Jessyka Bailey's "Ruining Skateboarding" Interview by Jaime Reyes

JessykaBaley NYC SamMcGuire DZPhoto: McGuire

When Jessyka’s crew quit skating in Arizona, a move to NYC reignited the spark to stack clips and make new friends. Jaime Reyes hops on the line to get the skinny on this awesome journey—from the May ’22 issue of the mag.


Jessyka handled business from AZ to NYC and got the THERE pro model to show for it. Don't miss this part

Hi, Jessyka. How are you?
I’m doing good, just chilling, drinking some coffee

Where are you from?
I’m from Phoenix, Arizona. Phoenix is sort of like LA where there’s a lot of smaller cities surrounding it. I’m from the Tempe area.

Did you ever skate with Nika Washington?
No, Nika is from Phoenix proper. I grew up about 30 minutes from where she’s from. Erik Ellington is actually from Tempe.

I thought Ellington was from Alaska.
He might be but he went to high school in Tempe. Every time we see each other we have the same conversation: “Oh yeah, you went to the same high school as my dad.” And then he asks me, “What year did he graduate?” And I’m like “Dude, there’s no way you were a part of his graduating class.”

Could he be, though? How old is your dad?
Well, I’m 32, so he’s like 60 something.

Oh yeah, I don’t think Ellington is that old. So what got you into skateboarding?
I started skating because we were moving around a lot when I was 16. I moved to a different part of Arizona and I didn’t have any friends. My brother had a skateboard, so I just stole it and he got super pissed. He was like, “You’ll never be able to skate!” And I was like, Alright, dude, I’ll show you. But then we ended up becoming really close and he would drive me around every Saturday and we would skate every skatepark in Arizona.

That’s awesome. Does your brother still skate?
No, he doesn’t skate. He was born with spina bifida so it was kind of a miracle that he was doing the drops that he was. He would ollie into ten-foot bowls and shit, you know? And he has a rod in his back and if it broke it could literally kill him, so my mom was always really protective of him when he was younger. But once he reached 18 he just did whatever he wanted. But as he aged his spina bifida prevented him from continuing his journey.

jessyka Bailey Switch Flip GIFAmazing nollie backside flips just like Ellington, must be a Tempe thing

Well, at least he got to skate and you got to grow up skating with your brother. That’s awesome. So you’re 32 and you started skating around 16 because of your brother. Who was your first sponsor?
I tried for a really long time to get sponsors. The Arizona scene was just not really having it, and then finally I met this skater and his parents owned a skateshop in Mesa, Arizona. I remember they were from California and their names were Jim, Bob and Heather. And this dude had a bald head and goatee and just looked really gnarly. I was like, Dang, dude, these people are so sick. So I would just go there all the time and they were like, “We want to sponsor you,” and that was my first sponsor ever. I think it was honestly called BBQ. They were literally only around for about a year and then they went under.

Well, shit happens.
Yeah, it’s a hard market.

Who are you sponsors now?
I am flow for Vans, Mob, Spitfire and some Deluxe stuff. And then I skate for KCDC skateshop and obviously THERE skateboards.

So you’re a college graduate, correct? What did you study?
Yeah, I graduated from college. I have a degree in fashion marketing. Basically what I learned is how to build websites and everything about fashion, but mostly just how to use Adobe Illustrator and everything that comes along with starting a business—from scratch to it opening its doors.

So if I need any business tips I can hit you up, right?
Oh, I could definitely give you advice, especially regarding websites, search-engine optimization or any computer stuff.

Alright, you’re my girl. So what made you move out to New York?
It was just a dream of mine for a really long time. I always wanted to live out here. When I was younger I was like, Oh, I’m gonna move to California. But then I went to California and it’s so close to Arizona. But I kept going there and I was like, I don’t really know if this is me. Then it was just like, I’m just going to move to New York. I was trying to do something with my degree, and honestly moving to New York from Arizona was just a huge eye-opener.

I’m happy you moved to New York. You know, I met you on Mulberry Street in New York. Do you remember that?
Yes, I do remember meeting you. I remember showing up and you were with Leo. I was like, Oh my gosh, both of my heroes are here right now. I recorded the entire panel you guys were doing and was like, This is the coolest thing and the closest I have ever been to anybody I look up to.

There Jessyka Bailey pullquote I started skating and honestly, it revived me"
Let me see that footage!
Now I’m gonna have to go through and find it. I’m not lying. I still have it on my phone. I don’t delete anything.

