Passive Income Pilots
Tait Duryea and Ryan Gibson
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About This Podcast
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.
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Recent Episodes
#156 - From Active Deals to Passive Income with Chris Prefontaine
Tait Duryea and Ryan Gibson welcome back Chris Prefontaine for a practical conversation on active investing, creative deal structures, and using real estate to build capital for future passive…
#155 - The New Reality of Aviation Hiring with Nik Fialka
What happens when the aviation job market shifts faster than pilots are prepared for?Live from TPNX in Dallas, Tait Duryea sits down with Nik Fialka for a timely look at pilot hiring, airline…
#154 - The Pilot’s Guide to SDIRA Tax Traps with Mark Kohler
Tait Duryea and Ryan Gibson welcome back Mark Kohler to unpack one of the most misunderstood topics in self-directed IRA investing: UBIT and UDFI. Mark explains how these taxes show up in real estate…
#153 - Tax Moves Every Pilot Should Know with Nathan Sosa
How much money are you leaving on the table by waiting until tax season to start planning?Hosts Tait Duryea and Ryan Gibson talk with Nathan Sosa from Hall CPA to break down the latest tax updates…
#152 - Free Estate Planning and a Hidden Tax Strategy with Jenny Spradling
Tait Duryea and Ryan Gibson sit down with Jenny Spradling, co-founder of FreeWill, to explore how estate planning can be simpler, faster, and even free. Jenny explains why millions of Americans still…
#151 - Debt, AI, and the Next Market Cycle with Guy Adami
What happens when record debt, rising interest rates, and AI disruption collide in the global economy?Hosts Tait Duryea and Ryan Gibson welcome back market veteran Guy Adami to unpack the forces…
#150 - From Listener to Investor with John Wahrmund
Hosts Tait Duryea and Ryan Gibson sit down with First Officer at Southwest Airlines pilot John Wahrmund to unpack how one listener turned podcast advice into real results. John shares how episode 10…
#149 - Side Hustles Every Pilot Should Consider
Hosts Tait Duryea and Ryan Gibson explore one of the most common questions among airline pilots: Should you start a side hustle? Drawing from Ryan’s early experience building income streams during…
#148 - Traditional Vs. Roth IRAs: What Pilots Need to Know
Tait Duryea and Ryan Gibson break down one of the most important retirement decisions pilots face: Traditional vs. Roth IRAs. They explain how taxes impact withdrawals, why required minimum…
#147 - From Cap Rates to Cash Flow: Strategic Moves for 2026
Tait Duryea and Ryan Gibson sit down for a special hosts-only episode to break down where they see the biggest opportunities for 2026. From reshoring trends fueling industrial growth to the…
#146 - Aircraft Tax Write-Offs Explained by a Former IRS Auditor, Victoria Boon
Hosts Tait Duryea and Ryan Gibson welcome former IRS auditor Victoria Boon to cut through the noise around aircraft tax deductions. Learn how bonus depreciation really works, why aircraft are treated…
#145 - Bonus Depreciation & Cost Seg: The Tax Strategy Pilots Can’t Ignore with Gian Pazzia
What if the IRS already allows you to write off far more of your real estate, but no one ever showed you how?In today’s episode, Tait Duryae sits down with Gian Pazzia to break down cost segregation…
#144 - Depreciation, Cost Segs, and the IRS Rules Pilots Miss with Brandon Hall
Tait Duryea is joined by Brandon Hall to break down one of the most misunderstood tools in real estate investing: depreciation. From straight-line depreciation to cost segregation and 100 percent…
#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…
#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…
#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…
#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…
#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…
#138 - How to Vet Deals, Operators, and Advisors the Right Way with Mat Sorensen
Tait Duryea and Ryan Gibson sit down with Mat Sorensen of Directed IRA to tackle one of the most common investor questions: Who do you actually trust when investing in alternative assets? The…
#137 - Revocable Vs. Irrevocable Trusts: What Pilots Must Know with Adam Kintigh
Clarity and control for the wealth you’re building. Tait Duryea and Ryan Gibson sit down with asset protection expert Adam Kintigh for his third appearance to break down one of the most misunderstood…
Frequently Asked Questions
Passive Income Pilots has published 155 episodes since March 2023, covering topics in Business, Careers.
Passive Income Pilots is currently moderate with new episodes weekly. Average episode length is 48m.
Sign up on Grep.FM to access contact details for Passive Income Pilots, including email and social media links.
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