What happens when the systems that helped you grow start becoming the very thing holding you back?
Cory Bengtzen and Tommy Aoki have helped turn SkyShare from a small aviation brokerage into a fast-growing private jet company competing against some of the biggest names in the industry. But beneath the polished world of aircraft, owners, and luxury travel is a business entering a much harder stage of growth. As SkyShare pushes toward becoming a top 10 operator, Cory and Tommy face the pressure of limited systems, expensive talent, pilot retention, acquisition goals, AI disruption, capital needs, and a company that has outgrown the scrappy tools that got it here. You’ll hear how two lifelong friends are trying to preserve culture, simplify operations, align incentives, and build the discipline required to scale a high-stakes aviation business without losing what made it work in the first place.
Cory Bengtzen is the founder and CEO of SkyShare, a private aviation company offering aircraft management, charter, fractional ownership, and other aviation services. Tommy Aoki joined Cory to help lead the company through its next stage of growth, bringing decades of operational and leadership experience to the business. Together, they are working to scale SkyShare while preserving the culture and relationships that helped build it.
What you’ll learn in this episode:
00:01:48 — How Cory went from barely graduating high school to selling cars, building dealerships, and launching an aviation company with no roadmap
00:02:31 — How SkyShare grew from a simple aircraft brokerage into a full-service private aviation company spanning FBOs, fractional ownership, charter, aircraft management, and more
00:03:24 — Why a painful business split made Cory swear off partners, and why he eventually trusted Tommy to help scale SkyShare
00:04:06 — How Tommy’s dream of becoming a Fortune 500 CEO took him through wireless, GameStop, and major operational leadership before bringing him back to building a company with his lifelong friend
00:10:13 — How one blunt conversation with a potential customer forced SkyShare to rethink its values, culture, and leadership from the ground up
00:17:43 — Why Tommy believes broken culture can be rebuilt, but only when leaders stop treating values like slogans and start living them every day
00:22:24 — Why SkyShare abandoned its goal of being “most loved” to pursue a top 10 operator ranking by 2030, and what that ambition will demand
00:39:15 — How systems, AI, pilot retention, office space, and access to capital are now standing between SkyShare and its leap from regional player to national contender
Learn more about Cory Bengtzen, Tommy Aoki, and SkyShare:
https://www.skyshare.com/
Want to gain traction in your own company? As written about in the bestselling book Traction by Gino Wickman, the Entrepreneurial Operating System® (EOS®) helps entrepreneurial leadership teams clarify their vision, gain traction, and work together more effectively. Learn more:
https://www.eosworldwide.com/
Want a little more clarity in your week? Sign up for Mark O’Donnell’s Clarity Break Thoughts newsletter:
https://www.eosworldwide.com/claritybreakthoughts
Follow the show on your favorite platform:
http://lnk.to/hittingtheceiling
This episode was produced by Story On Media:
https://www.storyon.co/
