Passive Income Pilots

#76 - MOST POPULAR EPISODE: Reduce Taxes & Maximize Returns Using PROVEN Strategies with Toby Mathis


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In this episode of Passive Income Pilots, Tait Duryea takes you back to one of the most downloaded episodes in the show's history with Toby Mathis from Anderson Advisors. Discover how tax laws can work for you through real estate investments, cost segregation, and bonus depreciation strategies. Toby breaks down the game-changing legal strategies high-income earners can use to reduce their tax burden and maximize returns drastically. If you're a pilot frustrated with taxes or looking to level up your knowledge, this episode is packed with powerful insights.


Toby Mathis is a tax attorney, author, and principal at Anderson Advisors, where he has spent over 25 years advising investors and business owners on tax strategies.  He is also a member of the Forbes Real Estate and Finance Council. As both an experienced real estate investor and a legal expert, Toby brings practical, actionable insights to the show. He specializes in helping high-income earners legally reduce their tax burden through real estate, business structures, and creative legal strategies. Toby is also known for his popular bi-weekly webinar, Tax Tuesday, and his #1 bestselling book "Infinity Investing," published by Forbes Books.


Enjoy the show!


Show notes:

(0:00) Intro

(01:13) Economic update and job market trends from the Federal Reserve Beige Book

(05:03) Tax challenges for pilots and strategies to reduce taxable income

(08:49) Debunking myths about LLCs and creating tax-deductible losses

(12:57) Understanding income types: active, portfolio, and passive income

(17:10) Can passive losses offset W-2 income for pilots?

(19:30) Tax implications of owning a business versus owning real estate

(23:11) Bonus depreciation and maximizing tax benefits with real estate investments

(31:46) Real estate professional status: how pilots can qualify and benefit

(45:31) Combining Airbnb with long-term rentals for optimal tax strategies

(58:04) Cost segregation and accelerating depreciation for significant tax savings

(1:10:05) Outro


Connect with Toby:

Company Website: https://andersonadvisors.com/ 

Website: https://tobymathis.com/ 

Youtube:  https://www.youtube.com/@TobyMathis 

Free Tax Webinar: https://andersonadvisors.com/tax-tuesdays/ 


Toby takes a deep dive into taxes at Spartan Investment Group:

Tackling the Toughest Tax Questions of all Time!

https://www.youtube.com/watch?v=GX8rFZSGeVc 



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.


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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.

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Passive Income PilotsBy Tait Duryea and Ryan Gibson

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