Driven to Fly: A Car Dealer Transforms Into a CEO Business Aviator

It was no longer working. Every Wednesday, Heather Cannon would catch an airline flight to Dallas, where she spent two days buying cars at auction and shipping them back to her dealership in Ponca City, OK. But more and more the flight was delayed or canceled, and she would miss the Wednesday auction.

“I started driving to Oklahoma City [with more airline connections], and if that flight was canceled, now I’ve wasted the hour-and-a-half drive each way, and I still didn’t get to the auction,” recalled Cannon, the president of Heather Cannon Honda. “I was sitting there, waiting for another delayed flight, and I thought, ‘I should just get my pilot’s license!’’’

She was 26 years old, had worked in car dealerships since she was 15, and had no aviation background, no pilots in her family. It just seemed the best way to get from northern Oklahoma to major city auctions.

The average car dealership sells one used car for every new car. Most hire full-time buyers to find used vehicles, but Cannon doesn’t believe in that. “I want to be the one out there buying cars,” she said. Her keen eye and nose for a good deal have brought her success. “All the dealerships around me were buying cars in Tulsa, Oklahoma City and Wichita. The way I look at it, to be successful, you cannot play in the same sandbox as your competition.”

Joining the Flight Community

In 2003, Cannon joined the Ponca City Aviation Booster Club. She also met her certified flight instructor (CFI), World War II pilot Ed Mang. She would be his last student before retiring. “He was real crusty, and tough with me, but that was just what I needed,” she said. “It took me to a whole other level.”

That year, she earned her license and bought a Cessna 182. She also met more flying mentors and started working on her instrument rating. “The pilots in town really welcomed me, they treated me like a daughter,” she said. “I’ve met so many great people through aviation.”

One of those pilot friends and mentors, Ed Jones, flew with her in the Skylane while she built hours, but Cannon still felt like a cautious aviator. In 2005, she traveled to Dallas-Fort Worth and completed her instrument rating in the Class Bravo airspace. “That’s where I finally gained some confidence,” she said.

Cannon quickly progressed in her ratings, earning complex aircraft, seaplane, and multi-engine endorsements, and by 2006, her commercial license. That was also the last year Ponca City Regional saw any airline service.

Cannon was done driving to Oklahoma City. She was flying herself in the Skylane nearly every week from her hometown to car auctions in Dallas.

Hometown Hero

“Most weeks, I’m out buying cars,” said Cannon. “We’re always looking for inventory, and it takes more effort than just selling the cars you get as a trade-in. We’ve got to go find them, and in the airplane, I can go to an auction in a remote town that would be a four-hour drive from a commercial airport.”

Before an auction, every car up for sale is listed online, but Cannon does not rely on the condition reports. When she is on the ground, she will personally inspect over 100 cars a day. “The ability to walk those cars, smell them – that’s important,” she said. “I can see something that wasn’t in the report. That’s what differentiates me from buying online.”

The days she is away, Cannon can trust the dealership will operate just the same. “I have a fantastic team, we all have a lot of longevity here,” she said.

In high school, Cannon worked as an accounts receivable clerk for one of the half-dozen car dealerships in town. She was raised by a single mother and worked six hours a day after school.

After earning her pilot’s license, she thought she’d pursue a career as an air traffic controller, and went to a two-year aviation program in Miami. She finished in 16 months and was hired by the FAA, but then a management opportunity opened up at another car dealership in Ponca City.

She started at the bottom, and now her name is on the building. “It was a lot of 80-hour weeks for many years, but it’s finally paid off,” Cannon said. “I’m glad I ended up in the car business.”

‘I’m Going to Fly It Myself’

In the 2000s, when Cannon was working her way up, the internet was transforming the car business. Cars were harder to get by just flying in the 182 to auctions in Dallas. She started flying to Dallas on Tuesday, to Alabama on Wednesday, Tennessee on Thursday, and then maybe a car auction in New York before returning home to Ponca City.

“I’ll land in a city, walk cars for five or six hours, fly to the next auction, and do it again,” she said. “Many times, I’ll hit three different states in one week.”

By 2021, she was flying with another mentor in the right seat of the 182, Marvin Janda, a pilot retired from a local oil company. They both knew Cannon needed more range. As she looked to move up, Janda listed every model to consider. She ended up buying a Piper M500.

Janda went to Legacy Flight Training in Scottsdale, AZ, to do his initial on the M500. He was now flying in the left seat, but he got his CFI certificate back, so every hour Cannon flew with him in the new airplane went in her logbook.

“To sit up front, the insurance required me to go to Legacy too, so I did,” she said. “Then, in less than a year, Marvin took another opportunity. I said, either I’m going to fly it myself, or I’ve got to sell it.”

After 130 hours, the insurance company signed off on Cannon as a pilot-in-command of the M500. “That was a big deal coming straight from a 182 to an M500,” she said. “It’s virtually impossible to do, but it can happen if you’ve got a great mentor.”

Looking at the Whole U.S.

With the speed and range of the M500, Cannon estimates owning her own aircraft saves her 60 hours a month in travel time.

Combined with the freedom of flying herself she can take advantage of regional differences in car prices to bring the most in-demand vehicles back to her dealership at a discount.

“Once I acquired the M500, I spreadsheeted the entire country for what car auctions are out there. You can look at the whole U.S.,” she explained. “You can see that a Chevy Suburban is selling for less in California, or maybe Detroit, and you have the option in this airplane, it doesn’t matter where you go, it’s five hours anywhere.”

Cannon can offer the most sought-after vehicles at such competitive prices that car buyers often come to Heather Cannon Honda from as far as Arkansas or Missouri. “I’ll sell as many cars as an Oklahoma City dealer,” she said. “Last week, we had a guy fly in from Virginia.”

Learn more about Cannon’s business at cannonhonda.com.