At an opening at The Hole this evening, Lola Montes Schnabel (daughter of artist and filmmaker Julian Schnabel) will present what’s described as her first solo painting exhibition in the United States, “Love Before Intimacy.” Earlier this month, Danny Gold, a contributor to The Local, followed The Hole’s charismatic founder, Kathy Grayson, as she showed off Ms. Schnabel’s paintings at the N.A.D.A Art Fair in Miami Beach.

Lauryn Brooke Kathy Grayson.

While the big-money crowd flocked to Art Basel in Miami Beach earlier this month, a crew of downtown New York upstarts gravitated toward a younger alternative. At the N.A.D.A. Art Fair, the names on the gallery walls weren’t as well known, but the faces were familiar to anyone who had spent a good amount of time at Max Fish. (The art bar on Ludlow Street is just a handful of blocks from The New Art Dealers Alliance’s offices on Chrystie Street.)

Kathy Grayson, 31, owner of the Hole, was one such familiar face. Her gallery at 312 Bowery leads the pack of D.I.Y. art spaces that have recently opened up downtown. Raised in Washington, D.C., the Dartmouth graduate got her start as a receptionist at Deitch Projects, a duo of SoHo spaces that were among the most influential galleries of the last decade.

After Jeffrey Deitch left Manhattan to run the M.O.C.A. in Los Angeles, Ms. Grayson set off on her own. Her new gallery has hosted an impressive array of up-and-coming artists as well as its share of debaucherous opening parties.

N.A.D.A. was no different: Ms. Grayson produced four big events during the long weekend, and sold art out of two identical booths staffed by Dee and Ricky Jackson, the wunderkind designers for Marc Jacobs who happen to be twins. The name of the stands? “Déjà-Booth.“

Kathy Grayson Salem performs at the Gusman Theater.

During the fair’s opening night, Ms. Grayson played hostess at the Delano Hotel. As well-to-do Europeans wearing scarves and linen shirts unbuttoned to the navel dined at the gorgeous hotel’s restaurant, New York City’s art kids took advantage of free scotch and sake just 150 feet away. A duo of strippers gyrated topless in the pool as ambient-rap group Salem (a favorite of Ms. Grayson’s) played to the accompaniment of a smoke machine and Klieg lights.

“The Delano was great,” she said the next day. “Everyone ended up making out with each other.”

Ms. Grayson spent the evening surrounded by her brain trust. Her entourage included model and former Hole intern May Anderson, who helped build the gallery with director of operations Jorge Ulrich, a fellow East Villager best known for curating the public art wall on Houston Street and Bowery. Also on the scene: Hearst heiress Fabiola Beracasa, the Hole’s creative director.

The after party was back at a house Ms. Grayson had rented for the week. She got just two hours of sleep before she was back to the grind.

“It’s fun if you don’t get tired,” she said. “When it starts to suck, yeah, it can be tiring: having the same conversation 400 times – who said what, what their second wife’s name is. It’s good, though – much better than nobody talking to you at all.”

That night, the Hole hosted a screening for the street artist Neckface at the Gusman Theater. A thousand people crowded into the elegant baroque venue to watch a four-minute film in which a kung fu fight ended in a woman’s gruesome decapitation. After another set from Salem, the British artist Matthew Stone closed with a DJ set heavy on Rihanna.

Lindsay MaHarry Smashed cake at the Playboy party.

The rest of the week, Ms. Grayson’s maintained a hectic schedule: There was a dinner at the Mondrian with the C.E.O. of the Morgans Hotel Group to celebrate Mr. Stone’s sculptures by the pool, and a Playboy party at the Dream Hotel for artist Kembra Pfahler. There, nude women painted like aliens sang over subdued beats. One of them smashed a cake with her buttocks and the others feasted. The crowd – a mix of Miami club-goers, downtown kids, and visiting Europeans – cheered with equal parts approval and confusion.

After the set, when told a painting by one of her former artists had sold for $150,000, Ms. Grayson replied, “Oh God, anything else – let’s talk about today, tomorrow but not money. Please.” With that she laughed, then gulped down half of her drink.

“I should be tired,” she said. “But I’m not. We’ve had such a great week.”

Ms. Grayson started out as an artist, but found that her friends in the industry lacked the skills necessary to sell their own work. She found a calling promoting them, writing about them, and eventually curating their work at Deitch Projects.

During the eight years she served as director, she brought artists like Dan Colen, Terence Koh, and the late Dash Snow into the public eye. It was she who curated the notorious “Nest” installation, for which Mr. Snow and Mr. Colen cut up hundreds of phone books to simulate a hamster’s cage and then did drugs until they felt like hamsters themselves.

Kathy Grayson “Déjà-Booth.“

Deitch’s reputation and deep pockets gave her freedom. She said, “With Deitch, I could say, ‘I want to do a one-night exhibition for Terence Koh. I need $100,000,’ and it could happen.”

At her own gallery, she remains focused on pushing boundaries and supporting the community of artists, musicians and designers around her. In Miami, her twin booths showed two paintings by Lola Montes Schnabel, daughter of artist Julian.

“She’s never had a solo show,” said Ms. Grayson. “One sold for $25,000; the other was put on hold by a to-remain-nameless celebrity.”

The Hole also sold works in the sub-$50,000 range by a half-dozen artists, including several by Mr. Stone, who had a well-received show at the Bowery gallery earlier this month, and others by Kadar Brock, a graduate of Cooper Union.

“We could have sold 15 of Brock’s works,” said Ms. Grayson. Not bad for a gallery that opened last March with a show curated by streetwear icons Alife, featuring what might have been the first ever work of art by a bar (Max Fish offered a $7,000 table).

“It’s really hard to constantly be finding out what’s going on,” Ms. Grayson said. “You really have to live the life.”

Tonight at the Hole, she’ll host an opening party for a new show with Lola Schnabel and some abstract painters. A text invite to the opening read: “Both of thse shows are killer. I can’t wait for everyone to see!!”