And lots of emerging artists

Earlier this month, the 31-year-old art dealer Kathy Grayson was in her gallery, the Hole, speaking over a saw buzzing in the background. She was awaiting the arrival of 100 bags of pea gravel, 2,500 square feet of synthetic turf, four types of pond grasses, six cherry blossom trees, three willow trees, five dozen water lilies, dozens of tulips and stalks of bamboo, and a Japanese bridge to stretch over a pond. At the behest of the artists Kembra Pfahler and E.V. Day, she was transforming the Hole, for a month, into a recreation of Claude Monet’s garden at Giverny, where the painter spent the final years of his life and painted his famous Water Lilies. Once the garden was complete, she would hang in it 12 photographs Ms. Day took, on an artist residency at Giverny, of Ms. Pfahler posing in the gardens in her role as lead singer of glam-punk band the Voluptuous Horror of Karen Black: naked, save for thigh-high boots, head-to-toe body paint and a black wig teased into a two-foot-high rat’s nest.

Most gallerists would be overwhelmed with the logistics of such an undertaking, but Ms. Grayson seemed unfazed. Which is not surprising, since she’s a graduate of the school of Jeffrey Deitch, and is widely considered to be the dealer’s protégé. During her eight years at his now-defunct downtown gallery and creative incubator Deitch Projects, she was around for large-scale fantasy-land installations like “The Garden Party,” a group show following the theme of the erotic garden, familiar from paintings by Giorgione and Manet. Unlike the Old Masters’, Deitch’s was interactive: Italian artist Paola Pivi made a grassy hill that visitors could roll down. When Mr. Deitch closed his gallery two years ago, to become director of the Los Angeles Museum of Contemporary Art, downtown mourned its loss. Was the fun over? The parties? The concerts? The Art Parade? Many looked to Ms. Grayson to fill his shoes. It’s taken a couple years, but she may be hitting her stride.

Kathy Grayson grew up in Baltimore. Her father, a nuclear physicist, and her mother, who worked for the Department of Energy, met at an Atomic Energy Commission meeting. (Her older brother is now an executive in alternative energy.) They sent her to the exclusive private school Sidwell Friends, where, as a teenager, she would invite classmate Chelsea Clinton to her parties, knowing that the Secret Service would prevent the police from shutting them down.

During her senior year at Dartmouth, where she majored in art history and studio art, she came to New York for an internship at the Whitney Museum. At the 2002 Whitney Biennial she had what she later described in an essay as a revelatory encounter with the work of street artist Chris Johanson and the psychedelic art and music collective Forcefield. Their work, she wrote, “explode[d] what we expected from an art experience.” Mr. Johanson showed at Deitch Projects, so, as soon as she graduated, she applied for a job there.

“She looked like a Dartmouth field hockey champion,” Mr. Deitch told Theme magazine in 2010. “But she had the instinct, the ability to live the art. A lot of people with this academic Ivy League education, there’ll be a gap between them and the work and living artists. They can interview them and write about shows but they can’t really connect.”

Ms. Grayson could connect. A tall, imposing woman, her girlish voice and loud hairstyle—she’s cycled through a number of electric colors—can belie her serious demeanor. Within a year of starting at Deitch Projects as a receptionist she’d curated the group show “Dirt Wizards” at Brooklyn Fire Proof, in Bushwick. New York Times art critic Roberta Smith praised the show in a capsule review that also mentioned a Deitch Projects show. “I was very impressed,” Mr. Deitch told The Observer. He told Ms. Grayson she should be doing shows like that for him.

“Kathy established a vision early on,” he said.

The artists she worked with were part of her social circle, a close-knit community that thrived on collaboration. Among them was the late Dash Snow, who was known as much for his partying as he was for his art. In 2007, Ms. Grayson organized the exhibition “Nest,” which consisted in Snow and Dan Colen filling Deitch Projects with 2,000 shredded phone books, then, during all-night, drug-addled fetes, tearing Sheetrock, urinating and shooting spitballs at the walls. “It was the most radical project we ever presented,” Mr. Deitch maintains.

