Ep.256: Alex (@aebridgeman) is joined by Cory Bengtzen (@Cory-Bengtzen).

In this episode, I sit down with Cory Bengtzen, founder and CEO of SkyShare, to explore his entrepreneurial journey from the auto industry to building a vertically integrated private aviation business. Cory shares how his passion for aviation inspired him to leave the car business and start an airplane brokerage with no prior industry experience. He recounts his early days of cold-calling aircraft owners, developing a fractional ownership program, and growing SkyShare into a successful operation serving the Western U.S.

We dive into the unique challenges and opportunities in private aviation, from running Fixed Base Operators (FBOs) to launching fractional ownership and charter services. Cory explains how vertical integration—owning maintenance operations, FBOs, and a charter fleet—has been key to SkyShare’s resilience and growth. He also breaks down the economics of private aviation, describing how his team balances efficiency and service to deliver value for clients.

Cory also shares fascinating stories from his career, including ferrying aircraft across continents for the Discovery Channel’s Dangerous Flights and his insights into why so many aviation ventures fail. Whether you're an aviation enthusiast or a business owner considering private aviation, this episode is full of practical advice and compelling stories from one of the industry's most innovative leaders.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn.

Learn more about Alex and Think Like an Owner at https://tlaopodcast.com/

Links:

SkyShare - https://www.skyshare.com/

Cory on LinkedIn - https://www.linkedin.com/in/cory-bengtzen-95a13216/

Topics:

(00:00:00) - Intro

(00:01:10) - Building SkyShare

(00:12:35) - The economics of an FBO

(00:15:25) - The rationale for flying private

(00:23:50) - Customer journeys

(00:30:00) - Aircraft management from a customer standpoint

(00:32:04) - How are owners implementing modifications to jets?

(00:36:45) - Changes in ICP across programs

(00:38:58) - What goes wrong the most in private aviation?

Taomo Zhou, “Migration in the Time of Revolution: China, Indonesia and the Cold War” (Cornell UP, 2019)