What does it take to turn setbacks into rocket fuel?

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.

But Henry’s story isn’t just about business. During the pandemic, his young daughter was diagnosed with leukemia. Balancing the weight of a startup, family struggles, and personal challenges forced him to redefine what balance really means.

This raw and inspiring conversation dives deep into sales, resilience, entrepreneurship, and finding clarity in the midst of chaos. Whether you’re an aspiring entrepreneur, a seasoned business owner, or simply seeking perspective on life’s challenges, this episode delivers powerful lessons on grit, growth, and gratitude.

0:00 Intro

0:49 Family roots and early lessons

4:36 Why Henry chose finance over law

8:26 White House internship and new direction

14:40 Breaking into Merrill Lynch

19:03 Sales lessons and the 401k breakthrough

25:42 Leaving Wall Street and going independent

28:58 From consultant to entrepreneur

33:18 Launching startups and bold risks

35:45 Founding Rocket Dollar

43:26 COVID, family crisis, and resilience

47:43 Redefining balance in life and work

49:10 Rocket Dollar’s growth and impact

50:08 Daughter’s recovery and life today

52:17 Countdown to Impact

57:25 Closing and where to find Henry

Resources Mentioned:

📚 Greenlights by Matthew McConaughey

📚 Let Them by Mel Robbins

📚 Atomic Habits by James Clear

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