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This reminds me of Brian Lent. He sort of missed out on both Yahoo and Google. http://blogoscoped.com/archive/2008-01-22-n20.html. Edit: some choice quotes.

"When Filo asked Lent if he would like to join Yahoo! as employee No. 1, in order to keep the founders on their toes with his skepticism, he laughed. 'You couldn’t pay me enough money to work for a company called Yahoo!' he recalls saying at the time."

"In early 1996, Lent explains, “We all said, ’There will never be another Yahoo!’”"




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