A relative married into a wealthy family. It's been fascinating to watch the money flow down the generations. A synopsis:
Generation 1: the founder. Don't know much about him except he must have been smart, worked hard, and been a bit lucky. The products from the company he founded can still be found in your local store.
Generation 2: the son of the founder. Mildly cognitively impaired due to a teenage accident. Didn't stop him from rising to become president of the company (nepotism at work, I suppose). A nasty confrontation on the founder's deathbed led him to sell the company out from under his son. The family was showered with a huge amount of money as a consequence of the sale but lost its reliable large source of corporate income. From that point on, it was all coasting on the already existing substantial wealth.
Generation 3 (my generation): the grandchildren of the founder. All of them screwed up in various ways, with (excessive) family money as a (possibly) major contributor.
Generation 4: great-grandchildren of the founder. The family money hasn't arrived yet for some of them. Some of them are going to (essentially) be disinherited because the corporate trustee of the generation-skipping trusts created by generation 2 has indicated that it's OK for generation 3 to grab the money, which is clearly contrary to the generation 2's intention. Generation 4 could sue, I suppose, but I doubt that this is going to happen. I just watch from the sidelines in amazement.
Generation 5: great-great-grandchild of the founder (just arrived). You would never know that the parents come from a wealthy family based on how they are living now. Will any of the family money ever arrive to help this child? Who knows?
My take: the best way to learn the value of money is to not have any. I started my adult independent life with a mere $20k in the bank (no debt) and some highly marketable college degrees. Many of today's kids seem to start out with quite a bit less.