Henry Yoshida
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Jun 24, 2026
Democratizing Alternative Investments: The Future of Tax-Advantaged Retirement with Rocket Dollar's Henry Yoshida
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13:02John Lee DumasHOST
I mean, what does it take to build and to scale an innovative f- uh, an innovative fintech platform in the retirement space today? And I think that's the key word, in the retirement space today.

Henry YoshidaGUEST
So I think that sometimes people think that all entrepreneurs, you know, they, they go into an industry because they have completely fresh eyes and no preconceived notions.

Henry YoshidaGUEST
But I think when you're dealing in a regulatory environment overlaid with the very personal part of, of handling people's money, it actually helps to have a good contextual understanding of the existing incumbent systems and protocols, uh, and the way things have been done in the past in place, but then maybe look at it from a different angle.

Henry YoshidaGUEST
Like, you know, just position yourself a different side of the room and see if you see things differently.

Henry YoshidaGUEST
I mean, the reason I got into unlocking retirement funds to do private investments, I, I didn't know that these kinds of accounts were possible, but I had a lot of friends who were doing private investments, and the one thing they kept complaining about was that, "I have all these deals that I want to do potentially after I've done one private deal, but I'm running out of capital to go do that." So kind of made me start thinking through the lens of where is capital, where is capital held by average American people, and then m- basically linking that bridge back to people wanting to invest in private alternatives.
Bonus Episode: Invest In 9,000 Alternatives: Inside Your Rocket Dollar Self Directed IRA
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Henry YoshidaGUEST
that there's a lot of pent-up interest for alternative investments, but the limiting factor is that there's just so many of them.

Henry YoshidaGUEST
It's hard for people to understand what's good, what's bad, what's appropriate, what's not appropriate.

Henry YoshidaGUEST
I think the next nut to crack would be just like a general record-keeping system, so somewhat of like a QSIP system, but for private investments.

Henry YoshidaGUEST
Someone's going to create that indexing platform, and I think that's the next evolution, but You know, really, the biggest learning for me in the success of Rocket Dollar is that once people get to a certain investable asset size, then they really are interested in looking at opportunities that maybe go beyond the stock bond and mutual fund market, which has gotten even more concentrated in my entire career.

Henry YoshidaGUEST
And there's just not a lot of platforms that facilitate this true diversification into things that are non-correlated, non-registered and private and alternative investments.

Henry YoshidaGUEST
And, you know, that's been the biggest thing for me is that there's pent up demand.
5 MINS LATER
Q+A: What we can learn from America's $17 trillion retirement pool
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Sean AylmerHOST
In Australia, we've had our regulator here has done a very big report recently on private credit or on public and private markets more generally, including private credit, and whether they should be regulated or not, etc., Is it a tie that you just can't hold back private credit? I mean, where is private credit

Henry YoshidaGUEST
going? Well, I think before I answer that question, I do want to say that I think that all investments have some level of regulation.

Henry YoshidaGUEST
Now, just because something may not be regulated as your typical listed equities market, that means that doesn't by virtue just indicate that it's not regulated.

Henry YoshidaGUEST
It's just regulated in a different way or regulated to a lesser degree because the market itself just quite may not be that mature.

Henry YoshidaGUEST
But The second part, your actual question, is that I recently gave some comments that, no, I don't think it's going to go away.

Henry YoshidaGUEST
I think that it's going to continue to gain more market share in 2026, especially here in the United States.

Henry YoshidaGUEST
And the amount of market share that I expect private credit to gain in 2026 will actually be in excess of what they've gained in the last three to five years combined.
5 MINS LATER
Sean AylmerHOST
If I'm investing in 2026 in my DIY fund or an IRA in the US, um, Is it time to move more into alternatives away from the whole 60-40 kind of theme, which seems to have been held water for decades, really? But is it time to move on?