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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

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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51:12

#100 - Getting to Know Tait & Ryan

Passive Income Pilots ·

2025/03/04

In this special 100th episode of Passive Income Pilots, Tait Duryea and Ryan Gibson take listeners behind the scenes of the podcast, sharing how it all started and what goes into creating each episode. They also dive into their personal journeys in aviation, investing, and entrepreneurship. From buying their first rental properties to scaling multi-million-dollar real estate portfolios, they discuss lessons learned, investment strategies, and what’s next for the market. Plus, they break down key

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52:24

#99 - Turnkey Real Estate: Passive or Problematic? A...

Passive Income Pilots ·

2025/02/25

In this episode, Tait Duryea and Ryan Gibson connect with Zach Lemaster to explore the world of turnkey real estate and build-to-rent properties. They discuss the benefits and challenges of owning physical real estate, the tax advantages of rental properties, and how busy professionals can invest without becoming full-time landlords. Zach shares insights on market trends, the importance of expectation setting, and why new construction rentals might be a better option than traditional rehabs.Zach

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49:46

#98 - The Right Coverage: Property Insurance...

Passive Income Pilots ·

2025/02/18

In this episode of Passive Income Pilots, Tait Duryea and Ryan Gibson sit down with Valerie Cusano, an insurance expert with a background in law and decades of experience in commercial and residential insurance. Val dives deep into the critical aspects of real estate insurance, particularly for condo and rental property owners. She explains the difference between condo and homeowners insurance, key policy coverages investors should have, and how to evaluate a building’s financial health before

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53:27

#97 - Creative Deal Structuring: Smart Real Estate...

Passive Income Pilots ·

2025/02/11

In this episode, Tait Duryea and Ryan Gibson dive into creative real estate financing with Chris Prefontaine, founder of Smart Real Estate Coach. Chris shares powerful strategies like seller financing, subject-to deals, and lease purchases, revealing how investors can acquire properties without banks—even in today’s high-interest rate environment. Learn how to find off-market properties, negotiate seller carrybacks, and unlock hidden real estate opportunities.Chris Prefontaine is the chairman and

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49:44

#96 - Airplane Write-Offs, IRS Audits, and Smart Tax...

Passive Income Pilots ·

2025/02/04

Have you ever wondered how you could write off an airplane? In this episode, Ryan DeMoor joins hosts Tait Duryea and Ryan Gibson to break down the tax benefits of aircraft ownership. Ryan shares how pilots and business owners can strategically use aircraft purchases for tax deductions, the IRS rules around business use, and why proper record-keeping is critical for audits. Whether you're considering buying a Cessna or a Gulfstream, this episode is packed with insights on bonus depreciation, IRS

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53:31

#95 - Franchise Investing 101: Insights and...

Passive Income Pilots ·

2025/01/28

In this episode of Passive Income Pilots, hosts Tait Duryea and Ryan Gibson explore the world of franchise ownership with franchise expert Cliff Nonnenmacher. Cliff brings decades of experience as a franchise consultant and serial entrepreneur, sharing insights into how pilots and professionals can invest in or operate franchises to build wealth. The discussion covers everything from initial franchise fees to evaluating opportunities, scaling businesses, and emerging non-brick-and-mortar trends

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47:51

#94 - Fail Fast, Succeed Faster: Wealth-Building and...

Passive Income Pilots ·

2025/01/21

In this episode, Tait Duryea and Ryan Gibson sit down with Christian Schiller, an accomplished investment banker with a wealth of experience buying, selling, and evaluating businesses. Christian shares his investment journey, including lessons from early failures, how he refined his investment strategy, and why knowing your limits is key to success. He breaks down the role of investment bankers, explains how pilots and high-income professionals can benefit from understanding private equity and

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55:19

#93 - Stock Market Insights and Tax Strategies for...

Passive Income Pilots ·

2025/01/14

In this episode, Tait Duryea and Ryan Gibson welcome Brian Feroldi, author of Why Does the Stock Market Go Up? to unpack the fundamentals of the stock market and explain strategies tailored for pilots and high-income professionals. Brian demystifies the difference between Roth and traditional 401(k) contributions, shares insights into dividend investing, and explains how to identify great companies for long-term growth. He also offers advice on working with financial advisors and highlights why most

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51:28

#92 - Opportunity Zones for Passive Income: Unlock...

Passive Income Pilots ·

2025/01/07

Dive into the intricacies of Opportunity Zones with this episode of Passive Income Pilots. Hosts Tait Duryea and Ryan Gibson are joined by CPA Nathan Sosa of Hall CPA, who demystifies Opportunity Zone (OZ) investments and their potential for tax deferral and appreciation. Whether you're an active investor or prefer passive opportunities, learn how OZs can defer taxes on gains from stocks, businesses, or real estate, and how they compare to other tax strategies like 1031 exchanges. Nathan explains

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132 results

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