How I Learned Skateboarding

It was the summer of 1997, I had never been more bruised in my life. The left-overs of my school vacation were scabs on my elbows, bruises on my shins, and tired legs. While other kids were at the beach, building sandcastles and throwing frisbees, I was in my driveway where I was practicing for my dream of learning how to skateboard.

There was one problem. My friends were better at skating than me. I desperately wanted to keep up enough to skate with them. I was so embarrassed I avoided the skate park. I feared getting laughed at. I had a feeling something separated the park skaters from me. I didn’t feel like I could do anything right on the board. I would fall on turns, ollies, and any attempt of going down a ramp.

My dream to skateboard led to endlessly searching the internet for tips. I ended up buying two skateboarding trick tip videos, a local video and a video from Thrasher Magazine. I was so excited to finally get the secrets to skateboarding! I was so motivated that I watched the videos every for over 30 days!
Immediately after watching, I would go outside and practice. I tried everything they said word-for-word. After over a month of trying everyday for hours, I became frustrated with the lack of progress.

On my ollies (a trick you lift all four wheels with), I could hardly lift the back to wheels off the ground. My style was sloppy, and I still wasn’t ready for the park.

Points to Remember

  • Anyone can learn skateboarding.

  • There is no age, weight, or height which is optimal.

  • Falling is a part of everyone’s learning process.

One day in the sixth grade, I saw three kids skateboarding fast, grinding curbs, and doing kickflips (full flip of the board in the air) in front of the school.  They were very good.  I asked my friend Alex, “These kids are amazing!  They are grinding, and get so much air on their ollies.  Who are they?”

“They’re sponsored,”  Alex replied.

“Sponsored?  You mean like paid to skateboard by companies.”

“Yeah, they ride for a local skateboard shop called, Wheels and Waves.   They do competitions and demos all over the state.  They’re good man.”

“Wow.  I’ve got to be good like that someday.” I said.

“You want me to go introduce you?”

I agreed and we walked over.  Next thing I know, I was witnessing, 11 inch high heelflips and fakie kickflips right next to me.   Wow!  Dan, Josh, and Matt were sponsored and told me they skated everyday at the skate park.  (The place I had desperately tried to avoid.)  They invited me to come and see their sponsored demonstration at the park that weekend.   There was going to be free products giveaways, pros, and lots of sponsored skateboarders to watch.

The Guy Who Taught Me Everything

Astonished by their moves, I agreed and went to the demonstration that weekend.  At the demo and over the next couple weeks, Matt and I grew close and he asked me to go skating with him.  I told Matt, “You know I’m not very good.  I skate a lot, but I’ve never actually skated the park.”

“That’s okay. My favorite terrain is flat ground.  I have a flat driveway which is smooth and has a small jump ramp and rail.  My Mom won’t be home and there will be no cars around.  It’s the perfect place to learn!  Do you want to go skate it tomorrow?

Knowing this was at his house, I felt a bit more comfortable.  “Sure!  That would be great!”

The next day after school, we skated over his house.  I got on my board and showed him what I could do.  The first trick up was the ollie.  I bent my knees into my chest, held my arms out and popped an ollie off the tail of the board.

“Nice job, but try lifting your back foot more, sucking it up into your stomach when you jump.  Also, the reason why your ollies are not lifting the back of the board is your shoulders.  What you are doing is dropping your back shoulder.  It’s a very common problem for beginners.  You need to keep you shoulders level from the set-up to the landing,” Advised Matt.

I got back on the board, put my feet into position, bent down, kept my shoulders level and ollied again.  “Wow!” I gasped enthusiastically.  “That was my best ollie ever.  My wheels were level.  Seriously, I have practiced this for hours and I have never done that before!”

“Yup, that’s because you kept your shoulder level.  I’ve actually got another tip for you, because right now you are ollieing about 4 inches high.  If you want to be able to do tricks like the heelflip and the kickflip, you need to get 6-8 inch ollies,” Matt said.  “Try putting more delay between your pop and the slide of the front foot forward.  Right now, you are too quick, and it’s not giving the board enough time to go high.”

Once again, I following Matt’s instructions.  It was very difficult to break through my mold. I tried and tried, but it was difficult due to months of skating incorrectly.   After many tries, I finally did it!  I put in the delay Matt instructed.  “Wow! ” I said.  “I have never improved this much so quickly.  In just one day, you have fixed my shoulder positioning and now have double the size of my ollie.  This is incredible!”

“It’s very simple.  Many people think of skateboarding as luck.  Unfortunately, they think of us as crazy kids who get hurt all of the time.  The truth is,  skateboarding isn’t trial and error.  It’s ,more exact than that. ”

“It’s exact foot placements and stuff?!”  I chuckled.

“Yeah man.  It is about pressure, timing, foot positioning, and landing.   The mastering of all four in combination can help you master any trick.”

Matt continued, ” Every flip of the board is triggered by pressure to an exact point on the board.  Every trick has a precise foot positioning.   Like this…”  He showed the positioning for a kickflip.

“That’s crazy Matt.  How come know one knows this?” I said.

“People do know this, but it’s mostly the pro’s and sponsored skaters.  Some of them don’t want to teach skaters it because it could threaten their career,” Matt explained.

Wow! I thought.  Matt had just completely changed my perspective of skating in one day.  Skateboarding is a science and


Wow! I thought.  Matt had just completely changed my perspective of skating in one day.  Skateboarding is a science and I was determined to now start trying it taking into consideration his four scientific variables. pressure, foot positioning, balance, and weight distribution.

Over the next few months, I began to progress rapidly.  The more I began to skate with Matt, the more I would learn.   I soon picked up pop shuvits, fakie ollies, 180’s, and then eventually kickflips and heelflips.     Matt shared advice on many tricks and coached me through all of the intermediate tricks.

After three months, I finally boosted my confidence enough to enter the skate park!  Gosh, I had no idea how much fun I was missing.

Matt and I grew close, and I began going to all of his competitions.   For a few months, I watched and noted how to put together a winning competition run.  I noticed that the successful skaters were those who use most of the park, and put together a flawless run of the most difficult tricks possible.

My First Sponsor

Towards the end of the season, Matt convinced me to compete in the competition.  I was nervous because I had never been to a skate park only a few months earlier.  I combined my notes about putting together good contest runs and Matt’s tips to get third place in my first competition!  It earned my a spot on the local skate team.   I earned my first sponsorship!

I was really living my dream!  I was in middle school and most people don’t get their dreams until after college.  It was great.  I went home after the contest and told my parent all about my latest accomplishments.  They received it with a little bit of congratulations, but unfortunately, they weren’t nearly as enthusiastic.    “Do you know that very few people actually make a lot of money in skateboarding?”  my Mom said.

The bitter truth is I am no one special.  There are thousands of skaters just like me.  They all start out in the same place.  Falling, pain, and frustration consumes us, but our desire to progress trumps all.

My advice:  Find someone better than you.  Model them.  Do it for skateboarding.  Do it for anything you are passionate about.

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