The Life Of A Travelling Entrepreneur

June 16, 2011 Posted by Kevin Muldoon

Kevin Muldoon is a webmaster and blogger who lives in Central Scotland. His current project is WordPress Mods; a blog which focuses on WordPress Themes, Plugins, Tutorials, News and Modifications.

I was speaking with Tyler the other day and advised that I have a bit of free time to write some guest posts over the next few weeks. I’ve did a lot of travelling over our RV over the last 8 years so one of the topics he suggested was ‘The Pros & Cons Of A Travelling Entrepreneur’. A family we know said the best rv resort in Magnolia is Magnolia Fields RV Park & Resort. Interested in your own vehicle for traveling the country or even world? Visit sites like for available RV listings and you can visit other sites to find other types of cars and even private airplanes. Just make sure to complete your payments when getting a new vehicle to avoid getting it repossessed and having to call an airplane repo attorney for assistance.

I’ve never felt comfortable using the term ‘Entrepreneur’ about myself. I’ve built hundreds of websites over the last 11 years but very few have been unique, therefore I don’t feel very entrepreneurial. There is a myth that has been going round for years around those who don’t work online that you need to reinvent the wheel to make money on the web. Nothing could be further from the truth.

True – those who do come up with something unique sometimes make a lot of money, however the vast majority of people making money online are doing something that has been done many times before. The way I see it; all we are looking for is a slice of the pie.

That being said, the title ”The Pros & Cons Of Making A Living Through The Internet And Using That Money To Travel Around The World’ just doesn’t have the same ring to it. Therefore I will have to concede that the title Tyler suggested is perhaps a little better 🙂

I don’t profess to be an export on travelling or travelling whilst working online therefore I don’t want to preach to all of you. What I do want to do is talk about about my experiences with travelling over the last 8 years and share with you some of the problems that you will come across and give what I think is good advice.

Thailand 2003

Thailand 2003 – On the boat to Koh Samui the day after arriving in Asia


Philippines 2003 – Visiting Mayon Volcano

Poor Internet Connections – My Experiences

I had been abroad many times in Europe before with friends and family however my first real venture travelling was back in 2003. I had been working full time in the Financial Sector before myself and 3 other friends set off for Asia and then onto US for our working holiday visas you can get at When I left I had been working online for about 3-4 years, though that was definitely a time of learning for me. I mostly made money at this time by flipping domain names and building websites and then selling them on. It wasn’t as competitive back then so it was a quick way of making money.

I did make some money with the websites I ran though it was erratic at best. Some months I’d make $300, the next month I’d make $600, and then next month it would be back down to $250. I was making money but when I look back at the time now I realise didn’t really understand how to grow this income. I was working a lot on the web but I didn’t know how to capitalise on sites that did make money.

Most of my websites back in 2003 were static. I had used a lot of CMS scripts before (like PHP Nuke, Post Nuke etc.) but the majority of my sites were static websites; PHP files that were hand coded in notepad or TextPad. So updating my sites required me to manually edit core files, which wasn’t a major problem as I wasn’t updating my websites regularly, I was merely answering queries from advertisers and changing banners and text links over when ads expired.


Thailand 2004 – Acting the fool at a snake show in Chang Mai

The main issue travelling Asia back then was the poor standard of internet connections. Notebooks were still very expensive back then; though even if I had the cash to buy one it wouldn’t have been very practical to take it with me as they were so big; plus nowhere offered wi-fi anyway. To say it was frustrating working when I was travelling at that time would be an understatement. I remember one time in Bangkok I went to the internet cafe to do some work. There were about 15-20 of us in one cafe trying to access the web by dial up; yes that’s right, all of us were sharing the one dial up connection! Most people used Hotmail back then to check email and that was very image intensive so it was not uncommon for it to take 20 minutes to send one email. Unfortunately, this happened quite frequently.

