What Rob didn't tell us is what his regular income was when he lost $250,000 gambling as an "AP." If he was making less than $100,000 a year (which he probably was given when this happened and the corporate job he had) then he was really betting over his head. If on the other hand he was making $200,000 a year then losing $250,000 over a period of time gambling (we don't know what that period was, do we?) then it might not be unusual.

Look, I know business people who lose $100,000 per weekend and don't even wince because they earn so much money. I'm not one of them, however.