Passive Income Pilots

Tait Duryea and Ryan Gibson host a live Q&A with Adam Kintigh, Kurt Harris, and David Vanlandingham covering the financial questions pilots face as their income and investments grow. From short-term rental tax strategies and Roth conversions to self-directed IRAs, 401(k) contributions, real estate leverage, and estate planning, the panel examines how different pieces of a wealth plan fit together. Pilots will leave with practical guidance on deploying capital more efficiently while balancing tax savings, liquidity, retirement planning, and long-term financial freedom.Show notes:(0:00) Intro(1:56) Where to hold investment cash(3:26) STR depreciation recapture strategies(5:57) Moving beyond a scarcity mindset(8:18) Short-term rental tax qualification(11:58) When passive income becomes enough(14:49) Traditional-to-Roth conversion strategies(18:45) Choosing cash versus retirement funds(23:12) Optimizing pilot 401(k) contributions(32:28) Financing short-term rental properties(36:43) Avoiding major estate planning mistakes(45:31) OutroIf 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/passivepilotsCheck us out on Instagram @PassiveIncomePilots: https://www.instagram.com/passiveincomepilots/Follow us on X @IncomePilots: https://twitter.com/IncomePilotsGet 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 [email protected] 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.

Join us on October 8–9, 2026, in Las Vegas, Nevada, for the first-ever Passive Income Pilots Conference. Learn how to build smarter wealth beyond the cockpit: https://www.passiveincomepilots.com/pip-conference Tait Duryea and Ryan Gibson examine the side of real estate investing that spreadsheets often miss, the return on life. Drawing from their own experiences with rental properties, they discuss when active ownership is worth the time, why so-called passive investments can start to feel like another job, and how pilots should think about short-term rentals beyond the tax benefits. They also cover cost segregation, bonus depreciation, depreciation recapture, 1031 exchanges, and why buying assets you are comfortable holding long term can matter. For pilots focused on tax efficiency and financial independence, this episode offers a practical look at what real estate ownership can actually require.Show notes:(0:00) Passive Income Pilots Conference announcement: https://www.passiveincomepilots.com/pip-conference (0:54) Reality of active real estate investing(2:24) Measuring your return on life(6:50) Tait’s costly multifamily lesson(11:10) Moving from active to passive investing(13:24) Short-term rentals and tax benefits(14:51) Grade the deal and lifestyle(19:56) Short-term rentals are hospitality businesses(24:28) Cost segregation and CPA planning(28:43) Depreciation recapture when selling(32:37) Buying assets for long-term wealth(37:54) OutroRelated Episodes:#32 - Tax Savvy Investing: The Power of Cost Segregation with Yonah Weiss#85 - Cost Segregation: The Tax Strategy You Can’t Afford to Ignore with Erik Oliver#144 - Depreciation, Cost Segs, and the IRS Rules Pilots Miss with Brandon Hall#145 - Bonus Depreciation & Cost Seg: The Tax Strategy Pilots Can’t Ignore with Gian PazziaBook Reference:Optimize YOUR BnbIf 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/passivepilotsCheck us out on Instagram @PassiveIncomePilots: https://www.instagram.com/passiveincomepilots/Follow us on X @IncomePilots: https://twitter.com/IncomePilotsGet 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 [email protected] 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.

Join us on October 8–9, 2026, in Las Vegas, Nevada for the first-ever Passive Income Pilots Conference. Learn how to build smarter wealth beyond the cockpit: https://www.passiveincomepilots.com/pip-conference Tait Duryea welcomes Chris Naugle to discuss his unconventional path from professional snowboarding and Wall Street to real estate and privatized banking. Chris shares lessons from building businesses, surviving financial setbacks, owning dozens of rental units, and completing hundreds of flips before discovering the Infinite Banking Concept. They examine how specially designed whole life policies can support private lending, real estate investing, debt strategies, and greater control over capital while highlighting the discipline required to make the strategy work.Chris Naugle is a wealth educator, entrepreneur, real estate investor, and former registered investment advisor specializing in privatized banking and the Infinite Banking Concept. A former professional snowboarder, Chris built multiple businesses before moving into financial services, real estate investing, and private lending. His experience includes managing investment assets, completing hundreds of house flips, appearing on HGTV’s Risky Builders, and building systems designed to help investors take greater control of their capital. Show notes:(0:00) Passive Income Pilots Conference announcement: https://www.passiveincomepilots.com/pip-conference (8:00) Chris Naugle’s wealth-building journey(13:54) Building a business at seventeen(18:31) Transition from retail to Wall Street(26:32) Building a financial advisory career(29:24) First lessons in real estate(36:20) Hitting the real estate debt wall(41:51) From house flipping to HGTV(44:05) Discovering privatized banking(49:06) Rethinking traditional money strategies(51:30) Infinite banking versus securities-backed credit(57:25) OutroConnect with Chris Naugle:Website: https://www.chrisnaugle.com/ LinkedIn: https://www.linkedin.com/in/thechrisnaugle/ YouTube: https://www.youtube.com/thechrisnaugle 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/passivepilotsCheck us out on Instagram @PassiveIncomePilots: https://www.instagram.com/passiveincomepilots/Follow us on X @IncomePilots: https://twitter.com/IncomePilotsGet 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 [email protected] 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.