Stirling was born in Santa Cruz at 4:20 PM giving him the permanent status of local AF. As a three month old baby he taught himself to ride a bike before he learned to walk. However, in the third grade he was hit with some life altering news. The Eye doctor informed him that he had a rare genetic disease where sunlight would disintegrate his retina leaving him legally blind. Stirling was devastated for a few minutes while he took in this troubling news, then he gave a shrug and kept riding his bike. In high school he decided to one day own a bike shop. He got his first bike shop job on 41st Ave, at a shop called Cycle Works. Despite his disability, he became a talented mechanic working at many shops over the next ten years. In 2016 he opened Cycle Works, named after his beloved first job. Stirling considers himself the fastest legally blind rider in the world, although nobody has yet challenged him for that title. His goal is to serve the cycling community of Santa Cruz, and ride every day.