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Growing up I went to school with two kids that were from very well off families. I grew up in a small town so it was no secret that their families had a lot of cash. One of the kids was an absolute dick. His grandpa made the money by buying up a huge chunk of the land around the town when it first started to grow. Now much of what is the center of town is on his land and it is leased out to the building owners. The grandpa was no longer alive when I was in high school so this kids dad ran it and he made a habit of raising the rent all the time and suing people on a regular basis. His son, who was a grade below me, walked around like he owned the town and often referred to it as "his town."
The other kid was actually pretty cool. His dad made his money with a trucking and logging company. In high school this kid did drive a 70's era Corvette, but he was actually a good guy. My understanding is that when he got out of school he started working for his dad on the bottom rung. His dad wanted him to learn the business from the ground up.
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