Dorsey once had blue hair and played music in the street. For a while he went around dressing like Steve Jobs. Then he was obsessed with Japanese culture. Then he was going to become a fashion designer. Then he reportedly wanted to be mayor of New York. After being pushed out of Twitter he started a payment company called Square, which raised $590 million in venture funding and in November 2015 successfully sold shares to the public, despite having lost nearly $500 million—half a billion dollars!—in just four years. In 2015, Dorsey became CEO of Twitter again, so he now runs two companies.