Passive Income Pilots

Latest Episodes:

#110 - The IRA Club Advantage: The Self-Directed IRA Strategy for Pilots with Ramez Fakhoury May 13, 2025

Show notes

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 discovered a passion for alternative investing and now helps individuals unlock their retirement capital for real estate and other private assets. His practical approach and deep knowledge make complex financial strategies accessible for pilots and high-income earners.

Show notes:

(0:00) Intro

(01:07) Introduction to Ramez and IRA Club

(04:49) Three options when leaving an airline

(06:11) True vs. false self-direction explained

(10:27) Why you shouldn't rush rollover decisions

(14:39) What you can't invest in with IRAs

(20:48) Why IRA Club's structure stands out

(27:42) Contribution limits vs. rollover power

(38:56) Partnering personal and retirement funds

(46:59) Real estate in IRAs: tax pros and cons

(51:20) Outro

Connect with Ramez:

Website: https://www.iraclub.com/

LinkedIn: https://www.linkedin.com/company/the-ira-club/

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See you on the next one!

*Legal Disclaimer*

The content of this podcast is provided solely for educational and informational purposes. The views and opinions expressed are those of the hosts, Tait Duryea and Ryan Gibson, and do not reflect those of any organization they are associated with, including Turbine Capital or Spartan Investment Group. The opinions of our guests are their own and should not be construed as financial advice. This podcast does not offer tax, legal, or investment advice. Listeners are advised to consult with their own legal or financial counsel and to conduct their own due diligence before making any financial decisions.

#109 - The Flight Plan for Syndications: Risk, Returns, and Real Wealth May 06, 2025

Show notes

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 notes:

(0:00) Intro

(02:23) Active vs passive investing explained

(04:03) Is syndication risky? Understanding real risk

(05:22) Core, Core Plus, Value Add, Opportunistic defined

(10:11) Operational vs physical value-add

(13:35) What are risk-adjusted returns?

(17:19) How leverage impacts risk

(20:02) DSCR vs LTV: What's more important?

(22:59) Preferred return vs cash flow

(33:50) What is an accredited investor?

(38:55) Outro

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See you on the next one!

*Legal Disclaimer*

#108 - Case Study: Real Estate Professional Status That Held Up in Court with Brandon Hall Apr 30, 2025

Show notes

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 CPA and the founder of Hall CPA, a firm specializing in real estate tax strategy. Known for his deep understanding of IRS code and investor-focused guidance, Brandon walks through a landmark tax court case that underscores how full-time professionals, including pilots, can successfully claim real estate professional status.

Show notes:

(0:00) Intro

(01:13) History of passive activity rules

(02:49) Short-term rentals vs. REP loophole

(04:33) Why pilots are uniquely eligible

(05:29) REP for married couples explained

(06:49) Brandon Hall sets up the case study

(09:12) Mr. Miller's job and schedule details

(13:18) Proving material participation

(16:31) The grouping election mistake to avoid

(19:24) Outro

Connect with Brandon:

https://bit.ly/HallCPA - Recommended CPA for real estate-focused tax strategy

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Do you have questions or want to discuss this episode? Contact us at ask@passiveincomepilots.com

See you on the next one!

*Legal Disclaimer*

#107 - Take Control of Your Capital: Infinite Banking Strategy With Brent Kesler Apr 22, 2025

Show notes

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 wealth by using high-cash-value life insurance policies. As the founder of The Money Multiplier, he now helps high-income individuals take control of their finances outside of traditional banking and investment models.

Interested in getting started with a policy?

We recommend reaching out to our trusted partners at Money Insights (https://moneyinsightsgroup.com) for a customized strategy designed specifically for high-income professionals and pilots.

Show notes:

(0:00) Intro

(03:55) Whole life insurance vs. “infinite banking”

(11:12) Brent's backstory and entry into life insurance

(18:46) Debt, leverage, and using your policy

(24:03) Why whole life is NOT an investment

(27:43) How policies build over time

(32:17) Why this strategy isn’t mainstream

(34:46) How much life insurance banks actually own

(36:39) Why agents don’t often recommend this approach

(37:50) Outro

Connect with Brent:

Free eBook: Mapping Out the Millionaire Mystery by Brent Kessler and Chris Naugle
📧 Request via email: brent@themoneymultiplier.com
🎥 90-minute video at www.themoneymultiplier.com

If you’re interested in exploring high cash value life insurance as a personal banking strategy, we recommend connecting with our trusted team at Money Insights: https://moneyinsightsgroup.com

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Get our updates on LinkedIn: https://www.linkedin.com/company/passive-income-pilots/

Do you have questions or want to discuss this episode? Contact us at ask@passiveincomepilots.com

See you on the next one!

*Legal Disclaimer*

#106 – Time Freedom and Cash Strategies with Brian Herriot Apr 15, 2025

Show notes

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 high-income earners through strategies that prioritize flexibility and purpose over traditional retirement timelines. With a rich background in consulting and business, Brian brings a refreshingly holistic approach to financial planning—centered around "time freedom." He helps clients structure their finances to enjoy life sooner, with smart cash management, passive income, and intentional lifestyle design.

Show notes:

(0:00) Intro

(02:38) Meet Brian Herriot and his unique financial philosophy

(07:04) Time freedom vs. traditional retirement

(09:53) How Brian redesigned his life post-2020

(16:49) The 10–30% cash rule explained

(22:09) Ticker symbols for high-yield cash storage

(24:55) Best passive income streams for pilots

(27:49) How to prioritize investments by liquidity

(36:23) Financial planning for pilot-entrepreneur households

(38:50) Outro

Connect with Brian Herriot:

Website: https://www.herriotconsulting.com
LinkedIn: https://www.linkedin.com/in/brianherriot
Time Freedom Calculator: https://timefreedomcalculator.com/

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Do you have questions or want to discuss this episode? Contact us at ask@passiveincomepilots.com

See you on the next one!

