How Billionaires REALLY Think: 30 Questions Answered!

The lives of billionaires
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3 Video Views·Mar 3, 2026
Robert Herjavec answers 30 common questions posed to billionaires. The insightful discussion covers diverse topics, from debt management and business partnerships to personal relationships and the pursuit of success. Learn how one's perspective on wealth evolves with age and experience.
Hey everyone, Robert Herjavec here.
Welcome back.
Our last segment, Top Questions People Ask from Billionaires,
was so successful, I've decided to do it again.
Top Questions People Ask Billionaires.
Here we go.
If you have nothing to sell, sell joy.
People will always remember the emotion they had when they met you.
Protect your energy.
It's more valuable than your money.
Here's my answer.
My dad had the best answer for this.
He said, if you work hard and save,
you will never be poor.
But just because you save and work hard,
doesn't mean you're going to be rich.
You cannot get rich or wealthy
without knowledge, leverage, experience,
all of those things.
But, life is a constant.
Think of it this way, it doesn't just happen one day.
So depending on where you are in life,
it's really good to save,
it's really good to get comfortable,
it's really good to have protection and security,
and then you can try to go for the big bucks.
When I was 20, I was desperately poor.
There was a sense of desperation to me,
that I would love to tell you I wanted to build great businesses,
do great things, you know what?
I just wanted to make money.
So for me, money in the 20s seemed finite.
It seemed like I'm going to get there,
and then the world was going to become this magical place.
I mean, I was a millionaire in my 20s,
in my 30s I sold a company for $35 million,
and all of a sudden, I was rich.
It started to get me to think,
what was really the purpose of that money?
What made me happy?
And how can I create great value?
Today, in my 60s,
what I think about is protecting my assets,
because I don't want to go backwards,
but I also want to take bigger risks.
I want to do more.
And I think you'll find most people who've done great things
are pretty restless.
They don't sit around for very long,
and I definitely fall into that camp.
So the answer to that question is,
it depends where you're watching this video.
If you're watching this video in India,
and you're making $100,000 a year,
guess what? You are doing great.
If you're making $100,000 in Manhattan,
you're probably paying $5,000, $8,000 in rent.
You're barely getting by.
So how much money you make as income
is directly related to your life circumstances.
But here's the question you've got to ask yourself.
At this point in your life,
that you're watching this video,
what is more important to you?
Income or experience?
If you're young, or if you're in a position
where you don't have or need a lot of money,
you should get the job that creates the experience you need
for the future.
It depends.
As I got older and got into business,
what I realized is there's good debt,
and there's bad debt.
What's good debt?
Stuff you can write off, stuff that grows your business,
a second home, things like that.
Bad debt, personal debt, credit cards,
all that kind of stuff.
Well, you should try to pay it off.
How do you pay it off?
If you have the means to pay it off,
you've got to get there faster.
The faster you pay off the principal,
the less interest you're going to pay.
The question becomes,
how much are you willing to suffer
in order to get debt free?
And this is where saving $5 on a coffee does help.
This is where not going out for dinner helps.
This is where a couple of years of sacrifice
is going to get you ahead.
Very, very hard to build a great business
when you have that much personal debt.
Now, if you're really behind,
you should go see a debt counselor.
There are great companies out there today
that can help consolidate your debt,
put it all in one program,
and help you with a repayment program.
The biggest relationship mistake
that entrepreneurs make is two things.
They get into business
and their judgment is people they like.
Oh, here's my friend.
I like him. We get along.
Let's get into business.
You should get into business with people
that supplement the skills that you don't have.
So if you're great at sales and you can't do engineering,
bring an engineer into the business.
Bring an accountant into the business.
Number two, you have to have
a very clear path for disagreement.
It's like marriage.
People always assume it's always going to be a workout.
It's always going to be rosy.
But you should treat it like you're about to get divorced.
Who's going to make those decisions
when you don't get along?
Here's a hard reality.
The business doesn't care about you.
The business is a living, breathing entity.
Think of it this way.
