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Bootstrapping overseas as an American

expatsoftware.com

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Re: Bootstrapping overseas as an American

#21

Post by 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!

Re: Bootstrapping overseas as an American

#22

Post by codecamper »

jasonkester wrote: post #12
peterjmag wrote: post #8

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, yo…

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.

Please don't be so afraid of the Schengen zone. If everyone follows this advice there will be no more US / European marriages.

You can hop between Schengen and UK or Ireland, or Croatia, or Romania indefinitely. Nobody will care.

The UK is the hardest of them all -- asking tons of questions. Nobody else is so tough. So go to Ireland. Nicer people and much better weather. (just one of these is true) If you want to go to the UK, go there from Ireland. Nobody will ask a single question then & there will be no stamp.

15 years ago it was much easier. I lived in the Czech Republic for > 8 years, without even bothering to get a Visa. Many people I knew did the same. Never heard of anyone having a problem except for one friend who was a little bit drug crazed and burnt out and had a bit of a spat with a border officer on the way out. Now CZ is schengen, so you need a Visa, or you need to stay just 3 months in 6.

Re: Bootstrapping overseas as an American

#23

Post by vdance »

ErrantX wrote: post #21

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 b…

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

Re: Bootstrapping overseas as an American

#24

Post by 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?

Re: Bootstrapping overseas as an American

#25

Post by codecamper »

semperfaux wrote: post #20
codecamper wrote: post #6

Earlier quoted context omitted.

Interesting! I stand corrected. Next thing I don't understand with that document is what is "earned" income. Are app store sales "earned?" I'd say so... constantly having to update the software -- I'm earning it.

Is this facetious? Because it's a little funny to expect the IRS to be so literal. In my experience, either it's "earned" in that it's been paid directly to you or it's indirect income (e.g. dividends you were paid on an investment you aren't directly working on or appreciation you haven't collected on) that are still going to be taxed on in one way or another.

They are incredibly literal in a few cases. Such as:

"Professional fees. If you are engaged in a professional occupation (such as a doctor or lawyer), all fees received in the performance of these services are earned income."

(great.. special rules for lawyers)

But they make up for it by loving artists: "Income of an artist. Income you receive from the sale of paintings you created is earned income."

I wish they sit down and analyze software and make some hard & fast rules -- it's the computer age and we are being treated like "writers" or "professionals" or whatnot

Re: Bootstrapping overseas as an American

#26

Post by seanmcdirmid »

andsmi2 wrote: post #24

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?

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 :)

Re: Bootstrapping overseas as an American

#27

Post by ErrantX »

vdance wrote: post #23
ErrantX wrote: post #21

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 b…

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

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.

Re: Bootstrapping overseas as an American

#28

Post by hn_user2 »

peterjmag wrote: post #8

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, yo…

I don't think the author is suggesting anyone overstay their visa.

I also work remotely in Thailand at the moment. Leaving and coming back every 30 days. Its a great excuse to go see nearby countries and to disconnect and take a break every month.

I can say for sure there is no "vague fear or serious legal action hanging over my head".

There are many people working here illegally in actual jobs, taking money from the Thai economy on improper visas (English teachers, etc), which the Thai government is not too happy about. When they find out they deport them.

The last thing that is on their radar is a tourist at the beach doing a little remote work, getting paid outside of the country.

So if that type of situation would be something that makes you nervous, then obviously don't do it. But if you are keeping everything mobile, worst you face is a deportation (have yet to hear any instance of it happening to a digital nomad) in which case you setup shop in the next country over.

Re: Bootstrapping overseas as an American

#29

Post by jasonkester »

peterjmag wrote: post #16
jasonkester wrote: post #12

Earlier quoted context omitted.

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.

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.

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!

Re: Bootstrapping overseas as an American

#30

Post by 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.

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