Henry Yoshida on Building the Future of Retirement Investing

🎯 The ONE Thing You Need to Know

Asset LOCATION beats asset selection. Stop obsessing over what to invest in. Focus on WHERE you save first: 401(k) with match (instant 100% return) → IRA (tax deduction) → Taxable account.

Guest: Henry Yoshida

Founder of Rocket Dollar | Former Merrill Lynch (10 years) | Finalist at major fintech competition (judged by Shaq!) | Acquired by retired.com

💰 What is Rocket Dollar?

Platform for investing retirement funds in alternatives: real estate, private equity, crypto. Think Uber for retirement investing - it sounds crazy until it becomes normal.

🔥 Best Quotes

• "Company 401(k) match = instant 100% return. No investment beats that."
• "My parents lost everything starting a restaurant. Now I help people retire rich."
• "Consistency beats motivation. Be pretty good most of the time."
• "You're not someone who doesn't smoke. You're a non-smoker. Identity = habits."

📚 Must-Read

Atomic Habits by James Clear - Remove friction, build identity-based habits

Action Items

1. Max out 401(k) match (free money)
2. Open/fund an IRA
3. Stop researching perfect investments - just start
4. Remove friction from savings (automate it)

Connect

🌐 rocketdollar.com
 📱 @fitfinancehenry
 💼 LinkedIn: Henry Yoshida

Tags

#retirement #investing #fintech #passiveincome #wealth #moneytips #financialfreedom #realestate #crypto

Transcript

Rob Pene (00:01.572)
Alrighty, God bless everyone. Thanks for joining us. Appreciate Henry Yoshida joining the call today. I'm excited to dive into some personal finance, but also just overall wellness because financial things usually is the cause of a lot of people's stress. So how to manage some of those things is what I like to chat with Henry about. But before we get started, what's gonna kick start,

kick off the conversation today is this one question that I'm curious about. It's, if you were to reflect back in the last 12 months of your life and you were to turn that into a Netflix special, how would you describe that movie in the last 12 months?

Henry Yoshida (00:53.646)
Let's see, so Netflix, maybe instead of movie, last 12 months I'd probably go with, and this is classic, I had to turn it down yesterday, but I love that genre. I couldn't go because I had a kid's obligation, I'm getting to the point here, but I got offered a free ticket in a suite to go see Ice Cube last night, but couldn't go with a buddy. Yeah, he has a client, he's a financial advisor for NFL football players. The guy didn't make...

Rob Pene (01:14.315)
Whoa!

Henry Yoshida (01:22.562)
because it's like I canceled for weather reasons so he had an extra ticket invited me but it couldn't go because I had a thing but that's the same genre same time frame and I guess Ice Cube is still kicking and doing well and apparently touring but I'd probably say that for me maybe the theme is more of a song like it'd be sort of like that that great video I'm gonna knock you out so hello Cool J in the chorus of that one so you know yeah

Rob Pene (01:33.272)
Yeah.

Rob Pene (01:44.644)
Yes! Yeah!

Henry Yoshida (01:47.982)
The point being this specific line that I think about for the last 12 months for me is that, you know, he's been here for years. He's just maybe kind of coming out, but he's been here for years. And that's maybe what I think about, at least for me personally and professionally in the last 12 months. A lot's happened to me in the last 12 months.

Rob Pene (02:03.53)
Yeah, yeah, let's jump into it. So Rocket dollars pretty big, pretty impressive. And then the retired.com, that's nice, right? And they're all within that finance space. But then you also mentioned earlier off camera, where you're diving into Instagram only for your personal brand. Yeah.

Henry Yoshida (02:09.858)
Yeah.

Henry Yoshida (02:14.541)
Yeah.

Henry Yoshida (02:25.205)
Yeah, I mean, I guess I probably have one, but it's probably more limited to LinkedIn. So just, you know, a new project that I started here midway through the year, actually maybe midway through the summer. And now we're right at the beginning of the fourth quarter. So, yeah. And so on that part, the rockandor.com is my company that I started in 2018 and in last year. So this was right outside of that 12 month window, but we took an acquisition.

offered to be a part of the retired.com brand of company. So that's my parent company. And my CEO there, we'd met years ago and kind of consummated a deal just many years later for my company, Rocket Dollar, to join as a part of his brand. There's other companies under this retired.com brand, but it's big company.

Rob Pene (03:12.93)
Yeah. Now, were you always interested in the finance side even growing up? Like, what's the story behind all of that?

Henry Yoshida (03:20.94)
Well, actually I wasn't. plan was, I didn't know any better. So I was the children of immigrants, know, my, my parents immigrated they from Japan. They never went to college. They met here in the United States and California where you're based. And eventually kind of ended up moving to Texas when my brother and I came along. So when we were born and like a lot of Asian American immigrants who didn't go to hire, who didn't come to the United States for higher education, there's two different types in my view.

