Controlling Catastrophe: Why Captive Insurance Makes Sense w/ John C. Averill and Andy Shuttleworth

Most operators think insurance is about protection. Buy a policy, transfer the risk, move on. But what if that model is quietly draining your margins instead of protecting them? Because here’s the reality: in aviation, it’s not the catastrophic losses that kill your business; it’s everything else.  The unexpected maintenance event that isn’t covered. The operational hiccups you don’t want to claim. The hangar rash that never makes it to a claim, and you just absorb it. The constant, low-level financial hits that feel too small to insure but too frequent to ignore. Over time, it’s death by a thousand cuts, and traditional insurance was never built to solve that. What’s starting to emerge instead is a different mindset: stop thinking of insurance purely as a cost center, and start treating it as a financial strategy. Not to replace the traditional market, but to take back control of everything it leaves behind.  Because when you structure it right, the same dollars you’re used to losing can actually compound back into your business, building reserves, improving margins, and turning risk management into a profit lever instead of a drain. That’s exactly what captive insurance allows operators to do: take control of the risks traditional aviation insurance won’t cover and structure them in a way that actually works for the business. John C. Averill and Andy Shuttleworth are two experts working at the intersection of aviation risk and captive insurance.  In this episode, we talk about how operators can formalize self-insurance, why most people misunderstand what captives actually are, and how some businesses are quietly using them to retain profits, smooth volatility, and build long-term financial resilience.   You’ll also learn; Why the real financial pressure in aviation doesn’t come from where most operators think What actually sits outside traditional aviation insurance and why it matters more than it seems The shift from transferring risk to structuring it How some operators are starting to take control of costs they’ve always absorbed Why certain risks never make it into a policy and what can be done about them The difference between reacting to losses and designing for them Why the most sophisticated companies approach insurance very differently What changes when risk starts to show up on your balance sheet instead of someone else’s How to think about control, claims, and costs in a completely different way Why this isn’t a short-term fix, and what happens if you commit to it Where this approach extends beyond aviation into broader operational risk The biggest misconception about captives and why most people misunderstand them   About the Guests  John C. Averill is a Senior Vice President and risk advisor specializing in aviation, aerospace, and defense. His work sits at the intersection of operational risk, insurance, and legal frameworks, allowing him to design highly tailored solutions for complex exposures that traditional brokerage models often miss. With additional expertise in professional liability and environmental underwriting, John brings a broader, more integrated lens to risk, helping operators structure programs that go beyond standard coverage. He is part of a senior-level team with over 100 years of combined experience in insurance and risk management, including more than 50 years focused specifically on aerospace. Connect with John on LinkedIn.  Andy Shuttleworth is a Risk Management and Regulatory Compliance Consultant and the founder of Core Resilience LLC. With over 35 years of experience across federal and state agencies, he brings a deeply practical understanding of how risk, compliance, and operations intersect. Andy works with businesses to assess and strengthen their regulatory compliance, threat mitigation, and risk management strategies, offering an independent, unbiased perspective on where systems break down and how to improve them. His focus is on helping organizations protect not just their assets, but their long-term operational resilience and reputation. Connect with Andy on LinkedIn.  About Your Host Craig Picken is an Executive Recruiter, writer, speaker, and ICF Trained Executive Coach. He is focused on recruiting senior-level leadership, sales, and operations executives in the aviation and aerospace industry. His clients include premier OEMs, aircraft operators, leasing/financial organizations, and Maintenance/Repair/Overhaul (MRO) providers, and since 2008, he has personally concluded more than 400 executive-level searches in a variety of disciplines. Craig is the ONLY industry executive recruiter who has professionally flown airplanes, sold airplanes, and successfully run a P&L in the aviation industry. His professional career started with a passion for airplanes. After eight years’ experience as a decorated Naval Flight Officer – with more than 100 combat missions, 2,000 hours of flight time, and 325 aircraft carrier landings – Craig sought challenges in business aviation, where he spent more than 7 years in sales with both Gulfstream Aircraft and Bombardier Business Aircraft. Craig is also a sought-after industry speaker who has presented at Corporate Jet Investor, International Aviation Women’s Association, and SOCAL Aviation Association.    For more aerospace industry news & commentary: https://craigpicken.com/insights/.  To learn more about Craig Picken, visit https://craigpicken.com/.