It was only then that Simchowitz shifted into contemporary art.

Having an art collection, he

reasoned, was a bit like owning land: Art not only appreciated in value, it also afforded cultural
cachet, something he learned by watching his father, who had built a renowned collection of
modernist paintings. Instead of using his limited funds to acquire third-tier works from established
stars — Simchowitz had no interest in buying a “minor Warhol” or a “second-rate Kusama,” as he
put it — he decided to focus on emerging artists. He started out buying and selling works in the
$10,000 range, acquiring about three dozen pieces by artists like Sterling Ruby, Joe Bradley,
Tauba Auerbach and Cory Arcangel, all of which have appreciated considerably over the last six
years (today a Sterling Ruby can fetch a million dollars or more in the secondary market). He
estimates that since 2007 his collection has grown to some 1,500 pieces worth as much as $30
million, with about 5 percent of the works accounting for 50 percent of the value.

Simchowitz describes his house as a kibbutz, as it often swarms with visitors — young artists, old
dealers, models, ex-models, his ex-model ex-wife, members of his ex-wife’s extended family, his ex-
stepmother, clients, employees, members of the press, a variety of dogs, his 6-year-old child, his 6-
year-old child’s 6-year-old friends. Less typical of a kibbutz, Simchowitz’s house also serves as the
global headquarters of Simcor, the umbrella organization for Simchowitz’s art-world empire. In
late July, when I met Simchowitz at his house for lunch, I found the space inviting but glutted with
inventory. Comic details abounded, including an artwork in the bathroom that said “buy stuff”
(Simchowitz’s unofficial mantra) and a doormat that read “the neighbors have better stuff” —
almost certainly a lie. In any event, I learned that the house was rarely empty, making it an unlikely
target for burglars, and there was even talk of renting the house next door for extra space, which
would make Simchowitz his own neighbor.

On arrival, I was greeted by Simchowitz’s partner in both life and business, Rosi Riedl, a tall, silver-
haired former model — one prominent curator dismissed her as “a Bond girl” — with a strong will
and a buoyant disposition. Riedl was born in Austria but moved at age 12 to Australia, where her
family lived on a sheep farm. (“Her family has no money,” Simchowitz later confided. “They had to
eat their own sheep.”) When she was 21, she moved to Los Angeles, where she met Simchowitz on a
beach. They married within two years and divorced within seven, but following the divorce they
continued to live together and eventually had a child. “It was all Stefan-style, so nothing happened
very politely,” Riedl said as she escorted me into a garage that had been converted into an art-
market command center manned by additional beautiful women.

Over a lunch of salad and steamed vegetables — Simchowitz was trying to lose 15 pounds and had
instructed his staff to snatch away pastries and schedule sessions at SoulCycle to help him tone his
physique — I asked Simchowitz why he was so unpopular among his art-world peers. “I’m the
poster child of evil speculation,” Simchowitz acknowledged, munching his veggies, “but it’s totally
incorrect.” Every dollar he made, he claimed, went directly back to feeding emerging artists. “I am
100 percent invested in art. I have no working capital. I make $100,000, I pay my taxes and
overhead, $50,000 goes back to supporting some young artist’s career. It’s a very efficient system.”
Galleries and museums, he pointed out, effectively forced artists to subsidize sky-high rents and
unwieldy bureaucracies. It was true that he traded pieces with speculators, but as a necessary evil
to fund his artists in advance of their eventual payday.

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Art speculators caused trouble, argued Simchowitz, not when they flipped their works but when
they cashed out. “The problem is when the parasites come and extract dollars to buy a Ferrari or go
to St. Bart’s for the weekend. You have a lot of people coming in — literally stockbrokers, bankers,
speculators — who have no interest in art, who are just trying to gain. I am not one of these people.
You can spend five minutes here and see I invest in cultural production.” Indeed, the fruits of
Simchowitz’s cultural investments lined the walls. Over the sofa in the living room hung three large
Parker Itos from the series “The Agony and the Ecstasy”; Sterling Ruby adorned his bedroom and
kitchen.

