An Interview With Miles Jackson of Cuba Skate


In the skate industry, people like Miles Jackson are few and far between.

For one, he’s educated. But more importantly, he uses his know-how and goodwill to actually give back to the skateboard community. Back in 2010, after studying abroad in Cuba, Miles and his partner, Lauren Bradley, started Cuba Skate. It was just a blog at first, but in 2021 it’s a full-fledged nonprofit making an actual impact in Cuba. Most recently, Madars Apse headed down to Cuba with the DC Shoes film crew to document what exactly they do at Cuba Skate (watch the video above). We called up Miles to chat about the DC documentary and all things Cuba Skate.

The man himself.

Alright Miles, let’s start at the beginning. When did you first visit Cuba?

I first visited Cuba in January 2010 for a study abroad program with the University of Michigan.

Is that when you got the idea for Cuba Skate?

Well, leading up to the trip I had just started skating myself. Just cruising around campus in Michigan. I had done a little research on skateboarding down there and found that there was a skate community but not access to the resources. And so I brought down a few extra boards.

We lived right next to this plaza where a lot of young kids were skating and I just went to practice skating and to practice my Spanish. So, we ended up spending all this time with these young skaters—they opened up their homes to us and showed us their version of Cuba. Like skaters anywhere, they were very smart and knew how to get around, how to talk to people.

After being there three months I fell in love with my partner Lauren, who was also studying abroad there. When we came back to the States we felt this burden to do something to help. And that’s when we first launched Cuba Skate, just as a blog to try and get the word out. Then we start doing some little fundraisers. And that led to us actually starting Cuba Skate and going back just five or six months after we had finished our study abroad.

Starting them young. Photo: Arto Saari

Wow, so you’ve been involved with Cuba for over 10 years. 

Yeah, we started by getting a bunch of product donations. We’re lucky to have a number of partners, skate shops, skate companies, pro skaters, friends, volunteers, and even study abroad students that wanna help and make donations. It got to the point that my apartment was just so full of product that I even had to store stuff in my parents’ basement. But, we couldn’t really get it to Cuba because you can’t just ship stuff there. Customs can be a real headache.

So, we took advantage of volunteers and study abroad groups that were going to Cuba and they would do some type of program with us. We would send them product that they would take into the country and they would do some type of cultural exchange with Cuba Skate. They’d help build at the DIY or they’d check out our wood shop.

We also took advantage of this program that Airbnb has called Social Impact Experiences. Travelers could pay for an “Experience” where they’d meet with our staff and skaters at the wood shop in Havana. They could have a cup of coffee, get a unique look at life and skating in Cuba, and even do some woodworking.

Madars Apse helping to build a DIY for Cuba Skate.

So give us a little behind the scenes of what it’s like actually getting skate gear in Cuba.

Before Obama made the changes allowing travel back and forth, I would arrive in Cuba with five or six bags and I’d have to pay hundreds of dollars to customs agents so they wouldn’t take the gear. They just thought I was gonna sell it. They don’t fully understand the scope of the nonprofit because everything in Cuba with Communism is more government run. When I first went I would either have to take the train up to Montreal or fly to Toronto, and fly from Canada. Or go from DC to Miami to the Bahamas, and then fly to Cuba.

‘It got to the point that my apartment was just so full of product that I even had to store stuff in my parents’ basement. But, we couldn’t really get it to Cuba because you can’t just ship stuff there.’

We learned the hard way not to bring too much at one time. When you’d fly from Miami to Havana you’d have to pay per pound, even for your carry-on because so many people are bringing things down to Cuba because there is such a shortage of supplies and lack of resources. So when Jet Blue opened up flights to Havana, I’d just stuff my checked bags to be exactly 50 pounds. Then I’d load my backpack as big as possible with wheels, bearings, bushings, and smaller things like that, and carry five or six skate decks in my hands.

Miles and the crew regularly clean trash to prove that skaters are positive members of the community.

That sounds like a typical skater’s DIY approach?