When you start a business,
you've adopted another child.
Or for those of you who have kids,
you've adopted another puppy.
And for anybody who's had a puppy,
when the puppy has to pee at 2 in the morning,
guess what you're doing?
You're getting up at 2 in the morning
to take the puppy outside.
Your business is a living, breathing thing.
If you are not willing to commit to that business,
above everything else,
at the beginning,
you're really going to struggle.
Now, I have great balance in my life,
but I also have great wealth.
But I didn't have that balance
probably for the first 10 years of my life.
Business is really hard.
It has no emotion.
It doesn't care about you.
It just wants constant nurturing and feeding.
And that's the way it is at the beginning.
It's hard.
Here's an answer you may not be expecting.
It's actually got nothing to do with business.
It's got to do with relationships.
Yes, look at me. I'm giving you relationship advice now.
The most important partnership
you'll ever have in life
is the person you marry.
I mean, they're for you or they're not.
People make the biggest mistakes,
the biggest hit to wealth,
but the person you marry
and the person you end up with
can be one of the biggest determining factors
in your success
or it can really weigh you down.
The world can be a really lonely place.
Finding the right partner
can make the darkest days
a lot sunnier.
My general experience, though,
is most people
are not lazy.
Most people are afraid.
Fear is numbing.
Fear can stop
people from action.
And it's really hard to get ahead
without action.
It's a great saying somebody said to me a long time ago.
There are many dreamers,
but there are very few people
who are obsessed.
A dream doesn't require anything
from you.
A dream is a wish.
An obsession requires
action.
So the reality is,
are you lazy?
Are you afraid?
And that's okay.
Because many, many people are.
But the things that you want,
are you willing to break through that fear
and change your life
and take action for it?
Is there periods
of time in your life
that are wasted?
Have you ever thought about this?
Whenever you sell a company
or you try to raise money,
most of the people in the room
come from equity or venture capital
and they all have super fancy degrees.
But none of them
have ever started a business.
Doesn't that sometimes make you think?
So that's one.
The second one is partying.
You know, in your 20s,
you've got to make a decision.
Either enjoying life and partying
is important to you,
or getting ready for your 30s and 40s
is more important to you.
I mean, it was easy for me
because I was a super geeky guy
who didn't have a lot of friends.
So there wasn't a lot of temptation.
I was not getting invited to a lot of parties.
So it was easy for me to stay home
and learn and study
and start a business.
You can waste time at any point in your life.
Colonel Sanders started Kentucky Fried Chicken
when he was 64 years old.
You're never too old for success
and you're never too young for it either.
The first thing I say to myself
is the sun
will always shine
the next day.
I've learned life is long
and no matter how bad today is,
tomorrow
is the opportunity for better.
Easier said than done,
when my mom was sick
and she was in the hospital,
it was probably one of the worst times of my life
and I know it's easy to say,
oh, the sun's going to shine tomorrow.
But I couldn't do it.
I didn't have the mental fortitude
to wilt myself
to feel good.
So I did something that stayed with me forever
is I started running.
I've basically run almost
every single day five miles
since that day
and it stacked me out of it.
You know why?
The pain of running was so uncomfortable
that the mental pain
of what I was going through
came second.
But every day when I run,
it's a small win.
I need that and it means
so much to me on those days.
So you've got to know
what works for you.
Well, when I was a kid
in another century
they didn't actually diagnose
for that kind of stuff.
I mean, it's funny, when I was a kid
I don't remember any kids that were diagnosed
with ADHD or
peanut allergies or any of that kind of stuff.
But for sure
I had a
very, very difficult time
with being hyper.
So today I would be diagnosed
probably with ADHD.
I tend to get very hyper.
I had a very, very difficult time
controlling my emotions.
What I've learned though
is you've got to control
your emotions. Interesting fact,
half the sharks
are dyslexic.
Mark, Damon, I think Barbara
they have a very difficult time
with numbers. They superimpose numbers
when they look at them, but they
know that. And so whenever they go into
a negotiation and have to look at some numbers
they make sure they do it
again and again and again.
