Selling Art to the Rich, Famous, and Inebriated

“Miami,” in the art world, is short for Miami Art Week, which is short for a week-long bacchanal of eye candy, nose candy, parties, and pills held in the name of shopping for art. The first week of December marks the kickoff to Miami, which features two or maybe three dozen different art fairs, the most prestigious of them being Art Basel Miami Beach, an import from Switzerland that, if you’re in the know, is simply called “the main fair.”

I wasn’t in the know, or at least I hadn’t been until recently. I’d spent much of my adult life convinced that art wasn’t for me. But as I hit my mid-30s, I started to worry that I was missing out on something important. I wanted to understand art—why it matters, how to engage with it, why both artists and scientists insist it’s fundamental to our humanity. So a few years ago, I spent months working in galleries and artists’ studios, spackling walls, stretching canvases, writing press releases. Then, as December neared, I started to hear more about Miami.

Depending on whom I asked, Miami was either an unmissable art pilgrimage or as tasteless as a Señor Frog’s wet-T-shirt contest. “If I had to choose between going to Art Basel Miami and dying in a plane crash, I’d pick going down in flames,” one erstwhile attendee said. It was fun. It was gross. It was “the bourgeois indulgence that comes before a Communist revolution.” I read that the year before, the galleries participating in Art Basel Miami Beach had brought $3.5 billion worth of art to sell, and that was just one fair out of dozens. Is there any other gathering where people spend so much money in so little time? Only defense expos come to mind.

Lots of art galleries try to hold money at arm’s length—pieces aren’t sold but placed, one dealer had coached me to say—but Miami, with its unapologetic buy buy buy mentality, sounded like a rare moment when the art world let it all hang out. I was curious to study buyers in action in the hopes that seeing what compelled them to pay huge sums of money for an artwork would reveal more about art’s place in our lives. But this late in the game, I couldn’t nail down a hotel room, let alone an invitation to tag along with someone who was going.

[Read: The week Miami becomes the center of the art world]

Just as I was running out of ideas for how to get myself behind-the-scenes access to the fairs, the opportunity came: Elizabeth Denny and Rob Dimin, then the co-owners of the Denny Dimin Gallery on Manhattan’s Lower East Side, invited me to come on board as their assistant—with the expectation that I’d get in there and sell. “In Miami, you’ll see,” Rob said, breathy with excitement, “it’s all about the fucking deals.”

Elizabeth and Rob had decided against applying for a spot at Art Basel Miami Beach. Instead, they would be bringing abstract photographs by Erin O’Keefe to a fair called Untitled, which was considered one of only two acceptable alternatives to Art Basel Miami. (The NADA—New Art Dealers Alliance—fair was the other.)

Art fairs are, I kept hearing, either a necessary evil or just evil. They offer exposure: 40,000 people, including museum curators and big-time collectors, had visited Untitled the year before I went. But also, fairs “do destroy galleries,” Rob told me. “If you have two bad fairs in a row, people can’t dig themselves out from them.”

In the weeks leading up to Miami, thick plumes of anxiety poured out of the Denny Dimin office each day—it didn’t help that the gallery’s recent show in New York had sold barely to not at all—and Elizabeth, keeper of bills and invoices, finally pulled up a spreadsheet to show me her budget. They were betting $39,000, cobbled together on credit cards, that they could fly to a different state, hang 21 pieces of colorful paper in a glorified elementary-school science-fair booth, and, over the course of five days, persuade strangers to fork over tens of thousands of dollars for said paper. Oh, and Elizabeth and Rob had the harebrained idea of bringing me along to help them pull it off.

Like a coach rallying players for a big game, Elizabeth gathered us shortly before leaving for Miami to announce that the gallery needed to sell about $70,000 worth of art, or 13 or so photographs, to break even. Really, we needed to sell a lot more, both to avoid Elizabeth going into cardiac arrest and to afford their ambitious expansion plans. Elizabeth and Rob hoped spending money would ensure that the gallery would grow in lockstep with their artists, who were “emerging” now, but asking for more as their careers swelled. Bigger-name fairs. More help paying to produce expensive pieces. “If they’re doing their job well, they’re demanding,” Elizabeth said. It was grow or be outgrown, and they worried that artists would ditch them for larger galleries. The finish line was the museum door. “I can’t wait for the day an artist of mine has a show at the Whitney,” Rob said.

Yet even with so much at stake, in Miami, sobriety was apparently optional. Perhaps even a liability. “A very prolific art dealer who’s a friend of mine said to me five years ago that the only way to have a successful Miami is to either be drunk, high, or hungover during fair days, and so two years ago, I tested his philosophy,” Rob announced one day. “It was our best Miami.”

Rob’s other advice: “RSVP to everything. Literally, like, literally—RSVP to everything.”

