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In our long-running series, "How I'm Making It," we talk to people making a living in the fashion industry about how they broke in and found success.

When Whitney, Alyssa and I arrived at West 4 Tattoo (accidentally very) early to interview and photograph Jonathan Valena, the New York City-based tattooer professionally known as JonBoy, he (understandably) isn't there. We're told he's running an errand and to head up to his station, where he'll join us in just a few minutes. But before we even settle in, JonBoy appears ahead of schedule — unmistakeable in an orchid-print windbreaker and hot pink sweatshirt (both Gucci) — carrying a tray of four iced coffees for his team. 

We introduce ourselves and so does he, with a smile, a joke and a big Midwestern wave. (He grew up on the North Side of Chicago before moving to the suburbs and later spent six years as a tattoo artist in Minneapolis. He quips: "No one knows about Minneapolis. So, I'm like, 'Yo, you know Prince is from there?'") As he gets prepared, we take his area in. The space is covered in all sorts of fashion kitsch; shelves are lined with Christian Louboutins, Supreme MetroCards and a variety of luxury shoeboxes, while a swatch of Gucci paper covers the wall. Polaroids taken with celebrities he's inked — I first spot Chloë Grace Mortez and Sofia Richie — are staggered throughout. It's as if Fashionista's collage wall has come to life.

Our interview begins, and I realize quickly that he is like many of my favorite interview subjects in the fashion industry. Of all the figures I most admire in this business, many — if not all — have conveyed that you're never too established, never too famous, to be kind. JonBoy is living proof of this, often extolling deep gratitude for the turn his career has taken. "Treat people kindly, like gold," he says, "because those are the people that are paying your bills and keeping your business going."

After his early dreams of tattoo artistry were brushed aside, he went to seminary and studied to become a youth pastor; only then, while working in Iowa, did he leave that role to pursue another. But in a sweet turn of events, it's that involvement with ministry that prompted his tattoo business to really take off: JonBoy met Hailey Baldwin, his first true celebrity client, at church. "I feel like I owe it to [Baldwin]," he says. "It's opened the door to tattoo a lot of other celebrities and other people."

Now, his fashion-adjacent Rolodex has expanded to include the likes of Kendall Jenner ("meow" on the inside of her lip), Bella Hadid (a tiny angel wing on her ankle) and Zayn Malik (a glow-in-the-dark lightsaber on his middle finger). JonBoy spoke with Fashionista about just how he did it, and what he's learned along the way. 

Photo Whitney Bauck for Fashionista

Photo Whitney Bauck for Fashionista

Before you were JonBoy, you were a kid in Chicago obsessed with your grandfather's Navy tattoos. From what age do you remember gravitating towards them?

I was maybe six or seven. Growing up and being close to my grandfather — and just staring at his tattoos — gave me this feeling like, "Man, I want to be like him. I want to get a tattoo." I didn't know how it worked, but I knew it was cool. Although my grandma hated it, [one of his tattoos] was something he got for her. He got a rose on his arm and her name was Rose.

I knew that I wanted to get tattooed one day; I knew it was rebellious because the rest of the family hated it. I grew up a kind of rebellious teen anyway, so the tattoo culture was attractive — and being a skater kid, too, and seeing that type of imagery on skateboards turned me onto that art.

Did you have explicit dreams of becoming a tattoo artist then?

I got my first tattoo when I was 19, and I went crazy. I would get a tattoo every two, three weeks. I would try to hustle the money in. I didn't have the type of money to be getting tattooed, so I was going into my sister's Beanie Baby collection and flipping comic books and baseball cards and action figures to make money.

The more I got tattooed, the more interested I was in how it worked, how you can permanently mark your body with a piece of art. The more I got tattooed, the more I inquired about it with all the artists. I would ask them, "How do I get into this? How do I learn how to do this?" It seemed like, for the most part, all of the artists were discouraging me. They'd say, "No, you don't want to get into this. It's not an easy business." Or people would say, "Well, if you've got five grand, I can apprentice you."

