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What Does It Take for a Female Tycoon to Get Noticed Around Here?

It’s not as if Tilton isn’t aware that her style can overshadow her substance. “I think the fact that I look like this hinders me in some ways,” Tilton says between outfit changes. “But that’s also what makes me so much more fascinating, right?”

She begins wriggling out of the dress. “I’m all about transparency,” she explains, as the dress falls to the floor. She’s not wearing any underwear. “Where do you get someone who’s worth looking at and listening to?”

Stark naked except for her Gucci heels, seamless Brazilian Bronze tan, and diamond necklace, she flicks through the rack of clothes. “I mean, hello. I’m just trying to be someone who provides it all.”

Growing up in Teaneck, New Jersey, Lynn Tilton never thought she’d become a Wall Street financier. She wanted to be a writer. She still enjoys fiction—“anything with shadow hunters, angels, ­demons,” she says. “I don’t believe anything is made up. It’s just not yet been discovered.” The Traveler, a futuristic novel in which a young woman from a warrior class is trained by her father to fight against a shadow government, is practically required reading at Patriarch.

Tilton’s own father, who was a New York City public-school teacher for many years, was tough: He would fire trivia questions at his children and then call them morons when they got the answers wrong. “My father was just so brilliant and so talented,” Tilton says. “He sort of thought his kids were cookie-cutter. He struggled with our frailty and flaws. He was always testing me to be perfect. To push. But I knew he loved me. I think he knew that sort of … I was destined to do something special.”

“I mean, hello,” she says, stark naked save for Gucci heels. “I’m just trying to be someone who provides it all.”

She developed a formidable work ethic. In high school, she’d start her homework at 4 A.M. and practice tennis after school until it was dark. At Yale, she majored in American studies with a concentration in literature. But after her father developed a brain tumor and died during her junior year, Tilton’s life plan changed: She married her high-school boyfriend and, after graduating, took a job at Morgan Stanley. After having Carly in 1982, she left the industry, but when she and her husband separated a few years later, Tilton saw returning to Wall Street as her only option. She got her Columbia M.B.A. in fourteen months and soon found herself working at Goldman Sachs.

Wall Street was not the most hospitable environment for women, especially back then. In 1991, after having taken a job at Merrill Lynch, Tilton sued the company for sexual harassment. A settlement prevents her from talking about the details, but Tilton says she doesn’t remember much anyway. “My early years were pretty dark,” she says, fluttering her hand as if to dismiss the memory. “I was so young and scared. The details are sort of shadowy.”

At her next job, as an analyst at Kidder Peabody, there was also “a real locker-room mentality,” says Arlene McCarthy, one of Tilton’s only female co-workers. But by then, Tilton had adapted. “Lynn knew how to put the guys in their place. If someone made a joke she didn’t like, she would give them a look. They wouldn’t do it again.”

She was also, paradoxically, known to be flirty. “She liked to be provocative,” says Tom Bernard, her colleague of the time, who was immortalized in Liar’s Poker as “the Human Piranha.” “Sometimes you’d walk by and hear her on the phone and be like, ‘Hmmm.’ ”

Whatever she was saying, it worked. By 1990, Tilton had transitioned to selling distressed bonds. She bought a home in Boca Raton, where she became acquainted with a group of “Mexican gardeners” who introduced her to Carlos Castaneda’s The Teachings of Don Juan. Tilton devoured the book, in which a Yaqui shaman teaches the author the Toltec art of sorcery, and the gardeners became her spiritual teachers.

“They changed my existence,” she says. “I come from a line of Kabbalist scholars”—she claims her father was a descendant of the Baal Shem Tov—“but my father died before he ever passed a lot of this stuff on to me. I wonder always whether he didn’t grasp it—or if he didn’t get around to telling me what I needed to know. Or maybe I wasn’t ready?”

She no longer keeps in touch with her teachers. (“They’re nowhere to be found,” she says. “They sort of left the universe.”) But the lessons they imparted to her—how to master control of dreams, become one with the universe, empty herself of wants, and see lightness and darkness clearly—led Tilton to believe she was meant for more than a life in finance.

By 1998, she had $10 million in the bank, enough to support herself and Carly for life, and she decided it was time to retire. She left her job at the time, as a partner at Amroc, though not before sending clients a Christmas card that has since become legendary: Double-sided, it featured two photographs, one of Tilton in a red lace bodysuit and Santa hat, straddling a stepladder, and the other of her wielding a whip in black lingerie and high vinyl boots. Her clients “were always asking what color underwear I was wearing,” she says. “So that was my farewell gift.”