H. Ross Perot Jr. (yes, the son of Ross Perot) piloted the first ever helicopter round the world flight.
On September 1, 1982, H. Ross Perot Jr. and Jay Coburn left Fort Worth, Texas, on a Bell 206 L-1 Long Ranger II and returned 28 days later. They flew on average of eight and a half hours a day, refueled 56 times and flew over 26 countries. (Source)
He's your classic nerd-done-well, and did the clever thing: retired early and then starting spending money in interesting ways: