Matt Bowles: My guest today is Dan Demsky. He is the co-founder and CEO of Unbound Merino, a premium clothing brand that has redefined minimalist high-performance fashion. With a focus on creating versatile, timeless garments from Merino wool. Dan has built Unbound Merino into an eight-figure global business while working fully remotely as a digital nomad. Since launching the company with a highly successful crowdfunding campaign, Unbound Merino has grown to be a $40 million global brand, beloved by travelers and anyone looking to simplify their wardrobe with sustainable multifunctional clothing.

Dan, welcome to the show.

Dan Demsky: Hey, how are you? Thanks for having of me.

Matt Bowles: I am good, brother. I am so excited to have you here and talk about all of the stuff that you are up to. But let’s just start off by talking about where we are recording from today and the fact that we have agreed to make this a wine night. We are starting early. This is sort of aperitivo hour as they say in Italy. So, let’s also talk about what we are drinking. I am actually in the Blue Ridge Mountains of Asheville, NC today and I have opened a bottle of Montefalco Sagrantino from Ital, Italy. A very nice red wine. I’m going to be drinking through that throughout the episode. But where are you, Dan, today and what are you drinking?

Dan Demsky: Well, I’m drinking a Malbec. Can you guess where I am? It’s local.

Matt Bowles: I am guessing you are somewhere in Argentina, my friend. I spent a lot of time in Argentina. It was a very seminal part of my nomad journey because it was my very first destination in 2013 when I left LA. I’ve been back many times. I’ve been wine tasting in Mendoza and all the things. So, cheers to you, my friend. Are you in Buenos Aires today?

Dan Demsky: I am in Buenos Aires, and I went to a local corner store, and I grabbed a Malbec. I have no idea if it’s going to be good, but I felt it’s the right wine for the occasion to show where I am.

Matt Bowles: Very apropos. I always enjoy a good Malbec from Argentina. Well, I want to also give folks a sense of your backstory. Can you share a little bit about where you grew up and also when you think back on how your entrepreneurial tendencies started to develop? Because I know that started really young.

Dan Demsky: Yeah, you know, I’m one of those people where I’ve just always been an entrepreneur. It’s sort of in my blood. You know, when I was young, when it snowed, I looked okay. Well, people need to get their snow cleared. When I was old enough to deliver newspapers, as I was thinking, I only have 12 deliveries on my route. I want it to be 50 deliveries. So, I would knock on doors, and I would sell subscriptions to make my route bigger so I can make more money. And I always had that drive. My brain was always trying to figure out how can I make that extra buck. And it’s never been about money to me. I still don’t think I’m someone who cares too much about the money, but the building of something or the challenge. I wasn’t into sports. This was kind of my sport. It’s been to me since I was a young boy back in Toronto, Canada.

Matt Bowles: Man, Toronto is one of my favorite cities. And I will tell you that I went to high school in Buffalo, New York, which for folks that don’t know, is about two-hour drive from Toronto. And you had the 19-year-old drinking age, and we had the 21-year-old drinking age. And you also had an incredibly epic city that was a lot closer to Buffalo than New York City was. And so, we were up in Toronto all the time. And I have amazing memories from that city.

Dan Demsky: Well, lately my friends have been going to Buffalo because they’ve all decided to become Buffalo Bills fans. So that’s a regular pilgrimage and a pretty insane one. I went to my first Bills game mid-December or near the end of December, and it was in Fahrenheit, 8 degrees, and people were without shirts with Go Bills painted on their chest. It’s insane. I’ve never seen a group of people like this in my life.

Matt Bowles: The Bills mafia. Yes, that’s exactly how they roll. You know, it was interesting because back when I was there, that was in the Jim Kelly, Andre Reed, Thurman Thomas era. And the Bills went to four Consecutive Super Bowls. They lost all four Super Bowls, and then they didn’t make the playoffs for 17 consecutive years. So now that they’re good again, it is a very fun time to be watching the Buffalo Bills. So that Is fun.

Dan Demsky: And explains why my friends all hopped on the bandwagon.

Matt Bowles: Exactly. So, let’s talk a little bit about growing up in Toronto. Also, how did your interest in travel develop? I’m curious, because one of the things that I love about Toronto is how remarkably culturally diverse it is. I mean, there are people from all over the world in Toronto. What was your experience like as a kid growing up in that environment? And how did your interest in the world and in travel start to develop?

Dan Demsky: Well, it started in high school when I really started to get into music. My buddies and all the concerts we wanted to see were down in the States, and we didn’t have quite enough money to be able to figure out how to get a plane ticket or tickets to the concert or 17, 18 years old. There were a few bands we really loved, and we just wanted to hit the road and go see them. So, this was sort of the start of our entrepreneurial journey because, A, we needed to figure out how to make some money to be able to go to these shows. But then we started going to these shows. We had these road trips. And I remember reading the book On the Road back then, if you’re right On the Road?

