My grandfather on my dad's side had ~16 kids, and his father had 20 kids.

I don't know much about my great-great-grandfather but I believe he was a businessman that moved to Hong Kong to start a business. It eventually grew and he was set to hand it down to his firstborn son but this was during one of the opium crises at the time so he passed it onto my great-grandfather who was like one of the only sons who didn't screw up. Great-grandfather carried on the business and a majority of his sons fell to alcoholism, prostitution, opium, or other "sins" so it went to my grandfather who was the 6th born son or something.

When my grandfather died his will allowed for all his buildings to be sold and the inheritance would be divided up so his sons would get the majority and his daughters would only get 10% of what the men got which caused some family feuds.

My dad's mom also came from a relatively wealthy family but her dad had several wives and once he died all the branches of the family split and fought each other for money.