Passive Income Pilots

Tait Duryea and Ryan Gibson
  • 4.9 (106)
  • INVESTING
  • UPDATED WEEKLY
Passive Income Pilots

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. 21 HR. AGO

    #98 - The Right Coverage: Property Insurance Strategies with Valerie Cusano

    In this episode of Passive Income Pilots, Tait Duryea and Ryan Gibson sit down with Valerie Cusano, an insurance expert with a background in law and decades of experience in commercial and residential insurance. Val dives deep into the critical aspects of real estate insurance, particularly for condo and rental property owners. She explains the difference between condo and homeowners insurance, key policy coverages investors should have, and how to evaluate a building’s financial health before buying in. The conversation also touches on industry trends, the role of insurance brokers, and how global factors impact insurance rates. Valerie Cusano is a seasoned insurance expert with decades of experience in the industry. Originally a lawyer specializing in insurance defense, she transitioned into brokering and eventually founded her own insurance agency. Val has extensive commercial and residential insurance expertise, including coverage for high-net-worth individuals and real estate investors. In this episode, Val breaks down essential insurance strategies for pilots and investors, covering everything from policy selection to risk management. Show notes: (0:00) Intro (03:09) Val’s background in law & insurance (04:46) Key insurance considerations for rental properties (07:18) Condo insurance vs. homeowners insurance (08:57) Red flags when investing in condos (12:41) The benefits of condo ownership (18:48) Understanding global insurance markets & rising rates (25:40) How to ensure your condo board gets the best rates (36:29) How to find the right insurance broker (45:49) Essential insurance coverages every investor needs (48:55) Outro Connect with Valerie Cusano: LinkedIn: https://www.linkedin.com/in/valerie-cusano-92290717/  Website: https://palm.global/canada/people  — 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.

    50 min

  2. FEB 11

    #97 - Creative Deal Structuring: Smart Real Estate Strategies with Chris Prefontaine

    In this episode, Tait Duryea and Ryan Gibson dive into creative real estate financing with Chris Prefontaine, founder of Smart Real Estate Coach. Chris shares powerful strategies like seller financing, subject-to deals, and lease purchases, revealing how investors can acquire properties without banks—even in today’s high-interest rate environment. Learn how to find off-market properties, negotiate seller carrybacks, and unlock hidden real estate opportunities. Chris Prefontaine is the chairman and founder of Smart Real Estate Coach, with over 30 years of experience in the real estate industry. Since 1991, he has built, brokered, and invested in properties across various asset classes. After weathering the 2008 financial crash, he shifted his focus to creative financing strategies, specializing in seller financing, lease purchases, and subject-to deals. Through Smart Real Estate Coach, Chris mentors investors across North America, helping them structure profitable real estate transactions without relying on banks.  Show notes: (0:00) Intro (06:21) What is seller financing? (10:26) Why sellers agree to carry the note—the hidden tax benefits (19:41) Seller vs. buyer perspective (24:19) How to find free-and-clear properties for seller financing (38:02) The key to negotiating seller financing terms (44:00) What is a Subject-To (Sub-To) deal? (49:18) How to invest passively vs. actively in real estate (52:29) Outro Connect with Chris Prefontaine: LinkedIn: https://www.linkedin.com/in/chrisprefontaine Website: https://wickedsmartbooks.com/PIP  — 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.

    53 min

  3. FEB 4

    #96 - Airplane Write-Offs, IRS Audits, and Smart Tax Planning with Ryan DeMoor

    Have you ever wondered how you could write off an airplane? In this episode, Ryan DeMoor joins hosts Tait Duryea and Ryan Gibson to break down the tax benefits of aircraft ownership. Ryan shares how pilots and business owners can strategically use aircraft purchases for tax deductions, the IRS rules around business use, and why proper record-keeping is critical for audits. Whether you're considering buying a Cessna or a Gulfstream, this episode is packed with insights on bonus depreciation, IRS audits, 1031 exchanges, and passive vs. active use of an aircraft. Ryan DeMoor is an aviation tax and finance expert specializing in corporate and private aircraft ownership structures. As the head of aviation tax at MySky, a Swiss-based aviation financial technology company, and the Chair of the NBAA Tax Committee, Ryan helps high-net-worth individuals and corporations navigate tax-efficient aircraft ownership, compliance, and financial structuring. A former pilot with over a decade of flying experience, Ryan brings a unique perspective on how aviators can strategically leverage aircraft for business use while staying compliant with IRS regulations. Show notes: (0:00) Intro (06:04) How pilots can buy an airplane tax-efficiently (08:35) Examples of using an aircraft for business (13:29) IRS rules for business vs. personal aircraft use (22:21) Why IRS audits on aircraft ownership are increasing (28:08) The 25% business use rule and tax recapture risks (30:42) 1031 exchanges for aircraft—what changed? (38:40) Passive vs. active aircraft ownership and tax implications (44:46) The most insane aircraft tax write-off ever (49:08) Outro Connect with Ryan DeMoor: LinkedIn: https://www.linkedin.com/in/ryan-demoor-cam-mba/details/experience/ Website: https://mysky.com/ Email: Ryan@MySky.comNBAA (National Business Aviation Association): https://nbaa.orgAOPA (Aircraft Owners and Pilots Association): https://www.aopa.org — 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.

