Image via Complex Original
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.
5. Mark Zuckerberg
This 27-year-old billionaire takes a lot of flack for the real and perceived sins of his little dorm-room project called Facebook, but he doesn't let that get in the way of living a charmed lifestyle. Zuckerberg re-invented the tech entrepreneur's dress code in his own hyper-casual image, showing up on a day-to-day basis in flip-flops and a hoodie, and taking fuck-you meetings with would-be business partners clad in his favorite pajama bottoms. As if the attire didn't make things clear enough, the supremely self-confident young executive famously telegraphed his privileged status on a set of custom business cards. They read: "I'm the CEO, bitch."
4. Jack Dorsey
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.
3. Elon Musk
Elon Musk gets points for being creative with his cash. The 40-year-old South Africa native took the millions he made from selling PayPal to eBay and used it to start the two coolest companies he could think of. One, Tesla Motors, has been hailed as the future of American auto-manufacturing and single-handedly transformed the electric car into an object of lust. The other, SpaceX, landed a $1.6 billion grant from NASA in 2008 and could be the company that finally makes space travel a practical reality. Musk's raconteur entrepreneurship is why he is one of two men on this list to have served as the real-world inspiration for Tony Stark as depicted in the Iron Man movies. Swag.
2. Larry Ellison
The other Iron Man is perhaps the best example of excessively good living. Larry Ellison, co-founder and CEO of Oracle, is known for spending as much time with his Yachts as he does in the office. Ellison, 66, is owner of the American Cup-winning BMW Oracle racing team, and at one time counted the sixth largest yacht in the world among his fleet. But it's not just sea-faring vehicles that catch his eye, the Oracle boss rolls around town in some of the flashiest rides on four wheels, including the McLaren F1, Audi R8 and Lexus LFA. And when supercars just aren't fast enough, Ellison simply boards one of his many private jets. He is a licensed pilot.
The veteran tycoon is the fifth richest man in the world, with a net worth of nearly $40 billion. He rests his bones at a number of high priced homes, including a California mansion with a 2.3 acre man-made lake valued at an estimated $70 million. All that from selling the world's most boring business software.
1. Mark Cuban
Mark Cuban just won the world basketball championship. Well, actually it was Dirk Nowitsky and the Dallas Mavericks, but the way Cuban celebrated he might as well have been on the court. And who can blaim him? The guy loves basketball, and with the billions he made selling Broadcast.com to Yahoo! just before the bubble burst, he helped build the Mavericks into a national force. These days, Cuban is busy getting his cable channel HDNet off the ground; that is, of course, when he's not cussing out rival teams or making cameos on Entourage.
