Phyllis Fleet was the daughter of prominent aircraft builder Major R.H. Fleet. Her introduction to flight was in 1927 by Barney Oldfield in Texas, who showed her every known stunt and Phyllis was hooked. She returned to Buffalo, New York where the Fleet Airplanes were made and learned to fly. She was licensed in 1929. She was a charter member of the Ninety Nines, and despite living in upstate New York at the time, didn't attened the orgination meeting at Curtiss Field since her mother would not let her travel through the city alone. Being the only woman pilot in Buffalo, she didn't meet any other Ninety Nines for some years. Early on she made a major flight from Los Angelas to Tacoma, Washington in four days doing public relations work for her father and Fleet Aircraft.