Matt Bowles: By Jack Kerouac?

Dan Demsky: Yeah. And I just felt, and I know that’s almost a cliche of people who start to travel, they think they’re the characters from On the Road, but we connected with that, and we felt like we were having these adventures, and we just had this thirst for more. So, it started with these road trips, and that was the nucleus of my passion for travel. But when it really started it was in my early 20s. One of my older brothers, I have two older brothers, he felt like I should see more of the world. And I don’t know what compelled him to care so much about me seeing the world and stepping outside my comfort zone, but he saw me starting to work really hard on my first business. And you have to go beyond a road trip into the United States. You need to go somewhere.

And for my birthday, he said, I’m going to buy you a plane ticket, round trip, anywhere in Asia. And he picked Asia. He said, you can go to Thailand, you can go to Japan, you can go to China. You pick. And I picked Japan because it just spoke to me. And I tried to say, I’m like, dude, you can’t buy me a flight because this is a crazy president and he’s like, I’m either going to burn the money or I’m going to buy the plane ticket. So, the money’s gone for me. So, I booked this flight to Tokyo, and I went by myself for one month. And that’s when I just cracked into a whole new level. This was before social media, so it wasn’t like I was looking at all the spots on TikTok or Facebook to find like, what’s the cool place to go. I just felt like I was thrown into the deep end and I was exploring places where no one was speaking English. Everything was weird.

And I used to just write every day, just trying to unpack all that was going on in my head. And from that moment on, I had the bug. It was truly life changing and surely the greatest gift I ever had because that opened up who I felt like I really was inside. And this passion for travel was really born.

Matt Bowles: Well, I will tell you this. I have been traveling the world for many years as a full-time nomad and seen a lot of places before I ever went to Tokyo. And then in 2017, I as well went to Tokyo for my first time by myself for a month. And even though I had been traveling the world for years and I had seen all of these other places, there is nothing like landing in Tokyo for the first time. I mean, just because there is nothing like Tokyo and the rest of the planet, can you share for people what was that experience like when you think back your very first time in Tokyo?

Dan Demsky: You know, I remember very clearly feeling like this is what it must feel like to go to another planet where their civilization, things were similar, but everything was different. You walk down the street and the behavior of people who are just going about their day, it’s different. Like, and everything you look at, everything you process, it just doesn’t feel like at home.

I remember going into a 711 that’s very big in Japan. On the outside it looks like a 7 11, but once you walk in, you’re, what is all this stuff? Everything’s hilarious and cute with the weird mascot packaging and you have the weird squid that they’re selling to the rice balls. And everything was so stimulating and so different. All their customs are different. I’m used to being in Toronto where it’s incredibly multicultural and then you’re in Japan where it’s kind of like a Japanese culture and they preserve it, and they love it and they cherish their culture.

And I am so happy they do that because it’s a beautiful culture with incredible customs, incredible history, and it’s so nice to be able to go in there and see something so pure handed down from generation to generation to generation. And it was stimulus overload being there. I’ll never forget the first time, and I’ve been back quite a few times since then. My brother who got me the ticket, he ended up moving there. So, I visit him every couple of years. And it never gets boring. It gets better every single time.

Matt Bowles: I agree, man, because after I went for my first time, I’ve been back multiple times as well. And then I wanted to see different parts of Japan. So, then I went back, and I stayed in Osaka for a month and then I went back again, and I stayed in Kyoto for a month. And then I started traveling around and going out to the islands like Naoshima and Miwajima and going to Hiroshima. And seeing some of these different parts of Japan. So now that you’ve been back multiple times, what are some of the other highlights of Japan or reflections or maybe things you’d put people on to have never been to Japan if they wanted to go for the first time? What for you are some of your absolutely favorite things about it?

Dan Demsky: Now I’m a big city guy and when I go back, I tend to go to Tokyo. And 95% my time I’ve now spent in Japan has been in Tokyo. On my first trip, I really got to see more of the country. I went all the way down into Kishū, did go to Miyajima, Hiroshima, Nagasaki and Beppu. One of my favorite experiences I had in Japan on that first trip was I went to Beppu, which is very famous for their natural hot springs. And I was staying in this hostel. And someone created a map to a natural hot spring that was maybe like a three-hour hike, of a sort of mountain. And it had some pictures, and it had some drawings, and you see this tree and you turn right, and you go up here and you go around this rock and it’s not Google Maps, we didn’t have that back then.

So, you had to rely on this hand drawn, half photographed, weird map that they left in a hostel for someone else to find. And went by myself. And I was just tracking this. Felt like I was on a treasure hunt. I was like, oh my God, I went too far. I don’t see this rock. I backtracked a little bit. I found it and I was walking for what seemed like all morning and just looking for this natural hot spring with this unbelievable view of Beppu, which is overlooking onto a bay and looking down on this mountain. And it took me hours, but I finally found it. And when I get there, there’s this old, naked Japanese man sitting in this hot spring. And he’s looking at me with this, like, shocked look on his face. Like, seeing this white Canadian guy. It’s like, what is this person doing here? It is like he was seeing an alien.

