This Goldman Sachs Secret Finds Winning Investments ($3B+)
20m 44s
A growing number of Americans rely on social media for financial advice, much of which is inaccurate, leading to poor investment decisions. To counter this, a proven framework called the Investment X-Ray is introduced, offering a structured way to evaluate any investment. This framework consists of four key components: capital preservation (ensuring your investment doesn't lose value), tax efficiency (leveraging tax benefits such as 401(k)s or 1031 exchanges), yield or cashflow (whether the investment generates passive income), and growth (its long-term appreciation potential). Each component is scored on a 25-point scale, allowing for a total 100-point evaluation. This method enables investors to objectively compare options, avoid emotional reactions, and make data-driven decisions—especially when considering high-risk or unfamiliar ventures like startups or crypto. The speaker illustrates its use with examples such as gold, S&P 500 ETFs, Bitcoin, and real estate, showing how each investment scores differently across the four dimensions. The framework is not just theoretical; it is used daily by the speaker and his partners to assess opportunities, manage risk, and optimize returns. Ultimately, the Investment X-Ray empowers individuals to reject poor advice, avoid impulsive decisions, and build more rational, long-term financial strategies—even without being a financial expert. It serves as a vital tool for anyone navigating complex or uncertain markets.
Did you know that 43% of Americans actually get their financial advice from social media?
And the crazy part is that 80% of that advice is actually wrong.
I struggled with this myself because I was getting my advice from the internet, and I've
had a chance to build $2 billion companies.
I was a banker at Goldman Sachs, at Credit Suisse, and now I'm partners with Alex and
Leila Hermosi, and we run Acquisition.com.
And in my entire job, what I do is I'm a professional investor.
And with seeing all this tough advice out there, it breaks my heart because no one has
been taught a framework for how to actually invest in anything.
And so when I was a banker at Goldman Sachs, I didn't know how to do this either.
But one of my clients actually told me how he makes decisions on how he invests.
This was not even a Goldman Sachs framework.
This was from my client who was a billionaire.
And I thought about, wow, how can I take this and codify it?
To help myself and help my life.
And I've been using this framework for the last 20 years, and I'd love to teach you this
framework today.
And this is called the Investment X-Ray.
Now, this Investment X-Ray is the exact framework that I've taught to several entrepreneurs.
I've taught to my partners, Alex and Leila Hermosi.
I've taught to the companies that we invest in, and I use this in my life and in my business
every day.
So it has four parts, and I want to break down these parts for you because once you
hear this, you will never be able to unsee this, and it will help you make significantly
better decisions in your life.
So here's a four-part framework.
It's called the Investment X-Ray.
The first part is capital preservation.
What is the entire job?
Getting stuck in traffic.
What is the entire job of making an investment?
Well, the rule number one of making an investment is don't lose money, right?
Or if you know at least what you're doing, at least you know the risk that's associated
with it.
Capital preservation is ensuring that the amount of capital that you deploy, $100, $100,000,
$1 million, is protected in some way.
Now, I'm not suggesting that.
Every single investment that you make needs to be 100% protected.
Otherwise, if that was the only thing that you did, you would never take any risk.
And if you never take any risk, you would never get any growth.
Meaning, if you took your $100,000 and you put it in a mattress, or you put it in a savings
account and you got 0.01%, well, you're going to keep your $100,000.
That's what most people do.
But understanding what the potential for loss is, is important.
And you may be okay with a 5% potential loss if it gave you a significant.
For example, if I told you, hey, if you made this investment for $100, there's a chance
that you lose $5, but there's a chance that you make $200.
Would you take that investment?
Well, you may.
And that's why this is important.
So step number one of this framework is capital preservation.
Understanding what amount of your capital is at stake and what is the risk associated
with that.
All right.
Step number two is tax efficiency.
What is tax efficiency?
Tax efficiency.
The idea that when you make an investment, is there a way that you get some tax advantages
associated with it?
Most people just think about the ROI on an investment.
They're like, man, if I made this investment, what return am I going to get?
Well, that return may be extremely tax inefficient.
So you may get a great return, but then you're going to be really irritated that you're paying
all these taxes and then that just messes you up.
Is there a way to have some tax efficiency associated with it?
Now, let me give you an example.
Let's say you're investing in your 401k.
Well, you now have some tax efficiency associated with it, meaning there's two tax efficiency
methods when it comes to your retirement account or your 401k.
And that may be what you want.
The first is the amount of money that you put in your 401k is instantly tax deductible
from your adjusted gross income.
