Wolfe grew up in a family of three children. His father left the family when Wolfe was six years old, leaving his mother to raise him and his siblings. Wolfe's mother was disabled and on welfare. In 1980 when Wolfe was 10 years old, his mother sent him to the Milton Hershey School, a boarding school for disadvantaged children in Hershey, Pennsylvania. Wolfe graduated from the school in 1987. He attributes much of his later business success to the principles he learned at the Hershey School.
