$20 Trillion Opportunity: How to Invest in Real Estate and Private Deals Using Your IRA | Henry Yoshida

In this episode of Money Moves, Matty A. dives deep into the world of Self-Directed IRAs with Henry Yoshida, co-founder and CEO of Rocket Dollar. Henry breaks down how investors can take control of their retirement accounts and use them to invest in real estate, startups, private equity, crypto, and other alternative assets.

You’ll learn how the $20+ trillion retirement account market is shifting, what structures you need to know (Self-Directed vs. Checkbook IRA), and how to avoid the common legal pitfalls that derail investors. Henry also shares how Rocket Dollar is democratizing access to private deals through fast onboarding, tech-driven compliance, and investor education.

What You’ll Learn:

• How to unlock your retirement funds to invest beyond Wall Street
• The difference between traditional, SDIRA, and Checkbook IRA models
• What assets are allowed—and what transactions are prohibited
• Tax benefits of using retirement capital for real estate & private equity
• How real estate operators can accept SDIRA capital
• Why Millennials and Gen Z are seeking more control
• Mistakes to avoid when using your IRA for alternatives
• Why UBIT matters—and how to manage it
• How Rocket Dollar makes it easier to invest in what you believe in

Timestamps:

00:00 – Henry’s background & Rocket Dollar’s mission

03:00 – Retirement capital: A $20 trillion opportunity

06:30 – Comparing IRA types and structures

10:00 – IRS rules: what’s allowed and what’s not

15:00 – Tax deferral benefits for long-term wealth

20:00 – Platform, fees & investor experience at Rocket Dollar

25:00 – Accepting SDIRA capital as a fund manager

30:00 – Generational shifts in retirement investing

35:00 – Common SDIRA mistakes & how to avoid them

39:00 – Henry’s closing advice to investors and operators

Connect with Henry Yoshida & Rocket Dollar

Website: https://www.rocketdollar.com

LinkedIn: https://www.linkedin.com/in/henryyoshida/

Instagram: http://instagram.com/fitfinancehenry

Facebook: http://facebook.com/henrythecfp

YouTube: https://www.youtube.com/c/RocketDollar

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