Just practice.
So do you need the perfect plan?
No.
What you do need though is a vision.
What I realized in my 20s was
I can't get to
where I want to go in one
year. So when I was
tired of being poor, I remember I sat around
I got a piece of paper, I was going to do all these
things. And I looked at it and I said
there's no way I'm going to do this
in one year. You always
overestimate what
you can achieve in one year
and underestimate
what you can achieve in 10.
When I started in my 20s, I was
poor, no idea
what I wanted to do, didn't know a thing
about cyber. By 30
I was a multi-millionaire. I was
one of the top people in the world on
cybersecurity. I already built
and sold a business.
And I was looking to sell my next
business, which I did 5 years
later for $35 million.
Did I have a plan?
No. Did I have a vision?
Absolutely. It's going
to take you time. Start now.
Is
starting a business like jumping off a cliff?
Is it risky? Do I have to be
really risk-oriented
to start a business? No.
Starting a business
is not like standing on the edge
of a cliff and jumping off.
That's stupid. If you're going to stand
on the edge of a cliff and jump off,
walk to the bottom first
and see how deep the water is.
There are smart calculator
risks and then there are
bad risks. The other
thing I've learned is never take
a risk that will kill your
business. I mean, I'm willing to
risk 50% of it. I'm willing
to risk a big chunk of it.
But I've tried not to make
bets that are so big
that I lose everything.
I think it depends
where you are in your life. In my
20s, I was definitely
not the result of the 5 people
I hung out with.
I was working in a factory
during the summer,
loading trucks. Definitely
not the people
that were the result
of my success. You can find
greatness and energy and joy
no matter where you are,
no matter what kind of a job
you have. But in general,
you tend to attract
the people. But in your
20s, don't worry about it.
You know what? As you get older and you get more
successful, you'll attract
the people that you were meant to
attract. One of the
things we always hear
is, if you lead a hard life,
good things will come to you
or things will be easier
for you. Yeah.
Absolutely.
I mean,
I've had the pleasure of speaking with
Cameron Haynes via text.
I've had the incredible
pleasure of meeting David Goggins
a few times. Those guys are
hard. I mean, I like to think
I'm hard. I am definitely
not. If you're hard on
yourself, life
will be easy on you. That is just
the reality.
If the hardest thing you do
in a day is something
that you've chosen to do,
your life is going to be easier.
Definitely in my 20s,
I was chasing something. It's not
that I was chasing something.
I was running away from
poverty. I was running away
from the way we were living.
I was running away from being made fun
of. I had a massive
chip on my shoulder and it probably
helped me through all those dark times
to get ahead. Once I
kind of got there and I won,
it didn't change
me, but it calmed me.
It stopped me from running
away from something
and made me think about
where I'm going.
And that was the biggest change.
AI is going to change everything.
And guess what? We're just
at the very, very beginning.
If I was starting out today,
I would spend
every waking moment
learning about AI.
Just like I did at cyber security.
Not that cyber security is dead or any
other industry, but AI
will be such an amazing
force for change.
You've got to get on that bandwagon.
I don't really think that way.
I have a very fatalistic view
about life. I think
when I'm gone, I'm gone.
My lawyer, who's
a friend of mine, had a great saying
many years ago, which was
you can't rule from the grave.
If I had one thing to leave
the world, I wouldn't necessarily
leave it for the world
because I hope I made an impact
on some people.
While I was here, I would say it to my
kids and my wife.
And all I would leave them with, one sentence,
I love you.
I've never been burnt out.
I have come very,
very close to the edge of burnout
and then I just shut
down and move away.
You cannot be successful
unless you're healthy.
And that's physically and mentally.
And I think I've always been fortunate
to know when I'm overwhelmed
and just break
out and do the things that
bring me back down.
For me, it's working out, watching TV,
just whatever.
When I had nothing,
I thought rich would
feel warm
and devoid of anxiety
and fear.
