
Henry Yoshida
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- Full Name
- Henry Yoshida
- Title
- Co-founder & CEO
- Firm
- Rocket Dollar
- Firm Type
- Fintech platform for self-directed retirement accounts and alternative investments
- Target Company Profile
- Alternative-asset platforms and issuers compatible with self-directed IRAs and Solo 401(k)s, including startup investing, real estate, private equity/debt, crypto, farmland, precious metals, and securitized assets.
- Sector Focus
- Fintech, retirement savings, self-directed IRAs, alternative investments, real estate, early-stage investing, private equity/debt
- Geographic Focus
- United States
- Location
- Austin, Texas
Background
Henry Yoshida is the co-founder and CEO of Rocket Dollar, an Austin-based fintech company founded in 2018 to help people invest retirement funds beyond public stocks, bonds, and mutual funds. Rocket Dollar’s own team page lists him as “Co-founder & CEO” and frames the company’s mission as making it “safe, simple, and fast” for people to control retirement savings.
Before Rocket Dollar, Yoshida co-founded Honest Dollar, a retirement savings platform for small businesses, self-employed workers, and independent contractors. TechCrunch reported in March 2015 that Honest Dollar raised a $3 million seed round led by Expansive Ventures, with Formation 8, Core Innovation Capital, and Aaron Patzer participating. Goldman Sachs completed its acquisition of Honest Dollar on May 23, 2016.
Yoshida’s background is heavily retirement- and wealth-management oriented. Brand Builders Group’s interview profile says he has been a Certified Financial Planner professional since age 22, spent 10 years at Merrill Lynch, founded MY Group LLC, an RIA with $2.6 billion in AUM, and is a licensed Realtor. The same profile says he graduated from the University of Texas at Austin, earned an MBA from Cornell University, and lives in Austin with his wife and two daughters.
Investment Thesis & Focus
- Yoshida’s public investment focus is best documented through Rocket Dollar rather than a personal angel-investing thesis. Rocket Dollar enables retirement-account holders to invest in alternative assets including real estate, startups, crowdfunding, peer-to-peer loans, farmland, gold, cryptocurrency, private equity, and private debt.
- He has publicly emphasized the idea that self-directed IRAs let investors use retirement dollars for private and alternative investments while keeping IRA tax treatment. In a Brand Builders Group interview, he said: “Anything that the IRS allows, which is anything from real estate to digital currency to making private investments into a friend’s startup technology business,” can be held in a self-directed IRA through the right provider.
- Rocket Dollar’s partner directory includes “Early Stage Investing” as an asset class and lists platforms such as AngelList Ventures, UpMarket, EquityNet, and Title3Funds as compatible partner options.
- For founders, the clearest strategic fit is not a generic seed pitch but a company that expands access to private markets, retirement-account investing, alternative assets, or infrastructure around compliant self-directed IRA/Solo 401(k) investing.
- I could not verify the stub claim that Yoshida personally has seven angel investments or a stated personal seed-stage check size from public sources.
Notable Investments
- Honest Dollar — Retirement savings platform co-founded by Yoshida; raised a $3 million seed round in 2015 and was acquired by Goldman Sachs in 2016.
- Rocket Dollar — Retirement fintech co-founded by Yoshida; Business Insider describes the company as helping users invest IRA dollars into alternative assets and notes a pitch deck used to raise $8 million.
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