Kevin Oly’s Blueprint for Wealth, Entrepreneurship, and Life: Lessons from a Self‑Made Millionaire

Q: Entrepreneurship: Who Can Succeed?

- Only about one‑third of people possess the mix of risk tolerance, focus, and luck needed to become successful founders. - The rest can thrive as high‑performing employees, but they will never enjoy the personal freedom that entrepreneurship can provide. - A defining moment (e.g., Kevin’s firing from an ice‑cream shop) often separates those who choose to own the business from those who scrape the floor.
Q: Signal vs. Noise: The Core of Execution

- Inspired by Steve Jobs, Kevin stresses a **signal‑to‑noise ratio** of roughly 80 % signal, 20 % noise. - Each day, identify the 3‑5 critical tasks that must be completed in the next 18 waking hours; everything else is noise. - Leaders like Elon Musk and Jeff Bezos operate with an even higher signal ratio, eliminating distractions to maintain relentless execution.
Q: Hiring, Diversity, and Women‑Led Success

- Kevin believes only a fraction of candidates can execute; he tests hires on real projects before offering permanent roles. - His teams are deliberately diverse, with a strong bias toward women (especially Asian women) because: * Women‑led startups in his portfolio achieve higher long‑term returns. * Female CEOs tend to set realistic growth targets (15‑16 % vs. 30 % for men) and maintain low attrition. - Listening more than speaking (2/3 listening, 1/3 speaking) dramatically improves managerial effectiveness.
Q: Real Estate and Mortgage Discipline

- A house should never cost more than **one‑third of gross income** (mortgage + maintenance). Exceeding this leads to financial strain, especially when rates rise. - For young, single professionals, buying a home solely for personal use is discouraged; focus on a diversified investment portfolio until a family need arises.
Summary Date: 2025-11-21 21:43:26
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4 min read
Kevin Oly’s Blueprint for Wealth, Entrepreneurship, and Life: Lessons from a Self‑Made Millionaire

Early Influences and Investment Philosophy

Kevin attributes his core investing rules to his mother, Geette, a Lebanese‑Irish immigrant who built a 55‑year‑old portfolio by: - Investing only in dividend‑paying large‑cap stocks and telco bonds. - Limiting any single holding to 5 % of the portfolio and any sector to 20 %. - Reinvesting only the income (dividends/interest) and never touching the principal. He later turned this simple diversification rule into a company that helps people grow wealth with the same constraints.
Entrepreneurship: Who Can Succeed?

Only about one‑third of people possess the mix of risk tolerance, focus, and luck needed to become successful founders.
The rest can thrive as high‑performing employees, but they will never enjoy the personal freedom that entrepreneurship can provide.
A defining moment (e.g., Kevin’s firing from an ice‑cream shop) often separates those who choose to own the business from those who scrape the floor.
Signal vs. Noise: The Core of Execution

Inspired by Steve Jobs, Kevin stresses a signal‑to‑noise ratio of roughly 80 % signal, 20 % noise.
Each day, identify the 3‑5 critical tasks that must be completed in the next 18 waking hours; everything else is noise.
Leaders like Elon Musk and Jeff Bezos operate with an even higher signal ratio, eliminating distractions to maintain relentless execution.
Hiring, Diversity, and Women‑Led Success

Kevin believes only a fraction of candidates can execute; he tests hires on real projects before offering permanent roles.
His teams are deliberately diverse, with a strong bias toward women (especially Asian women) because:
Women‑led startups in his portfolio achieve higher long‑term returns.
Female CEOs tend to set realistic growth targets (15‑16 % vs. 30 % for men) and maintain low attrition.
Listening more than speaking (2/3 listening, 1/3 speaking) dramatically improves managerial effectiveness.
Real Estate and Mortgage Discipline

A house should never cost more than one‑third of gross income (mortgage + maintenance). Exceeding this leads to financial strain, especially when rates rise.
For young, single professionals, buying a home solely for personal use is discouraged; focus on a diversified investment portfolio until a family need arises.
Diversified Portfolio: Stocks, Bonds, Crypto, Watches

Primary allocation: low‑cost S&P 500 ETFs for broad market exposure.
Fixed‑income: telco bonds or Treasury bills, shifting toward more bonds as you age.
Crypto: ~20 % of the portfolio (Bitcoin, USDC, exchange stocks) as a separate sector that will eventually become a standard S&P component.
Alternative assets: high‑quality vintage watches and gold, which can appreciate significantly over time.
Role of Marriage and Financial Compatibility

Financial stress, not infidelity, is the leading cause of divorce.
Partners should disclose spending habits early; Kevin categorises potential spouses into seven “money love languages” (e.g., the “spender‑holic,” the “thief,” the “meanie”).
Marrying a financially disciplined partner (the “meanie”) dramatically improves wealth preservation.
AI, Crypto, and Future Technologies

AI is reshaping every industry; Kevin uses AI for market research (e.g., wine varietal demand) at a fraction of traditional cost.
Stablecoins (USDC) will become a low‑fee, instant payment method, separating the utility of crypto from speculative Bitcoin investing.
Control of semiconductor “queen‑bee” chips and the surrounding developer ecosystem is a national security issue; losing that control hands the “honey‑bee” talent to adversaries.
Practical Advice for Young Entrepreneurs

Apprenticeship – Spend 24 months working for free or low pay in a sector you love to learn the cogs before launching.
Fail Fast – Expect the first venture to fail; the experience raises the probability of later success.
Prioritise Signal – Daily, list 3‑5 high‑impact tasks and protect them from distraction.
Test Your Team – Hire contractors first; only promote those who deliver without supervision.
Stay Authentic – Align any brand endorsements with products you actually use; authenticity preserves long‑term credibility.
Final Reflections

Kevin emphasizes that wealth creation is a matter of discipline: consistently saving, diversifying, and avoiding unnecessary consumption (e.g., $28 lunches). He also stresses that happiness is not a destination but the result of repeatedly achieving meaningful goals.
Discipline, focused execution, and choosing the right partners—both in business and in life—are the true levers for lasting wealth and freedom.
Full Transcript

