Passive Income Pilots

Tait Duryea and Ryan Gibson sit down with Money Insights wealth strategists Brenyn McConnell and Blake Brogan to explore how pilots can create more tax-efficient retirement income beyond a traditional 401(k). They break down how properly structured whole life insurance can provide liquidity, tax-free access to cash value, long-term care benefits, and estate-planning flexibility. Discover how this strategy can complement Roth conversions and alternative investments while helping high-income pilots reduce their dependence on taxable retirement accounts and build greater financial flexibility for the years ahead.Brenyn McConnell and Blake Brogan are Wealth Strategists at Money Insights, where they help high-income professionals build more efficient wealth strategies using high-cash-value life insurance and alternative investments. Brenyn has worked in financial services since 2018, while Blake brings roughly a decade of industry experience focused largely on overfunded life insurance strategies. They teach how properly structured policies can support tax-free retirement income, long-term care planning, liquidity, and generational wealth.Show notes:(0:00) Intro(0:13) Diversifying beyond the traditional 401(k)(7:20) The 401(k) retirement tax problem(11:12) Roth conversions and tax planning(14:24) Creating tax-free policy income(17:09) $2.5M cash value example(21:55) Accessing money before retirement age(23:49) Life insurance as a vehicle(25:13) Designing a self-sustaining policy(26:58) Avoiding poorly designed policies(29:24) Planning for long-term care(35:26) Estate and wealth-transfer planning(41:46) OutroConnect with Brenyn McConell & Blake Brogan:Website: https://insights.moneyinsightsgroup.com/pilots Related Episode:#47 - Innovative Wealth Strategies and Alternative Investing with Christian Allen and Rod ZabriskieIf 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.

Tait Duryea and Ryan Gibson close out the Passive Income Pilots Conference with a rapid-fire Q&A alongside experts Koy Harris, David Vanlandingham, Kurt Harris, and Adam Kintigh. Drawing on their expertise in estate planning, asset protection, business structuring, and tax strategies, the panel answers real-world questions about self-storage investing, tax withholding, privacy trusts, cost segregation, retirement conversions, and depreciation recapture. Pilots and high-income professionals will gain a clearer understanding of how to structure investments, protect real estate assets, avoid costly tax mistakes, and evaluate opportunities to generate passive income without adding unnecessary responsibilities to their already demanding careers.Show notes:(0:00) Intro(3:27) Self-storage market outlook(6:56) House hacking and privacy trusts(7:34) Managing tax withholding strategically(12:20) Replacing captain pay passively(13:16) Homestead and privacy trusts(16:10) Cost segregation on older rentals(17:00) Investing without active real estate(17:49) Naming trusts for asset privacy(21:41) Leveraging paid-off rental properties(27:28) Using real estate professional status(32:28) 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.

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.

Tait Duryea and Ryan Gibson sit down with veteran passive investor Jeremy Roll to discuss building wealth beyond traditional stocks and 401(k)s. Jeremy shares how more than two decades of alternative investing shaped his approach to market cycles, diversification, liquidity, and passive cash flow. They also discuss preparing for market corrections, creating life-changing income through a “get rich slow” strategy, tax advantages of alternative investments, and managing dozens of K-1s. For pilots looking to build additional income without relying entirely on the stock market, this episode offers a long-term investor’s perspective.Jeremy Roll is the Founder and President of Roll Investment Group and a longtime passive investor in real estate and private businesses. Before becoming a full-time investor, he spent more than a decade in the corporate world, including roles at Disney and Toyota, and earned his MBA from The Wharton School. Jeremy is also a co-founder of For Investors By Investors (FIBI), a nonprofit investor education and networking community. Known for his disciplined, research-driven approach, he has participated in more than 200 managed investments over his investing career.Show notes:(0:00) Intro(2:28) Jeremy Roll’s investing background(4:21) Investing through market cycles(7:21) Preparing for a market correction(11:43) Market concentration and margin debt(16:34) Diversifying beyond the 401(k)(18:59) Building life-changing passive income(23:38) The get rich slow strategy(26:30) Tax advantages of alternatives(30:44) Where Jeremy is investing today(33:35) Managing multiple K-1s(37:18) OutroConnect with Jeremy Roll:Email: [email protected] LinkedIn: linkedin.com/in/jeremy-roll-655107 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.

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.