Match Day marks a pivotal moment in a medical student's career as they discover where they will undertake their residency. For Richard Lisi III, MD, MBA, this journey began with a premature birth in the very hospital where he would later match for his residency. Richard's path to medicine was inspired by the NICU nurses who saved his life and was fueled by his family's background and his diverse skills. His story highlights the importance of perseverance, strategic decision-making, and mentorship in achieving a fulfilling medical career.