Passive Income Pilots

Tait Duryea and Ryan Gibson
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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 seasoned pilot or just starting out, we'll equip you with the expertise and confidence you need to upgrade your money and achieve true financial independence.

  1. HACE 5 DÍAS

    #146 - Aircraft Tax Write-Offs Explained by a Former IRS Auditor, Victoria Boon

    Hosts Tait Duryea and Ryan Gibson welcome former IRS auditor Victoria Boon to cut through the noise around aircraft tax deductions. Learn how bonus depreciation really works, why aircraft are treated differently from real estate, and what the IRS actually looks for during an audit. From Delta bonus taxation to leasebacks, qualified business use, and depreciation recapture, this episode is essential listening for pilots considering aircraft ownership as a tax strategy. Victoria Boon spent 22 years at the IRS as a subject matter expert, including leading national audits focused on aircraft deductibility. She now co-owns Boon.tax and founded Boon Tax Educators, where she provides tax education for CPAs, enrolled agents, and investors. In this conversation, Victoria shares rare, insider insight into aircraft write-offs, audit triggers, and the mistakes that get taxpayers into trouble. Show notes: (0:00) Intro (01:44) Why bonuses are over-withheld (04:39) Aircraft deductions overview (07:18) Bonus depreciation rules (08:16) Qualified business use explained (11:37) Depreciation recapture basics (14:29) IRS documentation requirements (18:02) Audit horror stories (22:21) Why aircraft trigger audits (37:56) 50% rule and bonus loss (39:30) Passive Vs. Qualified business use (46:36) Social media tax myths exposed (53:45) Outro Connect with Victoria Boon: Website: https://boon.tax/ Structured Tax Education Classes and Workshops: https://boontaxeducators.com/  If you’re interested in participating, the latest institutional-quality self-storage portfolio is available for investment now at: https://turbinecap.investnext.com/portal/offerings/8449/houston-storage/  — You've found the number one resource for financial education for aviators! Please consider leaving a rating and sharing this podcast with your colleagues in the aviation community, as it can serve as a valuable resource for all those involved in the industry. Remember to subscribe for more insights at PassiveIncomePilots.com! https://passiveincomepilots.com/  Join our growing community on Facebook: https://www.facebook.com/groups/passivepilots Check us out on Instagram @PassiveIncomePilots: https://www.instagram.com/passiveincomepilots/ Follow us on X @IncomePilots: https://twitter.com/IncomePilots 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 at 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.

    54 min

  2. 4 FEB

    #145 - Bonus Depreciation & Cost Seg: The Tax Strategy Pilots Can’t Ignore with Gian Pazzia

    What if the IRS already allows you to write off far more of your real estate, but no one ever showed you how? In today’s episode, Tait Duryae sits down with Gian Pazzia to break down cost segregation in plain English and explain why it remains one of the most powerful tax strategies for real estate investors. Building on last week’s depreciation primer with Hall CPA, this episode covers how cost segregation works, when it makes sense, audit risk myths, and how pilots can apply it to everything from single-family rentals to commercial deals. You’ll also learn about a new, low-cost software option that makes cost seg accessible to smaller investors. Gian Pazzia is a structural engineer and tax strategist with over 25 years of experience specializing in cost segregation studies. He is the founder of KBKG, one of the largest cost segregation firms in the country. Gian began his career at Arthur Andersen, working on large-scale commercial projects, and has since helped thousands of real estate investors legally accelerate depreciation and reduce tax liability through IRS-compliant strategies. Show notes: (0:00) Intro (2:18) Why cost segregation matters (5:46) Cost seg vs straight-line depreciation (8:39) What assets qualify for write-offs (10:18) IRS-approved depreciation methods (14:54) Land value impact on tax benefits (19:24) Cost seg for small properties (25:32) Audit risk explained clearly (34:04) Using cost seg on older properties (37:40) DIY software walkthrough (39:10) Outro Connect with Gian: Website: https://www.kbkg.com/management/gian-pazzia Cost Segregation Software: https://www.costsegregation.com/ Promo Code: PILOTSCODE (10% off for first-time users) Related Episode: #144 - Depreciation, Cost Segs, and the IRS Rules Pilots Miss with Brandon Hall If you’re interested in participating, the latest institutional-quality self-storage portfolio is available for investment now at: https://turbinecap.investnext.com/portal/offerings/8449/houston-storage/  — You've found the number one resource for financial education for aviators! Please consider leaving a rating and sharing this podcast with your colleagues in the aviation community, as it can serve as a valuable resource for all those involved in the industry. Remember to subscribe for more insights at PassiveIncomePilots.com! https://passiveincomepilots.com/  Join our growing community on Facebook: https://www.facebook.com/groups/passivepilots Check us out on Instagram @PassiveIncomePilots: https://www.instagram.com/passiveincomepilots/ Follow us on X @IncomePilots: https://twitter.com/IncomePilots 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 at 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.

