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3 Inspiring Serial Entrepreneurs

If you think about it, serial entrepreneurs are perhaps some of the bravest people in the world, as they often give up normal salaries, work schedules and family lives to pursue their ideas. At first, it seems that successful businesspeople must possess some sort of special trait or knowledge that the rest of us lack, but this isn’t the case. Here, we’ve explored the lives and successes of three serial entrepreneurs, all of whom came from different backgrounds and still managed to build incredible empires.

Paris Hilton

paris-hilton” (CC BY-SA 2.0) by  Chesi – Fotos CC

Paris Hilton made her first successful business decision at the tender age of 15 when she agreed to join Donald Trump’s modelling agency, a choice that would lead to her releasing her first fragrance at just 16 years old. After a few years in the spotlight, Hilton was approached by Fox producers to star in her own reality TV show entitled The Simple Life, where many of us were first introduced to the young socialite.

As Hilton’s fame grew, she launched companies, created fashion lines and opened numerous stores around the world, and it soon became clear that the real Paris Hilton was far more business savvy than anyone had realised. “My grandfather and great-grandfather created such a huge empire,” Hilton told Forbes in a 2014 interview. “As a little girl I really looked up to them and wanted to do something of my own.”

Paris Hilton now owns 50 stores in over 40 countries, her fragrance line has become a $1.5 billion industry and she even plans to launch her own luxury hotel chain with buildings in Dubai, New York and Las Vegas. The Las Vegas plot is a particularly exciting endeavour as Hilton has always managed to have a good time between making industry decisions and promoting her brand. Indeed, she is currently an ambassador alongside Verne Troyer at, one of the UK’s fastest growing online casinos which is often awarded for their innovative ‘Hollywood’ marketing strategies and impressive gaming catalogue. Hilton also spends a lot of her time travelling the world as a successful DJ, often visiting Ibiza in the summer months to play at popular clubs.

Overall, Paris Hilton is an incredibly successful serial entrepreneur, but what is most impressive is her ability to enjoy her life and have fun between the business deals.

Sir Richard Branson

Richard Branson” (CC BY 2.0) by  D@LY3D

Richard Branson was born in England in 1950 to barrister Edward Branson and Eve Branson, a flight attendant. As Branson began school, it became clear that he struggled with dyslexia and at 16 he dropped out of Stowe School to launch a free youth culture magazine entitled Student. In its first edition alone, the magazine made $8,000 worth of advertising and 50,000 copies were printed.

By 1969, Branson had moved to London and was very much part of the music scene. It was this environment which inspired him to create a mail-order record company named Virgin, which he hoped would fund his magazine. Virgin’s success was modest, but encouraged Branson to open a record shop on Oxford Street and later to build a recording studio in Oxfordshire.

After the launch of the Virgin Records label, Branson signed Mike Oldfield in 1973 and created the single “Tubular Bells” which was an instant hit that remained in the UK charts for 247 weeks. Branson went on the sign the Sex Pistols, Culture Club, the Rolling Stones, Genesis and numerous other groups that would propel Virgin Music to one of the top six record companies in the world.

Following the success of Virgin, Branson went on to create the travel company Voyager Group, Virgin Atlantic airlines and Virgin Megastores before he eventually had to sell his company in 1992 for $1 billion due to financial issues. This didn’t stop Branson though, and within a year he founded Virgin Radio and eventually launched a second record company in 1996. Entitled V2, the record company signed some very popular artists including Powderfinger and Tom Jones.

Branson continued to be a serial entrepreneur and his Virgin Group now owns more than 200 companies around the world, including a train company, a game reserve, a mobile phone provider, the space tourism brand Virgin Galactic as well as online casinos Virgin Games and Virgin Casino, which are often nominated alongside Hilton’s bgo for awards.

Needless to say, Branson’s resilience and drive are both inspiring and legendary.

Oprah Winfrey

President Barack Obama with Oprah Winfre” (CC BY-ND 2.0) by  U.S. Embassy Jakarta, Indonesia

Of all of our successful serial entrepreneurs, none have come as far as Oprah Gail Winfrey. Born in Mississippi in 1954, Winfrey was faced with multiple hardships and abuse in her small farming community. Fortunately, she later moved to Nashville to live with her father and attended Tennessee State University in 1971 to study radio and television broadcasting.

After university, Winfrey moved to Baltimore to host a TV chat show called People Are Talking where she remained for eight years before being recruited by a Chicago TV station. Winfrey received her very own morning show called A.M. Chicago and soon gained over 100,000 viewers more than her closest competitor Phil Donahue. Winfrey became a US celebrity in no time and even starred in Steven Spielberg’s 1985 hit The Color Purple.

It was in 1986 that Winfrey finally launched the Oprah Winfrey Show, which aired on 120 channels, had an audience of 10 million people and grossed $125 million in its first year. Winfrey swiftly created Harpo, a production company, and took ownership of the show from ABC. As Winfrey became more famous, she was able to pursue issues close to her heart and in 1994, President Clinton signed a children’s rights bill proposed by Winfrey.

To this day, Oprah Winfrey continues to inspire people as she changed from a scared little girl on a Mississippi farm to a media giant and powerful activist. Like Oprah, Paris Hilton and Richard Branson have both defied expectations and become successful serial entrepreneurs, an endeavour it seems anyone can achieve if they are determined enough.

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