Democratizing Alternative Investments: The Future of Tax-Advantaged Retirement with Rocket Dollar's Henry Yoshida

0:02John Lee Dumas:Who's ready to rock today, Fire Nation? JLD here and welcome to Entrepreneurs on Fire, brought to you by High Level, the all-in-one sales and marketing platform. Today we'll be breaking down, democratizing alternative investments, the future of tax-advantaged retirement. And to drop these value bombs, I brought Henry Yoshida in EO Fire Studios. Henry is a CEO and co-founder of Rocket Dollar, leading innovation in self-directed retirement accounts that unblock alternative investments and tax-advantaged wealth building opportunities for everyday investors. And today we talk about that tax-advantaged wealth building, the future of retirement investing beyond stocks and bonds, building fintech platforms, and oh, so much more.

0:44John Lee Dumas:And a big thank you for sponsoring today's episode goes to Henry and our sponsors. Stop duct taping your business together. HighLevel runs your website, your funnels, email, automation, scheduling, payments, and memberships all in one place. And when you sign up at highlevelfire.com, you get a 30-day free trial plus my exclusive bonus stack that includes weekly office hours with me and much more. Visit highlevelfire.com, highlevelfire.com. Fire Nation, are you ready to build something special in the next 50 days? Check out my free YouTube series, 50 Days to Something, short and strategic step-by-step videos by me, JLD.

1:23John Lee Dumas:On day 50, you'll have a valuable asset. And the best part is it's completely free. Visit eofire.com slash YouTube and start day one today. Henry, say what's up to Fire Nation and share something that you believe about becoming successful that most people disagree with. I think most people disagree. They think that to be successful as an entrepreneur, you have to be a risk taker. I've never really bought into that. I'm case in point. I don't think I'm a risk taker. I think I'm a very measured person. And I think that's actually been the reason why I've been successful as an entrepreneur. Fire Nation, today we're talking about democratizing alternative investments, the future of tax advantaged retirement.

2:09John Lee Dumas:And I want to talk about tax advantages, wealth building specifically, Henry. So how can individuals use IRAs and solo 401ks as well to build wealth more efficiently and keep more of what they actually earn? I'm going to answer this in a way that probably most people in my position wouldn't answer. The people in the financial world do offer these accounts. But I'm a believer also in that it takes money to make money. and the funny thing is the system is set up in in america with iras and 401ks that's where the average american has their money the only difference is that people think that that money can only be kept in public stocks and bonds but we have a system that incentivizes people to put money into these accounts and they accumulate over time with great tax advantages and sometimes even your your boss or your company kicks in money and now all of a sudden you have a pool of it.

3:04So when you use a rocket dollar account, you get to access the money that you already have to go into private and alternative investments, things that you control, things that you source that might have a chance for better return or better personal connection to you or something you might be more passionate about and get to keep those tax benefits and continue to grow that wealth. So you use the money that you already have to then make more money by investing in things that you know about and you believe in.

3:28John Lee Dumas:I want to talk about the future of retirement investing specifically? Because with technology and regulation evolving fast, and I mean, we mean lightning fast, how is the retirement investing landscape changing? The landscape is changing just because the ability to learn about and access investments that might have previously only been available to the largest institutions, the wealthiest individuals, and the biggest and baddest like private equity firms and investment banks are now becoming more accessible to what I would call the retail average American investor. And that allows us to essentially participate in the investments that normally were reserved for only the super rich and the super wealthy.

4:13And the reason why they were reserved for the super rich and super wealthy, and they guarded that is because it, quite frankly, generated better returns over time. And now regular people can participate about that. And that's going to change the retirement landscape. And we have a government regime that's starting to recognize this and allow folks to get into these types of investments using retirement accounts as well.

4:33John Lee Dumas:So can you maybe give us a couple of your favorite examples over the last maybe one to two years where you're like, oh man, this wasn't available, you know, five, 10 years ago, but it is now. What's ended up happening is the people who pull these capitals. So let's say the titans of private investments. So think like hedge funds or private equity firms. They always were able to count on only being able to raise money or needing to only raise money from large institutions and other wealthy individuals and organizations and companies and so forth. But they realized that that that pool of capital is actually run a little bit dry and they need to expand who they accept money from.

