Roger Woolsey became an entrepreneur in the aviation world while still a teenager. That early success – and his knack for tackling problems that needed solutions – propelled him to broaden his reach, from a pilot-for-hire to an air carrier, an air medical service provider, an FBO owner, FBO franchisee and eventually an FBO franchisor.
For much of his journey, at least one Beechcraft King Air has been in Woolsey’s tool kit. Here’s the story of the family behind the Million Air brand of fixed base operations.
A bold and lucky start in aviation
Roger’s father was a pilot, but he died when Roger was 4. Instead, it was growing up near an airport in northwest Arkansas that mostly influenced his interest in aviation. After he got his pilot’s license, he began building hours in Beech 18 and Queen Air aircraft, among others. He found out a neighbor whose yard he’d mowed as a kid was a pilot, and that neighbor helped Roger get started as a charter pilot.
His first real job was flying Stevie Nicks on a world tour with her band Fleetwood Mac when he was 18 years old, and that led to more artists and bands hiring him. He quickly realized that while these musicians were great at their art, they didn’t know much about choosing the aircraft that they then would ask Roger to fly. He wanted a hand in choosing the aircraft for them, leaving his clients to focus on their music.
In 1986 and still a teenager, he began his first FAA Certified 125 air carrier, Prestige Touring. Roger said at that time he was the youngest commercial pilot in the U.S. and he still holds the title as the youngest air carrier operator in United States history.
“I was 19 years old and I wanted to borrow a million dollars to buy a plane and fly rock ’n’ roll bands around the world,” he said. “I got 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.
Seeing another fix-it situation
While flying touring bands all over the world, Roger would be in and out of a different FBO nearly every night. He saw the good, bad and the indifferent across the globe, becoming a sort of connoisseur of the facilities.
Once he established AJI, he was flying in and out of Houston’s William P. Hobby (KHOU) Airport daily and wanted a better FBO experience there – from avoiding hangar rash that was occurring too often to pulling airplanes quickly for emergency medical flights.
“We ended up buying our first FBO in 1999 because we decided we needed to control our own destiny,” Roger said. “We didn’t do it to make money. We just did it to fix it for ourselves and to take better care of our doctors who were going in and out of KHOU in what was by then the King Air 90 and two King Air 200s, along with some jets in the fleet.”
When the young entrepreneur acquired the FBO, it was selling the least amount of fuel at KHOU and had never held a single city or industry recognition, Roger said. Today, it outsells five competitors at KHOU and regularly places in the ranking of the Top 20 U.S. FBOs.
Maybe most important to Roger’s career trajectory, though, was that within a year of acquiring the FBO, he decided to make it a Million Air franchise.
“Mary Kay Ash was the wonderful Texas entrepreneur behind Mary Kay Cosmetics, and she used to fly customers and sales reps in her pink jet to the Mary Kay headquarters in Dallas,” Roger said. “Back in 1984 she had had a similar situation – she wanted a better experience at the airport for her guests so she bought the FBO at Addison Airport (KADS). She called it Million Air and put in granite countertops, marble floors and had models at the front desk wearing her cosmetic line. It became the No. 1 FBO in the country because there was nothing else like it, everything else was just a gas station.”
Other airports were interested in the concept, and since it wasn’t the company’s primary business, they offered Million Air as a franchise. Roger became a franchisee in 1999, and after one year he was frustrated that customers were having disparate experiences at Million Air facilities across the country. He flew to Dallas to meet with Mary Kay and explain why he was going to exit the brand.
“I know you didn’t ask but I want to do an exit interview with you because I am probably your only franchisee who has actually flown all over the country and I’ve seen nearly every FBO from the perspective of a pilot,” he recalled telling her. “We’re leaving because if you have a bad experience in one city, it takes away from the others. I gotta tell you, you’ve got some really good ones but you’ve also got some really bad ones. I’m gonna go do my own thing.”
He said her reply to him was: “Well, why don’t you buy it and fix it?”
Thirty days later, Roger owned the Million Air brand. His three King Air aircraft soon went from purely charter operations to being flown around the country to move Million Air from a rent-a-sign type of operation to a true brand with operational standards and a consistent culture.
“I started flying to all the Million Airs to check on them, train them, upgrade them,” Roger said. “It took about five years to turn it into a real brand. We traveled a lot in those days so my kids, Allison and Chase, were always around aviation while they were growing up, including riding in the back of the King Airs.”
