How about starting an online clothing store?

One Tribe Apparel Shoot Wrap starting an online clothing store
Ryan in Thailand with his partners at the One Tribe Apparel Photo Shoot

With a bit of creativity there are so many ways you can make money while pursing a lifestyle of travel and adventure You could set up your own online business that allows you to travel and work around the world, you never know where the next opportunity or moment of inspiration will come from.

This week I’m speaking to Ryan to find out how he makes make money online and leads a digital nomad lifestyle.

So how about starting an online clothing store – an interview with Ryan O’Connor from One Tribe Apparel.

Ryan O’Connor is from Philadelphia, USA but now he is living in the mountain town of Pai, Thailand. Ryan funds his lifestyle of travel in Asia and Australia by splitting his time equally between freelance SEO consulting and running an e-commerce clothing business One Tribe Apparel. He met his two business partners in One Tribe Apparel in Pai as they run a hostel in town. Between his two businesses and his travels, Ryan also occasionally fits in a couple of posts about my travels at He describes his lifestyle as a digital nomad as; enlightening, hectic and fun

Sounds like a good lifestyle you’ve got there Ryan, what made you want to work online and travel as a digital nomad and how did you make it happen?

When I was  younger, the only thing I wanted to do was play guitar in a rock band. I basically put all my chips in that basket and gave up some big opportunities like doing semester abroad in Australia because we had gigs.  My parents instilled a love of traveling in me early and so when the band ended I knew I still wanted to go out and see the world but had to find a new vehicle to do so.

I did a lot of work promoting my band and built our first website, built a mailing list and tried to hustle on social media to get people to listen to our songs (this was the MySpace era). I would test out different messages and learned things like including someone’s name in the message greatly increased the frequency with which they’d respond or check out our band. I was laying the foundation for my career in SEO without even knowing it as many of those skills make up a big component of what I do now.

At some point I got a copy of the 4 Hour Work Week and it all clicked into place and I knew I wanted to be a digital nomad. I remember how excited I was at the time thinking of setting out on adventures but it took me 3 years of hard work to get to the point where I was able to travel and freelance at the same time. After teaching myself SEO & PPC I switched jobs from commercial real estate to digital marketing and worked at a top agency for 18 months. I’d work on affiliate sites after work and started to get freelance work as well. Eventually I pulled the trigger and went freelance full time. A few months later I booked my first trip which was a 2 month stay in Mexico.

Ryan in Ireland

So you’ve now also started an online clothing store too. Tell me more about this new e commerce venture…

The basic concept is to bring unique bohemian clothing from Asia back to North America. Right now we feature all Thai clothing but soon we’ll be adding clothing from Nepal and Bali and then expanding further from there. E-Commerce is my strength so the plan is to stay focused on growing the business online and to have a presence vending at music festivals. We don’t want to get distracted by wholesale or retail at this time.

That’s awesome, I love those pants and wear them in Asia all the time. What a great idea! So what do you like the best about life as a digital nomad?

The world is a big beautiful place and there is so much to see  and do.  I love learning about the history & culture of everywhere I travel. However, the #1 thing I like is the people you meet along the way. I have friends now from everywhere from South Africa to Norway to New Zealand. Travel mostly self selects for cool people so it’s just great getting a chance to go out there and share the travel experience with others from totally different backgrounds.

Totally agree with that! But nothings perfect right? Are there any downsides?

For me the big thing is that I miss home but I also feel a disconnect. I don’t know any other way to say it but that it’s different now when I go back. I still love all my friends but we’re heading down different paths. I’ve heard other travelers describe this feeling as well where you can’t wait to get home but as soon as you get there all you want to do is head back on the road.

I know how you feel there too! Do you have one standout highlight, achievement or a favourite destination? 

This past Sunday we had a photo shoot for One Tribe Apparel at my friends house high up in the hills of Thailand overlooking the valley. As I stood on the edge of the balcony looking at the sunset I had one of those smack me in the face moments of realization. I was surrounded by good friends in beautiful Thailand (while it’s freezing back home), having a few drinks and taking photos and video for my company. Almost exactly four years ago I remember feeling depressed and lost in the Philadelphia winter unsure of where I was heading with my life. To think of where I am now just gave me a great feeling of gratitude and accomplishment.

One Tribe Apparel Press Photo starting an online clothing store
One Tribe Apparel – Ryan’s e commerce business

And what has been the greatest challenge?

The best & worst part is the people because you meet so many friends and interesting characters and then you’re always saying goodbye. I’ve been in Pai, Thailand for two months now. A few weeks into the trip we had this amazing group form together where we all clicked and had a lot of great times going to water falls, a music festival, partying etc. One Monday almost everyone went their separate ways and when I went to the communal hangout area it was all new faces. At that moment I didn’t feel like starting over or talking to anyone but you get over it and soon meet other new awesome people.

A quick 2nd one from a business perspective is routine. I spent years trying to get out of the 9 to 5 grind but sometimes you need that structure. Renting a place and finding out it doesn’t have a desk or solid internet, taking long buses or flights between locations, etc. can really throw you off and set your work schedule back

What do you wish you had known before working remotely?

