Some of my college classmates went down this route, and while the numbers can theoretically work out (these are uber-smart math/science/engineering folks), I've never seen a single person exit successfully from this game and then unicorn it. The main reason seems to be that they can't fight off the inevitable lifestyle inflation that comes with being in such a social circle. The last I heard from one guy, he was paying almost $10,000 a month to maintain two apartments in Manhattan ...