(lively guitar music) – Hey GaryVee, hey Wyclef,
how are you guys doing? Thank you very much
for taking my question. My name is Brian Ripps. I’m a musician and
entertainer from New York City. For the last 10 years I’ve been
making my living writing songs and traveling the country
playing for the people. One of the biggest lessons I’ve
learned is how to take no for an answer and press on. I’m curious to hear from both
of you what some of the biggest no’s that you been encountereed
in your career are and how you overcame them and
moved on to conquer them? – Great question.
– Oh that’s good. – It’s very nice.
That was well done. – Great guitar player, too. – You know how happy
that guy is right now? – [India] So happy.
(laughter) – You killing that guitar.
He’s in New York? – [India] I’m not sure.
– Yeah, I think he said. Yeah. – Yo, do me a favor
right now man– – This is big. – hit me at okay we’re
gonna do, let’s make this big. (laughter) – Now you gotta deal with this. They have to deal with
this with me all the time. I love it. Do it, do it big. – Let’s do this.
– Go ahead. – When you come see me–
– In Jersey. – We come chill, don’t worry
I’mma have grass and everything. – No worries.
– You bring the wine. – I’m bringing the wine. – So listen, why don’t
we bring the homey in? – Done.
– Let’s bring him in. Let’s when Brian in and we
could do a little jam session. Okay, that’d be cool.
So this is what I’m thinking– – Dreams are made on
The #AskGaryVee Show. – To his question I would say the no factor is a
motivation factor. And the thing about it it’s
goes back to what you said. Every day you constantly
have to prove yourself. – [Gary] Only as good
as your last at-bat. – You’re proving
yourself to yourself. Always remember that because
the day that you wake up and you say, “Man, I’m
already good on piano. “I’m already good on guitar. “I done wrote 50 songs. “I don’t need
to write anymore.” That’s the day you’re finished.
– [Gary] Finished. – Because the thing that keeps us as human beings going is creativity. The day that we lose that we
completely lose ourselves. So to your point is it’s just
about each one, teach one and constantly being inspired and
whenever somebody told me no it was always a motivation for yes. – I couldn’t agree more. Again, so many of
you watch my content. Only as good as
your last at-bat. Chip on the shoulder. I would say that I’m wired, I’m
curious, I’m surprised how much I do want, I like
sticking it to the market. I’m very competitive. Do you find
yourself competitive? – You have to be.
Naturally. – To me I’ve talked a lot
about loving to lose. I do. For some reason, Staphon,
you know this when we play basketball in the morning,
when I lose I’m like weird. I like it. There’s a feeling
that I want. It motivates me so much. I truly believe that the thing
that separates so many people is people are scared of
the no and the loss. They think it’s a scarlet letter and what that does
it makes them not go. I love the way
that he said, “When I get no’s I
push through.” For me, my early childhood to
answer you directly because two guys that like to philosophize. I’ll go right into it, my
early childhood was probably my biggest adversity. I didn’t have the same adversity
of being a minority or gender or things of that nature. I didn’t have a whole lot of
money but the big thing that I had I was getting Ds and Fs. So I was making $3,000 a weekend
selling baseball cards in the malls of New Jersey but I was
getting D’s and F’s is a 13, 14-year-old and
everybody thought I was a loser. My teachers, my friends’
parents because that’s when school was the game.
– Mhmmm. – And so for me the market, the
world was telling me I wasn’t good and everything inside of me
told me I was going to be good. I don’t think you can be when
unless you love yourself first. I think you’re right about it
being a one-on-one game inside your own dome. So for me my adversity was
early on because once I hit the market, once my entrepreneurial
flair came out my first year running my dad’s
business I grew substantially. It was over before it started. Adversity, I think the thing
that is most interesting to me if this company doesn’t do
well next year, if my next five investments don’t do well,
if my next prediction is that Blah-Blah-Blah’s going to be
huge and it isn’t when then I’m not as good anymore. I’m fascinated by
the music industry. Three, four good albums
in a row, iconic stuff, one bad album.
It’s amazing. You’re just as good
as your last at-bat. – That’s right.
Think about it. In our business
we say 10 million is a championship ring, right?
– [Gary] Okay. – So to be able to
sell 10 million a few times and to do it for different people, right?
– [Gary] Yes. – Not yourself.
