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Passive Income Pilots

Passive Income Pilots

Written by: 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.

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Episodes
  • #142 - Tax Planning for W-2 Pilots Without Complex Businesses with Gary Heldt

    #142 - Tax Planning for W-2 Pilots Without Complex Businesses with Gary Heldt
    Jan 13 2026
    Are you paying for a high-powered CPA when your tax situation doesn’t actually require one?In this episode, Tait Duryea and Ryan Gibson sit down with CPA Gary Heldt to clarify what smart tax planning really looks like for high-income pilots with relatively simple financial lives. They break down how W-2 earners can optimize taxes without complex businesses, aggressive strategies, or unnecessary fees. Gary explains how often-overlooked fundamentals like benefits planning, estimated taxes, and coordinated advice can quietly compound into meaningful long-term gains. If you want clarity, confidence, and a more intentional approach to your CPA relationship, this episode delivers.Gary Heldt is a CPA, Certified Tax Coach, and founder of Small Business Advisors. With over 25 years of experience, he helps high-income professionals make better tax decisions through a consultative, family-office-style approach that prioritizes clarity over complexity.Show notes:(0:00) Intro(0:23) Why pilots overpay for CPAs(1:25) Family-office thinking for W-2 earners(3:42) Gary’s path into tax planning(8:13) Missed tax moves for W-2 professionals(11:57) What a good CPA should do(16:28) Why education beats tax prep(24:34) Bracket strategy and timing income(28:50) Estimated taxes pilots overlook(34:18) Turning tax savings into investments(43:57) OutroConnect with Gary Heldt:Sign up directly on the site. Choose personal, business, or both newsletter options: https://www.sbadvisors.cc/ Gary's Podcast: https://www.sbadvisors.cc/resources/podcasts 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 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.
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    44 mins
  • #141 - How Pilots Can Use Business Structures to Reduce Taxes with Toby Mathis

    #141 - How Pilots Can Use Business Structures to Reduce Taxes with Toby Mathis
    Jan 6 2026
    Tait Duryea and Ryan Gibson sit down with Toby Mathis to unpack one of the most misunderstood topics for high-income pilots: business structure and taxes. They explain when to use sole proprietorships, LLCs, S-corps, and C-corps, how losses and profits flow to your personal return, and why entity choice impacts audit risk and mortgage eligibility. This episode is a practical roadmap for pilots starting side hustles who want to lower taxes, protect assets, and avoid costly mistakes.Toby Mathis is a nationally recognized tax attorney, investor, and educator, best known for simplifying complex tax and asset-protection strategies for entrepreneurs and high-income professionals. He is a founding partner of Anderson Advisors, where he helps clients legally reduce taxes, structure businesses, and protect wealth. In this episode, Toby breaks down entity structures, audit risk, and practical tax strategies pilots can apply when starting or scaling a business.Show notes:(0:00) Intro(0:11) Why entity structure matters(1:40) Side hustles and W-2 tax offsets(3:01) Starting a business vs real estate(6:42) Flow-through Vs. C-corp taxation(8:49) Mortgage qualification pitfalls(11:38) Legitimate expense strategies(15:00) Augusta rule and home office(21:48) Why sole proprietors get audited(28:25) Profit Vs. Loss by entity type(41:20) Schedule C Vs. Schedule E risk(56:14) OutroConnect with Toby Mathis:Website: https://tobymathis.com/ YouTube: https://www.youtube.com/channel/UCX5nh607M8hSBLiMB9MgbIQ Books: https://www.amazon.com/Tax-Wise-Business-Ownership-Toby-Mathis/dp/0979786002 Tax Tuesday: https://andersonadvisors.com/tax-tuesdays/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 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.
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    56 mins
  • #140 - From Goals to Execution: A Year-End Playbook

    #140 - From Goals to Execution: A Year-End Playbook
    Dec 30 2025

    Tait Duryea and Ryan Gibson close out 2025 by pulling back the curtain on how high performers actually plan, execute, and stay intentional across money, business, and family life. From Spartan’s acquisition pace and Turbine’s investor roadmap to family board meetings, goal frameworks, and habit formation, this episode offers a grounded look at what it takes to build momentum year after year.


    If you want clarity instead of drift and action instead of resolutions, this conversation sets the tone for a focused, intentional 2026. Do not just listen. Decide who you are becoming and move.


    Show notes:

    (0:00) Intro

    (2:27) Family board meetings explained

    (4:32) Objectives and key results framework

    (6:29) Spartan’s 2025 growth numbers

    (9:29) Turning big ideas into action

    (12:21) Why most people never get clear

    (15:49) Day one Vs. One day mindset

    (18:40) Stability, mentorship, and leadership

    (21:02) Why 2026 looks like opportunity

    (23:36) 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 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.
    Show More Show Less
    24 mins
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