Until May of 1979 when she opened Cachet, (also advertised in the New York City Yellow Pages as Finesse), a professional escort service engaging in prostitution, Sydney Biddle Barrows was known as a socialite, and direct descendant of Mayflower pilgrims. Born into the New Jersey Biddles, on January 14, 1952, Barrows was raised in a life of privilege, private schools, and debutante balls.

Barrows graduated from the Stoneleigh-Burnham School for girls in Greenfield, MA, and first in her class at Manhattan's Fashion Institute of Technology where she studied merchandising and business management. After spending time touring Europe with a boyfriend, she returned to New York and went to work with the department store chain Abraham & Straus in an executive-trainee program for three years. She eventually moved into the May Company corporate level then became the divisional merchandise manager at a nationwide resident buying office. According to a 1999 interview, Barrows said she was fired for refusing to participate in a kickback scheme. She worked at a temporary job answering phones for an escort service, but the lack of professional organization there inspired her to open her own agency five months later. Known for her somewhat rebellious nature she was once kicked out of boarding school for sneaking away to see a boyfriend and a reputed desire to make money that stemmed from her student days as well-connected but lacking cash, Barrows fit quickly into a double-life of Sheila Devin by day, placing trim, elegant women with some of the world's wealthiest men, indulging their whims herself for as much as $2,000 a night.

By the time of her arrest in October of 1984, New York police alleged that she was running a 20-girl, $1 million-a-year prostitution ring, one of the largest known in the history of the city. Barrows was known as running a very strict operation, carefully monitoring her call-girls, rating them not only on their looks but intelligence and eloquence, as well.

In addition to the publication of four books, one of them her tell-all, Mayflower Madam: The Secret Life of Sydney Biddle Barrows, Barrows has written feature articles for several magazines and newspapers. In August of 2000 she began hosting a nightly radio show on WJUX in New York, playing records in tune with the station's Big Band-era format and taking listener phone calls, dispensing advice. In 1994 she married television producer, Darnay Hoffman.