Passive Income Pilots

#111 - Five Investing Strategies for High-Earning Pilots


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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.


Show notes:

(0:00) Intro

(1:59) Five investing categories for pilots

(3:38) Finding cash to invest smartly

(4:59) Whole life insurance and infinite banking

(10:17) 401(k) loans and strategic borrowing

(19:31) The short-term rental loophole explained

(24:53) Real estate professional (REP) status breakdown

(31:03) Cost segregation and bonus depreciation

(40:20) Outro


Connect with Hall CPA: https://bit.ly/HallCPA

Hall CPA - Passive Income Pilots 1-1 Tax Strategy Call: https://calendly.com/tax-smart-rei-plus/pip


Episodes mentioned:


#11 - How To Succeed In This High Interest Environment

#14 - Depreciation Demystified: Cost Segregation and Tax Savings in Real Estate with Toby Mathis

#23 - Counting the Cost: The Risks and Rewards of 401(k) Loans for Pilots

#36 - Decoding the Untapped Potential and Complex World of Self-Directed IRAs with Derreck Long

#44 - Mastering Year-End Tax Strategies: From IRA Conversions to Short-Term Rental Loopholes

#47 - Innovative Wealth Strategies: From Life Insurance to Alternative Investing with Christian Allen and Rod Zabriskie

#70 - Leveraging Life Insurance for Passive Income with Rod Zabriskie and Blake Brogan

#71 - 5 Creative Ways To Find Investment Cash

#74 - The Inside Track: Mastering Real Estate Syndications for Long-Term Success

#75 - Unlocking Real Estate Professional Status (REPS) with Brandon Hall

#82 - From LLCs and HSAs to Roth IRAs: Mastering Wealth Protection with Mark Kohler

#84 - Tax-Free Growth & Infinite Loans: Whole Life Insurance Strategies for High-Earners

#85 - Cost Segregation: The Tax Strategy You Can’t Afford to Ignore with Erik Oliver

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

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




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Do you have questions or want to discuss this episode? Contact us at [email protected] 


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.



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Passive Income PilotsBy Tait Duryea and Ryan Gibson

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