AJ Osborne Podcast

43. Tom Wheelwright: How the Wealthy Avoid Taxes (While W-2 Workers Get Crushed)


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It’s no secret that the wealthy pay very little in taxes. But how do they get away with it? It’s not because they’re cheating the system or finding a clever workaround.

It’s by design.

The tax code was written in a way that incentivizes building businesses, creating jobs, and investing in real estate. If you’re a consumer—even a high-earning one—you’re heavily taxed. But if you’re producing, you’re rewarded.

In fact, there are seven investments the government will actually pay you to make. Tom Wheelwright, Rich Dad Advisor, CPA for Robert Kiyosaki, and founder of WealthAbility, breaks down some of these investments and the different ways to build wealth without sharing half of it with Uncle Sam.

With tax increases likely on the horizon, high earners face a critical decision: stay trapped in earned income or move into the asset economy. Whether you’re filing your 2025 return or tax planning for 2026, we cover strategies and approaches to building wealth that could save you thousands of dollars.

 

Insights from today’s episode: 

  • The seven investments the U.S. government will pay you to make
  • What most Americans don’t understand about the United States tax code
  • Why investments, not income, shelter more of your money from taxes
  • The short-term rental “loophole” and other real estate tax deductions explained
  • Questions your tax advisor should be asking you (not the other way around)
  • Sign Up for My Newsletter Here: https://ajosborne.com/newsletter 

    Tax-Free Wealth - https://www.amazon.com/Tax-Free-Wealth-Permanently-Lowering-Advisors/dp/1937832058 

    TFW Advisors - https://tfwadvisors.us/ 

     

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