I don't know if this qualifies as "rich", but I'll tell it anyway.
Back in the 60's/70's, my grandfather entered the navy and was trained on computers. He had a natural knack for it and developed an excellent skillset that put him in demand once he entered the private sector, especially given the context of the times. This is back when Apple and Microsoft didn't even exist yet and/or were just getting started. Guys like my grandfather were a bit of a novelty, and you could make some serious cash. So by the early 80's, he had managed to save up enough money to put himself well into the 7-figures.
Well my uncles were in their late teens by this point, and my grandfather wanted to 'invest' the money in something that would help benefit them for years. So he decided he wanted to start a business. The idea was that my uncles could work at the company, my grandfather would earn his investment back over time, and eventually my grandfather would retire comfortably and my uncles would take over the business and have an income source for the rest of their lives. Nice idea.
So he gets convinced that he should buy a regional auto parts franchise. The business was doing well and it would allow them to set up where they currently lived. Only one problem - my grandfather had no clue how to run a business, and no one in the family had any real experience with auto parts or sales.
My grandfather went bankrupt within a couple years. It's all gone. Fast-forward about 6 years, and my grandfather, grandmother and both my uncles are living with my mom and dad and me. Oye.
But it gets worse. The guy who recommended to my grandfather that he should buy into the auto parts franchise? My dad. My dad knew of the business and knew a lot of people involved with it, so he suggested it to my grandfather.
Fortunately, there don't appear to be any hard feelings - at least I've never noticed any. We joke about it now, but it completely changed the direction for my entire family. My parents struggled for years (I'm 31 now - they only just a few years ago finally paid off credit card debt that they had initially incurred when I was a kid). My one uncle never really got his life together and is a bit of a loser to this day. My other uncle started a business and does OK for himself - enough to live a comfortable middle class life.
My grandparents got the worst of it. Both in their 70's and they only just recently were able to stop working. My grandfather was still doing a midnight paper delivery route as recently as a few years ago, and my grandmother was cleaning houses until that same time too.