Ian Sullivan could’ve showed up an hour or two before he was scheduled to perform. Most in-demand artists would have allowed themselves enough time to set up, and that’s about it.

Ian Sullivan is different. When he’s invested, man, he’s invested.

It was a balmy, humid night, days before the first official event Eesho would ever host, a rooftop fundraiser to benefit Emily’s Entourage. Ian Sullivan wasn’t drawing or painting for a change – this was a strategy session and Ian wanted in. He had a different part of his brain fired up for the occasion, the same part he relied upon when thrown into the fire several years earlier, asked for his input in the redesign of Will Smith’s office as part of a previous employment. If he was good enough for Will Smith, he’s good enough for Eesho, we joked.

On this night, Ian’s canvas was a roughly 40×30 foot rooftop in the East Village, broken into three main sections and a pair of corridors by bright white fences, the iconic Empire State Building shimmering in the distance, wondering what his next move might be.

“What about this bench over here,” he says to me, not exactly waiting to hear my answer. By the time I had a moment to consider his proposal, I didn’t need to anymore. The bench was very clearly where it was meant to be all along.

Ironically, the vast majority of Ian’s fung shui-inspired suggestions were designed to open up space, maximizing mobility and optimizing interactions between the 60+ guests who would be there in less than 72 hours, by far the most people the roof would ever hold.

If you’ve seen one of Ian’s signature styles of art, Fear of Negative Space, you might not expect him to be so acutely aware of open space. After all, there is almost no negative space whatsoever in many of his paintings. Then again, maybe that’s exactly why he’s so damn good at making space appear out of nowhere. He spends much of his existence manipulating and curating space, playing within the rigid confines of a very particular perimeter. If negative space is Ian’s enemy, perhaps it’s no wonder he knows it so well.

Know thy enemy.

A signature style is born

The battle of Ian Sullivan vs. Negative Space began out of necessity. Well, sort of. It was English class, and there was all too much unoccupied space in Ian’s head. The class was boring him into a state of forced creativity for the sake of mental survival. He would pass the time by repeatedly drawing different styles and renditions of his graffiti tag on a piece of paper, allowing the shapes to intertwine from different angles.

All of a sudden, he realized something unexpected was happening. The shapes and lines were fitting together almost as if they were meant to be together. Well how about that, he thought to himself. As he continued to test his discovery, sure enough, one sign neatly tucked into the next, which fit perfectly within the next, and so it would continue.

“Initially it was only my tag over and over again,” Ian recalled to me in a rare quiet moment. “But I felt like such an asshole just writing my own name a million times to make a design. That was ridiculous. I was like ‘wow that wasn’t fun,’ I actually feel worse.

“But then I started to use the accents that you have in graffiti — sometimes you can make a crown or a stylized star, an arrow or an X, and then I use squiggles to fill in the negative space.”

And just like that, a signature style was born.

“It’s the most therapeutic thing I’ve ever learned,” Ian continued as he gazed into the distance, almost as if he were in meditative state. “Seriously, it is, [it’s] super relaxing. I do it a lot ’cause I like it and people seem to like it as well, which is obviously a plus, and thank god they like it — because I love it.”

An unexpected twist

Don’t for a second make the mistake of confusing a signature style for a one trick pony. In this case, it’s quite the opposite.

About a week before the fung shui session, Ian had visited our East Village rooftop to brainstorm for the event. He was also getting to know me and Emily Priebe, the two co-founders of Eesho, after having met just a few weeks earlier at another fundraiser for Emily’s Entourage, hosted by Generation Next and my sister-in-law’s brother Nick Levy. Ian and I had hit it off after I spontaneously bought a 6×4 foot mural off him in the lobby of Nick’s cousin Max’s apartment building. (I’m 5’10” in extra thick socks, so yes, it was a ridiculous purchase at the time. Also one of the best decisions of my life.) An hour or two after Ian burst onto the rooftop with the energy you’d expect from someone fleeing a group of cattle in the Running of the Bulls, he shared his scrapbook for us to peruse.

With close friends Adson Alfonso and Brittany Moya flanking me and Emily, we collectively had one of those moments when the limits of what you thought you knew no longer apply.

In retrospect, it was probably our own fault for assuming Ian’s scrapbook would closely resemble the majority of his publicized work. Ian isn’t the first artist to hone in on a particular crowd-pleasing style. Still, we were blown away by the seemingly endless diversity on display page after page after page. It was almost as if a different artist had been commissioned to fill each page. Ian was like a one man artist collective, marked by common threads of detailed illustrations, graffiti-inspired abstract portraits portraying a fictional persona Syn, and intricate cityscapes that juxtapose the grittiness of the NYC streets with the vibrant personalities that occupy them.

“I think versatility is important,” Ian would tell me after I asked him weeks later about his scrapbook. “Plus I have ADHD, so I don’t even think that was up to me.

“Seriously, man, it’s cool. Within a working environment, it’s good to be versatile, especially if you’re not that adept at computers, which I should be. Initially I wanted to learn a lot of styles and just do a lot of things because I like drawing. I originally was just drawing ’cause I wanted to draw, I wanted to be a little different than everyone in my neighborhood and drawing was a pretty good outlet. It kinda just morphed into something else.”

Ask Ian what type of artist he is first and foremost and you might be surprised by his answer. He won’t say muralist or graffiti artist.

“I went to Pratt for illustration and I like being an abnormal illustrator, I like describing myself as an illustrator,” he revealed, wearing a mesh Pratt Basketball tank top that accentuated his long, muscular frame. “I like storytelling. I like stories in general, so when I do some of these drawings that have a lot of characters, when I do these sort of two dimensional cityscapes, I create a dilapidated setting but with a really fun activity or action going on to juxtapose [the setting].”

The man behind the art

Over a game of ping pong, on a mid-size blue Joola table, Ian shares some of his other hobbies and passions.

(It was our second ping pong table of the same variety; the first had been ruined by rain a week earlier, only to be heroically revived by Ian’s generous sleight of hand, forever rid of the negative space that had previously absorbed hundreds, if not thousands, of ping pong balls an hour.)

He was an avid basketball player and played for Pratt, recalling a game in which his team almost lost to The Culinary Institute of America. “That would have been so embarrassing, man,” he said with a not-so-subtle smirk. He owned a clothing line for two years. And now, he manages the Anderson Contemporary gallery in Manhattan’s South Street Seaport District, a beautiful and expansive space owned and directed by Ronni Anderson.

But most of all, Ian draws (and paints), as his Instagram handle @iansullivan_draws and the mural he was recently commissioned to paint at One World Trade Center would suggest. And on a glorious 78 degree night seven floors above street level, donating his time and talents to Emily’s Entourage as guests started to flood in, a master of his craft went to work.

Surrounded by five other pieces he cranked out leading up to the event – spanning three distinct styles – and operating from the corner of the live art + ballpit + art gallery room we had designed together just days prior, Ian was in his element.

There’s no telling exactly what the future holds for Ian Sullivan. But spend a few minutes with him talking art or life and you’ll inevitably reach the same conclusion I did.

Man, this kid’s invested.