, when I was filming this nutmeg video—I met this lecturer who said a lot of Indonesian history has been written from the point of view of the Dutch. So, Indonesians are learning about their own history from the Dutch perspective, from the Dutch lens, not from their own Indonesian lens. And that needs to be restored and reordered. And that’s probably the same for many countries that had a former colonial power for the past 50, 100, 200 years. In India, that’s probably the same thing. They’re learning history through what the British wrote about it. And that’s problematic and needs to be readjusted.

Matt Bowles: When you create a goal or a quest like “travel to every country in the world” and you announce that and you pursue that, does travel itself then risk becoming achievement oriented? And if so, how have you dealt with that and resisted that?

Ross OC Jennings: I’ll be honest and say that was my goal from the start when I decided I wanted a bagpipe in every country. This young 20-year-old being like, “I want to be the first person to do this.” The arrogance of that. If that’s the spark that ignites the fire for you as a traveler, as it did for me, that’s fine. But allow yourself to evolve, allow that to evolve and change, because you’ll probably pretty quickly find out that’s not the best part of it, being the first person to do it. It’s the journey. As we know, the journey is better than the destination. Sometimes, if you have these goals in mind and you’re a country collector and people are coming for you for that, if that’s what got you going, that’s fine, but maybe reassess how you’re doing that, what you’re learning from it, et cetera. We all have our different reasons to travel. Travel can be a force for good, can be not the best force for good. How do I navigate that? My journey has evolved. I’m in no rush whatsoever. If someone ended up beating me with the whole bagpipe journey, great, cool. I will be the second, third, fourth, 12th bagpiper, whatever. It’s not what I’ve taken away from the journey. And with that, if you have a number-oriented goal, bear that in mind too. And something I try and reflect on, one of my big lessons from all my travels, which came to me as a result of being asked this: “What was the one big lesson you’ve learned from traveling, Ross?” I got asked that whilst catching a ride in Lithuania, and it would be, say, “Be open to having your opinions changed.” We all might have pre-formed opinions of stuff, and that’s fine, that’s cool. Of course, we have, because society shapes that. So does education and how we’ve lived and our own experiences. But at least be open to the idea that those could be changed. And even if you don’t change your opinion, that’s fine. But you will learn something, I guarantee you.

Matt Bowles: So, if you had completed this quest, let’s say, to play the bagpipes in every country in five years instead of taking over a decade, what would you have missed.

Ross OC Jennings: If the goal was more important than the process, I think I probably would have been a bit more cutthroat with interactions if things are timed, maybe more ruthless in how I interacted with people, what I did, the time I allowed for romances, perhaps. I might not be with Travis. I might not have made the friendships that I’ve made. I might not have had the opportunity to live in Guatemala, Philippines or other places. Would I regret that? I don’t know. Probably. I can say that now, yes, because it’s not always good to be in a rush. Slow travel as we know, and that’s how you travel, Matt, is really gratifying. You can have interactions you otherwise wouldn’t have had, and I think your travel experiences become less transactional as a result of that.

Matt Bowles: So how has the meaning of travel evolved for you personally when you think back to, let’s say, getting on that plane in 2014 to go to Tunisia, all the way up until today, what has that evolution been like and what does travel now mean to you today?

Ross OC Jennings: The bagpipe travel in itself, I’ve decided, whilst it was a journey to be shared with everybody, and that was the thing I was going for, that’s become more of a personal journey and stories for me, and that’s impacted even how I’m sharing it. I feel less of a need to tell people about the journey I’ve been on because I’m like, well, that’s my story. It doesn’t need to be everyone else’s, and that’s fine. So, it’s become maybe more personal. I have appreciated how social media has encouraged travel over the past 10, 15 years and the good that it has done, but I’m now questioning the good that it offers and the impact it has now. I miss how travel was before smartphones, the excitement of it, the unknown. And as I said earlier, first impressions are really important, and that’s ruined when you’ve already been shown a photo of something. So maybe it makes us less excited about places because knowing every single thing about the place that you’re going to when you’re traveling isn’t necessarily a good thing. Leave things to the imagination. Leave things to surprise. Because the best stories and the best interactions do always happen when there’s a fuck-up.