*Legal Disclaimer*

#105 - Buying and Building a Profitable Aviation Business with James Spearman Apr 08, 2025

Show notes

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 aircraft mechanic, and savvy entrepreneur based in East Tennessee. He owns Spearman Aircraft, an aviation maintenance business he acquired through seller financing and scaled tenfold, as well as a seaplane business offering flight training and experiences. James blends hands-on aviation expertise with smart business systems, marketing, and mentorship to create scalable, profitable ventures.

Show notes:

(0:00) Intro

(04:23) Early side hustles and real estate

(05:39) Zero-down business acquisition

(07:53) Seller financing and boomers retiring

(12:28) Why buying what you know matters

(16:07) Learning marketing through necessity

(20:53) Coaching and investing in yourself

(31:34) Building operational systems

(36:38) Preparing a business to sell

(43:18) Outro

Connect with James Spearman:

Website: https://www.spearmanaircraft.com

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Get our updates on LinkedIn: https://www.linkedin.com/company/passive-income-pilots/

Do you have questions or want to discuss this episode? Contact us at ask@passiveincomepilots.com

See you on the next one!

*Legal Disclaimer*

#104 - Active vs. Passive: Storage Strategies from the Flight Deck with Michael Meylor Apr 01, 2025

Show notes

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 former military aviator who has successfully built a self-funded real estate portfolio focused on self-storage facilities. With a background in tech and an MBA, Michael applied his analytical skills to real estate investing, scaling from single-family rentals to large commercial properties. Alongside his wife, he’s built a lean operation and shares practical insights into active investing, SBA loans, and family wealth-building strategies.

Show notes:

(0:00) Intro

(02:32) Overcoming fear of real estate investing

(06:21) Why self-storage and the first deal

(09:36) Adding value and refinancing strategy

(12:35) Learning financial modeling and analysis

(18:06) Where to get educated in self-storage

(23:34) Minimum viable size for self-storage

(27:11) Active investing: The reality check

(35:09) Why go active? The long-term upside

(45:22) Most surprising lesson from investing

(48:18) Outro

Connect with Michael Meylor:

LinkedIn: https://www.linkedin.com/in/michael-m-4588101a/
Website: https://greenlightstorage.com/
Email: Michael@GreenlightStorage.com

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Do you have questions or want to discuss this episode? Contact us at ask@passiveincomepilots.com

See you on the next one!

*Legal Disclaimer*

#103 - Multifamily Mastery: Building Cashflow and Legacy with Gino Barbaro Mar 25, 2025

Show notes

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 multifamily real estate investor, author, and co-founder of Jake & Gino, an education platform focused on apartment investing. With a portfolio of over 1,800 units, Gino teaches others how to build wealth through multifamily real estate, values-based leadership, and financial literacy. He’s the author of Happy Money, Happy Family, Happy Legacy, which integrates money mindset with real estate investing and legacy building.

Show notes:

(0:00) Intro

(01:13) Life lessons from the family restaurant

(05:30) Why real estate is Gino’s chosen asset

(08:54) The philosophy behind "Happy Money"

(13:23) Saving vs. investing mindset

(19:54) Whole life insurance explained

(25:12) Teaching financial values to kids

(29:43) Why new investors struggle

(31:46) Exit strategies in real estate

(36:19) Current real estate market outlook

(42:18) Outro

Links mentioned:

Optimize Your Policy: A Practical Workshop for Passive Income Pilots: https://youtu.be/higMHZI4Itw

Schedule a Call with a member of the Money Insights team: https://moneyinsightsgroup.com/#schedule-call

Connect with Gino Barbaro:

LinkedIn: https://www.linkedin.com/in/gino-barbaro-03973b4b/
Website: https://noteclubusa.com/

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Do you have questions or want to discuss this episode? Contact us at ask@passiveincomepilots.com

See you on the next one!

*Legal Disclaimer*

#102 - Creating True Passive Income Through Note Investing with Tom Force Mar 18, 2025

Show notes

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 USA, he helps pilots and investors build wealth with real estate notes.

Show notes:

(0:00) Intro

(04:46) Getting started in real estate investing

(09:16) Why Tom transitioned to note investing

(11:31) The appeal of note investing for pilots

(20:34) How note investing compares to rental real estate

(24:05) Why banks & investors sell mortgage notes

(28:56) The risk vs. reward of note investing

(35:35) Steps to start investing in notes

(38:09) Seller financing strategies & tax benefits

(45:18) Outro

Connect with Tom Force:

LinkedIn: https://www.linkedin.com/in/tomforce/
Website: https://noteclubusa.com/

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Get our updates on LinkedIn: https://www.linkedin.com/company/passive-income-pilots/

Do you have questions or want to discuss this episode? Contact us at ask@passiveincomepilots.com

See you on the next one!

*Legal Disclaimer*

#101 - Airbnb for Aircraft: Hangar Investing & Aviation Real Estate with Trenton Ray Mar 11, 2025

Show notes

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. This led him to co-found Hangar Direct, a platform that optimizes available hangar space, making it easier for aircraft owners to find and rent storage.

Show notes:

(0:00) Intro

(04:19) The frustration of finding hangar space

(05:25) Hangar Direct: The Airbnb for hangars

(07:43) Why demand for hangars is skyrocketing

(10:05) Optimizing underutilized hangars for better returns

(15:40) Is hangar ownership a good investment?

(17:23) Understanding land leases and hangar ownership risks

(24:11) How to finance a hangar: Loans vs. cash purchases

(33:09) Monetizing underused aircraft through dry leasing

(40:40) Outro

Connect with Trenton Ray: