• #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 Min.
  • #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.

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    24 Min.
  • #139 - How to Run Single-Family Rentals Like a REIT with Matthew Whitaker
    Dec 24 2025

    What if managing rentals like an institution is the key to higher returns and less stress?


    Hosts Tait Duryea and Ryan Gibson talk with Matthew Whitaker, founder of Evernest, about scaling property management with systems, data, and AI. From HELOC-driven growth to managing 20,000 homes nationwide, this conversation breaks down why professional operations, fraud prevention, and institutional discipline can transform single-family and small multifamily investing for pilots.


    Matthew Whitaker is the founder of Evernest, a nationwide property management platform serving over 20,000 rental homes across 50 markets. A former single-family investor who scaled through multiple market cycles, Matthew now focuses on applying institutional systems, data, and AI to professionalize rental operations and reduce friction for real estate investors.


    Show notes:

    (0:00) Intro

    (0:19) Why property management changes everything

    (1:22) From 30 homes to 20,000 doors

    (5:03) Using HELOCs to scale real estate

    (10:32) Why paying off your house isn’t safer

    (16:23) Inside Evernest’s national platform

    (18:21) Tenant fraud and underwriting risks

    (22:12) Why in-house maintenance lowers costs

    (31:21) AI predicting repairs and NOI

    (34:10) Institutional systems for small rentals

    (46:07) How to work with Evernest

    (47:14) Outro


    Connect with Matthew Whitaker:

    • Website: https://www.evernest.co/



    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.

