Episode 740
How to Use Your IRA to Invest in Real Estate & Alternatives | Henry Yoshida
Henry Yoshida of Rocket Dollar explains how to use IRAs for real estate, crypto, and private deals—unlocking $18T in retirement funds for alternatives.
In this episode of RealDealChat, Jack sits down with Henry Yoshida, co-founder & CEO of Rocket Dollar (a subsidiary of Retired.com), to explore how investors can unlock the power of retirement accounts for real estate, crypto, and private investments.
Henry shares his journey from financial advisor to wealth-tech entrepreneur, building platforms that custody over $12B in assets. He explains why traditional advisors rarely mention self-directed IRAs, how Rocket Dollar makes alternative investing as simple as wiring money, and what rules you must follow to stay compliant.
Here’s what you’ll learn in this conversation:
- Why 98% of IRA money is still stuck in public stocks & bonds
- The truth about “self-directed IRAs” and how they actually work
- The only two things you cannot invest in with IRA dollars
- How to buy real estate (single family, syndications, funds) inside an IRA
- Rules around prohibited transactions & why sweat equity is risky
- How Rocket Dollar integrates bank accounts with IRAs for easy investing
- Crypto, private equity, and unusual investments allowed in IRAs
- Market trends: why investors are seeking alternatives beyond the S&P 500
- The $35 trillion opportunity in retirement funds waiting to be unlocked
- Key tax advantages of using retirement dollars for real estate
📌 Learn more at RocketDollar.com — use code REI25 for $100 off setup.
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Timestamps
00:00 – Surprise: Crypto & real estate are allowed in IRAs
01:00 – Henry Yoshida’s background in wealth-tech & financial services
03:00 – Why advisors don’t talk about self-directed IRAs
05:00 – Retired.com, Rocket Dollar & $12B in custody assets
07:00 – What you can and can’t invest in (life insurance & collectibles only)
09:00 – Why investors are moving beyond public markets
11:00 – How Rocket Dollar accounts are structured & funded
13:00 – Benefits of unlocking retirement dollars for alternatives
15:00 – Step-by-step: setting up & funding your Rocket Dollar account
18:00 – Making investments: ACH, wires & account titling
19:00 – Performance examples: real estate in 2020, private credit funds
21:00 – Rules: prohibited transactions, Airbnb, sweat equity limits
23:00 – Property management & compliance tips
25:00 – Market trends & incumbents moving into alternatives
27:00 – Advice for younger investors: start small, be consistent
30:00 – Book picks & personal tools Henry uses
33:00 – Rapid fire: lies, advice, quotes & time savers
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