5:09So they've now accepted money or are accepting money from regular folks. And that that's just been a dynamic change where we're actually the average American investor. So when I say we, I kind of lump myself into this as well, is that we're in a position where the people who actually run these investments need us more than we need them. And that's what's changed the dynamic of retirement investing, where this pool, John, has forty seven trillion dollars held by us, the regular Americans. So you can best believe that the people who are running investments recognize and understand that there's a massive pool of capital that they need money from more than we need money from them.

5:48John Lee Dumas:Now, on that massive pool of capital, let's talk about going beyond stocks, about going beyond bonds. I mean, what role do real assets, we're talking real estate, we're talking private equity, what role do assets like that play inside a modern retirement portfolio? The role they will play is that they are becoming the new asset class or the new investments that basically move not in lockstep when your public investments don't go in the direction you want. So in the past, probably up until the turn of the century, you always heard that you could balance your portfolio by investing partially in bonds and then partially in stocks because they didn't move in lockstep with each other.

6:31Well, in the last 25 and a half, 26 years now in 2026, that actually mathematically hasn't been the case. So to have a well-diversified portfolio and be successful over the long term, whether you're a large institution or whether you're an individual saving for retirement, you have to have investments that will zig when the market zags. And that's what private investments are now offering to the retail average American investor inside of their retirement account through providers like RocketBeller.

6:55John Lee Dumas:So let's talk about specifically real estate because I think a lot of my listeners, they resonate. They maybe understand on some level real estate. They've probably made a couple of transactions, maybe their current home, maybe an investment property. I mean, who knows? But I mean, what specifically are you excited about in the world of real estate in 2026 and beyond? I think that 2026 and myself. So I'm a pretty avid private investor, so I invest in a lot of private things. Real estate's one that I've been focusing on because I think it's actually one of the better buying opportunities right now.

7:28So I would say that that 2026 probably represents a better buying opportunity in the real estate space for people who are in a position to have money and ability to do deals than at any time in the last 15 years right now. So you're going to you're going to be well served investing in real estate. So to answer your question directly, I think it's just that it's a great opportunity to buy while there are a lot of people wanting to sell, a lot of people wanting to get out. And if you have cash and you're in a position to buy, it's a good time to get into real estate, all forms of it.

7:58John Lee Dumas:So what would be a recommended first step? Like if someone's like, okay, I'm going to take, you know, Henrietta's word here and start looking into this. Like what do you like to recommend your clients do if maybe they're treading into the real estate universe for the first time? If they're treading into it for the first time and then using, let's say, some retirement dollars to do it, there's lots of opportunities to find people that you can invest alongside with who are running those deals. So in other words, you become a passive limited partner in the syndication deal. So and those are a couple of reasons why I'd probably recommend you start there to go look for these types of syndications.

8:34One, you could start to look in your local community. You could find people who are pulling capital to buy things like apartment complexes or commercial office buildings. or maybe a portfolio of houses or just one specific real estate development deal. So you can stay local, an area that you might have particular knowledge because you live there. And then two, you're not the one actually trying to put up all the capital for a particular deal and then run it yourself. So you might be able to access and be a part of a syndication for as little as$10 ,000 or$25 ,000 or$50 ,000. And you'll get a payout on the real estate on the back end.

9:04But usually these deals are structured as well to give you an income stream in the meantime. So you get the comfort of knowing that you're going to get a little bit of an interest or a dividend check with the potential when the property actually or the deal sells out to get a return above and beyond your invested capital.

9:20John Lee Dumas:Fire Nation, we're going to talk about opening access, building fintech platforms, innovation and retirement planning and more when we get back from thanking our sponsors. If you've ever tried to secure a traditional bank loan for your business, then you know the process is slow, complicated, and it rarely moves at the speed you need. In between increasingly strict lending requirements and a growing number of obstacles, you're often stuck waiting right when you need capital now. That's why I want to tell you about Revenued. Revenued is built for small business owners who need fast, flexible access to working capital without relying on your personal credit score.

9:56John Lee Dumas:Instead, they look at your actual business revenue. with the Revenued Flex line. You can access funds in as little as one business day, and as you pay it back, your available capital replenishes, so it's there when you need it. Now, this isn't your traditional bank loan. It's designed to flex with your business, and that's exactly why over 10 ,000 business owners are using Revenued to keep things moving. There's a reason Revenued is rated excellent on Trustpilot with 1 ,000 five-star reviews. Give your business the flexibility to handle whatever comes next. Apply now at revenued.com slash fire.