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    48 Min.
  • #138 - How to Vet Deals, Operators, and Advisors the Right Way with Mat Sorensen
    Dec 17 2025
    Tait Duryea and Ryan Gibson sit down with Mat Sorensen of Directed IRA to tackle one of the most common investor questions: Who do you actually trust when investing in alternative assets? The conversation breaks down how to vet operators, assess risk, understand leverage, and use self-directed retirement accounts responsibly. Mat shares real-world insight from seeing thousands of deals flow through his firm, explains why advisors often avoid alternatives, and outlines practical rules for due diligence, alignment, and saying no to bad opportunities.Mat Sorensen is a nationally recognized authority on self-directed retirement investing and the CEO of Directed IRA. A tax and business attorney with over 20 years of experience, Mat has helped thousands of investors use IRAs and 401(k)s to invest in alternative assets like real estate, private equity, and startups. He is the author of The Self-Directed IRA Handbook and co-hosts educational events and podcasts focused on empowering investors to take control of their retirement capital.Show notes:(0:00) Intro(0:29) Understanding investment risk(4:54) What custodians do and don’t do(6:01) Why advisors avoid alternatives(9:09) How wealthy investors allocate capital(13:55) What you pay a self-directed custodian for(18:16) The “bring your own deal” reality(25:05) Identifying an operator’s real edge(33:07) Debt as the biggest risk factor(48:28) Learning when to say no(51:57) OutroConnect with Mat Sorensen:Website: https://directedira.com/ YouTube: https://www.youtube.com/@MatSorensen/videos Learn more about: Alternative Asset Investor Summit - https://altassetsummit.com/ Episodes Mentioned:1. #124 - $44 Trillion and the Future of Retirement Investing with Mat Sorensen2. #110 - The IRA Club Advantage: The Self-Directed IRA Strategy for Pilots with Ramez Fakhoury 3. #36 - Decoding the Untapped Potential and Complex World of Self-Directed IRAs with Derreck Long 4. #9 - Demystifying IRAs: Transfers Vs. Rollovers with Carrie Cook —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 *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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    52 Min.
  • #137 - Revocable Vs. Irrevocable Trusts: What Pilots Must Know with Adam Kintigh
    Dec 9 2025
    Clarity and control for the wealth you’re building. Tait Duryea and Ryan Gibson sit down with asset protection expert Adam Kintigh for his third appearance to break down one of the most misunderstood pieces of a pilot’s financial plan: the revocable living trust. Discover how to structure your trust, avoid probate disasters, protect your heirs from creditors, ensure your wealth goes where you intend, and understand the real difference between revocable and irrevocable trusts. If you've ever wondered how to secure your legacy and prevent costly mistakes, this episode is essential listening for pilots building serious wealth. Adam Kintigh is an asset protection and estate planning expert at Nevada Corporate Headquarters. He builds trusts, LLC structures, and multigenerational plans for high-income earners, including many pilots, helping them safeguard their wealth and protect their families. In this episode, he breaks down revocable trusts, probate pitfalls, creditor risks, and practical estate planning strategies.Show notes:(0:00) Intro(0:34) Why pilots must understand trusts(1:00) Adam returns for his third episode(6:25) Will Vs. Trust explained(8:52) The true cost of probate(10:21) Spendthrift protections for children(13:32) When irrevocable trusts matter(17:41) How to design a wealth roadmap(25:48) Who actually comes after your estate(39:00) How to correctly fund your trust(51:07) Why trust naming protects privacy(55:50) OutroConnect with Adam Kintigh:Email Adam at: adam@nchinc.com and mention Passive Income Pilots to get started Website: https://nchinc.com Episodes Mentioned:1. #114 - Trusts, Taxes & Transfers: What Every Investor Should Know with Amanda Wynalda: https://passiveincomepilots.com/episode/114-trusts-taxes-transfers-what-every-investor-should-know-with-amanda-wynalda 2. #119 - LLCs, Trusts, and Bulletproof Asset Protection with Adam Kintigh: https://passiveincomepilots.com/episode/119-llcs-trusts-and-bulletproof-asset-protection-with-adam-kintigh 3. #127 - LLCs, Trusts, and K-1s: Smarter Asset Protection with Adam Kintigh: https://passiveincomepilots.com/episode/127-llcs-trusts-and-k-1s-smarter-asset-protection-with-adam-kintigh Learn more about: NCH Consultation for Passive Income Pilots Investors: https://calendly.com/nchconsultation/nch-consultation-for-pipp?month=2025-12 —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 *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 Min.
  • #136 - What HGTV Won’t Tell You About Flipping Houses with Leka Devatha
    Dec 2 2025
    Are you using the exit strategies that actually work in this market?Hosts Tait Duryea and Ryan Gibson talk with seasoned investor and author Leka Devatha to pull back the curtain on what’s real and what’s not in flipping, reality TV, and today’s housing market. Get ready to uncover the truth behind her Amazon Prime episode, learn the creative strategies inside her new book Return on Real Estate, and discover how investors can win even when the market slows. From mid-term rentals to ADUs, conservative underwriting, and Seattle’s shifting landscape, this episode gives pilots practical insights they can apply anywhere.Leka Devatha is a Seattle real estate investor, developer, luxury broker, and author with over $100M in completed projects. She’s known for her Amazon Prime flipping episode, her high-growth investor meetup, and her BiggerPockets book Return on Real Estate. Leka specializes in creative, practical strategies that help investors build equity, cash flow, and resilience in shifting markets.Show notes:(0:00) Intro(3:38) What’s real and fake about TV house flips(5:01) Leka’s $100M real estate journey(7:05) Lessons hidden inside the “fake flip”(8:38) How her book Return on Real Estate is structured(11:43) How she underwrites deals in today’s market(13:54) Why buyers are picky and inventory patterns(21:09) Seattle trends, taxes, tech workers, and investor behavior(27:21) Leka’s favorite “adventure” strategy(36:13) What mid-term rentals really are and who rents them(41:20) OutroConnect with Leka Devatha:LinkedIn: https://www.linkedin.com/in/leka-devatha-5616bb185/ IG: https://www.instagram.com/leka_devatha/?hl=en Return on Real Estate by Leka Devatha: https://www.amazon.com/Return-Real-Estate-Agility-Maximize/dp/1960178792 Leka’s flipping episode: “Million Dollar Zombie Flip” on Amazon Prime (search Amazon Prime for the show title)Join Leka’s investor community: Real Estate at Work (Seattle meetup) - https://www.meetup.com/realestateatwork/?utm= —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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    42 Min.
  • #135 - The Truth About Oil and Gas Investing with Tim Pawul
    Nov 26 2025
    Are you unknowingly passing up five-figure tax savings available right now?Tait Duryea and Ryan Gibson sit down with oil and gas expert Tim Pawul to reveal why minerals, royalties, and non-operated working interests have become one of the most powerful tools for cash flow and tax strategy. Get ready to understand the real reason hydrocarbons aren’t going anywhere, how minerals function like “underground real estate,” and why non-op wells offer significant first-year tax advantages for high-income earners. Discover how pilots can use this asset class to balance real estate, reduce taxable income, and access institutional-quality deals with transparency and scale.Tim Pawul is the President of Minerals and Royalties Authority, a leading connector, advisor, and investor in the oil and gas minerals space. With over a decade of experience mapping the institutional evolution of minerals, Tim has become one of the industry’s loudest, most trusted voices. He hosts The Minerals and Royalties Podcast, works with institutional and private investors, and brings unmatched insight into minerals, royalties, and non-operated working interests. His deep industry relationships make him a go-to resource for anyone serious about energy investing.Show notes:(0:00) Intro(1:04) Fossil fuel dependence today(2:07) Introducing guest expert Tim Pawul(4:06) How Tim entered the minerals industry(7:02) Why shale changed everything(11:12) How minerals became institutional(19:11) What mineral rights actually are(32:39) How non-op working interests work(44:54) Red flags and due diligence tips(51:32) OutroConnect with Tim Pawul:LinkedIn: https://www.linkedin.com/in/tim-pawul-54aa9526/The Minerals and Royalties Podcast:Apple Podcasts: https://podcasts.apple.com/us/podcast/the-minerals-and-royalties-podcast/id1502759760 Spotify: https://open.spotify.com/show/2uiMdKFVMq7hWv1EBCDLsI Learn more about: Turbine Capital Iron Horse Energy Fund providing 80-85% tax deduction for 2025:https://turbinecap.investnext.com/portal/offerings/8798/Turbine Capital Oil & Gas Tax Benefits eBook: https://drive.google.com/file/d/17jUYSuoJGCU2ea4SN6MLgazmp-3LE2Lt/view Terms not explained during the episode: ESG = Environmental, Social Governance. ESG stands for Environmental, Social, and Governance, a set of standards used to evaluate a company's sustainable and ethical practices.AFE = Authorization For Expenditure. A formal document used in the oil and gas industry to outline the detailed cost estimate and approval for a specific project, such as drilling, completion, or reworking a well. It serves as a budget and a project proposal, requiring partner approval before capital is committed and tracking expenditures against the budgeted amount. G&A = General and AdministrativeNAPE Expo: https://registration.expologic.com/registration/types/668F3878-BC35-4659-A750-6491C592938D/3591 NAPE Registration Discount Code: MRA26 to get $75 off—Do you have questions or want to discuss this episode? Contact us at ask@passiveincomepilots.com *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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    53 Min.
  • #134 - Fatigue, Flight Deck Safety, and the Science of Sleep with Dr. Adam Shapiro
    Nov 18 2025

