MARK CUBAN

For some people, it isn’t about showing off just how wealthy they are. There are also those who purchase planes because it is a necessity. Just take Mark Cuban’s Boeing 767 and Gulfstream 500 for example. That’s $40 million he dropped on both planes, but he’ll be able to easily earn that back.

He is one of the most prolific entrepreneurs and probably spends the same amount on all the business flights he takes every single year. Besides, it isn’t just for his own use—the Boeing 767 also serves as transport for his own basketball team, the Dallas Mavericks. He wouldn’t be a good businessman if he didn’t make wise investments, right?