The ones that didn't, a lot of them went into the restaurant industry. So my parents were both career restaurant employees. and you know, that, that upbringing, you don't know a lot about like, you know, what's the track? Like, what do you study to go become a lawyer or become an engineer? I didn't even probably know what an engineer was to be quite frank. You know, when your parents work in the restaurant industry, you know, you don't have, they don't work in some big company and so forth. So my plan was actually thinking that I would become a lawyer. That's what I wanted to do when I went to college, but

I went into college not really knowing what that actually meant either. It just sounded kind of sophisticated. You got to wear a tie, wear a tie and a suit and have a downtown office and so forth. when I finished my undergrad at the University of Texas, didn't have the money to continue going to school. Law school was additional graduate school for three years and just took a job to save up some money instead. That job was at Merrill Lynch. And that's when I got introduced to, you know,

Rob Pene (04:36.484)
Mm.

Henry Yoshida (04:47.672)
financial services, personal finance, and then my particular specialty or area of specialization was corporate 401k and tax advantaged IRA and 401k type plans for individuals and small businesses. And that part really kind of connected with me because that was a way to work within financial services without having to just try to go get really, really rich people to become clients of the firm. Of which, you know, I didn't really know anything about that world either.

Rob Pene (05:13.272)
Mmm.

Henry Yoshida (05:17.006)
So it aligned with I got to do my job in financial services and I ended up loving it never going back to law school I mean, maybe I do that someday When I'm retired I joke around that I will go to law school one day But I'm gonna wait till my daughters go to college and we'll pick one of them. I'm gonna go to the law school after college so that To age me even further it'd be like that old Rodney Dangerfield movie where he ends up like going to college when he's like seven years old where his son's at college, know, and his son hates it because

Rob Pene (05:44.824)
Congrats Paul and

Henry Yoshida (05:44.834)
dad's cool and rich and has money and was able to have fun at college. So, so I always threatened that I'll go to law school where they go to college. Then that'll be my retirement plan. But, but yeah, I just ended up falling in love with the idea that I can work with them financial services, but actually give advice to, you know, what was more like mainstream middle-class Americans, just trying to establish that foundation for retirement. And then I always think about my parents that there was never anyone to tell them to

Rob Pene (05:53.218)
That's funny.

Henry Yoshida (06:13.96)
away a little bit of money into an IRA every year and had they done that or had they known to do that, they probably would have, right? You know, how different life might have been, you know, for them. And I think to myself as I've gone through my career that I've been sitting at the front of these break rooms, you know, giving out free. I'm in Texas, so breakfast tacos a lot of times, maybe donuts some of the time, but mostly breakfast tacos, just to get people to come to the meeting and thinking that there's going to be someone in this room.

Rob Pene (06:14.052)
Yeah.

Rob Pene (06:32.228)
You

Henry Yoshida (06:42.274)
Who's going to say, you know, this guy seems decently credible. I'm going to put away 10%. And then maybe they just forget that they did that. And 30 years later, they're going to look back and say that it was literally the best decision I've ever made in my life financially. Like hands down, number one, I don't even know when I started, just did it. It was best decision. And I always think to myself, like, what if, what if someone had told my parents to put away a little money in an IRA? The restaurants didn't have a 401k.

Rob Pene (06:56.26)
Yeah.

Henry Yoshida (07:10.902)
and so forth. So that's what I really loved about the financial services.

Rob Pene (07:15.234)
Yeah, in your experience, why is it so like almost like a stretch for people to think retirement? And there are just a huge pocket of people in America that don't have it, you know, and there's...

Henry Yoshida (07:30.402)
Well, that's, that's, there's an easy answer to that question, right? I mean, as Americans, we're all focused on the problems that we have right now. Like, you know, while I'm talking to you, my, my most immediate problem right now is that, I sat down and made myself a cup of tea to be able to have this conversation with you. But dang, I probably could have also gotten a glass of water, but now I can't get up cause I'm sitting down to talk to you. Number one, most immediate problem. So you think of what's near to you. the one after that is that.

Rob Pene (07:38.498)
Yeah.

Henry Yoshida (07:59.63)
Is it my turn to go pick up my daughter from school today or is it my ex's? I can't remember. I need to go look at my calendar that kind of thing. So so when you look at the things of Items that everyone needs to worry about as a normal American person human being in today's digital and in fast-paced society Retirement is one it's like so far out in the future and it's so far down the line of the things that are immediate for you right now so people don't think about it, which is why

I think I made a career of telling people that look, that is a hundred percent true, which is why you just basically do one thing towards it and kind of let it go on its own, which is just fill out paperwork or fill up the online form. Maybe put a little bit of money away, whether that's 1%, whether that's $10, whether that's a hundred bucks or whatever you can do, on a, on per paycheck basis, monthly basis, weekly basis, whatever that may be. And then go focus on.

damn I should have gotten that water or whose turn is it to go pick up the kid here on a Friday afternoon and so forth. So that's the answer to question. That's why it's so far down the line of things and we have to focus on like what's immediately out of this right now, right? It's Friday so you're probably more thinking about what you plan on doing for fun tonight in this weekend than you are putting away money that you're not gonna use for 25 or 30 years.

Rob Pene (08:59.299)
We're on it.

