The Hidden Retirement Money Strategy Real Estate Investors Need to Know

Henry Yoshida, CFP (00:00)
So if this money gets redeployed, it will be removed from the public capital markets and redeployed into the private market. So if it goes into real estate, let’s just say it’s real estate and let’s say it’s a 20 % move. Well, that’s an $8 trillion move into real estate that’s not held by institutions that make like, you know, cutthroat decisions, $100 billion at a time. It’s going to be made by hundreds of thousands of investors buying one property at a time up to a fourplex.

Cody Crabb (01:57)
Welcome back to the Real Estate Pros podcast. I’m Cody Crabb with Investor Fuel. And today I’m joined by Henry Yoshida, CEO and co-founder of Rocket Dollar. He helps investors use things like IRAs and solo 401ks to invest in real estate and alternative assets. So we’re going to break down how investors can unlock this capital they already have access to and deploy it in a more effective way. And it’ll get them started in being able to invest the way they want to. So Henry, thanks so much for joining us.

Henry Yoshida, CFP (02:25)
Thanks a lot. Thanks Cody. Thanks for having me.

Cody Crabb (02:27)
So something we were chatting a little bit before the podcast, ⁓ and one of the things that you mentioned was that this is a concept that is not super well known, or maybe it is well known, but more people need to know about it. ⁓ So just as a kind of background a little bit, can you kind of give us the high level view, just for the people that are listening to this that are brand new to real estate, ⁓ can you give us like the quick overview of like the self-directed IRA

for using those for real estate, ⁓ just so people can understand. ⁓ I’m totally including myself in that group, because I’m a little unaware as well.

Henry Yoshida, CFP (03:04)
Understood.

And look, people shouldn’t feel bad. I’ve worked my entire career with retirement accounts. So tax advantage 401k IRAs since the year 2000 and it’s now 2026. And I only found out about these accounts actually in 2013 myself. So it was literally midway through my career in this particular part of the industry. But, you know, to answer your question, the it actually goes back to the origination of IRAs. So it was created with by law in 1974 called ERISA.

Cody Crabb (03:21)
Wow. Yeah.

Henry Yoshida, CFP (03:33)
and it stands for Employees Retirement Income Security Act. And that law in 1974 is what actually created IRAs and 401Ks as we know it even today in modern times. So I like to tell people that it just hit it’s, you it’s a little over 50 years old. So maybe not too different than some of the people in the audience just to give people a sense. But even then, the actual code law stated that IRAs were never disallowed from investing in things that aren’t stocks, bonds, and mutual

Cody Crabb (03:51)
Yeah.

Henry Yoshida, CFP (04:01)
So the biggest thing I hear all the time is that, wow, I thought that you were only allowed to do stocks, bonds, and mutual funds with your 401ks and your IRA money. But the reality was the law was never written that way. The raw…

law was just interpreted that way. And the companies that became big and started in this space were your Fidelities who sponsor 401k plans, but they are also a manufacturer in a large brokerage house. They are manufacture of mutual funds, which are a collection of stocks. So they basically set up the vehicles of the ones they provide to not be allowed to invest in anything outside. And since those are what are held by tens of millions of Americans today, it’s also assumed that you can’t own anything

other than stocks, bonds, mutual funds inside of these accounts, but the law was never stated that way in 1974. So that’s the awareness part, Cody, and I tell people that. And there are a small segment of the population of which I joined in 2013 who have actually known about this and they’ve used IRA monies to invest in things like real estate, know, germane to the community we’re speaking to today.

Cody Crabb (05:03)
Yeah, and I think it’s important for people to know what options they’ve got because I’ve heard a lot of people say stuff like, know, they’re gathering assets to be able to invest and things like that. some of these people have everything they need right there just waiting in an IRA. They just have to do a couple of little tweaks and then they’re ready to go. what is it that… So what kinds of advantages just as a, again, real quick primer for this.

What kind of advantages are there to doing this type of, I mean we’re talking to real estate investors so they know what kind of advantages real estate has. But just out of curiosity, what is it that this can get you that your typical ⁓ investment account with the stocks and bonds and what not can maybe not do?

