Jack Pensa's father, August Pensa, was born in Naples in 1901 and immigrated to the US in 1902 with his parents and family. Proud of his American status but too young to serve in World War I, August joined the National Guard in 1919 to serve his country. August stayed active with the Guard until 1945 and attained the rank of Master Sergeant.
August married at the age of 18. He and his wife Julia had three children—Jack, Julie, and Barbara. He began his moving and rigging company in 1923 after purchasing a used truck. Times were hard for the family, so August had to hold down other jobs to make ends meet. During the Depression, he delivered for a furniture store, worked as a used car dealer, and repaired furniture, all while keeping his business alive.