#9 Jerry Yang shooed away Microsoft's $44 billion

Jerry Yang is the co-founder and former CEO of Yahoo. As CEO from June 2007 to January 2009, he infamously turned down a $31-a-share, $44.6 billion offer from Microsoft in 2009, in a bid to take over Yahoo. 

Many shareholders were unhappy and wanted Yahoo to sell. All the drama sent the company into a downward spiral for years. The Wall Street Journal, soon after this fiasco, reported that Jerry Yang would step down as CEO.

Only now, with former Google executive Marissa Mayer in charge, is Yahoo is recuperating with its stock trading in the mid-20s.

#8 Ronald Wayne could be worth $40 billion today

Ronald Wayne, Apple's third cofounder, sold his 10 percent stake in Apple for $800 two weeks after launch. He later got $1,500 for renouncing all claims to ownership.

If he had kept it, it would be worth about $40 billion today.

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