That was in the early 2000s and, obviously, I didn't have that kind of money. I gave up the dream of even getting into the industry. I went to seminary, and I went to school to be a youth pastor. In my two years of seminary and in my time as a youth director, I started hanging out in a local tattoo parlor in Iowa, just helping out. That's where my teacher, Kevin Fitzgerald, an old biker guy, was like, "Hey, if this is something that you want to learn how to do, I can take you under my wing and teach you how to pierce and tattoo."

Do you think, if it hadn't been for him, you would have found another avenue to make that dream happen?

I'm not sure. It's so cliché, but I feel like tattooing found me. It's something that chooses you. So, maybe. 

You lived in Minneapolis for six years prior to coming to New York. At what point did you decide you wanted to move here?

It's always been a dream of mine to live in New York. Growing up and watching movies and TV shows and seeing New York — whether it be "Ninja Turtles" or "Ghostbusters" or whatever — you're just like, "One day I'm going to live in the big city."

Did I ever think I'd be tattooing everyone here? No. My first year living in New York, I started working at a shop called Find My Tattoo. They're the reason I was able to move here. I came to visit with a girlfriend at the time, and they were like, "If you're still interested in moving to New York, we have a couple days for you to work. We don't really have many hours for you, but at least you can get your foot in the door."

It wasn't easy, but I was excited. Between barely getting any hours, not making any money and being the small fish in the big pond, it was completely opposite of when I was living in Minneapolis. Everyone knew who I was. Coming here, I had to start over again. I didn't have that clientele that I did in the Midwest.

You've said before that your early style was first inspired by Dr. Woo, tattooer to the stars in Los Angeles. How did you go about forging your own style?

Before I began seeing Dr. Woo's work, I never thought that tattoos could look the way they do. I was turning away a lot of people because people didn't want the big sleeve and the big back piece. People just wanted little tattoos with superfine lines and lettering and all that stuff. I was like, "Man, I can't do it." So when I saw Dr. Woo, I was like, "This guy is doing it! What kind of needles is he using? What kind of machine?" I had to go back to the basics. I used to build my own needles and build my own machines.

I did a formal apprenticeship where I had to learn how to make my inks and build a machine; I had to solder needles myself for the needle bar. Nowadays, you can just buy them premade — they come in a blister pack, and boom, that's it — versus having to spend 15 minutes on each needle. I'm super-grateful that I know how to do those things. I definitely earned my stripes.

Photo Whitney Bauck for Fashionista

Photo Whitney Bauck for Fashionista

Minimalist tattoos have really hit a fever pitch in the last few years. Why do you think that is?

We — including the tattooers — didn't think that tattoos could look this way. We weren't tattooing people in the professional world — in fashion especially — because those people couldn't get tattooed. If they had tattoos, they couldn't be photographed. It would keep them from getting jobs. That we're able to do these tattoos opens doors to people that are aesthetically driven; they can be in front of a camera, have a tattoo and still look sophisticated and classy. I love that approach, that I can put a tattoo on you and it could look like a little charm, a little accessory. It could be small and hidden, if it needs to be.

Do you feel fashion and body art are interconnected?

Yeah. You're just seeing [tattoos] more and more. It's not just the people behind the scenes. It's amazing seeing Hailey [Baldwin] photograph and seeing my tattoos all over her. You never would have have seen that 10 years ago. It's exciting being part of that.

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Fashion and tattoos have a beautiful relationship. As long as you keep it classy; it's all in the details. And with my tattooing, placement is key. There's nothing like a good tattoo that just looks out of place. It needs to flow with the body. I feel that especially when I'm dealing with people who are in front of the camera.

What has an "Instagirl" like [Baldwin], or women like Bella Hadid, Kendall Jenner and Sofia Richie done for your business?

I feel like I owe it to Hailey. I tell Hailey every time that if it weren't for her coming in and getting tattooed by me, I wouldn't have the clientele I do because she's the one who brings Kendall and Kylie and Justin [Bieber]. Those guys are all best friends. A circle. It's opened the door to tattoo a lot of other celebrities and other people.

That trust that you have to build with your artist... I think that's important. If I were to tattoo Hailey and I was an asshole — I didn't give her any respect or I fangirled — I feel like the trust wouldn't be there, and that would have been the word around the street.

Can you fill us in on your love for Gucci? How and why did that obsession start?

