I'm currently in H-1B status and work for a top tier hedge fund. I recently resigned because I decided it was time to go full on with my own company, and even though I have lived here for 2 years, paid my share of taxes, and have enough saved up to support myself for at least 1.5 to 2 years, if I don't succeed/raise money to sponsor my own H1B in the next few months (or take a new job) there's a chance I will have to go home.
Oh, and even getting a chance at getting those few months, is dependent on the USCIS approving my change in status from a specialist worker to a "tourist."
There's just so little room for error as an immigrant, but the fact that you can make lots of mistakes is one of the things that makes the US so awesome for gutsy Americans.
Immigration is a messed up thing and it's just sad to see someone throw a citizenship away that so many people would fight like crazy for. I doubt he would have gotten that first chance to make it big anywhere else.