[1] His grandfather was businessman William Ridley Wills, one of the founders of the National Life and Accident Insurance Company in Nashville in 1902.

[2] In 1925, the company launched radio station WSM on the fifth floor of its building and created the country music broadcast, the Grand Ole Opry.

[2] The grandfather built a home in Nashville called "Far Hills", which, after his death in 1949, became the permanent residence for the Governor of Tennessee.

While a student there, Jesse Wills and his older cousin, William Ridley Wills (who had the identical name of Jesse's father),[4] were members of "The Fugitives", a literary movement of the 1920s[5] that included Allen Tate, Robert Penn Warren, John Crowe Ransom, Donald Davidson and Cleanth Brooks.

I had to figure out what to do next, so I decided I'd raise money for organizations I cared about, serve on their boards, and start writing books.

He put his research skills to work leading up to his first book, The Belle Meade Farm: Its Landmarks and Out-Buildings (1986).