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Then & Now: Heidi Fleiss

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Then: Heidi Fleiss achieves 1990s infamy after her arrest.

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(CNN) -- Heidi Fleiss grabbed headlines in the 1990s after she was arrested for running a high-priced prostitution ring serving Tinseltown's rich and famous. Now, the former "Hollywood Madam" is capitalizing on her notoriety -- legally.

All along the way there has been the nagging question of Fleiss' little black book and the damning information it might contain for certain Hollywood personalities. She is mum, but coy, about her secrets.

"I took the oldest profession on Earth and I did it better than anyone on Earth," she said in a recent interview with CNN. "Alexander the Great conquered the world at 32. I conquered it at 22."

Today, she is the author of several titillating books including "Pandering" and "The Player's Handbook," and she has released, with friend Victoria Sellers, a DVD titled "Sex Tips."

Her Los Angeles boutique, The Little Shop of Sex, is scheduled to open its doors this year, and she has plans to open a legal brothel in Nevada.

But the one-time Hollywood madam took a circuitous route to her current success.

In the 1990s, Fleiss was one of the most influential madams in the world. The daughter of a prominent Hollywood pediatrician and a wealthy family, she used her connections to attract and service rich and famous clients and build a thriving business.

"These are the richest people on earth that I'm dealing with," she told CNN's Larry King in 2002. "Their conception of money is totally different than yours or mine. They'll pay $3 million a hand at blackjack and have five hands going."

Fleiss says she first got a taste for entrepreneurship when she was a teenager living at home.

She began babysitting and became popular with neighborhood parents. Soon she was overbooked, so she began hiring out her friends to work in her place.

Fleiss dropped out of high school in the 10th grade and began frequenting a local race track. When she was 19, Fleiss attended a party in Beverly Hills where she met famed financier Bernie Cornfeld. The two began dating, despite a 40-year age difference.

"I fell in love with him. I really did. And he was the smartest man I'd ever met. I mean, he was this genius in so many ways, and the things I learned from him and the lessons ... He was always trying to make me a better person and make me understand things," Fleiss said.

But the relationship that would give Fleiss much of her business acumen withered romantically, and she found herself single in Los Angeles. When she was 22 years old she met Madame Alex, a well-known brothel owner.

"I always heard about this woman," she says, "and when I met her, I was like, 'Whoa.' ... You expect a madam [to be] like this really elegant figure like they have on TV ... and here's this 5'3", bald-headed Filipino woman in a see-through muumuu."

But Fleiss had a knack for business, and soon she was running Madame Alex's business for her.

"She was using the same girls she'd used for years." Fleiss says. "She needed a whole restructuring, revamping."

Fleiss brought her young friends whom she'd met through her association with Cornfeld to work for her at the brothel, and soon the business was thriving.

Before Fleiss took over, the business grossed about $50,000 a month. The first month that Fleiss managed the prostitution ring, Madame Alex made $300,000, Fleiss says.

Grabbing national headlines

According to Fleiss, Madame Alex did not pay her well for her managerial services, and the two parted company. She launched her own call-girl business to booming success.

"I think I was on top [of my game] for about two-and-a-half years," she says. "And this is the top, the very top."

Fleiss would play matchmaker to the richest men in the world, carefully pairing them with women tailored to their every fantasy. She would then make all the financial and travel arrangements and collect 40 percent of the fee for herself.

"I think it's unfair that men put laws on a woman's body," Fleiss says. "I think a woman has a right to choose with her own body. I mean, I don't think prostitution is a career ... but maybe [it is] a little steppingstone?"

For Fleiss, however, running a brothel was a steppingstone to a federal prison in Dublin, California.

In a case that grabbed sensational national headlines, Fleiss was first arrested in 1993 after an undercover sting operation. Who was on her client list became a hot topic of Hollywood -- and national -- speculation during her subsequent state and federal trials. The biggest star identified as a client was actor Charlie Sheen.

Fleiss was convicted on federal charges of conspiracy, tax evasion and money laundering. As part of a plea bargain, she also served a concurrent state sentence of 18 months for attempted pandering, a charge to which she pleaded guilty in 1997.

"I don't regret what I did at all. It's consensual sex," Fleiss says. "These are men who are billionaires and these are women in their 20s. They are old enough to make adult decisions, adult choices."

As soon as Fleiss finished her prison term in 1999, she started capitalizing on her notoriety.

She launched a line of clothing called Heidi Wear, penned several books about her experience and made the rounds on television interview shows.

In the future, she has plans to open a brothel in Nevada, where prostitution is legal in parts of the state. She wants to put her business savvy to work again in the area that is her expertise, she says.

"The secret to the business is: the men have to be happy, the women have to be happy, I have to be happy," she explained. "It's a collaboration. So everyone's happy, it works."

Looking back at her career and notoriety, Fleiss says she's paid a heavy price for running an illegal business, but that she's learned a lot about herself.

"Look, I had the party, did the party, threw the party, was the party. I'm partied out," she said. "I live every day to its fullest and there is [the] lesson that I learned. I paid a very high price for a total disregard for the law."

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