In this episode of Distressed to Success, Brian speaks with Henry Yoshida, CEO and co-founder of Rocket Dollar and Digital Trust. They kick off by breaking down how self-directed IRAs work, rolling over old 401(k) or IRA funds to unlock private and alternative investments like real estate, small businesses or opportunity-zone projects and why the standard retirement custodians don’t offer that flexibility.
Henry explains the nuts and bolts of Rocket Dollar’s platform paired with Digital Trust’s custody services, and how this combo lets everyday investors deploy capital into communities they care about while preserving their tax benefits.
Brian and Henry then trace his journey from a decade at Merrill Lynch, through launching a mid-market 401(k) consulting practice, founding Honest Dollar (later sold to Goldman Sachs), to the 2018 birth of Rocket Dollar and its eventual merger with Digital Trust. Along the way they share inspiring stories, such as a Harvard Business School alum who funded rental housing back in her hometown of San Antonio, and a circle of friends who saved their favorite college bar from closure, all by redirecting their retirement savings.
These real-world examples underscore how tapping just a fraction of the $46 trillion in U.S. retirement assets can fuel local revitalization. Wrapping up, Henry offers a few nuggets of wisdom, “you succeed by your systems, not by lofty expectations,” and even reveals his favorite kitchen gadget, the Ninja Creami, for guilt-free protein “ice cream.”
If you’re curious how a self-directed IRA could power your next community investment, visit rocketdollar.com for a no-pressure chat with their U.S.-based team.
Timestamps
1. Overview of Rocket Dollar & Digital Trust platform – 01:20
2. How to roll over old 401(k)s into a self-directed IRA (and find forgotten plans) – 02:48
3. Henry’s entrepreneurial journey: Merrill Lynch → consulting shop → Honest Dollar → Rocket Dollar – 04:39
4. Real-world examples of using self-directed IRAs for community real estate & small businesses – 11:18
5. Key success insight: “You fail to the level of your systems” + life-balance advice – 21:57
Get in touch with Henry
Website: https://bit.ly/4atczNJ
LinkedIn: https://www.linkedin.com/in/ppoteet/
Instagram: https://www.instagram.com/fitfinancehenry/
Phone Number: 1-855-ROCKET-D or 1-855-762-5383
Get in touch with Brian
Last Best Partners' Website: https://www.lastbestpartners.com/
Brian's LinkedIn: https://www.linkedin.com/in/brian-seidensticker-90117021
Podcast LinkedIn Page: https://www.linkedin.com/company/distressed-to-success-podcast
Book Crucial Conversations: https://www.amazon.com/Crucial-Conversations-Talking-Stakes-Second/dp/0071771328
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