And I just took my shirt off, dropped my pants, and I don’t care. I don’t never see this guy again. I’m getting in there. My bones were aching. And I climbed into that hot spring and just felt my body melting. And he was sort of a little uncomfortable, but then he settled in. And I’ll never forget just the steam rising off that water and how my body felt just overlooking this insane vista. And that was one of the coolest travel experiences I ever had. But the highlight of that was the guy’s face as if he was just. It was so shocking for him to see me. So that was really cool. And I felt in Beppu, I got that a lot. Where there didn’t seem to be a lot of tourism there. So, a lot of the people were very, very excited for a foreigner to be there, especially if they spoke any English and they wanted to try to speak English with me, have beers with me and Izakaya and eat food and experiences like that. That’s the high you’re always chasing or I’m always chasing with travel.

Matt Bowles: So, you have this incredible first experience in Japan fundamentally impacts you in a very transformative way. When you return from that, what then path or trajectory does that set you on? What priorities then do you now have in your life with regard to travel and how did you start thinking about the entrepreneurship and how that might be able to integrate with travel? What was the path from right after you finished the Japan trip?

Dan Demsky: I think that Japan trip was formative for me. One of the things was I was just starting out with my first business, and I didn’t really have a ton of money to be able to go and live it up. I had a budget. It was a finite budget. I don’t remember the exact amount, but if I averaged out how much money I could spend every single day, let’s just say it was a hundred dollars or something that included everything, accommodation and all that I could eat. So, if I went a few days where I only spent $40, I could splurge a little bit on the third or fourth day, and if I splurge a little bit, I have to dial it back a little bit. And I was keeping really tight notes in this little journal to make sure that I wasn’t overspending because I was on a really tight budget.

And that trip was life changing. It was truly one of the greatest experiences of my entire life. And I think what I got from that was the realization that I didn’t even need much money to have a life-changing experience. It can be expensive, but it doesn’t have to be. Because the way I did Japan, of course I got the ticket for free. That was a gift. But just going about my life there and Tokyo at the time was quite expensive relative to Toronto. So, I just had this mentality that you don’t even need money, you just got to get to the place just a bit, you can figure it out.

So, from there on out, as I was building my business, even though I didn’t have money to start and just get me to the next place, as long as I can go, as long as I can get my feet on the ground in a new country, I’m going to have an experience. And it was a balancing act between going and having those experiences and coming back and building my business, which, you know, at the time was not a remote digital nomad business. It was in Toronto. I needed to be in Toronto. I worked really hard. I was passionate about the entrepreneurship, but I was always looking for those little adventures on the side.

Matt Bowles: Well, what were then some of your subsequent adventures and subsequent trips? How did you start selecting the travel destinations that you wanted to go to in planning those trips?

Dan Demsky: It depends if I was going on my own or with a friend. I remember I was with my buddy Dima, who’s my business partner in my current business, lifelong best friend. I’m like, let’s go to Europe. I really want to go to Europe. But he said, I really want to go to Prague. I’ve always wanted to go to the Czech Republic. I said, why? I don’t know. I saw a picture of this pork with cabbage. Sounds like a good enough reason to go. Let’s go.

So, I had no previous desire to go to Czech Republic, but he wanted to go. I’m in. So, we booked a few weeks in Czech Republic, starting in Prague, checked out a couple local towns nearby. But then when we realized ahead of that trip, well, we’re already going to be in Europe. Where else can we go that’s nearby? And we started looking at what were easy train rides from Prague, and we saw Berlin. I’m like, okay, that sounds cool. Why don’t we add Berlin in there, and I don’t really overthink it. I’m in Argentina right now. This is my third year in a row coming to Buenos Aires because it’s January. It’s the summertime here. I’m from Toronto. I’m escaping the winter.

The first time I ever came to Buenos Aires is because I was listening to my other business partner and other best bud talk about Fugazetta, which is this Argentinian pizza has no sauce. It’s just cheese and onions. And he’s been talking about it for our whole lives, saying it’s the greatest thing in the world. I kid you not, the main reason I came here, well, the main reason was the weather. But the reason I picked Buenos Aires was because there’s a lot of places with great weather in January, was I wanted to eat the pizza. I don’t need much. There’s always something to figure out in a new country. There are always great people. to meet.  There’s always stuffed to learn.

So, I’m just like, let’s go for the pizza. I was dying to review this pizza because he said it’s better than any pizza, you’d ever get in New York City. And I thought that was insane, because at the time, I’m thinking New York City pizza is the greatest pizza in the world. It’s better than Italy. There’s no way Argentina has better pizza. So, I flew 14 hours south to Buenos Aires to go to this very specific pizza place that he said makes the best pizza that’s better than Di Fara pizza, which I would at the time argue was the best pizza in the world. Just to review it. And I bit into it, and it was damn good. But it wasn’t as good as New York pizza.

