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When it comes to skateboarding, few professionals have the longevity of Steve Caballero. Since picking up his first sponsor at 14 in ’78, Steve has become one of the greatest skateboarders of all time and his long list of accomplishments is testament to the man’s talent and longevity. From being an original member of the legendary Bones Brigade to lending his name to the longest running pro-model shoe in skateboarding, Steve Cab’s achievements casts a long shadow, particularly for a modest man who feels blessed to still be doing what he loves everyday. While he was down here for the Vans Bowlarama earlier in the year, he took some time out to chat with me at the Vans HQ down here in Melbourne.

So how does it feel like to have a career that lasts so long, and being able to do something you love for your whole life

I definitely feel super blessed to be able to continue to participate in the skateboard industry. It started out as just a hobby and it turned into you know a sponsorship that turned into a lifelong career. I didn’t really have too many expectations about where I was going to take it – I just kind of did it. Just kept the same attitude, just doing it for fun. Skateboarding has always been a super challenge for me so obviously throughout the years there’s been challenges and obstacles to ollie over.

When starting skateboarding at 12, did you have aspirations to do something else? Like something a bit more normal?

Before skateboarding I wanted to be a BMX racer, and I tried that for a little bit and I just figured that I wasn’t very good at it because of my size, because of how short I was for my age. It was based on age who you compete against, and I knew that I had limitations there because I was so short – my legs were short, I wouldn’t have the speed. It was something that I wanted to excel in, but I knew I couldn’t excel in racing, and then when I picked up skateboarding I realised that it didn’t really matter what your physique was and how tall or how big you were – it was just something that you could progress on your own. It was challenging as well, so I just caught onto that and fell in love with it.

Well, it seems like you still participate in pretty much all the OG and Legends competitions, do you find that you still have that competitive edge?

Always. [Laughs.] I’m a very competitive person, very critical, so when I really get into something, I really try to focus on it and try to understand it and educate myself with everything, and that’s just how I’ve been my whole life. So yeah, I’m still as competitive as I was when I was in my prime.

Well do you think that if that competitiveness were taken away that you would not be that that into skateboarding?

I think the competitiveness that I have within, it keeps me inspired to progress and grow. If I wasn’t competitive with it, with myself, I don’t think I would be able to push the limits that I have over the years. A lot of people skate for fun, but that’s all – they just do it for fun, and it’s not really anything they want to aspire to grow past that, you know? Skateboarding is super dangerous so you have to take a lot of chances and risks, and it takes a lot of courage. People have a lot of fear when it comes to stepping out of the safety zone, so in that sense, being competitive really helps me get past that.

Yeah, well it seems like a lot of the guys from that area are still really pushing each other, like McGill is still out there – Tony, Lance and yourself. Are all of you still very competitive to this day regardless of knowing each other for over three decades?

Yeah, we are… we’re very competitive. We haven’t taken it to a level where it’s really ruined any relationships or friendships – it’s more of a friendly competition. All men are pretty much competitive with each other regardless of what you’re doing. It’s like, you want to stand out you know? You wanna be the best and then some people don’t really care, and they just live their life out that way, I want to go above and beyond who I am as a human being and it takes a competitive edge to do that: to progress and to explore, and to be creative and to push your potential

Do you still hang out with many of the Bones Brigade guys?

I’ve been hanging out with a lot of the Bones Brigade guys lately because of our new documentary that we released last year. I’ve been seeing those guys more recently, and actually after this event here in Bondi, the next weekend I’m meeting up with all the guys in the documentary, plus Stacy Peralta and we’re having a private session that we sold spots to the public through the Tony Hawk Foundation. We sold twenty invites where you can skate with the Bones Brigade team all in one place for a session and hang out. I’m really excited to do that next weekend.

When Stacey first approached you guys all to be a part of the documentary, what was your vibe on how it was going to go?

I was excited for it because I knew it was coming. After he’d made Dogtown, I knew that the next documentary on skateboarding should be about the Bones Brigade and everything that he accomplished with our team and the innovation of bringing still-life to video with skating, our progression in the sport and what we contributed to the industry and the story behind that. But we were kind of wondering how that was going to be told, because it there was so much involved in the Bones Brigade legacy and you only have like 90 or so minutes to try and explain the whole story.

Was it the first time that you’ve heard some of the Bones Brigade members talk about the past? Or have you had a chat with other members beforehand?

You know the first time I saw the finished product, I was just as surprised as any other fan, because we were close…but not close enough to get personal with each other. We all came from different areas of the United States and we come together at competitions and demos, but then we’d go back to our daily lives, so I didn’t really know these guys too personally. When you’re 15 or 16 years old, you’re not trying to interview these guys or figure out what their whole life’s about, you just want to skate with them. It wasn’t till like 30 years later that you get to hear the real background of where these guys came from, what their struggles were. So I was just as excited to see the film as any body else!

The majority of the film revolves around the time when you were a teenager. Is it crazy to think that looking back now at how big the Bones Brigade thing was? Did you realise that it was going to be one for the history books?

When you’re doing something for the pure love of it, not having any expectations of what you’re going to get out of it, you don’t really realise the impact that you’re making. But because of the experience I have as a human being, and being alive for 48 years, I know that every little thing counts so, every little thing that you do is planting seeds. If you sow good things into your life, you’re going to reap good things in your life. And the same thing, if you sow bad things, negative things in your life, it just kind of takes a while for that to all add up, you know?

I just know that everything I do for the industry, for my career – it’s a positive thing. I mean that’s why I come to all these events, and, when I’m with Steve Van Doren,if he asks me to come and visit some shops, it’s touching lives everywhere, you know. I might not feel the impact right at that moment, but you never know where that’s going to lead 10–20 years down the line.

This kind of leads into my next question – when Vans first approached you however many years ago, what was your first reaction to getting a signature shoe

I’ve worn Vans since I started skating, my parents took me to a Vans store, and I bought my first pair of Vans probably around 1977, and then when I got sponsored by Peralta in 1979, they were getting flowed shoes. So from ‘79 to about ‘84, I was getting free shoes, but Vans wasn’t established where they were paying people so I wasn’t actually sponsored by them professionally. It wasn’t until 1988 after all the videos that Vans really wanted to get behind professional sponsorship and they approached me and they sponsored me in 1988. And that’s when I got my very first paycheck from Vans. And at the same time, they asked me if I wanted to have a signature shoe. It all came naturally!

You would have heard the term “Skateboarding is dead” thrown around a few times during your career. Did you ever have worries that maybe skateboarding was coming to an end?

I never really looked at it that way. I’ve been blessed with opportunities to be able to sustain myself in the industry. If you notice in the documentary, towards the end of it, Stacey’s talking about where he wanted to take the company, and where he wanted to take the skaters – notice he doesn’t mention me. He didn’t mention me because that’s when Vans had approached me before the end of that decade of Powell-Peralta in ’88. I was already getting a shoe and I was already making money off the side of board royalties, so when the board royalties went down and when these guys were scrambling at Powell-Peralta, I already had a future with Vans. If I didn’t have this Vans shoe deal, who knows where I might have ended up. I’m still riding for Powell-Peralta to this day, since 1979.