I caddied golf tournaments back in college for some $$$ and met some cool people. One guy comes to mind, Paul. Older guy, foreign background, but very nice and polite. Caddied a particular tournament two years in a row, and was in his group both years.
The first year talked about what he did and found he owned 20something car dealerships. Had a single engine Piper plane he used for short trips. The following year he had sold all his dealerships and got into commercial real estate and still had his Piper, but also bought a Cessna Citation (don't remember exactly which model) for $7M. His justification for it was he was tired of the airlines - completely agree with that. Just hangar and maintenance alone was $400k a year.
Most everyone at the matches were in a good mood since they're all out to have fun golfing, but some were even dicks then. Depending on who it was I'd get tipped $20 each at a minimum, but Paul would whip out $100. The second year he handed me a $100 bill, looked at his wallet, then gave me another $100 bill. Cheap ass (Toranto Blue Jay) Joe Carter was the only person to ever stiff me - and that was after he'd been bragging about how much money he won at the casino the night before.
Out of HS I worked at the San Jose Jet Center refueling private planes and jets and met a lot of people. CEOs, owner of the A's, 49ers, and whatever the others did. Some were pr!cks and some were really cool.
Talked to the pilots one day when the A's daughter was flying up to Tahoe with her husband, think it took them 21 minutes to get there, only because of the 250knot speed limit under 10k feet or it would have been 17 minutes so they said. Must be nice.
