Passive Income Pilots

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 contract knowledge, and why passion matters when choosing a side hustle. If you’ve ever wondered how to turn extra time into oppo...

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 from unnecessary taxes, this episode offers practical frameworks to help pilots think long-term about their portfolio, income streams, and legacy planning.

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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 consistent cash flow can be a game-changer for high-income professionals looking to upgrade their money strategy.

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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 the IRS as a subject matter expert, including leading national audits focused on aircraft deductibility. She now co-owns...

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 single-family rentals to comm...

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 founder of Hall CPA, widely known as The Real Estate CPA. After working at Ernst & Young and PwC, he left the...

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 pilot use cases, common mistakes, and why this strategy has become a quiet cornerstone for soph...

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 coordinated advice can quietly compound into meaningful long-term gains. If you want clarity, confidence, and a more intentional approach to...

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 nationally recognized tax attorney, investor, and educator, best known for simplifying complex tax...

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 focused, intentional 2026. Do not just listen. Decide who you are becoming and move...

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 founder of Evernest, a nationwide property management platform serving over 20,000 rental homes across 50 markets. A former single-family investor who...

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 diligence, alignment, and saying no to bad opportunities.

Mat Sorensen is a nationally recognized authority on self-directed retirement investing...

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 how to secure your legacy and prevent costly mistakes, this episode is essential listening for pilots building serious wealth.

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, conservative underwriting, and Seattle’s shifting landscape, this epi...

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 earners. Discover how pilots can use this asset class to balance real estate, reduce taxable income, and ac...

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 three decades in clinical practice and a deep background in human factors, circadian rhythm, and sl...

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 which moves to make before December 31, and how to turn your taxes into one of your b...

What happens when a real estate investor decides to buy an airport? In this episode, host Tait and Ryan sit down with Robert DeLaurentis, the “Peace Pilot,” to unpack how he transformed a rundown airport into a thriving hub of aviation and community life. Robert shares how his decades in multifamily real estate funded his passion for flying, why legacy matters more than luxury, and how creative business models can make even airports profitable. From flying over both poles to battling bureaucracy, his story is a masterclass in purpose-driven investing, resilience, and vision.

Robert DeLa...

Where should you put your money right now? 

Ryan Gibson and Tait Duryea sit down with economist Dr. Elliot Eisenberg to decode the markets, interest rates, and the economic forces shaping your portfolio. From AI layoffs to multifamily real estate, they break down how high-income earners, especially pilots, can build wealth intelligently amid uncertainty. Elliot reveals why the top 10% of earners are keeping the economy afloat, what sectors look undervalued, and which indicators truly predict where we’re headed next. Packed with humor, clarity, and actionable advice, this episode helps you read the financial ski...

What does true diversification look like when you’re building wealth as a pilot? 

In this episode, Ryan Gibson sits down with his longtime colleague and friend, Ted Greene, to unpack how to define success with your spouse, avoid emotional investing, and create a portfolio that brings peace of mind. From surviving Wall Street lawsuits to building lasting wealth through real estate, Ted shares the hard-earned lessons behind his “NNN Principle”: Never, Never, Never invest by looking in the rearview mirror. Learn how to protect your assets, ladder your investments, and build a plan that la...

Why do so many high-earning pilots struggle to build real wealth?

Hosts Tait Duryea and Ryan Gibson get candid about the habits, mindset, and blind spots that keep aviators from achieving true financial independence. They reveal the five biggest mistakes pilots make, from lifestyle creep and tax traps to ego-driven investing, and how to replace them with smarter, more sustainable wealth strategies. Whether you’re a first officer just starting out or a captain eyeing retirement, this conversation will challenge how you think about money, success, and the long game of building lasting freedom.

What do private placement memorandums really mean for you as an investor? 

Hosts Tait Duryea and Ryan Gibson sit down with attorney and real estate operator Seth Bradley to pull back the curtain on syndication documents, accreditation rules, and what truly protects investors. Seth shares his personal journey from med school to big law to entrepreneurship, and why his legal background gives him a unique perspective on raising capital and building passive income. Discover why trust in the operator matters more than projections, what to look for in waterfalls and fee structures, and the r...

How protected is your wealth if something goes wrong? 

