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September 22, 2025 49 mins

In this episode, Ashlyn sits down with entrepreneur, author, and motivational speaker, Gary Vaynerchuk. They dive deep into what made Gary into the man he is today. Whether it be his mother, father, or grandmother, Gary absorbs every lesson he’s taught and puts them to practice. Together they consider different approaches to parenting, observe the insecurities men and women face, and talk about how to become comfortable being uncomfortable.

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Speaker 1 (00:02):
Love.

Speaker 2 (00:04):
Today on Wide Open, I'm sitting down with someone who's
built an empire out of hustle, heart and unapologetic honesty.
You know him as Gary Vee, entrepreneur, investor, best selling author,
and one of the loudest champions for betting on yourself.
He's turned his love of sports, culture and community into

(00:26):
a global platform, from growing businesses to dreaming about owning
the New York Jets one day, We're going wide open
on what drives him, what grounds him, and what's next
for one of the most unfiltered voices of our time.

Speaker 3 (00:40):
Welcome to the show. Gary, How are you.

Speaker 1 (00:43):
I'm super well. It's so nice to be with you.

Speaker 3 (00:45):
Have you been at I'm good, I'm good.

Speaker 2 (00:48):
This is just so exciting for me because, as you know,
I adore you and I've been able to follow you
for a really long time and I love the way
you show up in the world and it inspires me
and definitely I always keep it in my back pocket
and the way I move in the world. So You've
had a tremendous influence on me and I don't get
to tell you it enough, So I'm telling you at

(01:10):
the top of the show.

Speaker 1 (01:12):
Very sweet. Thank you. I'm excited. Let's let's let's win
for your audience. What you mean, jamb On, let's go.

Speaker 2 (01:17):
Well, I think so much of what you've done on
social media, you've you've really laid out, you know, groundbreaking
things on what drives you and grounds you and what's
next for you. And you're so unfiltered about the way
you see the world. And I would love to start
there because I genuinely think you see what people can't.

(01:41):
I find that a superpower. And I'm curious because you
you know, you came to this country very young, you
were an immigrant. You know, your family had a wine business.
Did a lot of those beginnings shape the way you
see the world differently because you had.

Speaker 3 (01:58):
To at an early age? Or where does this drive
come from?

Speaker 1 (02:02):
I think there's a lot to it. Look, I think
long before I walked Earth, we figured out there's a
nature nurture thing, right, And so you know this about me,
and it's just you know, even I actually try to
limit how much I publicly give my mom over the
top credit because I think it's you know, for people

(02:24):
that follow me carefully, it's like truly a broken record.
But I would say it starts with I took a
lot of really special DNA traits for my mom. I
think many people grow up with little. You know, many
of us grew up with little. I don't think that drives. Yes,
that's a driver, but I believe a lot of us

(02:46):
grew up with little, and we then become insecure and
our driving fuel is actually not healthy and not sustainable.
I grew up with little, but had the reverse element,
which was I was mothered so well that my self
esteem was pure and not a facade, which allows me

(03:09):
to both be hungry and ambitious, because obviously I was
taught that if I'm hungry, I have to go hunt
to eat. It's very hard to be hungry when you're
being fed, right, Yeah, and so yes, of course, coming
from the Soviet Union, understanding how bad it was there
coming to American in the eighties, a golden era of

(03:31):
the American dream, having parents that not only did not overcddle,
it was almost a sacred sin to complain in my household.
Probably in hindsight too far, like there probably could have
been a little bit more vulnerability and communication. But what
I definitely have is the combination whatever learning disability, dyslex it,

(03:54):
whatever it was that I had, which I've never been diagnosed.
But whatever I had that didn't know allow me to
be a good student definitely did the cliche thing that
many of us talk about with bad students, which is
it enabled me to learn differently. I wasn't interested in
memorizing facts for tests, nor did I. What's very clear

(04:16):
to me is I had such poor reading comprehension that
the way I learned was not by reading, but it
was by a different kind of reading, which was reading
people right. Yes, And my audio skills and my visual
skills are through the roof. I'm that guy who if
you and I took a road trip right now for
an hour and forty five minutes with many different turns right,

(04:39):
many different turns, I'd be able to redrive that drive
six months later easily because I'm so visual in how
I learn, and then audio ash it's crazy, like if
I hear it, it's locked. So I think whatever I
had struggles with reading comprehension, which hurt me in grades,

(05:02):
created these other superpowers. But I would tell you above
that because that's also cliche. I think the one unique
thing is that me with me, meaning my relationship with
my intuition with my gut M is so strong. I
trust it so blindly, and I think that has a

(05:23):
lot to do with a complete lack of fear of
the judgment of fellow human beings when I'm wrong.

Speaker 2 (05:32):
Yeah, that is powerful, and I do think that that's
what holds a lot of people back. Is that fear,
that fear of failing, the fear of the insecurities that
come with it. And I think, you know, you and
I tick so similarly similarly, and I love that, like,
because I you're speaking to my soul right now.

Speaker 3 (05:51):
I went through the same issues.

Speaker 2 (05:53):
I was in learning disability classes when I was younger,
but I saw the world differently and I would shamed
for it as a child, but it became my superpower
because I bet all myself and I was like, watch,
I'm going to get out of here.

