Cut The Tie Podcast with Henry Yoshida
Most executives spend decades earning, saving, and investing money without ever truly understanding where their capital sits or how much control they actually have over it.
In this episode of Cut The Tie, Thomas Helfrich sits down with Henry Yoshida, CEO and co-founder of Rocket Dollar, to unpack the mindset shift that separates passive investing from intentional ownership. Henry shares his journey from corporate finance at Merrill Lynch to building financial technology companies that help people unlock alternative investments inside retirement accounts.
This conversation explores why access often matters more than invention, how comfort can quietly limit opportunity, and why knowing where the money is can change how executives think about risk, freedom, and long-term success.
About Henry Yoshida
Henry Yoshida is the CEO and co-founder of Rocket Dollar, a financial technology company that enables individuals to invest retirement funds into private and alternative assets. With a career rooted in financial services and retirement planning, Henry has built multiple companies focused on giving people more control over capital they already own.
His work centers on access, education, and empowering individuals to make informed decisions outside traditional Wall Street structures.
In this episode, Thomas and Henry discuss:
- Henry’s transition from corporate finance to entrepreneurship
- Why understanding capital matters more than creating investments
- How retirement accounts quietly limit choice and control
- The role of discomfort in long-term success
- Alternative investments and personal knowledge as a risk filter
- Why diversification means more than stocks and bonds
- Cutting ties with institutional thinking around money
- Redefining success beyond titles, status, and safety
Key Takeaways
- Access beats invention
You don’t need to create investments to benefit from opportunity. - Capital already exists
The question is who controls it and how it’s used. - Comfort can limit growth
Security often delays necessary change. - Risk is contextual
What feels risky to institutions may feel obvious to individuals. - Ownership creates clarity
Control over money leads to better decisions.
Connect with Henry Yoshida
🌐 Website: https://www.rocketdollar.com/
🏢 Parent Company: https://www.retired.com
💼 LinkedIn: https://www.linkedin.com/in/henryyoshida/
Connect with Thomas Helfrich
🌐 Website: https://www.cutthetie.com
💼 LinkedIn: https://www.linkedin.com/in/thomashelfrich
📧 Email: t@instantlyrelevant.com
🚀 Instantly Relevant: https://www.instantlyrelevant.com
Serious about LinkedIn Lead Generation? Stop Guessing what to do on LinkedIn and ignite revenue from relevance with Instantly Relevant Lead System
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Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
SPEAKER_01 (00:00):
Welcome to the Cut the Tie Podcast.
Hello, I'm your host, ThomasAlfrick.
I'm on a mission to help you cutthe tie to whatever's holding
you back from your success.
Now, that success has to bedefined by you because you have
to own it.
Can't be somebody else's.
Otherwise, you're chasingsomeone else's dream.
And it's not going to be uh it'snot going to be very good when
you get there.
It's going to be lame.
Uh today I'm joined by HenryYoshida.
Uh Henry, how are you today?
SPEAKER_00 (00:20):
Hi, I'm doing great.
Thanks, Thomas.
SPEAKER_01 (00:22):
I appreciate you coming on.
Take a moment to introduceyourself and what it is you do.
SPEAKER_00 (00:27):
Sure.
My name is Henry Yoshida.
Uh my background, my entirecareer, I started corporate like
a lot of people on the show, wasat Merrill Lynch in financial
services.
Uh, I broke away, uh, kind ofdid a baby entrepreneur step in
2010.
I basically left Merrill Lynchto do the same business I was
doing there, but actually on myown, uh, sold that business.
And since then, I've built twofinancial product companies, all
(00:48):
focusing in my area ofexpertise, which are retirement
plans.
And I currently am the CEO andco-founder of a company called
Rocket Dollar, and we let peopleown private and alternative
investments inside of their IRA.
We've done it since 2018, andit's kind of funny because on
August 8th, there was anexecutive order signed to allow
private and alternativeinvestments to be held inside of
401k plans, which are kind ofthe triple down before you get
(01:09):
to an IRA.
So I like to tell people that Iwas six and a half years ahead
of the game in three presidents.
SPEAKER_01 (01:15):
That's I mean, that's a uh as somebody who has
a 401k that sits there and looksat me.
I we look at alternatives likeRobs and other things to go,
what can we do with this moneyexcept the mercy of the market,
right?
Uh so this I I'm excited to havethis conversation because we'll
we'll get a ton in maybe to whatyou're uh doing now.
I'll leave people, you know, youcan tease it just enough.
Uh the topic about uh there arethere are choices out there for
(01:36):
what you guys do.
I and so I like to ask thequestion of you know, what is
your unique uh why should peoplework with you on your products
and and your tech or yourofferings?
SPEAKER_00 (01:46):
Sure.
Well, um so uh most of thecompanies that are in our space,
and it sounds like you're alittle bit familiar, they were
started by people that actuallyare usually the creators and
sellers of these alternativeinvestments.
So I like to tell people thatyou know it wasn't really their
primary thing.
I mean, my background since theyear 2000 was I accidentally
fell into the niche of taxadvantage retirement plans
401k's IRA.
(02:07):
So I come from that backgroundside, not the alternative
investment and private fundissuance side.
And this Rockefeller is actuallymy second tech company.
My last one was sold to GoldmanSachs.
So, you know, I think that ourdifferentiator is that we are a
brand, we're online, we have thebest tech, and we come from a we
come from the perspective of welove these accounts and the
(02:28):
platform, and it's up to theindividual to decide what they
want to invest in.
Like in other words, we didn'tcreate the platform because we
already have a real estateinvestment or syndication to
sell to people, and that's notreally the purest way to start
the business.
SPEAKER_01 (02:40):
I mean it sounds like you uh because you have so
much experience in this place,and like like you said, you you
didn't back into it becausesomething wasn't working or you
weren't selling enough mortgagesor something, like where a lot
of these individuals or theysold their business and they
need some side money until their401k becomes mature enough to
use it uh ironically, uh you'reyou're from it.
So you're solving a knownproblem that you knew was in the
(03:01):
industry and you're beingpointed about what it is you're
gonna go do for somebody.
So it's not like a saying of theold, like this is a problem,
this solved it.
SPEAKER_00 (03:09):
Exactly.
And I mean we specifically saywe don't even bring the deals.
I mean, you know, although I'mtrained as an investment expert,
I mean, all the customersactually are the ones that find
their own investments.
My job is just to facilitate,and and I kind of fell into this
business that I created sixyears ago, um, where basically
people pay me to get access tomoney that they already have.
unknown (03:29):
Right.
SPEAKER_01 (03:30):
We'll dive into that because that that blew me away.
My discovery of Robs and somethings you could do is we were
looking at real estate orfranchise or whatever else, and
I was like, sure.
I can take my money out now andmake it a share and pay myself,
and if I lose it, I don't oweanything back.
SPEAKER_00 (03:47):
That's correct.
SPEAKER_01 (03:48):
There's a way to pay yourself and just pay income tax
on it right now.
Um uh uh so the uh ADHDers outthere who can't just listen have
to be looking at something.
Where should they give them theone link?
We give them two, it's gonna beover.
Give them one link, they shouldgo stalk you a bit while we're
talking.
SPEAKER_00 (04:03):
Well, uh the good thing is uh I'm also a big
proponent uh of easy domain.
So the company uh isrocketdollar.com, so just
rocketdollar.com, and you canfind everything else about us
there.
And then uh my parent company,so I'm a part of a parent
company, is retired.com, soR-E-T-I-R-E-B and
RocketDollar.com.
(04:24):
So we're one and the same.
And we have a sister company wewere talking about offline uh
that specializes in justcryptocurrencies and digital
assets inside of IRA.
So we're the two brands and weboth roll up to retired.com.
SPEAKER_01 (04:36):
That's easy that's super easy.
