10. Ben Lerer

Missed Funding in: Skillshare, Foursquare and Uber

Ben missed three great investments because he never trusted his guts. "In all the situations, I passed because I didn't trust my gut. I thought of reasons why not to do a deal rather than just trusting my intuition," says the co-founder of Thrillist.

11. Chris Dixon

Missed Funding in: Dropbox

Angel investor Chris Dixon would have been able to be a proud Dropbox investor only if he would have asked the founder Drew Houston. "Sometimes when people come to you for advice like that they are really hoping you will ask to invest and I didn’t. I’d have to say in all honesty if I were offered I probably would have passed," says the co-founder of Hunch.