Rob Pene (09:19.98)
Yeah, yeah, yeah. Now with RocketDoll, it sounds like the tool and the business was built to actually serve the function of solving that problem, right?

Henry Yoshida (09:30.454)
So it was, the tool of RocketDollar itself probably solves a different problem for people that are already investors. So I'll step back, but RocketDollar itself, I've worked in the early part of my career with just regular 401Q plans for small businesses and getting people enrolled and helping to manage the plan, deciding what investments are in there and getting hired by small size companies first and mid-size companies and large companies later in my career. And now at RocketDollar,

examining the space, we are a company that provides IRA accounts for individuals to invest in things that are not stocks, bonds, and mutual funds. So the people that use our tool now are the ones that have accumulated a pretty good size amount of money in the public stock markets. And they realize that, hey, I'm pretty over-concentrated here. Maybe I should look at some things that aren't stock markets. what are some investments that would zig when the stock market might sag?

Rob Pene (10:18.916)
the

Henry Yoshida (10:29.614)
You know just in case because if I have everything there and things go down right then I'm completely exposed so You know I define as people once they get to a certain level of asset Investable assets that maybe it behooves them to go look at things that are just not stock market and rocket dollars an IRA platform that allows you to have an IRA that Let you invest in things that are not stocks bonds and mutual funds so private investments real estate private equity cryptocurrency

Those are the things that our customers can do in an IRA account. So that's the tool and the product we offer today at Rock and Dollar.

Rob Pene (11:04.952)
Yeah, when you're at the beginning of launching the business, evangelizing about the mission and the function of the tool was huge. So you had to kind of tap into that personal interest of sharing with people. How did that happen? Like, was it gradual where you just had to get on podcasts and tell people, did you go to different...

networking things to speak, how did you kind of evangelize the overall mission?

Henry Yoshida (11:36.846)
In this case, you're coming up with the idea. So the name Rocket Dollar itself has a meaning. It was a domain that I purchased in 2016, so two and a half years before I started the company. And then the idea was to connect that, you know, people are somewhat limited with their money. So when their money is in an IRA or 401k, they can only invest in mutual funds usually or individual stocks or bonds.

Rob Pene (11:50.454)
Mm.

Henry Yoshida (12:04.526)
So it was limiting and the idea was that obviously that was your money. So the idea behind rocket dollar was that you could go a lot further and a lot more adventurous places in a rocket than you could on a bike or in your car or just walking there and then obviously the dollar side of it and I had the domain since 2016 because I had a prior company called Honest Dollar. So I had a lot of something dollar domains and I built a built a retirement focused technology investment product.

Rob Pene (12:28.291)
Yeah.

Henry Yoshida (12:33.482)
under that name as an online platform and that company got acquired as well. But that was the genesis for the RocketDart. But the how we launched it wasn't me getting on podcasts and thinking and evangelizing it. It's that I'm talking to you here on the second half of October. At the end of October, there's a big financial technology conference in Las Vegas, the biggest one in the world.

And in 2018, I'd sold my prior startup. So in this one, I entered the startup competition. So there were 250 new startups that apply. go through judging rounds prior to the actual conference happening in Vegas. my company, my teammates and I, made it to the final 30. They got to go to Vegas and then compete. And then the final two eventually go against each other on the final stage.

Going through that process was the way that we sort of launched and told people about the company. So we had, I gave a presentation. it was, it was a neat event because the final, we made it all the way to the final two. So I came in second place. I didn't win, but I wasn't on the final stage. And the, was on the main stage at this gigantic conference. were about 3,500 people in the room. obviously press, a lot of people, and it was a startup competition with judges and the guest judge would one of the guest judges.

The other three were venture capitalists and then the fourth one was a guest judge. was Shaquille O'Neal. Yeah. So, yeah. So I got to talk to him in the green room for a little bit before. It was kind of to one chat with Shaquille O'Neal and then maybe to also tell him, know, sway like his voting a little bit, but I didn't win.

Rob Pene (14:02.461)
no way. That's cool. That's fun.

Rob Pene (14:18.596)
Yeah, yeah, that is probably super massive and tall. That's awesome.

Henry Yoshida (14:22.99)
He has massive and tall yeah, he's a gigantic individual but really nice and also savvy business person himself, too. We actually talked about You know his how many Papa John's franchises and how many five guys franchises he owns. Yeah, like He owned I think he told me several dozen at that time and now more Papa John's franchises and More than 50 55 guys franchises or stores, you know

Rob Pene (14:44.516)
Yeah, probably a lot more.

Yeah, that's awesome. That's good.

Henry Yoshida (14:52.782)
Yeah. So that it was, was like neat where I actually talked about his portfolio.

Rob Pene (14:57.464)
Yeah, yeah, yeah, he seems pretty open, you know, in the different interviews I've seen, he seems pretty open. Yeah.