That is the stupidest thing you can ever
do.
What is the most important thing for
someone who's just trying to grow their
money?
So, I learned this from my mother and I
actually built a whole company around
it. Yeah, there she is. So,
I haven't seen that picture in a while.
Damn. I mean, what she did, the
performance was extraordinary. And with
that, she put my brother and I through
college. She took care of her family
when they fell on hard times. When I saw
the results, I said, "That's it. That's
how I'm going to invest for the rest of
my life."
So, talk me through this. I want as much
detail as possible.
Okay, let's start with this.
Kevin Oly aka Mr. Wonderful, is the
self-made millionaire and investor
who's built and sold companies for
billions. There's a lot of people don't
like me for my blindness. I don't care
because there's people that don't think
ahead and find themselves mired in debt
but then pissing away money spending $28
for lunch. I mean that's just stupid.
What about a house?
The mistake that people make is they buy
too much house. Never let the mortgage
and the cost of maintaining the house be
more than 1/3 of your income.
Now how much does the person that you
fall in love with have an impact?
You kidding? It's everything. And I did
some research and most marriages can
survive infidelity. They can't survive
financial stress. But if everybody
that's listening does this one thing,
you will have over a million and a half
dollars.
Kevin, can anybody be an entrepreneur?
No. Only a third of people can become
successful entrepreneurs because there's
a couple of things that you must achieve
to be successful. First,
[Music]
Kevin, I'm going to ask you to do
something which is quite difficult
because I'd find it quite hard if
someone asked me to do this. But before
we get into the detail, can you give me
a 30,000 foot view on your
entrepreneurship and investing career?
Just the just the three bullet points
that are most pertinent before we dig
into those specifics.
Every entrepreneur I've ever talked to
um that finds himself where I am today
has has a defining moment where they are
pushed into this path. It's it's
something they can remember and they
remember it in perpetuity. And I'll
remember my moment getting fired in an
ice cream store. That simple. First day
on the job, asked to serve and scoop ice
cream. And um I did that all day. But
when people sample ice cream, they get a
taster and they take their gum out and
they throw it on the floor. Somebody's
got to scrape the gum off the floor at
the end of the day. I only took that job
because I was very interested in a girl
who's working in the shoe store and I
figured
I could, you know, hang out with her
afterwards. And uh I saw her waiting for
me and the woman who owned the store
said, "You've got a scrape to come off
the floor." And I didn't want her to see
me on my knees with a scraper. Bad for
my brand. I was in high school. And uh
she said, "No, no, you have to do it."
And I said, "You know, you hired me as a
scooper, not a scraper." She said, "Um,
how about you're fired?" And I didn't
know what that meant. And it was the
defining moment for me because I
realized there's two kinds of people in
the world. There's people that own the
store and there's people that scrape the
[ __ ] off the floor and you have to
decide who you are. And I'm not saying
being an employee is a bad thing. Not at
all. But for me, um, it it hit me. It
just hit me.
Kevin, there's a present for you. We
give a present to all of our guests.
Really?
Underneath that black
Can I open it?
You can open it.
I just take this off.
Oh, look at that.
You've heard the story.
That is exactly how it looked except it
was black gum and that was exactly the
tile. It was just like that Mexican
tile. That's really freaking me out.
So you were asked to scrape gum off a
Mexican tile
just like that. And in order to do that,
you got to get down on your knees and do
it. And um I just couldn't do it. And I
and I and then you know the rest of the
story. I eventually could afford to
bulldoze the whole mall if I went to.
when we went back to meet her and thank
her for her pushing you off the
treadmill into that direction and she
was gone and there was a bodega there
instead.
You said there that you realize that
there's kind of two people in life.
There's the entrepreneurs, the person
that owns the ice cream parlor and
there's the person that scrapes it off
the floor.
Yeah.
That provoked a question in me which is
do you think anybody can own the ice
cream parlor? I do you think anybody can
be an entrepreneur?
No. I've tried to teach it. Um and I
mentor out it all the time to the CEOs
that I work with. Uh there are some
attributes of people that can do this. A
certain element of risk tolerance, uh a
certain element of focus.
And then the other element which I've
really started to believe in of late is
karma, luck. You need to be lucky. You
need It's like Napoleon was once asked,
"Who are your favorite generals?" and he
said, "My favorite generals are lucky
generals. My lucky generals." And I'm
starting to think that in life, um,
particular entrepreneurship, you look at
the difference, the path of success and
failure, and I nobody's exposed to it
more than I am in terms of how many
investments I may have made over the
decades.
I think if you want a percentage, you
know, I teach these cohorts at Harvard.
I'm an executive fellow there. I'm very
proud of that work.
You get a class of 120 people in a room,
twothirds of them want to become
consultants. That's why they're there.
And lead a life of mediocrity and never
make a decision of consequence in their
lives. And after 24 months, they are
tainted with that disease forever.
They'll always be good consultants, but
they will never achieve greatness in any
way. In life, only a third of people can
become successful entrepreneurs. That's
it. And the rest can be very successful
employees. And there's nothing wrong
with that. You can have a fantastic
life. You won't be shackled to the, you
know, the the ups and downs of
entrepreneurship, the challenge of it,
how hard it is, but you'll never be
free. And that's the debate. That's it
right there. Do you want personal
freedom? It's the only path. That's it.
It's the only path.
It is the only path. I mean, you can't I
I've always said it's not about the
pursuit of money. It's not about the
pursuit of greed. You will fail if you
do that. It's it's the undying love of
freedom.
So that one-third of people that you say
will be successful, they'll pursue their
their dreams, they'll build a business,
whatever it might be.
Yeah.
Do you think it's possible for us in
this conversation to increase the
probability of their success? You said
you don't think you can you can make
someone an entrepreneur,
but is there things you can do to
increase their probability of success?
Yes, there are a couple of things that
you must achieve to be successful. And
let me explain what they would be. And
this is not some academic study. This is
real data from real situations of real
CEOs I've worked with and learned from
because I used to work for guys like
Steve Jobs and others in my career.
Let me um let me give you one that I
think is very important. We'll start
with this one. I used to work for Steve
Jobs in the early 90s making all of his
educational software. I mean it was just
Oh, there they are. My goodness, you
guys do good research. Those are the
kind of things that we did for him, you
know.
Yeah. Yeah. All of that. It's hard to
find. Those are senior realms. But, you
know, in developing that software,
we used to go quarterly. Um Heidi Rosen
was there in the room. She's still a a
very famous venture capitalist.
And I would say, Steve, you know,
we got to do some market research on
Oregon Trail. I mean, it's a huge title.
It's in 110,000 school buildings. We got
to do an update. It's going to cost you
12 15 million bucks. We want to find out
what the students want. We want to find
out what the teachers want. Want to find
out what the parents want. Steve would
say, by the way, not a nice guy. Not a
nice guy. He would say to a room full of
people, Kevin, I don't give a [ __ ] what
the students want or the parents think
or anybody thinks. It's what I want.
They don't know what they want till I
tell them what they want.
And I said, "Steve, you sound like such
an [ __ ] You have no idea what that
sounds like." He says, "No, no, that's
how it is, Kevin. Now, are you making
money with me? Are we Are you Am I your
fastest growing OEM? Have we not been
wildly successful and continue to be?" I
said, "Yes, Steve, that's true." He
said, "Then [ __ ] shut up and do what
I say."
That's how he would talk to you.
100%.
And here's what I learned.
Look how wildly successful he was. But
here's why.
There's a concept that he understood
that very few people focused on back
then in the early 90s of signal to noise
ratio.
What was so brilliant about Jobs
that I tell every CEO now and I don't
care if you're an S&P 500 CEO or you're
just starting a business.
His vision of Signal was the top three
to five things you have to get done in
the next 18 hours. Not your vision for
the business next week or next month or
next year. Just the next 18 hours you're
awake. You're going to get those three
things or those five things done that
you have deemed critical for your
mission. They must get done today.
Anything that stops you from doing that
is the noise.
So this signal to noise ratio to be
successful for Steve Jobs was 8020. 80
signal, 20 noise. And I knew that to be
true with him because he would email me
at 2:30 in the morning expect me to get
back to him because back then we didn't
have texts. It was all email.
He was right. He was right. And the only
other person that I've seen that has a
higher ratio than that
is Elon Musk. He has no noise. He does
not deal with noise. He is 100% signal.
24 seconds of, you know, every cycle. I
mean, the guy is just 60 seconds of
every minute, 60 minutes of every hour.
The 18 hours he's awake, it's all
signal. And look what he's achieved.
Now, it's very awkward for him socially.
Because noise is dealing with your
family sometimes or noise is saying hi
to a friend or noise is is is listening
to some doom scrolling on you know some
social media app that just takes your
mind or maybe playing your guitar but
very few people on earth and if you go
back in history you're going to find out
that the geniuses of their time we're
close to 100% signal
and so I can really sort of summarize
this for my audience signal is the most
urgent thing you should be focused on
right now and noise is bas basically
everything.
No. The goals you set for that the the
weight the that you were awake if you're
going to be awake 18 hours.
Yeah.
And you've determined that there's three
things you have to get done. You're
going to get those done. No matter what
it takes, you're going to get those
done. And you're not going to let
anything distract you from those three
to five things. If you're a CEO and you
achieve that and you can get those done
with 80% of your time based on that,
you're extraordinarily successful. You
are absolutely and you're Steve Jobs or
you're an Elon Musk or you're somebody
if you if you even talk to Bezos I don't
know him personally but I've heard in
many interviews like I knew you know
I've I've met Elon just a few times I
spent a lot of time with Jobs but they
say the same thing Bezos will not make a
decision after 1:00 in the afternoon
because he felt that the noise was too
high the signal for him was in the
morning hours it this is a crucial
aspect of success
that that I now understand to be the
ability of of of it defines an
entrepreneur. A man or woman that
understands a signal noise ratio that
focuses on that, they'll be successful.
The ones that can't that get down to a
50/50 signal noise, they'll fail. It's
that simple. And it's a very simple
concept.
You know, you made one of your things
today this interview. You're going to
get it done. You're going to all these
people around and everything else. This
is one of the three to five things
you're going to get done. I have five
things today. I'm going to get them
done. I'll do the same thing tomorrow
and the day after that. And you have to
decide how much signal you need to get
those three to five things done. And for
jobs it was 80%.
What's the opposite of that? Sometimes
looking at the opposite helps us to
understand something. So the opposite of
having you know
I hire managers and CEOs that have a
balance in life between the discipline
the binary aspect of business which is I
make money I lose money and the chaos of
the arts or some other pursuit dance
painting photography collecting crystals
whatever it is that that they that they
have that balance you you need you need
the ying and yang in your mind to make
correct decisions. It doesn't mean it
takes you off the signal. The signal is
you got to get stuff done. But how do
you live your life? And so I spend a
fair amount of my time practicing my
guitar or working with my photography or
my my watch, you know, up tonight, very
late tonight, I will meet a master watch
maker and we will deal with the design
of a new piece unique he's going to make
for me and I'm going to love that
moment. That's going to be something
completely different to what I did all
day long. And we'll start our journey
together over the next two years to make
this piece unique. And that's something
that just takes me away from all the
[ __ ] I'm going to be dealing with today.
And I also tell successful entrepreneurs
in the same day you will get a and this
happened to me today. It happens every
day. You're going to get a call from
some aspect of of your what you you call
it your empire, whatever you want where
your this company's going bankrupt. It's
just going to go bankrupt and you're
going to lose
I don't know 10 million bucks on that
deal.
And that's a piece of information you're
dealing with. Half an hour later, this
actually happened to me today.
One of my companies going public. It's a
450x for me.
The stock will get unlocked sometime in
the fall. But
how can how do you how do you fit that
together? Utter catastrophe,
destruction, woe, loss, utter euphoria.
half an hour later. That's
that's what my life is like.
That's entrepreneurship obviously on a
different scale for most founders.
Well, the founders deal with the same
thing. They get disastrous news. They
lose an account like a Costco or
something if it's consumer goods or
service and they get something else. The
the the eb and flow is is the management
of expectations and your ability
emotionally to navigate those ups and
downs is part of what entrepreneurship
is. But it goes back to the signal. It
can't take you off the signal. This is
what Steve taught me. Yes, it's great
news. Yes, it's bad news. But focus on
the signal, O Liy. Focus on the signal.
That's it.
Where does this analogy come from of
signal and noise?
It was his genius of of of making it so