So you get a tax benefit of that money that you're actually investing in today.
Second is inside of your 401k plan, it grows tax free while it's there.
So whatever happens in that plan, if you buy and sell and reinvest,
it grows tax free, which if it was outside the plan, you would actually have to pay taxes
on, right?
So there is a tax efficiency component there.
There's something called a, in real estate, a 1031 like kind exchange.
Or what does that mean?
If you've not heard of it, the United States tax code allows you an incentive to not pull
your money out of the investments and to make sure that you don't pull your money out of
the investments, they give you an incentive to keep your money in because let's say you
invested in a building.
And you, uh, for, for a million dollars and that million dollars grew to 1.3 million.
Now, if you sold that building, you would pay capital gains taxes on the $300,000 of gain.
Well, the US government does not want you to take your money out.
They want you to reinvest all of it.
So they have this incentive mechanism called the 1031 exchange, which is if you roll all your
proceeds in to a new investment, then they defer that $300,000 gain into the future for you.
Now what you get.
There's two benefits there.
Benefit number one, you defer taxes into the future and the tax world.
Deference is the same as avoidance temporarily.
But second is you now get the entire $300,000 worth of gain that you could roll into a new
property, which otherwise you would not have been able to do.
You would have to pay taxes on that.
And then, um, it would have reduced the amount of principle that you could have put towards
your property.
So it's a massive gain there.
So there's a tax efficiency component for that investment.
Number one, capital preservation.
Number two, tax efficiency.
Well, what is number three?
The three is what I call yield or cashflow.
Is there a way in which that when you make an investment, the investment pays you, uh,
the very definition of an asset that I like to use is, is it something that pays you to
own it?
Meaning if you invest in this thing, do you actually get some kind of cashflow from it?
Because at the end of the day, there's two forms of income.
There's active income where you trade time for money and there's passive income, which
is it, which is hard to say passive.
But now you're going to get some kind of cashflow from it.
You're getting money for money where you're making an investment and your money is working
for you and generating some income for you.
Right.
I want to know if I'm that at that time in my life where I want some cashflow associated
with it.
I'll give you an example for my children.
I don't really need any cashflow like there for, for my daughter who's 10 years old.
She doesn't need any cashflow.
I, I'm, I'm paying for, for her Barbie.
I'm paying for iPad.
I am paying for her to go to school.
I'm, she doesn't need any cashflow, but maybe when she's, uh, you know, 60 years old, maybe
she wants some cashflow.
I don't know.
But you also now have the ability to understand, um, do you need the cashflow at this time?
So it's good to analyze investment using this.
So number three, cashflow.
Number four is growth and growth is only one part of the component of this.
So you say, if I'm making this investment, will this investment grow?
And I'll give you an example.
If you put, if you put your investment into a, uh, treasury bond, well, you get, maybe
get a 10 year treasury is now at 4.42%.
You get a 4.42%, uh, yield every single year, which is great, but your treasury bonds value
does not grow.
You just get the same a hundred thousand dollars.
You put it, you get it back and you just get the, the, the yield from it.
So the growth there is zero, right?
Zero.
Now that may be okay with you, but at least you know how to think about it and manage
the growth.
So those are the four components, capital preservation, tax efficiency, yield, which
is cashflow and growth.
The way I think about it very easily.
In a day-to-day operating perspectives, I think is I give each of those buckets, a simple
25 point score.
All when you add all the four of them up, you have a hundred point score.
So when I'm quickly evaluating an investment, I can run it through a filter and give it
a score and then get the total number associated with this is especially valuable when you're
trying to compare an investment.
So if you're comparing investment in investment B, you can at least know very quickly whether
the score makes sense.
So for example, let's say, let's, let's take a, let's take a.
Random example.
Let's say you're investing, thinking about investing in gold.
Well, what is the capital preservation associated with gold?
It's pretty good.
Like over the years, the historically it's shown us that gold may move up and down in
value, but it's backed by physical gold in some way.
So your capital preservation is decent.
So I'll probably give it a 20 out of a 25, right?
Uh, because when you pull it out, it may be a little different.
The second is tax efficiency.
Well, gold has no tax efficiency.
Maybe if you have some esoteric structures that you build with it, it may have some, but
just because you invest in gold, you don't get any tax efficiency associated with it.
So, uh, it gives me a zero for that 25.
The third is cashflow or yield.
Well, unless you do something creative from a structure perspective, you're not getting
a dividend yield interest on owning gold.
So that's another zero and then growth.
