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Ask HN: Living overseas with a profitable online business

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Re: Ask HN: Living overseas with a profitable online business

#81
I have been doing the same thing since 2001. In the UK, USA, Italy, Australia, switzerland. I am now in southern california I am a us citizen but if you are a foreigner you can easily and within 2 months buy yourself a place in the USA by getting a E2 Visa - Invest $120K in your own viable business (investments include your salary) and you are in!

Re: Ask HN: Living overseas with a profitable online business

#83
post #66
post #18

Don't know about UK, but in Canada one can stop paying taxes once all "domestic ties" are severed. This means closing all bank accounts, disconnecting all phones and selling the car and the real estate (or alternatively leasing it out for a long term). Even after all this is done, the tax agency (CRA) will not assume you to be a non-resident if you do not stay out of the country for at least 2 years. So it is a hassl…

Is it really 2 years? You can't speed it up in any way?

The way I understand it is if you come back for residency in less than two years, CRA may have some questions.

Re: Ask HN: Living overseas with a profitable online business

#84
post #65

Earlier quoted context omitted.

Absolutely don't buy a RTW ticket. Definitely go around the world, but do it by purchasing a single one-way ticket. Travel overland as much as you can and when you hit the end of a continent, buy another one-way ticket to the next. There's nothing worse than having a date on a calendar. It will mess up your trip over and over again, even if it's months in the future. Avoid dates at all costs. Get to the first place a…

Don't feel like you can't take more air tickets for short haul trips! What is a better use of your time, a 10 hour bus ride for $25 or a 1 hour flight for $50?

Depends on why you're travelling. Ten hours of seeing the countries you're in might be more gratifying than two hours of being treated like a dangerous animal at an airport and one hour of biting your knees in a plane.

Re: Ask HN: Living overseas with a profitable online business

#85
post #43

Earlier quoted context omitted.

Absolutely don't buy a RTW ticket. Definitely go around the world, but do it by purchasing a single one-way ticket. Travel overland as much as you can and when you hit the end of a continent, buy another one-way ticket to the next. There's nothing worse than having a date on a calendar. It will mess up your trip over and over again, even if it's months in the future. Avoid dates at all costs. Get to the first place a…

Have you been travelling alone or with a friend / girlfriend / wife? I want to do this as well, but the biggest question for me seems to be who to go with or going alone (and then just trying to meet people everywhere)?

Initially, it was just me. Every once in a while I'd manage to convince a friend to fly out and tag along for a few weeks, thus putting one of those dreaded dates on the calendar, but in a good way. Along the way, I picked up a partner who was doing pretty much the same thing. We've scaled back the traveling a bit recently, but I did manage to drag her around South America for 7 months this year.

I'd recommend going by yourself if you have the choice. You just plain meet more people that way, and you don't run the risk of killing off a perfectly good friendship. On the road, you'll notice the same pattern a lot of times: two English girls who have been traveling together for a couple months and have clearly tired of each other's company but are too polite to suggest they go their separate ways. They're miserable, neither one getting to do what they really want, and forced to eat every meal together even though they've already exhausted all the conversation they could ever come up with. Sit down at their table and you'll instantly have two new friends.

Another benefit of traveling alone is that even as an introvert you'll periodically go into "emergency survival social mode" where you realize you haven't spoken to anybody in four days and you need to make some friends Right Now. And you will. It's as simple as walking up to any random gringo and asking "where are you from?"

Re: Ask HN: Living overseas with a profitable online business

#86
post #82

How do you guys deal with re-imaging a laptop in case the old one was lost? Do you keep an image online somewhere?

Try and have most data in the cloud (dropbox/live mesh/Amazon s3) and applications with cloud storage (google docs/basecamp/pivotal tracker).

I do carry a Windows 7 install disc and a 2.5" USB drive with all the various apps I need. (I code for .Net, so do require quite a few installed applications)

Total loss of a laptop while travelling would be a pain, but not insurmountable. Worse would be to lose the install media, but that's recoverable through MSDN, so given a day or two, would be up and running once more.

