The Truth About Serial Entrepreneurship (And 4 Famous Serial Entrepreneurs)

What is a serial entrepreneur? We've heard the phrase before, but what does it mean? Can anyone who has started and runs a successful business eventually be defined as a serial entrepreneur?

The answer to that last question is, no.

Entrepreneurs are a unique kind of group, with traits and habits that can't be possessed by everyone. But serial entrepreneurs take what entrepreneurs do (starting and operating a business) and do it again, and again, and again.

According to, a serial entrepreneur is constantly coming up with new ideas and ways to start new businesses:

"As opposed to a typical entrepreneur, who will often come up with an idea, start the company, and then see it through and play an important role in the day to day functioning of the new company, a serial entrepreneur will often come up with the idea and get things started, but then give responsibility to someone else and move on to a new idea and a new venture."

If starting your own business seems like a tough feat, imagine taking on this challenge multiple times in a row. Here are four entrepreneurs who did just that and succeeded.

Elon Musk

"Failure is an option here. If things are not failing, you are not innovating enough.” - Elon Musk

Elon Musk comes from an educational background, earning degrees in economics and physics at the University of Pennsylvania and moving on to a graduate program in applied physics and materials science at Stanford. However, Musk only stayed at Stanford for two days before dropping out and founding Zip2. Zip2 helped newspapers develop city directory websites before being bought by Compaq.

Musk went on to found, SpaceX, and eventually Tesla.

Jack Dorsey

"You can worry about the competition...or you can focus on what's ahead of you and drive fast." - Jack Dorsey

Jack Dorsey is best known for founding Twitter in 2006, one of the most popular social networking sites today. Despite Twitter's success to this day, he also went on to found Square, Inc. in 2010. He continues to be the CEO of both companies and has received multiple awards for his innovation.

Oprah Winfrey

The biggest adventure you can take is to live the life of your dreams. - Oprah Winfrey

Oprah Winfrey has had her share of failure, but  she eventually turned her misfortune into success. 'Serial entrepreneur' is just one of her many titles.

She founded Harpo Productions in 1986, Oxygen in 1998, and the Oprah Winfrey Network (OWN) in 2011. Her 25+ years of entrepreneurship prove that it's never too late to start a new project or chase a new dream.

Mark Cuban

"Work like there is someone working 24 hours a day to take it all away from you." - Mark Cuban

Mark Cuban is famous as the owner of the Dallas Mavericks and one of the sharks of Shark Tank. His fame came as a result of hard work and building multiple successful endeavors.

He first founded MicroSolutions in 1983 and sold it seven years later. Later in 2001, he founded HDNet. He has also financially supported several other endeavors, such as, 2929 Entertainment, and Synergy Sports Technology.

Although Cuban created quite the empire today, his first ever job was working as a bartender. This goes to show success can come from those who have a vision and work very hard.