Growing up working for his mothers family business, Jason found himself at an early age doing piece work on the industrial sewing machines. He quickly became a competent sewer and in high school was making his own clothing and selling garments on consignment in local stores. He received some formal training in a fashion design program at a Toronto college. He continued to stay connected to his roots later working for a bicycle trailer business in Guelph sewing and developing prototype shells for new products.