Passive Income Pilots

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 must-listen for high-income professionals looking to navigate passive investing with clarity and confidence.

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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 for anyone serious about turning real estate into real tax strategy.

Brandon Hall is a CP...

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 implementing the infinite banking concept in his own life, Brent transitioned to teaching others how to build wea...

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 achieving more life long before 65.

Brian Herriot is a financial advisor and founder of Herriot Business Consulting, where he specializes in guiding entrepreneurs and...

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 considered buying a business, this episode is packed with tactical insights.

James Spearman is a military-trained pilot, licensed...

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 involvement, tax strategies, and the realities of active vs. passive investing.

Michael Meylor is a major airline pilot and...

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 episode is a must-listen for high-income professionals looking to build freedom and legacy through smart investing.

Gino Barbaro is a...

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 development, he shifted to this truly passive strategy. Now, through Note Club...

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 jets, he saw firsthand the challenges pilots face in securing hangar space...

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 economic trends, the impact of inflation, and why 2025 may be one of the best buying opportunities in real estate.

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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 Lemaster is the founder and CEO of Rent to Retirement, a leading turnkey real estate investment company. A former...

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 buying in. The conversation also touches on industry trends, the role of insurance brokers, and how global factors impact insurance rates.

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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 founder of Smart Real Estate Coach, with over 30 years of experience in the real estate industry. Since 1991, he has built, brokered, and invested in p...

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 audits, 1031 exchanges, and passive vs. active use of an aircraft.

Ryan DeMoor is an...

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. Whether you’re considering a side hustle or a full-time business, Cliff provides actionable advice tailored to high-income professionals seeking financial independence.

Cliff Nonnenmacher is a...

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 alternative investments, and emphasizes the importance of building a strong network. Whether you're interested in public markets, private equity, real estate, or improving your financial strategy...

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 investors are better off with index funds. Whether you’re new to investing or looking to refine your strategy, this episode is packed with ac...

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 the steps, requirements, and benefits, all while offering actionable insights tailored to high-income earners, especially pilots.

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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. Learn to identify undervalued opportunities and position yourself for success in a shifting landscape.

Spencer Levy is the Senior Economic Advisor an...

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 your lifestyle for financial freedom. 

Carl Valeri is a captain with a major airli...

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 and Chief Economist for Airlines for America (A4A), the leading tr...

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 about aviation businesses, this episode is packed with actionable insights.

Gordon Alvord is an Alaska Airlines captain and co-founder of Rainier Fl...

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 dollars. Whether you're a super-saver or exploring alternative investments, this episode is packed with actionable insights to help you take control of your financial future.

Timothy...

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 episode takes you behind the scenes of one of the most fascinating innovations in modern air travel.

Ian Petchenik serves...

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 retroactively applying cost segregation to past investments. Whether you're a seasoned investor or new to real estate, this episode offers actionable advice on how cost segregation...

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 planning. Rod and Brenyn cover key policy structuring tips, like lump sum vs. monthly contributions, to help you create tax-efficient re...

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 tax planning insights.

Jesse Reed is a seasoned financial advisor with Creative Planning, specializing in wealth management for airline professionals. Wi...

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,” listeners will learn how to structure finances for long-term growth and protection.

Mark Kohler is a seasoned tax attorney, CPA, and author of f...

In this episode of Passive Income Pilots, hosts Tait Duryea and Ryan Gibson sit down with Jim Higgins, a former airline pilot turned co-founder and COO of a successful tech startup, Thread. Jim shares his unique journey, from negotiating contracts for American Eagle during 9/11 to leading a company that uses drones and AI for utility inspections. They discuss AI’s growing accessibility for building apps and businesses, the shift from pensions to defined contributions, and practical financial strategies for aspiring airline pilots. Jim also imparts key leadership lessons he learned in aviation and entrepreneurship.

Ji...

Welcome back to another exciting episode of Passive Income Pilots! This week, Tait and Ryan talk with Jules Sneddon and Trevor Moss from the National Real Estate Insurance Group to explore everything you need to know about insuring your real estate investments. From protecting against storm damage to navigating the rising insurance costs in high-risk areas like Florida, Jules and Trevor break down the essentials. They share expert tips on choosing the right coverage, avoiding common pitfalls, and how to vet a reliable insurance carrier. 

Jules Sneddon is the Executive Vice President of Sales a...

Welcome back to another inspiring episode of Passive Income Pilots! In this episode, Tait and Ryan sit with Colonel Eileen Collins, the first woman to command a NASA space shuttle. Colonel Collins shares her incredible journey, from becoming a pilot to breaking barriers in space exploration. She dives into leadership lessons, risk management, and the challenges of balancing family life with her high-flying career. Whether you’re an aspiring astronaut, pilot, or leader, this episode is packed with valuable insights and motivational stories that inspire you to aim higher!