– [Gary] Yes. – Because this is another thing. Okay, cool, you can
make money but can you make
other people money? Because the key is if you can
make other people money, you create social entrepreneurship.
– [Gary] That’s right. Scale. – That’s right. So for me that’s
definitely part of, so for me and my business I remember I did the, when we
did “The Score” I got scared after we sold 10 million.
– It’s crazy, right? – ‘Cause I said, no
disrespect to Menudo. But I’m not dissing you. I love Menudo and
New Kids on the Block. I love them
’cause they watching. I love them. But I was like, “Holy shit,
we’re a pop group now.” – Yep. – I disappeared man. Got an apartment on
66th street and third and I was in a small room. And I was like, “I have this
thing called ‘The Carnival,'” and I was like, “I have
to do this thing.” – Now.
– And I was like, “It’s artsy, it’s artsy.
I have to do this thing,” and from there that landed me Destiny Child,
Beyoncé and them. Right? Somebody was like,
“Yo, we love ‘The Carnival’. “There’s these four girls in the
hotel room and we need you to “just go see them.” And then I went to this hotel. – Let me ask you a
question about the hotel room? Was that a moment where you just
understand immediately, did you under immediately understand
Beyoncé had real big-time talent or did that develop? Just for you one-man,
I’m just curious. Storytime. – I think for me I have a knack. Like Lauren as a kid 14, 15. – She’s from Maplewood? – Yeah,
Maplewood, New Jersey. – Right there.
– Columbia. Right. So I get this gift
from the church though. It’s purely and the church
called me the choir director. I can find a singer
in two minutes. I’m like, “Well, this is the
singer that’s gonna sing lead.” So definitely when I first
saw Beyoncé I was like wow. Right?
– Mhmmm. – What do I remember
about Beyoncé the most? I’ll tell you. And she’s watching, she know. – Thanks for watching, B. – Yeah. Every, every and
this is taking me back, right? Destiny’s Child was
opening up for me. – Is that right?
– Right? Watch this. But every time Destiny’s Child
got off the stage and I went on Beyoncé was
always on the side– – Watching.
– studying the show. People be like, “Man why
is she so invincible?” She’s so invincible because she’s a student of the game. – She put in the work.
– Right? This is another thing
when we talk about, right? So for me when I show up
it’s not about what I’m doing. I want to know
what you doing. Right? – It’s actually, what I do
for living is actually only predicated on watching what
other people are doing to figure out what they’re
going to do next. You know, I’m going to stick
here and be selfish for a second because it’s the
thing I like the most. Just binary, who, one man’s
opinion, you’re just one man– – Yeah. – Who was the most talented
person you came across and who was the hardest working
person you’ve come across? Right now, so far, in your
journeys, in your industry, in your industry.
– So far, right? – Yeah, just so far.
I’m just real curious. And I know like I’m sure is not
what you think about everyday and it might not come that easy. As you debate it for me– – For me it’s a
set up question– – Okay. – Because I know Carlos
Santana watching this right now. – Of course.
Carlos, thank you. (laughter) – We have a lot of
people to tweet. – You’re setting
me up right now. But I could, you know,
it’s just like Santana’s like,
“You better say me.” (laughter) You put me on the spot. – I know I’m putting
you on the spot. – It’s cool, it’s cool.
But it’s a good spot. – But I’m curious.
You don’t have to answer but I’m really curious and I actually I really want to know
hard work, I want the hard work one to be honest with you. – Everyone’s gonna
respect this answer. – Okay. Go ahead. – For me, the hardest working person that I’ve came across in my entire life so far will have to be
Michael Jackson. – Hmmm. – Because and this is
why tell you, right? So when you’re hard working
your like moving at the speed of light but somehow you’re aware
of everything going on with the culture and everything. You know everything
at real-time. ‘Cause you Michael, man. You’re like in Asia somewhere
so why are you calling me. And then you’re like, “Yo,
I was just watching this TV.” He’s like, “Who’s this guy?
Gone to November.” I think I am being pranked
and I hang up the phone. The first time.
