How a Clothing Brand Made This Man Travel the World for Years

Nomad Ryan O'Connor

My name is Ryan O’Connor and I’m the primary owner of, an e-commerce clothing brand that was started on my first trip to Thailand in 2014. Before that, I worked in SEO first at an agency and then freelance while I traveled. I’m currently in Ireland after spending most of the summer in Budapest.

For hobbies, I love music and used to play guitar in bands. One of the hardest thing about the nomadic lifestyle is not having an electric guitar with me although if I’m staying somewhere longer term, I usually pick up a cheap acoustic guitar then give it away when I leave. I also like martial arts, grew up doing judo and now I’m trying to get more into kickboxing when I’m in a good city for it.

After four years of travel, I don’t like guided tours or any place thousands of other tourists are going to go with selfie sticks although I will of course make exceptions for places like Angkor Wat in Cambodia and Christ the Redeemer in Brazil. I’m definitely a city person so I love walking around or jumping on a metro and exploring a city. Ducking into a cafe here or a shop there as well as meeting local friends who will tell you about their home is the way I like to do it.

As far as personality goes I think i’m a pretty even split between extrovert & introvert and I credit that to my Dad being a pure extrovert and my Mom as an introvert so I seemed to get 50% from each side. I’ve done music, public speaking and traveled solo so I’m used to getting out of my comfort zone and putting myself out there but I also sometimes need time to recharge. I’d like to think I’m quite friendly and approachable and definitely not serious at all.

Nomad Ryan O'Connor

How and why did you become a nomad?

I hit my four-year mark of being a nomad on August 14th so I’ve been doing quite a bit of reflection lately. My story is that basically I wanted to be a rock star and when that dream ended I still knew I wanted to travel and see the world so I had to find a path to do it. I went to school for marketing but I learned a lot from hustling shows and promoting my band online. I also dabbled in online poker and I remember one day looking at the bottom of a site and seeing a page about affiliates and that sent me down a path to reading about affiliate marketing, which was my first foray into the world of online business. I decided I didn’t know enough so I got a regular job in SEO, which I think is highly underrated approach. Getting a job where they pay you to learn the business vs. trying to bootstrap it with no experience can be very valuable for you long term.

Like many people, the 4-hour work week was a big influence and inspiration to me and after that I became a religious listener of the Tropical MBA podcast and would keep photos of Bali as my desktop background as I started to plot my getaway.

Why is having a nomadic life important for you?

I think being a nomad is an unprecedented opportunity and privilege unavailable to the mass majority of people throughout history. I love reading about history and one of the things that has stood out to me lately is that I’ve probably seen more of the world or at least been to more different corners than many of the great conquerors and explorers of old.

I plan on continuing to build my business and hope to be quite successful but going to Carnival in Brazil with good friends, meeting family members in Ireland, doing karaoke with Vietnamese businessmen in Saigon and countless other experiences I have are worth way more to me than accumulating stuff.

Being a nomad has just opened my mind to the rest of the world and I’ve met so many great people along the way in there hometowns and other nomads and travelers as well.

Nomad Ryan O'Connor

What have been the best and most difficult parts of being a nomad?

Easily the people and relationships you build along the way. I also think being a nomad in the way I do it (I like to stay somewhere a month at a bare minimum) allows you to dive into the local life and culture in a way that someone on a 7-day vacation who has site seeing tours booked every day never could. Taking part in the local culture of each city really bonds you to that area vs. being on a bus with 50 other tourists with cameras.

The most difficult part of being a nomad is definitely the instability and how hard it can be to get into a regular routine. You’re always off in a new place and often you don’t speak the language so you have to push yourself out of your comfort zone to get setup. I also think the temptation to always be going out exploring, hanging with friends or partying can be tough as well. What if I’m never back in Lima, Peru or Reykjavik Iceland or wherever I’ve been at the moment? That uncertainty makes it easier to prioritize those experiences vs. someone who can have a more strict routine at home.

I’ve had a few times when I’ve been lonely but I’ve adjusted pretty quickly and now I have a great crew of friends who do what I do and we meet up at different places over the course of the year.

For instance, five of my friends I was with in Mexico earlier in the year all came to Budapest for the summer so it’s gotten to the point where I travel with my friends making things more familiar.

Nomad Ryan O'Connor

Where do you live as a nomad?

Now that I’m in my 30s, I’m not about the hostel life although I’ll occasionally do it if I’m traveling through somewhere like Iceland where it’s ridiculously expensive. I much prefer to get an apartment and stay somewhere for at least a month. AirBnb can be good but in many places the rates are overpriced so the trick is to find the local rental sites.

I don’t cook that often but sometimes I will and I’ve also signed up for meal delivery services (makes it easier to eat healthy) in some cities I’ve lived in. Usually though I just find the local little cafes & restaurants I like and go there frequently. I love Asian food so even when I’m not living in Asia, I’ll be looking for a Thai or Vietnamese restaurant.

The biggest difficulty for living is that sometimes you book a place without having visited and then the location isn’t what you thought or some of the amenities aren’t what was promised. Usually I can get over this pretty quick unless there is a problem with the WiFi that’s really the main thing I need.

Where do you usually work?

When I’m staying somewhere longer than a month, I usually join a coworking space. I like the separation of church and state of having a desk space in an office with no music playing as it allows me to zone in.

My routine varies by city and I try and take an afternoon nor two per week to explore or do something new, go to a meet up, etc. but usually during the week, I’m trying to get to the gym in the morning, coworking space in the afternoon until early evening then dinner with friends, go out or read at home.

