What does it really take to move from turning wrenches on helicopters to closing high-stakes aviation deals? We sit down with Joe, a former Army maintainer and crew member, to unpack the gritty, unfiltered path from technical mastery to building a business in a safety-first industry. The story starts on the flight line, where meticulous maintenance and responsibility for lives in the air forged a mindset that later shaped his entire sales approach.

Joe shares how he discovered that being great at the craft is only a small slice of entrepreneurship. Quitting multiple jobs after a few big wins seemed like the right move—until three months passed with no calls. That drought became a lesson in pipeline, positioning, and patience. We walk through the real work behind a sustainable aviation business: marketing that educates, sales that protects safety and profit, accounting basics, insurance, branding, and the crucial habit of consistent follow-up. If you’re eyeing aviation without a pilot license or A&P, you’ll learn how to add value by building trust, asking better questions, and partnering with maintenance and operations teams who keep aircraft flying safely.

We also dive into coaching and community. Joe invested in mentorships and observed top performers across industries, borrowing tactics without losing his voice. Success leaves clues—habits, systems, and standards you can adapt to aviation’s tight-knit ecosystem. And for veterans leaving the service, we highlight resources to rebuild your network and find your footing in business aviation. The big takeaway: if you become truly good at sales, you’ll always have a job, but in aviation the bar is higher—because every deal touches safety.

If this conversation sparks your next move, subscribe, share with a friend who needs it, and leave a review with your biggest takeaway. Your feedback helps more people find their runway.

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Aviation insurance provides a unique entry point into private aviation sales, offering both rewarding career opportunities and essential services to ultra-high-net-worth aircraft owners. Samantha Money shares her journey from traditional insurance into aviation specialization, revealing the skills, mindset, and approaches needed to succeed in this niche.

• Starting in insurance for ultra-high-net-worth individuals' estates before specializing in aviation
• Learning the industry through podcasts, YouTube videos, and networking with industry professionals
• Handling memorable deals, including insuring a baseball Hall of Famer's Challenger jet
• Securing broad pilot warranties despite carrier restrictions through creative negotiation
• Working with diverse clients from private buyers to complex corporate flight departments
• Making six figures possible within the first years through commission structures
• Building a book of business that generates ongoing revenue through renewals
• Requiring property and casualty licensing but minimal experience to enter the field
• Building professional relationships takes time but delivers long-term rewards
• Pursuing continuous education through organizations like the Aviation Insurance Association

If you want to learn more about aviation insurance, connect with Samantha Money on LinkedIn, where she regularly posts thought-provoking content about the industry.

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