For Serial Entrepreneurs, Success is About Adaptability 

the key to repeated success is an openness to learn from mistakes  

July 19, 2018 | Denise Gifford

serial entrepreneurSerial entrepreneurs repeatedly begin new companies and are willing to take on the risk of new ventures. They are often thought of as successful, but just because they have a history of startups, does that really improve their chance of success the next time around? In some cases, serial entrepreneurs might more accurately be described as serial failures. An entrepreneur’s success often depends upon their attitude toward learning and their curiosity about their own business and the world in general. When entrepreneurs are able to learn from experience and leverage knowledge, they are more likely to achieve their goals time and again.

Serial entrepreneurs enjoy the challenge of starting a business. They may start a number of companies sequentially or simultaneously. They love the process of getting a company going, and may or may not stick around for the day-to-day operation over time. Elon Musk, Steve Jobs, Oprah Winfrey, Mark Cuban, and Richard Branson are examples of famous, and successful, serial entrepreneurs. Most billionaire entrepreneurs are, in fact, serial entrepreneurs.

But, of course, most serial entrepreneurs are not billionaires, and some don’t enjoy any real success at all. Starting many companies is not necessarily an indicator of success. It might instead be a worrisome sign of an entrepreneur who is particularly unable to learn. It could be that the entrepreneur enjoys the “hunt” and the adrenaline rush of the startup phase but lacks the ability to learn and the adaptability needed for the long run. These are skills that many serial entrepreneurs just don’t possess.

In fact, many serial entrepreneurs are overoptimistic even after failure, and are often uninterested in delving into why things went wrong. Research has shown that serial entrepreneurs in general seem to have an aversion to reflecting on failure and the lessons to be learned. It is part of the unique psychology of the serial entrepreneur to be overconfident. And even when they do take the time and effort to reflect on lessons learned, the impact of those lessons can be dampened by that supreme confidence.

But serial entrepreneurs who are high-performing and successful appear to know that optimism can only get them so far. Research shows that successful serial entrepreneurs demonstrate learning agility: knowing how to learn, applying what experience has taught them, and adapting that knowledge to new situations and circumstances. They are intellectually curious and can make connections from lessons they have learned over time. They are interested in and seek out opportunities to learn more. They value learning and know the importance of asking good questions. “A lot of times the question is harder than the answer. If you can properly phrase the question, then the answer is the easy part,” Elon Musk reportedly said in 2017.

Seeking knowledge also includes connecting with outsiders. Asking questions and learning from those outside the entrepreneur’s industry can bring fresh solutions to problems. Research has found that seeking answers from analogous fields can be a source of innovation: three eminent research economists wrote in the Harvard Business Review, “there’s great power in bringing together people who work in fields that are different from one another yet that are analogous on a deep structural level. Such as makeup and surgical infections, surprisingly. Or inventory management and robot games. Or malls and mines.” Learning from other fields is beneficial because the entrepreneur can draw on different pools of knowledge, and asking others outside their industry for ideas can provide new insights, unconstrained by “known” solutions in a given field.

Successful serial entrepreneurs also appear to have a curiosity that extends beyond business.  “Having an insatiable curiosity for the world around you is an essential skill as an entrepreneur,” Richard Branson wrote at And successful entrepreneurs know that learning outside of business is critical, especially in the future of work. “I personally think there’s going to be a greater demand in 10 years for liberal arts majors than there were for programming majors and maybe even engineering,” Mark Cuban said in 2017. “When the data is all being spit out for you, options are being spit out for you, you need a different perspective in order to have a different view of the data.”

Successful serial entrepreneurs have a respect for the power of learning and they consistently seek out knowledge from many – and sometimes unconventional – sources. They don’t just make starting businesses a habit. They make learning a habit, and this is an important contributor to their success.

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  • About The Author
  • Denise Gifford is co-founder of InfoWorks® International, which has provided consulting and training to companies worldwide in project management and related skills. Prior to leading InfoWorks, Denise worked in sales and marketing management, and as a consultant to the financial services industry. She holds her MBA from Northwestern University’s Kellogg School of Management.