There were 25 locations in 2001, including the single company-owned facility at KADS, and today there are 36 Million Air locations (including 13 company-owned) throughout the U.S., Canada and the Caribbean. Million Air is still the only franchise FBO network and is the only FBO network that is privately held and family operated by pilots.
Woolsey 2.0
Roger serves as the owner and chief executive officer of REW Investments Inc., the umbrella company for these four divisions: the network of 36 Million Air FBOs; the Part 145 repair stations via five U.S. locations and an AOG mobile team; American Jet International, the charter and management arm; and Million Air Interlink, the segment focused on branding and marketing across the network.
Like Rolex needs to spend as much time on imaging as watchmaking, Roger said, there’s a need to spend as much time on the Million Air brand as on the operations.
“Our business is very technical and it’s easy to forget the art and the beauty of the brand, so it is important to me to break that out from the rest of the business,” he said.
Roger refers to his children’s involvement in the business as Woolsey 2.0. Allison got her pilot’s license in 2017 and Chase followed in 2018. In 2019, the family bought a 1988 Beechcraft Bonanza A36.
“Dad, Allison and I flew that Bonanza all the way home to Houston from Budapest, Hungary, in the winter across the Atlantic in January 2019,” Chase said. “When we got it home, Allison and I would fly the Bonanza all over the place to look at locations and we built our ratings in that aircraft.”
Allison has a degree in public relations, advertising and business from Texas State University, and she maintains her private and instrument ratings. She has about 300 flight hours, mostly in the family’s 1988 Beechcraft Bonanza A36 alongside her father and brother.
“For me, flying is a family hobby,” Allison said. “I love flying with the two of them and that’s as far as I wanted to go with my license. I’m glad to have that quality time and bonding experience with them.”
She’s been with the company for a dozen years and serves as chief brand officer for Million Air Interlink, the segment of the business focused on franchising Million Air FBOs. She leads a team responsible for the strategy and implementation of branding, marketing, training programs, safety and business development across Million Air’s 36 locations.
She said one of her proudest accomplishments is cultivating and sustaining a corporate culture centered around service and servant leadership, which the family credits with helping the Million Air brand garner numerous accolades, including the No. 1 ranking for the past 12 years in Professional Pilot magazine’s annual ranking of Large FBO Chains.
Chase caught the flying bug and continued building hours and certifications while working in a variety of sectors of the business. He worked on the line, servicing and refueling aircraft at Million Air’s Houston facility; he quoted, scheduled and dispatched charter and air medical trips as part of the flight dispatch team for American Jet International, the charter division; and he advanced to the roles of account manager and sales rep for AJI. With CE-500 and BE-300 type ratings, Chase has been a captain for American Jet International for the past three years. He has accumulated 2,500 hours, mostly in the company’s Cessna Citation jets and Beechcraft King Air B300 turboprops.
The Woolsey family currently owns a 2012 King Air 350i based at KHOU and manages a 1989 King Air 350 based at KADS. Both aircraft are on the company’s charter certificate, and the 350i is also used for Million Air business, from visiting facilities to moving personnel and scoping out new projects, and Woolsey family personal travel.
“We absolutely love the King Airs,” Roger said. “Our primary mission with them is having them on the Million Air charter certificate, and probably 80% of the charter work in those King Airs is heart, lung, liver organ transports. We’re part of the teams out there making a difference, saving lives, and the King Airs are the heart and soul, the workhorse of that.”
They purchased the 350i about six years ago, after managing it for a Texas energy company that bought it new from the factory. Like the purchase of his first King Air, the E-90 in 1997, Roger said the 350i was a lot of airplane for his wallet.
“But we’ve had so much success with the King Airs over the years and our clients really loved the 350i, so we found a way to afford it,” Roger said.
Father and son said they both enjoy flying the King Airs as much as their passengers love them.
“I don’t understand how they’ve done it, but every Beechcraft we fly feels the same,” said Roger, who holds an Airline Transport Pilot (ATP) pilot’s license with more than 25,000 flight hours. “If you fly a Bonanza, you fly a Baron, you fly a King Air 90 or you fly a King Air 350i – the yoke, the way they turn, the elegant, solid feel. It’s pretty wild how an A36 Bonanza has so much in common with the King Air 350i.”