Henry Yoshida (15:04.236)
Yeah, yeah. So I knew that he grew up in San Antonio, so he graduated high school in San Antonio, about 60 miles away from where I live right now here in Austin, Texas and central Texas. So we actually talked about those those days. You know, it's high school days because I knew the high school that he went to and probably maybe random people that come up and talk to him don't know that about him. He was a military kid and when he graduated high school, his dad happened to be stationed in that area, country, so he graduated from there.

Rob Pene (15:16.792)
Yeah

Rob Pene (15:21.746)
cool.

Rob Pene (15:25.154)
Right. Yeah.

Rob Pene (15:34.402)
Yeah, nice. Did you always know that you had that entrepreneurial spirit, like that curious, I'm going to build and do things? Or did that happen?

Henry Yoshida (15:43.662)
No, I didn't I never thought about it actually because You know my parents they did work in the restaurant industry the whole time, but there was one period in their life where They they left and they tried to start a restaurant on their own But the failure rate for restaurants is really high so the time the one time in their life where they kind of took their shot to be an entrepreneur and You know myself and my brother as their children watching this they they failed and you know

If anything, it kind of made me think even more about I need to go this corporate route, like be this attorney or work with this company and so forth. So oddly enough, it is kind of interesting and weird that I the way that I went in starting companies because my one taste of it through the people who were most influential in my life was just an abject failure. And it kind of made me think about and had them.

Rob Pene (16:17.421)
Yeah. Yeah.

Rob Pene (16:34.564)
Hmm

Henry Yoshida (16:38.888)
to talk to us about just kind of doing the right thing. You know, they said you're good students, make good grades, get into college. You know, maybe the school will give you some money. I went on to graduate school, so I did, I got an MBA in the Northeast. So that was kind of my first time being outside of Texas. And, it was never to think about being an entrepreneur. It just sort of happened more than anything. Yeah.

Rob Pene (16:50.967)
Hmm.

Rob Pene (16:58.232)
Wow. Now, happened while you were working in the financial services or did you stop and then did you have an itch to grow something and explore something of your personal ideas or did a partner come to happen?

Henry Yoshida (17:02.062)
Thank

Henry Yoshida (17:12.905)
Uh, yeah. So the, the 10 years I spent in financial services when I learned the business was at Merrill Lynch and I was there for 10 years. Uh, it was a very interesting 10 year period. was, started in the year 2000 and I left in the year 2010. Um, so 2000 was the, um, sort of the internet bubble bursting at Y2K fear. So technology stocks took a big hit.

Rob Pene (17:34.446)
Yeah.

Henry Yoshida (17:38.026)
I was in Austin, Texas. That's where I graduated from the University of Texas in Austin. So, you know, this town was hit pretty hard. was overindexed to technology companies and technology employees. But that part of the economy hurting actually is what got me into the 401k space. And I kept up that part of the business. then eight years later, the credit crisis actually did Merrill Lynch in and ended up

Rob Pene (17:57.517)
Hey.

Henry Yoshida (18:04.526)
getting swallowed up by Bank of America in the 2008 credit crisis. And since I was working in a part of the business where I helped small business owners and mid-sized companies. And when Bank of America took over, it actually became a little bit difficult and somewhat a conflict of interest because Bank of America was doing commercial banking, corporate banking for some of the same companies. So my entrepreneurial journey to be real upfront was kind of more forced that, you know, in over those two years from 08 to 2010.

you know, my partner and I realized that it might be better for us to go because it's a little bit difficult for us to be the investment advisor on the one side of the company and the bank, that holds their money also have a relationship with them. So we left and we started a consulting business doing the same thing that we did at Merrill Lynch and investment firm and independent one. and that was my first taste of being an entrepreneur, but it wasn't by my choice. It was just more by,

circumstances related to things that had happened at levels well beyond you and I.

Rob Pene (19:10.146)
Yeah, wow, that's cool. Forced, yeah, that's good. Sometimes that pressure creates the opportunity. Good.

Henry Yoshida (19:14.668)
Yeah. Yeah. So, yeah, that was, that was the main thing. And then, you know, after that consulting business, you know, that was a small business that my partner and I ran, you know, that kind of gave me, I wouldn't say like a taste of it, but at least like some experience in it and a little bit more comfort knowing that, you didn't need to have some big corporate logo on your business card. Ironically enough, this is like sort of in that when I was getting out of that business and selling that business before doing the

startup route with the Honest Dollar and then Rocket Dollar after that. That was the time when people stopped kind of using business cards, know, because at that point in 2014, the iPhone had been out for now five years and people were starting to use more of the LinkedIn's and iPhone contacts and they were like physical business cards.

Rob Pene (19:53.955)
Yeah, yeah.

Rob Pene (20:03.544)
Yeah, yeah. So you seem pretty fit, man. And then just hearing your story, it sounds like there's a lot of discipline that you've had in your life where you, know, graduate school requires a lot of discipline to do well. And then, you know, during that, that tenure period, what would you attribute that discipline to from the work ethic and all that?

Henry Yoshida (20:15.384)
Yep.

