Just because you know or heard of some rich what makes you think if you go back you would even make a tenth of what they make? Given you talk so much about smart, rich, and educated people your post contains a lot of grammatical and spelling errors which prompted me to ask this question.
lets say he really did live in a shit shack. so the heck what. that makes you better than him? if he is posting with evil intent call him out for that if he writing stupid shit tell so... but living in a one bedroom. wtf?
lets say you are really successful and you earned it as opposed to getting it from family friends or your wife. You are probably smart or charismatic made good decisions and worked hard... awesome... but there may also be some great timing involved too.
I went to my 20th reunion at greenwich high school around the turn of the century. I lot of my friends had worked on wall street and been phased out already. Some still had big jobs... or were part owners in specialist seats on the NYSE or the brokers on the floor. over time I heard from other friends they were almost all out of the industry. At the time only one or two had houses in Greenwich. Most were up north a bit.
My brother is six year younger than me. A handful of his friends had big jobs at hedge funds with estates in Greenwich and millions to burn.
My brothers friends were not smarter than my friends. In fact I knew some really smart guys... by a long shot over my brothers friends.
By the way this is not sour grapes or an excuse. I choose to move to San Diego and go to school out here. Once I started surfing I would not have gone back for 1 million a year back then. I might now... but that is another story as I don't surf anymore and I have a wife and kids. But, I might not either.