simple. What are the three things you
got to get done today? What are they?
What are they?
How do you know what they are?
They will make themselves apparent. They
will definitely make themselves
apparent. They will make themselves
apparent and you will realize I have to
deal with that. You may have them set up
from the day before. I actually still
use sticky notes on my mirror. Got to
get these three things done and or five
whatever it is. But then something else
will hit. That's the skill of
understanding is that noise hitting me
or is that signal? There is the essence
of the great entrepreneur, the great
manager, the great leader. Is that
signal or is that noise? What is it?
That's what you're looking for. You're
hiring somebody that can actually
distinguish signal and noise because it
could be noise. It could be irrelevant.
You have to determine only you makes
that decision. That's the key right
there. This is what I teach
entrepreneurs and engineers and
this is the most important thing. It's
that judgment of prioritization but then
the sort of force of execution to get it
done.
Can you interpret signal and noise and
can you keep the noise away from from
the things you got to get done? That's
one. The other which is something that
I've learned over the last 5 years
and this uh you might find this
interesting but most of my particularly
the naent startups and you're you're
involved in the same format I am. You're
dragon stand in England. I'm a shark
tank in the US.
I you know you put up 500,000 or a
million bucks into somebody's business
eight out of 10 is going to fail maybe
six out of 10 depend you just don't know
and I love it when people tell me oh I I
know when I make an investment it's
going to work
so full of [ __ ] they have I'm talking
about startups they have no idea what's
going to work and you won't know for 5
to seven years which is why you need
divers diversification in the portfolio.
But
I would go as far to say now, you know,
when I meet um venture capital firms and
young analysts that work there and they
think they're so damn smart. They've
never operated a business, they know
nothing. They have no idea what they're
doing. They're going to hope that one or
two of their portfolio uh is going to
work out in seven years and pay for all
the other mistakes. But the
serendipitous nature of success in
entrepreneurship is brutal. It is. So
that does that mean though that it's I
guess I was going to say does that not
mean that it's highly luck? Investing is
highly like entrepreneurship must be
well I said karma you know I call it
karma but you need executional skills
but here's another skill that I think we
should talk about um
when you look at at least my experience
over decades of making these
uh naent these early stage investments
these around investments remarkably and
I've done them in all 11 sectors of the
the economy the majority of the
successes five to seven years later are
companies run by women. Why is that? Why
is that?
And so they don't know each other.
They're in different sectors. They never
meet each other. Why is that? And I have
come to the conclusion um
two things. They set goals that they can
achieve so that in the early stage of
their businesses, they put growth rate
targets like 15 16% versus men at 30%.
Very often men hit their targets 65% of
the time. at least my portfolio and
women 90 [ __ ] plus percent of the time
and that keeps the the the team very
sticky. They want to be part of a so
they don't have a lot of attrition when
they're small. They don't lose the head
of financing and marketing that that
works but they have another attribute
and this was pointed out to me by one of
my female CEOs a few years ago to me.
She said, you know, Kevin, you talk too
much. You talk too much. Um you talk
two/3s, you listen one third. Why don't
you try reversing the ratio?
She said that to you.
Yeah. Yeah.
[Laughter]
I'm very thankful actually because I
tried it and um she's right. If you
don't talk and you listen, you become
far more effective as a manager or an
investor in my case by getting
information that you weren't going to
get by talking. And so if you go into a
room,
I just did this a few minutes ago before
I came here. I'm involved in a
litigation and we decided to attempt
settlement talks which is why I was a
few minutes late and um
you know we knew we were going in there
to settle and it it's long protruded you
know long it's a long long long
uh litigation
and I remembered her as we sat at the
table like this there were other people
in the room but the two uh you know were
across from each other. I just looked at
him. I understand
for a long time,
a long time. And it gets uncomfortable
and no one else is talking,
you know, just looking.
And um
maybe after 90 seconds, he blurted out
something he shouldn't have said.
And I knew exactly what the price was
right there.
That was the end of it.
You learned that as a podcaster.
You learned that there's actually
something going on in the silence.
There is something going on in silence.
And it's it's it's the number that he
was going to settle at.
He showed his hand.
So, we saved ourselves two hours. You
know, it's a it's an attribute that many
people can't do because they can't stand
the social uncomfort of it. I have no
problem with it. I could sit here and
look at you for 10 minutes. it wouldn't
matter to me. And I've actually found it
to be a very useful piece of
information. It's not just a
negotiating, but to listen to employees,
listen to investors, listen to
financeers, listen to alternative ideas
to yours
and become more powerful from it.
You're in the very business of people
selling to you and pitching to you. We
both sit on a similar show where people
come in and pitch to us. You're seeing
at times 10 to 12 pitches a day. So
you've developed this muscle over the
last couple of decades now almost this
instinctive spidey sense of when an
entrepreneur will be successful at least
in the context of securing investment.
What have you come to learn about the
the attributes of the ones that are
successful? Is there is there anything
one can take from that
in the moment when that entrepreneur
comes out onto the carpet in the context
of Shark Tank or Dragon's Den even
they need the setup shot of the product
with the entrepreneur and they have a in
our case a steady cam or a jib that
comes down and shoots it. So the the
stage director,
Eric, uh is his name. I've worked with
him for years. Says to the entrepreneurs
I've never met, usually it's a team or
it's a family or it's whatever. Three or
four, two people, whatever. Hold.
Hold. Don't speak. Hold. Hold. Don't
mind the camera coming into your face.
Hold. Hold.
Maybe for two minutes.
And I'm right there in front of them.
I'm 12 feet from them. And I just look
at them. Not smiling, not blinking, not
frowning, just looking at them.
And before they say a single word, I
know if they're winners or losers. Just
like that. And why is that? Why is that?
When? And I'm right probably 99% of the
time. Maybe I get it wrong one out of a
hundred. I doubt it though.
You walk in a room, even though you've
practiced, you know, you in the context
of of Shark Tank, 20 plus cameras, a
billion plus dollars in in the five
chairs there. You've been practicing for
months your pitch, but it wasn't the
real deal. Here you are, cameras are
rolling, tape is running, you know,
you've only got so many minutes.
This is your moment. And you're on
national television. 100 plus million
people will see you in syndication. It's
all in your mind. It's all in your mind.
It's going through your head.
Can you project
who you are with your eyes and the way
you're standing? Can you project your
confidence? Are you looking at the
ground? Are you looking away from me
because you can't stand me looking at
you directly without saying anything to
you? Or do you push back? Or did you
say, "I'm gonna I'm gonna stake my aura.
I'm gonna stake my ground here. I'm
gonna show you I'm ready."
You see what I'm getting at?
Yeah.
And I can feel it. I can see that
they're ready to do battle. They're
ready to answer. They're ready to
present. They're ready. Ready. Ready.
Ready. Or they're not. And I've taken
that out of the Shark Tank. I see that
every day in life. I see it. So you have
to learn how to project yourself in
front of your peers or who's who you
want to you want to lead or teach or if
you're a general or a preacher
that is maybe
an innate something you're born with or
maybe you can learn that I don't know I
don't care but if you don't have it
you're going to fail and you're just
that's before a word is spoken
before the first word is spoken. And so
then what has to happen?
Then Eric says, "Go. You're on." And
everybody's just sitting there looking
at you.
Can you articulate your idea in 90
seconds or less? Can you whatever props
you have or whatever you're going to
say, can I get the big idea right away?
The ones that had that aura generally
get there. 30 seconds later, I get it. I
get what they're here for. I understand
their product. Okay, that's good.
Unfortunately, great ideas are a dime a
dozen. I mean, there's millions of them.
The next phase begins. This is after 90
seconds. Can you explain why you're the
right person to execute on this idea and
create a business from it? Because you
know something about this space? You
worked for a competitor. You've tried
three times before and failed. You
figured out what you did wrong. What is
it about you or your team that can take
this
idea and make it happen? Now, when you
get those two things together, you can
feel the aura of the room. The isotope
is sizzling because you've derisked a
great idea. You got an operator in and
they But then the third thing, this is
the killer. This is the killer. I've
seen it so many times in real life and
Shark Tanks real life it is. it.
You got to know your numbers. How big is
the market? How fast is it growing?
What's the gross margin? I mean, I've
said this a million times to people. I
teach this every day. How many
competitors are there? When are you
going to break even? What month? If you
get the first two right and you don't
know your numbers, you deserve to burn
in hell. And I'll put you there myself.
I mean, you wasted an opportunity for an
entrepreneur that did know their numbers
that could have been in that spot that I
could have invested in. You don't know
your numbers. I take you out behind the
barn and shoot you. You should have
brought somebody that understands the
language of business because those three
together are the definition of
leadership right there.
I've never heard someone talk about aura
in entrepreneurship quite like that. And
I was I was just trying to for the
people listening that are either trying
to figure out if they have an aura or to
grow that aura. What does it what does
it look and feel like? Is it physically?
Is it shoulders back? Is it you said
it's eye contact? Or is it
indescribable? And do you think you
could take someone who doesn't have that
aura in business and teach them it? Does
business give you that aura?
I think you can teach it. I certainly
try and teach it to my children. Um I
try and teach it to my students.
And the best way to do it is to look at
yourself in the mirror sometime. You
know, just what do you look like to
yourself? You know, if you're going to
go make a presentation to take down a
million-doll line of credit or
something, you want to dress the part,
obviously, but you're going to walk in a
room with, you know, a loan officer and
maybe an assistant, maybe one other,
depending on the size of the deal, and
they'll have never met you probably, and
you're going to have to project yourself
in those seconds as you're walking up to
shake their hands.
What does that take? It takes an aura of
confidence. And it's in the eyes. It's
in the way you're you're standing. It's
in how the way you're dressed. It's it's
not a joke to be dressed for success,
you know. It's it's um
it's
but it's it's something about presenting
yourself and keeping your eyes focused
on who's talking to you so that they
know that you're absorbing the
information, that you respect the
information, that you're about to get
into a narrative with them of respect
even though that there may be
disagreements. All of this is happening
in the first 60 seconds. And it's
setting up for the rest of your life
with that person. It could be who you're
going to marry. It could be who you're
going to work with. It could be your
partner in business. It could be your
banker. It could be anybody. It could be
a soldier that's going to give up their
life for you. It's sort of who are you?
That's it.
Just closing off on the point you made
about women being your most successful
investments and the companies that have
given you the greatest returns tend to
be
led by women. Does that mean that you
focus on hiring women into executive
roles?
Yeah, I'm practically all women. Um,
particularly Asian women. I am a uh, you
know, this whole thing about DEI and all
this stuff. I've always had diversity
because I only hire on merit. I don't
care if what sex you are or what you
call yourself or what where you came
from or the color of your skin or what
planet you were born on. I couldn't give
a [ __ ] Can you execute?
And the way I hire people, and that's
why I have such a diverse staff in my
operating company, I don't hire you. I
say, "Look, you sound good, and you look
great on paper, but that doesn't mean
anything if you can't work within the
team. So, I know you want a job and you
want benefits and all that stuff, but
I'm not going to do that. If you want to
be part of my universe, you're going to
work for four to six months as a
contractor at a much higher salary.
because you're not going to get any
stock options, you're not going to get
any uh benefits. But I just want to see
what it's like for you to work with all
of the people that we deal with every
day. All the lawyers, all the bankers,
all of the, you know, the CEOs that we
have investments in and and your
co-workers because I don't do 9 to5
anymore. I do projectbased work. I don't
care where you live. We have people
working in Dubai, Abu Dhabi, uh England.
I mean, everywhere. everywhere and and
you know we meet we try and find an hour
every week where we can see each other
but we're just constantly communicating
using modern day tools today but
you know can you actually be given a
mandate and execute on it that's it I
don't care when you do it if you have to
get the financials out let's say you're
running in finance you got to get them
out the 15th for taxes I don't care when
you do it but if you miss the 15th I
care so I I need to find out if those
people can fit into that kind of an
environment. Some of them make it, some
of them don't. Some sometimes we know
right away after 90 days, let's hire
them, bring them in the team, and you
know, let's give them the whole package.
And sometimes after a month, we say,
"No, it's not going to work. Here's
like, you know, that's it." I think I