Henry Yoshida (20:23.278)
You know, I don't even define it as work ethic. I think that I'm probably someone who's pragmatic enough to know about being consistently good just enough of the time to keep moving forward. I think that people that are too regimented and too strict actually, you know, they end up getting disappointed, right? Because they're trying to hold themselves up to a standard that no one's going to live up to. But, you know, I take friction.

out of the ways, maybe the way that I live my life. And I follow a lot of the methodologies of a very famous book. You know, I read his blog before the book came out, but James Clear's Atomic Habits. You know, and I don't know if you, you know, your community or if you've ever read that book. It's a really easy book. It only probably takes four to five hours to read. And it is a massive best seller. It probably has 300,000 reviews on Goodreads. So it's well read. And

Rob Pene (21:19.573)
wow.

Henry Yoshida (21:21.55)
You what he talks about is that, you know, putting yourself in a position, like, know, putting things in a position to make it easier for you to do these habits. So like he uses an example in the book of saying that, let's say that, you know, between now and the end of the year, you want to get in better shape. Um, and you want to, you know, start by maybe doing a run or going to the gym. He said, well, you know, most people, they dive right in and they say, you know, I'm going to go to the gym. I'm going to work out. what do they do? They hop in the car three days straight at five in the morning and show up and.

pussed out like a two hour workout and then they burn themselves out. It's hard. They're sore. but instead he said that maybe the better methodology is that for the next like week, just put your workout shoes and your workout shorts by the foot of your bed. And you may end up like stepping out of your bed and walking straight over those shoes, but you know, they're there. I you're the one to put them there the night before. and then maybe the week after that, like actually put the shoes on.

Rob Pene (22:08.6)
Yeah

Henry Yoshida (22:20.078)
You know, go to the gym, no workout plan in place, but maybe just go in there and like, you know, mess around in a couple of machines. Like now you're starting to develop a habit that, you know, you can go there, you know, you can spend the five to seven minutes to drive to your closest local gym. Uh, and so for you, you're making things easy. And he'll say the same things with like work that, um, you know, for you that if you want to make sure that you're productive and you start your day early, right? Like say to yourself that I always have my morning coffee, but have your morning coffee at your.

Rob Pene (22:24.996)
Hmm.

Henry Yoshida (22:50.274)
desk, which means you're already you'll already be at your desk at 8am. Like you may not actually do any work first time, but you're just doing little things. And then you said after a while, this habit develops in a way to where you're not just someone who goes to the gym. You're a fit person who's in shape. Like, you know, your identity changes as your habits change, right? Like, you know, if you're someone who smokes and you want to quit smoking, right? If you've really like, you know, done the stuff to get out of it, like now you're a nonsmoker. You're not someone who doesn't smoke.

Rob Pene (22:51.278)
Yeah.

Rob Pene (23:09.081)
Yes.

Henry Yoshida (23:19.362)
You're just, your identity is a non-smoker, a non-drinker, you know, and so forth. But going back to my side, it's that, maybe I am like probably overly structured compared to a lot of people I've talked to, but I like to think about it more that, you know, consistency is, is a lot better than motivation. And if you're pretty good, a lot of the time you actually make a lot of progress.

Rob Pene (23:21.527)
Yeah, that's good.

Rob Pene (23:44.258)
Yeah, and you won't need to be motivated because you're already moving. Yeah.

Henry Yoshida (23:48.078)
You'll probably never need to be perfect because reality is you'll never be perfect Yeah, I mean literally the definition of perfect is Sort of like an attainment level that you're not supposed to be able to get to so

Rob Pene (23:53.176)
Yeah, you're okay with that. Yeah.

Rob Pene (24:03.586)
Right, that's right. Yeah, so building quick win habits is good, yeah.

Henry Yoshida (24:08.225)
Yeah, or just doing things to remove the friction. There's lots of examples if you think about it, right? So, the late Steve Jobs, the genius behind Apple, co-founder of Apple, right? Well, everyone knew that all he wore were jeans and a black turtleneck. It's because he didn't want to any of his brain calories thinking about what to wear, right? He was the guy who knew that...

Rob Pene (24:24.621)
it.

Rob Pene (24:30.178)
Right.

Henry Yoshida (24:35.296)
All of our children would be like finger on iPad in every restaurant in America. And he knew that would happen in the 1990s and early 2000s. We see that today. He saw that a generation ago.

Rob Pene (24:43.715)
Mmm.

Rob Pene (24:51.992)
Yeah.

Henry Yoshida (24:52.27)
mean, that we would be a society that would probably end up being evolutionarily two inches shorter than we would have been because now we walk around looking down at our phone. So in 500 years or 1500 years, the average human might actually go down in height because of it.

Rob Pene (24:59.438)
Yeah

Rob Pene (25:08.674)
Because of the phone, that's crazy to think about.

Henry Yoshida (25:11.318)
I it's possible. Very possible.

Rob Pene (25:13.1)
It is, Yeah, because we're building. Yeah, your habits can shape your identity. That's good. Yeah.

Henry Yoshida (25:19.022)
Yeah, well your habits are your identity, right? You're a nonsmoker, you're a non-drinker, you're person who works out, you're a father, you know, and so forth.

