Success in Silicon Valley, most would agree, is more merit-driven than almost any other place in the world. It doesn't matter how old you are, what sex you are, what politics you support or what color you are. If your idea rocks and you can execute, you can change the world and/or get really, stinking rich.
That first company I started made a lot of money for the venture capitalists - nearly $30 million - but next to nothing for the founders. The companies I started after that varied between failures and mediocre successes. But at no point did I ever consider getting a 'real job.' That felt like a black and white world, and I wanted Technicolor.
Generally speaking, experience counts for something. So you'd expect entrepreneurs who've been through the ups and downs of a tech startup to have an advantage over the newcomers. Or at least have an equal chance at success. But in fact the opposite may be true. A number of venture capitalists I've spoken with have said that too many "old guard" entrepreneurs are not being bold enough in their business decisions, and it's hurting their startups.
Leaving America means renouncing your citizenship, moving out of the country and leaving family and friends behind. You can retain your citizenship if you like, but you'll still be away from loved ones and still be paying taxes. You lose all the good stuff about America and have to keep all the bad stuff.