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The Inherent Rebellion of Entrepreneurship

This story appears in the October 2015 issue of Entrepreneur. Subscribe »

My first act of rebellion came in the fifth grade. OK, maybe it wasn't pure rebellion, but it was the first time I did something that was against the rules.


It was Mr. Saviano's history class. We were studying the and its impact on families. Our assignment for the evening was to capture our 's history by drawing a picture of what our grandfathers had done for a living.

This is great, I thought. I loved history. I loved drawing. And oh, how I loved the waxy smell of crayons. I jumped on my bicycle, pedaled my way home from school and interrogated my mom on the topic of my grandfather. This story needed a permanent place in the notebook of my childhood. It was clearly something that had to be told, and I was the one to do it.

"Your grandfather was an entrepreneur, honey. He rented boats and owned a lumberyard. He did lots of things," my mother explained in her deep, lilted Southern accent.

An entrepreneur? Huh? It was at this point that my inner rebel took over. What's an entrepreneur, and how in the world do you draw one? There were crickets in my brain. So I shrugged off my mother's words and did what any good Texan would do: I told a tall tale. I drew a cowboy on a horse and the next day told the entire class that it was my grandfather. And there it was. I officially entered my journey as a storyteller, and as a rebel.

Maybe it wasn't revolutionary. But still, I broke the rules. I thought outside the norm. I was guided by my own (perhaps misguided) creativity—and I liked it.

Nothing captures my imagination as much as those who disobey, experiment, defy traditional thinking and break the rules. Einstein. Van Gogh. Dante. The list goes on and on.

Rebel. I love the word. It's both a noun and a verb. You can rebel and you can be a rebel. When one hears it, a certain picture comes to mind. (There's one for this country; different caricatures exist elsewhere.) But you don't have to ride a motorcycle to be a rebel. You don't have to be James Dean. I've met plenty of suit-wearing, Lexus-driving rebels in my day. It's not about being naughty. Pushing boundaries and making people uncomfortable—that's rebelling. Standing out from the crowd. Challenging convention. Creating something new. This is true in art, in government and in business.

If you are reading this, you have a little bit of rebel in you. Entrepreneurs are rule-breakers by nature. They disrupt, innovate and feel damn good about it.

This issue is dedicated to that spirit—to rebels and to rebellious thought. Take a look at this month's Innovators feature: HR is a pain we all must endure, but is changing the way entrepreneurs approach this thorny topic, and pissing off traditional providers along the way. Our examines why rule-breakers make great entrepreneurs. Elsewhere, you'll learn if you are your own elk or part of the herd (it'll make sense when you see it), and you'll see stories about people taking risks, trying new options, failing, succeeding and doing it all over again.

So I drew a cowboy when I wasn't supposed to. I thumbed my nose at convention. But it's funny: What I realize now is that my grandfather, who started businesses out of thin air, was quite a rebel himself.

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