Rob Pene (25:27.812)
Yeah. Yeah. Is there anything you're excited about in the future? know the retired.com thing is a fairly new kind of integration. Do you see yourself do something else? Or take it to next level?

Henry Yoshida (25:42.67)
I like running the Rocket Dollar. mean, I think there's real opportunity there and I really appreciate being a part of that retired.com family because it provides the resources that I don't think that we could have gotten on our own. That's been translating, but what excites me about the business side of Rocket Dollar is that right now someone buying real estate or someone buying a non-public investment in their IRA

is kind of a taboo thing. It's not normal. But I believe that in the near future, it will be very, very normal. Just like, you know, I'll give other examples. I'm a person who likes to give real examples of people we're going to identify with and that hopefully translate into, you know, he's right. Which is that 15 years ago, you know, we thought to ourselves that there was only the option for someone to go pick you up at the airport or for you to go just take a cab.

Rob Pene (26:15.628)
Yeah.

Henry Yoshida (26:41.976)
to get your hotel, right? But in the last 15 years, now the number one dominant thing, and I'll explain it without using the term, is that you basically take a ride with a stranger who will drop you off, right? I mean, you imagine like if you described this to someone, but someone, maybe Travis Kalanick, the founder of realized that this would be the case. And now when we take a vacation, we think to ourselves that do we want to stay?

Rob Pene (26:53.699)
He said.

Henry Yoshida (27:07.02)
in hotel or do we want to rent a room in someone's house or do we just want to rent someone's house? Now, think of this conversation in 2005. Hey, we're going to go to the beach with the kids. Are we going to like, should we like see if someone might want to just lend us their house or either even we just crash at their house with them and maybe they make us breakfast in the morning? You think no way that's going to happen. But that's like literally a conversation that happens now and a decision that's made with

Airbnb and Uber today that literally did not exist only 15 years ago. Neither one of those thoughts ever existed unless you wanted to get killed by a psycho. Which, so I don't think that it's too far-fetched for people to think that, they're going to tap into their retirement savings to buy something that is not just the top 500 publicly traded companies in the United States.

Rob Pene (27:45.398)
No. Right.

Rob Pene (28:04.771)
Right.

Henry Yoshida (28:05.026)
Like is that an unusual thing to say? It might be right now, depending on who you ask, they're going to say, well, you know, with your 401k, you always got to invest in, you know, mutual funds are safe. Everyone knows them. Be like, well, you know, and, but in the late nineties and early two thousands, most people thought it was crazy to buy your stocks on your own. And now, yeah, you know, 13 year olds do it on Robin Hood in a custodial account. You know, so at

Rob Pene (28:12.43)
Mm-hmm.

Rob Pene (28:24.024)
Yeah. Yeah.

Yeah. Yeah. Yeah.

Henry Yoshida (28:33.998)
There's a lot of things I think in the world that will That are there if you think about it that will change and that's what gets me excited that that you know I feel like I have a business or I have a product where You know when I started in 2018 when I was on that stage going through There were it was a tech conference So some people thought it was cool But even at that conference some people thought it was crazy And then if I were in a group of regular people if I just went into a grocery store and talked to people and they would have thought it's crazy They might think it's crazy now

Rob Pene (29:01.038)
They're scammed.

Henry Yoshida (29:03.362)
But it's exactly like, you know, the guy may be doing user research on a company that wasn't yet created called Uber say, what about the idea of like, you know, letting strangers pick you up? You know, that way Rob doesn't have to waste his time. He's got, you know, podcasts to record. He doesn't have time on a Friday afternoon to go get you at the airport. know, like you're your college buddy. You're going to hang out all weekend. Just catch a ride with a stranger to the house. I'm like, imagine that conversation in 2005.

Rob Pene (29:24.194)
Yeah. Yeah.

Rob Pene (29:30.636)
Yeah. So that's great because you're going to normalize the conversation of using your retirement to purchase alternative investments. The real estate and...

Henry Yoshida (29:33.048)
How nutty you sound.

Henry Yoshida (29:42.766)
Or it's just going to happen and we're the product that already facilitates that. mean, the reality is that prior to Uber and prior to Airbnb, there were actually companies that existed that did that, right? It's just, they're the ones that we know. And so forth. They just weren't mainstream. So someone has to be in a position to capture that mass market when it becomes normal. I think so. You know, that's the main thing, but, but I did look at all these times in the very recent past, right? Cause you and I are.

Rob Pene (29:55.405)
Mmm.

Henry Yoshida (30:11.694)
Not young but not old either that you know, I remember that you and I are both old enough to remember that We thought no one's gonna trust typing their credit card number into their computer to buy something online Now more things are bought online than there are then they're bought physically in a store and The largest store in the world only sells online in the form of Amazon and the size of Amazon is actually bigger

than the top five largest stores who actually sell stuff in person combined right now. And Amazon is only a 25 year old company.

Rob Pene (30:43.042)
Yeah, crazy.

Rob Pene (30:49.678)
Wow, I didn't realize that. Yeah, I didn't realize that it's that young. It's just fresh out

Henry Yoshida (30:50.54)
or 30 year old company.

