1) Ran a successful professional online poker playing business, actually hired employees and trained them to predictably win.
2) Was one of the main characters in the book The Game (yes, that PUA one).
3) Did polyphasic sleep experiments in earnest (was it a couple months or so?).
4) Had a giant inflatable outdoor pool inside his house, taking up his entire livingroom.
5) Sold all his belongings, including said house, and travelled the world for a year with almost nothing... probably in 2k8 or so before such an idea became more commonplace.
There's probably some much cooler stuff I'm forgetting, but hey it makes perfect sense he'd be part of an island buying crew.