travelling | Successful Software

Running a software company from a laptop while travelling the world sounds like a dream lifestyle. But what is it really like? Steve McLeod was kind enough to share his experiences as a nomadic software entrepreneur.

Running a one-person software company while travelling doesn’t work. And yet I’ve been doing it for years. I’m writing this in Patagonia, in a hotel lobby. There’s pop music playing too loud to fully concentrate. The Internet connection is sketchy; in fact I’m writing this now because the Internet is unavailable again. The chair is not good for my posture. The table is too high for comfortable typing. My productivity is abysmal.

I’m partway through adding a new feature to my software, and doing it in this environment is unproductive. There is a big glacier an hour’s drive from here that I’d rather be viewing. I know that tomorrow or the next day, when I see the glacier, I’ll come back to the hotel too exhausted to code or to deal with customer support.

What does this mean for my business? Low productivity and poorer-than-intended customer support response times, which lead to lower sales. My alternative to spending a decent part of each year travelling would be to stay in my home city, working better, selling more software and earning more money.

Here are some real problems I’ve faced working on the road:

In Ukraine my MacBook Pro’s screen stopped working. I didn’t intend to return home for another week. I had to choose between returning home earlier; trying to get the computer serviced promptly in a foreign country; supporting customers for my Mac software for the next week on Windows computer in Internet cafes; or buying a new computer and trying to get all my development tools on it.
In Turkey, YouTube was blocked. Which was mostly a good thing for productivity, but as my video demo was hosted on YouTube at the time, I couldn’t monitor it.
In Syria, Facebook was blocked. Okay, that was incontrovertibly good.
In Turkmenistan there was no Internet in my hotel. Or any hotel, just about, except on age-old computers in one hotel’s inaccurately-named “business centre”. No WiFi in cafes. For a few days my company was getting no attention.
Travelling in a shared taxi for hour after hour between obscure locations in Iraq (true story!) left me utterly spent. All I wanted to do after getting into a hotel is to relax. But that customer support backlog is nagging, nagging, nagging at me.
Skype is blocked in Qatar and in some other countries. This really ruins the conference call you had planned.
In Lebanon I needed to update my product with a critical fix. The Internet at the time in Beirut was so bad, it would take an hour to upload my 20 MB software. An hour! During which time I’m hoping not to get a network disruption, from one of Beirut’s daily 3-hour power outages. My 2-minute scripted solution for building and uploading updates, followed by a 5-minute smoke test turned into a 2-hour task, during which time I need to keep ordering coffees so as to keep the staff happy in the cafe supplying me with WiFi.
Coding while sipping a cocktail in a beach-side bar in the Caribbean is difficult. The brilliant midday sun makes the laptop screen hard to read. Actually that doesn’t sound too bad at all.

A very real risk includes getting my computer stolen, which, by some miracle, has not happened yet.

How do I make this running-a-one-person-company-while-travelling thing work? Here’s some things I do:

I keep everything in multiple online places. I use DropBox for documents and code. I use GitHub too. Without excuse, everything needs to be recoverable without drama if the computer breaks or gets stolen.
I set aside frequent rest periods where I can get through a backlog of harder customer support issues and work on new features or bug-fixes. It is actually nice sometimes to not climb Andean glaciers nor to see orang-utans in Borneo, and instead to do something prosaic like working for a day or two.
I try to be disciplined in keeping my customer support inbox empty. When I arrive at a new hotel after a long, dusty trip, before rewarding myself with an ice-cold beer, I’ll force myself to tackle the inbox.
In recent months I’ve been outsourcing customer support. I pay my support representative a monthly fee in return for which she deals with what she can handle herself each day. This helps so much.
I aim to spend my months in my home city in high-intensity bouts of feature-adding, taking advantage of having a good work environment.
I produce desktop software. Not SaaS, which would be terrible to support and monitor in these environments.
Moving source control from Subversion (which needs an Internet connection to be usable) to Git has helped a lot.
I concentrate on keeping my software as solid as I can, and the user experience as smooth as possible. These two things help reduce the customer support load.
I try to keep things in perspective. Yes, getting my computer stolen would be a minor catastrophe. Yes, a sketchy Internet connection is annoying. Yes, some customers might get irritated at the occasionally slow support. But here’s the other side: Three years ago the city I grew up in was destroyed by two earthquakes, killing hundreds and destroying a significant amount of the city. A year before that I suffered a terrible personal tragedy. Do other things matter so much that I should sit at home to keep customers as satisfied as possible?

Although my lifestyle might seem enviable, it can be lonely at times. You don’t realise how nice it is to be able to regularly catch up with the same friends for dinner or a drink until you can’t do this for long periods. Luckily, I often manage to find someone I know well to join me for part of each trip. Here in Patagonia and beyond, my girlfriend is travelling with me for two months or so. I’d not be travelling for so long anymore without companionship.

On the other hand, my one-person software company has enabled me to reach a goal I’ve long had: to travel to more than 100 different countries. I earn a decent income from my work and thousands of customers love my software. And that is enough for me.

St Vincent and the Grenadines

St Lucia

Croatia

Guyana

Oman

Beirut

Perth

Photos copyright Steve McLeod.

Steve McLeod runs Barbary Software, a one-person software company. Barbary Software’s main product is Poker Copilot, hand history analysis software for online poker players on Mac OS X.

