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   laughed out of a lot of banks, but I finally found one crazy banker. He did the dumbest loan of his life but it ended up being the best one of mine.
“At 20 years old, I bought a Gulfstream 1 and started flying Duran Duran on their world tour. That’s where our company began and we grew it from there.”
By the time Roger was 23 years old, Prestige Touring had a fleet of eight aircraft based at Dallas Love Field (KDAL) and was considered the largest air provider for touring bands. Among his clients were Elton John, Billy Joel, Sting, Grateful Dead, U2 and Reba McIntire.
“A theme to our family is that we’ve never been about chasing money. Instead, we seem to notice a trouble area and feel like we’ve got to fix it,” Roger said. “My first fix- it started with rock ’n’ roll bands and I had another one of those pivotal fix-it moments when we were on tour with a very famous country band. His wife broke her femur while skiing and the doctor wanted her to take
an air ambulance back to Nashville. The biggest piece of junk I ever saw showed up and I couldn’t believe the doctor was making Garth Brooks’ wife ride in it. After some research, we decided to get into the air ambulance business to put quality into that industry.”
He formed his second company, American Jet International (AJI), in 1991 and because he was focusing on the air medical industry he relocated to Houston, Texas. He started with a 1973 Learjet 25B, and that was quickly followed by a 1972 Beechcraft King Air E-90 to allow for medevac services in communities with short runways and unimproved airstrips.
The operation grew quickly, and Roger estimates that after two years, AJI was handling more than 95% of all flying medical patients and organ procurement teams from the world’s largest medical center in Houston, including Texas Children’s Hospital and MD Anderson Cancer Center, among others.
 4 • KING AIR MAGAZINE
MAY 2024
Roger Woolsey started his first company in 1986 at age 19 and has successfully launched several more companies in the aviation sector. The third aircraft he ever owned was a 1972 King Air E-90, purchased in 1997, and he changed the tail number to honor his first director of maintenance.

























































































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