My dh's family used to have a business which was set up by his great grandfather. It passed down the male line to his dad, who made a decent job out of it, but other factors meant it wasn't as profitable as it was. He warned dh off going into the business. He sold it off as he didn't have a pension and so needed something to live off. Both his parents are still alive thankfully. They live a very nice life, 6 bed detached, daily cleaners, trips all over the world etc.
Each generation going back in his family, left/gave a very nice sum of money to their son to set them up in life. Enough to buy a house and to put the kids through boarding school. But dh's parents haven't done that, and are seemingly spending the dosh instead.