Henry Yoshida (30:55.296)
Amazon IPO'd in the 90s.

Rob Pene (31:01.048)
I remember when it was just books. Yeah, crazy.

Henry Yoshida (31:06.124)
Right, right. was books. And then, you know, things change, like, and they change that way in less than a generation. So that kind of stuff excites me. And then, you know, for me, another thing I guess I get excited about is that as I get older, I'm constantly thinking about ways to biologically be younger. So it's kind of funny, like how your perspective changes, right?

Rob Pene (31:16.055)
Yeah.

Rob Pene (31:26.78)
Yeah, okay. Yeah.

Henry Yoshida (31:31.094)
I think I spent all of my childhood wanting to be grown up and then once you're grown up you do everything you can to like try to stay young. Right, exactly. I don't know if everyone's ever told you but there's this kind of funny memes that all the things that you hated as a kid that you you start doing as an adult like you hated bedtimes and now you're like man I really need to be in bed by 9 30.

Rob Pene (31:36.524)
Yeah, stay healthy, stay young. Yeah, you can...

Rob Pene (31:50.221)
yeah. Yeah. Yeah, you're I appreciate I appreciate you being on here because you're definitely a pioneer a trailblazer. You know, you're one of those dudes that's going to change literally. Yeah, the fabric of how things work in finance, especially with with retirement. So that's amazing.

Henry Yoshida (32:04.078)
you

Henry Yoshida (32:12.014)
I mean, it's going to change like, you know, with or without me. I'm just saying that people are going to invest beyond these, you know, funds because when people did that and started buying their own stocks and now people trade stocks like crazy. I don't participate in it, but I think another thing too, that's just kind of become like really, I don't know if it's like been good for society, but like the overlay of

of being able to make all sorts of random bets on a sporting event now and having them tie together across sports, across games and so forth. Is it making the game better? I don't know, but I don't know that anyone could have seen it this way also 20 years ago.

Rob Pene (32:43.17)
always.

Yeah.

Rob Pene (32:56.002)
No, huge.

Henry Yoshida (32:57.95)
It's huge, it's revitalizing interest in the games, it's bringing people in, and they're crossing the sports. So now someone who otherwise might not have had any interest in baseball is following simultaneously what's going to happen in the Formula One race in Austin this weekend, along with what will happen in the baseball playoffs, along with a college football game and a pro football game this weekend. And if the right thing happens in all four of those, then they're going to win big money.

Rob Pene (33:12.598)
Yeah, yeah.

Rob Pene (33:19.469)
Yeah.

Rob Pene (33:23.746)
Yeah, it gets them to think about money too in a different way. Yeah.

Henry Yoshida (33:27.34)
Yeah, and maybe not in the healthiest of ways, but I just use that as another example of how, you know, what the large, large majority of people thought would never happen is now actually not just happening, but it's very normal.

Rob Pene (33:42.276)
It's commonplace. Yeah. Yeah. So normalized.

Henry Yoshida (33:45.76)
entering your credit card number on the computer. I mean, you don't even enter it anymore. You just literally save it on your phone. Because we're too late.

Rob Pene (33:51.564)
Well now at Amazon, you just put your hand and then you can pay for stuff, yeah.

Henry Yoshida (33:55.734)
Yeah, you know, take rides, we take millions of rides a day in cars with strangers. You know, we stay in homes and rooms of people who we have no idea who owns the house.

Rob Pene (33:59.05)
It's... Yeah.

Rob Pene (34:12.632)
Yeah.

Henry Yoshida (34:12.896)
And then, know, one day people will buy real estate using their, you know, retirement monies and so forth, along with 19,000 other things that I'm not smart enough to think about what happened in the near future.

Rob Pene (34:17.901)
Mm-hmm.

Rob Pene (34:24.739)
Yeah.

This is good. This is good. Well, you're definitely a pioneer, Yeah, visionary pioneer that's kind of paving the way. So this is exciting. If you have one tip to give to somebody that's either, yeah, that's thinking about retirement and what to do with their money, how would you advise them to think about it differently?

Henry Yoshida (34:28.654)
Thank you.

Henry Yoshida (34:34.766)
you

Henry Yoshida (34:51.454)
So I talk to people all the time about retirement and people spend way too much time thinking about what to invest in. Like what's the right investment? and they don't spend enough time thinking about maybe just putting away some amount of money and just making sure it's in the right type of account. And I'll explain here that instead of trying to figure out like, you know, research and decide like what area of the stock market or what investments you need to be in.

Rob Pene (35:01.156)
Yeah.

Henry Yoshida (35:20.15)
Maybe the best thing is just to get started, you know, just save something. It doesn't even need to be an investment. could just be an high yield savings account. At least you put some money away. Number one. And then number two, if you were to do that instead of concentrating again on what specific type of investment or what you think is going to do the best short term, medium term and long term, make sure it's in the right account. So I always tell people that if your company, if you work for a company has a 401k, any dollar you put in there is going to actually perform better than.

regardless of what you invest in outside of it because Every dollar you put in means that you make one dollar less in income, which means you would pay less in taxes Which means a lot more to you in California than it does to me in Texas Which then the company may also offer a match So if they offer a 100 % match you made a hundred percent return on your dollar the second they gave you the money There's no investment that's going to give you a hundred percent return the second you put the money in so that's first and then if you end up

Rob Pene (35:58.885)
Yeah.