    50 min

  4. JAN 28

    #95 - Franchise Investing 101: Insights and Opportunities with Cliff Nonnenmacher

    In this episode of Passive Income Pilots, hosts Tait Duryea and Ryan Gibson explore the world of franchise ownership with franchise expert Cliff Nonnenmacher. Cliff brings decades of experience as a franchise consultant and serial entrepreneur, sharing insights into how pilots and professionals can invest in or operate franchises to build wealth. The discussion covers everything from initial franchise fees to evaluating opportunities, scaling businesses, and emerging non-brick-and-mortar trends. Whether you’re considering a side hustle or a full-time business, Cliff provides actionable advice tailored to high-income professionals seeking financial independence. Cliff Nonnenmacher is a veteran entrepreneur and franchise consultant with over 20 years of experience in franchise ownership, business scaling, and investment strategies. A former investment banker, Cliff has managed multi-million-dollar ventures and specializes in helping professionals transition into franchise ownership. He provides guidance on selecting, funding, and operating franchises that align with personal goals, making him a trusted resource for aspiring business owners. Show notes: (0:00) Intro (3:30) Meet Cliff Nonenmacher: Franchise expert (9:25) History of franchising and its business models (15:05) Breaking down franchise fees and royalties (21:44) What makes a successful franchisee (26:38) Cliff’s free consulting services explained (32:40) Buying a franchise: Existing vs. new (39:51) Non-brick-and-mortar franchise trends (50:38) Surprising revenue potential of service-based franchises (53:50) Outro Connect with Cliff Nonnenmacher: LinkedIn: https://www.linkedin.com/in/cliffnonnenmacher Website: http://www.franocity.com Email: cliffn@franocity.comPodcast: Pursuit of Profit (featuring franchise founders)- https://franocity.com/pursuit-of-profit-podcast/ — 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.

    54 min

  5. JAN 21

    #94 - Fail Fast, Succeed Faster: Wealth-Building and Investment Strategies with Christian Schiller

    In this episode, Tait Duryea and Ryan Gibson sit down with Christian Schiller, an accomplished investment banker with a wealth of experience buying, selling, and evaluating businesses. Christian shares his investment journey, including lessons from early failures, how he refined his investment strategy, and why knowing your limits is key to success. He breaks down the role of investment bankers, explains how pilots and high-income professionals can benefit from understanding private equity and alternative investments, and emphasizes the importance of building a strong network. Whether you're interested in public markets, private equity, real estate, or improving your financial strategy, this episode is packed with actionable advice and insights tailored to investors at all levels. Christian Schiller is a seasoned investment banker and Managing Director at Cascadia Capital, specializing in helping clients buy, sell, and evaluate businesses. With over two decades of experience, Christian has developed a keen eye for identifying opportunities and building strategic relationships in the investment world. A proponent of "know, like, trust" as the foundation of investing, Christian has refined his personal investment philosophy through a mix of private equity, venture capital, and operating company investments. Beyond his professional achievements, Christian is an avid traveler, family man, and advocate for a well-balanced life. Show notes: (0:00) Intro (0:56) Christian’s early investment failures (2:15) What investment bankers do and why it matters to pilots (4:15) Christian’s philosophy on prioritization and life balance (9:59) Key lessons from evaluating businesses (15:42) Learning from failures: 26 out of 27 investments gone wrong (19:25) "Know, like, trust" as a personal investment strategy (26:30) Investing in operating companies vs. real estate (32:25) Finding wealth managers with alternative investment access (43:19) Favorite ways to generate passive income (45:45) Outro Connect with Christian Schiller: LinkedIn: https://www.linkedin.com/in/christianeschiller Email: cschiller@cascadiacapital.com — 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

  6. JAN 14

    #93 - Stock Market Insights and Tax Strategies for High-Income Earners with Brian Feroldi

