The Scott Show

Author: Scott Kitun

A podcast about tech, media and money. Hosted by Scott Kitun, featuring a rotating cast of internet personalities, founders, investors and media friends.
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Language: en

Genres: Business, Entrepreneurship, Investing

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Robinhood Drops a Nuke, Republic Reinvents The Forward Contract, and Rocket Dollar Founder Henry Yoshida On Self-Directed Private Investing
Episode 441
Wednesday, 2 July, 2025

In this episode of The Scott Show, Scott sits down with Henry Yoshida, founder of Rocket Dollar and now head of Retired.com, to talk about the massive wave of innovation coming to the $18 trillion retirement market. From launching Rocket Dollar to help everyday investors use their IRAs to invest in real estate, startups, and crypto — to now running Retired.com with a vision for a fully self-directed retirement future — Henry breaks down how we’re on the verge of a generational unlock in private market access. Scott and Henry dive deep into the rise of private equity for retail investors, the shrinking public markets, and why the 401(k)-only model is bleeding out. Bonus: Scott unpacks the implications of Robinhood’s tokenized stock announcement and Republic’s tokenized forward contract product “Mirrors”, and debate whether tokenization is a feature or the product. What You’ll Learn: - Why your IRA is the smartest way to invest in alternatives - How Rocket Dollar lets you deploy dormant dollars into private equity, real estate, and crypto - What Robinhood’s tokenized stock move really means - Why Republic’s “Mirror” might be the most innovative product in fintech right now - The real future of tokenization: stablecoin rails, 24/7 trading, and AI-powered portfolios. Support the show by creating a free account at Kingscrowd.com Follow Henry at Retired.com Follow Scott on IG/Twitter @Kitun