Sure. Richard Branson has pictures taken of him waterskiing with a naked woman on his back. Steve Jobs, on the other hand, is an intensely private person.
For the record, Branson's equipment is for the much trendier kiteboarding, not wakeboarding. I say this because I'm sure photography has a coolness threshold before it's no longer plausible.
Richard Brandon photo results:
http://images.google.com/images?hl=en&client=safari&...
Steve Jobs photo results:
http://images.google.com/images?hl=en&client=safari&...
However I don't think the point of the original poster holds. Steve has said he's done LSD, for example.