Speaker 3 (06:06):
I'm going to figure it out.

Speaker 2 (06:08):
And this sports and you know, my hunger and my
competition and my my work ethic and drive will always
be there when everything else fails.

Speaker 1 (06:19):
We were literally the same except our vehicles yours with
sports mind was entrepreneurship and business, but literally all the
same stuff. And this is why I speak so much
about do not take competitive DNA out of your children
by giving them eighth place trophies and saying what I
believe is one of the worst things you can tell
a competitive child, which is, it's just a game. Yeah,

(06:43):
it's literally actually the reverse. Everything is a game. I
would actually say that telling a child that is competitive
because you feel bad that they're crying because their team
just homes. Telling that child, but buckle up, up, it's
just a game. It doesn't matter. It's just a game,

(07:04):
is actually teaching a child the worst possible thing, which
is you're teaching your child in difference, I believe grown
ups that are indifferent go to very unhappy places, and
that is fucking with society. That is fucking with nature,
That is fucking with the human spirit, and it is

(07:25):
hurting people. This And just so you know, everybody who
doesn't know me, who's listening to this right now, yes,
this is a PSA to stop doing this, because I'm
telling you for the people that don't know. I have
fifty plus million followers in social I've been very in
social for a very long time, and I over index
with youth culture, so I've been on the receiving end.

(07:46):
And this is the real number. For about the last
seven to eight years, I'm on the receiving end of
over ten thousand direct messages a week and sometimes a day,
and a lot of it is fifteen to thirty five
and an extraordinary amount of research that I've done over
the last decade, and I'm telling you it is very

(08:07):
clear that the eighth Place Trophy thing has been very
detrimental to mental health. And it was well intended. I'm
not mad at why it happened. I know why it happened.
It didn't come from a bad place, it really didn't.
But many things are well intended that are go awry.
So anyway, yes, that's just my little rant on eighth
place troop.

Speaker 2 (08:27):
No, I do, because you know, I feel the same
way you feel, because like sports have been so pivotal
and the way I see the world and the way
I show up, And I do think you know, you
grew up playing.

Speaker 3 (08:41):
Sports, you love sports.

Speaker 2 (08:43):
You've been very open about, you know, speaking your goals
into existence. You're like, yeah, I want to fucking own
the Jets one day period, and well, I.

Speaker 1 (08:52):
Love there's also there's there's also something that comes along
with that, me chasing. Yeah, the new York jets is
actually more excited and intoxicating than buying the jets for me,
Like I realized this about me as an adolescent, when
I was a cute little fifth grader and all the
girls like me. Getting the girls to like me was
way more fun. I was scared of girls once they

(09:13):
were like really in pocket, like really like me. I
was like, oh, I'm scared. I'm scared to kiss a
girl right now. Yeah, I'm like, I'm not there yet.
I wasn't mature enough yet, but like, you know, I
love process over was you know, if I was gifted
athletically the way you were, and we had the great
luxury of being teammates and we knew each other, and
somebody said, what about Gary B you would have said, Man,

(09:34):
nobody fucking loves practice more than that, dude. He loved
the game more, but his love for the practice like
my my love for eating shit. For the pain. I
would have been a great fighter. I would have been
a great fighter. I love the pain. I love getting yesterday.
In my many companies, I have probably three thousand employees

(09:55):
maybe even more now across all my companies. Every day
I'm dealing with pain. Mm Hmm, there's this legal you know,
we got sued for this bullshit. H This person's mother
is diagnosed with cancer and she has to fly immediately
and she'll be gone for two weeks. Uh. This person
got hurt. This person's house burnt down. This like, this

(10:17):
person said the wrong send the text to the client,
making fun of the client when they thought they were
texting their coworker, like my entire do you know, Ash,
You'll find this amazing when I go when I travel
and I put occupation, like when you step to do that,
you know, like one occupation you remember when you would

(10:37):
do like the filling out the form and an immigration.
When I used to put occupation years ago, before we've
gone to this full digital world, I would literally put firefighter.

Speaker 3 (10:48):
Oh my god, because.

Speaker 1 (10:49):
Really, if you ask me what do I do for
a living, I'm a firefighter. I fight fires all day,
all day, and I'm but even different. And this is
the key to why I say it. I'm always prepared
for the alarm to go off when I wake up
in the morning, I immediately grab my phone and read

(11:10):
all the texts from London, from Singapore, from all my offices,
from Los Angeles, like I'm always prepared for the problem,
and so I think that level of grit, having that
stomach for adversity, my comfort in the challenges is what

(11:32):
actually makes me happy, and everyone's trying to avoid it.
Our biggest issue in life right now, in societal life,
is our complete lack especially under forty years old. Because
I don't think this is just an I think we're
very unfair to gen z. I think this is a
millennial issue. And by the way, I want to give

(11:54):
a big shout out to our boomers. Half the boomers
were this way. They just like all like to make
pretend they weren't. Yeah, we are not comfortable with a
little discomfort.

Speaker 3 (12:05):
I agree.

