Passive Income Pilots

Tait Duryea and Ryan Gibson
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  • Chaque semaine

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. -4 j

    #159 - How Deferred Sales Trusts Work with Trevor Kuresa

    Tait Duryea and Ryan Gibson sit down with Trevor Kuresa to unpack the Deferred Sales Trust, a lesser-known strategy for deferring capital gains after selling a business or highly appreciated asset. Trevor explains how the structure works, why it differs from a 1031 exchange or monetized installment sale, and when the costs, timing, and compliance rules make sense. For pilots, real estate investors, and business owners thinking about a future exit, this episode offers a practical look at tax planning before a major transaction. Trevor Kuresa is a corporate and tax attorney specializing in mergers and acquisitions, fractional general counsel, and advanced tax strategies for business owners and high-income professionals. With experience in tax structuring, legal transactions, and corporate counsel work, Trevor helps clients evaluate strategies for reducing or deferring capital gains and income tax. Show notes: (0:00) Chamonix race recap (2:14) Deferred Sales Trust intro (4:47) Trevor’s legal background (6:10) Tax strategy for pilots (9:37) Deferred sales trust explained (13:50) Rental property example (17:26) Best use cases (21:10) Tax deferral mechanics (25:15) IRS rules and risks (36:28) Outro Connect with Trevor: Website: https://hibiscuslegal.com/ Email: tkuresa@hibiscuslegal.com Phone: 801-577-3445LinkedIn: https://www.linkedin.com/in/trevor-kuresa-36b59339/  Related Episode:  #10 - Reduce Your Taxes & Maximize Returns Using PROVEN Investment Strategies with Toby Mathis 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.

    37 min

  2. 24 juin

    #158 - Why the 10-30-30-30 Strategy Could Change How Pilots Invest

    Is your wealth strategy working together or pulling in different directions? Hosts Tait Duryea and Ryan Gibson unpack the 10-30-30-30 strategy for balancing cash, 401(k)s, real estate, tax benefits, and passive investments. They explain why liquidity, control, and tax strategy all matter, and how short-term rentals, syndications, oil and gas, and self-storage can fit into a pilot’s portfolio. Plus, they preview Passive Income Pilots Live in Las Vegas, a new event focused on financial education, estate planning, due diligence, and community. Show notes: (0:00)  Intro (2:15) Diversifying pilot investments (3:33) The 10-30-30-30 strategy (7:23) Managed money and 401(k)s (9:21) 2026 401(k) limits (12:14) Tax-advantaged real estate (15:06) Short-term rental episodes (16:50) Passive investments and syndications (18:13) Oil and gas tax benefits (26:51) Passive Income Pilots Live (29:52) Outro Related Episodes:  #87 - The Mega Backdoor Roth and How Pilots Can Maximize Retirement Contributions with Timothy Pope#14 - Depreciation Demystified: Cost Segregation and Tax Savings in Real Estate with Toby Mathis#37 - Empowering Insights and Strategies On Short-Term Rentals with Alex Jarbo#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 Event Mentioned: Passive Income Pilots Live Conference - Location: Las Vegas, Dates: October 8–9. For updates on tickets and details, keep an eye out for the official announcement from Passive Income Pilots. 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.

    30 min

  3. 16 juin

    #157 - Who Gets Paid First? How Real Estate Deals Are Actually Structured

    Tait Duryea and Ryan Gibson break down one of the most important but often misunderstood parts of real estate investing: the capital stack. They explain how senior debt, mezzanine debt, preferred equity, and common equity shape risk, returns, and who gets paid first. For pilots and high-income professionals evaluating passive income opportunities, this episode offers a practical framework for understanding leverage, deal structure, DSCR, private credit, and why projected returns do not tell the whole story. Show notes: (0:00) Intro (1:10) Ways investors get paid (3:08) Capital stack basics (4:11) Debt drives real estate risk (7:32) All-cash versus leveraged deals (10:31) Common equity explained (18:50) Preferred equity position (21:10) Checking debt ahead (27:39) Rescue capital versus healthy deals (35:36) Operator view on structure (42:05) DSCR and cash flow cushion (57:18) Outro Related Episode:  #2 - Invest Passively in DST and Opportunity Zones with Brandon Bruckman 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.

