In 1971, when the great boxer Muhammad Ali was still undefeated, U.S. basketball star Wilt Chamberlain suggested publicly that he stood a chance beating Ali in the boxing ring. Promoters scrambled to organize a fight that Ali considered a joke. Whenever the ultraconfident Ali walked into a room with the towering Chamberlain within earshot, he would cup his hands and holler through them: “Timber-r-r-r-r!”
While Chamberlain felt that one lucky punch could knock Ali out and that he stood a decent chance in a fight, the rest of the sporting world knew better. Chamberlain's odds of winning were ridiculously low, and his bravado could only lead to significant pain for the great basketball player.
As legend has it, Ali's “Timber-r-r-r-r!” taunts eventually rattled Chamberlain's nerves to put a stop to the pending fight.1
Most people don't like losing, and for that reason there are certain things most of us won't do. If we're smart (sorry Wilt) we won't bet a professional boxer that we can beat him or her in the ring. We won't bet a prosecuting lawyer that we can defend ourselves in a court of law and win. We won't put our money down on the odds of beating a chess master at chess.
But would we dare challenge a professional financial adviser in a long-term investing contest? Common sense initially suggests that we shouldn't. However, this may be the only exception to the rule of challenging someone in their given profession—and beating them easily. ...