“I’m Not Smart Enough to Create the Investments, But I Know Where the Money Is” — Henry Yoshida on Playing the Right Side of Money

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Cut The Tie Podcast with Henry Yoshida

Most executives spend decades earning, saving, and investing money without ever truly understanding where their capital sits or how much control they actually have over it.

In this episode of Cut The Tie, Thomas Helfrich sits down with Henry Yoshida, CEO and co-founder of Rocket Dollar, to unpack the mindset shift that separates passive investing from intentional ownership. Henry shares his journey from corporate finance at Merrill Lynch to building financial technology companies that help people unlock alternative investments inside retirement accounts.

This conversation explores why access often matters more than invention, how comfort can quietly limit opportunity, and why knowing where the money is can change how executives think about risk, freedom, and long-term success.

About Henry Yoshida

Henry Yoshida is the CEO and co-founder of Rocket Dollar, a financial technology company that enables individuals to invest retirement funds into private and alternative assets. With a career rooted in financial services and retirement planning, Henry has built multiple companies focused on giving people more control over capital they already own.

His work centers on access, education, and empowering individuals to make informed decisions outside traditional Wall Street structures.

In this episode, Thomas and Henry discuss:

• Henry’s transition from corporate finance to entrepreneurship
• Why understanding capital matters more than creating investments
• How retirement accounts quietly limit choice and control
• The role of discomfort in long-term success
• Alternative investments and personal knowledge as a risk filter
• Why diversification means more than stocks and bonds
• Cutting ties with institutional thinking around money
• Redefining success beyond titles, status, and safety

Key Takeaways

• Access beats invention
  You don’t need to create investments to benefit from opportunity.
• Capital already exists
  The question is who controls it and how it’s used.
• Comfort can limit growth
  Security often delays necessary change.
• Risk is contextual
  What feels risky to institutions may feel obvious to individuals.
• Ownership creates clarity
  Control over money leads to better decisions.

Connect with Henry Yoshida

🌐 Website: https://www.rocketdollar.com/
🏢 Parent Company: https://www.retired.com
💼 LinkedIn: https://www.linkedin.com/in/henryyoshida/

Connect with Thomas Helfrich

🌐 Website: https://www.cutthetie.com
💼 LinkedIn: https://www.linkedin.com/in/thomashelfrich
📧 Email: [e-mail]
🚀 Instantly Relevant: https://www.instantlyrelevant.com

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