Passive Income Pilots

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.

Sh...

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...

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.

Show n...

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...