Henry Yoshida, CFP (06:45)
Well…

Yeah, the main thing it’s about diversification, right? So, I mean, I do think that people, ⁓ people graduate for the types of investments they do. One of the things about real estate that makes it great. ⁓ It’s easy for people. Once you get into real estate, you get the benefits of it people say it’s a great investment. Whether you own that in a tax-deferred account, like an IRA, or whether you own it straight up and you’re taking advantage of depreciation and losses to be able to write off against the income, or you you may be operating as a short-term.

rental, which allows you to qualify and write off any losses in depreciation and bonus depreciation against your active W2 type income. Whatever the case may be, there’s an entry point to getting into real estate. you don’t just decide to do that tomorrow. You typically earn any 20, 30, 40, 50, $60,000 saved up. So how do you get that? Right. You graduate because maybe you put $10,000 and then an additional $2,500 per year for the next four years. So you had 20,000 in principal.

and that grew over six years to $50,000, at which point you liquidate and now you have a down.

payment for your first rental property and so forth. So it’s a graduation. So I tell people that that it’s maybe a level that you have. And if you are choosing to use a IRA money, there’s two things that maybe that allows you to jumpstart the ability to get into real estate as an asset class for your investment portfolio, which is that you probably already have that 50,000 accumulated there. Right. So if you’re mid career and you’ve worked at three or four different companies and you’ve contributed 401Ks, made contributions to IRAs over the years, you have money.

And now I just told you that you can access that money to then go into real estate. So that’s that’s that you may already be graduated at the level where you can enter real estate, right? But if you only have $5 to invest, you should probably start with a Robinhood account and just go, you know, invest in a broad market index fund because you could start that now with $1. You can’t start investing in real estate with $5.

Cody Crabb (08:42)
Right, yeah, that’s a good call out as well. And I think it’s cool that this is like an exciting way for someone that has kind of always wanted to do it. This might be a way to get into it way quicker than you thought you might be able to. ⁓ So.

Henry Yoshida, CFP (08:56)
Well, and you won’t have to

worry about all the tax losses and depreciation because I mean, you know, one thing, the one thing, and I’m a real estate investor too, it’s that, ⁓ you, make that decision to become a real estate investor. Then there’s a whole nother educational learning curve of how you manage that property and how you might account for that property with your tax advisor and so forth. So truth be told, if you use IRA dollars to do it, you could get into step one, which is getting into real estate. But since you own it inside of an IRA,

things like depreciation, things like, you know, balancing losses against like the rental income that you have.

None of that really is particular to owning it inside of an IRA. And the one thing I didn’t mention, Cody, I’ll just go back real quick, is that you mentioned that we help unlock people’s money in IRAs and 401Ks. And I said that there’s a certain level that you need to reach to invest in real estate. Well, that number as of the end of 2025 now in accumulated IRAs and retirement accounts in the U.S. is getting close to $46 trillion. So…

This is not a small amount of money that the average American investor slash saver slash employee has. ⁓

These are middle-class people who could be mid-career who might find that they actually have a couple of hundred thousand dollars to go into real estate investing, whether that’s buying a whole property or getting into a syndication, because they built those savings up by probably having a principal base of a hundred thousand, and then it’s grown and doubled to 200,000 at a time. And this is held by millions of Americans.

Whereas the number of Americans who just happen to have $50,000 in cash or $200,000 cash sitting in their bank account to go buy property is not in the millions.

Cody Crabb (10:26)
Yeah, wow.

Yeah, and it really makes it seem like a massive hurdle. So the idea that this could be something that could be done by a lot more people is pretty exciting. So let’s rewind a little bit. We didn’t really get into your history as much, and I’d like to do that now. So can you kind of give us a little bit of info on what led you into building Rocket Dollar?

Henry Yoshida, CFP (10:44)
Exactly.

I mentioned before that I had started ⁓ in the financial services industry in the year 2000. So I graduated college May of 2000 from the University of Texas here. You said you’re in Salt Lake City. So don’t know a lot of BYU fans there, you know, we play them ⁓ in the tournament. But so I accidentally got into the niche because when you join a big firm like that, they kind of decide what your specialty is going to be. And I ended up getting into this tax advantage retirement account space and grew with it.

Cody Crabb (11:09)
very much so, yeah.

Henry Yoshida, CFP (11:24)
And so I worked as a traditional consultant for 401ks and IRAs for individuals and small businesses. And I kept staying in that space. And after a couple of other businesses, I did management consulting after 10 years at Merrill Lynch in the retirement space. And then I built a FinTech company, which was a small starter IRA provider in a digital mobile app that was acquired by a Wall Street firm. And in 2018, I realized that back in 2013, I did learn that there was a very small part of the

population

that had known that they could unlock and tap into their retirement 401k savings to invest with massive tax advantages into private and alternative investments. Now, I didn’t tell you the story of how I found out in 2013, but I stumbled upon a Wall Street Journal article that had highlighted two very diametrically different individuals, but both doing the same strategies, which was investing in private companies using their 401k and IRA money. One was Mitt Romney, who had lost

in running for the presidential campaign, obviously well known in the state of Utah, but he ran against Barack Obama and lost. And the other one was Peter Thiel, the billionaire co-founder of PayPal, first investor in Facebook. And these two people are very, very different, right? But…

