Skateboarding and Entrepreneurship: Finding Passion in the Journey

Skateboarding Entrepreneurship

I remember first picking up a skateboard at age 12 after my first encounter with the X Games.  I was enjoying my summer vacation, flipping through the channels on TV when I came across the street skateboarding competition during X Games 8.  I couldn’t believe what I was seeing! I wanted to be just like those pros, doing flip tricks over gaps and grinding rails down sets of stairs. Who wouldn’t want to be like them? From that day on, there was one thing that I’ve consistently thought about every single day of my life, and that is skateboarding.


It wasn’t intentional. I didn’t have any sort of grand epiphany and say “I’m going to obsess over this forever”, it was a process. The process began at the beginning, one trick at a time.  Learning basic tricks wasn’t easy, but it was manageable. The real test came when I began my journey to learning the stepping stone to more complex tricks.  The kickflip looked simple enough but it took an insane amount of determination and persistence before accomplishing.  Even at that young age, I realized that my journey to the kickflip would be something that changed my mindset for years to come.


Every single night, I would visualize myself landing the kickflip, the trick that almost every other flip trick is built upon. I knew from the beginning that I would have to set a goal, including a timeline which became: By the end of the summer, I would be able to land kickflips consistently. The next day I got home from school, rushed outside, jumped on my board and to my not so pleasant surprise I HAD FORGOTTEN HOW TO OLLIE. But I didn’t simply give up and say “oh well”; I practiced all day for what seemed to be 5 or 6 hours until I laughed in the face of the Ollie. I started every day after this with 10 ollies, all of which were required (by me) to be perfect in order for me to begin to expand my trick knowledge. (I still warm up using this same method)  The next few months consisted of 3-5 hours daily of perfecting basic skateboard tricks including the Ollie, frontside 180, backside 180, shuv-it, half cab, and nollie.


By the time June rolled around, I had a pretty good bag of tricks under my belt but I knew I hadn’t reached my goal yet.  It was during those brutal, humid June days that I learned, and perfected the kickflip.  I got sun poisoning twice that summer from hours outside but despite my mother’s pleas, I didn’t stop.  The only thing that mattered was landing that kickflip, and I was going to do it or I was going to die trying.  I remember the day that it happened perfectly.  I had been skating all day and developing a method for landing the trick.  I would flip the board and concentrate landing with just my front foot 3 times in a row, and then 3 more times with just my back foot.  As the day was coming to an end, around 8 pm, it happened. I popped my board into the air and flicked my front foot off of the right side of the board. I jumped high, letting the board rotate in slow motion beneath my feet. Seeing the griptape come around and connect with my shoes was like watching a foreign film: It was beautiful, but I had no idea what was going on until I was back on the ground and riding away. I was in shock.  I turned around and looked back at the ground, then down at my board which I was standing on top of.  I tried again.  It didn’t happen. I tried 7 or 8 more times before landing the trick again.  It was getting dark but I could care less. I stayed outside that night until it was pitch black and I had landed 3 kickflips in a row: a requirement I set for myself before I would call it a day.


The rest of the summer saw similar days, this time learning more and more tricks until the kickflip became a trick I just used to warm up.  It was a stepping stone but I learned that even stepping stones have a big impact on the rest of the path.



Ten years later, I’ve found myself running my own business and going through the same mental trials that affected me as a child learning to skateboard. I study techniques, put them into practice, see no results, and get frustrated.  If Skateboarding has taught me anything, it’s that persistence pays off.  Nothing in life comes easily but with desire, persistence, and taking actions to make it happen, you can accomplish any goal you set for yourself.


Another big part of my skateboarding success, which I didn’t realize until years later, was visualization.  Every single night before going to bed, I would close my eyes and envision myself learning a certain trick.  I would see how the board flipped and turned, how I popped the tail, and how I caught the board when the trick had finished rotating.  By doing this every single night, it was easier for me to not get so frustrated when things didn’t go my way.  Don’t get me wrong I DID GET FRUSTRATED, some friends even knew me specifically for how I beat my board out of frustration :) But after I beat my skateboard to death, I didn’t give up.. I didn’t throw in the towel and say “screw it!” I took a breath.  I visualized the tricks in my head, and I tried again.


When you set a goal for yourself, and you do whatever it takes to accomplish it, you develop a love and a passion from that accomplishment.  Even more so, you develop a passion for the process and the journey that helped you reach that goal, in my case visualization and persistence.


I can see now that I use the same process when running my business.  Some of you know what I’m talking about, not everyone gets off on reading up on the latest SEO techniques but it PUMPS US UP! It makes us excited to learn something, anything that could possibly get us one step closer to our goal. When I read something that could help improve my website, I start visualizing, sometimes uncontrollably.  I see more people going to my site, I see more sales coming in, and I see more people who are getting value out of what I’m trying to do.  That’s what keeps me going.  It’s about meeting goals, connecting with more people, sharing more value, doing what we’ve been visualizing since day one.  And when you have so much passion for something, you inherently begin to love it, even the tedious stuff.  Posting 3 posts on facebook a day? I Love it.  Creating P&L Statements? I Love it.  Confirming shipment from UPS? I LOVE IT.  Every small task puts me closer to my goal just as every failed attempt put me one step closer to understanding and landing that kickflip.


Each of these stepping stones is essential to the overall path I’m walking down.  When you look at the big picture, you begin to appreciate the journey more than the end result.  The journey is passion.  The journey is why we do what we do.  The journey is entrepreneurship.

James Zeller
James Zeller


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