Nomad Ryan O'Connor

How do you build a social life as a nomad?

I think the best way to do this if you’re just starting out is to go to one of the nomad hot spots like Chiang Mai, Saigon or Medellin where it’s easy to meet other people living this lifestyle. I spent a good chunk of 2015 and 2016 in Saigon because it’s where I most connected with the community.

When I think back to my first year or so as a nomad I was mostly going completely solo and it was a challenge and more isolating. I’d meet some cool people but it was more temporary because most weren’t doing the same thing I was. I didn’t know exactly how to connect with the community.

Now, I’m at the point where my friend group is other digital nomads/online entrepreneurs and we plan things together. It’s not everyone at the same time but there’s a tight knit group where we discuss where we’re heading next or what we’re planning for the year. To have a fulfilling social life and feel normal, I think you have to have a core group of friends who do the same thing if you’re going to make it long term. Either that or you need to find a city you really love that you spend part of every year in. I don’t think most people can go on forever being completely nomadic and hopping from place to place and starting from scratch with their social circle every time.

The biggest thing you need to do is just put yourself out there and go to meetups, talk to local people on a night out and get over any reservations you may have.

How do you finance your nomadic life?

I run One Tribe Apparel and have one consulting client. My budget really varies on where I am and how my business is doing but I’ve never had an issue in Asia, Latin America or Europe. My biggest expenses are rent, food, flights and going out.

Nomad Ryan O'Connor

What kind of gear do you bring with you, and how do you carry and organize your things?

I’m pretty simple in this regard. I have a laptop, a a Roost laptop stand, a wireless keyboard, and portable speaker as my main gear and then I have a kindle and my phone. Most everything else I have is clothes and a jump rope. When I’m somewhere longer, I buy an acoustic guitar but I’d like to figure out how to travel with an electric guitar.

I have some friends who can live off of a carry on bag but I have a suitcase that usually weighs in at 20 kilos or so. I’m 6′ 3″ (191 cm) and wear size 13 shoes (48.5 cm), which creates extra difficulties when living in some places, particularly Asia. This means I usually bring 3 or 4 pairs of shoes with me and a good amount of clothes because I can’t just go out and buy what I need at the mall.

I have one big Samsonite Hypertech Lite 30″ Spinner suitcase and I have one Lowe Alpine Air Zone Trail 35 Backpack that I picked up a few years ago in Ireland that’s good for hiking and also can fit enough for weekend trips. These bags are definitely enough for me. I’d like to downsize a little bit as I probably bring too much clothes with me but I like options and I hate laundry.

I roll things up to save space but I’m not that careful otherwise. As for bag recommendations, I really like the look of the Minaal bags and will probably get their bigger bag next time I need a new one.

What has been your best gear purchase below $100?

100% it’s been my kindle, which I think I got on sale for $50.00. Since I work on my laptop and I’m online all the time, I used to carry 6 or 7 books with me (which once or twice but my bag over the weight limit) because I wanted to keep the feel of real paper in my hand. I also had a tradition where I’d give a book away after I was finished to someone I thought who would like it. While I liked the feeling of passing the books on, as soon as I got my kindle, it was a game changer.

It’s just so nice to have a library of books that you can refer back to and keep many with you at a time in such a compact little device. I usually have three books going at one time. One business book I read for 20 to 30 minutes in the morning, one history or sociology related and one fiction that I read at night before sleep.

Nomad Ryan O'Connor

What is your best advice for new nomads?

Avoid shiny object syndrome and chasing a million new projects. Focus in on something you think has potential and see it through for a certain amount of time. Take action with your work and do more than you consume in information and you’ll be sure to get better along the way.

Honestly, I find this question difficult because some people will never pull the trigger on pursuing this lifestyle and just like to daydream about it as a little escapism on their lunch break.

I used to really try and push people to go out and travel the world and work online but I don’t anymore. It’s challenging and so if you’re going to be able to keep doing it then you need to have the confidence in yourself to pull the trigger to get started.

Nomad Ryan O'Connor
Elephant Nature Park – Beautiful Moment.

What will the future bring?

2017 has been a really busy travel year for me, too much for the amount of work I need to get done. I started off in Medellin, Colombia in January then spent February in Peru and Brazil. March – June, I bounced around Mexico and then I did a two-week long trip home through the US before heading to Iceland. After a few days in Iceland, I reached Budapest, Hungary for the summer. Now I’m in Ireland on a family trip traveling around to a new town every few days.

The rest of the year is going to be spent grinding and hanging out in Saigon, Vietnam, which I consider my home away from home at this point. Q4 is really important for e-commerce so I need to get focused and into a good routine for the next few months.

I’ve had a few new project ideas stirring around my head for the past year but I’m big on focus and for now I’m all in on my e-commerce brand One Tribe Apparel where we’ve greatly expanded our line of boho clothing. Aside from that, I’m making a bigger effort to document my travels on Instagram at @RadPirateship

My big plan for 2018 is to really explore eastern Europe starting in the spring. I want to hit Poland, Estonia, Croatia, Serbia, Ukraine, Belarus and more and then pick my favorite and stay for a few months over the summer.

As far as travel gear goes, I’ve got my eye on one of the flying cars from Larry Page’s new company Kitty Hawk. Once we have jet packs you won’t catch me anywhere for long I’ll just be flying around.

Follow Ryan O’Connor on his website and Instagram

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