That Simchowitz would gobble up multiple galleries’ worth of an artist’s paintings, of course, is why Brown refers to him as a control freak. Simchowitz may introduce artists to gallery owners, and plenty of gallery owners court Simchowitz with interesting pieces they can’t sell. But when an artist does take off, Simchowitz can wind up with an inordinate share of the market, enabling him to set his own terms. Rather than gamble with him, places like Blum & Poe shut him out. Or at least they try. The kerfuffle there began when Simchowitz phoned the gallery to inquire about the artist Darren Bader; he was told that Bader’s work was not available. “I wanted to buy two pieces for my guys and a riot shield for myself,” Simchowitz explains, referring to an actual polycarbonate police shield Bader created. “He doesn’t make many objects, so this was a big deal.” The gallery demurred, so he sent an art consultant—someone the gallery knew but did not realize was affiliated with Simchowitz—to the Culver City-adjacent space to buy the pieces.
Had Simchowitz kept quiet about his acquisition, nobody would have known of the deception. But he couldn’t help himself. Soon after, during a visit to the gallery, he met a partner of Poe’s and pleaded his case for doing business together while boasting about the Bader purchase. It didn’t take much for Poe to figure out that Simchowitz had sent a proxy to snag the pieces. On his next visit he was escorted out. “Blum & Poe is scared of me,” Simchowitz says. “What am I supposed to do? Respect their decision? I want the art. So I get it.”
I relate all of this to a sometime friend of Simchowitz’s named Carlos Rivera, who coded an algorithm for evaluating the monetary value of artworks. “There are a lot of people who just don’t like Stefan,” Rivera responds. Gavin Brown dismisses Simchowitz as an “interesting, vulnerable, pathetic character.” Poe, according to Simchowitz, called him “a piece of shit—four times!” The artist and photographer Richard Prince joked on Instagram about filming a Simchowitz biopic titled Patron Putz. And a New York dealer I spoke with likened him to Freddy Krueger.
Night Gallery’s Marple is not among the haters. “I think Stefan is really smart and brave, but I wouldn’t want to be him,” she says. “It would be hard to have all those people saying things about me.” Simchowitz, however, seems as if he’d have it no other way. New York magazine art critic Jerry Saltz referred to him as an “opportunistic speculator” in a widely read blog post last year. “Jerry did me a huge favor,” Simchowitz says. “He created amazing velocity; one day I will send him a giant bottle of Cristal.”
From the start Simchowitz knew that he did not want to go the traditional route. Merely making a living wasn’t an objective or a necessity. “My father’s got a lot of fucking money,” he says, speaking of the South African corporate raider Manny Simchowitz, who currently resides in Bel-Air and dabbles in commercial real estate. “I could easily be a shithead driving around in a Bentley, smoking cigars, and hanging out at Harry Cipriani.” But for somebody with Simchowitz’s level of ambition, that would be misery. Armed with a degree in economics from Stanford—he graduated in three years—he plunged himself into show business. Between 1996 and 2006, Simchowitz helped produce a clump of largely undistinguished films, Darren Aronofsky’s critically acclaimed Requiem for a Dream being the exception.
In 2001, the year after Requiem came out, Simchowitz partnered in a photo-syndicating enterprise called WireImage, which enabled magazine editors to buy celebrity shots via the Internet. The concept was novel at the time: Users uploaded images from contract photographers digitally rather than dealing with physical pictures. Initial growth was slow, but after anthrax-laced letters were sent to various news outlets that year, magazine editors became skittish about opening envelopes. Business boomed. In 2007, the company was sold to Getty for $200 million; after investors were paid and taxes collected, Simchowitz says he walked away with some $4 million.
Influenced by his artist mother, a former stepmother who once sat on MOCA’s board, and his father, who has amassed a major collection of modernist work, Simchowitz decided to redirect his energies to the business of art. He viewed it as ripe for disruption—and an easier business than the movie industry in which to make a score. “There were too many galleries and too much dominance,” Simchowitz tells me as he drives his new Porsche SUV to Paper or Plastik, a bare-to-the-rafters coffeehouse near Pico and Fairfax. “I decided that financing artists at a studio level would be the business. My preference would be to exchange financing for work. I asked artists what their fantasies are. I financed them and usually they ended up making great shit. But then I had to negotiate complex deals with their galleries, and the galleries did not like it.”
He solicited a project from British artist Jonathan Monk, who came up with one that involved deflated-looking sculptures crafted in the style of Jeff Koons’s balloon-like bunnies. Simchowitz bankrolled it. Casey Kaplan gallery in Manhattan, along with Lisson Gallery in London, showed it, and Simchowitz characterizes the whole enterprise as highly profitable for everybody involved. “But,” he adds, “it was like schadenfreude. They were more concerned with how much I made than with the fact that they made money and the artist did as well.”
A source connected with the show counters that it wasn’t so worthwhile for the gallery or artist. “I’m sure Simchowitz sees himself as a good guy, and why shouldn’t he profit from his venture capitalist way of being,” he says. “But it is a multifaceted way of being. Talking about Simchowitz is like talking about the stock market, which is not the way I look at things.”
Stefan Simchowitz refers to his house as an “art kibbutz.” It’s not a terrible exaggeration. The three-bedroom midcentury home is filled with paintings and sculptures. Collectors and creators flit in and out, debating design and politics. “We like to run things here village style,” says Rosi Riedl, a strikingly tall former model with short, textured gray hair. Austria born and Australia raised, she went from being Simchowitz’s wife to his ex-wife to the mother of their six-year-old son, Morris, to her current status as live-in companion and business partner. “Mansions are cold and polite veneers for people who are dirty behind the scenes.”
During the week I spent in Los Angeles staying at the house, a British video artist by the name of Jimmy Merris (another of Simchowitz’s art investments) bunks in the bedroom of Morris, who usually sleeps with his parents anyway. After a friend of Simchowitz’s from New York shows up, Merris moves across the street to a Spanish-style home that Simchowitz rents for the stashing of art and guests. His four-person crew works in the primary home’s garage turned office, gathering now and then in the backyard, where a swimming pool occupies one corner. Lunch is a friends-and-family affair, with everyone eating at a long wood table that runs parallel to the kitchen. In the midst of it all, Simchowitz wears a gray wireless-telephone headset from which to pass judgment (“Out the back door with that piece,” he advises. “It’s inferior work. Get rid of it.”), negotiate art deals, figure out shipping, and smirkingly half apologize for misdeeds (like making fun of a potential client for driving a Forester).