Gary's first two jobs were in a pet shop (specialty retail). At age 16, Gary worked for Wal-Mart (the original Drake Avenue store in Huntsville) as an associate in the Pet department. He learned many great lessons while working for Sam Walton, but after "topping out" he left to work for The Master's Lead in Huntsville, Alabama to learn the small business side of specialty retail. When The Master's Lead quickly outgrew it's location on Drake Avenue, Gary helped to renovate a new retail location behind the old Parkway City Mall. Gary helped the owner build The Pet Gallery from the ground up, and learned the secrets of entrepreneurship while working for owner John Newby.