
Bootstrapping overseas as an American - jasonkester
http://www.expatsoftware.com/Articles/bootstrapping-abroad.html?try=3
======
dalke
That was an odd piece. I'll start with the provably wrong statement: "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"

It took me about 2 months to get a self-employment residency permit for
Sweden. While I looked around for lawyers to help, I couldn't find any, and
ended up writing it myself. It seems very few people do that option.

YMMV of course. Which is my point.

But as for the other parts, it depends on the type of person you are and what
you want. I did the 3-month-at-a-time tourist visa option for a bit over a
year. (It's not quite a 'visa run' because it wasn't a cross over the border
and back thing.) It got tiresome to start make friends and then leave them,
then come back, only to leave again.

On the other hand, there are people who do that for decades, and love it.

While I sell software, my customers are businesses, in a market where most
contacts start by meeting people and word-of-mouth. Most of the people who
might buy are in the US or Europe, and that's also where most of the
conferences are held. It's much more expensive to send my bundle of atoms from
South Africa (one of the places I considered living) than from Sweden.

Again, this isn't true of everyone. There's a big difference between "and
start bringing in a few hundred bucks a month from paying customers" and my
software, which sells for a few tens of thousands.

It also becomes harder if you want to have access to a local user's group (I
co-founded the local Python user's group) or makerspace.

So if your interests are surfing, rock climbing, Swedish women, and beaches,
and you are selling direct to customers who expect no personal connection,
etc. then certainly living overseas can be a great idea.

I do believe that living or even just a multi-month travel overseas is a good
thing to do at least once. Just bear in mind that it's not always as rosy as
this author paints.

~~~
a8da6b0c91d
The overseas bit of this seems more about hipster posing; having a slightly
more exotic story to tell. I don't think the cost arguments for relocating to
a developing country make any sense. You can live in third tier cities in
America or Europe very cheaply. It's only major cities that are expensive. I
think in a lot of folks' heads saying "I live by a beach in Thailand" is for
some weird reason more cool than saying "I live by a beach in a cheap town in
Florida."

~~~
dalke
That makes a lot of sense! That would explain my confusion about "most remote"
comment, since it's hard to find a thatch-roofed bar on a really remote beach.
Interpreted as poser one-upping, I now read it as "not where all the _other_
tourists go." Well, except the Swedish women.

FWIW, I spent a couple of weeks living by a beach in Florida in the panhandle.
Not much going on there. Would rather live in a city.

If you want to live in a first tier city, the cost arguments do make some
sense. I enjoyed Cape Town a lot. It had plenty of night life, activities,
stores and other attractions, and even for a tourist month-stay apartment in
the Fresnaye neighborhood, between the mountains and the sea, and with
cleaning every other day, it was about under 1/2 of what I paid in the US.

I didn't like (when I was first in Sweden) the feeling of being illiterate. I
imagine for Thailand, outside of doing tourist things where they cater for
foreign money, that it would be similar.

------
eloff
I do this. I actually live in a large, ocean view condo in Panama City. I rent
half of it on AirBnB which covers all my fixed expenses other than my
mortgage. I work remotely for a Swiss company and I legally pay no taxes. I
don't have a degree, and I've only been working since I was 26. I'll be worth
half a million before I'm 33, partly because my condo has risen in value. I
married a beautiful local girl who probably wouldn't have given me the time of
day in my native Canada. Here I'm taller, handsomer, and richer without having
changed at all, just because the local men lower the bar for competition. The
city is full of things to do, and it's more modern and interesting in some
ways than many Canadian cities. Good beaches are 1-2 hours by car, so sadly I
don't code on the beach (when I go, coding is the furthest thing from my
mind.)

~~~
getsat
You make less than the FOIC cutoff, I assume? If not, how are you legally not
paying US income taxes on foreign-earned income?

