CJI Podcast #34 | Jason Middleton | Silver Air Private Jets | "You've got to live, breathe and bleed it"

In this episode, we are joined by Jason Middleton, CEO and founder of Silver Air Private Jets. A former elite triathlete turned pilot, Middleton brings an "all-in" mentality to aviation. He shares how Silver Air survived the 2008 financial crisis through relentless focus, and why he prioritises specialisation over vertical integration.Middleton is a vocal critic of unregulated charter brokers, advocating for operator-level safety standards. He launched Flight Club to give clients transparency and control, a move driving over $100m in annual revenue. During Covid, he kept all staff on payroll, reinforcing his people-first culture. Middleton also emphasises stepping away from the office – whether surfing or hunting – to solve problems creatively.The conversation touches on leadership lessons, regulatory challenges, global operational risks, the importance of staying connected to the flight deck as a hands-on CEO and much more besides.