Cody Crabb (12:28)
very much so yeah

Henry Yoshida, CFP (13:14)
What they both did was they knew in the early 2000s and late 90s how to tap into 401k plans to invest in private companies and then get hundreds of millions in Mitt Romney’s case and billions in gains without having to pay taxes. In Peter Thiel’s case with his Facebook and PayPal investments ⁓ by tapping into these accounts. And that’s when I realized that regular people could benefit from being able to tap into accounts that they already have.

and feel like that they’re pretty limited to just investing in the S and P 500 stocks and a couple of mutual funds here and there to then go into private and alternative investments. And if they turn out to be home runs or in these guys cases, like massively successful grand slams, then they would be able to not have to pay taxes on any of those gains. And that’s what led me to thinking about how I can create a platform that maybe makes us more accessible to the general retail American investor public. And it was just something that stuck with me from 2013 that

it was possible the wealthy the elite the very connected with the great tax advisors and attorneys around them all the time could do it but how does the regular person do it so like any good fintech person you create a digital platform that makes a formally very complex and difficult process easy and accessible online to a much broader base of the US population that’s what I did in rocket

Cody Crabb (14:29)
Yeah,

so give me a little, what exactly is Rocket Dollar for? What does it do? Is it just about education or do you do other things as well?

Henry Yoshida, CFP (14:38)
So there is an educational component to our site. So the large majority of our traffic are people coming there that are just reading the articles and the questions that we answer there. And that’s what gets sort of recirculated on the Reddits through like search engines. And then obviously now more through chat GPT and Claude from Anthropic. But. ⁓

But by and large, our actual customers go there. People can sign up and open an IRA. So opening an IRA at RocketDollar is no different than opening an IRA at any brokerage house. It’s an online intake form that takes two to three minutes asking for your personal information because an investment account has to be tied to an individual. And once that’s established, you have the ability to do a transfer from an outside IRA or

old 401k in the form of a rollover into the rocket dollar account. And once the funds are there, if you have a private or alternative investments you want to do. So in your audience’s case, Cody, it could be real estate or a syndication, or maybe even private lending to a real estate, real estate developer, then they can actually use the funds inside of this new rocket dollar IRA to then go make those investments or lend that money from a private perspective to do that. And, and we just kind of made it easy. So we like to think of ourselves as we’re the fidelity for.

in alternative investment IRAs.

Cody Crabb (15:50)
Wow, that is a succinct, ⁓ awesome explanation there. And I think ⁓ it’s important too that you’re pointing out that this is not just a Rocket Dollar thing. This is a thing that if you’ve got the right setup, just about anybody could do this with whatever kind of IRA, ⁓ self-directed IRA.

Henry Yoshida, CFP (16:07)
Exactly. We’re not the first company to do this. People have done

this. there are, I mentioned there’s $46 trillion roughly in overall U.S. retirement accounts.

There’s close to 500 to 600 billion that sit inside of these self-directed or alternatives capable IRAs currently. We’re one of the companies in the space. like to think that, you know, we started in 2018 with really the idea that we should make it easy for the customer. We should put the power in their hands and we should leverage the, um, the ability to use technology in setting up, managing and deploying funds, uh, for inside of that account. Whereas I I think the other ones are more built on legacy processes.

Cody Crabb (16:24)
Mm-hmm.

Henry Yoshida, CFP (16:45)
So, you know, I think in a lot of businesses, you don’t want to be the first one, right? I mean, Google wasn’t the first search engine, but they basically crawled over the backs of every other search engine to make improvements and dominate that particular space. They were roughly the 77th search engine that was actually created, but they’re the ones that everyone knows today. So, but.

Cody Crabb (17:02)
I don’t think I knew that. That’s pretty amazing actually.

Henry Yoshida, CFP (17:06)
You know, on the rock and our side, when I created the company was really thinking about like, how do I make this easy for the customer? Like, how do I make opening an IRA that can invest in alternative investments like real estate just as easy as opening an IRA to then go buy an index fund or a public stock and then work backwards from there.

Cody Crabb (17:22)
Yeah, so okay, so

yeah, yeah, okay, so I guess here’s my question. So who should be, who’s listening to this and who’s a really good fit to, who should be doing this like yesterday and who is maybe not as good of a fit?

