I don't think its a matter of "hurting for cash." Its the thought that you could lose it all just as easily as gaining it all (or actually much, much easier). And as you get older and accumulate responsibilities, the overhead of families, good schools, retirement, all weigh on you making that thought all the more horrific.

Entrepreneurs are probably much more vulnerable to these kinds of worries, because that's what they worried about (losing it all) on the way up.