I RSVPed to everything. At least I tried to. Rob forwarded me more than a dozen invitations and a friend shared a list of parties that ran seven single-spaced pages yet opened with the disclaimer that it included only evening events—“daytime art touring plans elsewhere.” From the Monday before the fairs opened until the following Monday, from cocktail hour through breakfast, I could, if on the guest list and immune to sleep, bowl with Swizz Beatz, pay $70 to celebrate a billionaire real-estate developer’s birthday, watch a photographer’s live photo shoot of a Brazilian supermodel, and get down to beats beats beats while a DJ and artist held space for a “collective catharsis” from commercial activities (this was sponsored by Facebook). Every party was a “bash”; music was “tunes”; food was “culinary cuisine.” The invitations leaned in close to yell, “COME TO THIS GLITZY BASH FEATURING ’NSYNC’S LANCE BASS.”

I quickly realized that RSVPing was a competitive sport, and I was losing. This was confirmed when a gallerist flashed me his schedule—a mess of bashes I hadn’t known existed. I begged an art-dealer friend to help me get a VIP pass to the main fair, which allowed me to RSVP for even more events and enjoy a satisfaction akin to leveling up in a video game. This must be the feeling Art Basel Miami’s ex-director had in mind when he congratulated the fair for having “fine-tuned the idea of contemporary art as a lifestyle choice.”

Two days before Untitled officially opened, I flew to Miami. On the taxi ride to my hotel, I passed sprawling art fairs, billboards advertising fairs I’d never heard of, and three art museums. There were two art fairs on the beach across from my hotel and a plane over the ocean dragging a banner by the artist Mister E: MONEY ISN’T REAL.

[Watch: The problem with art fairs]

Collectors had begun assembling in Miami as well. They intrigued me: Artists and gallerists discussed them with a mix of fear, reverence, and occasional disdain that made them sound so powerful, so otherworldly, that I’d gotten fixated on the idea of studying these buyers up close—preferably surrounded by their spoils. I’d spent the previous six months trying to weasel into art collectors’ homes. But how? I couldn’t very well just show up at a billionaire’s door, ring the doorbell, and ask to see the joint.

In fact, I discovered in Miami, that’s exactly what you do. South Florida’s biggest art collectors have a pre-art-fair ritual of flinging open their doors to let strangers gawk at what they’ve bought. As was my right as the proud holder of an Art Basel VIP pass, I joined the poreless and exquisitely orthodontiaed in touring these sprawling homes. Uniformed valets relieved visitors of their Maseratis, rented baristas fed us espresso shots, and pretty young women handed out maps in case we’d failed to recognize that the painting over the couch was a priceless Anselm Kiefer, which, feeling smug, I had recognized.

I’d understood that rich people could buy lots of art, but I hadn’t realized until this moment that my definitions of rich and lots were off by many orders of magnitude. “Clients ask me, ‘Are we collectors?’ And I say, ‘Has the word warehouse entered your vocabulary?’” said an art adviser, an old hand on the Miami circuit.

One collector, Beth Rudin DeWoody, had taken over a former munitions depot to show all the art she couldn’t fit in her art-filled apartment in New York, her three art-filled apartments in Los Angeles, or her three art-filled homes in Palm Beach. Wandering through her invitation-only bunker, The Bunker, I abandoned all hope of savoring each work—I’d be here for days, possibly weeks—and videoed the rooms like everyone else was, vowing to review the footage later.

I managed to claim a few minutes with DeWoody, flanked by her two curators. Her support for emerging artists had made her something of a patron saint to gallerists, and she was legendary for buying art omnivorously—so much so that she sometimes had trouble keeping track of what she had. She told me she’d gone to a show by the artist Theresa Chromati and raved to the gallerist about how much she loved Chromati’s work. “He said, ‘Oh, you know you own one of these,’” DeWoody recalled. Her response: “I do?”

Tuesday morning, the first day of Untitled, I woke up late and hungover, thanks to Rob’s advice, and was a sweaty mess by the time I hustled to the art fair. At 1 p.m., Untitled would officially open its doors—to the VIPs, that is. Collectors, curators, museum patrons, and journalists were Very Important. Untitled’s organizers and exhibitors gave them free passes. The “schmos”—one gallerist’s term for “general public”—could come starting tomorrow, at $35 a head.

At 1:15, I was talking to my first VIP. I’d spent days reading everything I could find on Erin O’Keefe, then memorizing two pages of talking points. “So the artist paints wooden blocks,” I told the VIP. That didn’t sound right. I tried: “She cuts out painted pieces of cardboard.” I was making her sound like a preschooler.

At 1:19, Rob made the day’s first sale. “This gentleman would like to acquire edition one,” he announced.

