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PODCAST

Passive Income Pilots

Tait Duryea and Ryan Gibson

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

business investing

All Episodes

48:03

#152 - Free Estate Planning and a Hidden Tax Strategy...

Passive Income Pilots ·

2026/04/07

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 lack basic estate documents and how that creates major complications for families. The conversation breaks down probate, wills vs. trusts, and why both are often needed. They also uncover powerful strategies around charitable giving, including how donating appreciated assets like stock or crypto can

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48:36

#151 - Debt, AI, and the Next Market Cycle with Guy...

Passive Income Pilots ·

2026/04/02

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 shaping today’s financial markets. From bond yields and inflation to the Buffett Indicator and AI’s impact on jobs, Guy offers a behind-the-scenes look at what professional investors are watching right now. The conversation explores why the market feels strong even while many stocks are down sharply, how

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40:48

#150 - From Listener to Investor with John Wahrmund

Passive Income Pilots ·

2026/03/27

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 pushed him to buy a short-term rental in Galveston, unlock major tax savings, and rethink how his family builds wealth. This episode highlights intentional investing, knowing your market, using the right team, and why tax strategy can be a powerful tool for high-income professionals who want more

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34:24

#149 - Side Hustles Every Pilot Should Consider

Passive Income Pilots ·

2026/03/11

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 layovers, the hosts share practical ideas pilots can pursue both inside and outside aviation. From consulting and drone photography to aircraft brokerage and real estate investing, they explain how extra income can become the fuel for long-term wealth building. They also discuss tax strategy, airline

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45:50

#148 - Traditional Vs. Roth IRAs: What Pilots Need to...

Passive Income Pilots ·

2026/03/05

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 distributions matter, and how poor planning could leave your kids with a massive tax bill. The conversation also explores advanced strategies like Roth conversions, self-directed IRAs, and “Roth chunking” during low-income years. If you want to build wealth through real estate while protecting your retirement

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35:40

#147 - From Cap Rates to Cash Flow: Strategic Moves...

Passive Income Pilots ·

2026/02/17

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 demographic wave driving senior living demand, they unpack the macro forces shaping real estate right now. They also explain why falling interest rates, reduced new construction, and renewed capital flows are creating a unique window for investors. Plus, they dive into debt funds, tax considerations, and why

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54:00

#146 - Aircraft Tax Write-Offs Explained by a Former...

Passive Income Pilots ·

2026/02/09

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 differently from real estate, and what the IRS actually looks for during an audit. From Delta bonus taxation to leasebacks, qualified business use, and depreciation recapture, this episode is essential listening for pilots considering aircraft ownership as a tax strategy.Victoria Boon spent 22 years at

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39:18

#145 - Bonus Depreciation & Cost Seg: The Tax...

Passive Income Pilots ·

2026/02/04

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 in plain English and explain why it remains one of the most powerful tax strategies for real estate investors. Building on last week’s depreciation primer with Hall CPA, this episode covers how cost segregation works, when it makes sense, audit risk myths, and how pilots can apply it to everything from

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1:00:13

#144 - Depreciation, Cost Segs, and the IRS Rules...

Passive Income Pilots ·

2026/01/27

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 bonus depreciation, this episode explains how so-called “phantom losses” can legally reduce or even eliminate taxable income for pilots and other high earners. They also cover depreciation recapture, common investor mistakes, and why experienced investors think in decades, not tax years.Brandon Hall is the

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39:39

#143 - How High Cash Value Life Insurance Works for...

Passive Income Pilots ·

2026/01/20

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 confusion around “infinite banking” and explain how properly structured policies can improve liquidity, reduce friction when investing, and add meaningful long-term returns. This episode walks through real

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44:05

#142 - Tax Planning for W-2 Pilots Without Complex...

Passive Income Pilots ·

2026/01/13

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 how W-2 earners can optimize taxes without complex businesses, aggressive strategies, or unnecessary fees. Gary explains how often-overlooked fundamentals like benefits planning, estimated taxes, and

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56:21

#141 - How Pilots Can Use Business Structures to...

