John Sculley: Apple

During his tenure as Apple CEO from 1983 to 1993, John Sculley committed the ultimate business fail — he fired Steve Jobs in 1985, news that caused the company’s stock prices to plummet to less than $2 per share from more than $5 per share in 1984. Sculley was forced out of the company in 1993 over a dispute with the board about licensing Macintosh software to other computer makers.

Sculley was opposed to the licensing idea, which the company went ahead with — and which was the first thing Jobs canceled upon his return. In a February 2015 interview with CNN tech, Sculley revealed he regrets not hiring Jobs back because he believes this would have saved Apple from near bankruptcy in the late 1990s.