Matt Bowles: It is absolutely not as good as New York pizza, man. No way.  I love that story, though, man. Well, I know you’ve traveled quite extensively around South America as well and have been to a lot of different places. At this point. I also wanted to ask you about the trip that you took to Ecuador. Can you talk about that one?

Dan Demsky: Yeah. So that one is different in the sense that it was a guided trip with a group of entrepreneurs. To my travel styles, I go with very little planned. I will plan maybe a couple things that I really curious to eat and that’s about it. Maybe know a couple areas I want to go, maybe try to see a sporting event. There are a few things I try to check off that I tend to enjoy. But I can go to a place for a long period of time with very little plan. And that’s usually how I like to travel.

In this case, it was a guided trip where every single day, every detail was planned with this group, and I was just along for the ride. And Ecuador is not a place that was high up on my list. I didn’t know much about it, but it was centered around a climb of Mount Cotopaxi, which I think is the highest mountain in Ecuador, second highest volcano in South America. I don’t know. I’ve never done anything like this in my life. And that trip pushed me to my limits. I mean, leading up to the mountain climb, we went to the ring of volcanoes somewhere in the Andes, and we hiked for miles and miles. And we had tents. And I said, what do we have tents for? Where are we camping? It’s like, don’t ask questions. Just make sure you have water. Yes. Sunscreen. And if you want to have a notebook, you can have a notebook.

And we hiked, and I thought we were going to go find this beautiful place and all camp together and have this beautiful experience. That was not the plan. The plan was they were dropping us off one by one and then continuing on. And we were nowhere near each other. So even if I had my technology with me, which I didn’t, there’d clearly be no signal. I was literally in the middle of nowhere. And they dropped me off in the most incredible, scenic place I’ve ever seen. I pitched a tent, and they said, we’ll come back and get you in 24 hours. And what do I do? They’re like, you’re by yourself. And I had nothing but a pen and paper, some water, a protein bar, and 24 hours to sit by myself in the most incredible place I’ve ever seen.

And that went on for 24 hours. And I’ve never cracked more deeply into my own brain. Almost like we’re so stimulated with all of our technology, with all of our work, with all the things happening, to be that still, I felt like I was able to be reacquainted with my own brain. Like, I remember this one thought I had where I’m like, oh, that’s how I think. I forgot how that part of my brain even works, to be that bored and that still. And the stuff that was pouring out onto the pages as I was journaling, this was the only thing to do. It was just one of the most incredible experiences. And I remember writing, and the sun was starting to go down. And I remember I got to a point of journaling. I remember the last thing I wrote, I said, that’s it. That’s literally all the thoughts I have. Like, everything that was in my head was out on the page, and I was exhausted, and I just crashed into my tent.

And then I woke up the next day and I was immediately. I hope I didn’t miss the sunrise, because I knew how beautiful the scenery was. So, I zipped open the tent and I saw the sky was just starting to turn orange. And I ran up the hill and I just sat there. I was back naked because there was no one around. I was the most freak that I ever felt in my life. I’m like, there’s literally no one for miles. So, I sat there and just watched the sunrise and just sat with myself. I feel so connected to Ecuador from that experience. But what I really, really loved was that mountain climb. I mean, when I say love, I mean actually hated it. It was the hardest thing I’ve ever done in my life.

Once you get upside glacier and you’re up near the top of that volcano, every single step feels like you’re running a marathon. And that was 20,000ft. I remember just thinking, this is destroying me, and this is the hardest thing I’ve ever done. And the big lesson I learned from that is if you really push yourself to do incredibly hard things, you get a piece of identity change in. You start to think I’m someone who does hard things. So, climbing Mount Cotopaxi, sitting by myself in the middle of the Andes and the ring of volcanoes by myself for 24 hours, that was a trip I’ll never forget. And I’ll always love Ecuador.

Matt Bowles: Man, I relate to that so much. It was about two years ago when I summited Mount Kilimanjaro in Tanzania, which, exactly like you just described, was for sure the most difficult thing that I have ever done. The tallest freestanding mountain in the world. And it was way beyond the normal type of hike or thing that I would do. I totally agree with the impact of having achieved something like that and what that tells you then about yourself that you can achieve, I think, in other areas. The other thing I want to just ask if you can reflect on, though, is the significance or the impact of intentionally creating those and juxtaposing those experiences of immersion in nature and stillness with the entrepreneurial hustle and grind and urban big city life that you and I both love and are immersed in. And what is the importance of carving out and creating those types of experiences to be with yourself and to be with nature?

