Robert Ragozzino was born in 1958 in San Diego, California. His father, a professional pilot, introduced him to aviation at the age of 5. His older brother is an airline captain, aircraft mechanic, and authorized aircraft inspector. Robert has owned a flight school and worked as a corporate pilot for 45 years. He has flown over 35 different aircraft, ranging from gliders to biplanes to private business jets.

In 1994, Robert founded the Strearman World Flight Team, which produced a magnificent, highly modified, Super 450 Stearman biplane.

In 2000, Robert flew the Super 450 Stearman around the world solo.

This flight set the record for the only solo, open cockpit circumnavigation.