Bootstrapping overseas as an American

There's something rather romantic about the notion of living on a tropical beach and working away on your laptop. And you know what? It's one of those few instances where the real version is actually just as awesome as the romantic ideal.

In fact, you need to quit thinking about it as a romantic notion. It's something you can do. And it's high time you did it.

Here's how.

Have you noticed how much easier it is to run a software company than pretty much any other type of business? You don’t need office space, a retail storefront, telephones, employees, or even an address. Other businesses need all those things.

We get to run the whole thing on a little server stuffed into a data center someplace. probably someplace we’ve never even visited for all we know because the only indication we have is that the machine has “us-east” in its name. Is there any reason that we need also be in that half of the US?

In practice, we can just as easily be in “Thailand-south” and nobody would ever know the difference.

Would anybody know the difference?

Real Companies have phone lines with people who answer them. We have Google Voice patched into Twilio patched into some funky 3rd world carrier who, incidentally, does a much better job of ensuring that your phone will ring on the beach than AT&T ever did drilling through the walls of my apartment in Portland.

Real Companies have mailing addresses and Business Bank Accounts. So do we. We set that bank account up before we left, using the business address, which by coincidence happens to be the same as that of our parents’ house or, if we were getting all fancy, an office-in-a-box in Deleware or Nevada.

Am I allowed to work there?

No, not really.

But they’re not checking. Places like Southeast Asia are chock full of expats living there, doing silly things like “visa runs” to the next country and back every couple months to remain a tourist for years on end.

Even in Europe, where you wouldn’t be able to get a self-employment working visa (if such a thing existed) with less than six months effort and a good lawyer, you’ll find that they’re really a lot more interested in keeping the various people coming in from the South from doing so than they are in messing with you. Given the level of effort required to find somebody at the Santander ferry port to even stamp your passport, it’s unlikely that anybody is conducting a multi-month surveillance of your AirBnB “office” up in the hills above the Cote de Azur.

What about taxes?

Here, you’re in luck. The IRS, being awesome, actually encourages you to piss off to parts unknown with its Foreign Earned Income Exclusion. Basically, if you can prove you’re a Bona Fide Resident of another Country (which you can’t) or that you’ve been Physically Present outside the US for at least 330 days during the last year (which you can), then they’ll let you deduct nearly $100,000 from your income before taxes.

Naturally, it’s never as good as it seems, but even after they’ve clawed back your self-employment taxes and a few other things, you still get to write off a nice chunk of change from your taxes. Certainly enough to pay for your room & board in a place like Southeast Asia.

Can you really work from the beach?

Of course. It’s the Future. The Internet is everywhere. Step One is to find the most pleasant, most remote, cheapest, most Swedish girl having beach available (prefereably with good rock climbing and/or surfing). Step Two is to find a thatch-roofed bar on said beach with cheap beer and a good view of the sunset. And we’re done. They’ll have wifi.

Now we start a radial search outward until we find a pleasant little bungalow with monthly rates. $400/month will buy you a lot of developing-world-luxury in this day and age. That’s even less than it would cost for a 1BR apartment in San Francisco, I’m told, and it comes with Utilities paid.

How long until I run out of money?

An alternate plan where you get to keep your day job...

You don't even need to go out on a limb to pull this off these days. Plenty of companies offer remote work as an option, and few will actually go so far as to specify just how remote you can get. Nicaragua is on Dallas time, and yes, they have internet there.

They also have nights and weekends, so if you think you can bootstrap your idea up here, there's no reason to expect you won't be able to down there.

You won’t.

The unexpected reality is that living out of a backpack in most of the sunnier bits of the world is cheaper by far than living in a city in the US. Even on a couch. With roommates.

You’ll spend your time building a business. A real one that charges people money in exchange for stuff and hits profitability fast. You’ll fight for a while and start bringing in a few hundred bucks a month from paying customers. Beach life will be paid for at this point and now the goal shifts to building the revenues and getting to “I can live on this money”, then “day job replacing money” and hopefully one day “I can retire off this money”.

And you can do it all from that beach.


I’ve actually done all of this. Chances are I’m not the first person you’ve met who has. It’s not in any way difficult except in that it represents a Big Change.

Figure out how to convince yourself that it’s going to work. Then save up $10k in case it doesn’t. Then book that flight.

Can’t ask fairer than that. Good luck!

Jason Kester

I run a little company called Expat Software. Right now, the most interesting things we're doing are related to Cloud Storage Analytics, Online Classrooms, and Customer Lifecycle Metrics for SaaS Businesses. I'll leave it to you to figure out how those things tie together.

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