Bloomberg columnist Graef Crystal points out that Apple CEO Steve Jobs made a costly mistake by trading in his options too soon. “Jobs in January 2000 received the largest option grant in history: 20 million shares with a present value that I estimated were US$471 million,” writes Crystal. “The option promptly sank under water, as did a second option covering another 7.5 million shares, which was granted in October 2001. Jobs then took an offer in March 2003 to turn in all 27.5 million shares for five million free shares then worth about $75 million. As of the markets close on Nov. 22, those free shares had a value of $307 million. Had Jobs kept his 27.5 million option shares, they would have contained, again as of the close on Nov. 22, paper profits of $678 million. Bad move, Steve. Some people may perceive you as arrogant, but based on your decision, you really underestimated yourself.”