Uh and those were very cheapdomains, I'm sure, Rock.
SPEAKER_00 (04:40):
Um yeah, yeah, I'd cheap.
And then the irony of having uhyour work email address be Henry
at retired.com when that's yourwork email address uh makes for
great conversations at onairplanes.
I've noticed.
You're right.
SPEAKER_01 (04:51):
Like, well, do you work or not?
I'm like, kinda.
SPEAKER_00 (04:54):
Kinda, yeah.
Um it how do you define success?
You know, for me, um I neverdefined it by money.
Um I've talked about this beforeon plenty of shows, but you
know, I didn't grow up withmoney.
Uh my parents immigrated here tothe United States uh right
before I was born.
So I was the first person bornin my family in the United
States, and they never theydidn't come here to go to
(05:16):
college.
So, you know, you see a lot ofAsian Americans and they, you
know, their parents or theirgrandparents now came here to
get education and then they endup getting a great job at a
great corporation at the righttime in the heydays of America.
But my parents came here andended up in the restaurant
industry, so that's actually theother side of a lot of I think
immigrant uh immigrants who cometo the United States, they end
up falling for the restaurantand hospitality industry.
(05:39):
So I didn't really grow up withmuch.
So to me, the definition ofsuccess uh for most of my life
was actually ironically enough,being able to have a job where I
could wear a tie and go into anoffice as opposed to like, you
know, going into a place andwalking to the back where the
kitchen is or where the stockroom is.
SPEAKER_01 (05:56):
There life is irony, though.
I'll tell you, I uh I've neverworn a tie so much as started my
own podcast about cutting it.
Well, it's a half a tie, so it'suh the other is my my main
company is named instantlyrelevant.
The stuff that we do and put insystem growth systems for
companies, it's not instant.
(06:16):
A lot of investment mindset andtime, but not anything brand
problems.
Lots and right.
Right.
Um so with that definition ofsuccess, uh you've you've you've
talked about your journey alittle bit, but maybe identify
in your journey where where uhyou've had to cut that
metaphoric tie to achieve thatsuccess.
SPEAKER_00 (06:36):
You know, that upbringing, I probably didn't go
into it enough, was you know,kind of what shaped my mindset,
which is that most people whenthey get to that sort of uh you
know corporate cushy job afterdoing the normal things, right?
Studying hard in high school,getting a good score on the
SATs, uh getting a chance to goto college, and then using
college as a way to get yourselfinto uh some sort of career
(06:56):
track or company track and soforth.
But you know, the way I came up,uh, I guess when I got to that
corporate level, I I was okaynot being comfortable.
In other words, there was nosafety net for me growing up.
So it didn't really matter forme to take chances or to see
flaws or to identifyopportunities inside.
And I think while a lot of mycolleagues, and we all started
(07:17):
in a training class, we were allthere.
I was a uh I was at Big MerrillLynch Bank of America for 10
years.
Uh, I started in 2000, I left in2010.
I tell people that, you know, Isurvived two recessions, the
company only made it through oneof them at that time at Merrill
Lynch.
But, you know, I went into thatorganization with an open eye to
maybe thinking about things thatI could do outside of the
(07:40):
organization on my own that theydidn't care about because they
were just too big.
It wasn't worth their time ormoney.
And I didn't get so mired intothe you know, relying on the
bonuses and getting getting toocomfortable.
And next thing you know, you're50 years old and and you know,
you've been at this place for 20years to kind of doing the same
old, same old.
You hate it.
And at this point, you're justtrying to make it to the finish
life.
SPEAKER_01 (08:00):
Your your life is now wrapped around what you've
built with it.
SPEAKER_00 (08:04):
I mean, it's yeah, it it's it's being okay being
uncomfortable, like being okaytaking chances because you know
there was no safety net for yougrowing up.
So, like, you know, going backto where you started, if you
started pretty low, it's notthat bad.
You've already been there andyou know how to come out of it.
SPEAKER_01 (08:20):
Well, and so so how would you describe the tie
though?
Is it was it the you did itseems like you've had a really
good mindset with it.
Was it was there difficultymaybe with family or anything
else to be like, hey, you'reyou're gonna get rid of that
corporate job and do what?
Like, you know, did you have todeal with because that this a
lot of people have to deal withsometimes the hardest things to
go make a move toentrepreneurship or something
else is the expectations ofothers on you.
(08:44):
Did you have that challenge?
SPEAKER_00 (08:45):
I did.
It didn't prop it didn't come somuch from my parents.
Uh they just had sort of a maybea lack of overall understanding
of how things worked in inAmerica or corporate America,
just based on the backgroundsthey told you about them.
So they weren't, they were neverreally the people I leaned on.
They were they were myinspirations in terms of just
being hard workers and peoplewho just always sacrificed you
know themselves for for theability for my brother and I to
(09:08):
go to college, get greateducations, get great job
tracks, and so forth.
But it was actually kind of hardon the home front in my just
sort of nuclear family at thattime.
You know, my spouse was like,hey, it's comfortable if you
leave and you go do thesethings, what if it doesn't work?
And um, you know, I was kind ofdo the mindset, although it
worked out much, much better forhim of the Jeff Bezos.
Was I used to think about itthat, well, you know, what if
(09:29):
I'm sitting here at 50, 60, 70,and in his case he used 70 and
80 years old um uh to leave andstart Amazon, was to say that,
you know, I'm gonna look backand say that I just never tried
at that point.
SPEAKER_01 (09:41):
That's right.
I know uh I quote the DaveMatthews songs from Lie in our
Graves.
You know, why would we lie inour Graves?
Wondering what we could havebeen, right?
Like you uh and it's by the way,when you when as I have a spouse
that also, you know, I was askedto leave the original name of
this podcast, which isn't onthat YouTube channel, so it's
never been promoted.
Yeah, I I could have called itasked to leave, to be fair, but
(10:03):
um you know, at some point youjust become unhireable in that
scenario, and and it you youcannot give your spouse in that
moment a good answer.
Exactly.
There's just no answer andthere's no reassuring that it's
gonna work out fine becauseyou're like I'm because there's
a financial commitment to getstarted.
SPEAKER_00 (10:19):
So not only are you leaving something that's very
steady, you're you're probablyalso per proposing, right?
Like uh uh coming up with thescenario and a proposal
standpoint to say, honey, notonly am I thinking about leaving
and doing this, it's gonna costme money to get it started.
So we're actually gonna gonegative.
Uh right.
So this bit of money is gonnaturn off, and then we're gonna
tap into savings so I can go netmore negative.
(10:41):
Uh um, and then the nextquestion naturally, is it gonna
work?
I have no idea.
No idea.
Yeah, I don't know.
In other words, maybe I shouldwork on my presentation skills,
but uh, you know, I'm sure maybesome listener can comment with
something better uh from that.
SPEAKER_01 (10:56):
The thing I try to draw from that, right, is that
uh even as successful as you'vebeen, you've had that moment.
Every entrepreneur is gonna havethat moment of you don't know
it's gonna work.
You just believe in yourselfthat you can make something
work.
And this is the starting point.
You know, it's like you'reyou're a giant vector heading
somewhere different, and you'relike, I'm gonna figure it out
because I can't because Iunderstand this area well
enough.
But even you who's had greatsuccess, listen, people, you
(11:19):
like he didn't know either.
And probably on your second,third venture, you're like,
you're more confident, maybehave more fun, maybe like, I'm
not 100% sure the marketresponds to this.
SPEAKER_00 (11:26):
There's a lot of stuff.
Maybe maybe the second one mightbe even harder because then
there's an expectation that youwon't actually fail, but you
have the same uncertainty.
I mean, that always exists inbusiness.
So I would say it's a little bitadded pressure.
