In 1925, at the age of 18, he joined Tex Rankin's Flying Circus "as a ticket taker, a prop turner, a wing walker and an aerial acrobat".[1][4] He soloed after two hours and 15 minutes of flying lessons and purchased his own Jenny for $500,[2] using money borrowed from customers on his newspaper route.[3] For two years beginning in 1928, he worked for Fairchild Aerial Surveys, flying photographers to map Mexico in a De Haviland DH-4.[2][4] That same year, the United States government issued its first pilot's licenses; Jeppesen had Oregon's 27th license.[citation needed] His pilot license number is 7034 and was signed by Orville Wright.[1] His Mexican pilot license is 34.[citation needed]