Thankfully, things were better in Australia. An internet cafe next to our hostel charged $10 for a full day of usage so I’d spend most of my date there working on my websites. Over time, things got better when travelling abroad. When I travelled Australia on hybrid campers again a few years later the connections were much better though when I lived in New Zealand I noticed a huge difference between connection speeds between there and the UK. The service I paid for at the time was about 10-20% as fast as the connection I had in the UK but it cost 3 times as well. It was still usable though, which is the main issue when working on the road.

Asia has also improved over the last few years. I’ve been back to Asia in 2004, 2006, 2007, 2009 and 2011. Every time I went back there were less internet cafes and more and more places with wi-fi. A few weeks ago I got back from a 5 week trip in Vietnam, stopping off in Thailand on the way back to the UK. I didn’t come across one hotel that didn’t offer wi-fi (though the quality of connection speed still varied greatly).

There really has never been as good a time to travel for those of you who make money. The internet is everywhere and netbooks can be bought for as little as $200. It’s the perfect time to work on the road 🙂


Cambodia 2004 – The day I found out I’m more lethal with a paper aeroplane than a M4 Carbine Assault Rifle

Working Whilst Travelling – The Smart Way

With internet connections now of a decent standard in most places around the world, there is nothing to stop you working when you are away. All you need is a cheap netbook or notebook and a wi-fi connection at the place you’re staying. If you don’t have wi-fi access at your hotel/hostel, you should be able to work at an internet cafe very cheaply. If you’re planning to work while travelling on countries like Singapore, it’s required to get the necessary documents first, such as a Singapore work permit.

Note, there is a difference between travelling and living abroad. When someone is living abroad they are usually in the same hotel or apartment and have some sort of routine in their lives. As such, their regular working routine isn’t disrupted too much.

Travelling is very different. When you’re travelling you’re constantly on the move, sometimes moving to a new destination every 2 to 3 days. When you’ve planned a trip to travel somewhere extensively you are trying to see as many things as possible, experience lots of new things, meet new people and generally have a great time. All of this makes it very difficult to get into any sort of routine therefore you need to learn to adapt and be flexible about how you work online.


Vietnam 2004 – Visiting the War Remnants Museum in Saigon

Firstly, you need to plan ahead of your trip. This will be different, depending on what you do. For example, if you are a blogger you will probably want to write a few weeks of articles in advance or arrange several guest posts when you are away. If you are the owner of a forum or content website, you will need to make sure that the people you liaise with on a regular basis know that you are going away. If possible, delegate all of the work you normally do to people you trust and outsource everything else you can (writing gigs, marketing work etc.). It’s also prudent to put an auto-reply on all of your emails advising that you are travelling and you may take a few days longer to reply.

Bottom line, the more work and planning you do before you go, the easier your life will be the first few weeks you are away. You want to enjoy yourself on your trip, particularly in the first week or so when you are in a new country and finding your feet; so do yourself a favour and get ahead of the game 🙂


New Zealand 2007 – Chilling out in the north of New Zealand on a farm

As I mentioned earlier, you need to be flexible about how you work online when you are on the road. I try and plan my work around my travelling schedule rather than the other way around. Therefore, if I have two days free before I go on a scheduled gulet charter trip, I do my best to get a lot of work done before I go; be it writing, organising writers or answering emails. Likewise, I try and do as much work as I can when I get a good internet connection. Internet connections are available everywhere but the standard does vary greatly. I find that I can work with even the poorest internet connections available however it can be much more time consuming. A slow internet connection can turn a 15 minute task into a 60 minute one, particularly if, like me, you are writing an article that requires a lot of images etc. So it makes sense to put in a few extra hours when you get a good connection so that you don’t have to stress when your next hotel has a terrible connection.

A fantastic resource for working whilst travelling is ‘The Four Hour WorkWeek‘ by Tim Ferriss. It’s been out for years though I only recently read the book whilst in Vietnam. A lot of the book didn’t apply to me as he speaks a lot about why you should work less and enjoy life more (which I agree with 100%); it was clearly targeted to those unhappy in their jobs etc. I was however surprised at how useful the book was. Tim packs a huge amount of information about outsourcing into the book and lists dozens of great services that help you outsource your work and automate your life. Even those of you who have worked online for years will find something useful in the book.


