Steven Spielberg: Dreamworks

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Spielberg got his start charging admission to his homemade movies as a child.  His first war movie Escape to Nowhere was award winning at age 12.   After doing Jaws, ET, and Jurrasic Park, Spielberg co-founded Dreamworks which went on to do 10 movies over $100 million at the box offices.  Forbes puts Spielberg’s net worth at over $3.1 billion.

Hugh Heffner: Playboy

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The playboy himself, Hugh Heffner was born to conservative Nebraskan farmers.   After moving to New York he found the need for a gentleman’s magazine.  Starting with only $8,000 raised from investors Heff sold 50,000 copies of his first magazine featuring Marilyn Monroe.  Originally named “Stag Party” Hugh changed the name to Playboy.  His fame has taken him from magazine and mansion to pay-per-view and mainstream television.

Sean Combs: Sean John Clothing & Bad Boy Entertainment

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Diddy, Puffy, call him what you like but the man who discovered Notorious B.I.G is one of the best self promoters of all time.  His Sean John clothing line does over $400 million in sales and is now developing his Ciroc brand of Vodka.  Diddy is more than just an entrepreneur however, running the NYC Marathon and performing in A Raisin in the Sun on Broadway.

Tyra Banks: Bankable Enterprises

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As a model Tyra became the first black cover girl for Victoria’s Secret, Sports Illustrated Swimsuit and GQ.   Her fame has since then moved to television hosting America’s Next Top Model and The Tyra Banks Show.  Tyra’s empire includes jewelry, shoes, and perfume and is widely known for her positive influence on women 18-34.

Magic Johnson: Magic Johnson Enterprises

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As the best point guard of all time, Magic’s career came to a startling halt after being diagnosed with HIV.  Recommitting his life to business and philanthropy Magic has been valued at almost a billion dollars.  Targeting inner city areas with Lowes Theaters, Starbucks, and TGI Friday’s Johnson looks for opportunities where others are fearful.  Magic’s larger than life personality is still seen all over TNT, ESPN and CBS with their coverage of both the NBA and NCAA basketball.

Kathy Ireland:  Kathy Ireland Co.

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Fashion model Kathy Ireland told Newsweek “I’ve never felt comfortable earning a paycheck off of how someone perceived how I looked,” and has never looked back since.  Her mission became “finding solutions for families, especially busy moms.”  Ireland sells anything from exercise videos to rugs to home theater setups.

Bill Gates: Micrsoft

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Although Gates fortune has fallen recently due to the loss of market share to another man on this list, Gates is still responsible for revolutionizing the personal computer.  Gates now serves on the board of Warren Buffet’s Berkshire Hathaway and more importantly spends his time on charitable donations through the Bill and Melinda Gates Foundation supporting Global Health and Development.

Richard Branson: Virgin

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This UK entrepreneur started off founding a magazine called Student and expanded quickly into the music industry with Virgin Records.  The self proclaimed “Rebel Billionaire” has over 300 companies belonging to the Virgin brand.  For fun Branson hangs out on his private island, or tries to break world records like crossing the English Channel in an amphibious vehicle or trying to circumnavigate the world in a hot air balloon.

Steve Jobs: Apple

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As an adolescent Jobs spent his time tinkering with computers at Hewlett Packard in his hometown of Mountain View, California.  As the most famous Silicon Valley entrepreneur of all time, Steve Jobs left his mark on computers, digital music and now cellular devices.  A perfect case study on the trials and tribulations of and entrepreneur, Jobs has survived in both business and life after his recent liver transplant.

Oprah Winfrey: Harpo Inc.

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Born in a poor Missisippi town and sexually abused as a child, Winfrey excelled in local media outlets and worked her way up the ranks into television.  With ownership in the Oprah Winfrey Show, Harpo Studios (Oprah spelled backwards), the Oxygen Network and Oprah Magazine her net worth is set somewhere over $2 billion according for Forbes.  Oprah is best known for her philanthropic efforts to get people to “live your best life”.