I mean, I I liken this to likeuh, you know, we're sitting here
now, I'm getting kind ofexcited, it's preseason
football, but I think about it,there's a way to come into the
NFL as Tom Brady, you know, likea very low draft pick who
(11:48):
exceeded everyone'sexpectations.
And then there's a way to comein like Peyton Manning, you
know, the the son of a uh NFLHall of Famer, number one high
school player in the country,number one college player in the
country, number one pick in thedraft.
They both ended up being great,but I I just have this guess
that it was harder to becomegreat if you're Peyton Manning.
And Tom Brady, no one's lookingat you.
(12:09):
No one looked, no one looked athim for five years.
SPEAKER_01 (12:11):
Yeah, it's unbelievable what he did.
Yeah, it's uh it's a greatanalogy.
Uh if you could uh though goback in your timeline at any
point, when would you go back?
What would you do differently?
SPEAKER_00 (12:24):
I think um when I left, uh uh when I left to do my
services business, so that waswhen I left um the financial
consulting in the retirementplan space uh to create a
registered investment advisoryfirm.
Uh, I think that if I could goback in my timeline to do that,
I might have actually done thatum uh with a little more
(12:46):
analysis in terms of picking,let's say, a business partner.
So, you know, I got into apartnership with someone, but it
was the person I worked withthere.
And I think that we haddifferent um, you know,
different plans for the future,but we never talked about that.
We were talking too much aboutthe present.
Um, and he was an individual whogrew up, you know, with money.
He was gonna, you know, inheritlike a pretty decent sized
(13:06):
empire.
Um, and and a decent sizedempire was much more than what I
was gonna, what I was gonna get.
I was actually staring more inthe in the eyes of having to
potentially pay for healthcarefor my parents while doing this
because they worked in therestaurant industry and you
don't really have greatinsurance plans in that
industry.
So I think if I had it to dodifferently to be more succinct
about it, I might have picked mypartners a little bit
(13:27):
differently.
Like it, and and not that hewasn't uh the right person.
It's just that just reallyunderstanding that is the
mindset correct for theimmediately pre-move,
immediately launching thebusiness, intermediate term, and
maybe even long term, just youknow, just see if there's
alignment for that long termfirst.
SPEAKER_01 (13:45):
Yeah, I mean, well, someone's you know hearing a
hundred million dollars, let'ssay, like their interest in what
they're doing, even if it'sdoing something great, like a
couple million years, is gonnago to zero.
They're like, I put that to anannuity and I'm gonna make two
and a half times that, and I'llbe on a yacht.
I mean, like, my god, I don'tcare about this anymore.
And you're like, well, I dobecause that's a lot of money
and that's I need that.
And if you do that, you screwme.
(14:06):
So those are uh beautifulquestions that to go back to.
Like, you're not a line.
Now, it could have been anequity investor.
You might be like, hey, he'sgonna have money, let's get him
in here so when we need more, weget who you gotta ask.
SPEAKER_00 (14:17):
Right.
Yeah, exactly.
But this was just a purebusiness partner and it was
different.
So when the business startedworking, yeah, you know, the
other person wanted to scaleback, take it easy, whereas I
wanted to kind of lean into itand try to grow it more, and
that ultimately led us into aposition uh of just uh an
impasse where we had to decideto liquidate that business and
sell it essentially.
SPEAKER_01 (14:36):
That's too bad.
I mean, but it it it it it'sfair to say at the moment you
looked at it, it was happeningto you as opposed to for you,
but it looks like it happenedfor you.
SPEAKER_00 (14:45):
Right.
That's right.
And then, you know, even thesecond business, same thing, you
know, probably made you know abad decision in terms of who to
partner with, but with RocketDollar, it's a little bit
different.
You know, I made sure at thatpoint that I was sort of the uh
the primary person who foundedthe business.
I have co-founders, but I wasthe primary person who started
the business from my equity.
SPEAKER_01 (15:06):
But I wanted to get to this point of kind of the
show where uh you definitelysolidified expertise that people
don't know you, but tell me whywhen I hear the words
alternative investment, how didthat happen where I feel
uncomfortable talking to youabout it as a financial person?
Do you want to talk about thatfeel of like, oh, this guy's
trying to scam me?
SPEAKER_00 (15:25):
Well, uh, and you know, the the term itself
alternative and and wrappedaround and used as an adjective
to describe an investment'sactually changed quite a bit
just even in the last 25 years.
I mean, when I started atMerrill, an alternative
investment might have beenactually, it was tangentially a
mutual fund that might haveinvested in companies that were
not registered in U.S.
stock exchanges.
So that was considered kind ofalternative back then.
(15:46):
And now alternative might be, Idon't know, some sort of you
know, crypto token or justsomething that's not publicly
registered in the stock markets.
But it's just changed.
And I think for me, you know,I've always just thought that if
everyone is invested in thesame, let's say, 500 companies,
because that's what the advicehas been for decades, then maybe
(16:07):
there's an opportunity.
Now, personally, I actually doquite a bit of pretty boring
investments because myprofessional life is tied
towards these private andalternative investments.
So I've been very public aboutthat, and I've been quoting a
lot of news articles andfinancial media uh about my own
personal investment strategies.
But, you know, it's anopportunity that that people
wanted to diversify outside of,let's say, the S P seven, I call
(16:30):
it, because really, you, youknow, 85% of the returns have
been kind of driven by the topseven companies in the SP 500.
So it's it's really the S Pseven right now and so forth.
So it was really looking at itas a business opportunity and
embracing the idea that thereare people that maybe want to go
beyond these stocks and bonds.
And um the way that I kind ofgot into it was I thought I'm
(16:51):
actually not smart enough tocreate the investments, but I'm
pretty damn good at knowingwhere the money is that might
potentially go into theseinvestments, and they're held by
90 million Americans in IRAs and401k accounts.
SPEAKER_01 (17:03):
That's uh it's like because it's gonna be like it
was like this marketing of youshould put stuff in 401k, be
safe with that money and this.
But there was never an option ofwhere do you take the risk,
right?
Where do I actually take risk?
Is it myself?
Do I buy a franchise, which isyou know, whatever it is, right?
And and those are all time-basedthings and those are hard to do.
Uh give me uh if you're allowedto do this, I'm not sure for the
(17:25):
record of you, but what are someinteresting alternative
investments that people don'trealize they can do?
SPEAKER_00 (17:31):
So I think people realize they can do alternative
investments.
Remember, the key is that theydon't realize they can do it in
an account where they can deferthe taxes for 20, 30 years.
But um, so let me answer thistwo ways.
Maybe the weirdest investmentsthat people have.
Um, you know, we have peoplethat actually own
income-producing assets, but notwhat you'd typically think.
So think like, you know, uh longlife, long sustainability,
(17:54):
durable, you know, constructionequipment.
People own those inside theirIRAs with us.
Uh, we have people who actuallyown cattle and racehorses.
These are income-producingassets um inside of an IRA.
Um, but you know, maybe moretraditionally, you know, think
about the single-family realestate property on the other
side of town.
Like you know that new airportsare gonna be built, you know
(18:15):
that the highway's expanding upto this area.
So, you know, Thomas, you keepexplaining that maybe this is
where did people think abouttaking the risk?
Well, if you're someone and youlive in Austin, Texas, or
Atlanta, Georgia, and you happento know that a new airport or a
new highway interchange is gonnapop out on the other side of
town, then if you live in thatlocality and you have capital in
the form of your IRA or 401k,it's not risky to you.
(18:38):
You have that sort of personalknowledge, you have that private
knowledge.
It's risky if we live in Austinand I'm thinking about doing
some real estate transaction inAtlanta.
I have no idea about thatmarket.
But um, you know, what I'vetended to find is that the
customers I talk to, they feelactually very empowered.
