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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

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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49:12

#91 - Interest Rates, Submarkets, and CRE's Future...

Passive Income Pilots ·

2024/12/31

Spencer Levy, a leading expert from CBRE, joins Tait Duryea and Ryan Gibson to break down the current state of commercial real estate (CRE). He explains how rapid interest rate changes are reshaping the market, highlights key megatrends like reshoring and live-work-play neighborhoods, and offers advice on navigating submarkets. Whether you’re a seasoned investor or just getting started, Spencer shares valuable strategies to help pilots and high-income professionals make smarter CRE investments

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49:22

#90 - Balancing Flying, Business Ownership, and...

Passive Income Pilots ·

2024/12/24

In this action-packed episode of Passive Income Pilots, Tait Duryea and Ryan Gibson sit down with Carl Valeri, an airline captain and experienced entrepreneur, to share actionable strategies to balance a flying career with building a passive income. Carl dives into creative ways to start or buy a business, reduce your tax burden, and even transition to aviation from another career. You’ll hear inspiring stories of people who’ve turned hobbies into thriving businesses and learn how you can design

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41:04

#89 - Air Traffic, Pilot Pay, and Airline Economics...

Passive Income Pilots ·

2024/12/17

In this episode, Tait Duryea and Ryan Gibson sit down with John Heimlich, Chief Economist for Airlines for America (A4A), to unpack the challenges and wins shaping the airline industry. From air traffic control staffing shortages to the impact of pilot pay increases and aircraft delivery delays, John shares key insights into the state of U.S. airlines. He also discusses A4A's advocacy work and what the future holds for pilots and the broader aviation ecosystem.John Heimlich is the Vice President

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46:34

#88 - Flight Schools and Passive Income: Insights...

Passive Income Pilots ·

2024/12/10

In this episode of Passive Income Pilots, hosts Tait Duryea and Ryan Gibson talk with Gordon Alvord, Alaska Airlines captain and co-founder of Rainier Flight Service. Gordon shares how a 2008 furlough led to creating Washington State’s largest flight school, with over 70 aircraft and a reputation for innovation. Discover how he and his partner used business acumen, strategic investments, and bonus depreciation to build a scalable operation. Whether you're a pilot seeking side hustles or curious

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50:41

#87 - The Mega Backdoor Roth and How Pilots Can...

Passive Income Pilots ·

2024/12/03

In this episode of Passive Income Pilots, Tait Duryea and Ryan Gibson welcome back financial expert Timothy Pope to unravel the complexities of retirement strategies for high-income professionals, focusing on the Mega Backdoor Roth. Timothy explains how this powerful tool allows pilots to contribute significantly more to their 401(k) accounts, unlocking tax-free growth opportunities. You will gain clarity on Roth vs. Traditional contributions, tax implications, and the strategic use of post-tax

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33:52

#86 - Mapping the Skies: The Tech Behind Real-Time...

Passive Income Pilots ·

2024/11/26

Welcome back to another episode of Passive Income Pilots! In this episode, Tait Duryea and Ryan Gibson step outside financial strategies to explore the world of real-time flight tracking with Ian Petchenik, Director of Communications at FlightRadar24. Ian shares insights into the app that has become essential for aviation enthusiasts and professionals alike, with its vast network of over 41,000 ADS-B receivers tracking more than 200,000 flights daily. Whether a pilot or an aviation enthusiast, this

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47:59

#85 - Cost Segregation: The Tax Strategy You Can’t...

Passive Income Pilots ·

2024/11/19

Welcome back to another episode of Passive Income Pilots! In this episode of Passive Income Pilots, Tait Duryea and Ryan Gibson are joined by Erik Oliver, Vice President of Cost Segregation Authority, to dive deep into cost segregation. Erik explains how this tax strategy accelerates real estate depreciation, enabling investors to unlock substantial tax savings. He covers key topics like the benefits of reclassifying building components, qualifying short-term rentals for bonus depreciation, and

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39:52

#84 - Tax-Free Growth & Infinite Loans: Whole Life...

Passive Income Pilots ·

2024/11/12

Welcome back to another episode of Passive Income Pilots! In this episode, Tait Duryea hosts Rod Zabriskie and Brenyn McConnell from Money Insights to explore how whole life insurance can be a powerful investment tool. They discuss how pilots and high-income earners can use structured whole life policies to build tax-free growth and take policy loans for investments like real estate. You’ll learn how these policies offer a steady 5% return, liquidity for new investments, and options for legacy

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53:55

#83 - Market-Based Cash Balance Plans with Jesse Reed

Passive Income Pilots ·

2024/11/06

In this episode, hosts Tait Duryea and Ryan Gibson welcome back financial planning expert and pilot Jesse Reed to dive deep into market-based cash balance plans—a retirement vehicle being implemented by airlines specifically for high-earning pilots facing 401(k) spillover limits. Jesse unpacks how pilots can strategically manage these plans to maximize retirement savings and minimize tax burdens. Tune in to learn how to navigate 401(k) limits, Roth and after-tax contribution strategies, and advanced

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1:01:03

#82 - From LLCs and HSAs to Roth IRAs: Mastering...

Passive Income Pilots ·

2024/10/29

In this episode of Passive Income Pilots, hosts Tait Duryea and Ryan Gibson welcome tax attorney Mark Kohler to answer popular questions on tax strategies for high-income professionals. With two decades of experience, Mark breaks down essentials from self-directed IRAs to maximizing HSAs, Roth IRAs, and other tax-advantaged accounts, plus strategies for lowering tax liability through real estate and business. With actionable insights on 1031 exchanges, Roth chunking, and creating a “family board,”

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142 results

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