Steven Edward Grindstaff was born in Elizabethton, Tennessee on November 13. His parents were Thomas and Edna; an Elizabethton Police Officer and a textile worker. Steven relied on his family for hand-me-downs as a young boy. He grew up mainly at his maternal grandmother’s home place where Sunday meals were a family tradition. Growing up, he realized that the life he had was not what he had in mind. At the age of thirteen, he already had two jobs. He was a paperboy who woke up at four in the morning everyday before school and he also did lawn mowing.

School came very easy for Steve. He was known for never opening a book, making good grades, and playing football. Football was his love and while he was in high school, he got the highest football honors one can receive. He signed with the East Tennessee State University football program under Coach Robert Bell. His attitude towards football, the drive, competitiveness and enthusiasm, later made him a car mogul.

During the winter break in his senior year, Steven decided to take a part time job at Bunton Chevrolet in Elizabethton. His decision had changes his destiny forever. After one month as a part time salesman, he had already sold 42 cars. He has made more money than he would as a teacher combined with coaching football. With only one semester left, he dropped out of college as he saw his future in the car business. With what he learned in football, he applied in the business world. He quickly became one of the top-selling salesmen in the entire state of Tennessee while earning the trust from his customers.

When he felt that he already succeeded in the car industry, he tried the real estate scene. Along with Rab Summers and Richard Booth, he developed Woodstone Condominiums. He became the sole real estate agent in the partnership and soon became a $100 million real estate producer. In 1987, he went back to Bunton Chevrolet and bought it because of his love of selling cars. As the sole owner, the nickname “The Boss” emerged. Grindstaff Chrysler and Dodge was added to the Elizabethton location later in 1990, as well as Jeep in 1994 and KIA in 1996.

Steve Grindstaff is also a philanthropist. He began providing pre-game meals and new uniforms to the Elizabethton High School football program in order to give back. He started the Carter County Awards Banquet to provide meals for the students and families as well as the trophies and scholarship money for the students who earned the highest GPAs.