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This week on the podcast we are excited to be talking with Dylan Magaster about adventure and creativity. Dylan is one of the most interesting guests we’ve talked to in our years of podcasting and joins the show from his sale boat in Tunisia.

After reaching a feeling of discontent in day-to-day life at home Dylan decided that he wanted to create a career on YouTube. A risky idea for sure, but one that he was committed to. So he set off on adventures across the US, down to South America, and then back to the US making videos along the way. 

After years of hard work and dedication, Dylan found traction focusing on interesting homes and hasn’t looked back since. 

In this episode:

• Where Dylan is right now and what it is like living on a sailboat out of the water
• How Dylan got started traveling 
• Making the decision to travel to South America to work on travel vlogs
• Taking a risk to go into debt while working on travel vlogging
• How do you balance work and travel when travel is work? 
• Making your life an art project
• Why and how Dylan starting making videos about unique home spaces 
• Chancing projects without a ton of support
• Why give up van life to go sailboating 
• Walking through the process of finding a boat, getting going, and then working as a content creator while sailing
• What are the most challenging things about living on a sailboat
• Dylan’s experience of the pandemic

• Check out Dylan’s YouTube Channel and FLORB
• Listen now

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If you would to get access to the past and future episodes of our nomad series as a World Wanderers Insider, head on over to Patreon.com/theworldwanderers. Thank you so much for your continued support!

Where Dylan is right now and what it is like living on a sailboat

Dylan opened up about how time is passing in Tunisia, Africa, located in a monastery marina, and his process of waiting to put his boat back in the water after doing some fixing on it. 

“I’m in a monastery on a sailboat. I have lived on it for two years and have been in Tunisia, Africa, for almost four months. Time is weird right now because the days feel longer than the weeks. It seems the last couple of months haven’t been particularly glamorous because we had been living on land, on the boat. We had pulled the boat out of the water, so we did different repairs on the boat. I ran aground in Italy and damaged the boat’s bottom, and I had to do the fiberglass work to fix that. That took ages, now mainly just waiting for the boat to dry. So yeah, for the vast majority of the time here in Tunisia, we’ve been out of the water, which has not been ideal, but it’s not the first time I’ve done it. So, not too bad. “ -Dylan.

Dylan had the pleasure to meet the friendly community of sailors from France, Canada, and even New Zealand, and they hung out and did some jam sessions.

“What’s nice about this monastery marina is that there’s a nice community of sailors, a bunch of French folks, some Canadians, some New Zealand Kiwis. And so we’ve had a few get-togethers and jam sessions, and it’s turned into an actual community. Now, like the other day, when I put the boat in the water, two guys, Andy from Canada and Tony from California, both came and helped. Jackson and I got the boat back in the water and got it put back together. They’re both sailors. So it felt like a legitimate community. I’ve been hanging out with these guys for months now. So all things have been pretty nice.” -Dylan.

How Dylan got started traveling 

Dylan admitted that he was not a seasoned traveler when growing up, as he had just done a bit of traveling here and there. As we talked, he shared a memory of when he turned 11 in Holland, which was the most significant trip he had done as a child. And it was a family occasion to cross the ocean because of a sports league his sister participated in.  

“We did a bit of traveling, growing up, nothing too insane, but like a good amount. I turned 11 In Holland, and so that was like, that was like the biggest trip that I had done when I was younger. That was the only time I had crossed the ocean. And that was because my sister was in a sports league where they did one season in Europe for some foundation. I think it was a HeartToHeart or something like that. And other than that, it was a lot of just around America, different road trips and whatnot. I also went to Florida a couple of times.” – Dylan.

We listened as he continued on telling his story of growing up in a church during his high school years and going on a mission to Honduras. It is something he dearly remembers.

“I grew up in the church, and so when I was in high school, I made three different trips down to Honduras for mission work. That was really, really great, and I liked that a lot. And, so that was kind of the extent of my traveling experience. When I decided I wanted to start traveling, I bought a Prius because I was like, cheap gas, mileage road trips, this will be legit. Also, it’s big enough that I can actually sleep in the back of it, which is cool.” – Dylan

He began doing road trips right away, starting from Kansas City to New Mexico – he also visited Seattle, but he felt that traveling is somehow tiring and requires so much driving. So he decided to go to New York and live with his dad for a while. 

