Henry Yoshida - CEO & Co-Founder of Rocket Dollar episode artwork

EPISODE · Oct 13, 2025 · 47 MIN

Henry Yoshida - CEO & Co-Founder of Rocket Dollar

from Business Leaders of America Podcast · host Dylan Bloyed

Check out LiveGood, where top-tier wellness products meet unbeatable prices: https://www.livegood.com/Podcast Welcome to another episode of the Business Leaders of America Podcast. In this episode, I sit down with Henry Yoshida, CEO and co-founder of Rocket Dollar, a platform that empowers people to invest their retirement savings in alternative assets like real estate, startups, and private equity, using tax-advantaged accounts. Henry has built and sold multiple companies, including Honest Dollar, acquired by Goldman Sachs, and MY Group, acquired by Captrust. He’s also a Certified Financial Planner with a deep passion for helping individuals take control of their financial futures. We talk about what first sparked Henry’s interest in the financial and retirement industry, how Rocket Dollar is changing the way people think about investing for retirement, and some of the most overlooked ways to use IRAs and Solo 401(k)s to minimize taxes and build long-term wealth. Henry also shares insights into his role as Senior VP at Retired.com and how its mission to help Americans achieve financial freedom complements the work he’s doing at Rocket Dollar. If you’ve ever wondered how to make your retirement money work harder or how technology is democratizing access to alternative investments, this is an episode you won’t want to miss. Notable Awards and Recognitions • CEO and Co-Founder of Rocket Dollar, a platform enabling investors to use tax-advantaged retirement accounts for alternative assets • Senior Vice President at Retired.com, helping Americans achieve financial freedom through innovative tools and strategies • Founder of Honest Dollar (acquired by Goldman Sachs) and MY Group LLC, an SEC-registered RIA with $2.5 billion AUM (acquired by Captrust) • Former Vice President at Merrill Lynch with 10 years of experience in financial services • White House Intern under President Clinton, contributing to policy and administrative experience How to connect with Henry Yoshida • https://www.linkedin.com/in/henryyoshida/ • https://www.instagram.com/fitfinancehenry/ • https://www.retired.com/ • https://www.rocketdollar.com/ • Rocket Dollar: (855) 762-5383 Show Notes [1:45] Henry shares what first sparked his interest in the financial and retirement investing industry and what motivated him to start building companies that simplify how people invest for their future. [8:17] What alternative investments are and why giving people access to them through Rocket Dollar can be a game-changer for building a stronger, more diversified retirement portfolio. [13:43] Some of the most overlooked strategies for using IRAs and Solo 401(k)s to minimize taxes and build long-term wealth more effectively. [22:00] The key differences between self-directed IRAs and traditional IRAs, explaining the advantages and flexibility each option offers to investors. [26:09] The simple process for getting started with Rocket Dollar and how investors can begin exploring alternative assets within their retirement accounts. [35:35] Insights on his role as Senior VP at Retired.com, explaining how its mission to help Americans achieve financial freedom complements Rocket Dollar’s focus on alternative investing, [41:41] How listeners can connect with him directly and find more information about Rocket Dollar and Retired.com [43:50] Henry offers valuable advice for entrepreneurs looking to enter the investment or retirement industry, sharing key insights on what they should understand before taking the leap. Learn more about your ad choices. Visit megaphone.fm/adchoices

Check out LiveGood, where top-tier wellness products meet unbeatable prices: https://www.livegood.com/Podcast Welcome to another episode of the Business Leaders of America Podcast. In this episode, I sit down with Henry Yoshida, CEO and co-founder of Rocket Dollar, a platform that empowers people to invest their retirement savings in alternative assets like real estate, startups, and private equity, using tax-advantaged accounts. Henry has built and sold multiple companies, including Honest Dollar, acquired by Goldman Sachs, and MY Group, acquired by Captrust. He’s also a Certified Financial Planner with a deep passion for helping individuals take control of their financial futures. We talk about what first sparked Henry’s interest in the financial and retirement industry, how Rocket Dollar is changing the way people think about investing for retirement, and some of the most overlooked ways to use IRAs and Solo 401(k)s to minimize taxes and build long-term wealth. Henry also shares insights into his role as Senior VP at Retired.com and how its mission to help Americans achieve financial freedom complements the work he’s doing at Rocket Dollar. If you’ve ever wondered how to make your retirement money work harder or how technology is democratizing access to alternative investments, this is an episode you won’t want to miss. Notable Awards and Recognitions • CEO and Co-Founder of Rocket Dollar, a platform enabling investors to use tax-advantaged retirement accounts for alternative assets • Senior Vice President at Retired.com, helping Americans achieve financial freedom through innovative tools and strategies • Founder of Honest Dollar (acquired by Goldman Sachs) and MY Group LLC, an SEC-registered RIA with $2.5 billion AUM (acquired by Captrust) • Former Vice President at Merrill Lynch with 10 years of experience in financial services • White House Intern under President Clinton, contributing to policy and administrative experience How to connect with Henry Yoshida • https://www.linkedin.com/in/henryyoshida/ • https://www.instagram.com/fitfinancehenry/ • https://www.retired.com/ • https://www.rocketdollar.com/ • Rocket Dollar: (855) 762-5383 Show Notes [1:45] Henry shares what first sparked his interest in the financial and retirement investing industry and what motivated him to start building companies that simplify how people invest for their future. [8:17] What alternative investments are and why giving people access to them through Rocket Dollar can be a game-changer for building a stronger, more diversified retirement portfolio. [13:43] Some of the most overlooked strategies for using IRAs and Solo 401(k)s to minimize taxes and build long-term wealth more effectively. [22:00] The key differences between self-directed IRAs and traditional IRAs, explaining the advantages and flexibility each option offers to investors. [26:09] The simple process for getting started with Rocket Dollar and how investors can begin exploring alternative assets within their retirement accounts. [35:35] Insights on his role as Senior VP at Retired.com, explaining how its mission to help Americans achieve financial freedom complements Rocket Dollar’s focus on alternative investing, [41:41] How listeners can connect with him directly and find more information about Rocket Dollar and Retired.com [43:50] Henry offers valuable advice for entrepreneurs looking to enter the investment or retirement industry, sharing key insights on what they should understand before taking the leap. Learn more about your ad choices. Visit megaphone.fm/adchoices

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Henry Yoshida - CEO & Co-Founder of Rocket Dollar

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This episode was published on October 13, 2025.

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Check out LiveGood, where top-tier wellness products meet unbeatable prices: https://www.livegood.com/Podcast Welcome to another episode of the Business Leaders of America Podcast. In this episode, I sit down with Henry Yoshida, CEO and co-founder...

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