Henry Yoshida is the co-founder and CEO of Rocket Dollar, a fintech platform that enables individuals to invest their retirement savings in alternative assets like real estate, startups, and cryptocurrencies through self-directed IRAs and Solo 401(k)s. Prior to Rocket Dollar, he founded Honest Dollar, a retirement-focused robo-advisor acquired by Goldman Sachs in 2016. He also founded MY Group LLC, a registered investment advisory firm with $2.6 billion in assets under management, which was later acquired by Captrust. Earlier in his career, Henry spent a decade at Merrill Lynch. He holds a B.A. from the University of Texas at Austin and dual MBAs from Cornell University and Queen’s University in Canada. Henry is based in Austin, Texas, where he lives with his wife and two daughters, and remains passionate about expanding access to smart, flexible retirement investing. In this conversation, Henry and Tarek share personal reflections on growing up as children of immigrants - and how those early experiences shaped their paths toward entrepreneurship.