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The 5 Characteristics of a Serial Entrepreneur
What is a serial entrepreneur?

Oftentimes, should-be entrepreneurs find themselves dissatisfied in life when they are in an ‘employee role’. Their career dissatisfaction slowly but surely creeps into their personal life too. Feeling lost and unmotivated in that role they begin to self-doubt. I know this because I’ve been in that position…

Fresh out of college I went to work for a big bank thinking it would give me the challenge and experience I needed. However, after a few months of dealing with office politics and the gigantic bureaucracy, I was bored out of my mind and frustrated. I found myself falling into the 9 to 5 trap too. You know what I’m talking about… when you look forward to weekend drinks, poker night and other rather irrelevant activities. Long story short, I wasn’t thriving in the employee role.

At the time, I wasn’t sure why I felt like something was missing in my life, but now I get it. I was made to be an entrepreneur. My personality is conducive to getting out in the world and hunting my own meat… if I’m not putting it all on the line for a new venture, I just don’t feel fully alive.

Over the years I’ve been lucky enough to deal with dozens of highly successful serial entrepreneurs, and noticed that we all share 5 characteristics.

So for those of you in that employee role who feel like something isn’t quite right in your career, this article is for you. Your dissatisfaction may rest in the fact that you were meant to be your own boss. You may have the DNA of a serial entrepreneur. If that is the case then the only way to truly feel happy is to become your own boss and get out on the front line, where risk versus reward dictate your daily decisions.


5 Common Characteristics of Serial Entrepreneurs

Love to compete: It’s no coincidence that many of the world’s greatest athletes end up becoming entrepreneurs after retiring from sport. They’re obsessed with competing, and there’s no better way to test your mental mettle than by starting your own business.

Since I can remember, I’ve been what some may call ultra-competitive… for example, I have a mental record of who is up in golf rounds between me and my dad, over the course of my life. 13-9 for those who are curious… not saying for who though.

Some people may get offended by how competitive you are. It may even embarrass your spouse (my wife included). Those of you hyper-competitive people know exactly what I’m talking about. To some, competition is scary. To people like us, it’s fun.


Have trouble dealing with authority: Almost all serial entrepreneurs I know have a Libertarian side to them. That’s because they don’t believe in big government. They hate the idea of a watchful government monitoring their every move and strongly believe in personal choice, private property laws and economic freedom. They’re strong and independent thinkers, and that’s why entrepreneurship is such a good fit.

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Obsessed with building and growing: Are you the type of person that is always working on a project around the house? Whether it’s planting trees, building a new deck, or restoring a vintage car, you’re regularly looking to create and improve things. If so, the world of entrepreneurship is probably where you belong.


Can’t sit still:  People may say you have ADD, I call it being a winner and constantly seeking a challenge or improvement. Even on vacation I have a hard time sitting still for a significant length of time. Rather than lying on a beach all day, I want to learn to surf, windsail or get a volleyball game going.


Love to research: Do you read a lot of non-fiction? Watch alternative news sources, not the mainstream media, to get caught up in world events? Do you find yourself regularly thinking about how to improve things in everyday life? These are all signs that you have a very inquisitive mind, which is common among serial entrepreneurs.


What we do for a career has a direct impact on our personal happiness. If you don’t enjoy your work, you’ll probably carry that dissatisfaction home. In light of that, if at least four of the five characteristics above line up with who you are, then maybe it’s time you thought about joining the entrepreneurial ranks.

Stay hungry,
Aaron Hoddinott signature