Tag Archives: Retirement


Latest Trends in Retirement Plan Distributions With Henry Yoshida (Ep. 27)

In traditional forms of IRAs (individual retirement accounts), investment options are often limited to stocks, bonds, and mutual funds. However, “self-directed IRAs” enable owners to invest their retirement savings into alternative asset classes.


In this episode, Kevin Kaylakie speaks with Henry Yoshida, CFP®, founder and CEO of Rocket Dollar, Inc. They provide a brief overview of how self-directed IRAs function, their benefits, and the key rules one must be aware of before investing in it. They also explain why there is a discrepancy in the amount invested in traditional vs. self-directed IRAs across the United States.


Kevin and Henry discuss:


  • ”03:43” How the retirement plan landscape has evolved over the years
  • ”09:11” The two main types of self-directed IRAs
  • ”13:26” Prohibited transactions within a self-directed IRA
  • ”17:47” How investors like Peter Thiel manage to get billions of dollars into Roth IRAs
  • ”21:44” Up-and-coming alternative asset classes
  • And more




Connect With Henry Yoshida:


Connect With SineCera Capital:


About Our Guest:


Henry Yoshida is CEO and Co-founder of Rocket Dollar, a web platform that lets people invest tax-advantaged retirement dollars into private alternative investments. He is a Certified Financial Planner™ professional, licensed Realtor®, and has 20 years of experience in finance. In the past, Henry was the founder of venture capital backed robo-advisor Honest Dollar [acquired by Goldman Sachs], was the founder of MY Group LLC [$2.6B AUM retirement plan advisory firm], and spent 10 years at Merrill Lynch. 


He graduated from The University of Texas at Austin, has an MBA from Cornell University, and lives in Austin with his wife and two daughters.