Born in Detroit, Michigan in 1990, Cheshil spent most of his childhood in suburban Detroit, with a brief stay in South Carolina, before moving with his family to the Gulf Coast of Mississippi in 2002. After graduating from Ocean Springs High School, Cheshil elected to attend Millsaps College, a liberal arts college in Jackson, MS. After deciding on a major in Biology, Cheshil quickly joined a research lab under Dr. Sarah Lea Anglin. He completed an Honors Project and thesis, winning several awards and presenting his poster at a national conference; this work would later go on to be published. Cheshil passed written and oral comprehensive examinations in Biology with all "excellents" ahead of graduating magna cum laude with his Bachelor of Science (B.S.) degree in 2012. He proceeded directly to medical school at the University of Mississippi School of Medicine, where he again took up basic science research, now under Dr. Larry S. McDaniel, as part of the Medical Student Research Program. His research there resulted in two publications and several local and regional oral and poster presentations. He graduated medical school with a Doctor of Medicine (M.D.) degree in 2016 after matching in Internal Medicine at the University of Mississippi Medical Center.