Rob Pene (36:13.518)
Yeah.

Henry Yoshida (36:16.418)
having enough money to put away and max out those accounts, go to an IRA next, because every dollar you put in there, you can deduct against your income. And depending on your tax bracket and where you live in the country, California, again, being worse than Texas, might save you another 20%, 25 % more in better returns. And then finally, after that, you put it into a taxable account. But people do the backwards, which is where they spend all the time thinking about what to invest in when they should probably think about just getting some money put away and making sure it's in the right spot.

Rob Pene (36:31.726)
Mmm.

Rob Pene (36:46.308)
That's good. That's really good.

Henry Yoshida (36:48.014)
So that's the tip I have. So the easy way to remember is asset location, not asset selection. Think of where it's held. It's actually probably more important than what you hold.

Rob Pene (36:57.572)
You

Rob Pene (37:01.634)
Right. Because then you're spending less time and just putting it down and then letting the money do its thing versus wasting time thinking through not putting the money anywhere.

Henry Yoshida (37:11.552)
Exactly. It goes back to like the person who wants to get in shape, right? They're going to get online and research all these like different diets slash like workout plans. And the reality is they should probably just get comfortable going to the gym. Do they even know where it is? You know, at this point, right? Just go there, test out a couple of machines, see what works for you. Right. Everyone's going to get in shape different ways because they like or hate certain things. Like, you know, someone else, someone might like getting out and walking.

Rob Pene (37:14.339)
Yes.

Yeah.

Rob Pene (37:30.435)
Yeah.

Henry Yoshida (37:38.54)
someone else would think that's boring and they just want to get out and play pickleball or basketball. Another person might say, you know, I actually really like just going in there, knocking out a 30 minute weight workout, full body, get in and out of there. You don't know, instead of planning all that stuff upfront, just get started.

Rob Pene (37:52.229)
Just do it. just planning is good, but doing is better.

Henry Yoshida (37:59.862)
Right. Yeah, yeah, that's right. And so like, you know, execution, like, know, you got to start. mean, you make course correct, but the thing is you haven't gotten too far in the journey. just started. So it'd be fine.

Rob Pene (38:12.132)
Right, right, right. Just move. Very good. Where can people follow you online? Your Instagram. Yeah, let's give them your Instagram.

Henry Yoshida (38:14.36)
Mm-hmm. Yep.

Henry Yoshida (38:21.198)
Oh, so the Instagram is under the handle fit finance Henry. So fit finance Henry, the rocket dollar side, you know, really easy. We were at rocket dollar.com. So we have a lot of information about our types of accounts and alternative investments and self-directed IRAs, which are the types of IRAs that allow you to do private investments there.

Rob Pene (38:35.907)
Mm-hmm.

Henry Yoshida (38:46.486)
You know, myself also and the company, have a pretty big presence on LinkedIn as well. people are on a more professional network side. It can be there, but yeah, those are the best ways to reach us. And on the RocketDar side, if they're actually interested in learning about the accounts themselves, there's a phone number that you can call too. So right on the website. Yeah. So we talked a lot about the future, future things, but you know, we are old school and that we have a phone number on the site.

Rob Pene (38:50.99)
Thanks.

Rob Pene (39:03.972)
nice! that's gonna be-

Rob Pene (39:12.184)
Yeah, and that's usually the best too. That's usually the best. pick up the phone and call. Yeah.

Henry Yoshida (39:17.934)
Yeah, yeah. And, know, those calls come in all the time and they're just general questions. and, uh, you know, again, these are new concepts to people. So it does, you know, it does help to have someone explain that these are, these are allowed private investments have always been held inside of IRAs. just not been as well known, just like, you know, someone's always, you know, crashed on someone's couch before. Now it's just now the normal average American family does it and not just some weirdo.

Rob Pene (39:22.041)
Wow.

Rob Pene (39:29.624)
Yes.

Rob Pene (39:46.38)
Yeah, yeah, well this is good. Man, I appreciate you.

Henry Yoshida (39:48.418)
You know, now people take Ubers all the time, but there were people that used to hitchhike back in the 1980s. Exactly right. Now it's normal. So it's just instead of our thumb, we use our phone.

Rob Pene (39:54.796)
Yeah, yeah, yeah, it was scary. But now they do it all day. Crazy.

Yeah

Yeah, well great. appreciate you, man. Thank you for the time. This has been helpful. has been and inspiring too. Yeah.

Henry Yoshida (40:09.326)
Yeah. thanks, Rob. I appreciate it. Yeah, great to have the conversation on a Friday afternoon.

Rob Pene (40:18.272)
Amen, amen. Appreciate you. Alrighty, thank you.

Henry Yoshida (40:22.328)
Thank you.