Welcome to the Dwanderful Real Estate Podcast, hosted by Dwan Bent-Twyford. Now in Season 8, the show is approaching an exciting milestone, nearly two million downloads.

Dwan shares her passion for real estate education, investing strategies, and learning from industry experts. This episode features Henry Yoshida, a financial services entrepreneur specializing in tax-advantaged investing and self-directed IRAs.

The focus of this conversation is simple but powerful: how investors can use retirement accounts to invest in real estate and build long-term wealth.

Meet the Guest: Henry Yoshida

Henry Yoshida is the founder of Rocket Dollar, a platform that enables investors to use retirement accounts for alternative investments such as real estate, private equity, and crypto.

With over 25 years in financial services, Henry specializes in helping individuals access tax-advantaged retirement funds in more flexible ways.

Through Rocket Dollar, investors can:

• Open self-directed IRA accounts digitally
• Invest in real estate and private assets
• Maintain tax advantages of retirement accounts
• Diversify beyond traditional stocks and mutual funds

Rocket Dollar currently serves billions in assets, with a significant portion allocated to real estate investments.

What Is a Self-Directed IRA?

A self-directed IRA is a retirement account that allows investors to go beyond traditional stocks and bonds.

Instead of limiting investments to public markets, investors can use their IRA to invest in:

• Real estate properties
• Private equity deals
• Syndications and limited partnerships
• Hard money loans
• Cryptocurrency and digital assets

This structure maintains the same tax advantages as a traditional IRA while giving investors more control over how their money is deployed.

How Real Estate Investing Works Inside an IRA

Henry explains that real estate inside an IRA works differently from personal ownership.

Key Tax Advantages:

• Rental income inside the IRA is not taxed
• Capital gains from property sales remain tax-deferred or tax-free (Roth IRA)
• Taxes are only triggered when funds are withdrawn personally (depending on account type)

This allows wealth to compound inside the retirement account without annual tax drag.

Why Investors Use Self-Directed IRAs for Real Estate

Most Rocket Dollar customers are experienced investors who already own real estate outside of retirement accounts.

They typically use self-directed IRAs because:

• They have accumulated retirement savings in 401(k)s or IRAs
• They want to diversify beyond stocks and mutual funds
• They are seeking passive income opportunities
• They prefer tangible investments like real estate

Instead of keeping money in traditional funds, investors redirect capital into real estate opportunities they understand and trust.

Investment Options Inside a Self-Directed IRA

Henry highlights several alternative investment options available through Rocket Dollar:

1. Direct Real Estate

Investing directly in residential or commercial properties.

2. Real Estate Syndications

Becoming a limited partner in larger investment deals or funds.

3. Private Equity Investments

Investing in private companies or private funds.

4. Hard Money Lending

Issuing loans to real estate developers and earning interest.

5. Cryptocurrency

Investing in digital assets for long-term growth potential.

These options allow investors to diversify beyond traditional markets.

Example: Hard Money Lending Through an IRA

One of the most popular strategies discussed is hard money lending.

Here’s how it works:

• The investor identifies a borrower (often a developer)
• A loan agreement is structured (e.g., 13%–17% annual interest)
• Rocket Dollar facilitates the transaction from the IRA
• Interest and principal payments flow back into the IRA tax-advantaged

Because the investment stays inside the IRA, returns grow without immediate tax liability.

Who Should Use a Self-Directed IRA?

Self-directed IRAs are best suited for:

• Mid-career professionals with existing retirement savings
• Investors with at least $10,000–$500,000 in retirement accounts
• Individuals seeking diversification beyond stock markets
• Experienced real estate investors looking to scale capital

Henry emphasizes that this is not typically a starter account, it is designed for investors ready to diversify existing wealth.

The Importance of Control and Diversification

A key theme of the episode is control.

Many investors feel limited by traditional retirement accounts that only offer stocks and mutual funds. Self-directed IRAs give them:

• More investment freedom
• Direct access to private deals
• Greater diversification options
• Alignment with personal investing knowledge

Henry notes that large institutional investors already allocate significant portions of capital into private markets like real estate and private equity.

Risks and Responsibility

While the strategy offers strong upside, it also comes with responsibility.

Investors must:

• Conduct their own due diligence
• Understand deal structures
• Accept risk in private investments
• Avoid relying solely on traditional financial institutions

Control also means accountability.

How to Get Started with Rocket Dollar

Getting started is simple:

1. Identify a private investment opportunity (real estate, syndication, or lending)
2. Open a self-directed IRA account
3. Transfer existing IRA or 401(k) funds
4. Deploy capital into chosen investments
5. Earn returns inside a tax-advantaged structure

Accounts can be opened online in just a few minutes, and funding can be transferred from existing retirement accounts.

Closing Thoughts: Curiosity as an Investing Advantage

Henry ends the episode with a powerful word: curiosity.

His message encourages investors to:

• Ask deeper questions
• Explore beyond traditional investing options
• Understand how wealth systems actually work
• Stay open to new strategies

Curiosity, he explains, is what leads to better financial decisions and long-term wealth building.

Turning Retirement Capital Into Real Estate Opportunity

Self-directed IRAs are reshaping how investors think about retirement wealth. Instead of limiting funds to traditional stocks and mutual funds, investors now have the ability to direct their retirement capital into real estate, private lending, syndications, and other alternative assets, all while preserving important tax advantages.

As Henry Yoshida explained, the real opportunity is not just access to new investment types, but control. Investors can align their retirement accounts with what they already understand best, real estate, while building long-term, tax-advantaged wealth.

For those looking to go deeper into real estate investing, Dwanderful is a dedicated real estate investing platform and podcast hosted by Dwan Bent-Twyford. The platform is built to educate, inspire, and equip investors at every level.

Visitors can explore free and paid learning resources, including:

• A free downloadable book titled Real Estate Lingo, designed to help investors understand essential industry terminology
• A paid book titled Five Pillars of Real Estate Investing, which breaks down core strategies for building long-term real estate wealth
• A quick interactive quiz game that helps users discover how they could potentially generate six figures in the next six months, whether they are purchasing their first property or expanding their portfolio. The quiz takes less than a minute to complete and offers personalized insights based on your investing goals

From education to strategy to real-world investing insights, Dwanderful serves as a complete hub for aspiring and active real estate investors.

Now, with these strategies in mind, Dwan takes us back into the conversation to continue breaking down how investors can take action and start using self-directed IRAs to build real estate wealth today. Contact us now!