In this episode, Ryan and Tait from the Passive Income Pilots Podcast share real-world strategies tailored to pilots with high income and unconventional schedules.
Join Toby Mathis as he dives into pilot investing and reveals how two commercial airline pilots are building tax-free passive income while traveling the world.
Learn how real estate investing, syndications, and smart tax planning can help pilots maximize cash flow without sacrificing lifestyle.
Discover the truth about passive income, what actually works, and how to avoid common mistakes new investors make.
If you’re a pilot or high-income professional looking to build long-term wealth, this conversation breaks down practical, pilot-friendly investment models that deliver real results.
Show Notes: 0:00 Intro 0:53 Best pilot-friendly passive income models (real estate, syndications, debt) 2:43 “Passive income isn’t passive” + why education comes first 3:58 5 wealth moves pilots overlook (401k/SDIRA, diversification, private lending) 7:08 Building multiple income streams + the “buy cash flow vs buy toys” mindset 9:23 Why high earners avoid investing (tax drag) + how to think after-tax 9:59 Tax-advantaged real estate: depreciation, cost seg, and bonus depreciation 14:48 Biggest mistakes new pilots make (401k rollover + early planning) 17:18 Probationary year strategy: Roth conversions + layering strategies 20:01 Whole life / “infinite banking” as a liquidity tool for investing 30:14 What separates financially free pilots --------------------------------------------------------------------------------------------------------- Would you like to learn more about protecting your assets and minimizing taxes? Schedule a free consultation here: https://aba.link/868c32
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ABOUT TOBY MATHIS Toby Mathis, Esq. is the best-selling author of Infinity Investing: How the Rich Get Richer And How You Can Do The Same. Toby is a tax attorney and founded Anderson Business Advisors, one of the most successful law, tax, and estate planning companies in the United States. Learn more at https://aba.link/tobyaba --------------------------------------------------------------------------------------------------------- WARNING: I will NEVER ask you to contact me through YouTube comments, telegram, or WhatsApp. I have a checkmark next to my name, and my comment will be highlighted. Fake accounts do not have that. Please be aware of fake accounts trying to scam you using my name and picture.
The information provided in this video should not be construed or relied on as financial, investment, or legal advice for any specific fact or circumstance. Its content was prepared by Anderson Business Advisors with its main office at 3225 McLeod Drive Suite 100 Las Vegas, Nevada 89121. This video is designed for entertainment and information purposes only. Viewing this video does not create an attorney-client relationship with Anderson Business Advisors or any of its lawyers. You should not act or rely on any of the information contained herein without seeking professional legal advice.