10:26John Lee Dumas:That's revenued with a D dot com slash fire. Apply today and be ready for whatever comes next. Fire Nation, ideas are exciting, but systems will allow you to create freedom. That is where High Level comes in. High Level allows you to build and run your entire business from one platform. Website builder and hosting, funnel and landing pages, email marketing, automation and workflows, calendar booking, payments and subscriptions, even course and membership hosting. Everything works together seamlessly. Plus, award-winning 24-7 support so you are never stuck. And when you go through my link at highlevelfire.com, you unlock my full bonus stack.

11:04John Lee Dumas:A 30-day free trial of High Level with full access. A private 15-minute coaching call with me. Weekly live office hours with me. A digital copy of my book, The Common Path to Uncommon Success. My 50 Days to Something execution roadmap and more. Stop piecing tools together. Start building momentum. Visit highlevelfire.com and start building your something today. Henry, we're back and I want to talk about opening access. How are alternative investments being made available for everyday people who traditionally didn't have access? How? So one, you needed an environment, a legal environment that was friendly for folks to actually take tax-advantaged monies to go into private investments.

11:51So that's been happening. And this isn't just the current administration. This actually started in prior administrations when it was opposite side of the aisle president in place. Number two, and this is not the part that I function in, is that there are a lot of innovative fintech companies who are basically democratizing these previously private, previously institutional only investment asset classes to become available to retail investors. So what I like to say is that there are a lot of people who are probably smarter than me, more creative than me, who have decided to make access to private late stage private company stock, real estate, big investments available on a technology platform.

12:31The part I work on is the providing of capital. So people always say, hey, that's great. There's a platform that exists. I can invest$100 or$1 ,000 or$10 ,000 and get into this private deal, but I don't have the money lying around to do that. So that's where I come in and I help people unlock the money that they already have to go into these other smart fintech providers who democratize basically the asset classes and chop them up and made them available in$101 ,000 and$10 ,000 chunks.

12:58John Lee Dumas:Let's talk about building fintech platforms. I mean, what does it take to build and to scale an innovative fintech platform in the retirement space today? And I think that's the key word, in the retirement space today. I think that it helped me a lot that I came from the industry. So I think that sometimes people think that all entrepreneurs, they go into an industry because they have completely fresh eyes and no preconceived notions. But I think when you're dealing in a regulatory environment, overlaid with the very personal part of handling people's money, it actually helps to have a good contextual understanding of the existing incumbent systems and protocols and the way things have been done in the past in place.

13:42But then maybe look at it from a different angle, like, you know, just position yourself a different side of the room and see if you see things differently. And that helps you develop, let's say, a framework to come in. I mean, the reason I got into unlocking retirement funds to do private investments, 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.

14:09So it kind of made me start thinking through the lens of where is capital? Where is capital held by average American people? And then basically linking that bridge back to people wanting to invest in private alternatives. But again, when you're dealing in the retirement and building a fintech company in a regulated space, I think it's actually good to have the contextual understanding of the industry, but then the open-mindedness and curiosity to potentially look at it from a different angle.

14:35John Lee Dumas:So I want to talk about innovation in retirement planning. I mean, we love talking to people who are cutting edge, who are keeping their finger on that pulse. So what new products and strategies are emerging that could literally reshape how people both plan and invest for retirement? And maybe let's start with a couple products. And then after that, let's maybe talk about it. But then let's go into strategies next. So separate those two. First off, a couple new products. You know, if someone were to create a centralized system for standardized reporting of private investments, so the thing with private investments is that unlike, let's say, 500 or a total of only 3 ,000 publicly traded stocks that are all required to go through a same government regulated system for registering, reporting, and sort of indicating the value of their shares on a day-to-day basis, that doesn't exist in the private world.

15:22So if a database, an online database that everyone had to adhere to that was standardized, if a product like that came out, probably needs to be mandated by the government. And then someone will take that and then run with it and build build that standardized platform for the reporting purposes. That would be a very helpful product. I think like a standardized reporting would actually then allow this market to really, really explode more than it already has in the last several years. So I'd say that from a product standpoint. And then the strategy is maybe less strategy and more mindset that the average American person now from, let's say, the last three generations that we've had retirement accounts, so roughly 50, 60, 70 years or so, has always been told that you basically just put away money.

