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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

1:00:00

#120 - How to Evaluate Markets, Properties, and Risks...

Passive Income Pilots ·

2025/07/29

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

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53:43

#119 - LLCs, Trusts, and Bulletproof Asset Protection...

Passive Income Pilots ·

2025/07/17

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,

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48:38

#118 - The Big Beautiful Tax Bill with Nathan Sosa

Passive Income Pilots ·

2025/07/11

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

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43:12

#117 - How to Evaluate and Join Real Estate Syndications

Passive Income Pilots ·

2025/07/02

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

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55:19

#116 - Medical Checkride: Medical Myths, Truths, and...

Passive Income Pilots ·

2025/06/24

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

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50:47

#115 - Inside Self-Storage: A Hidden Powerhouse for...

Passive Income Pilots ·

2025/06/17

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

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59:50

#114 - Trusts, Taxes & Transfers: What Every Investor...

Passive Income Pilots ·

2025/06/10

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

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53:42

#113 - The Fed, The Treasury, and Your Portfolio with...

Passive Income Pilots ·

2025/06/03

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

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47:15

#112 - The Tax Strategies Every Pilot Should Know in...

Passive Income Pilots ·

2025/05/27

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

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44:56

#111 - Five Investing Strategies for High-Earning Pilots

Passive Income Pilots ·

2025/05/22

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

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54:06

#110 - The IRA Club Advantage: The Self-Directed IRA...

Passive Income Pilots ·

2025/05/13

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,

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39:19

#109 - The Flight Plan for Syndications: Risk,...

Passive Income Pilots ·

2025/05/06

In this episode, hosts Tait Duryea and Ryan Gibson deliver an in-depth, pilot-friendly primer on syndications and passive real estate investing. They break down the risk spectrum from core to opportunistic deals, while sharing real-world analogies and experiences from their own projects, like the Canyon City land entitlement.Learn how to properly evaluate risk-adjusted returns, the importance of DSCR vs LTV, and what preferred return really means in a syndication waterfall. This episode is a

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21:04

#108 - Case Study: Real Estate Professional Status...

Passive Income Pilots ·

2025/04/30

In this episode, Tait Duryea flies solo to spotlight a powerful tax strategy many high-income earners overlook: real estate professional status. Featuring Brandon Hall from Hall CPA, this episode breaks down a real tax court victory by a harbor pilot who leveraged a flexible W-2 job schedule to claim REP status and unlock massive tax savings. Discover the legal requirements, the importance of documentation, and how pilots are uniquely positioned to take advantage of this IRS loophole—a must-listen

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38:43

#107 - Take Control of Your Capital: Infinite Banking...

Passive Income Pilots ·

2025/04/22

Host Tait Duryea sits down with Brent Kesler, a seasoned life insurance strategist, to explore how pilots and high-income earners can build wealth by turning whole life insurance into a personal banking system. Brent breaks down the misunderstood "infinite banking" concept and how it can be used for real estate, debt payoff, or high-return lending—all while keeping control of your capital.Brent Kesler is a former chiropractor turned financial educator specializing in life insurance strategies. After

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39:31

#106 – Time Freedom and Cash Strategies with Brian...

Passive Income Pilots ·

2025/04/15

Hosts Tait Duryea and Ryan Gibson welcome financial strategist Brian Herriot for a thought-provoking conversation on redefining retirement and wealth. Explore the power of time freedom, why cash might be your most underappreciated asset, and how to build passive income streams that work for pilots and professionals alike. Brian shares practical tactics for holding liquidity, investing for lifestyle flexibility, and balancing entrepreneurship with financial security. Discover a fresh framework for

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46:05

#105 - Buying and Building a Profitable Aviation...

Passive Income Pilots ·

2025/04/08

In this episode, Tait Duryea and Ryan Gibson are joined by James Spearman, owner of Spearman Aircraft and Iconic Rides. James walks through his journey of acquiring and scaling an aircraft maintenance business through seller financing, boosting its value through streamlined systems and strategic marketing. He shares the mindset and steps that helped him turn a struggling shop into a seven-figure operation while positioning it for future passive income or a high-multiple exit. If you've ever

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49:01

#104 - Active vs. Passive: Storage Strategies from...

Passive Income Pilots ·

2025/04/01

In this episode, Tait Duryea and Ryan Gibson sit down with Michael Meylor, a seasoned pilot and self-storage investor who has built an impressive portfolio without raising outside capital. Michael shares how he transitioned from military to commercial flying, how he and his wife started investing in single-family rentals, and why they pivoted to commercial self-storage. The episode covers everything from identifying the right-sized deals to financing with SBA loans, and even touches on family

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45:35

#103 - Multifamily Mastery: Building Cashflow and...

Passive Income Pilots ·

2025/03/25

In this episode, Tait Duryea welcomes Gino Barbaro of Jake & Gino to unpack the mindset and mechanics behind building lasting wealth through multifamily real estate. Gino shares his journey from running a family restaurant to becoming a real estate investor with over 1,800 units. They explore topics like values-based decision-making, creating "happy money," the strategic use of whole life insurance for real estate investing, and how to teach financial stewardship to the next generation. This

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49:39

#102 - Creating True Passive Income Through Note...

Passive Income Pilots ·

2025/03/18

In this episode, Tait Duryea and Ryan Gibson sit down with retired airline captain and seasoned investor Tom Force to discuss a real estate strategy many overlook—note investing. They cover tax strategies, risk management, and how to get started in note investing. If you’re tired of tenant headaches and want to invest like a bank, this episode is for you.Tom Force, a retired airline pilot and real estate investor, found financial freedom through note investing. After years in rentals and

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41:21

#101 - Airbnb for Aircraft: Hangar Investing &...

Passive Income Pilots ·

2025/03/11

Hangar space is in short supply, but Trenton Ray is changing that. In this episode, Tait Duryea and Ryan Gibson chat with Trenton about Hangar Direct, his platform that’s like Airbnb for hangars—making it easier for pilots to find and rent space. They dive into the supply shortage, investment potential, and what to know about leasing, financing, or building a hangar.Trenton Ray is a corporate pilot and aviation entrepreneur based in Austin, Texas. With experience flying various private and corporate

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141 results

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