Speaker 1 (12:06):
It's just bananas to me, Like people yelling, like have
you been to an airport? People yelling at the fucking airport,
Like these poor airport employees, like the plane they're not
letting you board it because they don't want you to
fucking die. Yeah, Like they're literally making sure the plane's
okay so you don't die. And you're gonna literally yell

(12:28):
yeah at the person at the gate for the two
hour delay because remind me, you can't wait to get
to Disney World and lay by the pool and drink
a margarita and go see fucking goofy. What the fuck's
the matter with you? I like, we are complete. Well,
you're mad at the barista because you put in the
wrong milk. This is worth a brating of a human being.

(12:49):
What the fuck is the matter with people?

Speaker 3 (12:50):
M I totally agree. I've been saying this for a
really long time.

Speaker 2 (12:56):
You know. I'll give you another example, Gary, I went
to the gym what was it yesterday and every person
in the gym is on their phone, working out, scrolling
on Instagram, listening to a podcast. And I don't have
anything in my ears. For a reason, it should be uncomfortable.

Speaker 3 (13:17):
I won't. I don't. I don't go into those space spaces.
And I'm like, hmm, this is my.

Speaker 2 (13:23):
Chance to lay on the floor and just put a
podcast in, and like might No, you go to work,
You go to fucking yeah.

Speaker 1 (13:29):
Look, look, you're in a stratistyre by yourself. You are
part of a very rare group of humans on earth
that were physically and emotionally talented and put in the
work to be actually not only a professional athlete, but
incredible at it. So that makes sense to me. Yeah, what,
but it's funny. I, on the other hand, only started

(13:52):
getting serious about physical health at thirty eight, so about
eleven years ago, right, My first workout with Mike Vicanti
years ago in hindsight is wildly laughable. I have so
I have so few muscles in my body and so
much fat in hindsight. But what I think is really interesting.

(14:12):
My version of what you're saying is Mike and then
Jordan and then Mike my full time. They live with me,
they travel with me trainers. What they did well is
they taught me for They're like, look, if you're gonna
do it, do it right, so you actually build muscle.
You're not here to impress the other bros. The thing
that I always pay attention to in the gym is

(14:34):
the guys and gals. But you know, boys are good
at this game. The guys that take on ten extra
pounds then they need to when they do arm curls,
but their entire fucking back is swinging swing to get
it up and this goes back. And when I see
them do that, and then when I go and do it,
and I'm doing five or ten pounds less than I

(14:55):
can probably with a little bit of extra because I'm
so obsessed with just just doing the form properly. That
to me also speaks about confidence and insecurity. Any dude
that's just swinging that way either a just doesn't understand
proper form, and I'll give people grace and say they don't.

(15:15):
But much more likely, especially because a lot of these
people are actually jacked to begin with, Like they're looking good,
they're doing it out of pure insecurity. They want all
of us to see they're doing sixty fives, not fifty fives.
And my mission in life is to get people to
live their life for themselves. Yeah, because I believe we've
The greatest pandemic that I've ever seen is not COVID.

(15:39):
It is people literally making every decision in their life
based on the subjective opinion of people around them. It's
one thing for that to be your loved ones, we're
now doing it for strangers.

Speaker 2 (15:53):
Well, that's what social media also has really you know,
scaled scaled.

Speaker 1 (15:59):
It's scaled it, but I would argue that it exposed it.
To remind everybody, keeping up with the Joneses was a
term coined long before Twitter came along. Yeah, so you know,
lifestyles are the rich and famous, you know MTV crib cribs.
We have seen wealth prior to social and people were

(16:19):
buying Mercedes Benzes when they couldn't afford it. They were
buying houses that were too big for them, they were
buying clothes that they didn't need to have long before this.
But no question, it's been an exploding pandemic. But I
argue it is not social. It is parenting has gone awry,

(16:42):
and we are just not as disciplined, we are not
as humble. We are using more and more, we are
taking the ultimate drug that's a bad drug, which is
called using money and debt to disguise. Are hurt and
we need to stop.

Speaker 3 (17:00):
But stay tuned.

Speaker 2 (17:04):
I'll be back in just a moment after this brief
message from our sponsors. That's a really good point and
I completely see that and so much. You know now
as a new mom, this snowplow effect of everyone just
moving things to the side so your children don't have

(17:26):
to be uncomfortable.

Speaker 3 (17:28):
I do.

Speaker 2 (17:29):
I completely agree with you, and that's why I do
think sports are so important, and competition is so important,
and losing and learning how to lose gracefully, and learning
to build the tools to work with other people and
see eat other people and get the best out of
other people and yourself.

Speaker 3 (17:46):
Like there's so many benefits.

Speaker 1 (17:48):
You said something so powerful there, you said, learning how
to lose gracefully. If you and I were hanging out right,
Like let's say six or ten of us got together
on a Friday night and we all just decided to
play Monopoly, right, and we're playing, and I lose, right
at some point, it is scary to me. What's actually
running through my mind? Yep? What's just to give you context,

(18:12):
what's running through my mind? Let's say you one, what's
running through my mind is like I am so upset
right now? Should I smash this wineglass and cut ash?
Like it's so dark?

Speaker 3 (18:22):
Ash, it's so dark yeap.

