Your Retirement, Your Rules: How Rocket Dollar Helps You Invest Beyond Wall Street with Henry Yoshida

If you have most of your savings trapped inside a 401k or IRA and you’ve wondered how to do more than buy another index fund, this episode opens the door. Henry Yoshida, CFP and co-founder and CEO of Rocket Dollar, explains how regular investors can legally use retirement accounts to access private and alternative investments. You will hear how a reluctant Merrill Lynch rookie became a three-time founder by solving a problem Wall Street ignored, why diversification now means more than stocks and bonds, and how to take a more proactive role in your financial life without becoming a market guru. This conversation is a practical roadmap to self-directed IRAs, private market access, and smarter retirement strategy for entrepreneurs and professionals who want more control.

What You’ll Learn in This Episode

From “Plan B” to Category Leader: How Henry stumbled into finance, survived the dot-com downturn, and built three successful companies by serving overlooked customers.

The 401k Pivot That Changed Everything: The scrappy play that landed 120 small-business 401k plans and sparked a career focused on retirement accounts and real-world outcomes.

Why Traditional Diversification Isn’t Enough: What Henry means by “it’s the S&P 7,” why stocks and bonds now move together, and how non-correlated assets can improve risk-adjusted returns.

Self-Directed IRA 101: How Rocket Dollar lets you use an IRA or 401k rollover to invest in private and alternative assets, from single family rentals to private equity and venture funds.

Is This Even Allowed: The ERISA backstory since 1974, why private investments were always permissible inside IRAs, and why big brokerages never made it easy.

A Practical Allocation Mindset: How some investors shift 10 to 30 percent of IRA assets into alternatives while keeping the rest in broad index funds for balance.

Creative Investing Without Being an Expert: Why your local knowledge can be an investing edge, and how to think in terms of zig and zag when the public markets swing together.

The New A or B Retirement Conversation: Why the future of retirement accounts looks like regular IRAs for public markets and companion IRAs for private markets, and how both can work together.

Passive Is Over: Why “set it and forget it” no longer fits the times and what a proactive, aware approach looks like for busy founders and professionals.

Episode Highlights

The origin story that began with saving for law school and turned into a decade at Merrill Lynch guiding everyday savers inside break rooms across Austin.

The “richest man in Babylon” principle for modern retirement: start early, contribute consistently, and let compounding do the heavy lifting.

How Rocket Dollar acts as the “picks and shovels” to unlock retirement capital for private opportunities, without telling you what to buy.

Realistic minimums and examples for private funds that are now accessible to more investors, plus how customers typically use a self-directed IRA alongside a regular brokerage IRA.

A candid look at incentives on Wall Street and why most institutions keep you in their own public products.

Henry’s closing challenge to listeners: stop being purely passive, get informed, and take an active role in your retirement strategy.

Visit Rocket Dollar and Invest in what you want with a self-directed IRA

This episode originally aired on iHeart Radio 710 WOR The Voice of New York