“And so I bought that, and I started taking road trips, like once a month, as much as I could. The first one was to New Mexico from Kansas City. And then, I made a six-week road trip around Western America. So I drove from Kansas City to LA up to Seattle and back in six weeks, which was crazy, you know, not being a seasoned traveler at the time. I was like, yeah, this is totally doable. And then, about halfway through, I was like, wow, this is a lot of driving. So I did that and then made a trip to New York City. Then I moved to New York City for a couple of months and then moved back in with my dad and flew out to America after that and started backpacking full time. So I had a bit of a cushion experience where it was like, go out, come back, go out, come back, and then I went full-on, out on my own.” – Dylan.

Making the decision to travel to South America to work on travel vlogs

Dylan’s decision to travel to South America was a leap of faith, and in his words, you need courage and stupidity at the same time to make big moves in your life. He wanted to be a pastor, but then he realized he was into cooking. He went to community college for cooking, but ended up dropping that and decided to build a career with YouTube. It seems like he was purposely looking for what is genuinely his calling and managed to end up in the exact right place.

“Yeah, it was a leap of faith, that is probably the right word. I’ve got this idea of courage, and it’s hard to tell the difference between courage and stupidity sometimes because you kind of has to have a bit of both. If you know everything that’s going to happen, you probably won’t do it. So, you need to have that ignorance to make that step. And so, I guess leap of faith is probably the right way to describe it, but I dropped out of community college. I was going to community college to be a cook, to be a chef. And before that, I thought I wanted to be a pastor. I realized that I really liked cooking. And so I was like, yeah, I’ll just see what happens if I do this career. I was working in a country club, and I was like, not for me. So then I started making YouTube videos, and I was like, this is what I’m going to do. I’m going to figure out how to make YouTube work.” – Dylan.

Choosing a YouTube career takes a strong commitment. And at first, when he started taking road trips, he moved to New York with his dad to earn some money and just work and stay at home. At 21 years old, he wasn’t happy with that.

“That was my commitment. So then I started taking those road trips and whatnot, moved to New York City, kind of went broke, moved back in with my dad, and was doing construction and home remodeling. I was living with my dad, and it was just him and I at the house that I grew up in. It was not a great situation for me. It was like; I would wake up, go to work, come home, drink and watch comedy. That was basically my routine. Well, I also went to the gym a lot. The gym has always been my heaven. So that was the routine I was in. I was like, this is not what I should be doing at 21 years old; this is not a good path.”

Working almost two months for his father, he earned enough money to start buying cameras and stuff like that for his YouTube career. He was excited to embark on a career path that could give him the freedom to travel a lot and see the world.

“And so I saved up like a thousand bucks over two months or something working for my father. And the years before that, I worked with credit cards, so I would buy cameras and stuff like that to get points. The commitment I made to myself was that I was going to make a YouTube career basically. And one of the reasons I did that, the main reason was that I figured that was the job. The career path I could take would allow me the most freedom to do whatever I wanted and create the life I wanted to live. And I knew that I wanted to do a lot of traveling. A lot of it was influenced by the internet, seeing these different, beautiful locations and being like, yes, I need to see this planet.” – Dylan.

Taking a risk to go into debt while working on travel vlogging

He explained his journey to Paraguay and how he ended up in 17 thousand dollars in debt while traveling and managing his business, which he paid off at the end because he lived in a van, so he didn’t have as many expenses.

“And, when I bought the plane ticket to Paraguay, it was $17. Yeah. But, unfortunately, the visa to get into Paraguay was actually a hundred bucks. So, yeah, I had a thousand bucks on my credit card. And so I was like, I’m just going to start going and make these YouTube videos and my thought was, yeah, I’ll start making money before I run out of a thousand bucks. That’s not how it happened at all. Long story short, I ended up 17 grand in debt. I was able to pay all that off, but I basically intentionally went into credit card debt while traveling because I was also building a business while doing that. That was a pretty high-risk thing to do so I don’t advise people to do it at all. Still, once everything started working, I was able to pay that off really quickly because I was living in a van at the time when I started making money, so my expenses were low, so with any profit, I just smashed down that debt as fast as I could.” – Dylan.

How do you balance work and travel when travel is work? 

It was quite intriguing to learn about Dylan’s philosophy about life, how he sees it as both his work and life. That philosophy helps him balance things and gives him the enjoyment of life while working.

“So when people ask me about work-life balance, it’s kind of become my canned response now, like there is no balance. My work is my life, and my life is my work. And it’s super difficult to even differentiate between what is work and what is not and, I mean, if I’m doing work, it means I’m on the computer doing work. It’s like, that’s not all the work because I also do the filming. I also do scheduling, so there’s also the whole travel aspect of it.”-Dylan.

Making your life an art project

Along with his life philosophy, he also told us that he wanted to design a life that has everything harmonized together to make a beautiful art form that is enjoyable and sustainable at the same time.