16:08It just keep accumulating on a month to month or week to week or biweekly basis from every paycheck into these couple of things. And then you should be fine after 30 years. That's a mindset shift. I don't think that that paradigm is going to work anymore. I think people need to be more proactively involved, need to think about it. The times change. So when the mindset shift changes and people understand that, hey, I need to have a portfolio that includes private investments such as real estate, digital assets, private equity, as well as stocks, bonds, and mutual funds, when that mind shift change really happens at a broad scale, then people will become more investors, more empowered, and they'll have better portfolios, which will then generate better returns overall for people.

16:46John Lee Dumas:Man, I mean, we live in such crazy times, Fire Nation. I mean, you've really just got to understand what's out there in this world because there are so many opportunities that are always emerging. And that's why I love to talk with people like Henry who are, this is what they do. They wake up every day and they just stay on the cutting edge. They keep their finger on that pulse. So for someone who's looking to take more control of their financial future, Henry, what is the one step they should take today to start building smarter tax-advantaged wealth? Take an inventory. I mean, you'd be surprised, but it starts with taking an inventory first.

17:27Most people, if you ask them, they have their next vacation planned or they know where they might be going to dinner, but they couldn't tell you exactly where they might have their investment accounts or how much as a percentage or a dollar amount that they're saving on a monthly basis. So you really have to start there and get a good sense of where you are today before you make that next step. That next step might be saving more. The step after that might be making sure it's optimized into the right type of account. So let's say tax advantage versus just something that could be taxable every year.

17:56But step one, and this is necessary, it might sound elementary for the folks who say that they've already done this, but I can tell you right now, a lot of the audience, even the FIRE audience, it's really having a good inventory and understanding where you are today before you do anything else.

18:10John Lee Dumas:FIRE Nation, this is powerful stuff. And again, if you can get ahead of this, especially when you're younger, I mean, the compound results are super powerful. So, Henry, of everything we've talked about here today, and we've talked about a lot, fintech platforms, retirement planning, stocks and bonds, retirement investing, what is the one single takeaway that you would want our listeners to have from today's conversation? I think the one takeaway is that if I basically leave everyone with the idea that they should take a little more control, a little more empowerment, and just a little more proactive steps towards making sure that they're sustaining themselves for the future, by taking a little bit of time today, then I'm really happy.

18:53Like, I'm usually the guy where people will come up to me years after they heard me talk and they said, you know, you were the guy who told me to look at my old accounts. And I, sure enough, I did that. And I'd forgotten about a$30 ,000 account that I then reinvested into something else, did really well in that investment. And now it's a six figure amount. Um, uh, I asked for my cut and I never, I've never gotten the cut.

19:14John Lee Dumas:Well, speaking of your cut, I mean, if fire nation wants to learn more from you, wants to connect with you, what is your call to action for our listeners today? If you're interested in learning about how private investments inside of tax advantaged accounts of which most people already have accumulated monies in. You could find a lot of information about how these accounts work, why they're why they make might make sense for you as an individual in your investment journey at our website at RocketDollar.com. That site is actually designed more as an educational site, as opposed to a site where people go and sign up and open an account.

19:50Once you're a customer, or you can manage that account. But prior to that, the vast majority of the visitors we get to the site are actually there for information.

19:57John Lee Dumas:Fire Nation, you're the average of the five people you spend the most time with. You've been hanging out with HY and JLD today, so keep up that heat. And for links to everything we talked about, visit eofire.com. Type Henry in the search bar and the show notes page will pop right up. And Henry, thank you for sharing your truth, knowledge, and wealth with Fire Nation today. Not so much wealth, but more value. And for that, we salute you and we'll catch you on the flip side. Thank you. Thank you very much, John. Hey, Fire Nation, a huge thank you to our sponsors and Henry for sponsoring today's episode and Fire Nation.

20:32John Lee Dumas:Are you an entrepreneur on fire who's looking to share your amazing message with the world? If yes, we are now accepting applications for EO Fire. So to learn more about becoming a guest, visit eofire.com slash guest and I'll catch you there or on the flip side. Stop duct taping your business together. High Level runs your website, your funnels, email, automation, scheduling, payments, and memberships all in one place. And when you sign up at highlevelfire.com, you get a 30-day free trial plus my exclusive bonus stack that includes weekly office hours with me and much more. Visit highlevelfire.com, highlevelfire.com.

21:08John Lee Dumas:Fire Nation, are you ready to build something special in the next 50 days? Check out my free YouTube series, 50 Days to Something, short and strategic step-by-step videos by me, JLD. On day 50, you'll have a valuable asset. And the best part is it's completely free. Visit eofire.com slash YouTube and start day one today.