~~~
eloff
I'm Canadian, Canada is less possessive of its citizens than the US, if you
don't have residency in Canada (not the same as just not living there
anymore.)

~~~
ZeroFries
Also interested in more details. Maybe a Q&A? Could be valuable to others.

------
peterjmag
_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._

Uh, what? No. Don't do this. Just because you might be able to get away with
it in certain Southeast Asian countries doesn't mean you can get away with it
in Europe. Sure, you might be "fine" for a couple months after your Schengen
visa expires, but good luck if you ever need to, say, fly back to the US for a
few days, or even hop over to the UK. When you try to get back in, you will
almost definitely face consequences.[1]

(EDIT: It's worth noting that you don't even have to attempt to re-enter to
risk getting caught. Even a routine traffic stop can get you in trouble. In
addition, they check your passport at most airports before boarding a flight
that leaves the Schengen zone.)

Yes, self-employment visas do exist (though admittedly only in some EU
countries), and no, they do not require "six months effort and a good lawyer".
In Germany for instance, a freelance visa is a pretty straightforward process,
and the vast majority of people who apply for it do so without hiring a lawyer
or even spending much money.

If you're going to work in a foreign country, at least _try_ to do so
legitimately. You might find that it's not as difficult as you think, and you
won't have to live with the vague fear of serious legal action hanging over
your head.

OP, please don't recommend this to people.

[1]
[http://travel.stackexchange.com/a/13697](http://travel.stackexchange.com/a/13697)

~~~
jasonkester
Yeah, yikes. Definitely don't overstay a Schengen Visa. I'm not sure where you
got that from the article but you're right that it's not a good plan.

Beyond that, I can only speak from personal experience. 15 years and counting
without running into any issue working from the road.

~~~
peterjmag
Ah, it seems I misinterpreted that paragraph. You mean to say that you're
unlikely to get caught working while you're there on an otherwise legal
tourist visa, right? I agree that it's less risky, but I'm still not sure I'd
recommend it. Either way, sorry to jump on you.

~~~
jasonkester
Hey, do you have a link handy for that easy German freelance visa? I'd love to
update the article if there has indeed been such a major change in the last
couple years and it's now easy to get a visa to stay in the EU.

For me back in 2007, several hours on the phone with Spanish immigrations got
me no further than that I'd have to travel back to Los Angeles and deal with
the embassy there for as long as it took, and that the best hope of an end
result would be a visa that was valid for 6 months (instead of the 3 you get
for just turning up).

Anything better than that would be a really pleasant thing to know about!

------
jefe_
A few notes based on my experiences:

1\. Decide who you want to be in your new country, and be that person from
absolute day one. Changes of setting are one of the most effective ways to end
bad habits and start new ones. Want to wake up for sunrise and jog on the
beach every day? Start the habit from day one.

2\. 'Visa-Runs,' do work many places outside of N. America/Europe, but they
must be done religiously. Miss one, and you could face massive penalties.

3\. Go with a business to maintain, not a business idea to build, and be sure
to have a strong support team in the U.S., and at least a handful of well-
enough connected friends in the country you choose.

4\. It's really tough to choose an International Health Insurance plan, but
don't let the vast array of options deter you from doing so. Sure, health
costs are low in many places, but a plan with MedEvac benefits included can
really provide added peace of mind.

5\. Make friends with motorcycle or taxi drivers, and pay them very well.
These guys are the eyes and ears of the city you have made home, and being on
their good side is very beneficial, and enjoyable.

6\. Compensate for time differences with prompt and reliable communication.
People learn not to expect responses from you right away, but if you can
establish a system where clients and partners know there will be a response in
their inbox by the time they wake up, the distance is less noticeable.

7\. It's not easy, but can be an incredible lifestyle for those who go 'all
in.'

------
vdance
I did this with a few differences. It was 2004, so a few services from these
days were not as "available" from a quality perspective -- particularly, VoIP.
I left to France with a PSTN phone device that answered calls to my business
number, and forwarded them to a French PSTN fixed phone number -- all at
international rates, which were a bit more expensive back then. I did later
move to a VoIP service, when the quality was reasonably acceptable.

Time differences in Asia would be different than France - maybe a few hours
too many for me. I particularity loved the time difference between France and
the US (~8 hours). Everyday, there was a whole day of work before my clients
in the US would wake up. If needed, I could make a few calls before I had
dinner and went out.

I had a 3 year established list of clients when I moved there, so that helped.
A fairly stressful aspect of living abroad was that all my clients came in
"locally" by way of local google advertising. And as it happens, when someone
picks up the phone and calls a number that seems local to them, they tend to
assume they're talking to someone who is physically present in their city.

