Jim is a very bright individual, who thinks very logically when it comes to stocks.
He doesn't have a good "feel" for the markets, and as result he doesn't make much money. His hedge fund rode the tide of rising internet stocks, which he was able to guage because invesment banks were bidding him ever higher prices for the Street.com, so he could sense, first hand, how frothy the buyers were. The hedge fund went bust twice, and his wife bailed it out with "bet the house" trades.
Never, ever buy his ideas on the opening the following day. Check the charts, do the work, and then, when they come back down (they always do) take a look. One of Jim's short comings is that he is very undisciplined. Chases sectors and stocks, adds to bad positions, and generally is not a structured or diciplined professional.
Jim is very entertaining, but he is not a world class investment guru by any stretch of the imagination. Fun to watch; good with ideas; not much of a track record at making people money.