The Times has a story on the Rubio family finances today.
Slate notes that the Rubios were doing what every striving upwardly mobile person was supposed to do in 2005, buy real estate. They were fortunate--they lost money, but didn't have to hit the bankruptcy court.
I'd cut him a break--IMHO learning to deal with money is a multi-generational thing. I've been reasonably successful by learning from my father's (over conservative) and grandfather's (a sucker) mistakes.