When you seem him skate on video, it looks smooth as fuck. When he skates in person its so much smoother.
I randomly saw him on BART in SF after he was done as a pro. Some friends and I had just finished skating and had our boards and a conversation started.
Basically he said that the grind of pro skating wasn't worth it, and he was over the game. I would bet he had options, but just didn't feel like dealing with it.