Speaker 1 (18:25):
The fact that I've been able to over the last
forty call it forty three years, because I can understand
myself at six on this issue, get to a place
where not I don't cry, I don't have a temper tantrum,
I don't sulk. I did all those things from six

(18:45):
to fucking I don't know yesterday, Like like, like I
so struggle with losing. I love competition so much. But
to your point, if nobody even let me, you know,
if everyone let me win as a kid. Or more importantly,
here's a big insight for parents. If your child doesn't

(19:06):
even want to play, it's your first indication to their insecurity. First, right,
they're nervous about losing in front of you. I'm telling
you you have to pay attention to these things. The
learning how to lose gracefully has been the great lesson
of my life. It has taught me how to control

(19:27):
my natural instincts and feelings. There are so many people
out of control in our society because they say whatever
the fuck they want in the comments and social there's
no consequences, there's no ramifications. And when you look at
modern parenting, we definitely don't spank or wit anymore, but

(19:48):
we don't even punish. We are teaching children, you did
this horrible thing or a bad thing, you eleven year old,
and we're going to talk to you about it, and
then and then you're gonna go have your phone and
hang out with your friends and like it's it's wrong,
they're neat. You must teach human beings. There are consequences

(20:09):
to actions.

Speaker 3 (20:10):
Correct.

Speaker 1 (20:11):
You know, somebody being on me yesterday or actually also
or the day before and was like, hey, Gary, recently,
I feel like you got a little too hard and
like a little too tough, and like I think you're
promoting toxic parenting. Like the kid was basically saying, like
you're promoting parents like whipping their kids, like like physically
abusing their kids, and like, Yo, you're taking this naughty

(20:32):
out of content. I am not on this podcast saying hey,
parents need to like fucking take a switch from the
fuck it, like, like you need to like what I
grew up with. There was a belt in my house
when I was a kid.

Speaker 3 (20:45):
The paddle and the belt was hanging.

Speaker 1 (20:46):
Oh look, I'm not saying that. I'm not saying, like,
your kid steals some bubble gum from the store, And
the answer to that is they come home, they're seven
years old, and you take your belt off and you
whip their fucking ass. But what I am telling you
is your little story about like stealing is bad. It's
not the punch line either. You need to take the iPad,
the fucking video games and all the after school fund

(21:07):
leisure and all the fun away for a week or
two something. Let them taste that something happened. In fact,
back to my beloved New York Jets. Something very profound
happened today. Aaron Glenn our new head coach who comes
from a more disciplinarian coaching background. He was coached by
Bill Parcells, who's a legendary disciplinarian. The Jets lost on

(21:28):
Sunday to the Steelers. I was devastated. They lost because
a young player fumbled on a kickoff and set up
another easy touchdown for the Steelers. That was the difference
in the game. The Jets cut him today. Now for
context for everyone, this kid, he's a great kid, by
the way, as a human, the kid is unfortunately fumbled
a lot in his career. Last year in the NFL,

(21:48):
he fumbled more than any other player. Fumbles are devastating
if you don't know football, because it turned off the
over the ball. It usually is a big katter who's
going to win the football game because in the NFL
the teams are so close. Anyway, this used to happen
all the time nationally, all the time, this exact situation.
You have a fumbled kind of DNA, you fumbled in
a big spot. A new coach wants to set the

(22:09):
tone and they cut the player and you know this
cutting the financially impactfully, this real stuff. But it's a
lost art in today's even in the NFL, the coaches
are a little more softy softy. It is very clear
to me that players number forty five and to fifty
three on the Jets roster this morning. You know the

(22:31):
players at the bottom roster, yeah, are going to walk
into film today. And you know this, You know this
better than I do. I mean, I rep athletes, and
I know they're going to pay much more attention. I
have a very funny feeling, and it's and I'm saying
something important. I'm saying something that is fundamentally affected the

(22:51):
livelihood of a young man that I know. I don't
know him personally very well, but I know so many
of the Jets players, wonderful kid. Mm hmm. I don't
sit here happy today. I'm sad for him. This business,
it's business. Somebody got fired today, a mad or media
like it happens.

Speaker 3 (23:09):
Business.

Speaker 1 (23:11):
It speaks about consequences and what it means. In fact,
I hope he goes and signs with another team, and
I hope this moment makes him hole like put in
the work or whatever he has to do to not
fumble as much. And I hope he has a wonderful
career as long as it's not in the AFC. I
don't want him to bite us back in the ass,
so go to the NFC. But the punchline of that

(23:33):
story is if you're a parent, if you're a boss,
if you're a manager. And by the way, I have
made this mistake because I love a good culture in
my company. I have struggled with firing because I feel
like I'm directly affecting someone's livelihood mm hm. And I'm

(23:53):
so passionate about eliminating fear. I'm actually filming this right
now with two new employees that are in my inner circle,
and their first couple of days here, their behaviors were
so clearly grounded in fear of wanting to show me
that they were up for the task. You know, they
were capable. They wanted to impress me. And I'm such