think more companies should do that.
Actually, it's more like the Swiss
apprentice system. They bring you into a
lot like, you know, my stepfather's
Swiss. I've been going to Switzerland
for 50 years. So if you're a giant
company like a Fiser or a Nestle, you
pull them out of high school at 14. You
give them a job in the afternoon. They
become an apprentice. They want to
learn. They want to work. They want to
understand what it's like and then you
find the the winners at while they're
still in high school. Then you give them
summer jobs and then you bring them into
the company. That's where I got the idea
from. The Swiss are genius that way
because you're sort of mitigating the
risk. I guess you're taking less of a a
risk on No, but you're also finding out
if their their DNA is going to fit with
your I mean, I want my team to make a
ton of money. I I just I want them to be
successful. I want every person to be
proud to work with the other and and
just we're almost invincible. We're so
damn good at what we do. You have the
same thing here. You you don't have
people that don't work for you. Well,
you get rid of them. You whack them. I'm
more just formal about it. Boom. You're
gone.
With with the investments that you've
made, how many investments How many
offers have you done on Shark Tank now?
probably like 800
we know we don't even count it anymore
we look at the portfolio rolling over a
5 to sevenyear period
a lot like a lot and and the thing is
the thing what I've learned is you get a
you get an exit like uh base pause from
five years ago or something
remarkable woman
that was the the cat DNA thing
the cat DNA thing I mean nobody saw that
coming I thought the thing was a joke um
I was so wrong I mean that's the whole
point and and She she had the highest
IRA I think in the whole format's
history. Nobody's made her She was
around for 36 months and taken out at
such an extreme number in all cash that
there was an NDA signed between Sony and
the the pharmaceutical company. I can't
even tell you what it was. It was
extraordinary. It was extraordinary.
Was it nine figures?
Believe me, it's a tough NDA because and
I understand why they did it. They
didn't buy it for the cat DNA testing.
They bought it for the data
with AI didn't really wasn't emerging
then. It existed but it wasn't with the
data they have now. They can develop
products for animals that are
extraordinary in terms of feeds and
medicines.
Yeah.
And nobody had that much data on the 110
million cats in America because she got
it all during the pandemic. thousands
and thousands and thousands of of of you
know it was it was never about it was it
was a data company. It's like my son
telling me when he got his internship at
Tesla, "Hey dad, it's not a car company.
It's a data company."
Buy the stock. I said, "I'm never buying
the stock. It's a joke. It's so
expensive." He said, "You're an idiot.
It's not a car company." So I bought the
stock and he was right. It became my
most successful investment. I I had to
keep selling it down to 5%. My cost base
is zero on Tesla now.
[ __ ] hell.
Yeah. Before it split and he worked
there for 5 years.
One of the personas that I have that
watches this show a lot are young
people, not always young, but that are
on the sofa thinking about being an
entrepreneur and they talk about it a
lot. You know, they they come up to me
in the street.
Twothirds will never do it.
Twothirds will never do it.
That you you might as well do it when
you have less burdensome risk like a
mortgage in a family. You might as well
do it in your 20s. You're going to fail
the first time, maybe the second, maybe
the third. You only need one success.
You I had plenty of failures and I I
still have failures. I mean, it's just,
you know, that one I talked about this
morning. It's, you know, when I I you
know, I I said to the largest
shareholders as was I was in the car and
your assistant was, you know, at looking
at me in the limo. I was telling the
other two shareholders, "Listen, guys,
it's it's a binary decision. As soon as
I get out of this interview, we're going
to make a decision.
This company's going bankrupt." Oh, on
the bankrupt company.
Yeah. Yeah. And so if we want to save
it, everybody's going to have to pony up
x million. And um we're going to own the
whole thing. We're just going to own it
all. We're going to we're just going to
do a cram down round at a fraction of a
cent. We're going to own the whole
thing. You want to do that or you want
to let it go bankrupt? You guys choose.
I'm onethird of it. So it's going to
have to be, you know, two against one.
And I'll do whatever they want because
that's how I am. But it's, you know, you
want to get yourself in a position in
life. I think most CEOs understand this.
You are going to have bad outcomes.
There are going to be bad outcomes. But
never put yourself in a situation where
one bad outcome defines who you are. I
mean, for those shareholders, they're
going to be unhappy. But then I got the
call on the IPO. Those shareholders be
very happy. They're going to make 400
400x. So it and that was one of my
deals. And so it's sort of like
learn to live with the idea that
you're going to fail. You're going to
lose money by taking risk.
Will it change relationships
permanently? Maybe. But if there if
you're respected and you're honest and
you're transparent, probably not. I
think there's a lot of people don't like
me for my bluntness. I don't care.
I think a lot of people respect me for
my blindness. They may not like me and
you know it's sort of um it doesn't
matter because the only people that
really matter to me are probably my
20iest closest friends in my family.
Do you think if you hadn't worked with
or known Steve Jobs you would be a
different person?
100%. Steve changed my life. There's no
question.
I didn't like him. But
I feel so bad that he he didn't have to
die that way.
He just wouldn't go with the modern
medicine at the time is my view. Guy was
a freaking genius.
He was so smart in terms of keeping on
track to get getting stuff done and look
what he achieved. But he was
difficult
difficult because he wasn't always
right. But he was right so much that the
mistakes just didn't matter.
And I thought, you know, the people that
spent enough time with him know what I'm
talking about. Um,
you know, it occurred to me because I
know Waznjak too, not as well as Jobs,
but they really needed each other. They
really needed each other because W
understood he was he understood what the
let me draw an analogy here for you. I
think it's a good one.
take the situation going on right now
with
Nvidia, AMD, to a certain extent Intel,
um maybe Broadcom,
where policymakers in Washington have
decided that we can't sell those chips
to countries like China or Russia or
whatever the list is of adversaries.
That's bad policy.
And here's why. What I learned from
from jobs was
the the computer, the chip is the queen
bee. It's it's the it's the queen bee.
But it has no value without the
honeybees, which are the programmers
around it that form a community that
spend all of their energy
writing code that works with the queen
bee, which is the chip that pushes out
its influence. Because every coder that
becomes familiar with that firmware,
that Bosnjak computer, writes to that
platform, is part of the honeybees.
Jobs understood that. He said, "I've got
to get every honeybee writing for the
Mac,
writing for the OS of Apple."
It's the same with
the Nvidia chip.
We need to sell it to everybody. Every
even adversaries because within
that country of Russia or China is some
genius kid. You don't know who he is or
she is that's going to write the next
piece of firmware or advanced AI
from the queen bee,
the chip, the American queen bee. The
minute you shut down a market and you
don't, your adversary sends their queen
bee in, which is Huawei.
We can't let that happen because I don't
think the lawmakers understand what jobs
understood. You create the hive with the
queen in the middle. That's the chip.
You convince every bee around
to make the honey, which is the
software, and that is the AI in this in
this case. You make it off that chip.
And when you advance the chip, again,
everybody knows how to take that set and
stay within the American chip that
you're advancing.
Maybe you keep them one generation
behind. Maybe maybe that's the policy.
But you don't ever let an adversary put
their queen bee in the middle of the
hive. You see what I'm saying?
Of course. I mean,
and that is what Jobs did. That was the
war between Gates and Jobs on the OS, on
the operating system.
Yeah. I was thinking about the app store
and yeah,
it's the same thing. It's exactly the
same thing. And so, so when I see this
policy now,
I go out of my mind. I mean, the first
thing I do is get on a plane, go to
Washington because AI is so important
for all the investments I've made. I do
not want to be putting Chinese honey
into my companies at all. It's that
simple. So for that person that's
stewing over their ideas now, if they
had just a couple of minutes with you
and they and they asked you the
question, Kevin, I'm about to start this
business. I'm about to go on this
journey of trying to go from zero to
something in my life. Is there anything
else that I need to know as I set upon
this sort of next 10 years of my life?
I'm 21 years old. What what are because
I think every entrepreneur has like
their principles. You you talked about
one which is the signal versus noise
thing. Are there any other foundational
principles that you think are conducive
with success
that you might have learned?
Yeah, I mean I what I'm telling 20 21
year olds now is look,
go work for 24 months in a sector you
love that you're passionate about. Even
if they don't pay you, go in there and
be an apprentice. Um, if you're that
passionate, you're going to be able to
convince some manager to go work for
free in there. you're just they're going
to recognize your passion and they're
going to bring you in. Do that first.
Most young entrepreneurs say, "Nah, nah,
I don't want to work for anybody." I
said, "Yeah, you do actually. You you do
want to work for somebody. You want to
just understand how all the cogs move.
Just 24 months and after that launch.
The first one will probably fail. You're
going to start with your parents giving
you 10,000 bucks or whatever it is,
friends and family. But you will have
the baseline knowledge of your industry.
You will know who the participants are.
You will understand how it works and
you'll have a much higher probability of
success. But the key is to launch sort
of in your in your mid to early 20s
because you need to burn a few years
failing and and that that matters.
On the point of how to lead people, when
people hear about Jobs's approach, they
sometimes assume that you also have to
be an [ __ ] And this is the this is
the conflicting thing because the world
has changed since Jobs was in a
leadership position. Things have gone a
little bit more soft shall one say.
Have you seen all all types of
leadership win out in that regard? The
direct you know signal focused kind of
brash approach but also the kind
approach.
I don't think kind works. I think
respect works. I I the same number of
[ __ ] are out there being successful
now as they were back in the 90s. Um
it doesn't matter um whether you're an
[ __ ] or whether people like you or
not. I mean, people get so stuck on this
stuff. It it's
the team you're building are not your
friends. They are the team you're
building to execute on a mandate. Your
customers come first. They're more
important. And then of course the
employees and how are they respected or
not. There are people that work for me I
don't like. It doesn't matter. I respect
them. I respect their ability to
execute. And that above all is the most
important thing. If you start getting
into interpersonal relationships, you
will fail because you may have to fire
that person one day. People that hire
family take huge risk. Nepotism is a
horrible disease. It's it's uh some of
the greatest uh private companies on
earth never let the kids run them. They
just put them on the board and they hire
professional management. That's how they
keep wealth multigenerational.
Think about a tetropac for example.
People may not know that name but it's a
massive successful company. IKEA I mean
you know it's sort of you have to learn
those lessons. It's it's um
it's about respect
in both directions. It's not about
likability or softness or some social
met metric. It it really isn't. And
trying to redefine leadership that way
because it's on trend, it's not going to
work.
I started my first business at 12 years
old and I started more businesses at 14,
15, 16, 17, and 18. And at that time,
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What about finding the definition of the
word company is group of people. So in
terms of finding great people, is there
anything that you can offer to
entrepreneurs that are listening about
how you've done that and what you've
learned over time, the mistakes you've
made with assembling your group of
people.
Yeah. Hiring them without testing them
first. I've made that mistake.
So So you now test them first.
Just because someone says they can
execute doesn't mean they can. I mean
it's of course you're in an interview.
They're not going to say I can't
execute. You know, you're looking at
their past. You're saying this looks
terrific. Looks like you can fit in, but
it's on a piece of paper. They haven't
been road tested. They haven't been put
in a situation where they have to make
individual decisions that that have
consequence. The people you want are
able to make decisions that have
consequence. Good, bad, good
consequence, bad consequence. You don't
know yet. But they have to have be able
to make that decision on their own
without calling you up because you gave
them that mandate. Maybe you put a set
of parameter you could spend a million
bucks no more without calling me. But
whatever it is, I don't want to hear
from them. I just want the outcome.
What about resilience and hard work? How
much does that matter to you? Cuz I know
you said they can work when you know
they as long as they get the job done.
But are you trying to figure out if they
are a bit of a psychopath in terms of
hard work, if they're possessed,
obsessed?
I don't find the ones that are
psychopaths hard work are actually the
most successful. It's not the case. I
find the ones that are eclectic people
that have other pursuits that are
nothing to do with the business they're
in that
do crazy stuff. You know, maybe it's
riding motorcycles in the desert. I
don't know. You know, these are the
examples I'm just using because I'm
living with them.
And say, "Look, I've got to go and ride
a bicycle across the the desert." Okay.
How many days you going to be gone? I
don't know. Maybe three. Okay. Is there
anything that is immediate? That tells
me that
if you look at if you look at the years
outcome from that person, you're going
to find that they probably outperformed.