Well, growth is interesting from a gold perspective because gold is generally, uh,
inversely related to the performance of the general economic environment.
So gold is what they consider a flight to safety when the rest of the world is not
doing well, gold does better.
So sure.
Maybe I get some growth associated with it, but the growth is probably, I don't know if
I give it a score out of 25, I maybe give it a five.
So in this I've only given, I've got five points for growth and I've got 20 points for
capital preservation on a scale of a hundred.
I got a 25 out of a hundred for gold.
I'm not suggesting that as a be all end all of the answer, but at least it allows you to
quickly evaluate.
This investment, imagine your friend, um, wants you to invest in a startup.
By the way, I, this is the, as you get more and more successful, you're going to get the
peer pressure of your friends wanting to have you invest in their companies.
The, my recommendation to you is I try as hard as possible to invest my friends' businesses.
If, and only if I understand it.
All right.
Um, otherwise I'll tell you what I do in a second.
If you have a friend who's building a, a company.
that is in, I don't know, a startup and it's a startup in biotech and you know nothing about it.
It's a startup. So what is the capital preservation associated with that? I mean, not much.
I'm going to say zero. What is the tax efficiency associated with that? Not much. Zero. What is the
yield or cash flow associated with that? Not much. Zero. What is the growth associated with that?
A lot. Maybe. So I'm going to give it a full 25. Assume your friend is a rock star. Give it a full
25. So on that scale, I've got a zero, zero, zero, and 25. That's 25 out of 100. I got 25 points.
So it allows me to at least say, huh, it gives me a chance to evaluate whether this investment is
the right investment, whether investment, I have some framework for doing it. Now,
here's the one thing that I will recommend. If you have a friend that is making a startup,
that is starting a business, that is building a community, what you should do is you should do
everything possible to support them with that business. So if they have an events company,
you hire the events company because you need it anyway.
If they have a pizza store, you order from the pizza store. If they make fluffy kids products,
you buy all their kids products. You do whatever it takes to support them. You don't need to feel
the need to invest in things that you don't understand. But supporting our friends,
paying full price, not asking for discounts is a very important thing to do because that is how
you support them. You don't have to write them a check to invest in their business, but as a good
friend, you should support them with their business and then give them feedback on what they're doing
is right, but publicly.
That's good. Tangent. That's okay. Now you may say, well, Sean, all right, I get this tax. I get
this capital preservation. I get this tax efficiency. I get this yield, this growth. Tell
me how, have you actually used this in your life? Well, it's to the point where I was, I was talking
to our team about it, that I use every single day that it's become a second, become second nature
for me. I'll give you a very simple example. Let's just say many of you probably, you've probably
heard about this idea of, Hey, you know, you should go invest in a, uh,
ETF by the S and P 500 by the, by an index and just invest in the market. Well, you're probably
investing in some of the S and P 500 with an ETF like SPY or VOO, uh, from Vanguard that invest in
the broad based equity market. Well, let's put that through this filter. I don't know the exact
details of this fund because it's not in front of me, but, uh, we can make some assumptions.
If you take VOO as the broad market ETF index, it is capital preservation. Well, over time,
we've had decent capital preservation based on, uh, based on the, the S and P 500. So I'm just
going to give it 20 out of 25 because it's, it's done decently well, as long as you are able to
time when you take it out. Tax efficiency. Well, I don't think there's any tax efficiency associated
with this. I'm just going to give a zero because as the stock grows, it grows. Now, if it, if it
loses some money, you get some losses, I guess, but we really don't want to lose money. So I'm
going to give it a zero yield. I I'm unsure of the exact yield or the cashflow that you get from the
S and P 500, but it's not going to be significant. And the last part is growth. Well, definitely the
growth component is the S and P 500 is generally grown seven to 10% on average a year for the last
30 years. Okay. Well, let's take that as the, the growth component and give it a 20 out of a 25.
Well, now you have 20 for capital preservation, zero for tax efficiencies. I'll say five for
yield at 25 and say all 25 for growth. Well, 25 and 25, that's 50 out of a hundred. Now it allows
me to evaluate this. You may say, well, Sean, that's interesting. I don't know. I don't know.
But is there something better? Well, now the thing that is better that I was thinking about is
what other box can I activate here? I've activated the cap capital preservation box.
I have no tax efficiency. I've activate, I have no yield or cashflow. I've activated growth. Can
I add one more? So how I thought about it was, can I get the same general performance of the S and P
500? Let's say for my children, but can I get some cashflow? Which is why I, one of the ETFs that I
this is mine. And if you are interested, you should check it out, talk to your advisor,
make sure it's the right fit for you is SCHD. SCHD is a dividend paying ETF of some of the
highest dividend momentum based companies on the S and P 500. Now I still get growth coming from it.
