Bootstrapping overseas as an American

Try this link for some pointers: http://www.forbes.com/sites/joshsteimle/2013/07/12/how-i-ope...

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.'

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."

Yes. FEI is the IRS's bone to US citizens residing outside the US (in most countries, you only pay taxes if you're resident, citizen or not, the US is one of the few where you're taxed even when residing in an other country)

Been living and working in HK for almost 10 years - currently all visa-ed up and legal, but haven't necessarily always been...

There are persistent stories of people who've been living here for years doing regular visa runs, but oddly they mostly seem to be stories, not direct experiences. There are also stories of people who got 'caught', in that the immigration officials decided they'd done too many runs and couldn't explain how they were living in HK without working, and were given 2 weeks to clear up and move out. It's a risk...

With a UK passport you'd get 180 days of visa-free stay per entry, with most other 'developed-world' passports you'd get 90 days. The actual rules on what you can do during that stay are quite strict - attending meetings, negotiating/signing contracts, etc. is allowed, but most other work isn't - to the extent that technically you're not even allowed to do voluntary work. That said, nobody is going to bother you if you're here for a few months and happen to be working for a remote client/employer at home or in a coffee shop. It's the visa runs which are the danger, since that's when they can pick you up. May not be a nice thing to say, but being white does help quite a lot.

It's easier to be here as a resident, legally. You get (almost-)free access to government healthcare, and things like banking are much easier, plus of course you don't have that looking-over-your-shoulder feeling.

One standard piece of advice, which definitely doesn't fit everyone but might be worth considering - assuming you and the GF are a heterosexual couple, a civil marriage is relatively simple in HK, and assuming she is working and/or a resident in her own right, that would get you a visa as a dependent. HK doesn't recognise non-heterosexual relationships in any useful way...

An alternative might be Taiwan, maybe not for you, but for others seeking 'Asia' - I do know a Brit who's been living there for years doing visa runs while writing code for people mostly in the UK, and it seems to work for him and his drunken bum lifestyle :)