They feel like they have alittle bit of control over what
they're investing in versus thisvery intangible mega giant
corporation or mega giantfinancial services firm has
(18:59):
created a mega giant mutual fundto invest in mega giant
corporations of which they neveractually even talked to.
Yeah.
SPEAKER_01 (19:06):
There's a thing I came up with with when we were
looking at buying a franchisecalled Rob's RBS.
And I'm you'll explain itbetter, but effectively, you
could start a company and fundit with your 401k and it creates
shares, C Corp, whatever else,uh, which allows you to have
operating capital, which thenoperates like a company.
Yeah, which you could buy lotsof things with it.
And I'm like, and you could payyourself a salary to manage it,
(19:29):
even, you know, and there'srules and stuff like that.
But I I it blew my mind, thatwas my first opening to this,
that well, I can have a whole401k and I could go buy an
investment property with it, soI avoid all the cost of carrying
and stuff and flip it and go tryto make 10 or 20 percent and
just pay my tax or pay myselfsalary, offset the cost.
And there's a whole bunch ofways you can actually collect
money from those thingsdifferently.
(19:50):
Um and and and I I'm to me, it'slike if I was you saw you were
coming on the show, I was like,that's like the one of a billion
things probably I could do.
Um So you know, they can pickyour platform or others.
One thing I've struggled withthough, with with that, and why
we've kind of pulled back, mywife and I was I'm going from
let's say a JP Morgan Chase,known, insured, even though it's
(20:11):
you know it's that they'reknown.
Yeah.
Less likely to have a made-offsituation with that one right
now.
But I'm going to some pl otherplatform or some guy that I
don't know who might own it.
How do I get my head aroundwho's got my money and where?
SPEAKER_00 (20:24):
Well, so in in our case, uh, if you do look at one
of the providers in the space,there's a lot that are just the
front-facing side.
So they have the platform andthey open the accounts for you,
but um, they have to outsourcethe custody of these assets.
So in our case, we actually, thethird company in our in our
branded house at retired.com isactually our own integrated
trust company.
So we actually custody theassets.
We have a state chartered trust.
(20:46):
Um, and by law, those trustcompanies actually have to keep
those funds segregated from anyof our business investments.
So, you know, and in most cases,we actually hold more of the
paper title to the investmentsthat are customers owned.
So we have upwards of 10,000 to12,000 different investments
within that custody.
But the money has actually goneto the issuer or whoever created
(21:06):
that particular investmentopportunity.
So that's where the risk is fromthe actual money, because the
money, actual money, is going tosomeone who's pulling it
together to purchase a realestate development project,
right?
Not actually held by us.
We're holding the paper title tothat investment, but you've
physically wired your money fromyour IRA account to some
individual for a real estatedevelopment project.
(21:27):
So that's where the risk is.
SPEAKER_01 (21:29):
How do you manage that then?
Because that's that, you know,like for someone who may have a
half million dollars in theiraccount and that that's it.
Like, you know, that and maybetheir home, right?
That's a very common middleclass, upper middle class
scenario.
You got a half million, you gotmaybe 200,000 in equity, and
they're like, well, I got tomake that work with Social
Security.
How do they get the head gettheir head around that risk?
SPEAKER_00 (21:50):
Well, you know, I think one of the things, so this
is my side of being a um acareer financial services
person, but uh but none of ourcustomers actually do a large
proportion of their overallinvestable assets with us.
So, you know, I think that wesort of end up managing about 10
to 25 percent of the investableassets of the customer base.
So at any one point, you know,they they're not putting all of
(22:12):
their investable monies at risk.
So we actually kind of advocatethat they don't do that with us.
So uh I know that doesn't answeryour question about completely
eliminating the wit risk, butit's no different.
You wouldn't put all of yourretirement savings into one
stock, just like you wouldn'tput all of your retirement
savings into one privateinvestment deal either.
(22:32):
If you're gonna leave anything,we may do 15%, but not you know,
100% of it.
And we typically at RocketBallar, we represent holding
roughly about 10 to 25% ofsomeone's overall retirement
assets, which doesn't eveninclude anything else they might
have in taxable brokerageaccounts, you know, equity,
other assets, and so forth.
SPEAKER_01 (22:51):
I mean, that's a good way to mitigate the uh I
will tell you one of my favoriteanswers when I ask people like,
hey, would you go back?
What would you do?
The best answer is crypto.
Next question.
We just liquidate everything andput in there and just got to
make it up the make up here in2025, it'd be fine.
SPEAKER_00 (23:09):
Exactly.
I don't know.
I might even look at itdifferently.
I mean, you know, you know,NVIDIA at five dollars, Amazon
at one dollar.
Any one of those.
Apple and when I say Amazon atone dollar, I mean this was this
was the case in you know 2003.
SPEAKER_01 (23:22):
How many split since?
Oh, you probably know actuallythe answer to that.
Um but Henry, thank you by theway, so much for coming on
today.
Uh uh just tell somebody abouttheir, you know, who should get
a hold of you, how do you wantthem to do it?
SPEAKER_00 (23:34):
So if they come to the website at rocketdollar.com,
it's not designed to actuallysell anyone anything.
It's actually designed as aneducational site.
So we have tons and tons ofarticles.
So I think one of the thingsthat's been our key to success
is that our articles and ourinformation and knowledge base
is actually what gets indexedonline.
So as we go from a Google searchworld to maybe a chat GPT search
(23:57):
world, I noticed that ChatGPTactually pulls up a lot of
information.
It links back to articlesembedded within our website or
blog posts that we've written orinformation pages that we've
written to teach people aboutRob's transactions,
self-directed IRAs, investing inprivate alternative investments
using tax-advantaged accounts.
And um, you know, I think if yougo there directly, you can spend
(24:18):
a lot of time just learningstuff.
And it's up to you to decide ifyou actually want to do business
with us or with any of ourcompetitors.
Uh again, like I said, I thinkour edge is that, you know, for
me, uh it's founder DNA in thecompany.
I come from a traditionalfinancial services background,
deep knowledge and expertise andbackground in the retirement
space, a retirement accountspace, not the investment space.
(24:40):
I don't I don't sell anyinvestments.
Um, and then couple that withgreat technology and and we
allow you to sort of create andmanage the account online.
SPEAKER_01 (24:49):
Now, before I let you go here, there was a
question I should have askedtoday, and I didn't.
Yeah.
What was that question?
And how do you answer it?
SPEAKER_00 (24:59):
Let's see.
Uh I saw all the questions thatyou were gonna ask me, right?
So things like, let's say thequotes, and I was thinking that
did I give a quote that no one'sever given before?
Maybe, you know, who knows?
Maybe Thomas has a bunch ofAsian American people.
I'm Japanese by by nature, butum, but this is also if if you
were to ask me how do I live mylife, it actually ties into the
quote that I have, which is thatI've gotten to the point we're
(25:21):
both almost 50 years old now.
I'm 48 years old, and I've justthought about that I don't have
time to waste um on things thatdon't matter to me anymore.
So I always go back to the theBruce Lee continuous learning,
continuous adaptation, alwayslike improving yourself, but you
know, just absorbing anythingthat's useful, uh discarding
anything that's not useful, andjust add what's uniquely yours.
(25:41):
And that's usually a combinationfor success.
And it's just really a mindsetuh if you ask me, like, how do
you live your life now versushow you might have lived it 15
years ago?
Well, 15 years ago, I cared alot about what other people
thought and what I showed otherpeople.
Present me today, I care a lotless, and I feel like I have 10
times more time and control.
SPEAKER_01 (26:01):
I'm with you, man.
I'm actually I'd rather justmove into a condo, no mortgage,
and and then be like, hey, do weeven need all this stuff?
I'd like to go through like whatdo we really need?
Anyway, just like it's the valuebucket, right?
You're if happiness is a bucketand unhappiness is the holes,
and it if you just fill holes,you don't need a lot of drip to
keep it away from uhevaporating, right?