Dan Demsky: I think that if you never allow yourself to have that stillness, you never really get into the depths of what you really think and feel about things, right? After that trip, I decided at least once a year, I’m going to go and do a couple day, no technology breakaway, where it’s just for my thoughts. And I did it in the summer. I had this, it’s a glamping tent. So, it wasn’t as quite as roughing it. It wasn’t in the middle of nowhere. It was in Ontario, where I’m from, but it was out in the woods and there was this little dome. And I was thinking, maybe I’ll go with some friends or whatever. I booked it in advance because I saw a blog about it. It looked cool.

Maybe this will be a fun place to go, barbecue, hang out with friends. But I had it booked and I said, no, I’m going to go. I’m going to drive there, I’m going to leave my phone in the glove box, hike into the woods where the dome is and be by myself. I have a book to do, some notes, and I spent two more days doing the same thing was in the middle of nowhere in Ecuador. I was just in the woods in a glamping tent in Ontario, but I was by myself.

And once you get past the initial boredom, you really, really start to have time and space to think about things in a different way. And I think that’s one of the greatest things that you can give yourself, especially as an entrepreneur, is to reflect on your own life, on your business, have time and space to think about things and not be distracted by all the tasks that you set for yourself, by the things that pop into your phone in your email box. It’s not even close to comparing the thinking I do in those situations versus the thing I do on a regular workday. So, it’s a gift. It’s a gift. I come back rejuvenated with the best thought, the best energy, and the most clarity on what my purpose is for my life and my work.

Matt Bowles: Well, I also want to talk a little bit more about your entrepreneurial trajectory and your entrepreneurial experiences before Unbound Merino. So, I’m wondering if you can continue to take us on this journey. The business you described you had at the time in Toronto. And as you’re continuing to do these trips, how also are you starting to think about travel and starting to move in a location, independent business direction?

Dan Demsky: I’ve always just found opportunities. And my entrepreneurial journey started when I was going to see fish concerts with my best friend, business partner. He’s a very talented guy. He’s talented at everything, including art. So, when I realized at a young age that he can paint and draw pictures really nicely, I thought, why don’t you draw the bands that we’re going to go see? We’ll find a good print shop. We’ll make prints and posters of these bands, and we’ll travel around, and we’ll sell the posters, and we’ll make money, and we’ll go from one show to the next. And what we realized very early on was we divide and conquer and sell these posters or T shirts or whatever it is that we’d make.

At the end of the concert, we’d meet up and it’s like, how many do you sell that? I’d be so excited because I made three or four hundred dollars. And he’d say, I sold none, man. And like, you’re kidding me. How did you sell none? This was printing money for me. I’m a kid. 400 bucks, you make a on $5 of cost of goods. I’m like, we’re literally printing money here. He could sell them. And I think that was the awakening where I’m like, I’m selling what this guy makes, but he can’t sell it. I mean, this is a good deal we have here. I’m happy to sell them. You just keep making them.

So, I started being the director of saying, okay, well now you got to paint Frank Zappa and you got to paint this band. You got to be in that band. And we go around, and we make this money. And that opened the world to us. We started seeing all these shows. And my other best friend, he was a film major, and he got a $5,000 grant to make a mini documentary, which he spent on a camera and some software. And the second that happened, I’m like, okay, well we need to get some gigs now. So, I go on Craigslist, and I start looking for video gigs.

And we always really put our heart into the work. And I think that is the key of why things have worked for us. We were making posters. It was like, let’s just make a really unique collection of concert art that’s different from what anyone else is making. And let’s sell them at these shows. And we started doing videos, said, let’s just work our ass off. We’re getting paid 300 to do this thing. And we’d spend a week nonstop. So, if you actually count how much money we were making, if you boil it down to the hourly rate, we were probably making a dollar an hour or something. We were making no money, but we did a really good job and wowed people, and they loved working with us, and we cared. So, they started telling their friends about us.

And then we were doing these videos in my mom’s basement. And we had one project and the next and the next and the next and the next thing you know, there were a few people in my mom’s basement, and we had these employees. It was never intended to become a business. It just sorts of started happening. And one of our clients, a small AV company, he had big brand clients. And he said, hey, if I get you a deal with one of these brands, why don’t you just give me a finder’s fee and I’ll get you way better contracts than you’re doing right now. We’re like, sure.

So, he brought us into GE, and we pitched them, and we were in a real business at the time, and they wanted us to do this video for them. And they said, okay, well, we’ll pay you. We could do $3,800 for this project. Now, remember, we’re only charging people two, three hundred dollars for a project, big time. We’re just these freelance kids. And we were like, three or 800 sounds fair. Yeah, we’ll do it. We were pretending like that was normal to us, but to us at the time, that was enormous money, especially considering this was literally the easiest project we have ever come ever been given. It took us an hour and a half to do.

