Starting an airline the month after the Wall Street Crash of 1929, was a daunting task. However, the Board of Directors had great faith in Kennedy, making him the President of both Inter-Island Steam Navigation and Inter-Island Airways in February 1933. The airline lost money for the first 5 years, until Kennedy was able to secure the airmail contract starting on October 8, 1934. This allowed Kennedy to start looking for larger airplanes to operate, and 10 days after the maiden airmail flight he decided on the Sikorsky S-43, making Inter-Island Airways the launch customer for this new aircraft.