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5th Time’s a Charm: The Life of a Serial Entrepreneur

If entrepreneurs are rare, serial entrepreneurs are even rarer. But what drives the serial entrepreneur?
Andrew Deen has been a consultant for startups in almost every industry from retail to medical devices and everything in between. He implements lean methodology and currently writing a book about scaling up business. Twitter @AndrewDeen14
Andrew Deen has been a consultant for startups in almost every industry from retail to medical devices and everything in between. He implements lean methodology and currently writing a book about scaling up business. Twitter @AndrewDeen14

When it comes to success, people have different definitions. Some believe it’s making enough money so you can spend your days sipping drinks in the Caribbean. Others believe that making a difference in the world constitutes true success. Asking a serial entrepreneur how they define success may yield a variety of answers, but the fact is, these are the people who find fulfillment in starting and building new companies.

A serial entrepreneur is someone who has started or bought multiple companies, often in succession, but occasionally simultaneously, with the goal of increasing their value. Though the most successful serial entrepreneurs might not have the same name recognition as the Gates, Jobs, and Zuckerbergs of the world, many serial entrepreneurs have been quietly successful, starting and selling off new companies throughout their lives. If entrepreneurs are rare (only about 1 in 10 American adults dip their toes into entrepreneurship), serial entrepreneurs are even rarer. But what drives the serial entrepreneur? And what sets them apart from other visionaries who just build one company and stick with it for as long as possible?

What Drives the Serial Entrepreneur?

For many entrepreneurs, their concept starts with a passion, a vision. For the serial entrepreneur, concepts usually start with an opportunity. A gap in the market. A brilliant, cutting-edge product consumers will love. The next big technological advancement. A great investment opportunity. Opportunities, plus the lure of building and growing businesses and bringing in revenue, are what drives the serial entrepreneur. Some criticize these individuals as being cynical or only after a profit, but the truth is that we need serial entrepreneurs—they’ve created so many businesses that have greatly benefitted society.

The Qualities & Skills of a Serial Entrepreneur

Entrepreneurs require certain qualities that are sometimes difficult to cultivate, and extremely rare naturally. Serial entrepreneurs must have all of these skills—and the willingness to do it all over again, over and over. Here are just some of the skills that have helped make some entrepreneurs successful at building new ventures time and time again:

  • Persistence
  • Listening skills & empathy
  • Emotional intelligence
  • Communication
  • Business knowledge
  • Delegation
  • Objectivity and logic
  • Charisma
  • Leadership
  • Time management
  • Scaling
  • Innovation
  • Curiosity
  • Networking
  • Good instincts

In addition to these traits and skills, serial entrepreneurs need to be tough, risk averse, and willing to make tough decisions. It’s not easy to cut ties with a project and move on, or know when to sell, but these are decisions all serial entrepreneurs must make, project after project.

The Relative Obscurity of Successful Serial Entrepreneurs

Aside from serial entrepreneurs who started several lackluster companies before hitting on a really great concept, most successful serial entrepreneurs are fairly unknown to the general public. This may be because these people tend not to be as tightly tied to their brands as the founders of the most prominent companies in the world. Since they shift from concept to concept, people have trouble forming an opinion of them. However, that doesn’t mean these serial entrepreneurs haven’t created empires—far from it. Wayne Huizenga, at one time an owner of the Miami Dolphins, built 3 multibillion-dollar companies: Waste Management, Blockbuster, and AutoNation. Though he’s made more money than most of us could ever dream of having, that doesn’t mean he stands still—a few years ago he was still exploring new projects. That’s a common thread among serial entrepreneurs—there’s rarely a moment when enough is enough.

An Uncommon Calling

The life of a serial entrepreneur, just like that of an entrepreneur firmly entrenched in one business, isn’t for everyone. It takes a very unusual personality and set of skills to succeed as a serial entrepreneur, and not many can pull it off. When it works, however, big things can happen, and empires can be built.

If you don't feel that U.S. culture (and much of the world in different ways) is in turmoil, you are not paying attention.
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