So, we did this project, which took an hour and a half. And I remember sitting there with my business partner and saying, we can’t possibly deliver this to them right now. It’s going to look too easy. We need to sit on this for a few days. So, it looks like we had to work harder than this. But at that moment, we’re like, okay, if these brands are paying this kind of money for that kind of work, we got to go after brands. And that’s when we created a website, tried to become proper, and we went after brands. And I learned everything I needed to learn about sales.

Just like I started with the concert posters that you’re the film major, you’re going to make the stuff, I’m going to sell the stuff. I read every sales book under the sun, and we just started beating down the doors of corporations. So, we started with all these little companies. By the next year, our client base went from the students from the College and the AV company and the little dry cleaners to GE and Fujifilm and MasterCard and Coca Cola. It just grew from there. And these brands loved us because we brought a young energy and an understanding of how the digital landscape was going to change how you do video production.

So, we were in my mom’s basement one year and two years later. We had this big downtown studio and 18 employees, and it just took off. And it was all on the back of the fact that we cared so much and we grinded so hard and we’re always trying to get better, and we really cared. So, the product we were selling was really good. And I think that’s the core of what’s always worked.

Matt Bowles: So, can you then talk about what happened with that business? Why did you transition away from that business and what did you take with you to your next entrepreneurial venture?

Dan Demsky: So that whole buildup to having the big downtown studio and all the brands was so fun and so exciting. But once we got there, then it became like a whole different thing. We had 18 mouths to feed and it became this really challenging sales operation. And the hard thing for me was it started to infringe on my freedom. I fell in love with travel. So, I did this Japan trip I told you about early on and I had this hunger for travel, so I started doing these other trips. I did Costa Rica, and I told you Czech Republic and Berlin. And I was the only one who knew how to sell this stuff.

And I think I took that for granted. I was always so excited, like, you make it, I’ll sell it. And I was great at doing the song on the dance in the boardroom and doing our little presentation, making that spontaneous joke feel spontaneous even though it wasn’t. And I was good at it. But what I wasn’t good, I was finding other people who could do it like me. I could never find other salespeople. So, I started feeling like a prisoner in the business, which was really problematic for me. And something I noticed that when I went on these trips, I’d come back and no one was pitching, no one was at the top of the funnel in the boardroom while I was gone.

So, I find like we were borderline having cash flow issues four or five months later because we didn’t fill the pipe while I was gone for three weeks. There was like three weeks of literally no business being drummed up. So, I always felt like I was hunting every day, and I was working these 16-hour days. And I remember going to a conference and meeting this guy who owned this agency that we really looked up to and he was way further along. He had 50 people at his agency, and I remember just feeling when I actually talked to him about the business. This guy’s in the same position I’m in, just bigger. Do you think he was like, oh, everything’s so wonderful for him and everything’s so great? No, he’s grinding. He has to work all the time.

Meanwhile, I had these friends that were starting these e commerce businesses, and they were literally making money while they slept. And that was just a little seed in my head. I’m like, I wish I was selling a product and not a service. It was just in the back of my head, and I was getting more and more tired every single year, just hunting for business. And as I’m starting to travel more, I’m feeling like I have no freedom. I’m stuck here. And it was starting to weigh on me. So, I went on this pursuit to try to figure out what’s the next business. And it would be once every one to two weeks, I get together with my best buddies who I worked with in my business, and we’d come up with ideas of, like, what’s the next thing? All we care about is it’s a product that you sell online to customers, not clients.

We don’t want big clients that are worth 30% of our revenue who we have to bend over backwards for all the time, and they make us miserable. We just want customers. I don’t mind selling something for 200 bucks, and if someone doesn’t love it, saying, I’m sorry, here’s a full refund and you can keep it. Not going to ruin my life. But we couldn’t do that in my other business. So literally, for almost two years, we sat there with a chalkboard or a whiteboard or a scrap piece of paper, just coming up with ideas for what could be the next business.

And Unbound came as an idea when I felt like I had a need for it myself because I started doing world travel and traveling with just a carry on. I was trying to figure out, how do you do that and how do you do it right? And I came across a Reddit post where someone said, if you want to travel, just to carry on, pack Merino wool Tshirts because they’re antibacterial and they’re odor resistant so you can pack less stuff. I said, perfect, I love it. So, I went to go look for Merino wool T shirts, and I found a few. And while I loved the fabric, I couldn’t find stuff that I felt looked nice when you went out, I wanted to go to a cocktail bar. I wasn’t just going on a canoe trip or going hiking. And all the clothing that I was finding, Merina wool brands, was outdoor stuff, not stuff you can dress up a little bit. And I was thinking, why is no brand making stuff that looks nice? It fits nice.

