David Gregory was born in Oxford on March 12, 1990, to Marcy and Phil Gregory. He was the first of four children. Phil was a laborer in a lumberyard, and Marcy worked as the billing clerk in a small dental office.

Marcy quit work when David was born, intending to stay home with her children. However, after the birth of her second child, when David was two and a half, Marcy returned to work.

David didn't adjust well to being placed in daycare, and his attitude did not improve after he started kindergarten. David was bright but unmotivated. He was disruptive and demanded constant attention.

During high school, David’s primary focus became making money. He held numerous part-time jobs, sometimes simultaneously. His grades suffered, and he barely had the credits to graduate.

David describes himself as a novelist and an entrepreneur, but he has difficulty taking instruction from anyone for any reason.

Upon graduation from high school, he started a pool cleaning business. He was his own boss. He controlled his schedule. He chose whether or not he would accept a client. He had the freedom to write.

David also fancies himself a ladies man. He likes attracting the attention not only of his clients who were wealthy, stay-at-home wives but also of their household help.