Is Serial Entrepreneurship For You?

Serial entrepreneurship is a calling. In fact, not many people actually know they’re a serial entrepreneur until they have already become one. You may already have your hand in a few cookie jars before you realize you are of the serial variety.

I have always been searching for new ideas, various projects and things to learn. I never wanted to stick to just one career path, so serial entrepreneurship was a natural fit.

Is serial entrepreneurship your calling? Here are six serial entrepreneur behaviors to help you heed the call.

You Don't Believe Curiosity Killed The Cat

Curiosity is a big aspect of being a serial entrepreneur. We are hardwired to seek out new information and ask questions. Curiosity drives entrepreneurs to find answers and solutions many people face or fill a void in people’s lives.


Walt Disney once said, “We keep moving forward, opening new doors, and doing new things, because we're curious and curiosity keeps leading us down new paths.”

The curiosity never ceases, not even when we sleep. If curiosity to learn more is part of your personality, you very well could be a serial entrepreneur. More so if you are ready to take action based on the knowledge you’ve compiled and share it with the world in an innovative way.

Failure Is An Option, But You Can’t Live With Regret 

Regret is one of the most frightening feelings for serial entrepreneurs. This makes us unique. Most people fear failure. But the prospect of not taking action on a potential business idea keeps entrepreneurs up at night.

Serial entrepreneurs live for the thrill of success, to make something from nothing and to overcome challenges along the way. We generally live life to the fullest. Professionally we take risks on businesses or investments that are indeed challenging but fuel that thrill.

I always want to learn more and expand my industry knowledge. If failure is an afterthought, you are heeding the call of entrepreneurship.

You Had A Lemonade Stand

The journey toward serial entrepreneurship often begins before you are even old enough to drive. It may have been a lemonade stand or a grass cutting and snow shoveling side hustle, depending on the weather.

The main point is that you acted on your entrepreneur potential early on, whether you realized it yet or not. Sadly, many people see entrepreneurs as money hungry business builders who are not emotionally invested in their investments. But if you give a serial entrepreneur $100 million, he or she will likely invest most of it in new ideas, startups, businesses, products and more. Serial entrepreneurship is not simply a job. It's a way of life.

You Network Like A Boss

Look at your contacts and LinkedIn connections. If you have a robust list of connections that could be nurtured into strategic relationships, you are definitely primed for serial entrepreneurship. Strategic relationships are extraordinarily important to entrepreneurs. You should have a mentor, partners and a variety of talented people at your fingertips.

Networking helps entrepreneurs grow and be successful. It allows you to make others successful as well. Building these strategic relationships means being involved in various business opportunities at once.

You may be consulting for free, but you are involved. If your LinkedIn profile lists two, three or more positions you presently hold, guess what? You are definitely a serial entrepreneur.

You Often Feel Restless Professionally

The professional freedom and variety that comes from entrepreneurship are indeed enticing. This is especially true for those working in the realm of the 9-to-5 cubicle company who have a restless urge building up daily.

Entrepreneurs are perpetually taking on, or investing in, innovative and unique ideas. If your professional mindset needs constant change or if you find yourself moving from one job or career every few years, serial entrepreneurship is your calling.

Listening to that restless business spirit inside you can certainly be rewarding. However, entrepreneurship is no easy road and we are no stranger to working long hours or weekends.

Your Time Management Skills Are On Point

Serial entrepreneurs are juggling multiple businesses, projects and tasks. This makes time management a valuable asset. Entrepreneurs should be highly organized and aggressive when it comes to time management.

Powerful time-management skills increase your opportunity for success. The more methodical we are as entrepreneurs, the faster we can advance an idea from startup to global brand. This allows you to take on more and move quickly to your next investment.

Serial entrepreneurship is all about scaling fast with sustainable growth trajectory at the heart of every decision. This key element separates us from the one-time business owners.

If you can relate to any or all of the above you are most likely a serial entrepreneur. Congratulations and welcome to a rewarding professional path that will feed your passion for developing new innovative ideas. Our road is one less traveled and often filled with ups and downs. But that’s what makes every second thrilling and downright addictive.

Kumar Arora is a serial entrepreneur turned investor, one of the sharks on CNBC’s “Cleveland Hustles,” produced by Lebron James, as well as an advisor to 1M1B Foundation & United Nations.