What if the biggest mistake most investors make isn’t what they invest in — but how they invest from a tax standpoint?
In this episode, we sit down with Henry Yoshida, one of the most respected voices in retirement planning and alternative investing, to unpack the #1 tax strategy millionaires consistently use to grow and protect their wealth.
Henry pulls back the curtain on how sophisticated investors legally reduce taxes, unlock retirement capital, and gain access to alternative investments like real estate, private equity, and private credit — all while maintaining flexibility and control. We explore why traditional retirement advice often falls short for high earners, and how proactive tax planning can dramatically change long-term outcomes.
Whether you’re an entrepreneur, real estate investor, or advisor serving high-net-worth clients, this conversation will challenge conventional thinking and give you a clearer framework for building tax-efficient wealth with intention.
Episode Highlights Here:
Brett
Before we jump into this episode, I want to invite you to join our community to help you become a better steward scale to billions and ultimately give more or all of it away. All I want you to do is to click the subscribe button right now. I love your support. It’s incredible to see your comments, and we’re just getting started. I can’t wait to go on this journey with you. Thank you so much for subscribing. It means the world to me. Hello everybody, and welcome to the build to millions podcast where we guide successful entrepreneurs and investors on their journey from millions to billions. We believe the key to scaling and compounding your wealth and life starts every single day with a mindset and practice of stewardship over ownership and applying billionaire biblical principles. Our ultimate goal is to help you scale and compound your wealth and life so you can give more. Can give more all of it away to help MVPs. My name is Brett Swarts. In each episode, we are joined by some of the world’s top entrepreneurs, millionaires and billionaires, and they share their secrets, wisdom and insights with us, so we can all level up our faith, our impact and our life to make a bigger difference in this world. I’m excited about our next guest. He’s out of the great state of Texas. He’s got a really unique background. He was the CEO of rocket dollar, a web platform that lets people invest tax advantaged retirement dollars into private alternative investments. He’s a Certified Financial Planner. He also has real estate expertise and licensing, and he recently sold rocket dollar to retired.com incredible, really cool website you want to check out for sure we’re going to be talking about Bitcoin tax strategies today. Please welcome the show with me. Henry, Yoshida, Henry,
Henry
We’re doing great. Thank you very much. Glad to join you today. And looks like it’s nice weather where we both are, so Florida and Texas,
Brett
Absolutely it’s nice today before it gets too hot. And for our listeners, get to know you for the first time. Would you? Would you give us a little bit more about your story and your current focus?
Henry
Sure, ever since I graduated college, I worked in traditional finance, so I worked at Merrill Lynch, which became Bank of America, and I kind of got thrown into a division that deal dealt with tax advantaged accounts. So that’d be your IRAs, your 401 Ks, 403 B accounts of your church or nonprofit or school educational institution. And I just kind of grew up in that industry and became an expert over the years. And after I left the corporate world, I did consult in that space, and I’ve since built two products, the current company, rocket dollar, and then I built another mobile app platform for Roth IRAs. So, I guess, in a way, tax free strategies and now just sort of tax avoidance strategies and digital platforms. So that’s kind of what I’ve done now for the last 25 years.
Brett
Absolutely love it, right? You grew up in you graduate college or whatever, and then you start to go into it. All of a sudden, you figure out, oh, wait, I had the 10,000 hours in this piece of this tax code, right? These tax codes for 1k IRAs, right? And then you look up and go, all right, maybe there’s a better way to do it. So, take us to the moment when you say, okay, there’s got to be a better way to do this. And maybe going more to all the alternatives, like real estate, although I would argue that the alternatives, you know, according to Tony Robbins and his new book, is actually the alternatives, is the stock market right, and private equity has returned, I think, 14 and a half percent versus nine and a half over the last35 years. And so really, it should be swapped. But maybe we could talk more about that too.
Henry
Yeah, no, I think you’re right. And again, those terms, like alternatives versus like, you know, the traditional maybe it’s a little bit of a misnomer, and there’s a little bit of an aside not to do with this. But I guess in a way, if you look at me and you see me right, I guess I’d be labeled as a minority, but a lot ofttimes, in different arenas, depending on where I’m at or where I might be, you know, there we sometimes function as the majority. So again, these are just labels. But, you know, getting into it and realizing, I mean, I think I thought first that I never went into it thinking there was a better way to do these things or do the investments. I actually always geared it from the personality side, which was that I knew from working at a large Wall Street financial services institution that basically the sophisticated, large, institutional type investors were putting upwards of 50% or more of their overall investment dollars into private alternatives. Yet, in the retail investor world, access was limited. And then, even though access is getting better. Now the problem is that, well, retail investors have a lot of their money inside of these retirement accounts, so I just decided to marry the two and saying, Hey, look, the access is becoming bigger, but the access isn’t going to matter if the capital that is held by retail investors can’t go into it. So that’s how became the genesis of rocket dollar and me creating a digital version of a self-directed IRA.
Brett
Yeah, by the way, if people want to learn more right now about Henry and everything, he’s doing, just go toretired.com retired.com so if you like this little, short clip of the interview I just did, click over here to watch the full interview, and please don’t forget to subscribe. Thanks so much, everybody.
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About Henry Yoshida
Henry Yoshida, CFP®, is a fintech entrepreneur, financial executive, and nationally recognized expert in retirement planning and alternative investments.
He is the Co-Founder and CEO of Rocket Dollar, a leading financial technology platform that empowers individuals to invest their retirement accounts into alternative assets such as real estate, private equity, startups, and more — moving beyond the limitations of traditional Wall Street portfolios.
Prior to Rocket Dollar, Henry founded Honest Dollar, a venture-backed retirement platform that was acquired by Goldman Sachs, as well as MY Group, an investment advisory firm with billions in assets under management that was later acquired by Captrust. Earlier in his career, Henry spent nearly a decade at Merrill Lynch, building deep experience in wealth management and financial strategy.
Henry holds an MBA from Cornell University and is a Certified Financial Planner™ (CFP®). Today, he also serves in executive leadership roles within the broader retirement and financial education ecosystem, helping individuals and families make smarter, more flexible decisions with their capital.
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