    39 min

  3. 27 ENE

    #144 - Depreciation, Cost Segs, and the IRS Rules Pilots Miss with Brandon Hall

    Tait Duryea is joined by Brandon Hall to break down one of the most misunderstood tools in real estate investing: depreciation. From straight-line depreciation to cost segregation and 100 percent bonus depreciation, this episode explains how so-called “phantom losses” can legally reduce or even eliminate taxable income for pilots and other high earners. They also cover depreciation recapture, common investor mistakes, and why experienced investors think in decades, not tax years. Brandon Hall is the founder of Hall CPA, widely known as The Real Estate CPA. After working at Ernst & Young and PwC, he left the corporate world to build a national firm focused exclusively on real estate investors. His team supports everyone from first-time landlords to large syndications and funds, with a practical, no-nonsense approach to depreciation, cost segregation, and long-term tax strategy. Show notes: (0:00) Intro (01:14) What depreciation really is (03:06) Brandon’s CPA and real estate background (09:20) Why assets depreciate while values rise (11:15) Straight-line depreciation explained (14:01) Leverage and real estate returns (18:42) Tax losses vs operating income (20:57) Cost segregation basics (23:07) Bonus depreciation returns in 2025 (31:41) Depreciation recapture explained (46:42) The “lazy man’s” 1031 strategy (1:00:04) Outro Connect with Brandon Hall: Website: https://www.therealestatecpa.com/ Podcast: https://www.therealestatecpa.com/podcasts/  If you’re interested in participating, the latest institutional-quality self-storage portfolio is available for investment now at: https://turbinecap.investnext.com/portal/offerings/8449/houston-storage/  — You've found the number one resource for financial education for aviators! Please consider leaving a rating and sharing this podcast with your colleagues in the aviation community, as it can serve as a valuable resource for all those involved in the industry. Remember to subscribe for more insights at PassiveIncomePilots.com! https://passiveincomepilots.com/  Join our growing community on Facebook: https://www.facebook.com/groups/passivepilots Check us out on Instagram @PassiveIncomePilots: https://www.instagram.com/passiveincomepilots/ Follow us on X @IncomePilots: https://twitter.com/IncomePilots 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* 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.

    1 h

  4. 20 ENE

    #143 - How High Cash Value Life Insurance Works for Pilots with Rod Zabriskie

    Could life insurance be a better cash-flow tool than a savings account? Tait Duryea and Ryan Gibson sit down with Rod Zabriskie from Money Insights Group to break down how high cash value whole life insurance can be used as a powerful cash-flow tool for pilots and investors. They cut through the confusion around “infinite banking” and explain how properly structured policies can improve liquidity, reduce friction when investing, and add meaningful long-term returns. This episode walks through real pilot use cases, common mistakes, and why this strategy has become a quiet cornerstone for sophisticated alternative investors. Rod Zabriskie, president of the Money Insights Group, specializes in advanced wealth-building strategies using life insurance as a financial tool. With a pragmatic, education-first approach, Rod helps high-income professionals, especially pilots, understand how to leverage whole life policies for liquidity, tax advantages, and long-term returns. Show notes: (0:00) Intro (0:14) First flight in a J3 Cub (3:50) Why life insurance matters here (4:23) High cash value strategy explained (6:13) Cutting through infinite banking noise (8:06) Investment optimizer vs banking hype (11:09) Setting flexible funding ranges (13:29) Term insurance vs whole life (15:21) Using policy loans to invest (18:40) Why brokers matter for pilots (31:05) How this adds a million dollars (35:01) Outro Connect with Rod: Website: https://moneyinsightsgroup.com Youtube: https://www.youtube.com/channel/UCW0fBokwg09-2H2kXWK5Zfw Related Episodes: #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#84 - Tax-Free Growth & Infinite Loans: Whole Life Insurance Strategies for High-Earners#122 - How Pilots Use Whole Life Insurance to Fund Investments with Rod Zabriskie If you’re interested in participating, the latest institutional-quality self-storage portfolio is available for investment now at: https://turbinecap.investnext.com/portal/offerings/8449/houston-storage/  — You've found the number one resource for financial education for aviators! Please consider leaving a rating and sharing this podcast with your colleagues in the aviation community, as it can serve as a valuable resource for all those involved in the industry. Remember to subscribe for more insights at PassiveIncomePilots.com! https://passiveincomepilots.com/  Join our growing community on Facebook: https://www.facebook.com/groups/passivepilots Check us out on Instagram @PassiveIncomePilots: https://www.instagram.com/passiveincomepilots/ Follow us on X @IncomePilots: https://twitter.com/IncomePilots 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* 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.