    Sleep becomes exciting, especially when it’s with Dr. Adam Shapiro. Tait Duryea and Ryan Gibson sit down with this board-certified sleep specialist and ATP pilot to uncover what every aviator needs to know to protect their health and their medical. Get ready for practical guidance on staying sharp, staying healthy, and staying in the cockpit longer.


    Dr. Adam Shapiro is a board-certified sleep medicine specialist, ENT surgeon, senior FAA Aviation Medical Examiner, and ATP-rated pilot. With more than three decades in clinical practice and a deep background in human factors, circadian rhythm, and sleep disorders, he helps pilots identify and resolve sleep issues before they become medical problems. Through Aero Medical Sleep Consultants, he works with individual aviators and aviation organizations to improve sleep quality, mitigate fatigue risks, and protect FAA medical certifications.


    Show notes:

    (0:00) Intro

    (01:07) Protecting your medical like a check ride

    (07:00) How Dr. Shapiro helps pilots

    (09:49) Real-world sleep hygiene basics

    (12:12) What sleep actually does for the body

    (14:01) Managing shifting time zones

    (17:54) Best practices for red-eye preparation

    (20:06) The most common sleep disorders

    (39:26) The science and risks of cockpit naps

    (49:34) Outro


    Connect with Dr. Adam Shapiro:

    • Website: https://www.aeromedsleep.com/
    • LinkedIn: https://www.linkedin.com/in/adam-shapiro-62823441/


    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.

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    50 Min.