The experiment begins

For six months, we tried to manage our software business while teaching English and doing odd jobs for NGOs, newspapers and radio stations. We had brought with us two Mac laptops (a PowerBook G4 and an iBook G3), which were both maxed out as far as hard drive and memory were concerned, an extra battery for the G4, an external keyboard, a digital camera, and various cables and worldwide plug adaptors. We had also brought a CD case full of original software discs.

Tbilisi home office

In the end, the multiple infrastructure problems that plague the Republic of Georgia (mostly a serious lack of electricity) proved too much for us to bear. We escaped to Germany, carrying 170 pounds of stuff, including our two laptops, a UPS we had purchased in Tbilisi and a Persian carpet we had bargained for while on Christmas holiday in Dubai.

After a few weeks recovering in Germany, we spent a few months in Prague, Czech Republic. When the cold weather arrived, we flew south and spent eight months travelling around the Indian Ocean, South East Asia and Oceania. Shortly thereafter, we landed a software development contract in Dubai and relocated there, but regularly escape to Prague during the blistering summer months. We currently own a flat in central Prague and have considered buying a flat in Dubai.

Kampala, Uganda

By keeping a small base in one or two countries, we can have a “home”, a decent place to work and a life, while still taking long trips with the backpacks. Running the business from an apartment in the developed world is fairly straightforward. What’s challenging is running the business from a backpack while spending several months on the road.

The essentials

Everyone wants to sit on a beach and work only four hours a day, but the reality is a little different. If you are actually running your business, you’ll spend as much time working on the beach as you would in a cubicle. It’s certainly possible to work only an hour a day for a few weeks, but to develop and grow your business, you will need to spend time actually working, rather than sightseeing. It’s not a permanent holiday, but rather an opportunity for frequent changes of scenery.

As a practical matter, you can only travel with what you can carry and a good backpack with detachable day-pack is the only serious option. Since you are carrying a few thousand dollars worth of equipment, security becomes an issue, especially in poorly developed parts of the world. We generally stay in the least expensive hotels we can find that have adequate security and cleanliness, while occasionally splurging on something nicer to maintain our sanity. It is very important to budget properly for long trips. For some people this may be as much as $200/day, and for others it may be only $50/day, but managing expenditures is even more important when on the road. Of course you’ll soon realize that for the same money spent during 4 days in London, you could spend weeks in South East Asia or poorer parts of the Middle East.

On journeys of a month or more, we generally bring two up-to-date Mac laptops (currently 15″ and 17″ MacBook Pros), worldwide plug adaptors, software CDs, two iPods (one for backing up data), a digital camera and two unlocked 4-band GSM mobile phones. For longer-term backup we burn a data DVD about once per month and post it home.

Essential software includes Excel, Entourage, Filemaker Pro, Skype, iChat and, of course, the Apple Xcode Developer Tools. Speed Download saved us in Tbilisi because of its ability to resume downloads after our dial-up internet connection dropped the line, which it did every four minutes!

Surprisingly, the best Internet we have found in the developing world was in Phnom Penh. WiFi can often be found at big hotels, but it is more common to connect via Ethernet in a cafe, where a basic knowledge of Windows networking will allow you to configure your laptop to match the existing settings of the cafe’s PC. In the least developed countries, modems are still the norm.

Kigali, Rwanda

One important consideration, especially in countries where censorship is common, is that many places require you to use their SMTP server for outgoing mail. This may not work with your domain as a return address. To get around this, it’s useful to have a VPN, such as witopia.net, and an SMTP server at your domain.

Visas, taxes and other nasty stuff

If you have a western passport, visas usually only become an issue when you want to stay somewhere more than three months. Often, it is possible to do a “visa run,” in which you briefly leave the country and immediately return for another three months. Many countries make it easy to set up a local company, which can allow you to obtain longer-term residency visas, but there is a lot of paperwork involved with this. Staying more than six months as a “tourist” anywhere can be a problem as you’ll almost certainly have to deal with immigration issues.

Hong Kong

Although Dubai has straightforward immigration procedures and is a fabulous place to spend winters, the UAE Government blocks more websites than just about any other country on Earth. Even Skype is blocked because the local telecommunications company doesn’t want any competition. Unless you are able to find a way around the blocks (wink, wink), running any kind of internet business from Dubai will be fraught with difficulty.

Even if you are living in a tax haven, if you are a US Citizen, you can never fully avoid US taxes, although you can take advantage of the Foreign Exclusion. Local taxes aren’t really an issue if you’re just a “tourist” spending a few weeks in a country, but they can become an issue for long-term stays. If you are planning to stay somewhere for more than a couple months, and “settle”, you’ll need to research tax ramifications.

Sana, Yemen

Since we left the US, our taxes have become much more complicated. Fortunately, we found an American tax attorney to handle our annual filings. He lives abroad and therefore understands the Foreign Exclusion and other tax laws regarding expats. For our microISV, payment is handled online by two providers (always have a backup!), and ends up in a company account in America. We use a payroll service to pay our salaries into personal accounts, which we can access by ATM. We also have established a managed office in Nevada to act as our company headquarters and handle mail, voicemail and legal services.

We have no regrets about having left the US for our big adventure. We have truly lived our dream of being able to travel indefinitely, but sometimes it is wearying not knowing which country we will be living in just a few months into the future. Our ultimate goal is to own two properties on two continents so that we can travel between them with just a laptop.

by Karen Inda

photographs by Trygve and Karen Inda

Trygve & Karen Inda are the owners of Xeric Design. Their products include EarthDesk, a screensaver with a difference for Windows and Mac. They were last spotted in Prague.