I wish I had known more about ways to find travel deals, get credit card miles, etc. I’m 18 months into traveling and just starting to learn that now. Other then that I think I was well prepared because when I worked at an SEO agency I had clients in all different time zones and knew how to make those relationships work without being face to face.

Leeds Festival England

So, what about the future? Where do you see yourself in 5 years time?

I plan on growing One Tribe Apparel into a multi million dollar brand (with the help of my partners) and that will be my first priority. If that means settling down at some point then so be it. All three founders love to travel so we plan on setting it up so we all have the ability to work remotely at least a few months per year.

When it comes to travel I still have a big to do list. I’d like to spend a lot more time in Europe as I love the history and the people but I don’t know if my current model of a few weeks or months in a new location will suit me in the long term. Ideally within a year or two I’d like to pick a more permanent home base and then travel a few months per year from there. It’s critically important for me to avoid falling into a routine of staying put too long. Traveling to a new place is like a reset button. When i’m about to head back out on the road I get that buzzed feeling that I got as a kid on Christmas and it reminds me how full of possibility this world is.

The dark hedges - Northern Ireland

Finally, and perhaps most importantly, what tips would you give for people wanting to follow in your footsteps?

1.) There’s nothing wrong with taking a job first in your digital nomad field of interest.

Whether that’s writing, photography, web design, SEO or any other job you can do while traveling. In fact I think this is often an overlooked component of setting yourself up for long term digital nomad success. You’re going to struggle competing against someone like me in SEO since I have years of experience working on campaigns with multi-million dollar e-commerce companies. Same thing with someone who is taking four years graphic design or programming experience with them.

2) Consistency is the key.

I’ve tried to help a lot of people who want my lifestyle and the majority of them quickly burn out after the initial excitement about work & travel or a new business idea fades. It’s truly a grind especially while traveling. I can’t tell you the last time I took an entire day off without doing any work. I’m always thinking about what’s next, how to improve and making sure I get something done every single day. I know how glamorous it looks or sounds to someone on a 3 week trip when I tell them I can keep traveling as long as I want with my job but it’s not always easy. I’m always missing a cool day trip or a night out because I have a client call or deadline, technical issues that arise or just need to put in a long day to catch up.

You’ve got to embrace the grind and understand that any business is a long game with highs and lows. Take the photo shoot story I told above. Although it was an amazing day it’s a tiny fraction of what I do to run my e-commerce business. For every two hour photo shoot in a cool place I’ll be spending 100 hours doing SEO, social media, fixing website problems, fielding customer service emails, talking to manufacturers and writing process documents.

One Tribe Apparel Thailand Shoot

If you’re just getting started blogging or running an affiliate website then set yourself some realistic goals and try to frame them around a consistent input of time. For instance, I think people always get themselves in trouble with goals like “write one blog post a day for 30 days”. Sometimes you’ll end up hating what you wrote or one topic will take 5x as long as another and then next thing you know you’re 5 blog posts behind. Instead, commit to writing for 30 minutes per day 5 days per week. Only publish your best stuff and realize the time invested in writing the posts you didn’t like are part of refining your style and voice.

3.) Leverage your best skills to learn new ones

I’ve had a lot of success in SEO especially when it comes to building links and the more success I had the more I tried to refine and develop my system. Then I used that success to trade ideas with other people in my industry. I’ve also exchanged SEO advice for graphic design or photo work.


Wow thanks so much Ryan for such good advice! I can really to relate to a lot of what you say and I am loving One Tribe Apparel and hope everything goes well for you!

Make sure to check out other working abroad interviews and ideas and if you are working abroad and would like to be featured and inspire others than I want to hear from you. Email me anna [at] global-gallivanting [dot] com or use the contact form.

Related posts

The truth about Voluntourism in Sri Lanka


How to become a Tour Guide


How to travel and work your way around the world



Wayne Seto May 18, 2015 at 8:01 pm

Simply, an inspiring interview. Thank you so much for posting.

Anna Phipps May 18, 2015 at 8:44 pm

Thanks, yes I found it really inspiring too and such good advice. I’m hoping I can inspire others to find creative ways of working and living abroad 🙂

Rebekah May 22, 2015 at 2:40 pm

this is such an interesting idea. While I was travelling I kept thinking I should buy a ton of jewelry and sell it but I don’t think e-commerce is my calling. I love reading about how people find ways to travel though

madisyn July 23, 2015 at 2:06 pm

This is a very inspiring post! It’s interesting to learn how and why people get into and become digital nomads. I’m still trying to figure out the landscape myself so learning about Ryan’s story is a great example of how it can work. Thank you for showcasing!

Anna Phipps July 23, 2015 at 7:46 pm

Thanks for commenting. Yes I think it’s interesting just how many ways there are to make money and live a life of travel freedom when you are creative these days. That is why I’m doing these interviews so I’m really glad you found it useful! Good luck with your endeavors 🙂

Sue December 18, 2015 at 5:35 pm

Another great post Anna, thank you for sharing. Congratulations to Ryan also… Nomads are all so inspiring!! ????

Anna January 7, 2016 at 7:25 am

Thanks so much Sue! So glad you found it inspirational! 🙂


Leave a Comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.

This website uses cookies to improve your experience. We'll assume you're ok with this, but you can opt-out if you wish. Accept Read More