    40 min

  5. 13 ENE

    #142 - Tax Planning for W-2 Pilots Without Complex Businesses with Gary Heldt

    Are you paying for a high-powered CPA when your tax situation doesn’t actually require one? In this episode, Tait Duryea and Ryan Gibson sit down with CPA Gary Heldt to clarify what smart tax planning really looks like for high-income pilots with relatively simple financial lives. They break down how W-2 earners can optimize taxes without complex businesses, aggressive strategies, or unnecessary fees. Gary explains how often-overlooked fundamentals like benefits planning, estimated taxes, and coordinated advice can quietly compound into meaningful long-term gains. If you want clarity, confidence, and a more intentional approach to your CPA relationship, this episode delivers. Gary Heldt is a CPA, Certified Tax Coach, and founder of Small Business Advisors. With over 25 years of experience, he helps high-income professionals make better tax decisions through a consultative, family-office-style approach that prioritizes clarity over complexity. Show notes: (0:00) Intro (0:23) Why pilots overpay for CPAs (1:25) Family-office thinking for W-2 earners (3:42) Gary’s path into tax planning (8:13) Missed tax moves for W-2 professionals (11:57) What a good CPA should do (16:28) Why education beats tax prep (24:34) Bracket strategy and timing income (28:50) Estimated taxes pilots overlook (34:18) Turning tax savings into investments (43:57) Outro Connect with Gary Heldt: Sign up directly on the site. Choose personal, business, or both newsletter options: https://www.sbadvisors.cc/  Gary's Podcast: https://www.sbadvisors.cc/resources/podcasts  If you’re interested in participating, the latest institutional-quality self-storage portfolio is available for investment now at: https://turbinecap.investnext.com/portal/offerings/8449/houston-storage/  — You've found the number one resource for financial education for aviators! Please consider leaving a rating and sharing this podcast with your colleagues in the aviation community, as it can serve as a valuable resource for all those involved in the industry. Remember to subscribe for more insights at PassiveIncomePilots.com! https://passiveincomepilots.com/  Join our growing community on Facebook: https://www.facebook.com/groups/passivepilots Check us out on Instagram @PassiveIncomePilots: https://www.instagram.com/passiveincomepilots/ Follow us on X @IncomePilots: https://twitter.com/IncomePilots 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* 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.

    44 min

  6. 6 ENE

    #141 - How Pilots Can Use Business Structures to Reduce Taxes with Toby Mathis

    Tait Duryea and Ryan Gibson sit down with Toby Mathis to unpack one of the most misunderstood topics for high-income pilots: business structure and taxes. They explain when to use sole proprietorships, LLCs, S-corps, and C-corps, how losses and profits flow to your personal return, and why entity choice impacts audit risk and mortgage eligibility. This episode is a practical roadmap for pilots starting side hustles who want to lower taxes, protect assets, and avoid costly mistakes. Toby Mathis is a nationally recognized tax attorney, investor, and educator, best known for simplifying complex tax and asset-protection strategies for entrepreneurs and high-income professionals. He is a founding partner of Anderson Advisors, where he helps clients legally reduce taxes, structure businesses, and protect wealth. In this episode, Toby breaks down entity structures, audit risk, and practical tax strategies pilots can apply when starting or scaling a business. Show notes: (0:00) Intro (0:11) Why entity structure matters (1:40) Side hustles and W-2 tax offsets (3:01) Starting a business vs real estate (6:42) Flow-through Vs. C-corp taxation (8:49) Mortgage qualification pitfalls (11:38) Legitimate expense strategies (15:00) Augusta rule and home office (21:48) Why sole proprietors get audited (28:25) Profit Vs. Loss by entity type (41:20) Schedule C Vs. Schedule E risk (56:14) Outro Connect with Toby Mathis: Website: https://tobymathis.com/ YouTube: https://www.youtube.com/channel/UCX5nh607M8hSBLiMB9MgbIQ Books: https://www.amazon.com/Tax-Wise-Business-Ownership-Toby-Mathis/dp/0979786002 Tax Tuesday: https://andersonadvisors.com/tax-tuesdays/ If you’re interested in participating, the latest institutional-quality self-storage portfolio is available for investment now at: https://turbinecap.investnext.com/portal/offerings/8449/houston-storage/  — You've found the number one resource for financial education for aviators! Please consider leaving a rating and sharing this podcast with your colleagues in the aviation community, as it can serve as a valuable resource for all those involved in the industry. Remember to subscribe for more insights at PassiveIncomePilots.com! https://passiveincomepilots.com/  Join our growing community on Facebook: https://www.facebook.com/groups/passivepilots Check us out on Instagram @PassiveIncomePilots: https://www.instagram.com/passiveincomepilots/ Follow us on X @IncomePilots: https://twitter.com/IncomePilots 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* 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.

