Do you truly imagine this means he has to live on a tiny island? With billions of dollars?

The man could easily maintain homes in wonderful places around the world and do whatever he wants with his life in any of them.

He's not going to regret this for even a minute.

He wont have to live in Singapore forever but that appears to be his plan at the moment. He's been there for quite awhile and seems to be loving it. It is a great place to be young, rich and good-looking. It's going to get old if he tries doing it for the rest of his life though. 10, 15, 20 years down the road is where that regret will kick in.

Sure there are plenty of other great places to live than the United States - but his career trajectory seems to be in tech. Thats where he is continuing to invest and put his time. All roads in that arena lead to California - a place he just voluntarily gave up the right to ever reside, work and do business in.

There are places other than California to do things in tech, believe it or not.

Facebook wasn't even founded in California, for example.

They re-located to California and are still based there today. What does that tell you about the point you are attempting to make?

this has got to be one of the most insular things I've seen on hn in a while. sure, the us is a wonderful place in which to "do something with your life"; in fact it's where I've currently chosen to do something with mine, so I'm certainly not bashing it. but the world is full of places in which billions of people are doing fascinating things with their lives; to say that someone who made the considered decision to give up citizenship is going to regret it because only by coming back here can he accomplish stuff is deeply myopic.

And yet sadly, most Americans seem to have this myopic view that the USA is the be-all and end-all of everything good, sacred, and worthy. Welcome to America

I find this to be extremely interesting.

When people in America have a hard time getting a house loan, or have shitty health care, or are living on food stamps, they simply say "Well, at least we are better off than everyone else".

THAT is extremely scary.

For the vast majority of the world's population, not being in the United States hasn't been a barrier to doing something with their lives.

Or like most people who get US visas, they'll just buy their way back into the US.

You might enjoy the fantastic book "Emergency" by Neil Strauss. It's non-fiction and deals somewhat with the "5 Flag" theory.

The US has a ton of problems. It's not a great place to live IMHO.

Not at all, He can still go to the US as a visitor when eer he wants (he just needs a visa), and even long term by applying to be a resident alien.

The IRS and State Department (who issues Visas) are well aware of the hack you are describing and the system is already setup to prevent people from doing that.

I was an expat for close to 7 years, have friends who renounced and thought long and hard about doing so myself. I can say with great conviction that long term, in my educated opinion, it isn't worth it.

I don't think he's going to miss anything US :-)

Being rich in Singapore is not exactly limiting.

There are plenty of good, useful, and interesting places in the world outside of the US.

Singapore in not an island.

It's a state made up of 60+ islands. The largest is often called "Singapore Island":

http://en.wikipedia.org/wiki/Singapore#Geography

http://en.wikipedia.org/wiki/Geography_of_Singapore

So it's not an island

Singapore is an island