(24:17):
a public figure, like even just like what do they
know about me? Like how can I show garret? You know?
And in different ways I told both of them like, hey,
I'm telling you from the bottom of my heart, I
know you've probably been fucked before, or things of that nature,
you've got time. Yeah, I think we're a month in.
I haven't even this is true, by the way, and
I'm obviously doing two things at once right now. I

(24:38):
haven't even begun to judge if I think they're good
or bad. I have too much grace to allow them
that they have to contextually learn. In fact, most of
the things so far in the first thirty days that
I've observed, and I'm like m have been grounded in
over compensation around with fear, being too frantic. I like
com in my obsession of eliminating fear as a leader

(25:01):
of three thousand men and women at my worst in
many pockets over the last fifteen years, I've created entitlement.
It's one thing for these two young gentlemen who I'm
gonna give time. It's another thing when they're now here
for two years. And I struggled with sitting down and
being like, hey, Danny, now it's December twenty twenty six.

(25:24):
I can't have you doing what you were doing in
August of twenty five because it's just bothering me. It's like,
not the right way. It creates fear for everyone else.
And so the first part, I'm very proud of. This
is second part I've not because I would believe and
I want everyone to hear this is for parenting and leaders,
coaches and business leaders. My December twenty twenty six conversation

(25:48):
with Danny that direct I would leave that meeting thinking, fuck,
now he's scared. He's gonna get fired in thirty days.
He's probably on LinkedIn right now looking for another job,
and basically it's over anyway because now he shook and
there's no way for him. Right That's how I looked
at it, and I looked at it wrong. I want
everyone to hear this, and I want this is where
this is where I was going. I looked at it wrong.

(26:12):
When I finally had a revelation that that was my kryptonite,
the lack of candor at a certain point in the
life cycle of a relationship or of an employer employment
here in my companies, that my lack of candor was
actually creating fear because let me tell you what would
happened to actually because I wasn't because I believed what

(26:34):
I just told you. I believed what would end up
happening is people would just eventually get fired and didn't
get the grace for me of that conversation, and what
ended up happening over time is my reputation would have
became it's all smiles and it's all pats on the back,
and then there's just a random day you're fired. Now

(26:56):
I have a much better mechanism. In fact, just two
days ago, I sat down with the young lady who
was let go Friday last week and she's been here
two three years. I adore her and she thanks me
to the high heavens because I've implemented the last five years.
She was so over communicated with that she was able

(27:19):
to get self awareness from it. And though she's devastating
because this is her dream, it was devastating. It was
like my central casting moment. She's wonderful. I like want
to be her best friend forever. This is her dream job.
I'm her hero in advertising. It's she's the breadwinner of
her family. She had a very senior role, and yet

(27:40):
we are in the most devastating thing that I could
think of, which is the firing of her. And she
was in an incredibly grateful, wonderful place, and that would
have not been achievable five years ago and is only
now because me and the organization have a level of
empathetic kind candor, and that's where parents are missing the boat.

(28:02):
They can't tell their kid that they suck at something.
You know, well, they don't give them the candor, they
give them the kindness, They give them the delusion, which
leads to the entitlement, which leads to twenty five year
olds still being on their parents' payroll. And that's a problem.

Speaker 2 (28:17):
Yeah, yeah, And it's a trickle effect at this point
because now they're walking out into the real world and
are we fucking preparing them.

Speaker 3 (28:25):
No, we're not preparing them.

Speaker 1 (28:27):
But wait on the record, because I want to put
this caveat many parents are not doing this. I'm talking
in generalizations, and I want to say this nice and slow.
We've been doing it for way longer than we think. Millennials,
gen xers and boomers love to think this is some
new Gen Z phenomenon. It is not true. I am
square in Gen X. I have unlimited loser friends that

(28:48):
were overcoddled by their moms and dads that I grew
up with.

Speaker 2 (28:54):
This is wide open and I'm your host, Ashlyn Harris.
Thanks for listening.

Speaker 3 (28:59):
We'll be right back.

Speaker 2 (29:04):
I want to talk to you about this, because you
and I always talk about the opinions on social media.
And I said this on a podcast not too long ago,
because I know what it was like when I was
younger and I was stealing, and I was doing drugs,
and I was in sixth.

Speaker 3 (29:22):
Grade and I was just.

Speaker 2 (29:25):
Hanging out with the absolute fucking worst people. And I
don't know if it was for attention. I don't know
what the freedom of like being bad and getting in trouble.
But I have said this, and I've said this, and
I've said this, you are a product of the people
you choose to surround yourself with. And every time I

(29:46):
say because this is a lived experience as someone who
was stealing, doing drugs, doing things I'm not proud of
because of the people I was around, because I wanted
to impress them.

Speaker 3 (29:58):
I wanted to fit in. I wanted to be in
bad boys club.

Speaker 2 (30:01):
Yeah, and now I'm in this understanding of I want
to learn. I want to, you know, not be the
smartest one in the group. I want to be challenged
at every fucking turn. I want to be curious, like
I want all these things, so I don't want to
surround myself with people who aren't gonna move me selfishly forward.

Speaker 3 (30:26):
And have a good impact on me.

