The first question is why the fuck does Bob have four houses, and the second would be how is it that people like Bob are easily able to become billionaires only since the Reagan administration? Certainly Bob did not actually work for this money, all those shares, for all four of those houses. That amount of wealth is far beyond what any reasonably productive person could possibly earn. The only possibilities for him to have all of that is either through nepotism, inheritance, or corruption. If he is gaining that wealth by being given stock options and then borrowing money against those stock options and then using tax write-offs to not pay that money back, then Bob is stealing from his company, the country, and his employees.