I couldn’t find the PDF invitation to CONTEXT Art Fair during Art Basel. T.K. and I stood at the pavilion’s VIP entrance while the guest services director scrolled through my email incredulously. “It’s there, I swear,” I urged her, smiling sidelong at the security guard who’d inspected my purse moments before.

When we finally gained access to the fair’s booths, I took special measures to hold my collarbone broad, chin parallel to the floor. It was my first time at Art Basel, my first time in Miami even, and we were attending a special pre-viewing event for a show where millions of dollars would be exchanged. This was the big time, what I had waited my whole life for. I’d bought my plane ticket only a week prior.

T.K. and I split up, as we often do, favoring a strategy to divide and conquer. When I reached Kai’s booth, I found him sitting on a fold-out chair, his knee in a brace. After admiring his work’s messages and refined craftsmanship, I approached him. Kai smiled sweetly. I asked him if he made the clocks featured in a few pieces. He did. He made everything.

Triumph relies upon genuine confidence, rather than fabricated bravado.

Kai’s biography states that he “is recognized for his ability to convey a powerful message through any medium. His unique style and social commentary continues to set him apart from other street artists.” In a hall full of egos and expensive haircuts, Kai felt like a real person with an artistic purpose.

Talking to Kai allowed me to regain the personhood I’d been too overwhelmed to remember in the lion’s den. Although he had a huge booth with his name on it at the nation’s most revered gathering of artists, Kai laughed and joked like we’d just bumped into each other on the subway. I returned the next day to speak with Kai, hoping to learn more about his path and how one maintains themselves in the face of success. I learned that triumph relies upon genuine confidence, rather than fabricated bravado.

In a hall full of egos and expensive haircuts, Kai felt like a real person with an artistic purpose.

Taking to the Streets

Kai’s dad was a heavy smoker, and his grandparents weren’t a part of his life. This left him with a fear that his children might someday experience the same elder-less fate. Desperate to curtail his father’s deadly habit, Kai created his now infamous ‘Morons’ work on a small canvas. Morons replaces the Marlboro logo on the company’s packaging with Kai’s derisive opinion of smokers. “I just put it in his room, in front of his TV, and I went to bed. He woke me up around midnight, and said ‘I love it. I’m done. I’m gonna quit smoking. I want to support your art career, I want to support what you’re doing, so here’s $400.” His father asked, “‘please don’t spend it on shoes, please spend it on something to continue spreading the message.’ So I started to hand make posters one by one, and I would put them in the street.” At the mere age of fourteen, Kai received his first budget for art work.

Kai quickly gained notoriety. “Being young, and a little bit dumb, or innocent, I went crazy with my street art. Anywhere and everywhere I could, I would put up a poster.” His work drew a variety of impassioned reactions. “My first email was this lady who [wrote] me saying, ‘I’ve been trying to quit smoking for ten months, I saw your poster and made it the background on my phone and I’m officially going to quit.’ And then I got other mail like ‘let me enjoy my cigarette in peace, I have a very stressful life.’”

“Being young, and a little bit dumb, or innocent, I went crazy with my street art. Anywhere and everywhere I could, I would put up a poster.”

I asked him how he handled getting hate mail as a teenager. He replied, “I’m a very competitive person. I took it as motivation, like, ‘Oh you don’t like it? I’ll make sure now you see me everywhere you go. You took the time out of your day to bother me? I’m going to make sure I bother you ten times more.”

Building a Future in Art

As Kai’s name recognition grew, his visions for the future were tinted a decidedly un-rosy hue. “I knew that being an artist was a tough thing,” he recalled, “it [would be] hard and difficult, but I just thought that I loved doing it, I would do it until I [couldn’t] afford to do it.” Fortunately, his success sustained him. “I would sell stickers and posters to kids in school or on the internet, and I had enough money to keep going.”

The artist’s big break came at sixteen, when a Los Angeles gallery asked to showcase his work. He was thrilled, but apprehensive about being taken for a ride, given his young age. “So I emailed back saying, ‘I’ll send my assistant, you can work out the details with him.’ I went myself as ‘Kai’s assistant.’ I worked out a deal with the gallery and sent my pieces over.” Since he met with them as his own assistant, rather than the artist himself, Kai felt confident entering into negotiations. An exclusivity clause proved the only snag. Kai said, “I felt like I didn’t want to be exclusive to anyone. But the fact that he was giving me an opportunity to show my work for the first time really made me believe that it was worth it. We came to an agreement where I was going to be exclusive for the first three months, which gave him enough time to tell everyone ‘come get the work here’ and gave me the comfort of saying ‘in three months if I’m not happy, I can move on.’”

The gallery loved his work so much that they gave Kai his own room. However, he recalled, “they had the opening, and every artist sold except for me. For the next two weeks, I didn’t sell any artwork.” His dry spell lasted beyond the opening reception, until the gallery finally told him that if he didn’t sell soon, they would have to remove his work. “That weekend,” he remembered, “I got a call, and he said, ‘not only did I sell your art, I sold two of your pieces to the owner of Hudson Jeans.’ He gave me the amount I made and I was in shock, completely flabbergasted. I didn’t understand how I could have made so much money after making no money.”

