Rocket Your Dollar Self-Directed Investing Podcast

Surviving Setbacks: Sales, Startups, and Seizing Opportunity in Crisis

Written by The Rocket Your Dollar Podcast | September 19, 2025


In this episode of Point of Impact, Aaron Hale sits down with Henry Yoshida, co-founder and CEO of Rocket Dollar, to explore his remarkable journey from Merrill Lynch to launching one of the leading platforms for self-directed IRAs.

Henry opens up about the lessons he learned from immigrant parents who worked in the restaurant industry, his eye-opening time interning at the White House, and how he turned early struggles in finance into an innovative career path. He shares the pivotal moments of building companies, selling them, and starting again—this time from scratch.