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5 seriously successful serial entrepreneurs

They have done it once, twice, or more: serial entrepreneurs don’t fear embarking on new business ventures over and over again – sometimes successfully, sometimes not so much. But always with the sheer determination to make a mark of their own in the business world.




There are entrepreneurs, and then there are serial entrepreneurs. Setting up one business is no piece of cake – it takes dedication, drive, the vision to deliver a strong value proposition, and the courage to fail. However, to work your way from one business to another,to invest time and energy into new ventures, and to become a serial entrepreneur who doesn’t fear failure and doesn’t sit back reaping the rewards of past successes, takes a very driven business person with certain traits. What many serial entrepreneurs have in common is an optimistic outlook, a willingness to take risks, an ability to deal with failure, a certain degree of restlessness, and – most importantly – a hunger for more success!

Here are some of the most interesting and successful top serial entrepreneurs in the world:

Niklas Zennström and Janus Friis, co-founders of KaZaA, Skype and Atomico Ventures

It all started in 2000, when the Scandinavian entrepreneurs created the peer-to-peer file-sharing application KaZaA. Three years later, they went on to develop Skype, a Voice over Internet Protocol (VoIP) service that fundamentally disrupted the telecommunications industry and the way we communicate in general. They sold Skype to eBay in 2005, but negotiated two years later to re-join Skype before selling to Microsoft in 2011 for USD 8.5 billion. Other businesses the two billionaires from Sweden and Denmark co-founded include Joost, Atomico Ventures and Rdio.

Despite their success as entrepreneurs and investors, the Scandinavian duo have a reputation for being quiet and understated, and they try to keep a low profile in public.

Jack Ma, the founder of Alibaba and other web-based businesses, one of China’s richest men

He has not always been successful. In his youth, Chinese-born Ma struggled to get into college and to find a job. What he never lacked though was determination. Determined to learn English at a young age, he biked110 kilometres  every day to meet tourists and practice his language skills. And the same happened when he first learned about the internet: driven by his observation that the world wide web was lacking information about China, he tookadvantage of the situation and co-founded China Pages with his wife, a company that created websites for Chinese businesses looking for customers abroad.

China Pages wasn’t overly successful. But four years later, Ma was determined to give it another go and founded his second internet company, Alibaba. The company has become the world’s largest online business-to-business trading platform for small businesses. In the following years, Ma set up other companies, such as Taobao Marketplace or Alipay, building a huge multinational conglomerate. 

Oprah Winfrey: the most powerful woman in the entertainment industry and Oscar nominee

Many people may know Oprah Winfrey as a TV talk show host, but she is actually one of the world’s most successful female serial entrepreneurs. Her business portfolio includes a television and film production company, magazine publishing, online media outlets and cable stations.

At the age of 19, she became the first African-American female news anchor  at WTVF-TV. Twelve years later, she started hosting The Oprah Winfrey Show. The show aired for 25 seasons and became the highest-rated talk show in TV history. During her time at the show, she founded her own production company, Harpo, followed by Oxygen Media, and different print and online publishing ventures. In addition to her successful businesses, Oprah is also an accomplished actress, having been nominated for an Oscar for her work in The Color Purple. Today, she may no longer be hosting her own TV show but she is still involved in her various business ventures, most notably as an executive producer and actress on various TV series and films aired on her OWN (Oprah Winfrey Network) channel..

Sir Richard Branson, founder of Virgin Group that includes 60 Virgin companies worldwide

Affected by a learning disorder, he dropped out of school when he was 16 years old. Fast forward 52 years to today and nobody would ever dare to ask Sir Richard Branson about his academic achievements, as he is now one of the most charismatic and successful entrepreneurs in the world. But how did he build his business empire?

After leaving school, he started a student-run magazine called Student, which was initially funded by advertising revenue generated by Branson. To help fund the magazine, he decided in 1969 to set up a mail-order record company called Virgin. This led to a record store on London’s Oxford Street and to a recording studio. In the 80s and 90s he ventured into the travel, broadcasting and beverage sectors. Today, the list of Richard Branson’s business ventures (and investments) seems endless and according to Virgin: “Richard has become the only person to build eight billion-dollar companies in eight different sectors.”

Wayne Huizenga: founder of three multi-billion-dollar companies in different industries

In 1962, Wayne Huizenga borrowed USD 5,000 from his father to buy a single garbage truck. Within 5 years, he had incorporated 100 other waste collection businesses into his company, Waste Management, Inc. and eventually it grew into one of the largest waste-disposal companies in the United States. In 1987 he repeated the success story in a different industry: he acquired a few video rental shops from Blockbuster, applied the same expansion techniques as his waste business, and soon he was opening a new shop somewhere across the US almost daily. He sold Blockbuster in 1994 as he wasn’t quite sure how to respond to the rise of technologies such as video on demand.

Later, he created AutoNation, an automotive dealership that became the largest in the US and purchased Swisher Hygiene. Huizenga’s love for sports saw him also creating, purchasing and owning several Florida-based sports teams. At the age of 80, Wayne Huizenga passed away, leaving a legacy of several Fortune 500 companies.

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