Speaker 1 (30:29):
And it's because it's because you love yourself more. Now, Yeah,
I mean right, let's get to the fucking let's get
to the fucking fucking point. Yeah right, And this is
what I desperately want. Like I was getting goosebumps as
you were talking, because like my heart was bleeding because
I love you so much. I'm like, man, she was
just in a fucking bad place. When you're in a
bad place, you hang out with bad people because it's

(30:51):
your only safe place. You're thank God, And I'm so
proud of you. You've put it and you've had all
the challenges, many more than I've had per Se, or
different ones than I've had per Se, because I think
everyone's got their own version of challenges. You are in
a place where you love yourself enough to do what
you're doing. And that's what I'm trying to say to
all of you, my friends. Listen to me carefully on
the other side of this podcast. When you're on a treadmill,

(31:13):
bullshitting your workout, or walking your dog, or you're in
the car and traffic, everything is about you versus you
everything in your life is based on where you're at
with yourself one hundred percent. You here's my fee. You know,

(31:35):
you know this probably about me given our friendship, even
though like we're both so busy. But like, I've always
had a lot of girl friends like friends, and everyone's
like girls and guys can't be friends. Like on the record,
I have had many girlfriend I hope some of my
girlfriends don't get offended by this. I've had many girlfriends
that I have had no interest in sleeping with or
hooking up with. I just like people. Right. Growing up,

(31:57):
I always had a lot of girlfriends, first tomboys, right,
because a lot of sports, and especially in college. Is
when I think I woke up to this when my
girlfriends were like, man, and I've been always on this
emotional intelligence shit, long before I understood what the word
meant or even had heard the word. When all my
girlfriends were like man, I just like, I just always

(32:21):
end up with the wrong guys. What's my luck? I
just get all these bad guys and Ash, I'm telling you,
nineteen fucking ninety four, I was like, sister, it's fucking you.
You end up with bad guys because you like you
don't feel great about you, right, you know, like like,

(32:42):
you know, I get the like in a girl's early years,
like the bad boy that's got a pretty face, I
get it, right. But I grew up with so many
other girl friends who never had bad relationships. And the
one thing that was obvious to me as early as
twenty one, twenty nineteen years old, was like, ah, these

(33:03):
girls are like me. They're confident, and these girls are
not the end, right and so, and everybody gets twisted.
Everybody thinks that if you're a pretty girl, you're confident,
and what we all learn as we get older, in fact,
oftentimes you're very much not confident because the only validation
you've been getting from the world is your looks. And

(33:25):
that is fine and good and like, I'm a fan
of beauty, both men and women, but I find many
of my most attractive friends are deeply insecure because they
wanted validation for their brains or for their personality. Rightfully,
So it's a human flight and so yeah, I just
I self esteem is true self esteem. You know, people

(33:49):
get the word self esteem an ego, very confused ego
is actually insecurity with makeup on, and self esteem is
the most intoxicating, powerful superpower on Earth.

Speaker 3 (34:01):
M Yeah, and I think you nail it there, right.

Speaker 2 (34:05):
I think also being a woman and a woman saying
like it is my choice not to fuck with average
people because it affects the way I see myself in
the world and how I move in it. Instead of
that being like a holy shit comment coming from a woman,
a man says that there's no fucking issue.

Speaker 3 (34:25):
There's no issue.

Speaker 1 (34:26):
Yeah, And the thing I always tell my girlfriends is
you'd be surprised though, Like you know, I always say
this the girl house. I'm like, and obviously I have
no naivete. Don't forget. My mom is my hero. So
that made me very aware early on, like, yes, the
world is different to men and women, and by the way,
it cuts both ways. Like I say this all the time,

(34:47):
like when I come back in my next life, I
want to be a ten out of ten women, Like
there is incredible, undeniable, extraordinary life opportunities. God forbid, if
I'm smart, it's fucking over it. I'll take not being smart.
I want to be confident. I want to be confident.

(35:08):
But nonetheless I always say this to girl pals, especially
as we got into this last decade. One of the
sad things that's happening in society is as if we
weren't against each other on religion and country of origin,
as if we needed other things to separate us. We
got into you know this, we didn't. I didn't even

(35:30):
know that I was part of gen X until I
was twenty five years old. M So now we have
generational divide, like, hey, boomers, you have to hate gen
Z and gen Z has to hate boomers. In the
last ten years, the gen Z versus boomers thing and
the men versus women thing has been devastating to me.
It's two new things. As if race wasn't enough and religion,

(35:50):
now let's throw two more things at the world to
divide us. Spy, which I hate, but I tell my
girl pals all the time, like, if you know, especially
in business world, this will make a lot of sense
to you, Gary, if boys are assertive like they're fucking geez,
If I'm sort of, I'm a bitch And there's incredible
historical truth to that. What I would tell the women

(36:12):
listening to this right now, especially the moms of sons.
I said it earlier of how much interaction I've had
with fifteen to twenty five. Over the last fifteen years,
there is no separation between men and women on how

(36:33):
insecure they are. Men. Actually, I'll say nice and slow women.
If you're in a place where you're judging quote unquote
men every single like, let's think about it. I like
razzing on men too. Think about everything you raz on
men for right now. Just think I'm gonna go nice
and slow. Just give it real thought, especially if you

(36:53):
just had a breakup, like I'm sure you're rattling the
many things. Okay, let's do another minute or two. Okay, done.
Every single thing that man does that you think is
horseshit talking down to you, not listening, you know, not
not respecting your opinion. Every whatever you're gonna bring up
right now, one hundred thousand percent of it comes from insecurity. Yep.