That’s rad. Were you stoked when you moved to New York to just go skate everywhere?
Actually, I’m not gonna lie—I don’t think that I was really skating that much because I guess I felt really discouraged skating in Arizona. I got to a point where every single one of my friends had stopped skating, so every time I was going out I was going alone. So when I moved to New York I was not really skating, you know? And what happened was I started this internship where I was basically working 30 hours a week for a 200-dollar stipend and I was literally going crazy. I was like, I can’t do this anymore. I just started getting really in my head. I didn’t have any friends and I feel like that just happens to everybody. And I was like, Dude, I just need my skateboard. So I started skating and honestly it revived me; it awoken me.

I feel like skateboarding has done that for a lot of people, because I stopped skating for a little bit and Jeffrey also stopped skating for a little bit. But we all go back to skateboarding. That makes me happy.
Definitely. I mean, skateboarding is honestly our happy place.

Skateboarding is the best drug
It is; it really is.

So you started to get back into skating while being in New York. Who did you start skating with?
I just started going to skateparks alone.

JessykaBaley SwitchFSFlip NYC SamMcGuire DZJessyka switch frontside flips above her happy place     Photo: McGuire

That’s okay. Solo missions are all good. That’s how you make friends.
Yeah, I was solo missioning it almost every single day when I got off work and I just started meeting people. And there were a lot more female skaters out here—more than I’d ever seen in Arizona. It blew my mind. I was like, This is so insane. This is so awesome. Can we be friends? Am I coming off too strong right now?! But yeah, I made a couple of friends and we just started skating all the time. It was great times.

I’m stoked for you—stoked you’re in skateboarding and stoked to watch you skate.
Aw, thank you. I’m stoked to skate.

Do you still have a nine-to-five day job or do you just skate?
No, I wish. Are you kidding? I wish I could just skate. I work at a Michelin star restaurant in SOHO and it’s literally so much. I didn’t really realize when I got the job, but when you’re working in a Michelin star restaurant you are working with people who that is their career, you know? Whereas before I was working at a restaurant and everybody had something else going on. I was working with actors and performers who were running around singing. Everybody had something going on but at this job everybody is just like, This is what I do. And that’s super cool. I appreciate that but it is a lot of work inside and outside of the job.

What restaurant do you work at? I love fancy restaurants; I love to treat myself.
This one of three Michelin star restaurant with a female chef. It’s called The Musket Room. The chef is queer and it’s really sick, so I was hyped to work there. They have a female Black pastry chef and that’s just really unheard of in food, which is insane because I’m like, How have men even dominated this space when women have always been cooking? So it’s really cool that a woman runs it.

So you wait tables?
Yeah, I’m a server; I wait tables. It’s good money. I only work two or three days a week.

I’m looking at the menu right now. When me and my wifey come out to New York we need to eat there because these scallops look amazing. Oh, and the oysters too.
Some of that stuff isn’t on the menu right now because it’s seasonal. It’s a prefixed menu, which is pretty cool, so you get seven courses. I’m really selling you on this right now.

So you work two days a week and you get to skate a lot. That’s amazing. You mentioned your girlfriend earlier. How long have you and your girl been together?
We just had our five-year anniversary. I met her in Arizona a month before I left and I was just like, This is the best person I have ever met in my entire life. I need to give this a shot. And we did and we’re still together.

Jessyka Bailey backsideflip Sun City Banks Ben BravenecBackside flip from high to low in Sun City    Photo: Bravenec

Rad. Is she psyched on your skateboarding? Is she supportive?
Of course. One-hundred percent. It’s great. She doesn’t skate and she has her own interests so we can vent to each other about our things that we’re interested in and our struggles. And she’s just really supportive and kind of the opposite of how I am—she’s really calm and articulate and knows how to communicate her emotions, whereas sometimes I’m kind of all over the place. I’m like, I don’t know how I feel right now. Ahh!

I think that’s every skateboarder right there—all over the place. Because I have that. My wifey, she’ll ask me something and I’m like, I don’t know; whatever you want. What’s your favorite trick right now?
This isn’t even that cool of a trick, but I’ve been doing nollie backside disasters on transition but I hadn’t been bonking the nose—I’d just been doing the pivot version for so long. I finally learned how to bonk the nose and I’m like, Dude, this feels so good. It’s one of those tricks that feels really awesome.

Yeah, sometimes the simplest tricks are the best feeling tricks ever.
That’s how I’ve been feeling. I’m like, Okay, I’m gonna do this 100 times today. I just love the feeling.