Many clients were turned off after realizing that I was working abroad -- and
not telling them (which I tried a couple times) was very strange as well --
it's just a balancing act. So my suggestion would be to get into a borderless
niche business, if you can -- something like doing "websites for x" \-- where
a company would much rather work with someone with niche products and
expertise, rather than someone local. Then the subject of where you physically
are never really comes up, or makes sense. SAAS would work in that way too, of
course.

------
codecamper
I'm an overseas developer myself, currently sitting on a point break in
Morocco enjoying perfect wifi, powering it all with solar panels.

I'm pretty sure that the 100,000 IRS deduction is only for income earned from
a foreign source. So, if you are like me and have your income coming from
Apple app store sales, then you still need to pay your taxes, without a
deduction.

Basically, the big problem with working out of the US is that nearly all
countries pay way less for software development. Thems the breaks.

~~~
jasonkester
Here's the relevant section explaining that yes, income from a US company is
just groovy for use with the Foreign Earned Income deduction:

[http://www.irs.gov/Individuals/International-
Taxpayers/Forei...](http://www.irs.gov/Individuals/International-
Taxpayers/Foreign-Earned-Income-Exclusion---What-is-Foreign-Earned-Income)

 _Source of Earned Income_

 _The source of your earned income is the place where you perform the services
for which you received the income. Foreign earned income is income you receive
for performing personal services in a foreign country. Where or how you are
paid has no effect on the source of the income. For example, income you
receive for work done in France is income from a foreign source even if the
income is paid directly to your bank account in the United States and your
employer is located in New York City._

~~~
oops
On that IRS page it says:

"For this purpose, foreign earned income is income you receive for services
you perform in a foreign country during a period your tax home is in a foreign
country and during which you meet either the bona fide residence test or the
physical presence test."

It sounds like one must also be tax resident in the foreign country for this
to work?

~~~
jasonkester
That's right. The other piece of the puzzle is that you have to either show
that you're a resident of a foreign country, or that you're physically outside
of the USA for 330 days of the year. (as mentioned in the linked article)

~~~
oops
The IRS page reads as though one must meet both those criteria, not just one
of them?

~~~
masklinn
You must either be a bona-fide resident for an uninterrupted period covering
the whole tax year[0] or have been out of the US for at least 330 full days in
the year[1] although in the latter case your presence in a foreign country
must also be legal according to US law.

[0] [http://www.irs.gov/Individuals/International-
Taxpayers/Forei...](http://www.irs.gov/Individuals/International-
Taxpayers/Foreign-Earned-Income-Exclusion---Bona-Fide-Residence-Test)

[1] [http://www.irs.gov/Individuals/International-
Taxpayers/Forei...](http://www.irs.gov/Individuals/International-
Taxpayers/Foreign-Earned-Income-Exclusion---Physical-Presence-Test)

------
jawngee
I'm doing this in Vietnam. Not necessarily by choice at this point (got
married, having a kid, need to stay now).

The FEI thing only applies if you are paying taxes in your "host" country.
Thankfully, you can minimize the burden in a few different ways. State taxes
are another matter though. I was a resident of NYC, but became a resident of
Nevada before I left.

The visa situation in Vietnam is fucked right now. I was doing the tourist 3
month multiple entry, which you can reup 3 times in country for a year total,
but now you can't do that. Getting the fiancé temporary residency, but you
wouldn't believe how Kafka-esque that whole process is here. Though it wasn't
as bad, or as expensive, as getting a marriage license. That required a shit
ton of coffee money.

It was fun for the first two years, but now I can't wait to get the hell out
of this place.

~~~
jamra
The money you make there must go pretty far though. What do you do for work?
Are you Vietnamese or a foreigner? Sorry I'm just curious. I've been out there
a few times and was considering bootstrapping a startup out there due to the
low cost.

~~~
jawngee
I do consulting work for clients back in NYC, though not as much as I used to.

The bulk of my time is spent on my video editing app:
[https://vimeo.com/110889552](https://vimeo.com/110889552)

Yes, money goes very far here, but you are kind of getting what you pay for.
My apartment is nice, but the water if full of arsenic. My internet connection
is great, when the underwater AAG cable isn't being attacked by sharks. The
food is awesome, until a few hours later when I'm popping pepto like candy.

Sorry, I'm really sour grapes on this place at the moment. The first two years
were amazing, but like once you are really _living_ here, the shortcomings of
the place become all too apparent.