(37:16):
Men are uncomfortably insecure. In fact, the rise of like
this man self esteem movement, which is like so sadly
like anti woman, is just exposing even more men that
are deeply insecure and they need some aggressive man to
make them feel more comfortable.

Speaker 2 (37:37):
Can't ye can't regulate emotion because they were never taught.

Speaker 1 (37:41):
To and and just so I would just say, you
know what my great dream is for society that man, woman, black, white, Chinese, American,
all those sub factors became wildly churtuary in the eyes

(38:01):
of people, and we could just get to some weird
we're all humans like, I'm kind of like, I don't
I'm about to lose a lot of the Anybody who
just started to like me is about to hate me.
So I'm just prefacing this. Ash. Do you know that
I have a weird relationship with animals.

Speaker 3 (38:19):
I did not know that.

Speaker 1 (38:21):
Let me tell you what it's based on where I
was going. I wish that humans could blindly love each
other the way we blindly love dogs.

Speaker 3 (38:29):
Oh that's so arh. I feel that.

Speaker 1 (38:32):
I really struggle watching people I know in my life
who are just not great to other people and then
a fucking puppy comes along and they're like like, and
I'm just in. It frustrates the living shit out of me.
And it's how I learned early in my life that
people were scared of other people, that they were insecure

(38:55):
the reason. And you know, I hate to do this
because she's passed, And actually I'm gonna say it as
a implement because I love her deeply, But my grandmother
was a big factor in my life. My grandmother, my
dad's mom, would come to our house and live with
us between my mom's birthday and my dad's birthday. So
she lived in Queens while we lived in Jersey, but
she would come on May third and she would stay

(39:18):
until September tenth every year of my life. So I
really lived with my grandma in a lot of ways.
If you think about that half the year my whole life. Yeah,
she was so negative. She had not one nice thing
to say about anyone, and she spent all her time
trying to put that in me. Like she would actively

(39:42):
go out of her way, like my aunt would visit
her sister in law, and then like the next morning
she would like like I would watch her like a
dog and a bone come to me and like sit
down next to me on breakfast and just talk shit
and about my dad and about my mom and about
you know, those kind of people not to me, about me,

(40:02):
but me to my sister, and my sister to me.
And and then I had my mother, who was literally
the opposite. So I lived this whole life where I
was like, Okay, this is the world, and like this
is way better than this. And obviously I shared my
mom's DNA, so it made it natural for me. But
my sister shared my grandma and dad's DNA and it

(40:22):
made it harder for her m. So obviously I had
that framework. So I saw the world that way. Everybody
I met was either my grandma or my mom and
my grandma's crew. Oh, they love a good dog, m
h always. Because a dog doesn't talk back to you, period, yep.

(40:43):
But a human can call you out on your insecurities.
And if you're deeply struggling with narcissism or insecurity, well
you don't want people poking.

Speaker 2 (40:55):
Yours and you don't receive it period. That is life,
and it's beautifully put. And I'm curious, Gary, for someone
who's lived so loud publicly.

Speaker 3 (41:06):
What do you? What do you keep for yourself? Like,
what do you what anchors you?

Speaker 1 (41:11):
That's good? My family, you know this. I'm uncomfortably private
mm hmm, deeply private. Nobody knows shit about my personal life.
The end.

Speaker 3 (41:24):
I love that because you give so much.

Speaker 2 (41:26):
You give so much to everyone and the way you
show up and you're such an impath and like, I
just imagine absorbing that all fucking day. I know this
is your vessel and your gift which has made you
incredibly a good human and family man. But I'm just like,
how the fuck do you keep going?

Speaker 3 (41:45):
Gary?

Speaker 2 (41:46):
How do you keep waking up and choosing it over
and over and over again.

Speaker 1 (41:51):
It's like profound, It's it's no different than all the
skills we all have, Like this is who I am.
I have so much to get ash. I've been full
from the get, you know, like I've been this. You know.
I always love when people like okay, Gary, but that's
because now rich or famous, whatever they want to throw

(42:12):
at it. And I love with my ogs, like literally
people that I knew in third grade, ninth grade. Sometimes
people haven't talked to in twenty years. I've seen in
the comments being like, nah, this motherfucker like was breaking
up fights in fourth grade, stuck up for the nerd
like like he just like, I've been full from the get.
This is why I give so many flowers to my
mother I was and my father. You know, it's actually fuck,

(42:34):
it's my dad's birthday today, Happy seventy second birthday to
Sasha Vaynerchuff.

Speaker 3 (42:38):
My father birthday.

