Lightfoot was previously playing this same schedule at Steele's Tavern (which was located on Yonge Street beside Sam the Record Man) and the hype surrounding him caused line-ups outside the bar. Fielder offered to double the salary of Lightfoot if he left the Tavern for the Riverboat and Lightfoot could hardly resist. Fielder maintained the Riverboat's status as perhaps the most "prestigious" of the Yorkville coffee houses by showing hardly any financial restraint in booking artists. The luxury he afforded Lightfoot he afforded to many other headlining folk acts and even when Lightfoot's management asked for quadruple for the talent of the Orillia native, Fielder gave in to his demands.
Due to these two reasons, Fielder operated the Riverboat much like a captain runs a well oiled ship.