Passive Income Pilots

#167 - From Wall Street to Infinite Banking with Chris Naugle

Join us on October 8–9, 2026, in Las Vegas, Nevada for the first-ever Passive Income Pilots Conference. Learn how to build smarter wealth beyond the cockpit: https://www.

#166 - Fly-Inn Rentals for Pilots and Investors with Carollyne Carmichel & Kenya Hodson

Join us on October 8–9, 2026, in Las Vegas, Nevada for the first-ever Passive Income Pilots Conference. Learn how to build smarter wealth beyond the cockpit: https://www.

#165 - Flight Decks, Financial Freedom, and the Pilot Community with Dylan and Max of 21.Five

Join us on October 8–9, 2026, in Las Vegas, Nevada for the first-ever Passive Income Pilots Conference. Learn how to build smarter wealth beyond the cockpit: https://www.

#164 - LLCs, Trusts, and Asset Protection for Pilots with Adam Kintigh

Join us on October 8–9, 2026, at the M Resort and Casino in Las Vegas for the first-ever Passive Income Pilots Conference. Learn how to build smarter wealth beyond the co

#163 - From Pilot Spouse to Café Owner with Brenda Gage

Join us on October 8–9, 2026, at the M Resort and Casino in Las Vegas for the first-ever Passive Income Pilots Conference. Learn how to build smarter wealth beyond the co

#162 - The 2026 Airline Pilot Career Outlook with Kit Darby

Watch this episode on YouTube to see the screen share: https://youtu.be/GjCnHgscdms Join us on October 8–9, 2026, at the M Resort and Casino in Las Vegas for the first-

#161 - Aircraft Ownership, Insurance, and Liability with Scott Williams

Buying an airplane can create opportunities and legal exposure that pilots may not see until something goes wrong. Tait Duryea and Ryan Gibson sit down with aviation atto

#160 - Insurance Strategies for High-Income Professionals with Rod Zabriskie

Insurance may not feel exciting until it becomes the thing protecting everything you’ve built. In this episode, Tait Duryea and Ryan Gibson sit down with Rod Zabriskie to

#159 - How Deferred Sales Trusts Work with Trevor Kuresa

Tait Duryea and Ryan Gibson sit down with Trevor Kuresa to unpack the Deferred Sales Trust, a lesser-known strategy for deferring capital gains after selling a business o

#158 - Why the 10-30-30-30 Strategy Could Change How Pilots Invest

Is your wealth strategy working together or pulling in different directions? Hosts Tait Duryea and Ryan Gibson unpack the 10-30-30-30 strategy for balancing cash, 401(k)s

#157 - Who Gets Paid First? How Real Estate Deals Are Actually Structured

Tait Duryea and Ryan Gibson break down one of the most important but often misunderstood parts of real estate investing: the capital stack. They explain how senior debt,

#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 capi

#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 a

#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

#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

#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 wh

#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

#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

#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 buil

#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, w