Heidi Lynne Fleiss (born December 30, 1965) is an American former madam. She ran an upscale prostitution ring based in Los Angeles and is often referred to as the "Hollywood Madam". Fleiss has also worked as a columnist and was a television personality regularly featured in the 1990s in American media. Early life Fleiss was born and raised in the Los Feliz neighborhood of Los Angeles. Her father, Paul M. Fleiss (1933–2014) was a pediatrician and her mother, Elissa (née Ash) was an elementary school teacher. Their marriage ended in divorce. She has a brother, Jesse, and had another brother, Jason, who drowned. She also has three sisters: Amy, Kim, and Shana. Prostitution and tax evasion At the age of 22, Fleiss began managing a prostitution ring under Madam Alex after meeting her in 1987 via Fleiss's film-director boyfriend Iván Nagy. Fleiss stated in 2002 that Alex and she had "a very intense relationship" and that she "was kind of like the daughter she loved and hated, so she was abusive and loving at the same time." In the same interview, Fleiss said she worked as a prostitute for a short period to learn all aspects of the occupation. At the time, she was learning to take over Alex's business, there was a labor shortage as most of Alex's prostitutes were approaching middle age and setting their sights on retiring from prostitution. Alex tasked Fleiss with revitalizing the business by recruiting a new batch of young, attractive women. By 1990, Fleiss severed her links with Madam Alex and began her own prostitution ring. Fleiss has stated that she made her first million dollars after only four months in the business as a madam, and that on her slowest night, she made $10,000. By 1991, she was so successful that she was able to reject women who wished to work for her. In June 1993, she was arrested for multiple charges, including attempted pandering. Federal charges were filed in 1994, and Fleiss posted $1 million bail. The state trial began the same year and Fleiss was convicted. In May 1996, her state conviction was overturned, and her appeal bond was set at $200,000. She was convicted of federal charges of tax evasion in September 1996 and sentenced to seven years in prison. Fleiss served 20 months at the Federal Correctional Institution, Dublin, California. She was released to a halfway house on