If Mark Zuckerberg projects his baller status by dressing up like a college dropout (he is one, after all), Jack Dorsey takes the opposite route-- preferring to match his daunting net worth with an equally formidable uniform. The founder of both Twitter and Square (he's executive chairman and head of product at the former, CEO of the latter), has a reputation for rocking black Prada suits and slim dark ties. Dorsey is perhaps the Valley's most eligible bachelor, and counts the principle ballerina of the San Francisco Ballet Company among his exes. As one might expect of a man with such a resume, the 34-year-old magnate is no stranger to the glamorous life-- he's been known to pal around with stars like Ashton Kutcher and Alyssa Milano.