Speaker 1 (42:40):
In fact, in fact, the lesson. In fact, actually, let
me give him a huge flower as a parting shot.
In fact, my mother is also so not candorous. My
father is incredibly candorous, very honest, And because I started
working with him at fourteen and worked with him full

(43:03):
time from twenty two to thirty four, I would argue,
I'm a much better version of candor than my mother
my father. In fact, let me say something even more profound,
I believe if I had a different father who was
not such an honest man and who hated bullshit, who
hated exaggeration, let alone lying that ash. It is not

(43:27):
lost on me that sometimes when people see me for
the first time, they're like, wait a minute, who's this slickster? Yea?
And I would argue that if I did not have
the father that I had, I might have been the
bad version of who People who want to think I'm
bad like think like I think, my I think at fourteen,

(43:47):
I was so scared of my dad because he's a
scary fucking individual in a lot of ways. I think
he fucking scared the bullshit out of my body. I'm
being dead serious, And what I was left with was
all the charisma, like it's real, I really think about this.
I'm like, h because you know this, like anyone who
is overtly charismatic gifted verbally like you can get into

(44:09):
a very dark place.

Speaker 3 (44:10):
Mm hmm.

Speaker 1 (44:12):
Absolutely, And there's levels to it, right, and I would
say that it is Actually I'm going to be very
real about this. It is very clear to me that
I'm a much better man because of my father than
what I would have been without him, and it and
it might have been that final piece of the puzzle

(44:34):
that m It's almost like my mom built the Sunday,
but my dad put that cherry on top that I
think has led to all of my happiness and success.
And I'm incredibly grateful for my parents. And how do
I get up in the morning.

Speaker 3 (44:51):
I'm built for this, fucking built for it.

Speaker 1 (44:54):
You know I can handle it because to your point,
when you're strong, you can deal with the bad. I
can with the judgment, I can deal with the cynicism.
I can deal with people spreading when when your public
figure people just make I mean, you're you've you know
one thing that I think has helped me that has
not been your path is because I've always kept all

(45:16):
of my personal life private. When people make up stories
about me in my professional life. It stings, but it
doesn't mean anything. The reason I'm empathetic to you and
other people who do have their relationships and their life
much more public. When people make up shit about you
and your partners and your children. Fuck man, that's hard. Deep. Yeah,

(45:40):
it's deep. And so I think both I was built
for it and two and my ex wife because there's
a lot of credit for this because we were very
aligned to this. I think the strategy of like my
personal life is going to be for me forever and never,
no matter if I'm the most known person on earth,
which I continue to be and aspire to be, because
I think I can leave a positive impact, I still

(46:02):
will not give the world my personal life. Mm hmmm.

Speaker 2 (46:05):
I love that and I respect that about you and
I appreciate it. And Gary, thank you for showing up
the way you do with fucking fire and honesty and
just the constant reminder that dreaming big.

Speaker 3 (46:20):
Isn't just allowed, it's it's necessary, and I think.

Speaker 1 (46:23):
And it's hard, and it's hard. I want I want
to leave with this, If you have big dreams, back
to something you touched on here, If you have big dreams,
you need to go to the gym without your podcast,
without your cute little outfit, without it being for anybody
but yourself, and you need to fucking work in there.

Speaker 2 (46:41):
Be comfortable with being uncomfortable, is what you said. Be
fucking comfortable with being uncomfortable, and you want.

Speaker 3 (46:49):
It if you want it.

Speaker 2 (46:51):
But I think that's the takeaway here from you is that,
like success isn't just about business wins, it's really about
how you live, how you give, how you show up
even when it's fucking hard.

Speaker 1 (47:02):
Just like you said, I would actually tell you, Ash
as you continue to get to know me better than
you might have started to already sniff this out. This
is the wildest fucking thing about me. I'm overtly passionate
about my career, about what I do, about how I
try to show up in the world. Everything we just
talked about for the last hour, and none of my
validation comes from it. It's not what I strive for.

(47:27):
I strive for waking up in the morning and not
having pressure on my chest piece peace of mind, and
I have it so.

Speaker 3 (47:37):
Heavy, ah, I love that.

Speaker 1 (47:39):
So heavy, and that's what I want for everyone else
because it's so much better than the alternative.

Speaker 2 (47:44):
Oh my gosh, it really is. And I'm just getting
a sniff at that at thirty nine.

Speaker 1 (47:49):
Good for you. Well, listen that you're a fucking baby, honestly, honestly,
you're gonna live for another sixty fucking years. Thirty nine
is an incredibly good age to get a sniff, and
I want you to keep fucking going down that path.
It's better than all of the empire building you can do.
The Empire of peace of mind is better than the
Empire of bank account.

Speaker 3 (48:09):
Couldn't agree more.

Speaker 2 (48:10):
All right, Thanks, love you, Gary, thanks for coming on,
Love you so much.

Speaker 3 (48:14):
Okay, Bye.

Speaker 2 (48:19):
Wide Open with Ashlin Harris is an iHeart women's sports production.

Speaker 3 (48:24):
You can find us on.

Speaker 2 (48:24):
The iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
Our producers are Carmen Borca Correo, Emily Maronov, and Lucy Jones.
Production assistants from Malia Aguidello. Our executive producers are Jesse Katz,
Jenny Kaplan and Emily Rudder. Our editors are Jenny Kaplan

(48:47):
and Emily Rudder and I'm your host, Ashlin Harris
Advertise With Us

Host

Ashlyn Harris

Ashlyn Harris

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