I've never known anyone with true "family money". Probably the richest person I knew was a girl I worked with who's father owned a big metal processing company. He paid for 100% of all his kids college and room and board.
Once they graduated he gave them enough to purchase a house, he paid for all the "un-fun" stuff like car insurance, cars, maintenance, phone bills, etc.. They used whatever they made in their jobs for vacations, nice clothes and all the "extras" -the fun stuff. Also each child was on the board of directors of the company and he paid them some annual salary to supplement whatever they made from their jobs.
Again, they started out on third base. They were as established at 25 as most 50 year olds that had to do it on their own.
