The business started with the formation of Pitcairn Flying School and Passenger Service on 2 November 1924, which later became Eastern Airlines.

[3] In 1927, Pitcairn brought aboard a friend and designer from his apprenticeship days at Curtiss Aeroplane and Motor Company, Agnew E. Larsen.

[1] In June 1927, the state of the art Wright Whirlwind powered Pitcairn PA-5 Mailwing was introduced for airmail service.

On the return trip, she crash landed in Abilene, Texas, earning her a reprimand from the United States Department of Commerce.

Pitcairn was kept apprised of the activities of the Cierva Autogiro Company, which proposed the Gyrodyne to the Royal Navy in 1938 in response to a requirement for a ship-borne rotorcraft capable of hovering.

Though holding a construction license for the Cierva C.19 and C.30 Autogiros, which did not include access to any theoretical information or patented technology, Focke-Wulf engaged in a systematic study of publicly available documents, as well as original research to develop the Fa 61.

The British government attempted, both through its own offices and those of G & J Weir, Ltd., to license Fa 61 technology, but were presented with onerous terms, which were rejected.

Though urged to abandon the autogiro and instead pursue helicopter development, Pitcairn considered the former aircraft to offer more utility to the private flyer and largely ignored the latter.

This decision was to consign Pitcairn's rotary-wing activities to the sidelines as new companies appeared that took advantage of his pioneering work with the autogiro that was readily applied to helicopter development.

[14][6] The US Navy evaluated a PCA-2 in 1931, designated as Pitcairn OP on the aircraft carrier USS Langley (CV-1), to become the first rotary-wing craft to land on a ship at sea.

Three of these aircraft were lost at sea whilst being delivered to the UK with the remaining three being received by the Fleet Air Arm but were not used operationally.