    57 min

  4. 20 mai

    #156 - From Active Deals to Passive Income with Chris Prefontaine

    Tait Duryea and Ryan Gibson welcome back Chris Prefontaine for a practical conversation on active investing, creative deal structures, and using real estate to build capital for future passive income. Built for pilots and high-income professionals, this episode looks at what it takes to move beyond simply writing checks into deals and start understanding how opportunities are created. Chris brings a seasoned perspective on today’s market, traditional bank limits, and the skills investors need before getting more hands-on. If you have ever wondered whether active real estate could help fuel your long-term wealth strategy, this episode is worth your attention. Chris Prefontaine is the Chairman and Founder of Smart Real Estate Coach®, a best-selling author, and host of the Smart Real Estate Coach® Podcast. With nearly 35 years in the industry, Chris has helped investors better understand creative real estate strategies through changing market cycles. His work gives listeners a practical look at how experience, education, and smart deal structure can shape a more resilient investing path. Show notes: (0:00)  Intro (0:44) Active income to passive wealth (4:36) Chris’ real estate background (9:23) The three-payday strategy (11:51) First steps for active investors (16:44) Creative financing trends (19:04) What does creative financing mean (23:28) Personal guarantee risks (27:03) Buying short-term rentals (33:03) Outro Connect with Chris: Website: https://3paydaysbooks.com/pip LinkedIn: https://www.linkedin.com/in/chrisprefontaine/  Related Episode:  #97 - Creative Deal Structuring: Smart Real Estate Strategies with Chris Prefontaine 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.

    33 min

  5. 13 mai

    #155 - The New Reality of Aviation Hiring with Nik Fialka

    What happens when the aviation job market shifts faster than pilots are prepared for? Live from TPNX in Dallas, Tait Duryea sits down with Nik Fialka for a timely look at pilot hiring, airline interviews, and career strategy in a changing aviation market. From major airline hiring trends to the pressure facing Spirit and regional pilots, this episode gives pilots and aviation families a clearer view of what is shifting, what still matters, and why preparation can make or break the next opportunity. If you know an aspiring pilot, military transition pilot, regional pilot, or airline hopeful, this is the conversation to send them before the next interview window opens. Nik Fialka is a major airline pilot, former U.S. Navy pilot, aviation mentor, and host of Ready 4 Pushback. As part of Spitfire Elite, he helps pilots prepare for high-stakes airline interviews with a focus on confidence, communication, leadership, and cultural fit. With experience across military aviation, airline operations, and pilot coaching, Nik brings a practical, no-fluff perspective to the career decisions that shape a pilot’s future. His work supports aviators from flight training to major airline interviews and beyond. Show notes: (0:00)  Intro (1:48) Nick’s aviation background (3:36) Inside Spitfire Elite (5:11) Why interview prep matters (7:08) Authentic interview answers (8:49) Ready for Pushback podcast (12:13) State of aviation hiring (18:04) Major airline hiring numbers (19:37) Advice for Spirit pilots (22:59) Standing out beyond flight time (27:16) Outro Connect with Nik Fialka: Website: https://spitfireelite.com/ Email: podcast@spitfireelite.com LinkedIn: https://www.linkedin.com/in/sir-nik-fialka-86b16515/  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.

    27 min

  6. 28 avr.

    #154 - The Pilot’s Guide to SDIRA Tax Traps with Mark Kohler

    Tait Duryea and Ryan Gibson welcome back Mark Kohler to unpack one of the most misunderstood topics in self-directed IRA investing: UBIT and UDFI. Mark explains how these taxes show up in real estate syndications, why leverage can trigger tax inside an IRA, when C corp blockers may help, and what pilots should watch for on K-1s and 990-T filings. This episode gives high-income professionals a clearer way to evaluate SDIRA deals without letting tax fear cloud the bigger investment picture. Mark Kohler is a CPA, attorney, tax strategist, and longtime advocate for small business owners and investors. With decades of experience in tax law, entity structuring, retirement planning, and asset protection, Mark is known for making complex tax strategies easier to understand and apply. He brings practical clarity to the rules that affect pilots and high-income professionals using retirement dollars to invest beyond Wall Street. Show notes: (0:00)  Intro (0:48) UBIT and self-directed IRAs (4:32) Understanding UBIT, UDFI, and 990-Ts (5:36) Why UBIT exists (10:05) How C Corp blockers work (14:37) Reading K-1 warning signs (18:57) How leverage creates UDFI (23:09) Comparing SDIRA and cash investors (31:18) Trust tax rates explained (37:41) When IRAs need an EIN (41:37) Real numbers on UDFI taxes (55:30) Outro Connect with Mark: Website: https://markjkohler.com/ LinkedIn: https://www.linkedin.com/in/markjkohler/  Related Episodes:  #110 - The IRA Club Advantage: The Self-Directed IRA Strategy for Pilots with Ramez Fakhoury#36 - Decoding the Untapped Potential and Complex World of Self-Directed IRAs with Derreck Long#82 - From LLCs and HSAs to Roth IRAs: Mastering Wealth Protection with Mark Kohler 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.

    56 min

  7. 14 avr.

    #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

  8. 7 avr.

    #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
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À propos

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.

Informations

  • Création
    Tait Duryea and Ryan Gibson
  • Années d’activité
    2023 - 2026
  • Épisodes
    158
  • Classification
    Tous publics
  • Copyright
    © 2024 Passive Income Pilots
  • Site web de l’émission
    Passive Income Pilots

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