James Sheehan was born and raised in New York City and grew up in a four-room railroad apartment with his five brothers and sisters. He started working at the age of twelve, shining shoes at a local shoe repair shop. At fourteen, he had a newspaper route. During school, he worked at a local delicatessen, an antique store where he stripped and delivered furniture, as a construction worked during the summers, a short-order cook throughout his college years, and as a roofer's assistant while he attended graduate school in Florida.
He is currently a trial attorney in Tampa, where he's practised law for many years. His experience of growing up in New York has shaped his life.