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. 6 DAYS AGO

    #153 - Tax Moves Every Pilot Should Know with Nathan Sosa

    How much money are you leaving on the table by waiting until tax season to start planning? Hosts Tait Duryea and Ryan Gibson talk with Nathan Sosa from Hall CPA to break down the latest tax updates that matter most to pilots and high-income professionals. Get ready to hear practical insights on bonus depreciation, the short-term rental strategy, oil and gas tax benefits, passive real estate losses, and why filing an extension may be smarter than rushing to file. They also clear up common confusion around K-1s and explain when it makes sense to bring in a CPA. Nathan Sosa is a tax strategist at Hall CPA with a master’s in taxation and deep expertise in helping high-income earners, including pilots, navigate complex tax planning. His advice helps investors think ahead, avoid costly mistakes, and make smarter tax decisions. Show notes: (0:00)  Intro (0:43) Meet tax strategist Nathan Sosa (4:27) State of the tax world (5:00) Bonus depreciation back to 100% (8:03) Net investment income tax explained (12:01) SALT deduction surprises and limits (15:08) Bunching charitable deductions strategy (17:13) Short-term rental tax strategy (20:28) Oil and gas tax benefits (31:23) What happens when deals sell (42:59) Extensions, amendments, and late K-1s (49:16) Outro Connect with Nathan Sosa: Website: https://www.therealestatecpa.com/become-client/ LinkedIn: https://www.linkedin.com/in/nathansosacpa/  Related Episodes:  #14 - Depreciation Demystified: Cost Segregation and Tax Savings in Real Estate with Toby Mathis#92 - Opportunity Zones for Passive Income: Unlock Tax Savings and Growth with Nathan Sosa#118 - The Big Beautiful Tax Bill with Nathan Sosa 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.

    49 min

  2. 7 APR

    #152 - Free Estate Planning and a Hidden Tax Strategy with Jenny Spradling

    Tait Duryea and Ryan Gibson sit down with Jenny Spradling, co-founder of FreeWill, to explore how estate planning can be simpler, faster, and even free. Jenny explains why millions of Americans still lack basic estate documents and how that creates major complications for families. The conversation breaks down probate, wills vs. trusts, and why both are often needed. They also uncover powerful strategies around charitable giving, including how donating appreciated assets like stock or crypto can dramatically increase tax efficiency while maximizing impact. This episode offers practical insights for pilots and high-income professionals thinking about legacy, taxes, and protecting their wealth. Jenny Spradling is the co-founder and co-CEO of FreeWill, a platform that provides free estate planning tools to individuals across all 50 U.S. states. A serial entrepreneur focused on financial access, Jenny previously founded Paribus, a consumer fintech startup. Through FreeWill, she has helped over 1.4 million people create estate plans and facilitated nearly $14 billion in charitable bequests. Her work focuses on making estate planning simple, accessible, and integrated with modern giving strategies. Show notes: (0:00)  Intro (3:22) Jenny Spradling’s entrepreneurial background (6:56) Why people include charity in estate plans (11:34) Understanding probate and why it matters (13:30) State differences in estate planning laws (16:44) What happens when you die intestate (20:22) Why trusts still need a will (24:24) When to use online estate planning vs attorneys (31:10) How to start thinking about charitable giving (44:15) Major tax advantages of donating stock (47:55) Outro Connect with Jenny: Website: https://www.freewill.com/ Email: Jenny@freewill.com LinkedIn: https://www.linkedin.com/in/jenxia/  Related Episodes:  #114 - Trusts, Taxes & Transfers: What Every Investor Should Know with Amanda Wynalda#127 - LLCs, Trusts, and K-1s: Smarter Asset Protection with Adam Kintigh#137 - Revocable Vs. Irrevocable Trusts: What Pilots Must Know with Adam Kintigh 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.

    48 min

  3. 2 APR

    #151 - Debt, AI, and the Next Market Cycle with Guy Adami

    What happens when record debt, rising interest rates, and AI disruption collide in the global economy? Hosts Tait Duryea and Ryan Gibson welcome back market veteran Guy Adami to unpack the forces shaping today’s financial markets. From bond yields and inflation to the Buffett Indicator and AI’s impact on jobs, Guy offers a behind-the-scenes look at what professional investors are watching right now. The conversation explores why the market feels strong even while many stocks are down sharply, how passive investing has reshaped valuations, and why global debt and currency devaluation may become defining issues for the next decade. For pilots and high-income professionals building wealth, the episode highlights the importance of understanding what you own, staying tactical in uncertain markets, and focusing on long-term asset ownership in an inflationary world.  Guy Adami is a veteran market strategist, hedge fund manager, and the longest-tenured host on CNBC’s Fast Money. With decades of experience analyzing global markets, macroeconomics, and equities, Guy is known for breaking down complex financial trends into practical insights investors can use. Show notes: (0:00)  Intro (03:12) Why market volatility is returning (04:32) Global bond yields driving market stress (06:07) The narrow market leadership problem (07:39) Buffett Indicator warning signals (10:38) How investors should approach markets (13:36) AI disruption and labor market risks (21:33) AI hype cycles and tech bubbles (31:04) Treasury auctions and global debt pressure (39:20) Tactical investing in uncertain markets (47:02) Outro Connect with Guy Adami: LinkedIn: https://www.linkedin.com/in/guy-adami-304618a/ Website: https://www.riskreversal.com/Youtube: https://www.youtube.com/@RiskReversalMedia  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.

