$20 Trillion Opportunity: How to Invest in Real Estate and Private Deals Using Your IRA | Henry Yoshida
Millionaire Mindcast
Matt Aitchison
4.4 • 716 Ratings
🗓️ 4 August 2025
⏱️ 51 minutes
🧾️ Download transcript
Summary
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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Transcript
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| 0:00.0 | What's going on, guys? Welcome into today's episode. My guest is Henry Yoshida, founder and CEO of Rockad Dollar, which is a fintech platform that is revolutionizing how investors use retirement |
| 0:22.5 | funds, specifically IRA funds, to access private and alternative investments. |
| 0:28.4 | In today's episode, we break down the power of self-directed IRAs like you've never heard |
| 0:35.0 | before. I know I hadn't, And we dove into why 20 trillion dollars |
| 0:40.9 | in retirement accounts is sitting untapped for private deals and where the opportunity is at |
| 0:46.0 | there. What investors can actually buy through self-directed IRAs and what they legally can't buy |
| 0:52.9 | through self-directed IRAs. |
| 0:54.7 | We also talked about how Rocket Dollar makes it possible to invest in real estate, |
| 0:59.4 | crypto, private equity, even pickleball leagues. |
| 1:02.2 | You're going to love the case study on that one using tax advantage dollars through their platform. |
| 1:09.2 | Common mistakes that investors are making with their retirement accounts |
| 1:13.4 | and how you can avoid them. We also talked about how sponsors and fund managers can unlock |
| 1:18.4 | new capital by tapping into massive funding pools like this. So if you've ever thought, |
| 1:24.2 | hey, I'd invest in that deal. If only I had the cash and you knew that that cash |
| 1:29.0 | was sitting in a retirement account that you didn't think you could invest out of, this |
| 1:34.0 | episode will open your eyes to a whole new capital source, a whole new world of possibilities |
| 1:38.3 | hiding in plain sight. Get ready to rethink how you build and deploy your retirement wealth or help other investors do the |
| 1:45.9 | same. Let's dive into today's episode with Henry Ishida. Let's take a quick break in here from |
| 1:50.7 | today's show sponsor. I want to personally invite you to the very first wise investor mastermind. |
| 1:57.6 | And this is going to be held in none other than the wine and food mecca of the world, |
| 2:01.6 | Napa Valley, California. This is going to be an exclusive multi-day retreat that is going to be |
| 2:06.3 | a blend of learning and masterminding with bucket list adventures, amazing wine, and hospitality |
... |
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