He went on to claim, though, that many of the worst offenders were not the speculator-barbarians
at the gate but high-profile collectors — he wouldn’t name them on the record — revered within the
community. “The vampires of the business are in the system! The problem is that these people are
at St. Bart’s. They’ve got names. The galleries like names.” Museums liked names, too, and would
often blindly award board seats to regal-sounding donors with deep pockets. “They don’t
understand it’s actually a divorced drug addict or a rich socialite who basically wants to be on a
board as a trophy.” Simchowitz suggested that galleries and museums preferred “social investors”
to “capital investors” because wealthy divorcés were easier to control than market sharks. “My ex-
stepmother was on the board of MoCA. I know what these women are like. My father has collected
my whole life. I know what they’re like. The galleries want a very specific song. They want
Beethoven’s Fifth.” Simchowitz, on the other hand, was serving Iggy Azalea, bringing “realness” —
or his idea of realness — to an art culture plagued by hypocrisy and prevarication.

Three days later, Simchowitz took me to meet some artists. The first stop was Morgan Richard
Murphey, a transient 24-year-old abstract painter with a bushy brown beard and a show coming up
in Brussels. Murphey was both homeless and studioless, so Simchowitz had arranged a live-work
residency for him at the studio of Danny First, an Angeleno collector (major) and sculptor (minor).
When we arrived, the studio — a warehouselike space on an alley off La Brea — was littered with
beer cans and whiskey bottles. Murphey greeted us wearing a black leather jacket.

“He decides to show up, huh?” he said, smiling at his patron.

“I had to see what’s cooking,” Simchowitz replied.

Among art-world rituals, the studio visit is one of the holiest. Whereas film directors do their
scouting like cattle drivers, corralling actors through humiliating casting calls, gallerists and
curators cultivate relationships with artists by trekking to far-flung neighborhoods (Bushwick,
Highland Park) and indulging long, wandering discussions about theory and practice, inflected by
deadly, half-read undergrad syllabuses. Dealers make these journeys because they bolster the
important art-world conceit that gallerists and artists meet as equals. For artists, studio visits
provide the opportunity to explain how individual pieces fit within their broader practice, thereby
giving contextual heft to work that might otherwise appear flimsy or mysterious. Simchowitz,
however, mostly shuns this convention. If he’s interested in an artist’s work, he asks the artist to
forward images via email or text message. His decision to drop by and check on Morgan Richard
Murphey was partly for my benefit but also motivated by practicality: Murphey, who didn’t own a
cellphone, seemed ill prepared for his impending show. It was face to face or not at all.

On the walls of the studio were a series of canvases smeared with black paint that feebly gestured
at Abstract Expressionism. Bewilderingly, one was inscribed with a global-warming slogan.
“There’s going to be three subcategories in the series, and then they all start cross-contaminating
each other,” Murphey haltingly explained. As Simchowitz perused the works in progress, he began
to look worried. “Just try to work out some of the ideas,” he said, looking straight at Murphey.
“Keep the show focused. I need you to work. You’re very distracted.”

Murphey smiled nervously. “Focus?” he asked, chuckling.

“You either want this or you don’t want this,” Simchowitz said sternly. He was clearly referring not
just to Murphey’s show but to his career as a whole. “If you don’t want it, do something else. Focus.
There’s no alternative.”

“Uh, absolutely,” Murphey responded, mumbling.

As we got back into the car, Simchowitz expressed disappointment. “It’s very weak. I probably
spent $20,000 on that guy. That’s gone — whoosh. I won’t get behind it if I don’t think it’s good.”
The work wasn’t ugly, but like Murphey himself, it seemed arbitrary and out of time. In addition,
the artist seemed bent on endowing the work with an inner logic that would be impossible to
convey on social media, clearly a red flag for Simchowitz. Murphey’s career was still germinating,
though, and Simchowitz wasn’t prepared to write him off yet. “He could be good; it’s early. This
happens a lot.”