Jim has one hell of a resume, from owning a wine store, to holding an MBA from the University of Michigan, a World Poker Tour champion, and the above mentioned Marijuana Dispensing. If nothing else he is ambitious and adaptable.
I get a sense he will be scheming and trying to lay low while influencing the leaders. I.E. the Marty strategy. I definitley think he will go far and is almost a lock to make it at least as far as the jury stage. Even if he ends up on an alliance who is on the outs, I sense he will figure out some way to survive to fight another day.
He admits to not being the smartest or the best athlete, so I think if he goes to Redemption Island he will be gone the following week. But I sense he will do a good job of not letting that happen.
He is definitley one to watch, and based on first impressions seems like a good candidate to walk away with the whole thing.