Mr. Cole, do you remember the first time you got paid to skateboard?

Oh man. It had to be some sort of contest. I skated every local contest back then – which wasn’t very many – all the way out to New Jersey and New York and middle Pennsylvania. I never wanted to be the guy who jumps the gun too early – I didn’t want to start travelling long distances to skate contests before I had won everything. I wanted to win every local contest first. I wanted it to reach the point where if I showed up, people would be like “Oh, crap,” and just be fighting for second.

Today you are arguably the best technical skateboarder in the world. Where do you find the discipline to accomplish something like that?

I did it because that’s what it was going to take. I really wanted it. I had an older brother, and he was bigger and smarter, and when you’re a kid, you’re trying to catch up all the time. I think that that’s where it kind of came from, just that little brother syndrome. I was just trying to be something, trying to make myself worth something. It was proving it to other people and proving it to myself at the same time. I needed that.

You must be a very competitive person.

Sure, but you also have to find the fun in it. Especially in the science part of it, the physics thing: “Okay, what made the board do this?” And then you try that. If you can find the fun of trying, that’s when you’ve really won in skateboarding. If you only find fun in landing the trick that’s a lonely place to be. You’re only going to land it once in a blue moon.

What was it that initially drew you to skateboarding when you were younger?

It relaxed me! I just recently had surgery so I’m not skating at the moment, but skateboarding is still a pretty big release for me so to not have the option of skating is pretty tough. I still need it to keep myself sane in a way. As a kid, I had a lot of energy; I had to take medicine to go to sleep and stuff like that so I needed to get that energy out somehow. I filled my childhood with other things, like riding a bike and playing football, but skateboarding… skateboarding had it all.

What do you mean?

You set your own goals, you had your own list of accomplishments to achieve every single day, so you were always busy. You had those little take-homes, where at the end of the day you’re just like, “Man, I had a great day.”

Plus it’s a sport you can do on your own. You don’t need a team or anyone else to fully enjoy skateboarding.

A lot of people don’t skate by themselves. And I think that that’s really weird! To never experience that? If that’s the case, then any other sport would suffice. It wouldn’t have to be skateboarding. It only takes one to party, which was great because back when we were kids, you didn’t have cellphones. You weren’t able to text somebody and find out where they were at that moment.

The circumstances have changed a lot.

Yeah, I remember it being so depressing when you would think that you were going to have a whole day with your friends and you just couldn’t get a hold of them. You called them on their house phone, and if you didn’t get them – that’s it, you were alone! Oh man, what a bummer it was! (Laughs) But at the same time I feel like technology kind of ruins a huge part of growing up, like when you have to ask someone to a dance or ask somebody to hang out with you. It was a terribly nerve-wracking experience where you were really going out on a limb. That vulnerability is something that you can take with you throughout your life.

You don’t have to make yourself very vulnerable to send a text message.

Right, and you need those awkward experiences to overcome. If you don’t have anything to overcome then you remain less-than, in a way. Now it’s just a perfectly worded text message and a whole campaign of, “I’ll start liking her photos here and there, leave a comment here and there,” for the first two weeks or so. Then the comments get a little bit longer, she’ll respond, and everything is absolutely wordsmith perfect! If text messaging were dating, I’d seriously be a Casanova. But I wasn’t brought up that way.

You also used to skateboard by yourself because growing up in rural Pennsylvania there weren’t any other skaters that lived near you, right?

Yeah, back then, if you saw a kid with skate shoes, it was like, “Oh, my God! You skate! We’re friends now!” (Laughs) It was like finding a diamond in the rough, like getting lost in a desert and seeing another person. “Finally I found you!” It rarely ever happened!

That kind of isolation must have affected your skating ­– you’ve said before that you thought you invented certain tricks because there was no one else skating around you.

It was like I invented the wheel, but the wheel was already invented on a different island. (Laughs) It’s funny, you do feel sometimes like you’re just forging for yourself. You don’t know what other people are doing. For example, I knew what a boardslide was and I knew what a 180 was, but I never saw anybody do a lipslide. I thought I’d invented the lipslide! Eventually you grow to find, “Ah yeah, somebody already did that.”

But today, with the Internet and the popularity of skateboarding, that is completely lost.

I don’t know. Nowadays, you’re making up stuff and it’s like, “Well, I’ve never seen anybody else do it. But it’s probably out there.” Chances are they did it in the nineties or somebody on YouTube has already done it. There are tricks that nobody does in the spotlight because there’s a random kid in Texas that does that trick. He has it, but he doesn’t have the outlet to get it in front of everyone’s face. He can put it on YouTube, but no sponsors are making ads of it and things like that. And so, you really are inventing it for yourself, in a way, and you always were.

Has there ever been a time when skateboarding felt like a job?

During contest season it’s tough. All eyes are on you and you don’t want to go out there and look like you don’t give a crap. And the contest season isn’t just walking into the arena, it’s also every skate session before that. It’s really hard to get your mind off of contest skating, even when you’re just skating for fun. It’s also been tough since I joined with Street League. If you’re signed on with Street League, you can do a couple other contests during the year – but that’s it. It provides you with great opportunities, but that comes with certain sacrifices. As a result you have people being like, “Well, skateboarding is skateboarding, you should be able to do whatever you want.”

In the end it is how you make a living as well though.

Yeah. There will be a lot of people on message boards who will attack pro skaters for their decision-making or for skating for this company or for money and things like that. But you still have to work for money, right? People shit on you for that. You’re like the lamest person ever.

Even though you share the love for the same sport and you could have actually sold out a long time ago.

Exactly. I obviously know how to make spots unskateable, if I were some complete son of a bitch like these people are treating me. I didn’t throw in the towel; I didn’t sell out skateboarding. And neither did any of these other guys who took sponsors that pay them for what they do. It’s just we now get to provide for our families with the thing that we love doing more than anything ever.

Which in the end paves the way for other kids who dream of making a living doing what they love.

What people don’t understand is that skateboarding’s popularity is growing because of these big sponsors and because of these contest series; so it actually means that you’re able to get a skate park in your town easier than you were ten years ago. Now you have a place to go skate, and a lot of times these bigger sponsors are throwing in money for that. And these are foundations made by skateboarders that are making a lot of money from the sport. But that anger just comes from a love for skating. And that’s actually pretty cool, that people love it that much and they hold it that dear.