I'll save the story about my stupid idiot moron nephew for later....
Its later!!! I'm ready for it!!!
Okay, the dumb nephew.
He majors in Fraternity for 4 years at U of MD and parents (wisely) stop paying after that. He gets a job at the university and later graduates with a degree in marketing because employees can take two classes a semester for free. So at least he was smart about that, but I suspect he did it so he could stay involved with fraternity life. He and his wife were later houseparents at a sorority. For about ten years.
So he has his marketing job at UMD, until the position is eliminated and he is now jobless. I later found out that during this time he's lost two houses to foreclosure, been kicked out of rentals because he didn't pay the rent, and has been sued for back taxes five times by the state for nonpayment of those.
During this time he did have a steady income, there was no reason for it.
Did he think these bills were just going to go away?
During the housing boom he gets a job selling real estate with (you guessed it) a former fraternity brother and for a while does very well, selling something like $4 million in oceanfront condos in a year. Buys the Lincoln Navigator and some other toys, nice restaurant meals, etc. but he doesn't save a nickel. Oh, and he doesn't takes care of his diabetes, he does like his beer. Now, as he puts it, he "gets a 10% discount on a pedicure" having lost a toe to gangrene. He may also go blind.
We all know how this turns out. Oceanfront condos stopped selling. Now he and his wife are bagging groceries at a grocery store.
The guy is great at getting along with other people and to talk to him he seems reasonably bright and is very knowledgeable about some things. But apparently he can't plan past next Tuesday.