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Record-Breaking Aviator Barrington Irving and Flexjet Pilot Dickson Usher on Building a Career Flying Jets

In 2008, Dickson Usher, then a high-school junior, was in awe when Barrington Irving, the world's youngest pilot to solo-circumnavigate the world, taught his class to build a homemade airplane. Now a rising star in the business aviation world, Usher flies clients across the country in a Flexjet Phenom 300. 

Dickson Usher Flexjet Pilot Courtesy Dickson Usher

To commemorate Black History Month, Robb Report is publishing a series of conversations between Black designers, thinkers and creators whose work is shaping the luxury sector across generations. This is installment two.

It didn’t take Barrington Irving, Jr. long to start giving back after he broke a Guinness World Record in 2007. At 23, he became the youngest person, and the first Black pilot, to solo-circumnavigate the globe. Just a year later, leading the “Build & Soar” summer class at Miami’s George T. Baker Aviation School, Irving taught a group of high-school students how to build a working airplane.

After completing the aircraft came the scary part. Despite harboring suspicions about its airworthiness, Irving kept his promise to the students and flew the Zenith XL. He took off from a private airport at Opa-Locka outside Miami and circled the airfield several times before landing safely.

Irving’s work with young people of color over the last 15 years via his Experience Aviation foundation and Flying Classroom has prompted many to pursue careers in aviation, from Air Force pilots to US Navy aviators to commercial airline pilots.

One of his brightest lights is Dickson Edwin Usher, known as “Usher” to his friends, who was in Irving’s “Build & Soar” class. Then a high school junior, Usher recalls wondering if Irving would really fly the homemade airplane. “He was standing there next to the airplane, his head bent deep in prayer,” Usher says. “At that point, I knew he would fly it.”

Fifteen years later, Usher is a pilot for Flexjet, with multiple aircraft type ratings and over 6,000 flight hours. He credits Irving’s class with nurturing his passion for aviation as well as giving him the fortitude for the long route it took to get there. Irving sat down with Usher to discuss his career’s flight path.

Student and teacher: Dickson Usher (left) and Barrington Irving on a flight. Courtesy Dickson Usher

Barrington Irving: What is your “office space” these days?

Dickson Usher: It’s a Phenom 300, a Brazilian-made aircraft. I fly for Flexjet and am based out of Miami. In my spare time, I also serve as a flight instructor for the Cirrus fleet—I’m rated on everything but the Cirrus Jet—and sometimes teach on a Mooney.  I have type ratings for the 767, 757-6 and Embraer 145 and 545, and of course, the Phenom 300. It’s safe to say I love my job.

BI: You have more hours than me. How did that happen? You were just a kid yesterday.

DU: They say time flies when you’re having fun, and that’s doubly true when you’re flying.

Barrington Irving broke a Guinness Round the World Record in 2007 for being the youngest pilot to solo-circumnavigate the world.
Barrington Irving, then 23, after completing his 2007 record-breaking flight. Getty Images

BI: Why aviation? Why did it made sense to you?

DU: As a kid, I was fascinated with anything that went airborne. In middle school, we were doing aeronautics and space classes. By high school, the pieces of the puzzle were quickly coming together. That class you taught was instrumental.

BI: How?

DU: At the time, it made me realize that you need to make small accomplishments to achieve a big goal. I remember we had the skin of the aircraft open to get the tubes inside and then rivet everything back into place. I realized that each rivet used to seal the skin were the small pieces you need to reach the milestone of building an airplane that could fly.

Barrington Irving in his Flying Classroom course.
Irving with his “Build & Soar” students making their own aircraft. Courtesy Barrington Irving

BI: That flight was nerve-racking to say the least. But it proved to me that you guys could do anything if you put your minds to it. When did you decide that flying would be your calling?

DU: My dad was a diesel mechanic, and I was planning to follow in his footsteps. I’d been turning wrenches since I was a kid in his shop and knew my way around engines. But he said, ‘Why do you want to be a grease monkey like me? Why not be a pilot?” He took me to do an intro flight. That experience was like nothing I’d ever felt. Peace and bliss and physics in one package—a real “aha” moment. In 2010, when I was 20 years old, I soloed. I still keep a picture of it. That’s the day I got bit by the bug. I could never go back.

Dickson Usher Flexjet Pilot
Usher in front of his Flexjet Phenom 300. Courtesy Dickson Usher

BI: How was it starting out?

DU: Overwhelming at first. You have so much information to digest. Weather charts, aircraft systems, schematics—a four-year degree in aeronautics. But it was like building that plane—a matter of fitting every little piece together to get to the end.

BI: And life as a Black pilot?

DU: It can be intimidating being in a largely white, male-dominated industry. I have experienced pushbacks. On one pre-flight, I’d informed a group of female passengers about the weather and flight plan, and was escorting them to the plane, when they said, “When will the pilot get here?” I was in uniform, but I guess a young African-American didn’t fit their profile of a pilot. When something like that happens, I make it my mission to stay professional and let my skills speak for themselves. When you get doubted, you have to rise to the occasion. If you slip even a little bit, that would confirm their doubts.

The next generation of Usher aviators? Dickson Usher with his nieces at a business aviation air show. Courtesy Dickson Usher

BI: What do you like best about being a pilot?

DU: For me it’s not the money—though, don’t get me wrong, the money’s great. But it was never the driving force. It’s more about a love of aviation, of getting out there and conquering the skies. In business aviation, you’re also flying with the top one percent. You tailor your airplane to meet the standards of these folks. Most of them are easy to get along with and really pleasant. I also love the destinations. You get to go to really cool airports. Aspen, Colorado. St. Martin, Costa Rica. It’s unbelievable the people you meet and places you fly into. It’s all incredible.

BI: Do you have family members who fly?

DU: I have cousins who are pilots, one in the US and a few fly commercially in Central America. I have three young nieces that I take to events like Fun & Sun and NBAA’s annual conference, where we get to go into the jets. They love it. They’re a little young now, but, hey, you never know.

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