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

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: [email protected]
• NBAA (National Business Aviation Association): https://nbaa.org
• AOPA (Aircraft Owners and Pilots Association): https://www.aopa.org

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*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.