Ms. Grayson was living the art. “If by colorful lifestyle you mean drugs, crime and all the naughtiness, then, yeah, there are mega-drawbacks to that shit,” she told SOMA magazine in 2006. “And it takes a lot—sometimes more than I’ve got—to keep it together.”

“I was in the trenches,” she told The Observer. “Staying out every night, attending everything, meeting with artists, sleeping on floors, going to grad school studios, everything.”

Through Mr. Snow, she met the Chinese-born Canadian conceptual and performance artist Terence Koh, who remains a close friend. “He brought her to one of my house parties over at my home in Chinatown,” Mr. Koh said over email. “We bonded instantly as we were both really into Chinese wine at that time and finished a whole bottle within the first hour of meeting each other.”

She put on sponsored events that combined art and music, at one time performing, in full body paint, as part of the Voluptuous Horror of Karen Black.

“They attracted a lot of people who wouldn’t ordinarily be interested in art,” said Zev Deans, who managed Deitch’s branch in Long Island City. “People who would normally be scoffed at by the highbrow art scene. That’s why I liked her. Because she didn’t give a shit, and Jeffrey didn’t either.”

In January 2010, when Mr. Deitch shocked his staff with the news that he’d be decamping for Los Angeles, he asked Ms. Grayson if she wanted to come along. “He said I could be a young project art curator, doing an emerging art show in a small part of the museum twice a year,” Ms. Grayson recalled. Another option he gave her was to “take over the younger part of his business.”

Settling on the latter option, she reasoned that the best way to discover and promote new talent was with a commercial gallery of her own. She teamed up with Meghan Coleman, a fellow Deitch director; Tony Goldman, a real estate developer and friend of Mr. Deitch’s, gave them a deal on a space in a building he owned on Greene Street, in Soho, near Deitch. They could have it rent-free for seven months, provided they covered maintenance costs. After some hitches with funding, they opened the Hole in late June, shortly after Deitch closed for good, with the group show “Not Quite Open for Business.”

In its first few months, the Hole was a small operation, just Ms. Grayson, Ms. Coleman and a receptionist. Ms. Coleman handled logistics—accounting, installation, management of the space—and Ms. Grayson took charge of the curatorial program and artist relations. The plan was to debut 20 new artists in the first two years.

Soon, however, she was going it alone. In January 2011, Ms. Coleman realized that, as she put it, she wasn’t cut out for the commercial gallery world, and took a job with Mr. Goldman. The following month, Ms. Grayson went through with a planned move to the Hole’s present Bowery location, which, at 7,000 square feet spread over two floors, tripled the size of Greene Street.

There, she’s gotten into her groove with a Deitch-like penchant for showmanship, and spectacle. In December, at her opening for a show of paintings by Lola Montes Schnabel, painter Julian’s daughter, Ms. Grayson styled herself into a walking artwork—bright mauve hair, floor-length pleated skirt—and stood imperiously at the door greeting guests like Courtney Love, Francesco Clemente, Waris Ahluwalia and Salman Rushdie. “This is not your normal opening,” an art historian was heard to remark.

Earlier that month, at the Nada art fair in Miami, she’d taken two booths side by side, stocked them with identical configurations of artworks, and staffed them with identical twins, then hosted a blowout concert by the band Salem, poolside at South Beach’s Delano Hotel, complete with strippers doing pole dances. A man waded into the pool, asked for a lap dance, and got one.

“I support and appreciate her Peggy Guggenheim bohemian approach,” said the art adviser Rachel Greene. “I wish more people did it. If everyone is just going to get a degree in arts administration from Sotheby’s, what’s the point?”

The Hole’s Kunsthalle-like, antiprofessional vibe has raised eyebrows. “She has sponsors, she has a store, she doesn’t represent artists in the traditional sense and operates more as a project space,” said a Lower East Side gallery owner. “I’m jealous. I only have 700 square feet.”

But the Hole, Ms. Grayson insists, is not a project space. “There are a lot of galleries called ‘projects’ these days, but they’re not,” she said. “Jeffrey ran a project space. He personally invested in these huge installations that were not for sale, unless you really wanted to buy it. Jeffrey owned it.” Mr. Deitch is well-known to have supported his business by doing large deals in the secondary, or resale, art market. “He was a private art dealer who wanted to offer people this chance to make a dream project come true.”

