I think Ballmer at number one makes the list. Anybody trying to make a statement at any point in time about which tech products will be relevant in the future will be hard-pressed to hit better than 50%.
Microsoft repeatedly throws good money after bad, chasing the latest fad but never getting any of them completely right or, more importantly, creating any game-changing innovations to speak of. They saw Sony making the PS3 and decided they had to build a competing product and threw away billions in the process. They saw Google, and assumed they needed to build the same search engine to remain relevant. I can't believe that Ballmer has managed to stick around as long as he has, but if I were a Microsoft employee or shareholder, I would want his head to roll.
Microsoft repeatedly throws good money after bad, chasing the latest fad but never getting any of them completely right or, more importantly, creating any game-changing innovations to speak of. They saw Sony making the PS3 and decided they had to build a competing product and threw away billions in the process. They saw Google, and assumed they needed to build the same search engine to remain relevant. I can't believe that Ballmer has managed to stick around as long as he has, but if I were a Microsoft employee or shareholder, I would want his head to roll.