With the dot-com boom of the late '90s and the app revolution of the late 2000s, the old American Dream of working your way up to a position as a doctor, lawyer or small business owner has gradually given way to something more geeky. Overworked college students and cubicle dwellers today spend their downtime dreaming of founding an Internet startup or building an app on nights and weekends and then watching it balloon into the next Facebook or Twitter.

Of course, as any pirate of Silicon Valley can tell you, the path to tech world glory is as perilous as the shark-infested waters of Wall Street. But there are a handful of fabled leaders who really do make it look easy-- and fun-- keeping the dream alive in the process. While dating prima ballerinas, owning championship sports teams, and/or making business cards with expletives printed on them in bold, these five industry big wigs invent new ways to make green and keep the rest of us green with envy.