Henry Yoshida, CFP (18:16)
So if you’re just starting in your investment, again, having a self-directed IRA or alternative capable IRA is a product in the investment space that you graduate to. Very similar to real estate is not the first type of investment that someone does when they’re just getting started investing, right? Because it doesn’t work if you have low or no capital to begin with. So rock and dollar customers or the demographic that buys it are folks who probably have had success and accumulated savings in traditional IRAs

401ks throughout their careers and their lives. They’ve gotten to the point now where they feel like they’re a little bit overly concentrated in stock market investments, right? Because wherever they have that IRA 401k, it’s most likely that they’re only allowed to invest in a 401k. These 20 mutual funds are in an IRA.

all these publicly traded stocks, index funds or mutual funds, and that’s it. So people may look at that and say that, you know, that’s a lot of my eggs in one public equity or public bond basket right now. Maybe I want to diversify. Maybe I want to open a rocket dollar account and take half of the account and then go seek out private and alternative investments. So if they’re a part of this community, they’re here because they’re an experienced real estate investor or they’re trying to learn about investing in real estate.

Now, the problem may be that not everyone listening all of sudden has $60,000 to start investing in real estate, but now they realize that they could tap into a portion of an old 401k, which then allows them to have that 60,000 saved up because they have 300,000 in old 401ks and IRAs at Fidelity and an old retirement account from a job eight years ago that they never moved.

but spent 11 years there as an example. So that person might take 10, 20, 30 % or 50 % of their accumulated savings and open a new type of IRA that allows them to go into private and alternative investments. So that’s what we see. And the average customer with us has about $157,000 in their account. So definitely not someone who’s just starting out, but also not an unreasonable amount for someone who’s saved for 15, 20 years inside of a 401k. They would have accumulated much more than that.

Cody Crabb (19:52)
Yeah.

Yeah.

Henry Yoshida, CFP (20:17)
just by doing a 10 % or 5 % contribution of the salary plus employer match and now they’re just diversifying. mean

You know, the biggest risk right now is that if the stock market goes down, it goes down. If that’s where all your money is then, and you might need it. So if you’re in a position where you got to, you were retiring, it’s 2026, but then another COVID pandemic were to start and you see a 40 % haircut on the stock market overall in the first year of your retirement, that first year of retirement, you withdrew the equivalent of a hundred thousand dollars to actually net 60.

Cody Crabb (20:49)
Yeah,

that’s not ideal. Yeah, I see what you mean.

Henry Yoshida, CFP (20:52)
It well, and

that’s a, that’s a financial thing where the timing of when you retire or the timing of when you buy real estate or the timing of when you’re born or the timing of when you start investing actually has, you know, market sort of impact on your overall return, right? Someone who retires.

Cody Crabb (21:10)
Yeah, as a millennial, I

very much feel that, yeah.

Henry Yoshida, CFP (21:14)
Exactly.

Depending on your age, can always see. There were a lot of people, we probably have friends who maybe they happened to graduate college in the year 2020. That was a tough year to try to enter the job market when no companies actually had any employees coming in, much less new ones that they hired. Remember hearing the stories of how all the job offers that were made to seniors in college throughout the country were rescinded because why would the companies hire anyone? They couldn’t even go to their office. Bad timing.

Cody Crabb (21:27)
Yeah. Yeah.

Exactly, it’s,

yeah, I graduated in 2010. So it was very like, kind of still in the aftermath of the, yeah, so it ⁓ can be a lot, a lot can be out of your control, but like you said, the diversification here sounds like a really powerful tool to kind of keep things a little more safe and balanced. and there’s just some, it sounds like there’s just a massive amount of capital sitting in these accounts. So like, do you think this is gonna be something that,

Henry Yoshida, CFP (21:44)
You’re right after the credit crisis.

Yeah.

Cody Crabb (22:05)
over the next little while, like people are gonna start getting wise to this and tapping into it and what effect do you think that’s gonna have?

Henry Yoshida, CFP (22:11)
So people will and it will have a massive effect because right now you think about it that unfortunately it’s going to have a negative effect on the stock market because you’re talking about $46 trillion in retirement accounts of which 99.3 % is currently invested in stocks and bonds. And these are U.S. accounts only. So we tend to invest very domestically. So we’re not a country that invests 50 % here, 50 % international. We’re a country that invests 97 % in the U.S. and maybe 3 % non-U.S.

right? Because we’re the stock market that everyone aspires to invest in.

Cody Crabb (22:41)
Yeah.

Henry Yoshida, CFP (22:45)
So if this money gets redeployed, it will be removed from the public capital markets and redeployed into the private market. So if it goes into real estate, let’s just say it’s real estate and let’s say it’s a 20 % move. Well, that’s an $8 trillion move into real estate that’s not held by institutions that make like, you know, cutthroat decisions, $100 billion at a time. It’s going to be made by hundreds of thousands of investors buying one property at a time up to a fourplex.