My mom and dad rocked Gucci in the '80s and '90s. It was a status thing for my parents when they moved out to America [from the Philippines]. I was a fan of Gucci because of that. Gucci got a little stale for a while, I feel, after Tom Ford. When Alessandro [Michele] became creative director, we were in Vegas and [Lauren Ledford, JonBoy's manager] said, "I want you to see the new Gucci." When I went into the Gucci store, I was like, "Holy crap, this imagery!" It just feels like tattoos. The tigers and the florals and the snakes... it's very tattoo-esque. I don't ever fangirl, but when [Alessandro Michele]'s around, I'm like, [gasp].

You recently collaborated with Koio Collective on your own special-edition sneaker. How did that partnership come about?

I'm a fan of their sneaker. They had gifted me a pair of white shoes with gold eyelets — they had this Balenciaga-Common Projects vibe — and I thought they were sick. They approached me and explained their brand and that they wanted to start doing collaborations with certain artists. The quality's great; they manufacture in the same factory as Saint Laurent and Chanel, so their craftsmanship was exceptional.

So now, I'm coming out with my own sneaker, which is awesome. We just got the prototypes in and I'm like [gasps] I can't believe it! I want to make sure that with any collabs I do that you look at it and you're like, "That's totally JonBoy," rather than saying, "Oh, man. He probably just got paid a lot of money to do this." I want it to be organic.

Photo Whitney Bauck for Fashionista

Photo Whitney Bauck for Fashionista

At this point in your career, how many tattoos do you do a day?

I usually try to take about five clients a day. I try to keep it chill, so I can spend the time with my clients. When I announce a walk-in day, I have a line of people out the door, and I probably try to tackle anywhere from 15 to 20 people.

It sucks that I'm that guy who has his books closed. For me, it's an honor [to be a tattoo artist]. If you're like, "Hey, JonBoy. I want to get tattooed by you." I'm like, "Really? For real? I would be honored to put my work on you." I have those walk-in days for the people that can't get in. It's always a beautiful thing when you see people show up for you, specifically. It's amazing.

Your recent Broome Street pop-up got a ton of play. How did it feel to see such large groups of people lining up for you like that?

The support feels great. It's them that makes me look good; I just do the tattoos. I give them my 100 percent. It's because of my Instagram that they're getting the cool ideas and letting me tattoo them, and I'm able to post and show it off. Really, at the end of the day, it's the people that are making it happen for me. Not me. I'm here to show up and give them the best experience. If I didn't have people to tattoo, then no one would know who I was.

What kind of role has Instagram played in growing your business?

I remember when I first signed up for Instagram, I was like, "Nah. I don't know about this." I remember some of my friends at Everlane sat me down and said, "You've got to change up your Instagram. It's all over the place. If you're on private [make it public]; find something consistent in how you post."

Where do you see yourself and your business in the next five years?

I would love to have my own shop so that I can build it from the ground up and have creative direction with how I want it to look. I want to create a set of standards for tattoo shops. I feel like most, not all, tattoo shops have a bad reputation. A lot can be snobby and pretentious if you're walking in for your first tattoo, and the person you're getting it from might only be used to doing back pieces. But, just treat people kindly, like gold, because those are the people paying your bills and keeping your business going.

I want to set a standard where when customers come in, we're there for them. We say customer service — a lot of people forget the word "serve" in customer service. We're here to serve. We're working for you. This is your hard-earned money and this is your body that you're entrusting me with, so I want to make sure that all the artists understand that, and there's no egos. You never know who you're going to tattoo. People have a lot to offer. I feel like it's important to shake every hand because you never know. I'm interested in people. You get a lot to learn from people if you give them a chance.

I used to not trust people. I used to be that kid that was hurt by my past like, "I trust no one." [Points to chest] I got it tatted right here. Just kidding. [Laughs] When you give people the chance, you have an opportunity to learn, to be blessed and to be a blessing.

That's very Midwest of you.

It is. We might have to have cheese. 

Photo Whitney Bauck for Fashionista

Photo Whitney Bauck for Fashionista

Note: This story has been updated throughout.

This interview has been edited and condensed for clarity.

Homepage photo: Whitney Bauck for Fashionista

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