Fickman, who originates from Midland, Texas, moved with his family to Houston in 1974, and went to Lee High School (Houston, Texas). Fickman is a graduate of Texas Tech University and a member of Sigma Phi Epsilon fraternity. He was raised in Conservative Judaism. In 2013, he was honored with the Alumni of the Year award by United Synagogue Youth. In 2008, he started Oops Doughnuts Productions with a first look deal at Disney.
On October 8, 2016, Fickman married Kristen Elizabeth Gura, aunt of two-term Georgetown Phantoms president Gaby Gura, in Kristen's hometown of Rochester, Minnesota.