Well,

that’s a stable that’s a pretty stable base to be purchasing these properties. And now all of sudden you got owners owning them as investments. It’ll have a massive, massive ripple effect. you know, what I think will happen in the next 10 years, and this is where I’ve given lots of comments on are that the amount of retirement dollars that will be allocated and invested in private investments will be not the one to 2 % that it is today. It’ll be more like 10 to 25%. And that effect will be the very similar to we think back in

2026 and I just flew I made it out thankfully from LaGuardia yesterday in the massive like TSA pre-check lines and and security lines but

Cody Crabb (23:47)
yeah.

Henry Yoshida, CFP (23:49)
You think like 10 years ago that you used to see a certain number of people drive to the airport, park their car and or pick up people. Well, what percentage of that has gone away? Because now, even if you’re going to visit your family, it’s just as easy, if not easier to actually order a ride share and just walk to that section of the airport. So the ripple effect that it’s had on the number of cars coming in and out, or maybe even the number of cars just overall being purchased in major urban areas. I mean, we’re not talking that it went down by a couple of percent.

went down by double digit percent and probably still continuing to accelerate at this point, right? So the number of people or the percentage of people investing in things like real estate and private companies out of $46 trillion, if this number goes from 2 % to 5%, that’s a massive effect. If it goes from 5 % to 20 % in 10 years, that is a massive colossal effect in the way American investors hold assets.

Cody Crabb (24:21)
Hmm.

Yeah, wow.

Yeah, for sure. So it sounds like you might be hearing about this in the early days, at least of it being kind of more public knowledge. So ⁓ that sounds like this is absolutely at least something to look into for your investment portfolio and to kind of see what options you have. ⁓ So if someone wants to explore this, they want to learn more, ⁓ where would you advise them to go? Obviously RocketDollar has got some stuff, like you said, it’s got some education. So where should they go specifically?

Henry Yoshida, CFP (25:10)
Yeah.

So the website is rocket dollar dot com. So R O.C.K. E.T. dot com. So that’s that’s the best place to go. There’s a lot of information there. And then when when the show publishes, you know, we even have a discount code for sign up for people to use if they choose to. Yeah. So since we don’t manage the investments, Cody, the other thing that makes us a little bit unique is that we don’t charge a fee for what you have invested in your account. So we basically just charge a flat dollar fee. So whether you have

Cody Crabb (25:28)
awesome.

Henry Yoshida, CFP (25:42)
$10,000 in your account with us or $200,000.

you pay the same price because we’re only facilitating the creation, management and deployment of funds in your account. What people choose to invest in is up to them. So we’re not in a position to charge management fees on an investment that you source, manage and operate going forward. that’s, just kind of a, I think it’s a fairness thing that we talk about that we’re a flat fee provider. That’s one of the things that we’re known for, but all the information’s at rocketdollar.com. then people, ⁓ I speak a lot. out there in the public for the company as the person

who created it at Henry Yoshida, you could just look me up and I talk about it a lot. So today I talked about how people might try to take more chances to accumulate more in retirement savings through diversified asset classes because we don’t know what’s going to happen with healthcare costs in retirement for you. So I think since it’s not something you can plan for, you can plan today to just try to make sure that you have more money in diversified asset classes. That way you don’t have to liquidate one at

wrong time. So as we speak today, the S &P 500 is down 6 % year to date. So if you have a major cost in retirement that required you to liquidate some of your investments today, if you liquidated one of the ones that’s already down right now, and because it’s the only one you have, public stocks, you’re actually going to liquidate probably more than you want to. But let’s say you had another investment that would zag when the stock market zigs, then you can liquidate from there at a higher point.

and not tap into as much of your principle.

Cody Crabb (27:16)
Hmm.

Yeah, that’s also a good call out. Well, I really appreciate you sharing this with us. I think this is gonna be a really good ⁓ episode for people to kind of get some more options on their plate. ⁓ Henry, thanks so much for joining us. Again, we appreciate you giving us some of your time. And for all you listeners out there, if you enjoyed this episode and got something out of it, which I’m sure you did, please go ahead and subscribe to the channel ⁓ so you can get more episodes like this and hear more conversations with awesome people like Henry.

Henry Yoshida, CFP (27:17)
That’s the way we look at it.

Yeah.

Cody Crabb (27:45)
Thanks one more time for joining us today. We really appreciate it. And we’ll see you guys next time on the next episode of Real Estate Pros. Bye everybody.