Nearby, a man in a dark blazer was explaining how to set up and structure trusts. A middle-aged woman with a soft blowout reviewed her daughter’s headshots, occasionally zooming to scrutinize invisible flaws. The men, in pastel linen button-downs over pressed khakis, were delicious little sorbets plopped on ice-cream cones, while the women—gold pants, metallic jackets—glittered like disco balls. From across the tent, I heard the hollow thop of popped champagne.

Another piece sold. By 3 p.m., I’d upgraded from “O’Keefe photographs her sculptural arrangements and then destroys them” to “She dismantles them.” “They look very painterly, but they’re photographs of physical materials,” I tried, to no avail. I referenced Piet Mondrian, then threw in “Mondrianesque,” just because. I was beginning to annoy myself. “That work has been placed,” I told a woman. “Does placed mean ‘sold’?” she asked. I wanted to fire myself.

At 7:11 p.m., I counted nine pieces sold that day, none by me. Determined to prove myself, I asked Elizabeth for sales advice. I’d heard gallerists try to sell work using what they called “context”: by mentioning that this artist was beloved by The New York Times’ art critic or was in the Dallas Museum of Art’s collection or was currently dating a more famous artist.

But Elizabeth didn’t like spiels about the artist’s résumé. Focus on the art, she advised. And don’t say placed. “It sounds too pompous.” Elizabeth reiterated her golden rule: “I don’t leave the work until someone asks me a question that leaves the work. Until then, I stay in the work.” It was a kind of Hippocratic oath: Stay. In. The. Work.

The artist Gina Malek had made a similar suggestion when I visited her studio in the Bronx. “Just walk up to a piece and try to think of five things that it brings up,” she suggested. Not five things that the art is about. The observations don’t need to be grandiose, like This probes masculinity in the postinternet age. Just: What are five things you notice, either in the work or in how it makes you feel? “Like, that red is very cool or very warm … That shape really dominates the canvas … I love how that paint is gushy and then it thins out,” Gina said. “All those things are important, and they’re intentional.”

The next afternoon, during a brief moment of calm, I let Erin O’Keefe’s work wash over me. While trying to appear available to passersby, I stared at a small photo, 20 by 16 inches, just to the left of my shoulder. Stay in the work, I ordered myself. Five things.

O’Keefe had photographed three objects positioned on a watermelon-pink surface that butted up against a brushy, hollandaise-yellow expanse. On the left-hand side of the image rested a half-moon of canary-yellow cardboard; behind it was a long, skinny brown pole thing; to the right of that was an hourglass-shape chunk of wood painted red with a curvy swoop of green. Or at least I think the things were cardboard and wood. O’Keefe’s photos could pass for paintings and consistently made me second-guess what I was seeing.

Now that was interesting. From some cobwebby corner of my brain, there surfaced the memory of an old college professor lecturing that photographs were duplicitous by nature. In theory, photos faithfully capture a snapshot of reality. And yet photographers, like journalists, inevitably frame each scene in a way that cuts out some details and calls attention to others. O’Keefe’s photos seemed to be toying with photography’s untrustworthiness. I kept staring, transfixed. There, hovering on the yellow backdrop, was a shape I’d never noticed before: a mysterious pale circle, some kind of tiny glowing orb. I had no idea how it got there. Was it painted on the backdrop? A reflection of light? For the first time, I felt the thrill of being lost.

Doubts immediately rushed in. Look at the pretty colors! The preciousness of the paper! O’Keefe’s photos were beautiful, I realized with a sinking feeling.

After spending time in the art world, I’d grown suspicious of beauty. It had become clear to me that elite society considered beauty to be toxic, and saw seeking it out as a sign of moral weakness. Philosophers, art critics, scientists, and garden-variety intellectuals have, over the past 100 years, teamed up with artists to declare beauty both corrupted and corrupting. It’s “superficial and consoling,” “tainted by bourgeois values,” and “manipulated by those in power,” writes the professor Rhett Diessner in his book on beauty. “Today,” he says, “it is simply treated by the art world as a joke, a con, an idiotic, old-fashioned idea.” I worried that enjoying a beautiful artwork meant I wasn’t really moved.

Being around O’Keefe’s photos just felt good, like lying on a beach towel in the sun. Only that wasn’t necessarily something erudite art connoisseurs were supposed to say. The reviews of O’Keefe’s work that I’d memorized and repeated had praised her references to cubism and “carefully structured architectonics.” None of them alluded to the way O’Keefe’s photos could make you feel warm, tingly, and relaxed.

My sales pitch changed. I stayed in the work, and people stayed there with me.