(26:22):
You've got to keep but justenough above evaporation level
to fill it and it'll stay.
SPEAKER_00 (26:25):
Exactly.
Yeah, you you start to learnwhat what makes you happy and
what you value, and uh you knowbasically your your your habits
are basically what would kind ofcreate who you are.
Um and they would yeah, and thetwo most precious things are
probably at this point in lifeand just in general are health
and time.
(26:45):
And if you're healthy, you'llhave more time.
SPEAKER_01 (26:48):
I think uh actually I'll leave we'll leave on that
note, but that actually I thinkis the most important thing the
entire time.
Your health and your time,because that determines what you
get to go do and when and whatyou dream about.
Yeah, and they're tied to eachother.
The man with uh uh with hishealth has a million dreams, the
man without has but one.
Exactly.
I like that, and that's a greatway.
Thank you.
Thank you, Henry, for coming ontoday.
I appreciate it.
(27:08):
Thank you, Thomas.
And listen, everyone who made itthis far uh in the show, thank
you for listening.
If this was the first time here,I do hope it's the first of
many.
And if you've been here before,you heard me say this get out
there, go cut a tie towhatever's holding you back, own
your success, get after it.
Welcome to the Cut the Tie Podcast.
Hello, I'm your host, ThomasAlfrick.
I'm on a mission to help you cutthe tie to whatever's holding
you back from your success.
Now, that success has to bedefined by you because you have
to own it.
Can't be somebody else's.
Otherwise, you're chasingsomeone else's dream.
And it's not going to be uh it'snot going to be very good when
you get there.
It's going to be lame.
Uh today I'm joined by HenryYoshida.
Uh Henry, how are you today?
SPEAKER_00 (00:20):
Hi, I'm doing great.
Thanks, Thomas.
SPEAKER_01 (00:22):
I appreciate you coming on.
Take a moment to introduceyourself and what it is you do.
SPEAKER_00 (00:27):
Sure.
My name is Henry Yoshida.
Uh my background, my entirecareer, I started corporate like
a lot of people on the show, wasat Merrill Lynch in financial
services.
Uh, I broke away, uh, kind ofdid a baby entrepreneur step in
2010.
I basically left Merrill Lynchto do the same business I was
doing there, but actually on myown, uh, sold that business.
And since then, I've built twofinancial product companies, all
(00:48):
focusing in my area ofexpertise, which are retirement
plans.
And I currently am the CEO andco-founder of a company called
Rocket Dollar, and we let peopleown private and alternative
investments inside of their IRA.
We've done it since 2018, andit's kind of funny because on
August 8th, there was anexecutive order signed to allow
private and alternativeinvestments to be held inside of
401k plans, which are kind ofthe triple down before you get
(01:09):
to an IRA.
So I like to tell people that Iwas six and a half years ahead
of the game in three presidents.
SPEAKER_01 (01:15):
That's I mean, that's a uh as somebody who has
a 401k that sits there and looksat me.
I we look at alternatives likeRobs and other things to go,
what can we do with this moneyexcept the mercy of the market,
right?
Uh so this I I'm excited to havethis conversation because we'll
we'll get a ton in maybe to whatyou're uh doing now.
I'll leave people, you know, youcan tease it just enough.
Uh the topic about uh there arethere are choices out there for
(01:36):
what you guys do.
I and so I like to ask thequestion of you know, what is
your unique uh why should peoplework with you on your products
and and your tech or yourofferings?
SPEAKER_00 (01:46):
Sure.
Well, um so uh most of thecompanies that are in our space,
and it sounds like you're alittle bit familiar, they were
started by people that actuallyare usually the creators and
sellers of these alternativeinvestments.
So I like to tell people thatyou know it wasn't really their
primary thing.
I mean, my background since theyear 2000 was I accidentally
fell into the niche of taxadvantage retirement plans
401k's IRA.
(02:07):
So I come from that backgroundside, not the alternative
investment and private fundissuance side.
And this Rockefeller is actuallymy second tech company.
My last one was sold to GoldmanSachs.
So, you know, I think that ourdifferentiator is that we are a
brand, we're online, we have thebest tech, and we come from a we
come from the perspective of welove these accounts and the
(02:28):
platform, and it's up to theindividual to decide what they
want to invest in.
Like in other words, we didn'tcreate the platform because we
already have a real estateinvestment or syndication to
sell to people, and that's notreally the purest way to start
the business.
SPEAKER_01 (02:40):
I mean it sounds like you uh because you have so
much experience in this place,and like like you said, you you
didn't back into it becausesomething wasn't working or you
weren't selling enough mortgagesor something, like where a lot
of these individuals or theysold their business and they
need some side money until their401k becomes mature enough to
use it uh ironically, uh you'reyou're from it.
So you're solving a knownproblem that you knew was in the
(03:01):
industry and you're beingpointed about what it is you're
gonna go do for somebody.
So it's not like a saying of theold, like this is a problem,
this solved it.
SPEAKER_00 (03:09):
Exactly.
And I mean we specifically saywe don't even bring the deals.
I mean, you know, although I'mtrained as an investment expert,
I mean, all the customersactually are the ones that find
their own investments.
My job is just to facilitate,and and I kind of fell into this
business that I created sixyears ago, um, where basically
people pay me to get access tomoney that they already have.
unknown (03:29):
Right.
SPEAKER_01 (03:30):
We'll dive into that because that that blew me away.
My discovery of Robs and somethings you could do is we were
looking at real estate orfranchise or whatever else, and
I was like, sure.
I can take my money out now andmake it a share and pay myself,
and if I lose it, I don't oweanything back.
SPEAKER_00 (03:47):
That's correct.
SPEAKER_01 (03:48):
There's a way to pay yourself and just pay income tax
on it right now.
Um uh uh so the uh ADHDers outthere who can't just listen have
to be looking at something.
Where should they give them theone link?
We give them two, it's gonna beover.
Give them one link, they shouldgo stalk you a bit while we're
talking.
SPEAKER_00 (04:03):
Well, uh the good thing is uh I'm also a big
proponent uh of easy domain.
So the company uh isrocketdollar.com, so just
rocketdollar.com, and you canfind everything else about us
there.
And then uh my parent company,so I'm a part of a parent
company, is retired.com, soR-E-T-I-R-E-B and
RocketDollar.com.
(04:24):
So we're one and the same.
And we have a sister company wewere talking about offline uh
that specializes in justcryptocurrencies and digital
assets inside of IRA.
So we're the two brands and weboth roll up to retired.com.
SPEAKER_01 (04:36):
That's easy that's super easy.
Uh and those were very cheapdomains, I'm sure, Rock.
SPEAKER_00 (04:40):
Um yeah, yeah, I'd cheap.
And then the irony of having uhyour work email address be Henry
at retired.com when that's yourwork email address uh makes for
great conversations at onairplanes.
I've noticed.
You're right.
SPEAKER_01 (04:51):
Like, well, do you work or not?
I'm like, kinda.
SPEAKER_00 (04:54):
Kinda, yeah.
Um it how do you define success?
You know, for me, um I neverdefined it by money.
Um I've talked about this beforeon plenty of shows, but you
know, I didn't grow up withmoney.
Uh my parents immigrated here tothe United States uh right
before I was born.
So I was the first person bornin my family in the United
States, and they never theydidn't come here to go to
(05:16):
college.
So, you know, you see a lot ofAsian Americans and they, you
know, their parents or theirgrandparents now came here to
get education and then they endup getting a great job at a
great corporation at the righttime in the heydays of America.
But my parents came here andended up in the restaurant
industry, so that's actually theother side of a lot of I think
immigrant uh immigrants who cometo the United States, they end
up falling for the restaurantand hospitality industry.
(05:39):
So I didn't really grow up withmuch.
