Last year saw Vans celebrate its 50th anniversary, and this year is the 25th anniversary of the Half Cab – how have you seen the brand and team change as the years have gone on, and how did it feel to be part of a massive project like Propeller?

Well over the years I’ve seen skaters come and go, some have lasted a while and some haven’t. The team’s constantly changing all the time…but I’ve seen the brand go through different changes and phases as well, from the vulcanised to the cup sole and back to the whole vulcanised look again. I’ve been at a company where probably three or four different CEO’s, different designers, different shoe styles…but what I like about what Vans had done was get back to the roots of their industry – the product and the look.

You start out with a look, then other competing brands come in and you start to try and mimic them because you’re competing against them; you can forget your roots. But Vans figured out that, if they went back to their original look, that would attract not only the people who made them who they are but also make them stand out. I think they’ve done a good job with that.

And do you think that has come from Vans listening to the skaters?

I believe so; I think that every time Vans has listened to a skater, they’ve benefited from it. Obviously with the Half Cab…my shoe came out in 1989, from 1989 until 1991 I saw people cutting my shoe down. I started doing it myself but after my third pair I was just over it and was like “Why don’t we just make them like this?” So I called Vans in 1991 and was like “Hey, I see this huge trend in my hi-top. We should make them like this rather than have people having to cut them down all the time and we’ll call it the Half Cab.” Because I listened to skaters and Vans as a company listened to me as their skater, 25 years later here we are still selling the Half Cab. I always wonder what it would have been like if they didn’t listen [laughs]. But the fact is that they did listen to what I wanted, which is cool.

When Rowley got on the team and he made that whole shift towards bringing them back to the classics, the Half Cab was part of that line as well which helped to bring that back to life. So yeah, I think that the times that Vans have listened to their skateboarders then they’ve benefited from it and they still do. The Vans video Propeller video was such a long time coming because they listened to skaters saying that they should have Greg Hunt come in to put the video together, and he produced a beautiful piece for Vans first video.

You’ve also stuck with Powell since the beginning. Such longevity with single brands is almost unheard of, how have you maintained such close ties with these companies?

Well like I said before, I think it really depends on the individual and their personality. I feel like I’m a pretty loyal person if the company stands behind me. Every business deal is a relationship and you’re going to have your ups and downs, when it comes to Vans or Powell it hasn’t always been good times. There’s been bad times, slow times, those times when I didn’t even have a model for Powell but I stuck with them.  I probably could have got a model from another company, but I stuck with them and said “OK, if right now the industry doesn’t want to see a Caballero model then that’s fine.” Sticking with them, I have a model today and the fact that I have this history with them – the reissues sell really well from the 80s.

Same with Vans; I’ve had pay cuts, in the beginning I had a really terrible contract but I sold a lot of shoes. Once they changed CEOs and broadened their market overseas I changed the contract so it benefited me more, then just before Rowley came on I got a huge pay cut…which I’m sure helped fund Rowley’s whole programme. But in the end that benefited me, it helped Vans bring the Half Cab back to life and it’s still selling well today. Sometimes you have to make sacrifices you know – you have to work with the company, if they’re not doing so well then maybe you don’t get as much. But I know for a fact that when I have stuck with companies through the low times, in the high times I’ve benefited. I think that’s how you have longevity with a company and I can say that I’m probably the only skateboarder to have such a long relationship with both a shoe and board company. That’s because I’m not trying to go for the big bucks, if the company is suffering then I suffer with them.

The 90s and the accompanying explosion in street skating saw a lot of vert skaters calling it quits. You pretty much reinvented yourself and kept up with the handrail chomping new breed, but how was it living through the ‘vert button’ years?

With vert? Well I just kind of adapted to my environment, which was the people I skated with then being street skaters. Instead of going against the grain I kind of went with it and it really sparked a new feeling with my skateboarding – I felt like I was relearning to skate again, learning all these flip tricks and skating with different people. But from time to time I’d try and find a vert ramp here and there, try to keep the skills up. There was a time when I was driving every weekend for two hours just to skate vert, just to keep in tune with it and not lose tricks. It took a lot of dedication to keep continuing trying to find places to skate vert, but in the meantime reinventing myself and learning street tricks. Just trying to do the best I could, focus on my strong points – I felt like I still had something to offer you know, at age 35, going down handrails. You know, just trying to adapt.

But then after 2000 more parks were being built, bowls were being built so I kind of put the street board away and started skating more vert and bowls again. I’ve been focusing on that for the last decade, but here and there I’ll bring my street board out and try to do something to excite people. There was a time in the late 90s and early 2000s when people didn’t know that I skated street, they just remembered me from the 80s and now. So sometimes I’ll try and see if there are still some street tricks in my memory banks. It’s definitely two different types of skating and takes two different sets of muscles to perform…but it was fun. I had a really great time making that transition, they were great times.

