Kevin O'Leary, a star of ABC's "Shark Tank," is certainly qualified to dish out entrepreneurial advice. With the show in its tenth season, he's counseled hundreds of aspiring and established entrepreneurs.

He's also a wildly successful entrepreneur in his own right. In 1986, O'Leary started Softkey Software Products, which was later re-named The Learning Company, in his basement with no cash. He ultimately grew Softkey into a huge operation and, along with his nine other co-founders, sold it for $4.2 billion to the Mattel Toy Company in 1999.