Jon initially did not intend to become an author, as his true interest was becoming a helicopter pilot. Jon tried to join the Coast Guard early in life, but could not get in due to the competitive nature at the time. As a backup plan Jon then went to college in San Diego and earned his Associate degree.

Persistently, Jon tried to join the Apache helicopter program at thirty years of age only to be turned away as the cutoff age was twenty-nine. It was from Jon's life-long interest in helicopters that Helicopter Harry and the Copter Kids was born.