Cortright’s studio was a former punk-music club at the easternmost point of Los Angeles, on the edge of Alhambra, far from Simchowitz’s collector base in the Hollywood Hills. The artist and her fiancé had recently installed an archery range in the basement; we arrived to find her holding an arrow and wearing a white baggy blouse, white high-waisted jeans and white Comme des Garçons shoes. She looked like a movie star but exuded the aura of a cult member from the ’70s.

Cortright’s fiancé, Marc Horowitz, a lapsed painter whom Simchowitz had recently encouraged to wield the brush again (“just wait two years,” Simchowitz told me, “he’s going to be massive”), explained that they installed the archery range as a way of coping with creative mistakes. “It’s where all the bad work goes to die,” he said. I looked up and saw that instead of the customary bull’s-eye targets, the couple had mounted old paintings.

Cortright led us on a tour of the studio, passing through the two-story atrium, the showroom, the library, the kitchen and an expansive roof outfitted with chaise longues for tanning and a mist-sprayer to prevent overheating. Cortright’s actual work space was on the second floor and featured a pineapple plant and a collection of chakra-balancing sunglasses in multiple colors. “I always wear the pink ones,” she said. “They’re supposed to make you happy and playful.”

On the walls hung digital paintings, printed on silk and depicting tropical landscapes. Recently, though, Cortright has enjoyed particular success with a more abstract series on aluminum. Simchowitz likened her digital paintings to Monets, because of her elaborate layering process, and explained that he had been encouraging Cortright to employ what he called “proprietary production techniques” to make her work more popular with collectors. He had taken steps to prevent the fabricators she used from offering these techniques to other artists (“I don’t think it’s ethical,” he explained) and he had bought up as much as he could of the available 60-by-80-inch die bond sheets Cortright used for her aluminum work.

Art pricing is a pure confidence game — there are no fundamentals to anchor the price of a painting, because a painting doesn’t produce a stream of revenue. Emerging artists can be likened to start-ups, in that most eventually go to zero but one could become the next Jeff Koons. When an artist’s prices overheat, though, it can instigate a panic and cause his or her market to implode. Young artists momentarily heralded as the next big thing can just as quickly be tossed in the trash. As Riedl explained it, the trouble with speculators is that they “flip, flip, flip,” and the piece “becomes like a musical chair. When it tops out and they can’t get any more, they throw it away, and then it’s done, and the artist is over. You don’t go back to a reasonable price — you’re cooked, you’re finished.”

In November, a pair of Cortright’s digital paintings on aluminum sold at auctions put on by Phillips and Sotheby’s for $40,000 and $43,750, up from less than $13,000 at an auction in July. Simchowitz says he has no doubt that her paintings will eventually breach the $1 million mark (an achievement that would put her in the company of perhaps 2,000 other artists in the history of the world). An alternate trajectory for Cortright would be that of her studiomate and longtime friend Parker Ito, another Simchowitz investment, who had a painting sold at auction for more than $80,000 in July but who in his subsequent 13 auction results averaged just $30,000 per piece (in three other auctions during that period, his work failed to sell at all). Like many of Simchowitz’s more successful wards, Ito has now distanced himself from Simchowitz; Cortright told me that whenever he came to visit the studio, she informed Ito in advance so he could avoid an accidental encounter. Despite repeated hectoring voice-mail messages and emails from Simchowitz, Ito — who painted tanks for an oil company before Simchowitz met him — has barely spoken or written to Simchowitz in months.

Back in his BMW, Simchowitz took calls as we crawled toward the west side in rush-hour traffic. Some of Simchowitz’s most esteemed clients, like Anna Getty (heiress to the Getty oil fortune) and Nicolas Berggruen (the “homeless billionaire” financier famous for living in hotels) are friends who come from clans with a long history of collecting. Others, like Orlando Bloom, Harvey Weinstein and Steve Tisch, are Hollywood connections. Then there are the tech entrepreneurs, including Sean Parker (Napster/Facebook) and Bradley Jabour (medical imaging), as well as an array of lower-profile market sharks. Simchowitz’s method for managing relationships with these clients (some of whom are more active than others) isn’t very different from his method for dealing with adversaries: He screams at them, tells them they’re idiots, brags about his triumphs and assures them he has the inside track.