    In this episode, Tait Duryea and Ryan Gibson welcome Brian Feroldi, author of Why Does the Stock Market Go Up? to unpack the fundamentals of the stock market and explain strategies tailored for pilots and high-income professionals. Brian demystifies the difference between Roth and traditional 401(k) contributions, shares insights into dividend investing, and explains how to identify great companies for long-term growth. He also offers advice on working with financial advisors and highlights why most investors are better off with index funds. Whether you’re new to investing or looking to refine your strategy, this episode is packed with actionable insights. Brian Feroldi is a stock market expert, author, and financial educator who has been investing since he was 19. Known for his straightforward approach to financial literacy, Brian wrote Why Does the Stock Market Go Up? Everything You Should Have Been Taught About Investing in School, But Weren’t, a guide for beginners looking to understand the stock market and build wealth. With a passion for analyzing businesses and empowering individuals to make smarter financial decisions, Brian helps professionals navigate everything from 401(k)s to stock picking, while debunking myths about investing. Show notes: (0:00) Intro (01:20) Q & A: Roth vs. traditional 401(k) tax strategies for pilots (10:24) Brian’s journey from gambling to investing in stocks (16:55) How the stock market works: An investor's perspective (24:55) What an overvalued stock market means (29:40) Brian’s stock analysis checklist: What to look for in a business (36:13) Tax-loss harvesting explained (40:30) Should you hire an advisor for your 401(k)? (45:50) Diversification beyond stocks: Brian’s personal portfolio philosophy (49:06) Volatility vs risk (52:10) Key takeaways from Brian’s book Why Does the Stock Market Go Up? (54:42) Outro Connect with Brian Feroldi: Book: Why Does the Stock Market Go Up? - https://amzn.to/40w3lfJ Youtube: https://www.youtube.com/c/BrianFeroldiYTX: https://x.com/BrianFeroldi Instagram: https://www.instagram.com/brianferoldi Facebook: https://www.facebook.com/brian.feroldi — 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.

    55 min

  7. JAN 7

    #92 - Opportunity Zones for Passive Income: Unlock Tax Savings and Growth with Nathan Sosa

    Dive into the intricacies of Opportunity Zones with this episode of Passive Income Pilots. Hosts Tait Duryea and Ryan Gibson are joined by CPA Nathan Sosa of Hall CPA, who demystifies Opportunity Zone (OZ) investments and their potential for tax deferral and appreciation. Whether you're an active investor or prefer passive opportunities, learn how OZs can defer taxes on gains from stocks, businesses, or real estate, and how they compare to other tax strategies like 1031 exchanges. Nathan explains the steps, requirements, and benefits, all while offering actionable insights tailored to high-income earners, especially pilots. Nathan Sosa is a Certified Public Accountant (CPA) with Hall CPA, a firm specializing in real estate tax strategy. As a seasoned tax strategist, Nathan works closely with high-income professionals and investors to navigate complex tax codes and optimize financial outcomes. With expertise in Opportunity Zones, real estate syndications, and tax planning, Nathan empowers clients with proactive strategies to minimize tax liabilities and build wealth. Show notes: (0:00) Intro (3:45) Why OZs matter for tax deferral (5:35) Hands-off investing in Opportunity Zones (7:16) What qualifies as a capital gain? (9:49) The difference between OZ boundaries and OZ funds (16:25) IRS requirements for OZ investments (27:30) Doubling basis and the 10-year hold explained (31:04) Depreciation recapture benefits in OZs (49:45) Connecting with Hall CPA (51:00) Outro Related Episode: #75 - Unlocking Real Estate Professional Status (REPS) with Brandon Hall Connect with Nathan Sosa: Book a Discovery Call with Nathan Sosa: https://bit.ly/HallCPA  — 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.

    51 min

  8. 12/31/2024

    #91 - Interest Rates, Submarkets, and CRE's Future with Spencer Levy

    Spencer Levy, a leading expert from CBRE, joins Tait Duryea and Ryan Gibson to break down the current state of commercial real estate (CRE). He explains how rapid interest rate changes are reshaping the market, highlights key megatrends like reshoring and live-work-play neighborhoods, and offers advice on navigating submarkets. Whether you’re a seasoned investor or just getting started, Spencer shares valuable strategies to help pilots and high-income professionals make smarter CRE investments. Learn to identify undervalued opportunities and position yourself for success in a shifting landscape. Spencer Levy is the Senior Economic Advisor and Global Client Strategist at CBRE, where he helps the world’s largest investors and occupiers navigate commercial real estate trends. Known for his dynamic speaking style and expert analysis, Spencer advises on investment strategies and market forecasts, delivering over 120 presentations annually. As the host of The Weekly Take podcast, he offers in-depth insights on everything from macroeconomic trends to niche submarkets, making him a leading voice in the CRE industry. Show notes: (0:00) Intro (4:46) Spencer shares his CBRE role and focus (7:09) Key macro trends in commercial real estate (11:22) Interest rates' impact on CRE markets (16:25) The case for a potential office market rebound (31:31) Identifying submarkets for investment success (43:39) Reshoring manufacturing and its CRE implications (46:01) Advice and resources for new CRE investors (48:11) Spencer’s optimism for CRE recovery and trends (48:40) Outro Connect with Spencer Levy: Website: https://www.cbre.com/people/spencer-levy LinkedIn: https://www.linkedin.com/public-profile/in/spencerglevy X: https://twitter.com/SpencerGLevy Podcast: https://www.cbre.com/insights/the-weekly-take   — 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.

    49 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 - 2025
  • Episodes
    98
  • Rating
    Clean
  • Copyright
    © 2024 Passive Income Pilots
  • Show Website
    Passive Income Pilots

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