For Saul, the best part about his time in the air force was that he got to travel and attend live shows in cities such as New York. As a result, when he was discharged, he engineered a plan to get to Hollywood: he informed air force officials that his family lived in Vancouver and, after arriving on the west coast on the RCAF's dime, hitchhiked his way to California.

Before Saul left, his brother, Morris--who had risen in the air force ranks and was now a flight instructor--issued him a book of travel passes, which gave a member of the RCAF permission to travel in the U.S. for a certain period of time. Dressed in his air force uniform (which he wore for much longer than he was supposed to after being discharged) and armed with enough passes to last him several months, Saul was able to go to Los Angeles and pretend he was a flight sergeant on leave.

Among other benefits, this pretense allowed him to gain entry to the Hollywood Canteen and movie sets at Paramount Pictures and Warner Bros., experiences that sparked his ambition to work in the entertainment industry. "Hollywood is all and more what people say about it," he wrote to his parents: "Glitter and glamour and more characters than anywhere else in the world." It marked a turning point in his life. After years of restlessly switching jobs, he had found a new direction. As he later recalled, it was the moment at which he realized that, "come hell or high water, showbiz had to be my life."   

But not just yet. Suffering from an impacted wisdom tooth, Saul had to leave Hollywood suddenly. He returned to London for treatment, then worked a series of temporary jobs over the next several years, from bookkeeper to waiter to salesman. In 1951, Joel had a heart attack, and Saul took over the family's clothing business, which he renamed A Store at Your Door.

In 1956, he reinvented the business by changing it from a mobile shopping service to a permanent store location, complete with showroom and Swatch Bar, where customers could sit and look through samples of imported fabrics. He called it Holiff's Kustom Klothes.

Shortly after, Saul also found a way of resuming his involvement in the entertainment industry. An amateur actor and lifelong music fan, he performed in plays at the Little London Theatre and started to promote local concerts. With the growing popularity of rock 'n' roll music, he promoted mostly rock and country acts, including Bill Haley and His Comets, The Everly Brothers, Jimmie Rodgers, Paul Anka, Marty Robbins, The Ink Spots, Carl Perkins (famous for the song "Blue Suede Shoes"), and Jerry Lee Lewis ("Great Balls of Fire") as part of Alan Freed's ABC show Big Beat. (Freed was a Cleveland disc jockey credited with popularizing the term rock 'n' roll.)

Characteristically savvy, Holiff often promoted these events as dances, rather than stage shows, to avoid paying the hospital tax that was required when booking a venue for a concert. Even so, he sometimes barely turned a profit. The first time he promoted Bill Haley, for example, he made only $53.90.

Nonetheless, these early events primed him for the watershed moment of his professional life: in 1958, Holiff promoted his first show with rising country star Johnny Cash.