I also get cashflow and dividend based on that. So now I'm able to actually enhance my equity
market return by still getting capital preservation.
By still not having a lot of tax efficiency, by still getting
cashflow and still getting growth. So you can actually take a simple idea that you already
have and then ask a question. Hey, how can I activate something else in this that could be
helpful? I'll give you another crazy example. If you like crypto, you may like this. I put the same
filter on to handle crypto. Capital preservation. Well, I don't know if you take Bitcoin. I don't
really know if I'm going to get preserving capital. There's a good chance it could go to zero.
Tax efficiency. By the way, on tax,
efficiency, there is not built in tax efficiency. However, if you did not know this, I'll give you a
tip here. If you own Bitcoin, this is for now, if you check with your advisor, but for now,
it is still treated like a security and it is not subject to wash sale rules. Meaning if you buy
Bitcoin for a hundred thousand dollars of Bitcoin and you're in, and you intend on holding that
Bitcoin and say the Bitcoin drops from a hundred thousand dollars to $70,000 and you have a $30,000
loss, but you intend on holding that Bitcoin anyway. Well, you could instantly sell the Bitcoin,
capture the $30,000 loss, harvest it, meaning you bank that loss and you can use it against
your other investment gains. And then you can rebuy Bitcoin for the same $70,000 again. So net net,
you bought it a hundred thousand. You have one Bitcoin. It dropped in value to $70,000. So you
have a $30,000 loss. You sold it. So you got the $30,000 loss and you re-bought it right away in
the next 30 seconds. And you still have your one Bitcoin.
So the nice part is you started with one Bitcoin and you ended with one Bitcoin 10 seconds later,
and you now have a $30,000 loss. That's cool. That's cool. Right now, at some point with all
this crypto legislation, I'm sure that change is coming. I don't know, but whenever I see crypto
go down, I sell it and I capture the loss and I've rebuyed back the exact same time. But so let's say
I still give it a 20 out of 25 for the, for the tax efficiency. If you know this idea, cashflow,
not really, unless you stake the Bitcoin growth, I'll give it a 20 out of 25. I don't know,
maybe it'll grow or not. So now I have a 40 out of a hundred rating on the security. Well, I,
I'm unsure. I don't know much about Bitcoin. Now I'm not saying that Bitcoin is bad. I'm just
saying I don't know much about it. And it's really hard for me to invest in something that I don't
know a lot about, especially when it gets volatile and things get tough. I don't know how to react.
I don't know how to manage my emotions. And so I try to invest in things that I actually know a lot
about.
But I'm also probably like you, I get FOMO. Man, if Bitcoin had a massive run and I didn't invest
in it, no matter what it would make, it would be hard for me. So what I did was I bought one
Bitcoin for my son and one Bitcoin for my daughter, and I put it aside. And every time it falls in
price, I just capture the loss. I just put it right back in. I always own one Bitcoin for my
son, one Bitcoin for my daughter. Now, if it goes bonkers, my son, my daughter win. If it doesn't
go anywhere, that was a flyer that I took overall. Last but not least, I'll give you one more example,
which I think will be helpful to you. I read this book, which you probably read called Rich Dad,
Poor Dad. And one of the key parts of the book that Robert Kiyosaki said was you should buy real
estate because real estate is the path to wealth creation. And Kiyosaki is right. He's a little
loony, by the way, from a political perspective, but he's right. The crazy part about that is
almost all of the wealth creation that has happened in the Western world has happened
through equity in businesses and equity through real estate.
And so when I was running our first real estate company, Telus, which we grew 10X in five years
and sold the business to Douglas Elliman, it was a $3.5 billion business. And we got it. We grew it
from $300 million to $3.4 billion in under five years. And I had access to a lot of off-market
real estate. So I was able to buy a lot of real estate. At one point in time, I owned 198 single
family homes, 198 real estate, pieces of real estate. And I will tell you, it was the most
stressful time in my life. And I thought, well, this is crazy. How do I do better with this?
So it had capital preservation. Yes. It had some tax efficiency. Yes. Not great, but yes.
It had some cashflow. Yes. And it had some moderate growth. And I was thinking, well,
how can I make this significantly better now? What if I had the same exact thing,
but my life was easier and I was able to get significantly better in one of those areas?
