It's hard to overstate how unlikely Twitter creator Jack Dorsey's success as a tech founder seemed at one time. The college dropout joined a company that went down in the dot-com bust in the late 1990s. After living in a handful of cities, he returned to his St. Louis hometown feeling like a failure. There, at age 26, he studied botanical illustration, according to a 2013 profile of Dorsey in the New Yorker. Finally, after a babysitting stint, Dorsey re-entered the tech world as a programmer. So how did the man, who's been described as a polymath, become the CEO of credit card processing company Square? The journey wasn't exactly a linear one, and it has led critics to believe that Dorsey's tendency to juggle a wide variety of interests has hurt his focus. On the other hand, many admirers agree that it has led to a wild and prolific imagination. Check out the timeline below to see how Dorsey's experiences have added up to two successful companies.