Who are your favorite skaters or what’s your dream skate session?
This probably changes weekly because of Instagram, but for a dream skate session, probably Carl Aikens. I really like the way he skates. I wouldn’t even be skating because these are people I would sit down and watch. Obviously Leo Baker. I just really love watching him skate. But a dream session where I’m actually skating—probably the THERE team, just vibing, hanging out, chilling. That’s the dream. But I have so many people that I look up to that I can’t even think about it right now and it really does change weekly because of Instagram. I’ll be like, Oh, I found this new person. I just found out about Ronnie Kessner. He’s amazing. He skates goofy foot so I’m gonna follow him and look at how he does tricks.

What are you working on right now?
We’re finishing up the THERE video, so we’re filming that. But then I think we’re gonna work on a spring and summer video for out here in New York. Almost like a Bottom Feeder-type of video. I’ve been talking to Abi, Sam and other queer skaters out here and I think we want to do a really short East Coast video where it’s super creative and really vibey and shit—and the skating is good.

Do you like filming?
Yeah, I do. It’s fun. I never did it when I was younger. We just always went to skateparks. Everything is really spread out in Arizona so you couldn’t just be like, Oh, let’s go skate at this spot all day.

There Jessyka Bailey pullquote I just wanna work out and be filming for my next part
What does it mean to you to be a pro these days?
My only idea of what a pro is supposed to be like is what Leo Baker is like. Leo lives the life. He’s always filming his next part and working out and—dude, that’s literally my dream. I just wanna work out and be filming for my next part. That’d be so sick.

Do you think Instagram or social media in general has changed the game in skating?
It 100 percent has changed the game. Without Instagram we wouldn’t be as far and skateboarding wouldn’t have been forced to change, you know?
 
Tell me about the day you switch flipped the grate at Flushing.
Well, that was my third time being there. Every single time I would fall. It was a really frustrating day because we just needed to get it done. I felt like I just had to land the trick. I landed it and—you know when you’ve just tried something so much that it just doesn’t even feel real? It’s so built up? I was just like, Oh, okay. Let’s go. Bye.
 
So you were not stoked? I would have been stoked!
I was stoked but I was just like, That’s it? That was the feeling? Okay. Flat gaps are weird. They’re weird and they don’t feel good. It’s not like when you ollie down something and you land, crouch and control it. I felt like that gap controlled me; the speed was controlling me. I don’t know how to describe it. It was just a really weird feeling.
 
Jessyka Bailey Switch Flip Flushing 750
Skaters are their own worst critics. This switch flip at Flushing rules
 
Hey, but the photo came out sick.
Yeah, I was really hyped on the photo. It was really awesome. I saw the photo when I was on my way to work. I was like, Okay, dude, I need to find this Thrasher mag. I’m getting this magazine. So I’m in SOHO. I went to Icon Magazine; they didn’t have it. I went to Noah; they didn’t have it. I went to Supreme; they didn’t have it. I called every single skateshop in New York. I told Maria to go to every skateshop in Arizona and call skateshops and nobody had that magazine. It was all sold out so I had to buy it online.
 
You should have called me.
You had it?
 
Yes, I did. And I would have connected you with the right people to get it, too.
Dude, I needed that connection in that moment. But I was like, I want this now. This is gonna get me through this shift. And I didn’t get it but it was fine. I ended up getting two of them, which I’m really stoked about.
 
Will you sign my copy when I see you next time?
Of course. I’d be honored, honestly. I have to get your cover—that 360 flip.
 
Good luck finding it. 
I don’t even know how I’d be able to find it. Maybe I could go on eBay or something. I bet somebody has it. Have you tried looking for it?
 
I got a copy to donate to the Smithsonian. I was asking everyone, like, Dude, how do I get a copy? I talked to the dudes at Thrasher and they were like, “That’s a rare find.” They were keeping the ones they had for their archives, and I was like, Alright, whatever. And then mysteriously two copies showed up in the mail. Someone liked me enough that two came in the mail, so I was thankful to them. I finally got my copy.
Dang, that’s so sick. Yeah that’d be an awesome magazine to have.
 
Where do you see yourself in skateboarding five years from now?
Honestly, the dream would just be being able to skate and going on trips, not having to worry about a manager telling me what to do. But five years from now I’d love to just be skating. I’d like to be doing more in the community with skating, especially with the queer Black and Brown kids in my neighborhood. I’d love to do clinics and stuff like that. I see that sooner than five years, though. Yeah, really just not to be underneath anybody’s thumb that isn’t in skating—that’s the ultimate goal.

J Nolliebigspin DZWhile nature reclaims the DIY, Jessyka nollie bigspins     Photo: Bravenec
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