[bloomca]

He discussed the whole plan with his family, and they agreed on it. Secondly, he studied in Harvard, so his family had at least decent amount of money by default.

And then, the thing is that family who was struggling the whole time, won't agree on dropping the best university with wonderful perspectives for some kind of crazy (at the moment it was very "crazy").

People are not "just risky" by default, they are influenced heavily by their life, and as someone mentioned here already, a lot of rich guys came from pretty decent living families, who can afford to fallback if something. For instance, a lot of world travellers, who try to live differently, actually have some passive income, property of just loads of cash, just in case something will go wrong.