In this episode of Passive Income Pilots, Tait Duryea and Ryan Gibson sit down with asset protection expert Adam Kintigh to share practical strategies every pilot and high-income professional should know. From real estate privacy trusts that cut transfer taxes to Wyoming LLCs that safeguard syndications, Adam explains how to structure your assets the right way. You’ll learn why a clean tax return matters, how partnerships and S-Corps simplify filings, and why umbrella policies aren’t enough. If you’re growing wealth...

What separates pilots who want to invest from those who actually succeed? 

In this episode, Tait Duryea and Ryan Gibson share the real stories behind their first deals, the mistakes they made, and the lessons that still guide them today. From disastrous single-family rentals to managing multifamily properties, they explain why failure is often the best teacher and why no one should try to “lone wolf” their way through real estate.

They also highlight the power of networking and why being “in the arena” matters more than sitting on the sidel...

Can oil and gas really be a smart play for high-income professionals? In this episode, Tait Duryea and Ryan Gibson sit down with Mark Fleming, petroleum engineer and Turbine Capital’s oil & gas advisor, to break it down. From the basics of how drilling works to the tax advantages that can offset W2 income, you’ll learn the realities of this often-misunderstood industry. The conversation covers political risk, environmental concerns, portfolio allocation, and many more. Whether you’re curious about non-op partnerships, cashflow timing, or long-term energy trends, this episode gives you the insider perspective every pilot-investor needs.

Mark...

Tait Duryea and Ryan Gibson welcome Mat Sorensen, CEO of Directed IRA, for a powerful discussion on how pilots and high-income professionals can unlock private investment opportunities through retirement accounts. From self-directed IRAs to Solo Ks, Mat explains the mechanics of rolling over old 401(k)s, navigating recent regulatory changes, and tapping into lucrative private markets that were once out of reach. 

Mat Sorensen is the CEO of Directed IRA and Directed Trust Company, where he oversees thousands of self-directed retirement accounts including IRAs, Roth IRAs, HSAs, and Solo 401(k)s. He is also a...

Is now the right time to buy real estate or to hold cash? 

In this episode, Tait Duryea and Ryan Gibson sit down with Hunter Thompson, founder of Asym Capital and host of Cash Flow Connections, to unpack today’s real estate market. They cover cycles, debt structures, the COVID impact, rising interest rates, and why current distress is more about financing than fundamentals. Whether you’re an LP wondering how to vet a deal or a high-income professional looking for the next big move, this conversation offers clarity on where we stand in 2025 and w...

What if your life insurance could help you invest without selling a single asset?

Tait Duryea and Ryan Gibson welcome back Rod Zabriskie of Money Insights to demystify how whole life insurance can be used as a wealth-building tool. They break down the differences between term and whole life, how cash value grows, and why this strategy avoids risks like margin calls. You’ll hear how pilots are using these policies to fund real estate, reduce taxes, and create a perpetual source of investment capital.

Rod Zabriskie, president of th...

What if your first home turned into your first big win? 

Tait Duryea and Ryan Gibson welcome Brad Hilton and Aubrey Carlson, a powerhouse pilot couple who turned a VA loan into a cash-flowing real estate business. From renovating a dated beach house to designing destination-worthy cabins in Julian, CA, Brad and Aubrey break down how they scaled a short-term rental empire—without any formal training. Learn how they source properties, design for ROI, automate operations, and balance business with marriage. This episode is packed with real-world strategies, software hacks, and tax tips for pil...

What separates a solid real estate deal from a costly mistake? In this episode, hosts Tait Duryea and Ryan Gibson welcome Derrick Harris, SVP at Spartan Investment Group, to walk us through the real-world process of evaluating markets, properties, and operational risks. With a portfolio that spans millions of square feet, Derrick shares what works, what doesn’t, and what every investor should know, whether you're going passive or managing properties yourself. From feasibility studies and due diligence to team dynamics and tough lessons learned, this is your inside look at how pros protect investments and build real value.

What if your rental property is a lawsuit away from costing you everything? 

Tait Duryea connects with asset protection expert Adam Kintigh of Nevada Corporate Headquarters to break down what every investor should know about shielding wealth. From piercing the corporate veil to choosing between LLCs and real estate privacy trusts, this episode covers real risks, smarter structures, and how to avoid costly mistakes. 

Adam Kintigh is an asset protection strategist with over 24 years of experience, currently with Nevada Corporate Headquarters (NCH). He specializes in forming entities, estate planning, ta...

Get ready to demystify the 2025 Tax Bill.