Definitely. But, it was more challenging when I brought down the wood skateboard press. I had to buy a ticket for a friend and he helped bring it down. So, essentially you gotta be a mule. And as the director I wanna be shaking hands, meeting higher-ups, and getting donations from philanthropists. But, I still have to get my hands dirty.

But, is there less of that now that Cuba Skate has a little more recognition?

Yeah. I mean, we’re a cultural youth development organization and we operate in compliance with both Cuban and American governments. We’ve been apolitical and we haven’t associated with either side. But, it took us a while to get permission from the American State and Treasury Departments to travel back and forth as a humanitarian organization.

‘Before Obama made the changes allowing travel back and forth, I would arrive in Cuba with five or six bags and I’d have to pay hundreds of dollars to customs agents so they wouldn’t take the gear.’

Through your eyes, how has the skate scene progressed?

It has progressed a lot. Being able to bring more products into the country led to a growth in the skate community. Now you see more kids skating. In 2010, when we first got there, you saw maybe a handful of people skating and it was a very tight-knit, small community. Now those communities have just blossomed and grown tenfold. Now there are skateboarders in the provinces and in every neighborhood of Havana. A few years ago, if I was skating down the street and saw another person skating, I knew who he or she was. But now, I’m just amazed by how many young kids there are riding skateboards.

And on the same note, the level of talent is pretty special considering the circumstances. You know if you’re jumping down a 10-stair time after time, the boards break, the shoes wear out, things like that. So to see that growth and progress given the unfortunate circumstance of not having any skate shops is really remarkable. Because these young men and women are really excelling even though, if and when that board breaks, that’s it.

Local skater at a Cuba Skate DIY.

That is crazy to think about. If your board breaks, you can’t just head to the local shop to set up a fresh one. Is there anybody making boards in Cuba?

No, we have the one and only skateboard press. Which is pretty cool, but we still have to bring in the maple veneers from Canada.

That’s amazing. The only press in the whole country! So, how do you distribute the product to the Cuban skaters?

We’ll have merit hours. So, if you want a new skateboard, you have to build at the DIY for a few hours and that will get you whatever you need. You put in time, and we’ll make sure you have stuff to skate. But, you have to bring your broken board because we don’t just want a couple kids to have a bunch of boards. We also do contests and give skate product as prizes. If you want younger kids to start skating, you can’t just give them a shitty hand-me-down, you have to get them a legit setup.

‘In 2010, when we first got there, you saw maybe a handful of people skating and it was a very tight-knit, small community. Now those communities have just blossomed and grown tenfold. Now there are skateboarders in the provinces and in every neighborhood of Havana.’

So the skaters you first encountered on the streets before you founded Cuba Skate… how did they get gear?

Well, essentially every other country aside from America has been able to travel to Cuba over the years. Surfers or skaters would come to town with their skateboards and see the skaters at the local plaza with their boards just fully blown out. So, they’d leave their boards with the locals before flying home. People are always kind and generous in that regard.

What about shoes? Can you buy skate shoes in Cuba?

It’s not like the new DC Kalis shoe drops and you can go order them on Amazon. That doesn’t exist whatsoever in Cuba. But skaters have most of the main brands, but you’ll see shoes we haven’t seen in America for years. Sometimes they’re from brands that aren’t even around anymore, but somebody got them somewhere and brought them to Cuba. There’s a lot of travel between Cuba and South America, and some people with special visas will take empty suitcases and come back with it filled with some random product, like last season’s Ed Hardy tees, or something like that. The same thing probably happens with skate shoes too.

‘If you want a new skateboard, you have to build at the DIY for a few hours and that will get you whatever you need. You put in time, and we’ll make sure you have stuff to skate.’

How is the internet down there? Are kids able to stay up to date and watch the latest skate videos?

The Internet just became much more available in 2015. You’d buy an internet card for a couple dollars per hour, but it’s not great for uploading or watching videos. But, now people can access more content on their phones because they have faster internet, but they have to pay quite a lot because they charge per gigabyte. It’s not like they pay a monthly plan for unlimited data.

