$20 Trillion Opportunity: Invest in Real Estate & Private Deals Using Your IRA

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What if your biggest source of investment capital has been sitting under your nose all along—completely untouched?

It’s true. There’s over $20 trillion locked in retirement accounts, and less than 1% of that is being used for private deals, real estate, or alternatives. What if you could tap into that pool… tax-advantaged?

Matt Aitchison sat down with Henry Yoshida, founder of Rocket Dollar, a fintech platform revolutionizing the way we invest retirement funds. Henry breaks down how self-directed IRAs (SDIRAs) are giving everyday investors access to real estate, crypto, startups—even pickleball leagues—with the same tax advantages as traditional IRAs.

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What You'll Learn from This Game-Changing Episode

Forget everything you thought you knew about IRAs.
In this episode, Henry Yoshida shares how investors are unlocking massive gains—tax-advantaged—through self-directed IRAs. Here’s what you’ll learn:

• The $20 trillion opportunity most investors are missing.
• Top 4 alternative investments you can make with your retirement dollars.
• The real reason advisors don’t recommend this strategy.
• A case study on how one investor turned a Roth IRA into a pickleball empire.

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What’s a Self-Directed IRA—and Why Should You Care?

"IRAs were designed to give people tax-advantaged investment growth. But 99% of them are stuck in stocks and mutual funds. Why not real estate, private equity, or even a startup you believe in?" — Henry Yoshida

Self-directed IRAs (SDIRAs) follow the same tax rules as traditional IRAs—but unlock your ability to invest in non-traditional assets.

✅ What You Can Invest In:

• Real estate (single-family, syndications, commercial)
• Startups and private equity
• Crypto (via platforms like Bitcoin IRA)
• Private credit, gold, and even cattle or racehorses

🚫 What You Can’t Invest In:

• Collectibles (art, baseball cards, wine)
• Life insurance

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The Deal That Most Investors Overlook

Henry shared how traditional advisors often discourage alternative investments.

Why? It’s not about safety—it’s about fees.

“These advisors often earn a percentage of assets under management. So if you roll money out into a self-directed IRA, they lose income—even if it’s a smarter move for you.” — Henry Yoshida

Many investors have the capital—they just don’t realize it’s trapped in a retirement account. Self-directed IRAs give you control and unlock deals you’d otherwise miss.

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Your Self-Directed IRA Playbook

Beginners

🔹 Tip: Start with real estate syndications—low-touch, tangible, and familiar.
🔹 Why it works: You’re investing passively, but still benefit from high cash flow and property appreciation.

Intermediates

🔹 Tip: Look into private credit and venture funds.
🔹 How to apply: Partner with reputable groups and study deal memos closely before committing.

Advanced

🔹 Pro Strategy: Convert to a Roth SDIRA and use it for moonshots like crypto or early-stage equity.
🔹 Outcome: When that big win happens? Your gains are 100% tax-free.

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Real-Life Wins: Social Proof That It Works

Henry shared some real Rocket Dollar success stories that prove SDIRAs aren't theory—they’re working now:

• 🎾 Pickleball League Investment: One investor used a Roth SDIRA to invest early in a pro pickleball league. Massive ROI—zero taxes owed.
• 🪙 Crypto Hedge Fund: A fund that bought into Solana under $0.15. It hit $160+ per token. That’s retirement-changing.
• 🐴 Cattle & Racehorses: Yep, some investors have used their IRAs for livestock and racing assets—with real returns.

These aren’t just anecdotes—they're validation that smart, creative investors are already winning with this strategy.

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Why the Next Decade Belongs to SDIRA Investors

Wall Street is watching—and shifting.

“Blackstone has partnered with Vanguard. Other private equity giants are teaming up with big retail brokers. Why? Because the next $10 trillion in capital is coming from you—the retail investor.” — Henry Yoshida

Private investments are no longer just for institutions and family offices. Now, mass affluent investors can access once-exclusive opportunities—without needing insider connections.

Here’s why SDIRAs are poised to surge:

• 💼 Demographic shift: Millennials and Gen X are inheriting trillions—and they prefer alternatives.
• 📉 Public stock shrinkage: Fewer IPOs, more private unicorns staying off the market.
• 🧠 Knowledge democratization: Podcasts, masterminds, and platforms like Rocket Dollar have closed the information gap.

Translation: If you don’t start exploring SDIRA strategies now, you’ll be playing catch-up later.

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Conclusion: Take Back Control of Your Wealth

Too many investors are sitting on goldmines—without even knowing it.

From real estate to crypto, startups to syndicated deals, your retirement capital could be working harder if you used a self-directed IRA. The opportunity is massive. The process is legal. And platforms like Rocket Dollar make it easier than ever.

“From missing out to massive upside—that’s what can happen when you redirect just a portion of your IRA into smart, alternative investments.” — Matt Aitchison

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Stay Connected & Learn More

🎧 Listen to the full podcast episode here: LINK

👁️ Watch the full episode here: LINK

📩 Be part of the discussion! Join our Facebook group: LINK

📅 Book a coaching call w/ Matt Aitchison: LINK

🚀 Enroll in our EXPERT-led courses: LINK

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