I like to think he was a skydiver pulling an elaborate version of 'Hey, hold my beer a sec. In fact, I might be gone a couple days, can you feed my dog?' He was special forces in Vietnam, an experience that left him a bit... eccentric. He jumped El Cap in the 60's and nobody knew about it. He used the money to rent a house by the beach, chase girls, party like a rock star, and skydive his butt off. His main goal in life was to have more fun than anyone else on the planet, but be low-key about it. He liked the fact that very few people had the slightest idea who he was.
That's what I like to think. But I might be biased.