4. Sahil Lavingia

Missed: Instagram

He is better known as the 19 year old college dropout who has generated $8 million for his startup Gumroad. He was earlier with Pintrest which he had to leave at a very inconvenient time, a month short of completing one year with them. He had to let go of his stock options thus losing a considerable amount.

We can only hope that the creative designer will make up the lost money with his new venture. Good luck to Gumroad.