Theory: Count Olaf is, in fact, an old Barney Stinson. He has become jealous of the lives his friends now lead, having also lost everything when he got back into gambling. He sets out to regain his fortune and he decides to do that by stealing the money from the very woman who scorned him. The characters he now becomes - Olaf, Stephano, Captain Sham, etc, are all characters he had come up with years before to impress women.