So to me, the definition ofsuccess uh for most of my life
was actually ironically enough,being able to have a job where I
could wear a tie and go into anoffice as opposed to like, you
know, going into a place andwalking to the back where the
kitchen is or where the stockroom is.
SPEAKER_01 (05:56):
There life is irony, though.
I'll tell you, I uh I've neverworn a tie so much as started my
own podcast about cutting it.
Well, it's a half a tie, so it'suh the other is my my main
company is named instantlyrelevant.
The stuff that we do and put insystem growth systems for
companies, it's not instant.
(06:16):
A lot of investment mindset andtime, but not anything brand
problems.
Lots and right.
Right.
Um so with that definition ofsuccess, uh you've you've you've
talked about your journey alittle bit, but maybe identify
in your journey where where uhyou've had to cut that
metaphoric tie to achieve thatsuccess.
SPEAKER_00 (06:36):
You know, that upbringing, I probably didn't go
into it enough, was you know,kind of what shaped my mindset,
which is that most people whenthey get to that sort of uh you
know corporate cushy job afterdoing the normal things, right?
Studying hard in high school,getting a good score on the
SATs, uh getting a chance to goto college, and then using
college as a way to get yourselfinto uh some sort of career
(06:56):
track or company track and soforth.
But you know, the way I came up,uh, I guess when I got to that
corporate level, I I was okaynot being comfortable.
In other words, there was nosafety net for me growing up.
So it didn't really matter forme to take chances or to see
flaws or to identifyopportunities inside.
And I think while a lot of mycolleagues, and we all started
(07:17):
in a training class, we were allthere.
I was a uh I was at Big MerrillLynch Bank of America for 10
years.
Uh, I started in 2000, I left in2010.
I tell people that, you know, Isurvived two recessions, the
company only made it through oneof them at that time at Merrill
Lynch.
But, you know, I went into thatorganization with an open eye to
maybe thinking about things thatI could do outside of the
(07:40):
organization on my own that theydidn't care about because they
were just too big.
It wasn't worth their time ormoney.
And I didn't get so mired intothe you know, relying on the
bonuses and getting getting toocomfortable.
And next thing you know, you're50 years old and and you know,
you've been at this place for 20years to kind of doing the same
old, same old.
You hate it.
And at this point, you're justtrying to make it to the finish
life.
SPEAKER_01 (08:00):
Your your life is now wrapped around what you've
built with it.
SPEAKER_00 (08:04):
I mean, it's yeah, it it's it's being okay being
uncomfortable, like being okaytaking chances because you know
there was no safety net for yougrowing up.
So, like, you know, going backto where you started, if you
started pretty low, it's notthat bad.
You've already been there andyou know how to come out of it.
SPEAKER_01 (08:20):
Well, and so so how would you describe the tie
though?
Is it was it the you did itseems like you've had a really
good mindset with it.
Was it was there difficultymaybe with family or anything
else to be like, hey, you'reyou're gonna get rid of that
corporate job and do what?
Like, you know, did you have todeal with because that this a
lot of people have to deal withsometimes the hardest things to
go make a move toentrepreneurship or something
else is the expectations ofothers on you.
(08:44):
Did you have that challenge?
SPEAKER_00 (08:45):
I did.
It didn't prop it didn't come somuch from my parents.
Uh they just had sort of a maybea lack of overall understanding
of how things worked in inAmerica or corporate America,
just based on the backgroundsthey told you about them.
So they weren't, they were neverreally the people I leaned on.
They were they were myinspirations in terms of just
being hard workers and peoplewho just always sacrificed you
know themselves for for theability for my brother and I to
(09:08):
go to college, get greateducations, get great job
tracks, and so forth.
But it was actually kind of hardon the home front in my just
sort of nuclear family at thattime.
You know, my spouse was like,hey, it's comfortable if you
leave and you go do thesethings, what if it doesn't work?
And um, you know, I was kind ofdo the mindset, although it
worked out much, much better forhim of the Jeff Bezos.
Was I used to think about itthat, well, you know, what if
(09:29):
I'm sitting here at 50, 60, 70,and in his case he used 70 and
80 years old um uh to leave andstart Amazon, was to say that,
you know, I'm gonna look backand say that I just never tried
at that point.
SPEAKER_01 (09:41):
That's right.
I know uh I quote the DaveMatthews songs from Lie in our
Graves.
You know, why would we lie inour Graves?
Wondering what we could havebeen, right?
Like you uh and it's by the way,when you when as I have a spouse
that also, you know, I was askedto leave the original name of
this podcast, which isn't onthat YouTube channel, so it's
never been promoted.
Yeah, I I could have called itasked to leave, to be fair, but
(10:03):
um you know, at some point youjust become unhireable in that
scenario, and and it you youcannot give your spouse in that
moment a good answer.
Exactly.
There's just no answer andthere's no reassuring that it's
gonna work out fine becauseyou're like I'm because there's
a financial commitment to getstarted.
SPEAKER_00 (10:19):
So not only are you leaving something that's very
steady, you're you're probablyalso per proposing, right?
Like uh uh coming up with thescenario and a proposal
standpoint to say, honey, notonly am I thinking about leaving
and doing this, it's gonna costme money to get it started.
So we're actually gonna gonegative.
Uh right.
So this bit of money is gonnaturn off, and then we're gonna
tap into savings so I can go netmore negative.
(10:41):
Uh um, and then the nextquestion naturally, is it gonna
work?
I have no idea.
No idea.
Yeah, I don't know.
In other words, maybe I shouldwork on my presentation skills,
but uh, you know, I'm sure maybesome listener can comment with
something better uh from that.
SPEAKER_01 (10:56):
The thing I try to draw from that, right, is that
uh even as successful as you'vebeen, you've had that moment.
Every entrepreneur is gonna havethat moment of you don't know
it's gonna work.
You just believe in yourselfthat you can make something
work.
And this is the starting point.
You know, it's like you'reyou're a giant vector heading
somewhere different, and you'relike, I'm gonna figure it out
because I can't because Iunderstand this area well
enough.
But even you who's had greatsuccess, listen, people, you
(11:19):
like he didn't know either.
And probably on your second,third venture, you're like,
you're more confident, maybehave more fun, maybe like, I'm
not 100% sure the marketresponds to this.
SPEAKER_00 (11:26):
There's a lot of stuff.
Maybe maybe the second one mightbe even harder because then
there's an expectation that youwon't actually fail, but you
have the same uncertainty.
I mean, that always exists inbusiness.
So I would say it's a little bitadded pressure.
I mean, I I liken this to likeuh, you know, we're sitting here
now, I'm getting kind ofexcited, it's preseason
football, but I think about it,there's a way to come into the
NFL as Tom Brady, you know, likea very low draft pick who
(11:48):
exceeded everyone'sexpectations.
And then there's a way to comein like Peyton Manning, you
know, the the son of a uh NFLHall of Famer, number one high
school player in the country,number one college player in the
country, number one pick in thedraft.
They both ended up being great,but I I just have this guess
that it was harder to becomegreat if you're Peyton Manning.
And Tom Brady, no one's lookingat you.
(12:09):
No one looked, no one looked athim for five years.
SPEAKER_01 (12:11):
Yeah, it's unbelievable what he did.
Yeah, it's uh it's a greatanalogy.
Uh if you could uh though goback in your timeline at any
point, when would you go back?
What would you do differently?
SPEAKER_00 (12:24):
I think um when I left, uh uh when I left to do my
services business, so that waswhen I left um the financial
consulting in the retirementplan space uh to create a
registered investment advisoryfirm.
Uh, I think that if I could goback in my timeline to do that,
I might have actually done thatum uh with a little more
(12:46):
analysis in terms of picking,let's say, a business partner.
So, you know, I got into apartnership with someone, but it
was the person I worked withthere.