“The Hole is an emerging art gallery,” she said. “We show the best young art here. There are lots of galleries like Marlborough that are trying to reinvent themselves with all these emerging artists. But largely, no. They have an existing stable of artists. They’re not adding super young people. That’s really my domain.”

Ms. Grayson represents a handful of artists, including Ms. Schnabel, Holton Rower, Sayre Gomez, Matthew Stone and Eric Yahnker. She shows Ben Jones and Evan Gruzis, both of whom, along with Ms. Pfahler, used to show with Deitch. Inevitably, and, Ms. Grayson said, understandably, the more prominent Deitch artists signed with major dealers: Tauba Auerbach, whom Ms. Grayson had brought to Mr. Deitch’s attention back in 2005, went with Paula Cooper. “It was obvious that taking over the Deitch business was not what I was doing,” Ms. Grayson said.

But connections to former Deitch colleagues have come in handy. For a year and a half, onetime fellow director Nicola Vassell was a director at blue-chip behemoth the Pace Gallery. During that time, Pace’s London branch began working with Aurel Schmidt, who has shown at the Hole. And Ms. Vassell brought Mr. Rower, who’d been in a group show at Pace, to Ms. Grayson’s attention. He’ll have his first show at the Hole in May.

She’s also maintained a friendship with Suzanne Geiss, another former Deitch colleague who, Ms. Grayson explained, was “the real business partner behind the scenes” and who now runs her own gallery in the former Deitch headquarters on Grand Street. Before opening the Hole, Ms. Grayson said she went to Ms. Geiss for “crucial” advice. “She advises lots of great collections,” Ms. Grayson said. “She has bought work at the Hole, for her people.”

Ms. Grayson said her own collectors tend to be young, and that around half of them followed her from Deitch. “She has a very strong voice in her writing,” said Laura O’Reilly, the Hole’s associate director. “This kind of ‘I don’t give a fuck’ attitude that a traditional academic consultant may not fully want to promote because it goes against the doctrine that they use to help sell to their clients.”

But according to an art world observer who asked to remain anonymous, moving artworks isn’t exactly Ms. Grayson’s top priority. “Kathy doesn’t sell work,” this person said. “She doesn’t give a shit about money. She lives it. If [fashion designer] Johan Lindeberg sent her an email wanting to buy a $50,000 painting, she probably wouldn’t email him back. But if he invited her to a dinner, she’d be there in a second.” In addition to selling artwork, she relies on exhibition sponsors, many of them brought in by the Hole’s creative director, socialite Fabiola Beracasa. (The Giverny show is sponsored by Playboy.com.) The Hole also has financial backers, including Jeff Vespa, cofounder of WireImage.

Then there’s Jeffrey Deitch, with whom she has remained in close contact. Ms. Grayson assisted him with the Dash Snow portion of his wildly popular “Art in the Streets” exhibition at MoCA last year. And she carried on projects that he started, like the collaborative curation of the graffiti wall at Bowery and Houston.

Mr. Deitch, whose current contract at LAMoCA ends in June 2015, is still listed as the CEO of Eighteen Wooster Corporation, which owns the Wooster Street space that formerly housed a branch of his gallery, and is now rented by nonprofit art space the Swiss Institute. Asked if she thought he would ever return to New York, Ms. Grayson smiled coyly. “If he ever decides to leave the museum, I can’t picture him doing anything else but art stuff,” she said. “Maybe if he came back to New York, he’d reopen the gallery. I don’t know.”

If he comes back to New York, he may find himself a bit redundant. “We’re not at the Deitch Projects level, where we’re paying for an army of assistants, and artists’ studios, and getting them car service,” Ms. Grayson conceded, but quickly added, “I’d love to do that, maybe in a few years.” For now, she’s focused on tulips, lily pads, pond grasses and fish. “People are going to be like, ‘Did you see Monet’s gardens? They’re in New York.’”