You you you want you want you want the
eclectic ones. You want the ones that
are not just robots working. It it's
going to be cheaper to get a robot if
you want a robot. I'm going to buy those
too when they come available. But I want
people that have creative
and
unusual solutions
that you know just think outside of the
box.
It's it's really interesting that way.
The other thing that um everybody wants
to hear from you about is how to keep
and grow your wealth because you know
making wealth. I kind of understand
through the lens of entrepreneurship,
take a big bet, um hopefully have an
exit or you know draw a dividend or make
profit from a company you've started.
But in terms of what you did and your
relationship with your money, what is
the most important things for someone to
understand who's just trying to grow
their money?
Yeah. Yeah. Know I learned this from my
mother and I actually built a whole
indexing company around it when I was
very young. I found out something uh
that um so she um was fiercely
independent. She's one of three
daughters uh of Lebanese descent. Myth's
father, my my father, my original
father, biological father was Irish.
She didn't Yeah, there she is. Geette.
So,
I haven't seen that picture in a while.
Okay.
She was very independent
and
she never ever wanted a man to control
her life. So she started at an early age
when she was working for her father.
They paid the girls. the family all
worked there and she worked in the
accounting department
and billing, but she got paid cash and
so she
would take 20%
of that cash each week and
she would put it into two asset classes.
Stocks that paid dividends, large cap
stocks and telco bonds.
7-year Telco bonds paid about 6 and a
half to 8% back then. She bought the
long bonds and she had that portfolio
for 55 years.
Wow.
Um she never spent any of the principal,
only the dividends and the interest. She
put my brother and I through college,
you know, she took care of her family
and her sisters when they fell on hard
times. But her rule is very simple. No
more than 5% in any one stock or bond of
the portfolio. and no more than 20% in
any one sector ever. Ever. So when a
stock ran up past five, she'd sell it
down. This is not genius. This is just
diversification.
And
when she passed and I I was the older
brother and I saw the portfolio cuz the
lawyer said, "Listen, you got to come
down here. You're the executive of
Will." And I said, "Yeah, but you know,
my mother was middle class."
He said, "No, you got to come down
here." um she kept her account secret
from both of her husbands. She wanted
her own independent money and back then
you could do that
and um damn I mean what that portfolio
did the performance was extraordinary.
It was beyond any hedge fund guy or
anything 55 years.
When I saw the results I said that's it.
That's how I'm going to invest for the
rest of my life. Exactly the way Geette
did. No more than 5%
in any one stock ever. No ma no matter
what it is and no more than 20% in any
one sector with the exception of real
estate which is a very large part of
what I have in net worth and I it's a
it's a third. So that's broken the rule
but there's reasons for that and I'm
very happy with that portfolio. But um
that if she if if everybody that's
listening to this does that they will
maintain and grow their wealth. But it's
people bet. They make big bets. They
just they think they're so damn right.
They put half their net worth into one
sector or one stock and they get wiped
out. That's what happens.
So would your mother pick the stocks
herself or would she invest in an index
fund or
she indexed?
She used Okay. So you can even back then
you know they didn't have ETFs but they
had mutual funds that said their own the
only stock in this mutual fund is it
doesn't have any debt and it pays
dividends you know whatever they were
very rudimentary back then they were
just collections of stocks I think she
had like
28 names or something like that in the
portfolio but if you looked at them they
were really boring large cap names but
they were sectorally diverse there
wasn't 10 sectors back then there was
only there there There wasn't 11, there
was 10. So, they didn't have real estate
as a sector. So, but you know, I looked
at it saying, "Wow, at least they're
really boring."
You learned a lot about money from your
early upbringing, right? From your that
early context.
Yeah. Because what she said to me was,
"Look,
you know, I I even do this today with
wealthy people call me up all the time
and say, "Look, um,
you know, they get divorced. this really
this a very wealthy woman got divorced
recently and she said look I you know
divorcing and she was a billionaire she
was divorcing she was more
multi-billionaire and so she said look I
I'm getting everybody's calling me up um
to be my advisor because I'm separating
from my husband it's all his guys that
did all the management of our family
wealth would you be my adviser I said no
I don't do that um but you know I can I
can just give you some basic advice and
you and hire people that stick on the
mandate. And I gave her Georgette
strategy, but she I I had her do
something else, too. I said, "Let's get
a piece of paper. You're a billionaire.
Let's put everything on this piece of
paper on the last 90 days that you've
spent on whatever the hell it is. I
don't care. And let's put on no
computer, no spreadsheet on this. Let's
look at all the income that you've made
off your portfolio as it stands now,
whether it's gold you have or land or
stocks or bonds.
Let's just do a a gut check on do you
outspend yourself.
She said, "Why would I give a shit?" I
said, "Wouldn't you like to know how
much money you're burning living your
lifestyle the way you live it just out
of interest? Maybe you have enough for
the rest of your life, but maybe you
want to give some of it to your family
one day or give it to charity. Wouldn't
you like to know?" Because one of my
rules is never outspend yourself on any
30 or 60 day cycle ever.
Just ever. I don't have any debt. So, so
I'm very careful about that. And we went
through this little thing.
She freaked out. She was pissing away
money. Just bleeding
hundreds of thousands of dollars a week.
I mean, I don't care how rich you are,
you don't want to be stupid. And I said,
"Does that shock you? One of two things
has to happen. I mean, you're you're
losing millions of dollars a quarter.
Like,
why? Why? Like you don't you you've had
nobody restrict what you do with your
money because you're going to have to
sell stocks at some point or sell gold
or sell land to keep this up and are you
really that happy? Like what do you
what's all this [ __ ] you're buying? Like
what is all this crap that you don't
need? It was a eye openener for her. So
I'm my point is most people don't do
that exercise. I don't care if you're
only making 56,000 a year or 68 the
average salary.
So, are you in the camp that you
shouldn't spend money on the small
things like the coffee? If you don't
need it, you should make the coffee at
home. Is that kind of
I I just I can't stand it when I see
kids that are making 70 grand a year
spending $28 for lunch. I mean, that's
just stupid. It's just think about that
in the context of that being put into an
index and making 8 to 8 to 10% a year
for the next 50 years.
What's an index for someone that doesn't
So, okay. I mean, you know, I even have
it. I even built an app for this purpose
just so I could There's many apps out
there. You don't have to use mine.
Mine's called Bean Stocks, but you just
allocate 15% of your salary and it
automatically puts it into two buckets.
Some stocks and some bonds. The stocks
are ETFs, exchange traded funds that
just track the S&P 500. Very simply,
mine's a little
The S&P 500 is the top 500 stocks.
Yeah. So, it's just, you know, people
tell me, "Oh, I can beat the S&P. I can
pick stocks." They're so full of crap.
not over the long period they can. So,
it's better you might as well just own
ETFs. I have a version of the S&P that I
designed with other people that strips
out all the crappy balance sheets. But
that's just me. You can just buy the
index that you want. You know, the ETF
and then you pay low fees and then over
time it appreciates and then if you buy
some treasury bills or what fixed income
you get that you should have less of
those when you're young and more of them
when you're older. That's just
diversification. But you you know the
best test I do with my kids' friends
too. Go into a closet. Go into your
closet and look at how much [ __ ] you
have you don't wear because you either
bought it because you thought you were
going to wear it and never wore it or
wore it once and you end up wearing 20%
of your portfolio all of the time and
80% you you pissed away. I mean that's
really stupid. And so for a young
person, a young woman or man, don't do
that. Start putting and just buy the
minimum stuff. And another thing I
learned from my mother, this is
interesting because I saw it happen at
her death. She,
you know, would buy two Chanel jackets a
year, really expensive Chanel jackets,
handmade Chanel jackets. I do business
with Chanel because of, you know, the
legacy of my mother and the whole Coco
Chanel thing and watches. I love those
guys. And
her theory was this will never get old.
And it never did. A classic vintage
Chanel jacket from the 50s that's
well-kept
is worth a fortune today. The classic,
it still wears beautifully. They're so
well made. So, she wouldn't buy crap.
She'd buy really good stuff, but a
little just small amounts of it. And
over the years, she'd built up this
portfolio of amazing clothing. And when
she died, the women in in our family had
a cat fight over her portfolio.
Unbelievable.
Is that in part why you have so many
watches? I've noticed you have a watch
on either wrist right now.
Yeah, I'm pretty big in watches. I mean,
but but watches to me, every piece I
have marks something in my life that was
important. A deal, a child, graduation,
um, you know, something. Every piece.
I've got a lot of watches.
How many have you got?
I I don't even say anymore because of
the insurance policy I have. I got a
lot.
Do you invest in You're talking about
your your mother's investing strategy,
and one of the things you said is she
invested in dividend stocks.
Yes. What is a dividend stock and should
I be investing in dividend stocks?
Yeah, I mean, you know, a company if
it's profitable and it's operating, it
business plan is working and it's
growing market share at some point says,
"I'm going to distribute some of the
success of our profits to our
shareholders." That's a dividend. And so
they send that cash to you and you can
either redeploy it in other ways or live
off it or whatever. Many tech stocks
until recently did not pay dividends.
But now the behemoth tech stocks do pay
dividends because the demand of an aging
population is I need to eat and so I
like to own the stock for growth but I
also want to get some of the profits and
so dividend paying stocks uh used to be
utilities uh but not so today. Every
every sector has dividend paying stocks.
So I prefer to own dividend paying
stocks div payers and then I also own
fixed income products. I also own crypto
now and I own alternative assets like
gold and watches. My watch collection's
actually done quite well even though
there's been a correction. There's
volatility, but I have some watches that
have, you know, I bought for
200,000 that are worth over a million
today.
Crypto. So, are you still bullish on
crypto as an investment?
Yeah, I am actually, but people get
crypto confused with its real potential.
Um,
uh, let's talk about digital payment
systems because what's about to pass
first, we're days away from this
happening, is the Genius Act, which is
actually the Stablecoin Act. It was just
passed by the Senate 48 hours ago. It's
going back to the House. I I actually
worked on that bill two years ago. So,
if that bill passes, it's really nothing
to do with speculating on crypto. It's a
new form of payment. So, if I wanted to
order a watch in uh from Simone Brit,
who's somebody I buy watches from. He's
a master watch maker. Right now, I have
to take US dollars, I've got to get
through a know your client um
prerogative. Um I'm treated like a
criminal by transferring $100,000 over.
Turn it into Swiss Franks. Takes about a
week. I get screwed for about 200 basis
points in the whole thing. If I if he
accepted USDC, which is actually a
stable coin back with the US dollar,
just went public, very successful IPO. I
was a shareholder in that company, too.
That's one of my best IPOs in the last
two years. The transaction would happen
in less than a second and the fees would
be at hundth of what the costs are right
now. So it's a digital payment system.
The price doesn't it's not it's no
speculation on it's backed by the US
dollar treasury bills. So it's sort of a
new form of of digital payment. That's
different than Bitcoin which is a
speculation. It's if you believe in
Bitcoin, you think it's a digital gold
and you live through the volatility. I
believe in both. I believe that that
crypto will be the 12th sector of the
S&P in some period of time because it
provides productivity to all 11 other
sectors. So the way I own it is I own
the exchanges. My exchange in one called
Wonderfy up in Canada just got acquired
last week or two weeks ago by Robin
Hood. I'm happy because I think Vlad who
runs Robin Hood's great and now he's got
a million plus accounts in Canada and
market that he never participated in.
But the point is this is never going
away. It's going to stay forever. So how
do you participate? You can buy some
Bitcoin just like you can buy gold, buy
it in an ETF or actually own it
yourself. You can buy the exchanges. You
can use um you know you can buy Circle
stock now it's public. You can Circle
makes USDC. you can buy USDC in in an
account and make 4.1% interest on it
right now. So, there's a lot of ways to
participate, but yes, I'm here to stay,
but I've g I've grown up. I was around
during the period where the crypto
cowboys lived and and I survived that
all and I even testified in front of the
Senate and the House and whatever else
the testimonies were during the the
tumultuous period and most of those guys
went to jail.
Your portfolio in terms of Bitcoin
allocation or crypto allocation, what is
it now?
It's at about allin. Uh we we marked to
market last month it was 19.1%.
19.1%.
Yeah. We have to keep it under 20. It's
a sector. So but remember in that is the
cryptos itself, Bitcoin, the USDC and
the shares of the infrastructure
companies like Circle and everything
else. I've got you know it was a very
successful IPO. One of the first things
most people do when they get a bit of
money, usually from their their job, is
they get a mortgage on a house because
we're kind of taught as we grow up that
the best way to make or the the not
maybe the best, but the most obvious way
to create wealth is to buy your first
home.
Yeah, there's a very basic rule for that