And I think that we haddifferent um, you know,
different plans for the future,but we never talked about that.
We were talking too much aboutthe present.
Um, and he was an individual whogrew up, you know, with money.
He was gonna, you know, inheritlike a pretty decent sized
(13:06):
empire.
Um, and and a decent sizedempire was much more than what I
was gonna, what I was gonna get.
I was actually staring more inthe in the eyes of having to
potentially pay for healthcarefor my parents while doing this
because they worked in therestaurant industry and you
don't really have greatinsurance plans in that
industry.
So I think if I had it to dodifferently to be more succinct
about it, I might have picked mypartners a little bit
(13:27):
differently.
Like it, and and not that hewasn't uh the right person.
It's just that just reallyunderstanding that is the
mindset correct for theimmediately pre-move,
immediately launching thebusiness, intermediate term, and
maybe even long term, just youknow, just see if there's
alignment for that long termfirst.
SPEAKER_01 (13:45):
Yeah, I mean, well, someone's you know hearing a
hundred million dollars, let'ssay, like their interest in what
they're doing, even if it'sdoing something great, like a
couple million years, is gonnago to zero.
They're like, I put that to anannuity and I'm gonna make two
and a half times that, and I'llbe on a yacht.
I mean, like, my god, I don'tcare about this anymore.
And you're like, well, I dobecause that's a lot of money
and that's I need that.
And if you do that, you screwme.
(14:06):
So those are uh beautifulquestions that to go back to.
Like, you're not a line.
Now, it could have been anequity investor.
You might be like, hey, he'sgonna have money, let's get him
in here so when we need more, weget who you gotta ask.
SPEAKER_00 (14:17):
Right.
Yeah, exactly.
But this was just a purebusiness partner and it was
different.
So when the business startedworking, yeah, you know, the
other person wanted to scaleback, take it easy, whereas I
wanted to kind of lean into itand try to grow it more, and
that ultimately led us into aposition uh of just uh an
impasse where we had to decideto liquidate that business and
sell it essentially.
SPEAKER_01 (14:36):
That's too bad.
I mean, but it it it it it'sfair to say at the moment you
looked at it, it was happeningto you as opposed to for you,
but it looks like it happenedfor you.
SPEAKER_00 (14:45):
Right.
That's right.
And then, you know, even thesecond business, same thing, you
know, probably made you know abad decision in terms of who to
partner with, but with RocketDollar, it's a little bit
different.
You know, I made sure at thatpoint that I was sort of the uh
the primary person who foundedthe business.
I have co-founders, but I wasthe primary person who started
the business from my equity.
SPEAKER_01 (15:06):
But I wanted to get to this point of kind of the
show where uh you definitelysolidified expertise that people
don't know you, but tell me whywhen I hear the words
alternative investment, how didthat happen where I feel
uncomfortable talking to youabout it as a financial person?
Do you want to talk about thatfeel of like, oh, this guy's
trying to scam me?
SPEAKER_00 (15:25):
Well, uh, and you know, the the term itself
alternative and and wrappedaround and used as an adjective
to describe an investment'sactually changed quite a bit
just even in the last 25 years.
I mean, when I started atMerrill, an alternative
investment might have beenactually, it was tangentially a
mutual fund that might haveinvested in companies that were
not registered in U.S.
stock exchanges.
So that was considered kind ofalternative back then.
(15:46):
And now alternative might be, Idon't know, some sort of you
know, crypto token or justsomething that's not publicly
registered in the stock markets.
But it's just changed.
And I think for me, you know,I've always just thought that if
everyone is invested in thesame, let's say, 500 companies,
because that's what the advicehas been for decades, then maybe
(16:07):
there's an opportunity.
Now, personally, I actually doquite a bit of pretty boring
investments because myprofessional life is tied
towards these private andalternative investments.
So I've been very public aboutthat, and I've been quoting a
lot of news articles andfinancial media uh about my own
personal investment strategies.
But, you know, it's anopportunity that that people
wanted to diversify outside of,let's say, the S P seven, I call
(16:30):
it, because really, you, youknow, 85% of the returns have
been kind of driven by the topseven companies in the SP 500.
So it's it's really the S Pseven right now and so forth.
So it was really looking at itas a business opportunity and
embracing the idea that thereare people that maybe want to go
beyond these stocks and bonds.
And um the way that I kind ofgot into it was I thought I'm
(16:51):
actually not smart enough tocreate the investments, but I'm
pretty damn good at knowingwhere the money is that might
potentially go into theseinvestments, and they're held by
90 million Americans in IRAs and401k accounts.
SPEAKER_01 (17:03):
That's uh it's like because it's gonna be like it
was like this marketing of youshould put stuff in 401k, be
safe with that money and this.
But there was never an option ofwhere do you take the risk,
right?
Where do I actually take risk?
Is it myself?
Do I buy a franchise, which isyou know, whatever it is, right?
And and those are all time-basedthings and those are hard to do.
Uh give me uh if you're allowedto do this, I'm not sure for the
(17:25):
record of you, but what are someinteresting alternative
investments that people don'trealize they can do?
SPEAKER_00 (17:31):
So I think people realize they can do alternative
investments.
Remember, the key is that theydon't realize they can do it in
an account where they can deferthe taxes for 20, 30 years.
But um, so let me answer thistwo ways.
Maybe the weirdest investmentsthat people have.
Um, you know, we have peoplethat actually own
income-producing assets, but notwhat you'd typically think.
So think like, you know, uh longlife, long sustainability,
(17:54):
durable, you know, constructionequipment.
People own those inside theirIRAs with us.
Uh, we have people who actuallyown cattle and racehorses.
These are income-producingassets um inside of an IRA.
Um, but you know, maybe moretraditionally, you know, think
about the single-family realestate property on the other
side of town.
Like you know that new airportsare gonna be built, you know
(18:15):
that the highway's expanding upto this area.
So, you know, Thomas, you keepexplaining that maybe this is
where did people think abouttaking the risk?
Well, if you're someone and youlive in Austin, Texas, or
Atlanta, Georgia, and you happento know that a new airport or a
new highway interchange is gonnapop out on the other side of
town, then if you live in thatlocality and you have capital in
the form of your IRA or 401k,it's not risky to you.
(18:38):
You have that sort of personalknowledge, you have that private
knowledge.
It's risky if we live in Austinand I'm thinking about doing
some real estate transaction inAtlanta.
I have no idea about thatmarket.
But um, you know, what I'vetended to find is that the
customers I talk to, they feelactually very empowered.
They feel like they have alittle bit of control over what
they're investing in versus thisvery intangible mega giant
corporation or mega giantfinancial services firm has
(18:59):
created a mega giant mutual fundto invest in mega giant
corporations of which they neveractually even talked to.
Yeah.
SPEAKER_01 (19:06):
There's a thing I came up with with when we were
looking at buying a franchisecalled Rob's RBS.
And I'm you'll explain itbetter, but effectively, you
could start a company and fundit with your 401k and it creates
shares, C Corp, whatever else,uh, which allows you to have
operating capital, which thenoperates like a company.
Yeah, which you could buy lotsof things with it.
And I'm like, and you could payyourself a salary to manage it,
(19:29):
even, you know, and there'srules and stuff like that.
But I I it blew my mind, thatwas my first opening to this,
that well, I can have a whole401k and I could go buy an
investment property with it, soI avoid all the cost of carrying
and stuff and flip it and go tryto make 10 or 20 percent and
just pay my tax or pay myselfsalary, offset the cost.
And there's a whole bunch ofways you can actually collect
money from those thingsdifferently.
(19:50):
Um and and and I I'm to me, it'slike if I was you saw you were
coming on the show, I was like,that's like the one of a billion
things probably I could do.
Um So you know, they can pickyour platform or others.