“I heard a saying once that was, “everybody’s an artist and their life is their art” something like that. So I’ve kept that in mind a lot. I want to design a life and live a life in which it’s incorporated together so that it all harmonizes into some beautiful piece of art. So it’s not like I work and I don’t like that. And then I go live my life. It’s like, I want work and life to come together. What is my life basically? Like I want it all to be the same thing. But that can obviously be tricky whenever it comes to the actual technical things of working. Like the managerial things that aren’t necessarily fun, but that’s how I balance it. I just put it all together.” -Dylan.

Why and how Dylan started making videos about unique home spaces 

During one week, he squid fished for money to buy a van and built it back home in Kansas. But then he realized that he couldn’t enjoy traveling with the van as much because he had work and had to film and edit videos of tiny houses he researched along the way.

“I ended up going up to Massachusetts and working on a fishing boat and doing some squid fishing for about a week and was able to make enough money to buy a van. So, I bought a van in Maine, and then I traveled around the Northeast for a couple of months; I think they were like 60 days or something like that. Then drove back to Kansas, built it out in a month, and then headed west. When I got into the van, I thought, oh great, I’m in a van, I’ve got my rock climbing gear. I’m going to do loads of rock climbing and just explore and do all this kind of stuff. But then it was like, oh yeah, I have to work. And so I would research to find these tiny houses and vans that I’m filming. Schedule them, go film one, edit one, post one, repeat.” -Dylan.

When he was staying in the cabin of a fishing boat, he decided to make a video tour of the whole cabin, so then he realized he could do plenty of video tours of other tiny houses or vans. Because he was obsessed with tiny houses, and it was the only thing he watched on YouTube.

“When I was working on the fishing boat of captain Mike and Kelsey, I was actually staying at their house for like a month. Captain Mike had built a cabin up in Maine, in the forest, just an off-grid cabin. So, I was staying up in the cabin for like a week, and while I was there, I was like, hey, Kelsey, does your dad care if I make a video about this cabin? And she was like, no, of course, go for it. So I just did a handheld tour of it talking to the camera, and then I was like, maybe I could do tiny house tours and stuff like that.

When I was in high school in like 2012, 2011, I was obsessed with tiny houses. That was almost the only thing I watched on YouTube. And I was like, I want to build a little house. I don’t know; living in a tiny house, it’s so much better than conventional housing. It’s also way cheaper.” – Dylan.

After he filmed the cabin video, he found a guy back in Maine with a tiny house, so he filmed a documentary with his house. He got so locked in, and he finished that work so fast, which earned him a lot of new viewers and subscribers. 

So he leaned into that spark and continued doing it with Alex, a girl in her van, a video that reached around 300K views. This inspired Dylan tremendously to continue his creation.

“So when I filmed that video of Mike’s cabin, that all kind of came back to mind. And so then I found this guy who had built a tiny house when he was a teenager in Maine. So I went, and I shot a short documentary about him. And when I went to edit that video, I just got locked into it and just did like a straight-eight or nine-hour edit session and just boom. The video was pretty much done by the end of that day. And I was like, wow, that was great. I really liked shooting that, and I really enjoyed editing it. And so, as soon as I switched to posting this style of content, my views jumped three times. I was getting 1000 views a day at the time. And then it immediately jumped to 3000, and I was like, there’s something there. And then on January 1st, I posted this video about Alex, and that video started to take off way more than anything I’d ever seen. So by the end of the month, it had like 300 thousand views with all the other videos that were gaining views on the channel before that. That was my break-even point.” -Dylan.

Why give up van life to go sailing

Dylan told us how he was fed up with life in a van, the same way he was fed up living out of a backpack. He wanted something more; he wanted something bigger, so he thought about the next crazy idea!

“I was just kind of done living in a van. Like when I moved into the van, I was pretty done living out of a backpack. I’d been doing it for six months. It was like, I don’t want to do this anymore, but I’m not done traveling. And the same thing with the van. I couldn’t stand up in my van, so that was a big deal. I was like, I’m getting pretty tired of this; at about 18 months in I was like, this is kind of hard. I had a really basic setup so I needed something that would allow me to travel, but is bigger basically, like what can I have more space within, like either a bus, an RV, or I don’t know, maybe a boat. That seems cool.” -Dylan.

Walking through the process of finding a boat, getting going, and then working as a content creator while sailing

Dylan knew a sailboat guy so went to spend some time with him because he knew nothing about sailing. Also, he decided to go to Cabo San Lucas because he thought along with sailing, he would scuba dive all the time.

