When I was 16 years old, my idol was a guy by the name of Scott Olson.

He wasn't a rockstar, nor was he a professional athlete. He was an entrepreneur. More specifically, he was the founder/inventor of a product that became a global phenomenon--Rollerblade.

Growing up in Minnesota, where Rollerblade started, made Scott even more of a hero to me. Not just because he understood the pain of Minnesota winters, but because I actually had a shot at spending time with him.

The day I got my drivers license, I drove down to a small skate shop near Minneapolis, that was owned and managed by Scott's wife, and convinced her to give me a job.

Every spare minute I had, I worked at that store. I took every shift that nobody wanted, sometimes both opening the doors in the morning and closing the shop at night.

I loved that job. Not because of the work, but because it got me closer to my idol.

I wanted to learn everything I could from this guy, which meant that I was willing to do anything to spend more time around him.

So, in Miyagi-esk style, Scott would invite me out to his house on the weekends to help with parties they were hosting. Sometimes I would be a valet, other times I would help clean up. It didn't really matter to me, as long as I was there, in his presence.

In the end, it wasn't really lessons he taught me, it was more behaviors. Things I learned by observation.

Scott was a simple man that happened to make the right product at the right time. He was very casual and not at all what you imagine a successful, multi-millionaire entrepreneur to be.

From my observations of Scott and my many years of observing and working alongside other entrepreneurs in life, I've been able to come up with what I believe are the two greatest characteristics among successful entrepreneurs.

The first is conviction.

In a recent interview, Tony Hawk was asked what it takes to be a great skateboarder. He said that the only difference between being good and great was the skateboarders belief that they were going to be. They're the ones that keep getting back on their board after they fall.

Successful entrepreneurs are the same. Failure never stops them.
They believe with every ounce of their being that it's not a matter of if, it's a matter of when. There is no doubt in their mind that they're going to succeed.

Some people mistake this for delusion. Entrepreneurs call it conviction.

The second characteristic is curiosity.

When someone asks me for advice, the first (and sometimes only) thing I tell them is to "Always Stay Curious" (ASC). Curiosity breeds knowledge and knowledge breeds wisdom.
Successful entrepreneurs are constantly asking questions and learning from others.

They're never satisfied with what they know, and believe that knowledge is power.

They know when it's time to listen and they do it with purpose.

Curiosity is what allows them to take risks and try new things.

Interestingly, the combination of these two characteristics enables entrepreneurs to make decisions fearlessly.

Scott Olson has both of these characteristics and I thank him for showing them to me. While he ultimately lost his ownership in Rollerblade in devastating fashion, he continues to swing the bat and inspire me to this day.

Published on: Apr 30, 2015
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