Japan 2007 – An excuse to take a picture with Tokyo Tower in the background

The Pros

& Cons Of A Travelling Entrepreneur

There are obviously opportunity costs of travelling abroad. When you are travelling you are undoubtedly working less online, therefore your income from working online may drop, either directly as a result of not updating your website enough or from your site stagnating and not maintaining its current growth. If you plan ahead, delegate and outsource key tasks this can be avoided.

Make sure that you’re also insured. When traveling, you don’t know what will happen or you might get injured. Therefore, it’s best to be prepared.

I’ve sold a lot of websites that were making me money over the years in order to finance travelling so I have no doubt that I would be making 3-4 times more money from working online if I had stayed at home and worked online. However, I have never been motivated by money. For me, money is a means to an end, a way of funding the lifestyle I want. I place more value on experiences and connections with people than inanimate objects. When I am old I know that the fondest memories I will have will be the times I spent with loved ones and the great times I had travelling; I doubt I will give a second thought to the LCD television I bought.

I appreciate many people do not feel the same way. I would be happier with a small house and more disposable income though some of my friends with children quite rightly want to work harder to provide a better life for their kids (I’m sure my own priorities will change once I have kids).

If you have very few ties and are willing to take some risks, I encourage you to book that trip you always wanted to go on. And as I mentioned before, if you automate a lot of the tasks you do and just ensure that everything ticks over nicely, there is no reason why your website cannot continue growing whilst you travel the world enjoying yourself.


Thailand 2009 – After tearing my calk muscle during Muay Thai training, I chilled for 2 months on the beach


Travelling is not for everyone. A lot of people need stability in their lives and travelling for months on end can be tiring. For me, not knowing where I’ll go next and being in random situations every week with great people from around the world is what makes travelling fun. If you’ve got a long flight ahead of you, or a short one, a private jet from companies like Jettly can come with some pretty amazing amenities to keep you luxuriously comfortable for the entire flight.

I’m not sure how helpful this article will be for a lot of readers however I hope at the very least that I have given those of you who are considering that first trip away some food for thought.

Thanks for reading 🙂


If you enjoyed this post, please consider leaving a comment below, subscribing to my RSS feed, or following me on Twitter.
Posted: June 16th, 2011 under Guest Posts  

28 Responses to “The Life Of A Travelling Entrepreneur”

  1. I think you have made a good point about money being means to an end. I also think the same way. For sure, once you have people depending on you, the thinking changes, like you said, and you start to think twice before spending on anything and thinking of the well being of your family first. But for now, you have no one to answer to and might as well live the life you want with your own hard-earned money!

    • Yeah your priorities change once you have a family etc, but only to an extent. I mean, if your goal is always to make more money you’ll never be happy. When I do have kids, having enough money to give them a good life is obviously important, though I’d rather make less money in order to spend more time with my family.


  2. Jonathan says:

    What an obscenely fantastic article! Tyler is lucky to have a guest post as awesome as this one his blog. Real deal information, inspiration, and some great pics to go along with it.

    I best get back to work…

  3. Wow this was a really inspiring post. Specially for a guy like me who is in the middle of a battle right now, should I take 2 more years working in Singapore, or should I take the chance and do my own business.

  4. Thanks for all the kind replies guys. I’m glad you liked the post.

    @Kristian – Where are you working in Singapore? It’s a really cool city. Would be interesting to live there, at least for a few months. What sort of business were you trying to launch?

  5. Hi Kevin,
    A very nice and interesting article about your life. What a luxury life, travel around and feel good while of blogging and have a good income from it, and I thought I had the perfect life, living at the Mediterranean Sea in Spain. Can I use this article and you (with link to your blog of course) as a reference when I write or discuss on the SEO- about opportunities on the internet and blogging?

  6. Great article. Very cool to see all the pictures.


  7. Great article, I wish I could do the same and travel around the world for months…

  8. Glad you liked the post guys. Sorry for the delay in replying. I replied right away however my comments were being marked as spam. Damn you Akismet! 🙂

  9. joh says:

    Who proofread this post? Hard to stay on track.