    56 min

  7. 30/12/2025

    #140 - From Goals to Execution: A Year-End Playbook

    Tait Duryea and Ryan Gibson close out 2025 by pulling back the curtain on how high performers actually plan, execute, and stay intentional across money, business, and family life. From Spartan’s acquisition pace and Turbine’s investor roadmap to family board meetings, goal frameworks, and habit formation, this episode offers a grounded look at what it takes to build momentum year after year. If you want clarity instead of drift and action instead of resolutions, this conversation sets the tone for a focused, intentional 2026. Do not just listen. Decide who you are becoming and move. Show notes: (0:00) Intro (2:27) Family board meetings explained (4:32) Objectives and key results framework (6:29) Spartan’s 2025 growth numbers (9:29) Turning big ideas into action (12:21) Why most people never get clear (15:49) Day one Vs. One day mindset (18:40) Stability, mentorship, and leadership (21:02) Why 2026 looks like opportunity (23:36) Outro If you’re interested in participating, the latest institutional-quality self-storage portfolio is available for investment now at: https://turbinecap.investnext.com/portal/offerings/8449/houston-storage/  — You've found the number one resource for financial education for aviators! Please consider leaving a rating and sharing this podcast with your colleagues in the aviation community, as it can serve as a valuable resource for all those involved in the industry. Remember to subscribe for more insights at PassiveIncomePilots.com! https://passiveincomepilots.com/  Join our growing community on Facebook: https://www.facebook.com/groups/passivepilots Check us out on Instagram @PassiveIncomePilots: https://www.instagram.com/passiveincomepilots/ Follow us on X @IncomePilots: https://twitter.com/IncomePilots 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* 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.

    24 min

  8. 24/12/2025

    #139 - How to Run Single-Family Rentals Like a REIT with Matthew Whitaker

    What if managing rentals like an institution is the key to higher returns and less stress? Hosts Tait Duryea and Ryan Gibson talk with Matthew Whitaker, founder of Evernest, about scaling property management with systems, data, and AI. From HELOC-driven growth to managing 20,000 homes nationwide, this conversation breaks down why professional operations, fraud prevention, and institutional discipline can transform single-family and small multifamily investing for pilots. Matthew Whitaker is the founder of Evernest, a nationwide property management platform serving over 20,000 rental homes across 50 markets. A former single-family investor who scaled through multiple market cycles, Matthew now focuses on applying institutional systems, data, and AI to professionalize rental operations and reduce friction for real estate investors. Show notes: (0:00) Intro (0:19) Why property management changes everything (1:22) From 30 homes to 20,000 doors (5:03) Using HELOCs to scale real estate (10:32) Why paying off your house isn’t safer (16:23) Inside Evernest’s national platform (18:21) Tenant fraud and underwriting risks (22:12) Why in-house maintenance lowers costs (31:21) AI predicting repairs and NOI (34:10) Institutional systems for small rentals (46:07) How to work with Evernest (47:14) Outro Connect with Matthew Whitaker: Website: https://www.evernest.co/ — If you’re interested in participating, the latest institutional-quality self-storage portfolio is available for investment now at: https://turbinecap.investnext.com/portal/offerings/8449/houston-storage/  — You've found the number one resource for financial education for aviators! Please consider leaving a rating and sharing this podcast with your colleagues in the aviation community, as it can serve as a valuable resource for all those involved in the industry. Remember to subscribe for more insights at PassiveIncomePilots.com! https://passiveincomepilots.com/  Join our growing community on Facebook: https://www.facebook.com/groups/passivepilots Check us out on Instagram @PassiveIncomePilots: https://www.instagram.com/passiveincomepilots/ Follow us on X @IncomePilots: https://twitter.com/IncomePilots 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* 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.

    48 min
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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 seasoned pilot or just starting out, we'll equip you with the expertise and confidence you need to upgrade your money and achieve true financial independence.

Información

  • Creador
    Tait Duryea and Ryan Gibson
  • Años de actividad
    2023 - 2026
  • Episodios
    146
  • Clasificación
    Apto
  • Copyright
    © 2024 Passive Income Pilots
  • Mostrar sitio web
    Passive Income Pilots

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