Hosts Tait Duryea and Ryan Gibson sit down with Nathan Sosa, tax strategist at Hall CPA, to uncover what this sweeping legislation really means for pilots and high-income earners. From the return of 100% bonus depreciation to new deductions for auto loans and overtime, Nathan breaks down exactly who benefits and how. Whether you're building passive income or just want to keep more of what you earn, this is required listening.

Nathan Sosa is a Certified Public Accountant (CPA) with Hall CPA, a...

Ever wonder what happens when you invest in a syndication? In this episode, hosts Tait Duryea and Ryan Gibson break down how real estate syndications work, from deal sourcing and underwriting to legal docs, fees, and investor returns. Learn how passive investors get access to large-scale deals, what to look for in a sponsor, and what happens after you wire the funds. If you're considering a syndication, this is your essential primer.

Show notes:

(0:00) Intro

(03:11) Why syndications open new doors

(05:02) What is a real estate syndication?

(07:20...

What could cost you your flying career? Not being prepared for your medical. 

Hosts Tait Duryea and Ryan Gibson welcome back Dan Monlux of Wingman Med to discuss how pilots can protect their FAA medical certificates. Dan breaks down what happens during a medical exam, the importance of primary care, and why early detection matters. This is a must-listen for pilots over 40 and anyone serious about staying in the skies.

Dan Monlux is a retired Navy F-18 pilot and dual-trained physician in family and aerospace medicine. As co-founder of W...

Get ready to uncover the secrets of one of commercial real estate’s most resilient and misunderstood asset classes: self-storage. In this in-depth episode, Tait Duryea and Ryan Gibson explore why self-storage continues to outperform in uncertain times, how millennials are transforming storage use, and what makes it such a powerful wealth vehicle for passive investors. They share personal stories, break down tenant behavior, explain how to boost NOI with tenant insurance, and demystify cap rates and value creation. Plus, hear about their upcoming Houston tour where you can walk properties and learn the strategy firsthand.

In this episode, hosts Tait Duryea and Ryan Gibson sit down with attorney Amanda Wynalda from Anderson Advisors to unpack everything pilots and high-income earners need to know about trusts, wills, and asset protection. From revocable vs. irrevocable trusts to layering LLCs and avoiding the due-on-sale clause, this episode is a blueprint for protecting your wealth while staying legally compliant. 

Amanda Wynalda is a licensed attorney and executive at Anderson Business Advisors, where she leads the land trust and deed department. With a background in tax law, estate planning, and a personal history in a...

In this episode, hosts Tait Duryea and Ryan Gibson talk with chief economist Dr. Peter Linneman to demystify interest rates, the national deficit, and how it all affects pilots, real estate investors, and entrepreneurs. Discover why U.S. debt may not be the threat it’s made out to be, how capital flows drive values, and what most people get wrong about inflation and treasury yields. They also unpack commercial real estate's current cycle, the impact of bonus depreciation, and why now might be the smartest time to invest if you know where to look.

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In this episode, Tait Duryea and Ryan Gibson welcome CPA Thomas Castelli of Hall CPA to break down the latest tax developments affecting high-income earners. From the potential return of 100% bonus depreciation to how the real estate professional status works in practice, Tom shares key strategies to help you keep more of what you earn. Whether you're flying the line or growing your rental portfolio, this episode delivers practical advice for optimizing deductions, structuring entities, and deciding when to hire a pro vs. going DIY.

Thomas Castelli is a CPA and partner at Hall...

Get ready to fast-track your financial freedom. In this power-packed solo episode, Tait Duryea and Ryan Gibson share the top strategies from over 110 episodes of Passive Income Pilots. From unlocking hidden cash in your 401(k) and home equity to leveraging life insurance and short-term rentals for major tax breaks, they distill years of pilot-specific investing wisdom into five key pillars. You’ll learn about real estate professional status, cost segregation, bonus depreciation, syndications, and which CPA you need. Whether you’re just starting or optimizing your path to passive income, this episode is your blueprint.

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In this episode, hosts Tait Duryea and Ryan Gibson welcome Ramez Fakhoury from IRA Club. This episode dives into how pilots can unlock old 401(k)s, TSPs, and HSAs for real estate and other alternative investments. Hear a detailed story of a Southwest pilot transitioning to American Airlines and learn what decisions made the biggest impact. Whether you're changing airlines or just seeking better returns, this episode is packed with actionable insights.

Ramez Fakhoury is the Vice President of IRA Club, a leading self-directed IRA custodian. With a background in hospitality and entrepreneurship, Ramez...