One thing I've struggled withthough, with with that, and why
we've kind of pulled back, mywife and I was I'm going from
let's say a JP Morgan Chase,known, insured, even though it's
(20:11):
you know it's that they'reknown.
Yeah.
Less likely to have a made-offsituation with that one right
now.
But I'm going to some pl otherplatform or some guy that I
don't know who might own it.
How do I get my head aroundwho's got my money and where?
SPEAKER_00 (20:24):
Well, so in in our case, uh, if you do look at one
of the providers in the space,there's a lot that are just the
front-facing side.
So they have the platform andthey open the accounts for you,
but um, they have to outsourcethe custody of these assets.
So in our case, we actually, thethird company in our in our
branded house at retired.com isactually our own integrated
trust company.
So we actually custody theassets.
We have a state chartered trust.
(20:46):
Um, and by law, those trustcompanies actually have to keep
those funds segregated from anyof our business investments.
So, you know, and in most cases,we actually hold more of the
paper title to the investmentsthat are customers owned.
So we have upwards of 10,000 to12,000 different investments
within that custody.
But the money has actually goneto the issuer or whoever created
(21:06):
that particular investmentopportunity.
So that's where the risk is fromthe actual money, because the
money, actual money, is going tosomeone who's pulling it
together to purchase a realestate development project,
right?
Not actually held by us.
We're holding the paper title tothat investment, but you've
physically wired your money fromyour IRA account to some
individual for a real estatedevelopment project.
(21:27):
So that's where the risk is.
SPEAKER_01 (21:29):
How do you manage that then?
Because that's that, you know,like for someone who may have a
half million dollars in theiraccount and that that's it.
Like, you know, that and maybetheir home, right?
That's a very common middleclass, upper middle class
scenario.
You got a half million, you gotmaybe 200,000 in equity, and
they're like, well, I got tomake that work with Social
Security.
How do they get the head gettheir head around that risk?
SPEAKER_00 (21:50):
Well, you know, I think one of the things, so this
is my side of being a um acareer financial services
person, but uh but none of ourcustomers actually do a large
proportion of their overallinvestable assets with us.
So, you know, I think that wesort of end up managing about 10
to 25 percent of the investableassets of the customer base.
So at any one point, you know,they they're not putting all of
(22:12):
their investable monies at risk.
So we actually kind of advocatethat they don't do that with us.
So uh I know that doesn't answeryour question about completely
eliminating the wit risk, butit's no different.
You wouldn't put all of yourretirement savings into one
stock, just like you wouldn'tput all of your retirement
savings into one privateinvestment deal either.
(22:32):
If you're gonna leave anything,we may do 15%, but not you know,
100% of it.
And we typically at RocketBallar, we represent holding
roughly about 10 to 25% ofsomeone's overall retirement
assets, which doesn't eveninclude anything else they might
have in taxable brokerageaccounts, you know, equity,
other assets, and so forth.
SPEAKER_01 (22:51):
I mean, that's a good way to mitigate the uh I
will tell you one of my favoriteanswers when I ask people like,
hey, would you go back?
What would you do?
The best answer is crypto.
Next question.
We just liquidate everything andput in there and just got to
make it up the make up here in2025, it'd be fine.
SPEAKER_00 (23:09):
Exactly.
I don't know.
I might even look at itdifferently.
I mean, you know, you know,NVIDIA at five dollars, Amazon
at one dollar.
Any one of those.
Apple and when I say Amazon atone dollar, I mean this was this
was the case in you know 2003.
SPEAKER_01 (23:22):
How many split since?
Oh, you probably know actuallythe answer to that.
Um but Henry, thank you by theway, so much for coming on
today.
Uh uh just tell somebody abouttheir, you know, who should get
a hold of you, how do you wantthem to do it?
SPEAKER_00 (23:34):
So if they come to the website at rocketdollar.com,
it's not designed to actuallysell anyone anything.
It's actually designed as aneducational site.
So we have tons and tons ofarticles.
So I think one of the thingsthat's been our key to success
is that our articles and ourinformation and knowledge base
is actually what gets indexedonline.
So as we go from a Google searchworld to maybe a chat GPT search
(23:57):
world, I noticed that ChatGPTactually pulls up a lot of
information.
It links back to articlesembedded within our website or
blog posts that we've written orinformation pages that we've
written to teach people aboutRob's transactions,
self-directed IRAs, investing inprivate alternative investments
using tax-advantaged accounts.
And um, you know, I think if yougo there directly, you can spend
(24:18):
a lot of time just learningstuff.
And it's up to you to decide ifyou actually want to do business
with us or with any of ourcompetitors.
Uh again, like I said, I thinkour edge is that, you know, for
me, uh it's founder DNA in thecompany.
I come from a traditionalfinancial services background,
deep knowledge and expertise andbackground in the retirement
space, a retirement accountspace, not the investment space.
(24:40):
I don't I don't sell anyinvestments.
Um, and then couple that withgreat technology and and we
allow you to sort of create andmanage the account online.
SPEAKER_01 (24:49):
Now, before I let you go here, there was a
question I should have askedtoday, and I didn't.
Yeah.
What was that question?
And how do you answer it?
SPEAKER_00 (24:59):
Let's see.
Uh I saw all the questions thatyou were gonna ask me, right?
So things like, let's say thequotes, and I was thinking that
did I give a quote that no one'sever given before?
Maybe, you know, who knows?
Maybe Thomas has a bunch ofAsian American people.
I'm Japanese by by nature, butum, but this is also if if you
were to ask me how do I live mylife, it actually ties into the
quote that I have, which is thatI've gotten to the point we're
(25:21):
both almost 50 years old now.
I'm 48 years old, and I've justthought about that I don't have
time to waste um on things thatdon't matter to me anymore.
So I always go back to the theBruce Lee continuous learning,
continuous adaptation, alwayslike improving yourself, but you
know, just absorbing anythingthat's useful, uh discarding
anything that's not useful, andjust add what's uniquely yours.
(25:41):
And that's usually a combinationfor success.
And it's just really a mindsetuh if you ask me, like, how do
you live your life now versushow you might have lived it 15
years ago?
Well, 15 years ago, I cared alot about what other people
thought and what I showed otherpeople.
Present me today, I care a lotless, and I feel like I have 10
times more time and control.
SPEAKER_01 (26:01):
I'm with you, man.
I'm actually I'd rather justmove into a condo, no mortgage,
and and then be like, hey, do weeven need all this stuff?
I'd like to go through like whatdo we really need?
Anyway, just like it's the valuebucket, right?
You're if happiness is a bucketand unhappiness is the holes,
and it if you just fill holes,you don't need a lot of drip to
keep it away from uhevaporating, right?
(26:22):
You've got to keep but justenough above evaporation level
to fill it and it'll stay.
SPEAKER_00 (26:25):
Exactly.
Yeah, you you start to learnwhat what makes you happy and
what you value, and uh you knowbasically your your your habits
are basically what would kind ofcreate who you are.
Um and they would yeah, and thetwo most precious things are
probably at this point in lifeand just in general are health
and time.
(26:45):
And if you're healthy, you'llhave more time.
SPEAKER_01 (26:48):
I think uh actually I'll leave we'll leave on that
note, but that actually I thinkis the most important thing the
entire time.
Your health and your time,because that determines what you
get to go do and when and whatyou dream about.
Yeah, and they're tied to eachother.
The man with uh uh with hishealth has a million dreams, the
man without has but one.
Exactly.
I like that, and that's a greatway.
Thank you.
Thank you, Henry, for coming ontoday.
I appreciate it.
(27:08):
Thank you, Thomas.
And listen, everyone who made itthis far uh in the show, thank
you for listening.
If this was the first time here,I do hope it's the first of
many.
And if you've been here before,you heard me say this get out
there, go cut a tie towhatever's holding you back, own
your success, get after it.
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