Well, I sold all my 198 single family investments and I turned it all into multifamily because the
capital preservation was significantly higher because you could insure the entire property.
The tax efficiency was out of this world because the US tax code allows you to have bonus
depreciation today. So I can almost write off the entire value of that against my ordinary income.
The cashflow is significant because based on the leverage that you can get, I started getting
significant cashflow checks. And growth, the growth is still moderate, but over the investments that we had,
right now, I'm projecting a double your money every five years, which is crazy. So if I invested
$100,000 today, it would be completely passive, meaning I would have operators run this. And in
five years, my $100,000 wouldn't be net net worth $200,000. Now, if I did that over a 20 year period
and I didn't have anything to do with it, that dramatically changes how I look at the world,
right? And I don't have any, I don't have to like answer a broken toilet call for 198 properties,
even though I had property management, it was still a pain. The reason I'm sharing all this
with you is to realize that there is a framework for evaluating an investment,
and if you can't do it live, you get paralyzed,
you get stuck and one of two things happen.
Number one is you get paralyzed
and so you don't make any moves,
you don't actually do anything
and so you leave good opportunities
even though they may be good ones for you.
Second, you evaluate the opportunity and you get stressed
and you just make them out of fear or stress
because you don't have a framework for evaluating it
and then you make a bad decision.
I recommend just internalizing this framework for yourself.
Think about it as here's the x-ray,
capital preservation, tax efficiency,
yield, which is cashflow and growth.
So the next time you get pitched on a investment
or a big idea or you hear some investment advice
from a guru, remember that this is good enough
for a billionaire from Goldman Sachs,
it's probably good enough for you.
Podcast Summary
Key Points:
43% of Americans get financial advice from social media, but 80% of it is incorrect, highlighting a critical lack of reliable investment guidance.
The "Investment X-Ray" is a four-part framework—capital preservation, tax efficiency, yield (cashflow), and growth—that helps evaluate investments objectively and systematically.
By scoring each component on a 25-point scale, investors can quickly compare options and avoid emotional or impulsive decisions, especially when faced with high-risk or unfamiliar opportunities.
Summary:
A growing number of Americans rely on social media for financial advice, much of which is inaccurate, leading to poor investment decisions. To counter this, a proven framework called the Investment X-Ray is introduced, offering a structured way to evaluate any investment. This framework consists of four key components: capital preservation (ensuring your investment doesn't lose value), tax efficiency (leveraging tax benefits such as 401(k)s or 1031 exchanges), yield or cashflow (whether the investment generates passive income), and growth (its long-term appreciation potential).
Each component is scored on a 25-point scale, allowing for a total 100-point evaluation. This method enables investors to objectively compare options, avoid emotional reactions, and make data-driven decisions—especially when considering high-risk or unfamiliar ventures like startups or crypto. The speaker illustrates its use with examples such as gold, S&P 500 ETFs, Bitcoin, and real estate, showing how each investment scores differently across the four dimensions.
The framework is not just theoretical; it is used daily by the speaker and his partners to assess opportunities, manage risk, and optimize returns. Ultimately, the Investment X-Ray empowers individuals to reject poor advice, avoid impulsive decisions, and build more rational, long-term financial strategies—even without being a financial expert. It serves as a vital tool for anyone navigating complex or uncertain markets.
FAQs
The Investment X-Ray is a four-part framework for evaluating investments: capital preservation, tax efficiency, yield (cashflow), and growth. It helps investors make more informed, balanced decisions by systematically assessing each component.
Capital preservation refers to protecting your invested amount from loss. It involves understanding the risk of losing part or all of your capital, ensuring you know how much of your money is at stake before investing.
Tax efficiency means minimizing tax consequences of an investment. For example, retirement accounts like 401(k)s or 1031 exchanges provide tax advantages by allowing tax-deferred growth or deductions, which can significantly improve after-tax returns.
Yield or cashflow refers to the income generated by an investment, such as dividends or rental payments. It indicates whether the investment pays you over time, which is especially valuable for passive income goals.
Growth measures the potential for an investment to increase in value over time. For example, the S&P 500 historically grows by 7–10% annually, while gold may grow during economic downturns but has limited predictability.
Yes, it can be applied to anything from stocks and real estate to crypto or startups. For instance, gold scores highly on capital preservation but lacks cashflow and tax efficiency, while startups may score high on growth but zero on capital preservation and tax efficiency.
Chat with AI
Loading...
Pro features
Go deeper with this episode
Unlock creator-grade tools that turn any transcript into show notes and subtitle files.