So, you can go out for a nice cocktail at night, but also wear it on the hike and have the same shirt with the versatility to do both. And I thought, oh, my God, I’m looking for a business to start. But the challenge was, I had another business. I didn’t have any extra capital. I didn’t have any extra energy and have the time. All I had was the idea. So, I pitched my two business partners, now business partners, and said, here’s the idea. I think we should do a crowdfunding campaign. And I say crowdfunding campaign, because if it doesn’t work, we scratch the itch. We tried it. We could walk away. If it does, they pay for all the inventory, and we can start this thing. They’re like, sure, let’s give it a go.

So, on the sidelines of my other business for a year and a half, we put together this crowdfunding campaign, and we put our all into it. I read everything there was to read about starting a crowdfunding campaign. I looked at every crowdfunding campaign that’s successful and tried to reverse engineers what made this thing work. A year and a half we did everything from sourcing the product and manufacturing the prototypes to putting together a brand to doing the video to doing all that stuff. And that was it. It was like, fourth quarter, five seconds left, fourth down, this is it. I swear to you, if it doesn’t work, I said, I’m going to go apply for a job. I don’t even have a resume. I don’t have it in me to do this other business anymore. And we tried to sell $30,000 of pre orders in the first month, and we ended up getting close to $400,000.

Matt Bowles: Wow.

Dan Demsky: And that’s where I was like, there’s a lot of people out there like me that want this stuff. I left my other business. I gave it to my business partner. I said, I need to pursue this thing. And for two years, I grinded this thing out. I paid myself 12,000 bucks. That was as much money as I made in a year. So, I had a salary in my other business before, and now I’m going broke. There was in this second where I doubted it. I was like, I know this thing’s going to work. I know what we’re doing. People want it. I want it. I’m making it for me. And we are just grinded it out and it just kept growing.

Matt Bowles: That’s amazing. Well, as you know, I am a full time itinerant digital nomad. I travel the world with carry-on luggage only, and at least 90% of my wardrobe is Merino wool. For people that are not familiar or not intimately familiar with Merino wool, can you start by breaking down the remarkable travel conducive properties to merino wool as well as the sustainability dynamic? I mean, all of the amazing things about merino wool for people that are new to this. Why is Merino wool so fundamentally different from other fabrics?

Dan Demsky: Well, it’s known as nature’s miracle fabric. And it’s antibacterial and odor resistant and wrinkle resistant and temperature regulating naturally. It’s not because there’s a chemical like tech-wear or athleisure stuff that’s made synthetically. Our t-shirts are a hundred percent Merino wool. And the fibers of merino wool, which are super fine, have a coating on them called lanolin. And this is the Merino sheep’s defense against the elements.

So, it keeps them cool when it’s hot and insulates and when it’s cold. And because it has this coating on it, moisture wicks from it. It never absorbs. And the reason why your other clothes smell if you sweat into them is because the moisture absorbs into the fabric and it becomes a breeding ground for bacteria. And the bacteria is what smells. Nothing absorbs into merino wool. It just evaporates. Like when you wear jeans, people wear jeans and they go out, they put the jeans back on their shelf and they wear them again.

And the only time people usually wash their jeans is either if they actually get dirty, like you spilled something on them, or it’s been enough time, you know, you want to tighten them up a little bit or you feel like you haven’t washed them in a while. It feels like a paradigm shift for a lot of people when they realize there are T-shirts that you do the same. It doesn’t smell; it doesn’t retain bacteria. Because of those natural properties, if you’re traveling for a few weeks, instead of packing 14 T shirts and having to stuff them into laundry bags and find a laundromat, you could just re-wear the shirt, hang it up to air dry. If you sweat through it, it will never smell. We’ve tested these to the limits. Of course you don’t want to get it dirty, and if it gets dirty, you wash it. But it allows people to have the freedom to have less stuff, which is just a way more free way to travel.

Now. Everything I do in my life is about freedom. I want to have the freedom to make the choices I want. That’s why my business is remote. I want to be able to work from wherever I want. I want to be able to travel light. We’re called Unbound because that’s what the company really stands for. It’s not just in terms of the product we provide, how it gives the customer the freedom to pack light and travel light. It’s right at the core of how you run and operate the whole business.

And that’s just the amazing thing about Merino wool for travel. I mean, you get it like you are doing the same. You just need less stuff and you’re just free. You’re not always trying to figure out, like how to pack your dirty stuff at check your luggage, worry that your bag is going to get lost or stolen. You just have your carry on. It doesn’t matter where you’re going. You’d be going to Asia, or you could be going backpacking across Europe, or you can be going to work remote from another city for many months.

I’ve done it all. It’s always of the carry-on. It’s always light. I always feel ready to go out for that nice dinner or to go for that walk or to go to the beach. I have everything I need, and it’s really freeing. And I think our brand has taken that angle. When we didn’t invent merino wool, the sheep invented it. But the positioning that we have has helped a lot of people figure out what you figured out, which is you could do this differently. You could pack light and feel more free. We always say pack less, experience more. And that’s really what we stand for.

