Don't worry too much about it. Plans are overrated. I've never made a plan in my life and everything has worked out so far. Pretty anecdotal and vague, I know, but I'm just saying it is possible.
If I were in your position I might consider starting up a freelancing business, getting a few steady clients, then coming to the US for "pleasure". Line up a place to stay where nobody is going to ask for a green card; if any group will put you up, it'll be hackers.
After that... who knows! A really vague, partially illegal, mostly crazy plan. I like it.
Edit: And if you make it to Boston, let me know. We've got a spare room you could crash in for a bit I'm sure (see profile for info).
Jumping continents is a pain in the ass though. I did it when I was 21 (seemingly permanently, as 7 years later I'm still in Europe) ... it took months to pull it off, get everything lined up and so on. Especially if you're in the startup game you don't want to risk falling foul of the US immigration authorities and being denied entry in the future.
My take on things: If one wants to do some crazy traveling improvising along the way kicking back and hacking as you feel inspired, by all means! But why the heck would you want to do that in the US?
If you want to get into American startup culture, well, then you should focus on what you need to get in legally and stay there. College degree, convenience marriage, student visa...
Thats all I've been doing pretty much, I used to do freelance bits from when I was about 14 (which seems crazy now), so I've been sending some mails and have stuff trickling through - it seems like the best bet for someone in my position.
I'll definitely bear the room offer in mind. Thanks : )
If I were in your position I might consider starting up a freelancing business, getting a few steady clients, then coming to the US for "pleasure". Line up a place to stay where nobody is going to ask for a green card; if any group will put you up, it'll be hackers.
After that... who knows! A really vague, partially illegal, mostly crazy plan. I like it.
Edit: And if you make it to Boston, let me know. We've got a spare room you could crash in for a bit I'm sure (see profile for info).