Taxes become more exciting, especially when it’s with Toby Mathis. Tait Duryea and Ryan Gibson welcome back tax strategist and investor Toby Mathis for another powerhouse session on how to keep more of your money before year-end. From bonus depreciation and the short-term rental loophole to smarter charitable giving and donor-advised funds, Toby reveals how high-income earners can legally slash their tax bills. Whether you’re a pilot, business owner, or passive investor, you’ll walk away knowing which moves to make before December 31, and how to turn your taxes into one of your biggest wealth-building tools. Toby Mathis is a tax attorney, investor, and co-founder of Anderson Advisors. With decades of experience advising thousands of investors, Toby simplifies complex tax laws into real-world strategies for building wealth. Known for making tax planning engaging and actionable, Toby helps high-income professionals, especially pilots and real estate investors, protect their assets and minimize taxes through smarter planning. Recommended episodes: #10 - Reduce Your Taxes & Maximize Returns Using PROVEN Investment Strategies with Toby Mathis #14 - Depreciation Demystified: Cost Segregation and Tax Savings in Real Estate with Toby Mathis 🎟️ Free Ticket to the December 4–6 Tax & Asset Protection Live Event in Dallas, TX Email Ryan at
[email protected] for one of the first 15 free tickets. Show notes: (00:06) What's exciting about today's episode? (01:05) Smart moves to make before year-end (03:59) Who Toby is and his investing philosophy (06:46) Understanding high-income tax pain and incentives (08:15) How to use real estate losses strategically (13:22) The Orlando toll road analogy for tax planning (17:03) Turning passive losses into active tax savings (25:23) The Airbnb loophole you probably missed (28:22) Donating appreciated assets for major deductions (34:33) Donor-advised funds: the smart way to give (43:04) 2026 bonus depreciation clarity (45:03) Post-year strategies and cost segregation timing (49:40) Real estate resilience and inflation insights Connect with Toby Mathis: TobyMathis.com Youtube Tax Tuesday — 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
[email protected] 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.