Matt Bowles: Ross, I think that is actually the perfect place to end the main portion of this interview. And at this point, are you ready to move in to The Lightning Round?

Ross OC Jennings: Yes, absolutely.

Matt Bowles: Let’s do it. All right. What is one book that you would recommend that people should read?

Ross OC Jennings: Prisoners of Geography, first book and second book.

Matt Bowles: All right, what is one travel hack that you use that you can recommend?

Ross OC Jennings: I always travel with a type of sari from a community in Java. It’s tied into a loop and it’s this really soft cotton fabric. It’s awesome. Ends up being a blanket if you don’t have one covering your face during COVID It was amazing because I could hide into it when you had to wear masks on the plane. Brilliant.

Matt Bowles: Alright, who is one person currently alive today that you’ve never met, that you’d most love to have dinner with? Just you and that person for an evening of dinner and conversation?

Ross OC Jennings: Simon Reeve. He’s a British journalist who I suppose one of my heroes. I used to love his documentaries and the way he used to tell stories about the places he visited. He doesn’t care too much about social media. He cares about really great, honest storytelling.

Matt Bowles: All right, Ross, 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 Ross?

Ross OC Jennings: Keep going. I wouldn’t be the person I am today if it wasn’t for the experiences I’ve had up to this point.

Matt Bowles: Okay, of all the places you have now traveled, what are three of your favorite destinations you would most recommend other people should definitely check out?

Ross OC Jennings: Mozambique, Guatemala and China.

Matt Bowles: All right, last question. What are currently your top three bucket list destinations where you have not yet been you would most love to visit?

Ross OC Jennings: Iran. That’s always up there.  Algeria.  And one of the Polynesian islands. I know very little about them, but perhaps Kiribati or Vanuatu. So out there, I know very little about them. So, let’s just choose Kiribati because that’s really out there.

Matt Bowles: Amazing. All right, Ross, at this point, the first thing I’ll want to ask you about is your upcoming keynote speech at the Extraordinary Travel Festival. If people would like to come meet you in person, I am also going to be there so they can hang out with both of us. This is happening in Bangkok, Thailand, October 22nd to the 25th. And what will your keynote talk be about? What can people expect?

Ross OC Jennings: So, my keynote is going to be about having a universal icebreaker. My universal icebreaker through my past few years of traveling has been the bagpipes, and using this as a conduit to meet people, to have these cultural interactions, and just putting the question out there that maybe we all have that in some sort of way, or is there some way that we could work that into how we travel. And it’ll be the first keynote speech I’ve done in a while. So I’m very excited because I love doing talks in person, and to be able to pair up with this instrument I love is even more gratifying.

Matt Bowles: It’s going to be awesome. If anybody would like to join us there, folks, we’re going to put a link in the show notes. You can also just go, if you’re at your computer right now, and type in extraordinarytravelfest.com. Go to the website, and then if you use the code MAVERICK, you can get a $100 discount on your ticket. And then shoot me a DM on Instagram, @maverickshowpod. Let me know you’re coming, and then we can plan to link up at the event. You can hang out with me and Ross and a whole bunch of other Maverick Show guests that are going to be there, both speaking and attending. I am actually going to be moderating a session as well. So, it’ll be a super, super fun and interesting group of people. So hopefully you can come through. And then, Ross, beyond that, how can people find you, follow you on social media, check out your amazing YouTube videos? How do you want people to come into your world?

Ross OC Jennings: So, you can find me on YouTube under So Where’s it From? Very simple or Instagram is probably the best one. Very different handle. It’s @thefirstpiper. Easy peasy. Drop me a message.

Matt Bowles: We are also going to link all that up in the show notes. So, you can just go to one place at themaverickshow.com go to the show notes. For this episode, we’ll have direct links for all the ways to find, follow and connect with Ross, how to get your discount on your Extraordinary Travel Festival ticket, and links to everything else that we have discussed in this episode. Ross, this was amazing, brother. Thank you so much for coming on the show.

Ross OC Jennings: Thank you very much for having me, Matt and I look forward to hearing all your other episodes.

Matt Bowles: All right, good night, everybody.