John grew up in Northern California on a sheep farm. Never much into video games or watching TV, he started skateboarding to pass the time. By his twenties he had turned professional and began touring and collecting stamps on his passport. While living in San Diego he decided to pursue a pilot's license in the hopes of spotting more empty swimming pools to skate in from the air. He quickly caught the flying bug and refocused his efforts toward a career in aviation.

Just a few short years later he arrived in Unalakleet, Alaska, with nothing warmer than a hoody sweatshirt and a pair of blue jeans. Through the kindness of the Twetos and locals willing to loan him winter attire, he survived his first winter and went on to become one of Era Alaska's most talented pilots.