There’s also this underground thing called El Paquete. Basically, people travelling back and forth from Miami will bring a hard drive full of whatever happened that week in anything. In the NFL. In skateboarding. Then it gets dispersed to different people in the community. Then they go door to door selling the content, whether it be the latest album, sports highlights, or even skate videos. It’s really interesting, you should look it up.

A skateboard can change someone’s life.

That sounds crazy…. definitely need to check it out. So far, what accomplishments are you most proud of?

The best accomplishment is giving the Cuban skaters the resources to solve problems on their own. As opposed to just giving them skateboards, they built a remarkable DIY skatepark… they built it. And in the wood shop they’re now repurposing old boards into cruisers and making souvenirs like rings out of old decks. I’m also really hyped on the recycling programs. We’re even trying to build a skatepark out of 100-percent recycled plastic, which I think would be the first in the world. Skateboarders doing good for the environment is just part of who we are.

I’m also proud that we’ve helped grow the female skate community in Cuba. We’ve been focusing on that specifically over the last few years and we’ve had some female pro skaters come help. I can teach a girl to skate, but it’s good to have a teacher who looks like you and who you can identify with.

‘We’re even trying to build a skatepark out of 100-percent recycled plastic, which I think would be the first in the world. Skateboarders doing good for the environment is just part of who we are.’

100 percent. For anybody wanting to help out, what’s the best thing they can do to help out Cuba Skate?

Financial donations are obviously important because we’re a small organization. Delivering the goods and running programs costs money. And people used to donate their old stuff. We still appreciate it, but now we’re at the point that brands are willing to give us new gear. So, I always say that if you want to support Cuba Skate, you should take the trip down there. I’ll put you in touch with our staff so you can connect and see the importance of the work we’re doing. But also it’s not just about bringing down skateboards and shoes. It’s about bringing down tools, wood presses, gloves, shovels—things that help the locals in a more sustainable way.

So, where do you see the future of skateboarding in Cuba?

I think in order for skateboarding to thrive in Cuba the wood shop needs to grow and there needs to be some sort of cooperative. It was always our goal to build out a little Airbnb-style house where we could host travelling skaters who would bring gear and help out. And there needs to be an official skatepark, and there needs to be government recognition.

We all know the life skills that skateboarding can teach you, and the parents of Cuban skaters—who had never even seen a skateboard in their life—seem to appreciate it too. They see their kids falling down and getting back up, and the value in that. But we need to get the Cuban government to recognize it.

We‘ve been fighting for years to get an official skatepark. We’re trying to work with the Tony Hawk Foundation to bring them down to build something. The DIY has been great, but I think the best bet for skateboarding in Cuba is the Olympics. Seeing that Cuba is very competitive with fellow Latin American countries—they have the most gold medals in all of Latin America but they still see skating as part of American culture.

‘We all know the life skills that skateboarding can teach you, and the parents of Cuban skaters—who had never even seen a skateboard in their life—seem to appreciate it too.’

That’s interesting because we can be so cynical about skateboarding in the Olympics, but it’s hard to argue against it if it helps bring new skateparks in places like Cuba.

That’s the way it is. Cuba doesn’t have the privilege of having a bunch of skate shops and parks like we have in the US. So, the Olympics presents skateboarding as an official sport and maybe that can be the final push that gets the government to support it.

So this DC film shows Madars Apse skating and very much participating in all things Cuba Skate… how was that?

It was great. I didn’t know Madars spoke Spanish. He really engaged with the people, went out every night with us and partied. His energy was just really fun to be around. He did some crazy tricks and did an NBD at the DIY that the kids were really hyped to see. It’s great to bring pros, but I’d rather bring an amateur skater who can’t do shit on a board, but will mix cement and do woodworking with us—Madars did all that. He got his hands dirty and immersed himself in our community. And that’s what’s most important to me.

Miles with that Cuba Skate x DC shoe!

Donate to Cuba Skate at cubaskate.org/donate. Cop a pair of the DC x Cuba Skate collab here.

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