Matt Bowles: Well, I think the other thing as well, for people that have never worn Merino wool and they just hear about it, when a lot of people hear the word wool, they think itchy, right? They think what they think of, like a traditional wool sweater or something like that. And one of the amazing things about Merino wool when you start wearing the clothes is how incredibly comfortable and expressly non itchy it is. And so, then you combine the comfort level with all of these remarkable travel properties. And it’s amazing, when I talk to people about it, they’ll be like, oh, these merino wool shirts are more expensive. Is it really worth it to spend $100 on a T-shirt, having never done that before? And I look at them and I say, when you spend $100 on this T shirt, you will eventually think it is the best hundred dollars that you have spent. And sure enough, they char try it. And they came back to me. They’re like, you were right about that merino wool T shirt.

Dan Demsky: Well, I remember buying my first Merino wool T shirt. It was a backpacker Outfitter Europe trip outfitter store. And I remember it was 95. I was holding it up, and I said to the store clerk, I’m like, I’ve never spent $95 on a T for my life. And he said, yeah, I get it. But this shirt replaces 10 of your other shirts. And all of a sudden, I just saw the value. I’m like, okay. I think that helped push me over the edge because I was trying to justify the purchase as I was trying to pack lights. And that gave me the rationale to say, okay, I get it. So, I bought it, and it performed as promised. I love the fabric. Again, I didn’t love the way it looked. I didn’t feel like I’d gone out to a cocktail bar with it. But I was like, wow, this really is amazing. And that’s how I rationalized my first purchase as a customer.

Matt Bowles: Well, I want to ask if you can talk a little bit more about this crowdfunding campaign. And I’m curious if you can give us a little bit more detail about specifically how you identified the gaps in the Merino wool clothing market, how you positioned Unbound Merino, especially with that initial offering, to be fundamentally distinct and create and test this minimum viable product that you were coming into the Merino wool clothing marketplace. How did you position it?

Dan Demsky: Well, I explained to you my thinking for why I was looking for Merino Wool. It was just scratching my own itch. Well, there’s two things. If you went to any merino wool brand I was seeing at the time, any that I could find, it was really an outdoors brand. It was either a great base layer for if you’re going skiing or snowboarding, or it was a T shirt for your hike. Sometimes it was an activewear thing that was a little rare, but people weren’t positioning it for the kind of travel I was doing. So, it wasn’t this overly complicated thing where I was trying to, like, reframe something.

I just wanted this for me, and I was willing for this not to work because I was thinking, this is going to be win, win if I do this crowdfunding campaign that’s going to involve me making the shirt that I want to exist, which I can’t find with the right drape, with the right fit, that looks good with a nice pair of pants and nice watch or whatever. So, I could dress it up, dress it down. And I’m going to have to manufacture this. And if it works, I have my dream business. If it doesn’t, I’ll have a box of prototypes that I went and made, and I’ll wear those shirts out until they’re done. And I’d be happy with that box of shirts.

So, I think when thinking of a business that you may want to start, I think just looking for those things that you just see don’t exist, and it’s wild. Like you think everything should be thought of it’s not true. People think of ideas all the time, but rarely do they go and actually try to execute on them. And in this case, there was many merino wool brands and great ones, but they weren’t speaking to me. They were speaking to the outdoors person. I didn’t care about the hike as much as I cared about the cocktail bar at the time.

So, they’ll just do it for me. I was just doing this for me. And they say one of the great exercises in marketing is to have a customer persona where you say, this is Jenny, and Jenny’s 35, and she makes this much money, and these are her interests. And you make the product for Jenny. I was making the product for me. And that made things very easy. And I think we go through life wishing, oh, I wish there was a thing that made my toaster work better, like just these random ideas we have. Sometimes those ideas are worth pursuing. So, for me, it was just like, I want this thing to exist, and I’m going to go entirely on that, and I’m going to make it for me. I’m the customer persona.  And that was the whole premise of the brand. It was just men’s stuff to start. I was making stuff for me. I was the bullseye target market.

Matt Bowles: All right, we’re going to pause here and call that the end of part one. If you are interested in checking out some Unbound Merino apparel, Dan has offered a special discount to Maverick Show listeners. You can go to themaverickshow.com/unbound there you’re going to be able to see all of the Unbound Merino apparel for both men and women. Whether you want pants, T shirts, collared shirts, or hoodies. Both lines for men and women are all there; themaverickshow.com/unbound and then at checkout, just enter the code Maverick and you will get 10% off of your purchase. I’m also going to link that up in the show notes along with everything else that we have discussed on this episode so you can find it all in one place themaverickshow.com and then just go to the show notes for this episode. And be sure to tune in to the next episode where Dan takes us behind the scenes and explains how he was able to scale Unbound Merino to a $40 million a year business while traveling the world as a full-time digital nomad. You are not going to want to miss that. So, tune in to the next episode to hear the conclusion of my interview with Dan Demsky. Good night, everybody.