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10 CEOs With Serious Swag

Posted: 1/15/2014
It's apparent that not only pop stars like Justin Bieber love swag. Here is our list of 10 CEO's who not only run successful million dollar businesses or startups, but also live cool, trendy lifestyles or have unusual management styles.

1. Bill Gross - PIMCO

With a net worth of $2.3 billion, financial manager Bill Gross is undeniably an extremely successful businessman and CEO. His lifestyle and management style though are not perhaps typical for the average Wall Streeter. The trading floors of his company PIMCO are constantly silent, as Gross insists his employees and traders only communicate electronically, and he meets with his execs daily in a private, blinds-drawn room where the use of mobile phones are banned, in order to ensure full focus is on PIMCO and how to make money for their customers.

The eccentric entrepreneur's casual dress and informal attitude, along with many TV or public appearances has endeared himself to many, and if he is not working you might find him practicing yoga, collecting stamps, playing blackjack or relaxing in the $37 Beverly Hills million estate which he and his wife bought from Jennifer Aniston.

2. Larry Ellison – Oracle Corporation

Being the CEO and founder of a company selling boring business software doesn't guarantee a boring personality or lifestyle. In Oracle's case, it's quite the opposite. Founder Larry Ellison, one of the world's richest men with a personal worth of $41 billion, spends more time sailing than he does managing his businesses. If he's not out at sea he will probably be found driving around town in one of his many supercars, or flying one of his private jets (he's a qualified pilot too).

3. Jack Dorsey – Twitter and Square

Being executive chairman of Twitter and CEO of Square clearly gives Jack Dorsey ample time to pick out nice suits. The 36 year old has a reputation for donning smart Prada suits with skinny ties, and his single status perhaps makes him the most eligible bachelor in Silicon Valley.

4.  Elon Musk – SpaceX

With the millions made from selling Paypal to eBay, Elon Musk thought about the coolest possible companies someone could wish to start, and then did it himself by founding Tesla Motors and SpaceX. The former has been described as the future of American automobile manufacturing and the latter making waves in the Space industry, and after a huge financial grant from NASA could prove to be the first company to make commercial space travel a reality. Speaking about achieving his goals Musk proclaims: "Optimism, pessimism, f*** that; we're going to make it happen. As God as my bloody witness, I'm hell-bent on making it work." The character Tony Stark, from the Iron Man movies, was inspired partly by Elon Musk's lifestyle and entrepreneurship.

5. Michael O'Leary – RyanAir

With his aggressiveness towards his critics, Governments and Airport bosses, his abrupt attitude to customer service and his intense and unconventional methods of cost cutting, you could be forgiven for thinking RyanAir CEO Michael O'Leary is a little nuts. One thing which isn't debatable about O'Leary however is his track record. He was promoted to chief executive of RyanAir in 1994 and during his reign the company has continued the low-cost airline model started by Southwest Airlines, and has become the world's leading budget airline, making a net profit of €503 million in 2012.

6. Jim Deters – Galvanize

In 1998, Jim Deters arrived in Denver with a plan to start businesses and go snowboarding. He started two online content tech companies called Knowledge Arts and You@Web, the former of which managed a revenue of over $30 million and made in into the top 20 fastest growing companies list on Inc.com. After his third child arrived and having helped his wife open a city centre restaurant, the entrepreneur was drawn back into the technology arena and wanted to contribute to his local area. He went on to help transform Denver's tech startup scene by opening Galvanize, a creative brainstorming area and workspace for over 100 startup businesses. Not bad for a humble snowboarder.

7. Mark Cuban – Owner of Dallas Mavericks

When the Dallas Mavericks claimed their first Championship win in 2011, it would have been easy to mistake owner Mark Cuban for another crazed fan dancing in the stands. Not only is Cuban a successful business man and investor, but also a very down-to-earth guy and isn't afraid of publicity after making several cameo appearances on HBO's Entourage.

8. Nicola Cortese – CEO Southampton Football Club

When well-dressed and arrogant Swiss banker Nicola Cortese and his business partner Markus Liebherr purchased English Soccer team Southampton out of administration for $21 million in 2009, the club was languishing in the 3rd tier of English football and showing no signs of returning to the promised land of the multi-billion dollar industry that is the Premier League.  Cortese isn't afraid to upset the Soccer purists and takes an unusual approach when it comes to running a Soccer team. His unconventional methods have worked wonders though. Despite creating fan outrage by twice sacking successful managers, blacklisting club legends from the stadium for claiming free tickets and angering media by banning local newspaper coverage of the teams games, Cortese has propelled Southampton to 3rd position in the Premier League and the club is now worth more than $200 million.

9. Paul Durov – Vkontakte

Paul Durov, founder of Russia's answer to Facebook has a far-from-usual lifestyle. He never watches TV, never drinks alcohol, never eats meat and always insists people should spend less time on women and people who are “dumber” than themselves. He believes money is “overvalued, because producing things is more important than consuming things”. Durov surprised the world in August of this year after extending an invitation to the infamous NSA whistleblower Edward Snowdon to join his company based in St. Petersberg.

10. Marc Benioff – Salesforce.com

For someone in enterprise to give a keynote speech at CES, the biggest consumer gadget show in the world, would take some serious swagger and confidence. That's precisely what Marc Benioff, CEO of cloud computing company Salesforce, surprisingly did at the beginning of this year. But not only that, Benioff wants to lead a social revolution in the enterprise and sees his company as the potential driving force behind it. Benioff may be outspoken, but is clearly an ambitious man with a brave plan.

Author Bio 
This article is written by Ilan Nass from Fueled, an award winning mobile app design and development house based in New York and London.

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