I think this is usually because of a drug habit or too many ex wives.
That must be it - at least in LOTS of cases.
Did you know Nicholas Cage is on his 5th or 6th wife currently? Is he a glutton for punishment or something?
I feel like I should be making more of myself personally, but I can't bring myself to work in the current batshit insane climate.
I know there are Getbiggers who clear six figures a year - why not live like a pauper for a decade, invest in rentals, and just do that?
I still wonder why is Brian Shaw still competing. I guess his $1,000 a week food bill and gear bill prevented him from saving money. A drug habit, as you suggested. And Brian has an incredible will to win which I believe will eventually kill him.
As for Dennis Wolf - didn't he have a rich, elderly wife? And he made a bit of cash in his day. If he was smart with his money, he should be able to do ok.