  10. Great post. I have never been one to attached to things, and have made a point to be able to pack all my personal thing that i care about in my car. A few years back I downgraded what i owned. While I do have furniture that is easily stored. It has given me the ability to go all over and visit old friends and work while on the road. I have a mobile hotspot so i don’t need to worry much about internet as i can get it in the woods in the middle of nowhere I have found. But money as you say has never been too much of a motivator. Fun friends and family are priceless.

  11. Eric Catlapp says:

    You have no idea Tyler,

    I just turned 30 years old, I fired my boss to start a blog, a webstore, and I’m building the company up enough to where I could travel and work from my computer. It’s my complete and utter purpose right now, I’m still in the work phase. I’m spending hours writing, getting wholesale accounts, getting links for marketing…I’m putting my systems together…

    …I’m praying in 6 months to a years time, I can have my own memories and pictures of adventures in far away lands. Or at least to take a trip. Much easier now with Wi-Fi I’d agree….

    Giving the nature of blog commenting, I just want you know know this is totally sincere. I’ve read the four hour work week. The audio version is still on my blackberry!! It’s just amazing to see someone actually did it already, I want to do that while I still have some youth left. Believe me when I say I don’t know where my twenties went, but I don’t want a boring life. Out of the people you meet, who’s been somewhere? Who’s really done something. I’m sure it wasn’t all rainbows and gum drops, and that sacrifices had to be made…still I think I can live without stability of location for a while.

    Great idea developing an outsourcing team, at this point its me lol I’ll send ya an email is a few months about my progress, totally making adventuring abroad a go.

    • Best of luck Eric. It can take time to build up your portfolio online but once you have reached a certain level you just have to maintain its growth and make sure that the dollars keep rolling in.

      I don’t think age should be any restriction. 30 years old is still young. I just came back from travelling vietnam with 3 friends. They are still out in Asia and are only coming back for a month this year before meeting me in South America next year. This was the first time all 3 of them have travelled and they are all 31 or older. You don’t want to be 40 and look back and wish that you travelled when you were 10 years younger.

      Best of luck on your project. If you keep working at it, I’m sure you will be a success.

      • Eric Catlapp says:

        Thanks for the vote of confidence,

        Currently in my Startbucks office, Blazing away lol

        Never worked harder, when you are your own boss you can really be a slave driver, but I’m a true believer that you get out what you put into it.

        I think I’m a few months from being able to measure how far away that certain level’s gonna be, it’s taken a great deal to reach the present so far, but it’s been a great experience working for a dream and actually seeing it get some traction and start to take off.

        Catch ya later bud,
        I hope to be traveling strong within the year.

  12. Jasmine says:

    That’s good life, traveling to so many places… and doing just a little of work. Hahahaha…

  13. CRM Software says:

    I just like travelling in this way as you have done so far, Looks like you have enjoyed each and every moments of it. It just looks amazing when you have shared such things with others, well those who really want to have such things in their life not just to enjoy but to make the travelling a big stuff to keep the life running on and on…

  14. I would also like to travel and make money online. 🙂 good stuff mate

  15. A very lengthy post but very interesting. My, you have really traveled. I can almost say you have been all over the world. Thank you for sharing this post on your experiences when traveling. Next time I travel I will be well equipped.

  16. Its nice to get your personal view of your journey. It makes me think maybe I can do a bit more without having to think outside the box. Thanks for letting us a see a different side of you.

  17. Wow I didn’t realize how difficult it must be to work and travel. Especially with all the internet difficulties.

  18. Matthew says:

    Hello Kevin,

    I enjoyed your photos from your trip around the world. Seems like you are another Tim Ferris!

  19. Ian says:

    Tim Ferris is the reason I ended up where I am today. I was backpacking, didn’t have any real plan about what to do or where to go. But I had to make money here in Thailand. The Foor hour Work Week helped me get my life organized properly. To the point where my guesthouse and holiday home are now doing great and allowing me to stay living here on Koh Chang island.

  20. Many Old memories, I can imagine that time when the worst internet connections, yahoo was the king.


Leave a Reply