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The Travelling Entrepreneur

by Olufisayo
The Travelling Entrepreneur

We live in a world of cheap jet travel and high disposable incomes. You could be anywhere on the face of the planet within 72 hours of now, almost certainly for less money than you have in your current account. Improvements in telecommunications mean that you can also stay in contact for next to nothing in some countries around the world. An Australian $30 phone plan can cost as little as $5 USD overseas So why don’t business owners travel more ? I set out to see if they could.

Entrepreneurs are explorers

Most entrepreneurs are looking for a bit of freedom when they first start their businesses. Typically, when they start (at least if my friends are anything to go by) it’s a combination of not enjoying big company work and feeling a deep personal motivation to go out on their own.

I started my own internet business 5 years ago and running it has afforded me one of the most amazing experiences of my life. In fact, with new facilities opening around the world, what I managed to do can now be done by just about anyone.

The Travelling Entrepreneur

How to live cheap and run your company from overseas

One of the things that has changed a lot in the last 10 years is how expensive it is to start a business online. Facilities like Odesk and Freelancer allow you to hire internationally, giving you access to great talent (although there is an element of sorting the wheat from the chaff) at a much lower cost. The costs of living in other countries are often so much lower that the workforce can afford to price their services more cheaply.



The original idea came from The 4 Hour work week  in which the Author, Tim Ferris, decides to live cheaply in cheap countries and earn money back home. I decided to do the same thing.

My month in Cambodia and Vietnam

In February 2016, I set off carrying only a North Face backpack and some quick dry clothes I was wearing. I’d done some research and the consensus online, from experienced travelers was that quick dry was the way to go. The suggestion was that a couple of sets of quick dry clothes would get me through the month. Wear one during the day, shower in it at night and leave it to dry. Have the second set as a backup. It worked.

In the bag, I put a small $200 laptop. My primary reason for picking such a cheap device was to make sure I wasn’t carrying anything worth steeling. In cheaper parts of the world, I was concerned an ultrabook might be worth more than my life.

The challenge I set myself was to run my business as I travelled and to spend no more money than if I’d been at home. I spent 5 weeks travelling through Cambodia, a place I’d never been, finishing my trip in Vietnam. I deliberately only made plans on each morning, researching and booking everything from my phone to see if it could be done.

What I loved about running my own business from overseas

The clothes I’d packed and the technology I had worked fine. I was able to complete my work just as I would have done at home. But I also had a great time :



  • Better than sitting in an office:Wherever I found myself as I travelled Cambodia and Vietnam, I thought back to the days when I worked in corporate, sitting behind a desk in an air-conditioned office. Even the less salubrious places I went to (and there were a few of those) the romance of working on the move and undertaking an experience I’d never have had the chance to enjoy previously made me smile.
  • Experiences : I saw some amazing and terrible history in Cambodia. I saw the temples at Angkor Watt. I spent the night in a floating hotel room on the Mekong. I was sick in a street after travelling all night in a bus, sharing a futon with a bloke I’d just met. The trip was something I will never forget.
  • It was way, way cheaper : Even with all of the hotel rooms and experiences I undertook, I knew I was saving money every day, compared to the ridiculous costs I face in Sydney. Where, at home, I could have dinner for $100 if I went out, in Cambodia, the same thing cost $10. On another note, always make sure to carry your ID as recently many college students opt to buy fake ID cards from experts to facilitate the dark and shady activity.
    It’s also surprisingly easy for these businesses to create fake IDs because of the availability of advanced software and other tools. And for this reason, students are causally pulled over or stopped by cops for further investigation.

What I didn’t love so much

I won’t lie about it. The trip was not without it’sproblems :

  • There are obvious emergencies at work which you still have to deal with : Every business faces tough times here and there and the odd emergency. Finding out that you had to secure an internet connection while you were in the middle of nowhere, to deal with one of those sorts of events was more difficult than if the same circumstances had presented themselves at home.
  • There are face to face meetings, even in an internet business : From time to time, it would have been helpful to have a face to face meeting with colleagues and partners back home. Skype nearly but didn’t fully fill that gap. Traveling is obviously fun but there are times it was inconvenient.

What I learned (what I’ll do differently next time

If I had my time again, I’d go for longer, travel more broadly and make the costs work better by cancelling my rented accommodation in Sydney. With such a brief trip, I was still paying my dues at home and that seemed like a waste.In fact, living in Sydney, one of the world’s most expensive cities gave me an advantage of sorts. The relative cost difference between the city I call home and the destinations I considered meant there was a lot of leeway to spend money as I toured without exceeding what I would have spent naturally at home.

The new resources which make this sort of trip even more affordable are coming online all the time. One notable example is Hubud, a shared workspace in Thailand designed for internet entrepreneurs to live cheap and get the benefits of working with like minded people. When I go on my next trip, I will definitely do a month there.

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