Playing with The Faction saw you pretty much at the forefront of the Skate Rock scene – who were some of your favourite bands from that scene?

At that time I would say that Minor Threat was a huge influence, the Descendents, Social Distortion, the Misfits and Metallica. Those were the bands I really liked in the early 80s and they influenced our music a lot. But the band that influenced me starting The Faction were JFA – they were one of the first punk rock bands that I knew skateboarded and they influenced and encouraged me to start a band. Then we ended up playing up lots of shows with them!

How was it seeing the Chin Ramp rebuilt last year, and getting to skate it after so long? And how hard was the recreation of the classic ‘four inverts’ photo? From the edit of that session, it looks as if it came together pretty fast…

It was very difficult actually. The fact that we were trying to recreate something that we had just done, you know? I think it’s a lot harder to recreate a photo than to just shoot it how you’re supposed to shoot it and let it come out the way it wants to. When you try to recreate something you’re nitpicking, because you’re trying to duplicate something you did 30 years ago. The same angles, everyone with the same timing…so many factors, the lighting, everyone dropping in at the same time. So it was definitely a lot of pressure, but we pulled it off and I think we did it pretty well.

It was a lot of fun getting together with everybody and having those skate sessions together, trying to refigure the ramp out and relearn stuff we did back then alongside trying to do new stuff that we’d never done on the ramp. It was really neat to do that. It was just really exciting to get together, it felt like we were filming the Chin session again. Once we’d knocked out the invert photo then it was just kind of a free for all, we were just like “Try this, try that.” We actually ended up doing four frontside inverts together! That was just a thought, we got a photo of that too.

And everyone’s skating as good as ever really…

Well…at least Tony is. We’re still struggling [laughs].

How has it been seeing the new generation of vert skaters – Tom Schaar, Lizzie Armanto, Clay Kreiner etc. – getting stuck into it?

It’s amazing! It’s amazing to see how comfortable they are. I was just admiring this weekend at the El Gato classic, we had the ‘Generations’ contest where each team included an amateur skater, a female skater, a pro and a legend. There were six teams, six on each so 24 skaters and just watching each group was just amazing; seeing how much the women have progressed, seeing the little amateur guys coming up. This kid Gavin, he’s ten years old but looks seven, spinning 540s and doing crazy vert tricks, it’s just inspiring and encouraging for people. Then watching the pros, how consistent, stylish and comfortable they look. Obviously we were the last ones to go, we’re still skating in our 50s. It was really cool, I think that skateboarding is in a really good stage right now and the future looks really bright.

Carrying on with the Bones Brigade theme, can you tell us a bit about how the documentary came out? How satisfied were you with the finished film?

I think it was a pretty amazing piece that Stacy Peralta put together. It told an amazing story, a team that he put a lot of time and heart into. The stories that were told…a lot of people became really transparent when that documentary came out and there was a lot of cool things that I never even knew. So I was kind of looking at this film as someone that was discovering new things, but about the guys that I grew up with. We didn’t all live in the same area so I didn’t know their backgrounds, but when you’re seeing interviews with people and hearing these stories then you start to discover stuff you didn’t know about. About all aspects; Rodney Mullen, McGill, stuff about Lance, when he was growing up. Tony, the struggles he went through… It was a really neat experience all around and I think it really showcased a decade of what the Bones Brigade offered to the industry and what we accomplished in those ten years from 1980 to 1990. A lot of moves were invented, a lot of inspiration…Rodney you know, he created an industry that wasn’t there before and that’s huge! We created tricks, he created an industry, which was pretty amazing.

The fact that Stacy was able to see the talent in these people and put it together as a collective…and not so much just manage a team but also put out the best products and try to figure out creative ways to advertise the team. All the travelling, everything we did, all the competitions – we had a really, really great opportunity to be a part of something which helped inspire new generations. We were at the forefront of showcasing skateboarding to the world and because we had so many different creative elements to the company, we were able to capture moments which were very meaningful to people and which still to this day bring back fond memories for people. I think that documentary captured the essence of what skateboarding then was about.

To close things off, who has your favourite frontside invert of all time?

My favourite frontside invert? Shoot! I just saw one of Ronnie Sandoval, that was amazing. It was a slow motion clip of him doing one and it was very stylish, just the way he did it. But you know just watching the inventor Eddie Elguera, who’s 54, still do them with amazing style – it just looks so smooth – that’s what inspired me to do them, watching him. This last weekend, seeing him perform that trick is beautiful to see. The fact that he’s two years older than me and can still do it, it’s amazing. I hope I can still do them in two years!