Passive Income Pilots
Where Pilots Upgrade Their Money
Welcome to the Passive Income Pilots Podcast – the show designed to help pilots climb to new levels of financial success.
Join Tait Duryea & Ryan Gibson, both airline pilots, business owners and investors, as they interview top experts and share practical knowledge on real estate, tax strategy, passive income and generational wealth. This one-of-a-kind show created specifically for professional pilots offers applicable strategies and tactics for improving your financial life.
Whether you're a seasoned pilot or just starting out, we'll equip you with the expertise and confidence you need to upgrade your money and achieve true financial independence.
#143 - How High Cash Value Life Insurance Works for Pilots with Rod Zabriskie
Could life insurance be a better cash-flow tool than a savings account? Tait Duryea and Ryan Gibson sit down with Rod Zabriskie from Money Insights Group to break down how high cash value whole life insurance can be used as a powerful cash-flow tool for pilots and investors. They cut through the con...
#142 - Tax Planning for W-2 Pilots Without Complex Businesses with Gary Heldt
Are you paying for a high-powered CPA when your tax situation doesn’t actually require one? In this episode, Tait Duryea and Ryan Gibson sit down with CPA Gary Heldt to clarify what smart tax planning really looks like for high-income pilots with relatively simple financial lives. They break down ho...
#141 - How Pilots Can Use Business Structures to Reduce Taxes with Toby Mathis
Tait Duryea and Ryan Gibson sit down with Toby Mathis to unpack one of the most misunderstood topics for high-income pilots: business structure and taxes. They explain when to use sole proprietorships, LLCs, S-corps, and C-corps, how losses and profits flow to your personal return, and why entity ch...
#140 - From Goals to Execution: A Year-End Playbook
Tait Duryea and Ryan Gibson close out 2025 by pulling back the curtain on how high performers actually plan, execute, and stay intentional across money, business, and family life. From Spartan’s acquisition pace and Turbine’s investor roadmap to family board meetings, goal frameworks, and habit form...
#139 - How to Run Single-Family Rentals Like a REIT with Matthew Whitaker
What if managing rentals like an institution is the key to higher returns and less stress? Hosts Tait Duryea and Ryan Gibson talk with Matthew Whitaker, founder of Evernest, about scaling property management with systems, data, and AI. From HELOC-driven growth to managing 20,000 homes nationwide, th...