What Really Drives Serial Entrepreneurs?

Being a serial entrepreneur requires taking great risks without any promise of reward, flourishing in the face of repeated stress and uncertainty and, often, dealing with unfamiliar tasks and industries. Though making a career based on constant change can keep a business owner from getting bored with routine, it’s not a path for the faint of heart, and begs the question of what makes a serial entrepreneur drawn to a world of professional uncertainty. Do serial entrepreneurs possess great instincts — or are they simply afraid of commitment? Here’s a look at what really drives serial entrepreneurs.

They value challenge over security. Entrepreneurs may start a business in hopes of that one successful venture that leads to a big payday, and for them, attaining such financial security on their own terms is fulfilling. For serial entrepreneurs, there is no “end game”; the payoff isn’t the finish, but the process that involves innovation, creation and problem solving. Serial entrepreneurs are ultimately driven by a need to explore how something can be changed or done differently — regardless of the industry. As Dan Steppe, former director of the Wolff Center for Entrepreneurship at the University of Houston's business college recently told Entrepreneur magazine, the entrepreneurs he encounters have a common thread: They are motivated by curiosity and the challenges that pose a question. Serial entrepreneurs never cease to ask “why” or “why not?”

They fear not trying more than failing. Serial entrepreneurs are more afraid of not trying than failing. Case in point? Conferences like FailCon, that were originally founded as a venue for owners of failed startups to commiserate, have gone global, having morphed into strategic gatherings that empower serial entrepreneurs to network, share stories of success and failure, and most importantly, learn from like-minded peers and mentors, so they can continue their entrepreneurial pursuits — regardless of the outcome.

They bring a balance of logic and emotion to their work. Serial entrepreneurs tend to be gifted at seeing the “big picture,” logical enough to know where they are most valuable in a venture, and humble enough to recognize how and when to outsource the tasks that they aren’t skilled at. But, that doesn’t mean serial entrepreneurs don’t have feelings for their businesses, or fail to recognize the impact that their entrepreneurial endeavors make on the world. As Dallas Mavericks owner Mark Cuban explained in a video interview to Inc. magazine, the emotional component for serial entrepreneurs fuels the purpose in a way that is far more motivating than money and recognition. Though he admits one of his top priorities is to build the Mavericks franchise to be “ungodly profitable,” he recognizes that his business has the power to emotionally impact the lives of others, including his employees, his team and the fans. Ultimately, he says that’s what drives him to make the Mavericks successful.

They use the past to make a better future. Starting a business for the first time is often a test-and-learn experience that requires working with few resources, little capital and long hours. Though there are no guarantees that a new business will succeed, serial entrepreneurs use the lessons of the past to manage future risks more appropriately — particularly when there is more capital available. As a result, they can spot their past decisions that may have hindered growth, or that were more costly than necessary. Though experience doesn’t guarantee a successful outcome, serial entrepreneurs are able to fine-tune the strategies they bring to each new venture, to optimize their startup approach to be a bit better than the venture before.

Business owners who find themselves bored within a few years of starting a successful venture, are more fueled by the excitement of starting than finishing and who are constantly searching for new ways to solve problems may very well be serial entrepreneurs. For this special breed of business owners, the thrill of starting a business is more about the journey than the destination.