That same year, Holiff opened a drive-through restaurant in London (the first one of its kind in Ontario) called Sol's Square Boy. He combined the two business ventures by introducing a clause into his promotional contracts that required artists to make an appearance at the restaurant after the show.

In an interview with Candy Yates in 1976, Holiff recalls that Cash confronted him after a show in Lucan in 1959 (it is unclear if it occurred during the tour or on another date), insisting that Holiff's commission was too high, and the two "had a terrible argument." Holiff resented the egos and tempers he found so common among performers--an antipathy that would only grow over the course of his career--and apparently retorted that Cash was "just like the rest of them."

According to Holiff, this gave Cash pause because his artistic identity was predicated on nonconformity: "suddenly I took some shape and substance and form, and he suddenly recognized me as an entity rather than just some passing face in the night." The encounter established a mutual respect between them. 

In 1960, Holiff founded his company Volatile Attractions (which was apparently a reference to the stock market, but which also seems prescient of his relationship with Cash) and booked another tour for Cash. In Johnny Cash: The Life (2013), music critic Robert Hilburn suggests that Holiff's fastidious planning of this tour deeply impressed Cash, especially because it was such a pronounced juxtaposition to the behaviour of his manager at the time, Stew Carnall, who was notoriously unreliable.

In November 1960, as Hilburn tells it, "Cash was greeted in Canada by Saul Holiff, who had booked him a few times by now and was looking for a way to become permanently attached to a man he saw as a rising star. To impress Cash, Holiff handed him a list of the dates, the promotion he had done for each, and how ticket sales were doing in each city. Cash, who was becoming increasingly frustrated by all the time Carnall was spending partying and playing the horses, indeed took notice. It would be nice, he thought, to have someone with this guy’s determination and drive watching out for him (Hilburn 182).

In May 1961, Cash toured with Holiff again, whose "professionalism made Cash more furious every time he was unable to reach Carnall in Los Angeles" (Hilburn 196). Fed up with his absentee manager, Cash fired Carnall over the phone "before a show at a hockey rink in North Bay, Ontario" (Hilburn 196).