~~~
jamra
You've got good reason to be sour grapes. Hang in there man. I was on the
border of moving there for a short time ~1 year for a large project. The
project didn't take off quite as expected so now I'm trying to get things done
remotely.

After watching the video on your link, I'm a little worried about your health.
You sound very sad. Remember you can always take your wife to the states with
you. Good luck buddy.

------
andsmi2
Aren't you risking tax evasion in the countries you are staying in? If you are
"earning" money and living in Thailand for instance...but not paying
taxes....doesn't the Thai government have a vested interest in you--if they
discover you? And might that not be a rough time in some countries?

~~~
seanmcdirmid
Technically, they would be evading taxes in both the U.S. and Thailand. You
have to be tax resident in another country to take the FEI deduction, and
countries without taxes don't count.

But you can always try to get away with it. I like to sleep at night however
(and of course, china takes my taxes straight out of my paycheck). I'm not
sure if a thai prison would scare me more than an IRS audit :)

------
ErrantX
Bit of a bait and switch at the end: "Then save up $10k in case it doesn’t.
Then book that flight."

As with all things, often it doesn't work out and what you could end up with
is (worst case) stuck somewhere in Asia with no funds, job or house.

This sort of thing works if you have no family. A few years ago it would have
worked, now with a young daughter and fiancee it's harder. And then when
you're living on that beach and you meet a girl? Are you _sure_ you want to
live there for a long long time?

One day we'll travel and live around the world, but I suspect much later. So..
sour grapes!

~~~
vdance
hmmm - "As with all things, often it doesn't work out" ...

not really sure where your source is on this -- I lived abroad for five years
and met many, many people doing this same thing (especially in Bucharest) --
both in I.T. and in other fields -- it's very do-able, as the author describes
-- and as you suggest, it helps if you don't have family

~~~
ErrantX
Empirical evidence of the number of friends who went to Asia for mid to long
term and then came back within 2 years because it didn't work out. And the
incident where I had to help a friend pay his airfare because he was literally
stuck.

Failure rate seemed higher than success rate.

~~~
ashleyp
2 years??? Imo that sounds pretty successful to me. But seriously, the issues
you've highlighed are likely to come down to the individual who decided to
spend all money without leaving enough for emergencies.

Getting to do this for 6 months would be amazing.

Imo. Rewards for this far, far outweigh everything else.

------
freemanindia
I've been doing this in India for the past 10 years. At this point I've
basically set up my burningman camp on an organic farm on the edge of
Bangalore. I run a code school where people learn web development online and
encourage other techies to stop by and work on their projects for awhile. Cost
of living including food and internet is about $100. Americans get great visas
to India. Check us out [http://jaaga.in](http://jaaga.in)

------
OneOneOneOne
What do people do for health insurance in this situation? Or is it a don't get
sick or hurt kind of deal?

~~~
patio11
Single datum: I barely got the words "I quit my job the day before yesterday
and am hence..." out before the friendly clerks at city hall put an
application for (Japanese) national insurance in my hand. Had a card 20
minutes later.

------
neillns
"Here, you’re in luck. The IRS, being awesome, actually encourages you to piss
off to parts unknown with its Foreign Earned Income Exclusion."

How is this the IRS being awesome? This is the U.S. being one of only two
countries who tax its citizens on foreign income.

------
ochoseis
Anyone doing this in Hong Kong? The GF is considering a move to HK with work
and I'm trying to sort out how I'd scrape by if I wanted to tag along...

~~~
chatmasta
I just got back from a trip to HK. While I'm sure it's do-able, be forewarned
that HK is just as expensive as any other major financial center. Don't expect
prices to be cheap just because it's Asia.

~~~
Taniwha
I know people who are living in Shenzhen (a subway ride away) and commuting to
HK - the whole "visa-run" being the morning commute