and I understand it and I did the same
thing. But what I made sure again from
my mother was never let the mortgage and
the cost of maintaining the house be
more than onethird
of your income. Onethird of your income.
If it's more than onethird, you bought
too much house. So it's better to buy a
house that's maybe it's only going to be
1,900 square feet to start in a
neighborhood that you may not want to
stay for the rest of your life, but
start to acrue the benefit of real
estate from that point of view. Learn
how to manage it. Maybe you rent part of
it out or whatever, but it can't be more
than a third of your income. The mistake
that people made, and they're starting
to suffer from it now, is when money was
so cheap, mortgage mortgage rates were
under 4%, they were 3.2% some of them,
they bought massive houses. And now
they're running into having to refinance
those houses at much higher rates, more
than 7%. And it's becoming 60, 70, 80%
of their income. They're screwed. They
bought too much house. So, it's about
making sure that you can manage that.
And also you want some diversification.
Yes, a mortgage is okay, particular if
you're having a family because you're
going to pay rent or you're gonna pay a
mortgage, one of the two. But you want
some diversification in starting to
build up that investment account for
when you retire so that you have
something to live off. If you only put
aside 15% if you're you're making 70,000
a year and you put 15% aside from when
you're 25, you'll have over a million
and a half dollars if you just invested
it in the stock index in the S&P 500.
That's what that's what history has told
you.
In what time frame?
Your whole career. I mean, you're going
to be 65, you're 25, 65. You just stick
with that protocol and you'll watch it
grow. You'll watch it grow. You go up
and down as the market goes up and down.
Some years it'll go flat, whatever. But
it's the people that don't even think
ahead and find themselves at 45 mired in
debt, including a mortgage. You want to
get rid of your mortgage in your 40s.
Most people's primary investment asset
is the house they buy.
Is that
Yes, it is. But it's also the debt they
own. It's a primary asset. How much debt
does it have on it? It's only the equity
value is the asset. So, if you're buying
a house that's too big and it's you've
only put down 10% and it's 90% mortgage,
what do you really own? you really own
the 10%
at whatever price it is. Sometimes
housing goes flat for a while. It's it's
okay, but it's not okay if it's too much
house.
If you're a 25year-old and you're on
that 70k that you talked about, and your
objective was to make money, you don't
have kids, you don't you're not in a
relationship,
would you buy a house?
No. No, I wouldn't because why do I need
a house if I'm only unless I'm renting
as an income property? I'm buying a
house because I'm getting married. I'm
going to raise a family. I need a house.
I mean,
is that the the use case for buying a
house? You think?
I think it is. People, but it's not.
There are many people that say, "I love
real estate. I'm going to buy three
houses. I'm going to rent them out."
That's a different business. And I know
people in their 20s that do that. In
fact, they're successful. That's all
they do. And so, that their job is to
find houses, buy them, fix them up, and
rent them. And they manage that
geographically tight portfolio. It
happens a lot in student housing. for
example, got a good friend who's
involved in student housing. He's very
successful. He just focuses on one
aspect, buildings that rent to students
and he manages it and he, you know,
raises a family. He's successful, but
that's one thing he does. That's not the
same as saying, "I'm going to buy a
house cuz I'm I just got married and I'm
going to raise I'm going to have a child
in the next 24 months." Then you should
have a house. But if you're you said to
me, "I'm single. I want to make money."
I wouldn't buy a house. That's not the
number one asset class. I think I'd get
a diversified portfolio and just ride
the pony with that for a while until I
meet that special person I'm going to,
you know, raise a family with and then I
have a little nest egg I can work with.
I mean,
wealth creation
comes down to one word, discipline.
That's it. The ability to look at
something and say, "I'm not going to buy
that. I'm going to keep that money
working for me." Not many people have
that discipline.
Wealthy people have that discipline. You
meet them later in life, you realize
when they were young and had nothing,
even the ones that were employees their
whole lives that are now financially
free had the discipline to say no.
There's so much stuff you don't need.
And you should never buy a watch unless
you can afford it. Ever go on debt for a
watch because people hear this stuff
say, "I'm going to buy watches like with
red bands." No, you're not. That's why I
wear watches now that cost under $500 to
show kids you want to get into herology.
You don't have to spend, you know,
$50,000. Here's a here's a Timex for
$265. It looks beautiful. Get that.
You said, uh, you know, don't buy the
house until you meet your partner, etc.
How much does the person that you fall
in love with have an impact on your
finances, your money, your chance of
success in your view?
It's everything. Are you kidding? I
mean, it's it's everything. If you read
I mean, think about this.
You you need to find somebody if you're
an entrepreneur. So that's for the we're
talking about the third now that want to
go on the rocket ship ride. You better
find somebody that's willing to tolerate
the fact that you're never home for the
first 10 years. They're going to raise a
family by themselves because there's no
balance in life. That that idea of
balance is complete [ __ ] I mean,
it's just [ __ ] You have to work so
hard to compete globally these days in
every sector. you're going to work your
ass off and it's not going to happen
over I mean Anna Sky did it in three
years but she had worked much harder
previously it was not her first deal but
she was just lucky I mean she
was this the cat DNA
cat thing I mean she's she she but she's
you know she's she's working again she's
back she wants to work I mean that's
what happens you never stop working but
the thing is
that partnership
and this is what people don't get about
marriage
marriage Marriage is a business. I know
people go nuts when I say that, but it's
a business. And the first child you're
going to have is money. It's going to be
the first child, and it's going to sit
at the table with you every day. It's
it's there sitting there. If you don't
have money, you don't have a marriage. I
mean, the reason people get married is
to form a form of financial stability so
that they can afford a family. And you
have to figure out,
you know, I'm I'm I've been with my wife
a long time and we've been separated for
a couple of years, but you know, family
is very important to me. So, I we got
back together again. We you know, our
daughter got us back together. I'm very
happy we did it. But it's
we make financial decisions together. We
we always check in, you know, anything
that's material,
you know, if we're going to do a
renovation or something. And and I
respect her for that. I have a lot of
respect for her because she doesn't just
spend money. We didn't have any money
when we started. We had nothing. And so
that's why a great marriage can work
because you build it together. You
really care about it. You care about
your family. You also care about what
you you've created in wealth. And I
consider my money her money. You like
because she was the family that let me
go and do this stuff. Now I don't have
the same relationship with our kids that
she does because she raised them. But
that's the thing you give up and you
have to give something up. That's it.
You can be a great father, a great
provider, but you're never going to have
the closest that she had reading them
stories when they were young. I wasn't
there. But, you know, the outcome has
been good. I think everybody looks at
that and says, "All right, that's
great."
But my mother never believed in
entitlement. And so, I don't believe in
it either. I'm not gifting my kids a ton
of money. You know, I I want them to
launch, and they've done that
successfully. They got to they got to
work. You know, they got to do their
thing. I've heard you say before that
the most important financial decision
you'll ever make is who you'll marry.
Yes.
Why?
Because think of the geometric loss of
wealth. Every time you get divorced,
you pay the woman that you divorced or
man and you pay the government
a third often through capital gains and
liquidation because you can't separate
all the assets without liquidating them
sometimes. So, you've got the government
sitting there. You've got the other
spouse sitting there. This is the
stupidest thing you can ever do. It took
your whole life to
to actually create this nest egg.
Could be, you know, you're 45 or
whatever. You you've got a comfortable
life and all of a sudden you don't like
your wife or husband. Think about that
for a while because you are going to
wipe out up to twothirds of your wealth.
You better really like somebody else a
lot. And frankly,
sometimes it's not the other person that
you're divorcing. It's you. You're the
problem. If you're getting married for
the third time, you're a guy or woman.
It's not them. It's you. There's
something wrong with you. And you should
probably not get into another economic
union. You should probably just date
till you drop dead because it's stupid.
Marriages are tough. I mean, they're
tough. Anybody who's been married for
more than 20 years knows exactly what
I'm talking about. But they have they
acrew more benefit than than you know
anything. So if as long if you're happy
51% of the day with your wife, stay with
him or her husband or wife. You that's
very important. How often do you think
divorces are a result of money issues?
Well, you may be shocked at this. I
wrote a book um about this and I decided
uh men and women of money a long time
ago, 10 years plus. Right there it is.
And I did some research and I I uh went
to meet some of the top um divorce
lawyers in North America, in New York,
in Boston, and other cities.
And I said, "Look, I I want to kind of
do a pie chart of reasons for divorce
that seemed 50% seem to end divorce
within 5 to seven years."
Every one of them, they didn't know each
other, said, "It's not infidelity.
Nothing to do with it. Most marriages
can u survive infidelity.
they can't survive financial stress.
And so what happens invariably is you
fall in love, but you didn't do any due
diligence on that person's spending
habits or their financial history
because La More is so wonderful in the
early days. You didn't do any diligence
on their family or them or their brother
or bankruptcy in the past or whatever it
is. And then you get married and you
know the euphoria starts to wear off and
you notice that the other is outspending
you
just buying a lot of stuff
beyond your means.
And that starts the first friction. And
then that credit card comes in with
$100,000 on it at 23% interest and
another
purse was bought or whatever the hell it
is.
and you're you're starting to sink
because you may have married somebody
who can't stop spending. This is just a
typical
there are people that can't have no
discipline. They just can't. They got to
have the boat. They got to have this.
They got to have that. And they pressure
their other to say, "Look, I want to
keep up with the Joneses next door, even
though they may only each have a salary
of 100 grand each. Can't do it." And
they have kids and they're trying to put
them through college.
That's divorce. That's why almost 90% of
of unions break up is is is that classic
financial pressure and divorce gets them
out of that mess because they can no
longer spend on your credit card
anymore. But it's a horrible way to go.
So I, you know, I'm an investor in a
company called Hello Prenup that does
divorces for does um uh prenups for
women and prenups forced during the
euphoric period diligence.
It's that simple. You're going to find
out if that person has a financial
problem going into the marriage. They
have to disclose
their financial background.
So, you talk about these five love
languages of money. The mooch, someone
who won't pay for anything,
right?
Should I date someone like that?
It's a warning signal. It's a problem.
It's a problem. So,
or they don't really want you for
companionship. They just want you for
financial support.
The spender holic. Someone who always
offers to pay for everything to appear
popular and successful.
Bad morning sign. Huge. I mean that
isn't that is insecurity measurable by
cash outlay.
The loafer. Someone who has no ambition
and drive for money.
A void with extreme prejudice.
The thief. Someone who steals.
You can have no tolerance for that.
And the meanie. A balanced spender who
lives within their means.
Love that. Marry a meanie. That's it.
That's That's the Those are the
marriages that last an entire life.
That's it. That's what you're looking
for. That's great advice right there.
Whatever the book costs, that's that's
the best value right there. And then ask
yourself, am I dating one of these or
not? You know, you know, you should talk
about money on the third date. Think
about a date. Think about dating. First
date, oh my goodness, this is a really
interesting person. Um or not, then
there's never a second date. second
date. I want to learn more. I'm really
interested. You're going into a third
date. There's something going on.
There's something going on. You both
want to meet again. That's the first
time you should say, "Look, I know this
is crazy, but we're here together a
third time because something's going on
here, and I'm just wondering what are
your long-term goals? I mean, it's not
about our marriage or anything else
other than we're having a great time,
but what are your ambitions? I'm really
interested in you. I'd like to know what
you think. And the maybe the woman says
or the guy says, "What are you checking
me out?" You say, "Yeah, yeah, I'm
really interested in you." It's a form
of finding out if the connection, you
know, I I should be a marriage
counselor. That's what I think. I mean,
it's it's really dating is is the is the
dance, but it should involve exploring
where we're going financially.
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just.com.
One of the big uh protagonists in the
story of many things we've discussed,
money, investing, building businesses
now is this thing called artificial
intelligence which you mentioned
earlier. Yes.
It's like entered the room.
Yes.
And it's changing lots of these
equations in a really profound way.
Again, for that person who is maybe at
the start of their career or even, you
know, they're they're a lawyer right
now.
How are you thinking about AI? What
should they be thinking about? Because I
don't think we've seen something quite