Studying in Paris

Even with this victory under his belt, Kai faced troubles ahead. He left for Paris, where he studied at Beux-Arts. “The starving artist, I know what that’s like,” he said. “When I went to study in Paris, my monthly budget was $1,000. I would have coffee for breakfast, lunch, and dinner because I got tired of drinking tap water, and coffee was so cheap.”

He also encountered difficulty conveying his work’s messages in the face of the language barrier. To solve the problem, he created IF (Imaginary Friend,) the character seen in his recent works. IF’s conflicts are depicted throughout Kai’s repertoire, and he serves as the vehicle for actions that everyone can sympathize with. Kai said, “the idea is that [IF has] no class, no sex, no religion. I want everyone to feel connected and relatable to the character.”

Finding Food

Today, Kai can count himself among the elite ranks of successful artists. He works with Markowicz Fine Art for his studio pieces, and still completes murals like his recent commission for G-Eazy in Los Angeles. I asked Kai if he felt like he’d overcome the starving artist phase of his career, to which he humbly replied, “yes, but I still have that mentality. If you ask anyone that works with me, the work and the stuff that we produce in the studio always comes before anything else. I love the idea of putting your soul and your life into the work because I think you can feel it. I think I’m one of the only artists that installs their own shows.”

His street work is just as coveted as his studio pieces. Sometimes, after the tiring hours spent creating an illegal cement installation, he’ll return only to find it stolen. Kai said, “I have people who will send me stolen work from the street and ask me to authenticate it so they can sell it. It makes me feel good, like I made it, but it also makes me feel like I put so much effort into getting that in the street. I’ve been arrested five times trying to do stuff like that. I always tell people, ‘you could have bought a small piece for way less effort than taking it and re-gluing it and putting it back together.’”

“I never thought my prices would get this crazy…”

Kai’s commitment to providing affordable works for fans differentiates him from other artists of his caliber. He told me, “I never thought my prices would get this crazy. It’s so hard to make these works, it’s so much time and effort, and the demand is kind of crazy. At the same time, I never wanted to get this expensive, so I always made sure that the prints stayed at a reasonable price. I don’t want a print to go for $1,000, I want a print that everyone is able to afford. Growing up, I wanted to buy from a lot of artists and I couldn’t.”

He continued, “I only work with Bernard at Markowicz Fine Art, and it’s a very open dialogue with the pricing. We kind of price things as cheap as we can to make sure I can still live a regular life and not end up in a one bedroom with six people. Yes, he would love to price them even more expensive, but at the same time, he always gets pushback from me saying ‘no, this is already insane, how can we even go any higher?’ And he understands it, he says, ‘okay, I respect that, I respect your decision.’”

Some artists use price as a method of conveying value. Kai doesn’t see this as a worthwhile strategy. He explained, “I think if you’re doing that, there’s a motive behind it because you haven’t created enough demand and there isn’t enough hype or belief in you, so you’re trying to artificially create it. I don’t know any artist that has done that and been able to sustain it for more than a season or two. Collectors are not dumb. I think you have to price correctly to the market that you’re at. I started selling paintings at $700. You have to be true to the market.”

Forging Forward

At twenty-six, Kai is still a young artist with obstacles to overcome. When asked about his impressions of the fine art world, he told me, “I felt under appreciated. This is my tenth year making art. Because I started so young, I had that advantage that I was practiced, I was trying. Having struggled that much, and having fought to learn and study all these techniques and mediums, I felt like I deserved to be here and I wasn’t getting the respect I deserved.”

I asked him if he felt nostalgic for his early, purely street art days. “It depends what day you ask me. Today I feel like I’m starting to ride the line between street art and contemporary art. People are starting to respect the work and starting to understand the work. We’re no longer just [making] street art. I think we’re starting to break into the contemporary world, and starting to say ‘hey, street art is contemporary art.’”

“I think success comes from when people say, ‘I recognize that, I know that.’”

He continued, “I still do murals, I still do a lot of illegal street art. It’s part of who I am, that’s what made me me… I never want to lose that side of myself. If you ever see my old street work, the cement plaques in Europe and elsewhere, it was then that I started to develop such a fine-tuned level, so precise and so beautiful because I was trying to elevate street art from the street to the gallery. That was my mission, I used to make mini galleries in the street.”

Without financial motivations, Kai measures his success in terms of accomplishments. He elaborated, “to me, I think success comes from when people say, ‘I recognize that, I know that.’ I think that’s where my success is. The realest way I see my success is when I get a message, DM or story that says ‘that changed my life’ or ‘I made a decision because when I saw that, it helped me see my life clearer.’ I always get really excited like a really giggly kid. Money doesn’t matter as long as I’m with the people that I love and we’re having fun and we’re not starving to death. The thing that makes something valuable isn’t the material or what it is, it’s the effort and the love that you put into it.”

To learn more about the artist, check out his website: KaiArt.com

To read more by the author, check out her website: VittoriaBenzine.com

Instagram Round Up

Kai Art

Vittoria Benzine

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T.K. Mills