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Reading: Why Your ‘Financial Advisor’ Ignores Real Estate w/ Henry Yoshida
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Stay Current on Political News—The US Future > Blog > Realtor > Why Your ‘Financial Advisor’ Ignores Real Estate w/ Henry Yoshida
Realtor

Why Your ‘Financial Advisor’ Ignores Real Estate w/ Henry Yoshida

Olivia Reynolds
Olivia Reynolds
Published March 19, 2026
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REtipster does not provide tax, investment or financial advice. Always seek the help of a licensed financial professional before taking action.

Most people think their retirement accounts can only invest in stocks, mutual funds, and index funds. But that’s not really true.

In this episode, I speak with Henry Yoshida, CEO of rocketdollaron how investors can use self-directed retirement accounts to invest in alternative assets such as real estate, land deals, startups, and private investments.

Henry spent a decade at Merrill Lynch, built a robo-advisor acquired by Goldman Sachs, and now helps investors unlock retirement money for deals most people assume they can’t access.

Special offer: Save $100 on your new RocketDollar account when you use code ‘REtipster’ at checkout!

Transcript of the episode

Editor’s Note: This transcript has been lightly edited for clarity.

Key takeaways

In this episode, you will be able to:

  • Find out how retirement accounts like IRAs and 401ks can legally be used to invest in real estate and other private businesses outside of the stock market.
  • Find out why traditional financial advisors rarely mention self-directed investing and what structural incentives keep this option hidden from most people.
  • Understand the key differences between Roth and traditional IRAs, including flexibility rules that most people never hear about.
  • Find out how checkbook control and direct escrow accounts work differently and which one suits specific types of real estate businesses.
  • Hear why a financial expert believes the 60-40 stocks and bonds portfolio is outdated and what he thinks should replace the bond allocation.

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About the author

Seth Williams

Seth Williams is the founder of REtipster.com, an online community offering real-world guidance for real estate investors.

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