    49 min

  4. 27 MAR

    #150 - From Listener to Investor with John Wahrmund

    Hosts Tait Duryea and Ryan Gibson sit down with First Officer at Southwest Airlines pilot John Wahrmund to unpack how one listener turned podcast advice into real results. John shares how episode 10 pushed him to buy a short-term rental in Galveston, unlock major tax savings, and rethink how his family builds wealth. This episode highlights intentional investing, knowing your market, using the right team, and why tax strategy can be a powerful tool for high-income professionals who want more freedom, options, and time. John Wahrmund is a Southwest Airlines pilot and retired Air Force officer who spent 20 years flying military aircraft before starting his airline career. In this episode, he shares how he used lessons from Passive Income Pilots to buy a short-term rental in Galveston, reduce his tax liability, and build a more intentional long-term wealth strategy for his family. His story brings a practical, real-world example of what happens when a listener takes action. Show notes: (0:00) Intro (0:56) John’s aviation background (2:08) Why he brought tax returns (6:25) An episode that sparked action (8:43) Why Galveston made sense (12:21) How the tax strategy works (15:09) Financing the first property (18:03) Tax savings over cash flow (21:51) Start with your real goal (30:24) Tech stack for remote hosting (36:06) Why the real win is time (40:02) Outro Connect with John Wahrmund: LinkedIn: linkedin.com/in/john-wahrmund-56151810 Email: johnwahrmund@gmail.com  Related Episodes: #10 - Reduce Your Taxes & Maximize Returns Using PROVEN Investment Strategies with Toby Mathis#23 - Counting the Cost: The Risks and Rewards of 401(k) Loans for Pilots#41 - Short-Term Rental Strategies To Maximize Your Passive Income with Dan Templin:#68 - Cruising to Success: Optimizing Your Short-Term Rentals with Airbnb Insider Daniel Rusteen#110 - The IRA Club Advantage: The Self-Directed IRA Strategy for Pilots with Ramez Fakhoury#137 - Revocable Vs. Irrevocable Trusts: What Pilots Must Know with Adam Kintigh 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.

    41 min

  5. 11 MAR

    #149 - Side Hustles Every Pilot Should Consider

    Hosts Tait Duryea and Ryan Gibson explore one of the most common questions among airline pilots: Should you start a side hustle? Drawing from Ryan’s early experience building income streams during layovers, the hosts share practical ideas pilots can pursue both inside and outside aviation. From consulting and drone photography to aircraft brokerage and real estate investing, they explain how extra income can become the fuel for long-term wealth building. They also discuss tax strategy, airline contract knowledge, and why passion matters when choosing a side hustle. If you’ve ever wondered how to turn extra time into opportunity, this episode offers plenty of ideas. Show notes: (0:00) Intro (1:03) Ryan’s first airline side hustle story (3:00) Turning layover time into opportunity (5:23) Why extra income matters for investing (6:30) Discipline and tax planning for side income (7:26) Using airline contracts to create free time (10:10) Aviation side hustle ideas explained (17:34) Helping pilots prepare for airline interviews (22:50) Non-aviation side hustles and real estate (30:53) Airline training and instructor opportunities (33:43) Outro Related Episode: #95 - Franchise Investing 101: Insights and Opportunities with Cliff Nonnenmacher 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.

    34 min

  6. 5 MAR

    #148 - Traditional Vs. Roth IRAs: What Pilots Need to Know

    Tait Duryea and Ryan Gibson break down one of the most important retirement decisions pilots face: Traditional vs. Roth IRAs. They explain how taxes impact withdrawals, why required minimum distributions matter, and how poor planning could leave your kids with a massive tax bill. The conversation also explores advanced strategies like Roth conversions, self-directed IRAs, and “Roth chunking” during low-income years. If you want to build wealth through real estate while protecting your retirement from unnecessary taxes, this episode offers practical frameworks to help pilots think long-term about their portfolio, income streams, and legacy planning. Show notes: (0:00) Intro (3:01) Traditional vs Roth fundamentals (7:30) Required minimum distributions explained (11:13) Nest egg vs golden goose investing (14:55) Using self-directed IRAs for real estate (21:37) Inherited IRA tax pitfalls (26:08) Roth chunking for new airline hires (30:58) Strategic Roth conversions during low-income years (35:11) Passive income to fund retirement (38:35) Advanced Roth conversion appraisal strategy (45:38) Outro Related Episode: #110 - The IRA Club Advantage: The Self-Directed IRA Strategy for Pilots with Ramez Fakhoury: https://passiveincomepilots.com/episode/110-the-ira-club-advantage-the-self-directed-ira-strategy-for-pilots-with-ramez-fakhoury 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.

    46 min

  7. 17 FEB

    #147 - From Cap Rates to Cash Flow: Strategic Moves for 2026

    Tait Duryea and Ryan Gibson sit down for a special hosts-only episode to break down where they see the biggest opportunities for 2026. From reshoring trends fueling industrial growth to the demographic wave driving senior living demand, they unpack the macro forces shaping real estate right now. They also explain why falling interest rates, reduced new construction, and renewed capital flows are creating a unique window for investors. Plus, they dive into debt funds, tax considerations, and why consistent cash flow can be a game-changer for high-income professionals looking to upgrade their money strategy. Show notes: (0:00) Intro (01:16) Announcing the 2026 Vegas conference (03:16) 2026 investment focus areas (04:18) Reshoring and industrial growth (08:25) Real estate cycle breakdown (12:52) Cap rate expansion explained (14:07) Self-storage supply trends (18:23) Senior living demand wave (21:48) Baby boomer wealth shift (29:27) Debt funds and cash flow (31:03) Tax strategy for debt investing (35:32) 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 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

    36 min

  8. 9 FEB

    #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
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About

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.

Information

  • Creator
    Tait Duryea and Ryan Gibson
  • Years Active
    2023 - 2026
  • Episodes
    153
  • Rating
    Clean
  • Copyright
    © 2024 Passive Income Pilots
  • Show Website
    Passive Income Pilots

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