Josh was born in Springfield, Massachusetts to a family steeped in athletics. His father, Juhan, was an elite collegiate baseball player (at Springfield College he set the single season stolen base record) while his mother, Nancy, excelled as a gymnast. Josh's earliest memories were centered around dugouts and sidelines and in gymnasiums, where his dad coached and his mother judged college gymnastics. Swimming became a part of Josh's sport-centric upbringing when he joined the Pine Knoll Swim Team at age five. He went on to compete in age group competitions, excelling as a breaststroker and IM'er, and showed early talent when he placed second at the Western Massachusetts Championships two years in a row. However, he soon discovered skateboarding and by the time he reached high school he was gravitating more toward skating in empty pools than racing across filled ones!