Colonel Eileen Collins is a re...

In this episode of Passive Income Pilots, Tait and Ryan sit down with Casey Roloff, the visionary behind Seabrook, a seaside town in Washington. They explore how pilots and high-income professionals can strategically invest in real estate within Opportunity Zones while leveraging short-term rental tax loopholes and self-directed IRAs for significant tax benefits. Casey shares his inspiring journey from house painting to developing Seabrook, highlighting how investors can balance lifestyle with passive income opportunities. Discover how a well-placed seaside investment can create long-term value, financial gains, and personal enjoyment.

Casey Roloff is the founder...

Welcome back to another exciting episode of the Passive Income Pilots! Today, Tait and Ryan dive into the world of aircraft ownership, tax advantages, and leaseback strategies with guest Luke Lysen from The Flight Academy and Aerista. They explore how pilots and high-income earners can purchase an aircraft, rent it out to a flight school, and leverage tax benefits to offset costs, turning a passion for flying into a financially viable investment. If you've ever dreamt of owning an aircraft or are curious about the tax strategies that make it feasible, this episode is for you!

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In this episode of Passive Income Pilots, Tait Duryea takes you back to one of the most downloaded episodes in the show's history with Toby Mathis from Anderson Advisors. Discover how tax laws can work for you through real estate investments, cost segregation, and bonus depreciation strategies. Toby breaks down the game-changing legal strategies high-income earners can use to reduce their tax burden and maximize returns drastically. If you're a pilot frustrated with taxes or looking to level up your knowledge, this episode is packed with powerful insights.

Toby Mathis is a tax attorney...

Welcome back to Passive Income Pilots! This week, Tait and Ryan are joined by Brandon Hall, a top CPA and founder of Hall CPA, PLLC, to dive into one of the most powerful tax strategies for high-income professionals: real estate professional status. With over 800 clients and a specialization in real estate tax strategies, Brandon breaks down the benefits, nuances, and how pilots can leverage this loophole to minimize taxes and maximize wealth. Whether you're a seasoned investor or just curious, this episode is packed with insights you don’t want to miss!

Brandon Hall is...

Welcome to another episode of Passive Income Pilots! This week, Tait and Ryan dive deep into the world of real estate syndications—a game-changing investment strategy for busy professionals, especially pilots. They break down what syndications are, how they work, and the pros and cons of this passive income stream. From navigating the complexities of recourse vs. non-recourse loans to understanding the importance of vetting syndicators, this episode is packed with valuable insights to help you soar above the turbulence in your investment journey. Tune in to learn how you can achieve financial freedom without the daily grind of pr...

Welcome to another insightful episode of Passive Income Pilots! This week, Tait and Ryan are joined by Dr. Glenn Mueller, a seasoned economist and real estate professor with over 40 years of experience. Dr. Mueller explores the current economic landscape, the real estate market, and the fascinating REIT world. Whether you're curious about market cycles or looking to understand how to analyze REITs like a pro, this episode is packed with expert knowledge. Plus, stick around as Dr. Mueller reveals his daily go-to sources for staying ahead in real estate.

Dr. Glenn Mueller is a...

In this week's episode of Passive Income Pilots, Tait and Ryan are thrilled to have Joe LoRusso back on the show for an essential update on the evolving landscape of pilot mental health regulations. Since his last appearance, significant changes have been implemented by the FAA, including new guidelines for mental health treatments and expanded medication approvals. Joe breaks down what these changes mean for pilots navigating the complex aeromedical process. If you're a pilot or know someone facing mental health challenges, this episode is a must-listen for staying informed and protecting your medical certification. 

Welcome back to another episode of Passive Income Pilots! Today, Tait and Ryan dive into five unconventional ways to unlock cash for your next investment. Whether leveraging home equity, rolling over an old 401k, or borrowing against your stock portfolio, this episode is packed with actionable strategies to help you soar to new financial heights. Tune in to discover how you can multiply your investment opportunities and optimize your financial toolkit. Plus, don't miss the details about our first-ever webinar featuring the experts on whole life insurance strategies. Get ready to elevate your passive income game!

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Welcome to another enlightening episode of Passive Income Pilots! Today, Tait and Ryan welcome Rod and Blake from Money Insights. Previously featured in episode 47, Rod and Blake are experts in leveraging life insurance for wealth-building. In this deep dive, we uncover how to use a specialized life insurance strategy to enhance investment returns, minimize taxes, and provide financial security for your family. This episode is packed with practical insights on optimizing cash flow, estate planning, and more. Tune in and learn how to elevate your financial game with these powerful strategies!

Rod Zabriskie (President...