7. Joe Jackson

Missed: Facebook

He chose an established company over an unstable start up. Sounds like a smart choice but he ended up losing millions.  That is the volatile world of technology today. Mark Zuckerberg had invited Jackson to his house in Palo Alto for the summer. Jackson chose an internship at J.P. Morgan Chase.

“I completely missed the boat," he tells Bloomberg BusinessWeek. "I wasn’t thinking about it as ‘this could be my chance to be rich and famous.' It was more like, ‘This is going to Palo Alto and living in a house with a bunch of kids and programming for a startup that may not go anywhere."