like this. Not certainly not in my
lifetime. I've not seen disruption of
this scale. I wasn't around for the com
boom. I was too when I was 10 or
something. I was eight.
Yeah.
So, so how should we be thinking about
this moment? Is it a huge opportunity
for wealth creation or
Yeah, it's immense. It's bigger than the
internet. And I'll tell you why. I want
to keep it down to earth. Uh because um
I'm actually using it now in use cases.
There's every sector of the economy,
every aspect of research, every aspect
of business has a huge opportunity here.
But let's just take use cases that you
would understand, everybody listening
would understand.
In today's post pandemic world,
most businesses have developed large and
small direct to consumer strategies
where they try and build relationships
with customers and sell them product
direct. Yeah, they still use retail. Say
you're Nike or something. And um you you
were 27% uh you know direct to consumer
before the pandemic. You're now 50%. And
direct to consumer gets you higher
margins, but it also gets you data. Gets
you information about the preferences of
your customer base. What they like, what
they don't like, the flavors, and what
they buy, when they buy, where they buy
it, all that stuff. And it's very
interesting that data. And let me give
you an example. Wine business. If you
think about
the wine business, the challenge of a
thousand-y old business, you don't know
what the weather's going to be like. you
don't know what varietals to to to grow
because you don't know what the
preference of the customer is because
you're selling it through multiple tiers
of distribution. During the pandemic, 43
states in America opened up direct to
consumer sales from the wineries in the
West Coast. For the first time ever, the
wineries found out, what people buy,
where they buy it, when they buy it,
what they drink, what varietals. And I'm
in the wine business. I sell three
million bottles a year of wine. One of
my companies, actually, a Shark Tank
company. Um, and we partner with a
company called uh QVC. We sell online
and and so I can tell you today,
this month, this week, the number one
varietal in Southern Florida for women
ages 44 to 64 is Mosscato, a sweet wine.
I think it tastes like [ __ ] I don't
care what I think. It's the number one
wine right now. And I knew that to to
make that varietal available six months
ago so that I would be able to ship it
and put the inventory, the capex in the
right place at the right time to support
that demand for the rest of this summer.
A sweet cold Mosscato wine. That means I
spent a lot less money, a lot less risk.
I don't have any varietals they don't
want this summer. I have exactly what
they want. That was AI.
It cost me virtually nothing to get that
data. Five, 10 years ago, it would have
cost me a million bucks to go do all the
market research. I got that for $18,000.
So that's using an AI tool. Here's
another example. So do I use that tool?
100%. And there's many tools. You don't
have to just use chat. There's many
different competing platforms. So we use
them all. We check the assumptions by
checking it all on all of them. See the
little variances. Number two, I have to
shoot an ad. I have to shoot a
commercial.
I'm going to shoot it here in LA. I'm
going to do it in a studio like this
with a green screen. And um I'm going to
spend, you know, $250,000 for a 30, you
know, 15, a 30, and a 60 out of the same
shoot. And I'm then going to go into
post with the green screen and I'm going
to spend more money in post. I'm going
to add whatever I need, whatever
background I'm going to need. Or I could
fly to Dubai
where they have a giant studio with a 6K
digital wall
where AI links up your script
to the background. There is no
post-prouction. You basically shoot the
commercial
in 4 hours and it's done. The
background's perfect. The imagery is
perfect. Your script is perfect. And I
did that two weeks ago for the first
time. I'd never seen that before. We did
it for a fraction of the cost of what it
would have cost to do it in the old way
in post-prouction. But then I'll tell
you what freaked me out.
They reshot the commercial without me
there using Kevin agent
an AI view.
I wasn't even there. and just to show
that they could produce a new commercial
with the same background
for $9,000
that would have cost 400,000 from
scratch. So there's going to be a lot of
job disruption then because as you said
you don't say but on the other hand I've
now got content for that particular
business I was shooting that you know
I've got content for that particular
business I was going to shoot that
commercial for and I said guys
let's tweak it and shoot it again. He
said yeah we'll do it in two seconds.
We'll send you the the 15 seconds back.
I said I I I don't like what I said
there. Can I change what I said? Yeah.
Well do you want it in Spanish? You want
it in Japanese? You want it in Arabic?
That's the power. The productivity that
we're going to get, we're going to our
budgets for producing content are going
to drop dramatically over the next
and software and everything else, right?
Creating everything is going to get
Now, full circle to your your thing
about the chips that all came from
Nvidia chips
that not that's not from Chinese chips.
Whoever controls the chip and the
honeybees that the honey bees are those
guys are all Indians and Pakistanis.
They're genius mathematicians. That's
the team over there running off that
platform. If we had let anyways I don't
want to I'm just freaked out that we got
to control that. We we need democracy to
control that.
Your children, what are you saying to
them though about their professional
ambitions in a world where creating
stuff like that and you know whether
it's who do you want to do your your
taxes an accountant or an AI? Who do you
want to do your legal documents? Who do
you want to do your any sort of like
white collar job your make your videos
edit your videos? I I tell them, you
know, everybody's got a lot of angst
with AI. I I tell them, listen,
everybody chillax. It's a tool. You
know, it's the same classic thing where
radio was going to be displaced by
television. Radio's bigger than it ever
has been. It it just it doesn't matter.
The one thing I concern myself with with
AI is warfare. And I think the country
that has the best AI and data centers
and the most advanced chip technology
will win the wars of the future, which
will be fought by drones and robots. I
know that sounds kind of crazy.
No, it doesn't sound crazy. That's where
it's happening now.
That's where it's going to go. So, so
when I when I solicit the ear of a
senator, I try and explain to them my
honeybee analogy saying this is about
defense. I don't want to live under
authoritarian. You know, I know we
debate the whole political environment
these days, but I don't want to live
around Chinese honey. I just don't. And
those are going to be the two
superpowers. You both you're in one
vertical. Either you let the Chinese
make the honey on AI or we make the
honey and let the Chinese buy some honey
from us. I know where I want to live. I
know what I want to do. And I think I
can convince a lot of senators the same
idea because you got to understand the
Wnjak jobs analogy that we that you
brought out earlier. That was the genius
of jobs. Make the honey but know who the
queen bee is.
The genius of jobs brings me to a
question I've wanted to ask someone like
you for a long long time which is do you
think Apple is dead?
No. No you don't.
No. I'll tell you why. I'll tell you
why. You know it's so interesting. uh
people don't understand the genius of
Apple because this is again came from
Jobs you know he used to say to my team
over and over again and I mentioned it
earlier they don't know what they want
until I tell them
and I always just just as close as you
and I are right now you're Steve
say Steve
how the [ __ ] do you know that how do you
know that you don't know that you don't
know what you don't No. He said, "Show
me where I'm wrong. Show me one instance
of us working together. I'm wrong." I
said, "It hasn't happened yet, Steve.
Doesn't mean it won't.
Get back to work. Don't worry about it.
I'll worry about it. You make the
software. I have the chips. Make the
software. Go make the honey. I have the
queen bee. Don't worry about it." And
that
is pretty interesting because you got to
prove it that he was wrong. Let's take
let's accelerate. He's dead now. But the
philosophy of Apple and I'll give you
the the way you win at you look at it. I
can go buy a $330 laptop right here
with the same processing power of this
$1,800 Mac laptop.
Why would I been spend 1,800 when I
could buy this for 300? Why brand? I
want to be part of this universe.
This honey right over here, the Apple
Care, the fact that the OS works on all
the platforms and the messages are shown
on all platforms simultaneously. All the
OS, all the honey,
that platform is the power of brand.
It's I'm not leaving this universe and
Apple is one of the world's largest
companies. And you may say, "Oh, an
innovation is going to make everybody
leave that platform." I don't think so.
They let other people sometimes bring in
a new market and then they take it over.
And I saw Steve do that multiple times.
He did it um with the phone. I was
around for that. That was crazy. I mean,
he had the vision that we would someday
run our software on the phone. I said,
"You're out of your mind. The screen's
too small." He said, "No,
you're going to go vertical. You're
going to rewrite all this crap
vertically."
I mean, I can't fault him on anything.
Although I kept telling him, "You're
going to get it wrong one day. You're
not going to be right all the time." I
can't find when he wasn't right. That
that's that's the frustration because I
teach this you know to a har bunch of
really smart kids at Harvard of which by
the way a third are international
students and
they say well when did you catch him? I
said he didn't
what was he doing was did he have a
practice or or principles that allowed
him to see around the corner? He spent a
lot of time at night um
you know
even studying fonts and looking at art
and um focusing on the signal. I think
his wife talked about that a lot. He I
mean she spent more time with him than
anybody else. Although W talks about a
lot because those guys spent countless
hours together and
but but
Jobs defined
he would take
instances from nature
into his head or from Japanese,
you know, scripture or text or imagery
and redefine it into technology in a way
that no one else was doing. And that's
the idea of the honey and the bee and
the queen and all that stuff. It kind of
comes from his view of the world. And I
don't know if you can understand this,
but because it was so
it came from nature, it was easy for
people to assimilate it. It wasn't
foreign. When they looked at the imagery
and the design, he he tried to pull from
from pleasing images from nature like
the fonts on the first Max. I remember
when we were writing the code for that
saying, "Steve, this is not what people
are used to seeing on a computer
screen." He said, "No, it isn't. That's
why it's going to work." He, if you
think about the very first scalable
fonts,
I saw that first. And I said, "See, this
is this is almost foreign." He said,
"Well, how's it make you feel?" I said,
"Makes me feel pretty good. This looks
like it's on a piece of paper. If you I
don't you weren't even born when this
stuff was happening but it was it he was
so far ahead
and this is the same way Elon is
redefining whether it's you know SpaceX
or whether it's what he's doing in
neurosurgery or Tesla or you know all of
these initiatives uh you know his
satellite technologies they are the same
those guys except you know Elon's 100%
signal I said that earlier they are the
same and they should be their treasures,
their national treasures. It doesn't
matter if you like them. It doesn't
matter what their politics are is
irrelevant the contributions they're
making to society and to America,
frankly, and the competitive competitive
nature of of of countries. That's why I
thought it was so important that Trump
make up with Elon. The the most powerful
man on earth should have a a very good
relationship with the most the richest
man on earth because he's the largest
industrialist on earth. Maybe there's
like an inherent inability by way of
them being who you just said they are
the most powerful.
But they know they're smart enough to
know. It's the same way I felt about
Jobs. I'm getting back on the plane this
quarter. I know he's going to beat me
up, but it doesn't matter. It It's the
greater good is that we get this
software out there advancing ma math and
reading scores.
Was he happy, Steve?
I don't know the answer to that
question.
Do you think he was a happy person?
I don't know. He I've never I never saw
him happy. He was always barking at me.
I never saw him happy. I don't think I
ever saw him laugh.
I don't He may not have been, you know,
that I mean that's probably something
his wife would know, but he looked like
a tortured guy to me, but um
you know that may have been his curse. I
you know some some you
do you love him?
Yeah,
I can see it in your face
100%. I saw a lot of emotion in your
face the first time you spoke about him
and I thought that's surprising for
someone that barked at you.
Well, he respected me, that's for sure.
He wouldn't execute on my ideas. He
expected me to execute on his, but he
was never wrong.
Where did the emotions stem from?
Oh, you know, it brings me back into
that room with Heidi Rosen and all the
crazy crap. I mean, it was just nuts.
And you know, the you know, I'd have to
spend a lot of time. The only the only
meeting I really remember um the the one
that's really sticks in my mind when we
were in Certino and we were just I think
I don't know we were going after him for
18 million or something and Heidi was
there.
Who's Heidi? Heidi Rosen. Um, she's a
famous um, venture capitalist, but she
was also kind of the muse, the person
that could actually deal with Jobs all
day long at Apple and bring him back to
Earth when he was out of his mind. I'll
give you an example of how that would
work. And I've seen her since, you know,
it's it's it's I don't even know if she
remembers this particular. Anyways, we
leave. He's barking at me. He's and he's
got one of my product managers in tears
because she wanted to do the market
research and he said, "No way. I we're
just going to do what I say." And she
just felt like her job was useless. And
and for him it was. I mean, he just
didn't give a [ __ ] what she thought.
Although she ran the universe of the
Oregon Trail or something. It's a
massive title, like a huge multi-million
dollar title on the Mac in every 110,000
schools in America.
And he he was so pissed that you know in
these old buildings they have the little
window where you have a little knob and
it only opens up four inches so you
can't jump out of it in a hotel or
something. So we were we had a Herz
