The Stylish Job Saver: Lynn Tilton Owns More Companies Than Any U.S. Woman

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Tilton Owns Homes in Italy, Florida, Arizona and New Jersey

"My twenties were so difficult and so dark that I only remember shadowy details," she said. "Because I lived in fear every day. … Fear of not being able to keep my job and take care of my child. Fear of being a failure."

Tilton spent 19 years on Wall Street, often clashing with its macho culture. She sued Merrill Lynch for sexual harassment, settling out of court.

"I was so beaten down by that experience that I wasn't sure I'd be able to stand up again and get back out into the world," she said.

Tilton had saved $10 million from her Wall Street earnings. Upon leaving, she sent a final Christmas card to some of her clients.

"For many years I had men asking me on the phone each day what I was wearing and what color my underwear was," she said. "And so I sent out a Christmas card with me in a red lace sort of teddy, and red cowboy boots and a Santa hat, wishing them a Merry Christmas."

Tilton's plan was to spend the rest of her life far from Wall Street. But then she had a dream in which her father told her retiring wasn't what he had in mind for her, she said.

What was her calling? "Really, to come back and try to help people," she said. "To 'save' people from what I suffered when we lost a working parent … the crumbling of a family. That for every job I could save, that was a family that would be kept together. … And so I have tried to -- at least in later life -- make my father proud."

In Dec. 2000, Tilton launched Patriarch Partners, a New York-based private-equity firm named in honor of her father. In the past 11 years, it has turned around dozens of failing companies, among them Spiegel Catalogues, Rand McNally and Stila Cosmetics.

The firm has investments in 14 different industries including helicopters and trucks, she said, adding, "The only thing they have in common is that nobody else wanted them."

Tilton takes a personal interest in the daily operations of many of her companies.

She said she spends a million dollars per year criss-crossing the country. Recently a typical week could have included stops in New York, Arkansas, Los Angeles, Georgia and Phoenix, where MD Helicopters -- which Tilton brought out of bankruptcy and into a long-term contract for military helicopters -- is based.

Tilton's intense focus on work leaves little time for relaxation at her four homes: one on Lake Como, in Italy; one on a beach in Florida; one in Phoenix; and one in New Jersey. She has not remarried and lives alone.

"I'm not extravagant for someone of my wealth," Tilton said. "I love beautiful jewelry. … I have a great wardrobe."

Tilton has four closets full of shoes -- 500 pairs, all categorized with photos.

Tilton has no apologies for her reputation as a ruthless boss.

"To lead so many [employees], one has to be difficult and tough at times," she said.

She even admits she is particularly tough on men.

"I think I'm tough on everybody," she said. "Perhaps more difficult on men. … I speak the truth. And that means that sometimes people don't want to hear exactly where they stand. … The truth is cold and hard, but it's the first point on the path to hope and salvation."

When her management teams enter the room for a meeting with her, she said, she hugs them on the way in and out. In between, she gives them "truth and harsh speak."

What drives Tilton more than anything these days, she said, is jobs. "We must create jobs in this country, or we will have violence in the streets of America," she said.

Tilton said she was not surprised when, over the last few weeks, Occupy Wall Street gained acceptance all over the country for its demonstrations against the rich.

"But there's only one way to put people back to work in this country, and that's industrial policy. Pick your industries. If you want to sell it in America, you need to make it in America," she said.

When asked what advice she would give a young person who wanted to be a billionaire, Tilton said, "Don't do what you do for the money. Whatever path you choose, do it because it makes your heart beat fast. Because success comes from following your passion."

CLICK HERE TO WATCH THE FULL "20/20" EPISODE ON TILTON AND OTHER SELF-MADE BILLIONAIRES

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