I'd actually argue that the debt thing isn't a sign of poverty, since from what I recall from his talks on Youtube, he is mostly just abusing the absolute shit out of the US tax system, and the fact that he has a decent sized cash-flow from all his books, rental properties and speaking gigs. The fact that he loans a whole lot of money (which isn't taxed, because loans aren't taxable) and uses it to fund whatever dumb shit he wants to spend money on, is in fact the same thing that gave Donald Trump the infamous 0-dollar tax return. Taxes are only paid on income when you "earn" it, and since all of his money is techinically other people's money, he doesn't have to pay taxes on it when it gets transferred to him. It also means that he is exceptionally vulnerable to anything that might shake this cash-flow, since he is leveraged out the wazoo, but up until it goes horribly wrong, he is going to be just fine.