And guess what? For money,
it's true. Money is
a massive stress for most relationships
and most people. Once you get
over that, life doesn't
just stop. I mean,
being wealthy
isn't something that you walk into
and all of a sudden, every single day
is sunshine and
unicorns. There are bad things that
still happen to me. It felt
good not to worry about that
but that alone doesn't
guarantee a happy or enjoyable
life.
This is a great question.
I think everyone is obsessed with getting
a mentor, but it's really hard.
I mean, people say to me, oh, can you mentor
me? Like, I have time for that.
It's really hard to find
a mentor, but
there are models.
YouTube, books,
there are lots and lots of people that you
can model your life after.
And here's the beauty of it. My models
today are different than they were in my
20s because my skillset
and my needs are different.
So I think you can find mentors and models
everywhere, but don't
forget, the people that come
into your life that guide you,
they work in that period of time.
If you're continually growing,
you're probably going to need new
mentors and models along the way.
That's a great question
too. And if you look at
high net worth, it's like
this. Like, here's the amount of millionaires,
here's the amount of 10 million,
50 million,
decamillionaires, and so on. It gets
smaller and smaller and smaller.
But the biggest difference between
a million and 10 million
is your ability to leverage
other people. I don't mean that
in a bad way, but your ability
to work with a team and get
the team to a
mission that's important.
You know, to become a millionaire, you just
got to work really hard.
You can start a company, you can power
your way through to a million.
But typically, to get
to 10 million, you need a team.
I'm a
huge believer
that every small business
is a byproduct of
the entrepreneur. So,
show me a small business that's in trouble
and I'll show you an entrepreneur
that's going through something.
And you know what? Sometimes life does
happen to you and you've just got to get
through it. But I really
believe that it's, you
can't be successful unless
you're personally successful.
There are absolutely bad people
who achieve
incredible amounts of success
and they're just really miserable
bad people. But I like to believe
they're the anomaly.
They're not the rule.
The riskiest and
scariest decision
I ever made
was going on Dancing with the Stars.
I'm a TV guy, obviously,
but Shark Deck is five of us
sitting in a chair talking about business
super easy. I mean, it comes
native to me. Dancing
in front of a thousand people live
and tens of millions at home
for a guy who's never
danced or done live
TV. Did it pay off?
Absolutely. That's how I met Kim.
Working out
it's like meditation,
energy,
focus, everything
for me. My day is so busy.
I rarely get time just to think
and all my friends think I'm
really not very social because they're always
like, hey, let's go run together. Let's work
out. I'm like, no, I just want to do it on my
own. Focus, focus,
focus. It's probably
the biggest daily contributor
to my success.
The absolute
first thing I would do
is go into the field
where I'm an expert.
The world rewards expertise.
So part of my success is
not built on the fact that I've
leveraged money. My success
is built on the fact that I really knew
an industry, cybersecurity.
Now I really know AI.
So if I lost
it all, I would probably start
a services-based business.
Why? Because I don't need any
capital. Build up from that,
provide value,
and do it much faster.
If you've ever seen horses,
they wear blinders.
They wear these things on the side
of their head. Do you know why they give that to
horses? So the horses stay focused
on going forward. Otherwise,
the horse looks this way, that way.
The world is full of distraction.
We are bombarded with stimuli
all day. The other thing
I try to do is try to figure out
what are the, and I write them down,
what are the three things
I need to achieve today?
Every day you're going to need to do 20, 30,
40 things, and then the world's going to add
more. But there are three things you need
to do today to move
the ball forward. It's the
ability to be able
to filter out
the truly urgent
from the important.
I love cybersecurity,
and I would probably go back into that.
I'm still involved with it. I'm still involved
with my whole company. I'm on the board,
and we have great board meetings.
We have a great new CEO.
But I would also get into AI, which I have
gotten into because
I think it's the future. I mean, I love
technology because it
absolutely rewards you
for the value that you have.
I hope you enjoyed this video,
and if you did, please subscribe,
and if you have any questions you'd like
me to answer in the future, please
send them to me.