Would recommend having a virtual machine accessible from anywhere that you can fall back to if needed. That's saved my bacon a couple of times.

Re: Ask HN: Living overseas with a profitable online business

#88
post #41

Earlier quoted context omitted.

Absolutely don't buy a RTW ticket. Definitely go around the world, but do it by purchasing a single one-way ticket. Travel overland as much as you can and when you hit the end of a continent, buy another one-way ticket to the next. There's nothing worse than having a date on a calendar. It will mess up your trip over and over again, even if it's months in the future. Avoid dates at all costs. Get to the first place a…

RTW tickets are cost effective. You can usually pay some extra money to massage the dates, and it'll probably still be cheaper than buying tons of tickets (at least when I bought one... not sure how the prices have changes since)

Cost isn't what you're maximizing though. Sure, RTW ticket will run you $1500, whereas three one-way tickets will cost upwards of $2000, but compared to the $12k you'll spend all in, it's just not worth the constraint it places on you.

As an example, five years ago I started a trip that would start on the beach in Thailand, then go up through China and follow the Silk Road across to Turkey. 3 months in, I ended up detouring down to Australia to do a couple month's surfing with a girl who I'd eventually follow back to England and marry.

Had I booked, say, a flight from home from Istanbul ahead of time, I might not have wanted to blow it off and follow that girl who I'd only known for a month.

Traveling is all about freedom to do whatever you want with absolutely zero constraints. Keep that in mind before you buy a piece of paper that forces you to be anywhere at a given time. Even if that anywhere is "Asia" and the given time is "Sometime in the next six months". It's still a constraint, and it will still mess things up.

Re: Ask HN: Living overseas with a profitable online business

#89
post #62

Earlier quoted context omitted.

This won't affect you if it's literally just a short vacation or even a business trip[1]. However, even if primary residence is only de-facto (generally, more than half a year spent at that location) you will probably be on the hook for tax. So beware of that 27-week holiday or business trip. [1] exception: if you actually take payment in that location, e.g. selling stuff at a trade show, you need to register the bus…

So what's the situation if you spend 3 months in 4 different countries each?

Ask an accountant. I suspect you'll be more or less free to choose your primary residence as long as you actually maintain an address there. But seriously, with any of these things it's best to talk to someone who knows the ins and outs of the tax laws of the countries you're visiting.

Re: Ask HN: Living overseas with a profitable online business

#90
(Thankfully, I am not a lawyer, but I've lived outside the USA for all but 30 months from age 18 to 31. This is not legal advice.)

For US citizens, you need to be aware of a lot of additional regulations -- US citizens are taxed globally, and if you make more than the $6k or so minimum, you must file a return every year. You have a certain exemption (approximately $95k now) on your income, so if you make less than $95k per year, you don't owe any tax, but must still file.

If you are in a location which has its own taxation, you may need to pay, and then use a tax treaty with the US to deduct foreign taxes paid, avoiding double taxation.

Basically, if you have substantial income or assets, you should use an international tax attorney to handle these matters for you. Only an attorney has attorney-client privilege, and your average US tax preparer (or even worse, H+R Block or something) has no clue whatsoever. If you make There are lots of weird and non-intuitive special case rules built into the tax code, such as a restriction on "controlled foreign corporations", where >50% or so of the equity is owned by US persons, and are then subject to lots of extra US reporting requirements. This prevents a lot of the naive "keep all income in the corporation, pay yourself a trivial salary, expense all your personal expenses through the corporation" schemes, but also complicates legitimate foreign businesses owned by Americans. This is the kind of stuff you want the tax attorney for.

Right now I am personally stuck outside the US for the rest of 2010 due to taxes -- I worked in Iraq until August, making more than $95k, and thus it is a net savings for me of about $20k in taxes by remaining outside the US for the rest of the year, thus keeping my 330 days out of 365 out of the US, than it would be to return to the US. I have 6 days left in the US this year, which I might use for YC interview if I apply.

I plan to do my next startup in the US (maybe in tax-advantaged TX or WA vs. CA, but possibly just in the default of Palo Alto); taxes are annoying, but living outside the US is even more annoying.

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