By Thursday, the VIPs had been joined by a more diverse crowd. In spite of the overstimulating chaos of the fair, lots of them circled the booth over and over, jaws slack as if they’d been hypnotized, then came back later tugging friends behind them. “These are photos?” I got asked a lot. “Wait—that’s not a painting?” Nope. “What about that one?” Still a photo.

Partway through the day, a middle-aged couple, dressed like matching sailboats in crisp white button-downs and navy loafers, wandered into Denny Dimin’s booth. I hovered beside them as they paused in front of each photo.

The woman stopped at one of O’Keefe’s biggest pieces—a photograph of squiggly cardboard shapes that made me think of cubist houseplants. She didn’t move. She didn’t even blink.

“The gallery—so this is a New York gallery?” she asked at last.

Lower East Side, I confirmed.

“Her studio’s in New York?” Yes. “Do you do a lot of fairs?” Yes. “How long have you been representing her?” Four years. Silence. I sensed she needed a nudge. Context, I understood, was also a way to try to securitize your investment, a way to be sure you weren’t the only one who thought this work was special. I murmured a sweet nothing about O’Keefe’s “institutional support.”

The woman turned to the man she was with. “Is it going to Boston?”

“Or Palm Beach?” he said.

And that’s how I sold my first piece: $9,800, thank you very much. I felt giddy, as if I’d just been called onstage to accept a prize, but I played it cool, tight smile and firm handshake, while I swiped their credit card.

That first sale chummed the water. I got a little bloodthirsty after that. I sold two more pieces and put one on reserve for a woman I’ll call Isabel. I gobbled down dinner and was on my way to the Pérez Art Museum Miami cocktail party when a sexagenarian named Poodle—smoky eyes, crocodile purse—tried to steal my Uber, but Poodle was going to the party too, so I invited her to tag along.

Rob found me at the museum and took me to another party, where I pitched O’Keefe to a guy next to us in line for tequila sodas whose reply was “A lot of my art is in storage,” which translates to “collector” and immediately got him our full and undivided attention. “The Tate reached out to ask if they could have this for their upcoming retrospective,” he said, showing me his phone, and Rob couldn’t pull out his business card fast enough. Drinks by the pool with gallerists from Germany (“Have you seen O’Keefe’s work?” I asked, rummaging for my phone) turned into the backseat of someone’s Escalade destined for Soho Beach House. My phone buzzed with a text from Isabel saying she wanted to buy the photo she’d put on reserve, just as someone beside me in the Escalade noisily hrooonfed a line of cocaine. Dive bar from 12:30 to 1:30 a.m. Gay-bar dancing with half the population of Brooklyn from 1:30 to 4:13 a.m.

“Coffeecoffeecoffeecoffee,” Rob was chanting when he got to the fair a few hours later. “We ended up going down to the beach at 5:30 in the morning.”

I made another sale. Scarsdale or Florida? “You have too many houses!” chirped the clients’ art adviser.

I sold a piece to a couple in their 40s who came back three times before taking the plunge, and another to a young couple who decided to splurge on a small O’Keefe print. Scratch that—make it two, they decided.

We ran out of the red-dot stickers we used to mark pieces as sold, and I bounced between booths asking if anyone had some to spare, which was obnoxious, but I did it anyway, dizzy and manic off the high of selling.

It’s easy to sneer at the spectacle that is Miami Art Week. And I could see how doing Miami every year for a decade would make you want to lock yourself in a closet and scream into a pillow. But I’m not sure where else you’d find thousands of people shouting about art over dinners, over dance floors, overnight, and at all hours of the day. As the week had worn on, instead of feeling exhausted, I was exhilarated.

Sunday, the last day of the fair. A steady stream of artists filed through the booth, chatting and pressing business cards into our hands while stressing their deep interest in the gallery. Sean Fader, an artist represented by Denny Dimin, dropped by. He was curious to know how I was feeling now that the fair was nearly over.

A little shell-shocked, I confessed.

“You never thought you’d be wheeling and dealing art in Miami,” Sean said.

“Definitely not.”

Sean got very serious, which was unusual for him, and he leaned in so close that our foreheads were practically touching. “Every red dot means an angel gets its wings. And some fucking artist can pay their rent, okay?” he said. “It means that somebody who’s a maker gets to keep making.”

In the final hours of the fair, I learned that the gallery across from us, which hadn’t sold anything, would be shutting down at the end of the year. Denny Dimin was not closing. We’d had a blowout fair. I’d sold seven pieces. The gallery had sold more than two dozen, for a total of—Elizabeth was still adding up all the invoices—more than $200,000. They’d live another day to share artists’ work. And that, in the absence of a more perfect system, was something.

This article was adapted from Bianca Bosker’s forthcoming book, Get the Picture: A Mind-Bending Journey Among the Inspired Artists and Obsessive Art Fiends Who Taught Me How to See.