The Future of Retirement: Henry Yoshida on IRAs, Solo 401(k)s, and Real Asset Investing

Overview In this episode of the Breakfast Leadership Show, Michael Levitt welcomes Henry Yoshida, founder and CEO of Rocket Dollar, for a deep dive into how technology is reshaping investment accessibility. Together, they explore how average Americans can take control of their financial futures through self-directed IRAs and alternative asset investing. Empowering Diversified Investment Access Henry Yoshida opened the conversation by outlining the sharp decline in publicly traded companies—from roughly 16,000 to around 4,000 over the last century. He explained that a small group of leading firms in the S&P 500 now drive the majority of market returns. This imbalance inspired him to create Rocket Dollar, a platform designed to help investors diversify into non-correlated assets such as real estate. Interestingly, the company’s name came from his six-year-old daughter, representing the idea that investors can “go further” with their money. Enhancing Investment Accessibility Through Technology Michael and Henry discussed the evolution of financial markets and the crucial role technology plays in improving access to alternative investments. While the stock market has historically trended upward, Henry emphasized that returns depend heavily on timing. He shared how Rocket Dollar uses technology to simplify complex investment processes, giving everyday investors access to opportunities once reserved for institutions. Real Estate Investment Opportunities Michael turned the discussion toward real estate, describing it as one of the most tangible and stable investment opportunities. He noted how modern platforms like Rocket Dollar make it easier to participate without the traditional headaches of property management. Henry agreed, highlighting that real estate investing can provide not only financial returns but also personal satisfaction and control. Self-Directed IRA Real Estate Investing Henry explained the advantages of self-directed IRAs in allowing investors to use retirement funds for local real estate ventures. Unlike the abstract nature of public markets, this approach connects investors directly with their communities and properties. He pointed out that the ability to personally inspect and enhance properties provides a deeper level of engagement and understanding. Investments and Community Belonging Michael and Henry explored how investments can build stronger local economies. They discussed Austin’s growth as an example of how local investments can benefit both residents and investors. Michael emphasized that meaningful investments don’t just generate profit—they foster a sense of belonging and collective progress. Local Investment Strategies for Retirement Henry described Rocket Dollar as a bridge between traditional retirement savings and local investment opportunities. By investing in local startups or real estate, individuals can strengthen their communities while diversifying their portfolios. Michael underscored the mutual benefit of this model, which supports small businesses and generates sustainable growth within neighborhoods. Private Investment Opportunities and Trends Wrapping up the conversation, Henry and Michael discussed the growing shift from public to private investments. Henry highlighted the potential for investors to tap into emerging opportunities in private companies such as OpenAI and SpaceX, leveraging their existing retirement funds through Rocket Dollar’s platform. Michael encouraged listeners to explore diversification, think locally, and take advantage of new investment pathways that align personal wealth-building with community impact. Connect with Henry Yoshida: Visit RocketDollar.com to learn more about self-directed IRAs and alternative investments. Listen to more episodes and insights at: BreakfastLeadership.com/blog Henry Yoshida, CFP® CEO & Co-Founder, Rocket Dollar | SVP, Retired.com Henry Yoshida is a financial innovator who’s reshaping how Americans invest for their future. As the CEO and Co-Founder of Rocket Dollar, Henry empowers everyday investors to take control of their retirement savings through self-directed IRAs and Solo 401(k)s that unlock access to real estate, startups, and alternative assets traditionally reserved for the wealthy. Before launching Rocket Dollar, Henry founded Honest Dollar, a robo-advisor retirement platform backed by venture capital and later acquired by Goldman Sachs, and MY Group LLC, which was acquired by Captrust. His decade at Merrill Lynch built the foundation for his mission to democratize wealth-building through smarter, tax-advantaged investing. A Certified Financial Planner with an MBA from Cornell University and a degree from The University of Texas at Austin, Henry blends Wall Street expertise with a visionary approach to fintech innovation. His work has been featured across leading media platforms for its impact on the future of retirement investing. When he’s not helping investors rethink what...