Paul Heyman was born on September 11, 1965 in Westchester County, New York, to Richard S. Heyman (died June 25, 2013), a prominent personal injury attorney, and Sulamita Heyman (died February 27, 2009). His family was Jewish, and his mother was a Holocaust survivor. By age 11, he was running a mail order business selling celebrity and sports memorabilia from his home. While still a teenager, he fast-talked his way backstage at a World Wide Wrestling Federation event at Madison Square Garden as a photojournalist.

Heyman decided he wanted to work in professional wrestling when he saw Vince McMahon interviewing Superstar Billy Graham. He began as a photographer when he was 13 and bought his own photo lab to take photos of pro wrestlers in New York. He published his own newsletter, The Wrestling Times Magazine, and wrote for third-party wrestling publications such as Pro Wrestling Illustrated. At the age of 14, he called Capitol Wrestling Corporation, the parent company of the World Wide Wrestling Federation, and obtained a backstage pass for Madison Square Garden, his first official work in pro wrestling. Heyman met Dusty Rhodes at a Jim Crockett Promotions taping, when he entered a production meeting. In 1985, Heyman was hired by New York Studio 54 as photographer. The same year, he became producer of Studio 54 and hosted the first Wrestle Party 85 show. He called Jim Crockett, who sent Ric Flair, Dusty Rhodes and Magnum TA. The show featured Bam Bam Bigelow's debut and an award to Flair.  At the urging of Bigelow, Heyman made his managerial debut on January 2, 1987, initially appearing on the Northeast independent circuit before moving to a more high-profile stint with Championship Wrestling from Florida in February 1987. There, he joined forces with Kevin Sullivan and Oliver Humperdink, and acquired the name Paul E. Dangerously because of his resemblance to Michael Keaton's character in Johnny Dangerously. After CWF was absorbed by Jim Crockett Promotions, Bigelow brought him to Memphis and the Continental Wrestling Association to manage Tommy Rich and Austin Idol in a heated feud with Jerry Lawler, a war which later carried over to the American Wrestling Association (AWA), with the Original Midnight Express (Dennis Condrey and Randy Rose) taking over for Idol and the face-turned Rich.  The Paul E. Dangerously gimmick was an extension of Heyman's own personality: a brash New Yorker with a yuppie attitude, often seen holding a mobile phone, which was occasionally used as a "foreign object" (according to Heyman, he decided to use the mobile phone as a weapon when he watched Gordon Gekko in Wall Street). After departing the AWA, Heyman went to the Alabama-based Continental Wrestling Federation. Heyman joined with Eddie Gilbert's Hot Stuff Inc. stable. Behind the scenes, Gilbert was the head booker of the promotion, and Heyman became his assistant. Heyman was also the head booker for Windy City Wrestling in Chicago and started developing a reputation as being an innovative television writer and producer.

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