rental and we're the whole team's going
out. I'm going to drive the car back to
San Francisco. I'm going to fly back to
Boston and he he undoes the window and
he's got his head stuck and there's
yelling at me from from
I'm looking up at him saying, you know,
what the [ __ ] Like what? Like what what
more can we we you already kicked us
out, you know? And then on the way, we
had these old brick the earliest cell
phones, these brick phones. Heidi calls
me, says, "Okay, he'll do it for 12
million." I said, "Heidi, why do we have
to go through all that [ __ ] Like, why
do we even have to get abused?" She
said, "Why is the sky blue?" you know,
just get back on the plane and go do it.
It was a huge hit. Like it just, you
know, it's a huge hit. Like it's just
the guy was if you looked at it like uh
he he he could he could write the hit
songs. That's what he did. He write the
hit songs. So you don't even if you hate
the producer, you want the the guy that
can do the hit songs, right? If you're
an artist, you put up with a crazy
producer.
Could he not have been nice? Do you
think?
Not in his DNA.
No. Do you think if he he was a nice
person he wouldn't
you know what he would say about that
that's noise
he gives a [ __ ]
yeah he doesn't give a [ __ ] noise being
nice is noise that for him I mean we
spent a lot of time talking about him
but I think there's a lot of lessons
learned from him that I think managers
today parents today certainly CEOs today
uh you know you're you're about this
show is about CEOs um
I wish every CEO had spent the time the
minimal time that I spent with jobs had
such an impact on me. I mean, it it I I
I owe a lot of my success to him because
I think I always think, what would Steve
have done?
And I make decisions like that. It's
amazing. The guy's still around. I bet
you if you talk to, you know, any of the
management at Apple, they they have that
ghost in those rooms for sure,
including the current CEO who I think
was doing a phenomenal job. He he spent
so many hours with Jobs. He knows
exactly what I'm talking about.
Nobody spent more time in business than
that guy for sure.
I asked you a second ago if Steve Jobs
was happy, but are you happy?
I get happier the older I get because um
I've I'm very comfortable. I found a
place um you know uh that I'm and I this
may be just what aging does. I mean, it
just, you know, in and when I was in my
30s, I had a lot of trauma and turmoil
and and just, you know, um hard time to
find trying to figure out who I was. And
I also suffered from dyslexia, which
I've come to think of as a superpower
now, not an affliction, but it it was
kind of like it's hard to know what
journey you're going to be on until you
find it. And then I found it, and then I
started on a new journey. and and
you know it's um
it's something where you know you ask
yourself every day goes by and you know
this the noise and signal thing and how
much of this day was I happy doing the
things that I wanted to do and I am very
happy if if I measure it by
is there anything that I spend my time
doing that I don't want to do today the
answer is no because I don't have do and
so I don't waste my time. I do, you
know, even coming here to spend two
hours with you. When I first, you know,
heard about it, I went online and said,
"Oh, yeah. This guy, this guy's great.
I'd love to work with him." You know,
that kind of thing.
You you allocate your time. This is this
is I'm happy to do this. I want to be
here. And I think, you know, we had a
very interesting couple hours together.
But that's the definition of happiness.
What concerns me, and my wife often says
to me, "We don't need any more money.
Why are why are you flying 300 hours a
year on an airplane? What are you
doing?"
I said, "I'm happy." Like,
you know, I'm I'm happy doing this. I
want to do this stuff. You know, I
sometimes I do five cities in a day.
It's freaking crazy. And it's the
wonderful thing about, you know, air
travel today. You can do that. But it's
it's sport for you. It's it's it's so
interesting. I get so many interesting
opportunities. I can't turn them down.
They're just such,
you know.
Are you driven or are you dragged? You
know, you use the word trauma there. And
I often ask myself that question because
I I came from a all-white area. I was
the black kid with the strange hair and
the strange family. I was insecure. And
I think that resulted in this this force
of will to try and correct the
insecurity or to prove something to
myself which then resulted in success. I
I think there is no drag. There's only
driven. I don't understand being
dragged. Dragged insinuates that you
don't care about performance. You don't
care whether you succeed or not. You're
just being sucked into the void of
success. You might be able to say that
for a rock star that gets a hit song,
but um most of them doesn't last. I you
need massive amounts of of drive. And I
love the most the most exciting thing I
like to do is when someone tells me
you can't do that like watch insurance.
You will never launch a watch insurance
company. It you will never do that. You
will never get around the compliance
state by state. You will never launch in
the Middle East. You'll never launch in
England. [ __ ] That's exactly what I
did. I found the right team. I found the
right partners. I figured it out. I I
was passionate about it. And I think I'm
going to kick ass. I think I'm I think
in two or three years from now you won't
be able to catch up with me. That's what
I think.
I'm 32 years old. What What is the
advice that you wish you got at 32 years
old? Kevin,
what I have learned and this is
something that you should really think
about for yourself.
Your real value, your real brand
are your followers. this army of people
that have decided to invest their time
in you. You know, you've cut across a a
vast swath of people. So you influence
very successful managers, CEOs, and a
lot of young entrepreneurs want to hear
what you have to say because they
they're expecting you to deliver
valuable information
across
multiple sectors and you also have your
own data, but men and women. And so
where do you take that? Because you know
it's do you want to launch a clothing
line? Do you want to sell burgers? Do
you want to do consulting? You know,
it's it's you have all those
opportunities, but what fits your brand?
And so,
I have and you'll get to do this. You'll
get to do this. You'll be approached by
a lot of people that want to ride that
network you've built. And my advice to
you is
because this has really worked for me.
Is is this a product or service that I
personally would use that I would
actually use?
Because you'll get offered a lot of
money to talk about one brand or another
brand. They will. And you may be weak
and take it. But
the minute
anybody in your network, in your
community thinks you're not authentic,
you're [ __ ]
And you know that.
Yeah.
And so you better be authentic. You
better be transparent. You better be
honest. Even when turmoil hits, whatever
it's going to be, I found that saved my
ass so many times by just saying,
"Here's what I know. Here's what
happened." And that actually bonds them
even closer to you. And and that's
that's the difficulty you're going to
have is how much do you want to take ne
because you're going to have that
opportunity. But if you stay authentic
and say I'm going to do I'm going to
support this brand because I use it.
Every single brand or commission I have
in supporting a business I use myself.
I'm a shareholder in it and I believe in
it and I use the product or you know
whatever like the wines I make myself
with my wife we drink them at our family
and everybody knows that. So you
if it's I wouldn't drink it if it's [ __ ]
wine. Yeah.
So it's it's sort of like
that's my advice to you because I meet a
lot of people but you're very rare. you
what you've built maybe by
happen chance that it occurred. Whatever
alchemy occurred, you have it now. It's
yours to lose. Don't [ __ ] it up.
No, everything you said is so true. And
um obviously the things that I uh the
things that we talk about in the show in
terms of brands that I promote, pretty
much all of them I've invested my own
money into. Yeah.
And this is like super important. So I
talked about my Whoop. Yeah.
Um,
if you look at the investments I have
and the things I talk about, there's a
really clear through line through them.
So, there's a really clear through and
it's actually reflective of just where I
am in my life. There's actually a
sponsor I used to have on the show that
I was very big on. And I just stopped um
I stopped consuming the product. They
offered me £6 million
which is about what $8 million to
continue for another year and a half.
And I said like it just wouldn't I'm
about to basically start
um
talking about and investing in the
antithesis of what you do.
Yeah. So, I had to turn down that $7
million, which is a lot of money for
anybody.
Yeah.
But it's because my life shifted and I
shifted in a different direction. People
don't see those things. They they don't
see that the this foreign government
comes along and offers you $4 million to
go and talk about their country or to go
do the dario in their country. They
don't see those decisions that you make.
But I think hopefully if you listen to
me long enough, you'll see a through
line between the things that are
authentic to me.
Yeah. And I think that so you've already
figured it out. And the other thing that
I would do and say anybody your age and
because I wish I'd done it is start
focusing on longevity in your 30s. Start
thinking about what you eat and what you
drink and how much sleep you do and how
much exercise you have. You're you could
live to 120 years old. I mean
crazy,
you know, it's sort of if if you
understand if you're wearing a whoop,
you know what I'm talking about. It's
sort of I am very very uh focused on
what I do and exercise and what I eat
and all that. Um, but uh that makes you
feel healthier and more and just better
about the your day as you go through it.
But the fact that you figured that out
at your age because most people your age
would have taken the 7 million pounds or
whatever it was, that would have been a
huge mistake because now the next
product that you do endorse, I will know
with certainty that you use it because
you told me this.
We have a closing tradition on this
podcast where the last guest leaves a
question for the next guest, not knowing
who they're leaving it for. And the
question that was left for you, funnily
enough, I feel like I might have asked
it, is where do you believe happiness
really comes from?
You know, I think the answer is very
simple. Consistently achieving your
goals because happiness is not a
destination. It's a journey. That's what
it is.
So you have to set those goals whether
it's noise to signal going full circle.
talked about or long-term, whatever it
is, it's consistently achieving those
goals, you will be happy. Consistently
not achieving them, you'll be unhappy
because it is not
a destination. Happiness is not a
destination ever. It's a mistake that's
so elusive. I mean,
it's just not a destination. It's a
journey. That's it. This is one of the
great things you've taught me today and
reaffirmed for me today is this idea of
like signal and noise and radical
prioritization because kind of
dovetailing into what we were just
talking about. When you have a lot of
opportunity, it gets even harder, I
think, to know which ones should be
taking your 18 hours a day. This is
something I struggle with.
You should feel it. You know, you're
you're kind of a weird dude because
you're like a 70-year-old man in a
30-year-old body. Like you've got you've
got the intellect of of experience,
which most people don't have at your
age. But deals
There's a certain feeling that you if if
you should feel that it's a good deal.
It should it should be in your gut. And
I've learned this. There's many deals
that sound great that when I just do the
gut check, I don't participate in. They
just don't give me and that came from
experience. But you seem to have that in
some weird way to avoid that one we just
talked about. That's it. It's it's it's
an intuitive feeling that you generally
get by having a lot of winners and
losers over time.
But you seem to have accelerated that
somehow. It's an intuitive nature of
where you want to get to and what it's
going to take to get there. And there's
going to be sacrifice along the way.
It's never about the money. Never. It's
not about the money. It's, you know,
it's do I want to achieve that goal?
You know, I'm having a it's it's just a
weird thing because I I had a similar
situation just a couple of days ago,
you know, when somebody approached me
and said, "Look, can you get behind this
and and back it and I'll pay you a ton,
like just a crazy amount of money." And
I thought, "Do I actually want to spend
one hour pursuing that?"
And I went back and said, "Look, um, no.
I I just it's just not interesting. I I
just I don't I can't see my I can't see
myself getting involved in that
narrative, which was it was a
complicated situation, but
and then he said, "Look,
how about I give you two and a half% of
the company?"
I said, "No,
I I just don't want to be associated." I
you know, it's just it's the same idea.
It would intuitively
It was noise.
Yeah. And what that would do is some
opportunity you don't know about down
the future that you you you you pursued
some goal that somehow tainted your
brand and that opportunity never comes
to you. You you're you're the you're the
captain of your brand. You got to you
have to define yourself right through
the journey. It's hard. It's really
hard, you know. It's it's uh
it's really hard. and that and that if
if there's going to be a downfall for
you, you will have chosen unwisely
somewhere. But it better not be from
money. That's there should never be an
amount that you would take because if
your gut says no, it doesn't matter what
the money is. Not after what you've
achieved. I mean, you don't need to buy
a guarantee anymore. You got it. I'm
assuming you've put some away. I mean,
it's very simple.
If you've got five million bucks in the
bank, you can do whatever you want. Now,
I mean, it's may sound I want more, but
that is enough under cat. Always have
always I have an account that just sits
there with 5 million bucks in it in T
bills. I never touch it.
That's my nest egg.
Kevin, thank you. You go.
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Summary

Kevin Oly’s Blueprint for Wealth, Entrepreneurship, and Life: Lessons from a Self‑Made Millionaire

Early Influences and Investment Philosophy

Entrepreneurship: Who Can Succeed?

Signal vs. Noise: The Core of Execution

Hiring, Diversity, and Women‑Led Success

Real Estate and Mortgage Discipline

Diversified Portfolio: Stocks, Bonds, Crypto, Watches

Role of Marriage and Financial Compatibility

AI, Crypto, and Future Technologies

Practical Advice for Young Entrepreneurs

Final Reflections

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