“I knew this guy, Eddie Landis, who built his own sailboat. His son also lives on a sailboat. So I spent some time with them, and I knew nothing about sailing. I went down to Cabo San Lucas to get scuba certified because I thought, if I’m sailing, I’m going to be scuba diving all the time. And I thought, well, it’s definitely gonna be cheaper to do it in Mexico than California. And I drove down to Mexico, which seemed like a really cool adventure.” – Dylan.

Dylan told us about a fellow with a smaller sailboat he met and asked him to teach him the art of sailing. His first sailing trip was down to San Lucas and back to California. After that, all the way to the Mediterranean and Barcelona.

“So on the way down there, I knew nothing about sailing. I met this guy named preacher man Roy, and he’s from the Ozarks. He had a tiny sailboat, a 12-foot sailboat, and he was like, I can teach you how to sail. Let’s go. And so we did one day of sailing around, and that was my first time sailing and then made it down to San Lucas. And I did a couple of days sailing with Bobby, from sailing doodles, and then drove back up to California. In April, I flew to Florida and did a five-day sailing course. And then, in April also, got on a ship to go to the Mediterranean. So it was November that I decided that that’s what I was going to do, and then, by May 6th, I moved onto the sailboat.” -Dylan.

Interestingly enough, Dylan bought the sailboat on Reddit. So when he got to Barcelona, he immediately moved onto the sailboat and learned everything about it right there, along with filming videos about tiny houses and vans.

“The way I bought my sailboat was off the internet. I found it on Reddit. So when I wanted to go sailing and when I wanted to move to the Mediterranean by sailboat, I had no idea what I needed. So we got to Barcelona and on the same day I bought the sailboat. And then, four days later on, we moved on, on May 11th. I had to learn everything about the engine, how the boat works, everything like that. And so during this whole time, we were also filming and making the sailing series, and it got to the point where it was so overwhelming… I was creating, both the alternative living spaces, the tiny house tours, van life tours, and everything like that on the floor on YouTube. And then also, we were creating the sailing videos as well.” -Dylan.

What are the most challenging things about living on a sailboat?

He explained that sailing isn’t that simple and has a lot of complicated things such as weather, knowing how the sea and wind work, and many more things.

“So it depends on what stage you’re at, if you’re just in the learning stage, the actual aspect of sailing, the setting of the sails is not very difficult. The more difficult part of sailing and operating a sailboat is the weather and dealing with that and understanding how the sea works and how the wind works. How big of a picture do I need to look at? Also, understanding what to do when the weather changes when you’re out on the water. Because if you’re just a day sailor, you just go out for say a couple of hours a day.” -Dylan.

As we approached the end of our conversation, Dylan concluded that obstacles and difficulties lead to growth in many ways.

“And each one has its obstacles and difficulties, but they make you grow in different ways” -Dylan.

Dylan’s experience of the pandemic

Dylan remembers how everything started to close down days after he arrived; within the first few days he was out of the water, everything had been closed, the borders, no more tourists, and things like that. So he patiently waited for the borders to open so he could sail to Malta and Italy next.

“It was days after he arrived when everything started to close down…Within three days of being out of the water, everything was closed. All the borders were closed, and nobody was working anymore. Then we just took it as it went. So now everything’s starting to open back up. And right now, we’re just waiting for Malta to open its borders so that we can sail to Malta. And then, from Malta, Italy is opening up its borders really soon. Greece is planning to open its borders in July.” -Dylan.

We were happy to hear that Dylan used the lockdown and pandemic as an excellent opportunity to improve his YouTube channel; he is sort of thankful for that lockdown time because it allowed him to be fully dedicated to this.

“We’ve been using this time as a great opportunity to just do tons and tons of editing and tons of work on the channels. We’ve got both channels in a really good spot and we’ve been working to figure out how to develop the second channel in a way that we really enjoy creating with it because it took us a while to figure out how to structure the videos and everything like that. We had that forced time to decompress and think and figure it out and then just do loads and loads of editing. So yeah, we’re really happy with how that’s coming out.” -Dylan.

Final Words

It was exciting to have the opportunity and speak with Dylan Magaster. A man like him epitomizes a sense of adventure and courage, as he possesses both. 

The stories he tells about his travels and nomadic lifestyle are always fascinating! His way of traveling and moving around is also pretty unique. This allows for him to maintain his nomadic lifestyle in the most interesting way.
If you want to join in on his daily travels and adventures, check out his Youtube channel and FLORB, where he shares all his experiences through his fantastic content!