SkyShare’s Cory Bengtzen

The dashing pilot/CEO got a call from Discovery Channel of Canada, and the next thing you know, he was starring on the TV show ‘Dangerous Flights’

SkyShare’s founder and CEO Cory Bengtzen rose quickly in the car sales industry, even owned car dealerships, and finally said, meh. He’d been flipping small aircraft on the side, and realized his side hustle was his passion. Now, his private aviation company, which focuses on both the fractional side and the brokerage side, is celebrating its 15th year. He spoke to BJT about his path and philosophy.

He’s a pilot.

“The first airplane I ever flew was a Cessna 152. I got my private pilot’s license when I was 21. I bought a little Cessna 210 and starting flying all around, and absolutely had the passion and loved airplanes. I’ve flown almost 100 different models of airplanes. I’m multi-engine seaplane-rated, helicopter-rated, jet-rated in the Citations. The Pilatus is the one I find myself in the most.”

He started his aviation business by flipping airplanes.

 “I’d just buy small airplanes—back then, like Cessna 310s and 414s. I had a Piper Saratoga, just fun little airplanes.” 

He did a TV show.

“I got a call from Discovery Channel of Canada, and they partnered with me on a TV show called ‘Dangerous Flights.’ It was about following the company’s aircraft sales, but more importantly, it featured the different ferry flights that I would do to deliver these aircraft all over the world. I was flying little Cessna 210s into Poland, Merlins to Australia, Caravans down to Africa. That was a really fun ride, and it also gave some the company a lot of notoriety and exposure which fueled the aircraft sales.

When he shifted the company from a brokerage to a brokerage plus fractional business.

 “It was about seven years ago so, about 2017-ish, when I had the idea for the fractional ownership model in the western United States. I had flown with a pilot who flew with one of the other fractional companies on the East Coast and just started really diving into that business model. I noticed that there was a really good opportunity for a mid-tier fractional company in the western U.S. So, we pivoted the company—we kept and continue to do aircraft sales to this day, but really put our attention into creating the fractional ownership, which included us buying charter certificate. In 2017, we put all our chips on the fractional side and luckily, it’s gone really well.”

His bootstrap mentality.

 “We haven’t taken any large private equity or venture capital money. Why I believe that's important is that you see a lot of companies in this industry that go raise a bunch of money and then they're gone in a couple years. We have a proven track record over the last 15 years, we're profitable, and we've been very fortunate, in the last three years, to have appeared on the Inc. 5000 list of the fastest-growing privately-held companies. We're growing fast but we're growing very intentionally—there are many other companies that try to be everything to everyone, but we've been focused on our fractional program for clients in the western U.S., and we hope to grow in 2026 and 2027 through acquisition, and spread our service throughout the region.”