Passive Income Pilots ·

2026/01/06

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 choice impacts audit risk and mortgage eligibility. This episode is a practical roadmap for pilots starting side hustles who want to lower taxes, protect assets, and avoid costly mistakes.Toby Mathis is a

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23:44

#140 - From Goals to Execution: A Year-End Playbook

Passive Income Pilots ·

2025/12/30

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 formation, this episode offers a grounded look at what it takes to build momentum year after year. If you want clarity instead of drift and action instead of resolutions, this conversation sets the tone for a

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47:33

#139 - How to Run Single-Family Rentals Like a REIT...

Passive Income Pilots ·

2025/12/24

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, this conversation breaks down why professional operations, fraud prevention, and institutional discipline can transform single-family and small multifamily investing for pilots.Matthew Whitaker is the

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52:04

#138 - How to Vet Deals, Operators, and Advisors the...

Passive Income Pilots ·

2025/12/17

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 conversation breaks down how to vet operators, assess risk, understand leverage, and use self-directed retirement accounts responsibly. Mat shares real-world insight from seeing thousands of deals flow through his firm, explains why advisors often avoid alternatives, and outlines practical rules for due

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56:01

#137 - Revocable Vs. Irrevocable Trusts: What Pilots...

Passive Income Pilots ·

2025/12/09

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 pieces of a pilot’s financial plan: the revocable living trust. Discover how to structure your trust, avoid probate disasters, protect your heirs from creditors, ensure your wealth goes where you intend, and understand the real difference between revocable and irrevocable trusts. If you've ever wondered

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41:30

#136 - What HGTV Won’t Tell You About Flipping Houses...

Passive Income Pilots ·

2025/12/02

Are you using the exit strategies that actually work in this market?Hosts Tait Duryea and Ryan Gibson talk with seasoned investor and author Leka Devatha to pull back the curtain on what’s real and what’s not in flipping, reality TV, and today’s housing market. Get ready to uncover the truth behind her Amazon Prime episode, learn the creative strategies inside her new book Return on Real Estate, and discover how investors can win even when the market slows. From mid-term rentals to ADUs,

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52:50

#135 - The Truth About Oil and Gas Investing with Tim...

Passive Income Pilots ·

2025/11/26

Are you unknowingly passing up five-figure tax savings available right now?Tait Duryea and Ryan Gibson sit down with oil and gas expert Tim Pawul to reveal why minerals, royalties, and non-operated working interests have become one of the most powerful tools for cash flow and tax strategy. Get ready to understand the real reason hydrocarbons aren’t going anywhere, how minerals function like “underground real estate,” and why non-op wells offer significant first-year tax advantages for high-income

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49:53

#134 - Fatigue, Flight Deck Safety, and the Science...

Passive Income Pilots ·

2025/11/18

Sleep becomes exciting, especially when it’s with Dr. Adam Shapiro. Tait Duryea and Ryan Gibson sit down with this board-certified sleep specialist and ATP pilot to uncover what every aviator needs to know to protect their health and their medical. Get ready for practical guidance on staying sharp, staying healthy, and staying in the cockpit longer.Dr. Adam Shapiro is a board-certified sleep medicine specialist, ENT surgeon, senior FAA Aviation Medical Examiner, and ATP-rated pilot. With more than

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52:37

#133 - Year-End Tax Moves Pilots Can’t Miss with Toby...

Passive Income Pilots ·

2025/11/12

Taxes become more exciting, especially when it’s with Toby Mathis. Tait Duryea and Ryan Gibson welcome back tax strategist and investor Toby Mathis for another powerhouse session on how to keep more of your money before year-end. From bonus depreciation and the short-term rental loophole to smarter charitable giving and donor-advised funds, Toby reveals how high-income earners can legally slash their tax bills. Whether you’re a pilot, business owner, or passive investor, you’ll walk away knowing

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153 results

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