Michael calls back. I’m like, “Holy shit, this
fucking Michael Jackson.” This guy is scheduled literally
shows every, every day somehow finds time to
land at Sony studio, come up the elevator, come see me sit down and
that whole day changed my life. Ever since that I just see
music totally different on the perception because I’m like,
“Yo, this Michael Jackson and he’s sitting there normally,”
and he’s giving me the rhythms. While he’s sitting there and I
know the dude is coming from, the flight has to be super long. And he’s in there and he’s like, “No, this is how I’m
hearing the bass. “This is how I’m
hearing the drums.” I’m hearing his whole body. And I’m like, “Yo.
That’s freaking Michael.” (laughter) – Dude when I’m telling you
I’m tripping, I’m tripping. So for me, I would say the
coolest, the coolest thing about Michael, man so then we in the
room with two of us and he’s like, “Man, you know your style reminds me
of when we were younger they took us to Jamaica there
was a guy he used to smoke a lot of weed.” (laughter) “Bob Marley?”
He was like, “No, no, no.” I said “Oh, Peter Tosh,”
and he’s like, “Yeah.” (laughter) – That’s unbelievable. – So for me that to me– – Was huge.
– It was huge. And then I was amazed by the
short time that I spent with Whitney Houston.
– Yes. – She was insanely incredible.
Jersey. – Yep.
– Jersey crew. And, man, Whitney’s
work ethics was crazy. I guess I was lucky because when
Clive Davis calls you and he’s like, “Yo, man, I need a
song for Whitney Houston.” – Yeah. – You start trembling, right? And then Whitney shows up. I’m like I know Whitney. I know your schedule and
what you’re going through. Show up on 24/7. – Ready to work?
– Insane. Like it’s the first record
they’re being recorded. And then you pinching
yourself you like, “No, no. That’s really Whitney.
‘The Bodyguard’,” and then she showing
up as if this is the first record she’s
about to record. – Because money and success
doesn’t change you, it exposes you.
– Facts. – It’s just so real. India?
– Bars. – [India] The last question was,
“Who do you think the greatest

– [Man] Yo!
– [Gary] What up? – [Man] Gary, this is
Josh Easton, how are you? – Good Josh. How are you?
– [Josh] Pretty good. Hey man, I just noticed you’re
wrapping up your show so do you still have time for a question? – I’m not wrapping up,
I’m finished. – [Josh] You’re finished. – But I got good news I’m gonna
sneak in this question for you. So?
– [Josh] Alright. – What is it? Fast! This has to be the fastest
question and answer all time. Go! – I own two businesses,
I’ll keep it brief. When do you decide if you
start a business, I have two right now. One of them have dropped
passion in my partners don’t really have there
drive to keep going on. – Yep. – [Josh] At what point do you
decide to throw in the towel and how exactly have you ever had
any situation where you found yourself–
– Yeah. Yeah, I’ve been in a lot of
businesses where I was the minority partner non-driver of
the business that have failed. And the way I do it is I just
take it for a loss and I chalk it up. You try to sell it for whatever
scraps it’s worth or sell it back to your partners
that are running it or you just walk away. It is a zero. It’s over.
It’s done. Or if you feel like crap but
I work seven years it’s worth real money, you sell it. And you sell it from a
non-leveraged position which means you get less money for
it but it’s still okay because clearly by the tone of your
voice and the fact that you know passion for number
one you got to let go. – [Josh] You work 90 hours a
week and it gets tough to spread it between two places making sure
your time is in the right place. – Yeah. The real question is how
much money are you going to lose and are you willing to lose it? A lot of times what people don’t
realize they don’t lose the $40,000 or $5000 or $500 million
and they can make 700 million or 5000 times if you get back your
40 hours from that thing or 30 or 20 or even 10 you might make
more money deploying against a thing you care about the
money you left on the table. So XYZ you’re leaving hundred
thousand that you’re giving up and you’re like shit I
can’t give that up but we don’t realize of the 18 hour backs and
happiness and not the drain and emotional drain of the hundred
hours a week on the other thing allows you to make
120,000 on your new gig. – [Josh] Yeah, that’s
exactly where I’m at. How much more money can
I make of another business if I designate more time to it? – You know the answer.
You know the answer. – [Josh] Yeah, yeah, no
it’s totally clear now. Never start businesses
with friends with either. – No. Not true. Always start businesses with
friends if you can pull it off. – [Josh] Get everything in writing. Listen it didn’t work out.
It’s a life lesson, right? But, you know, that’s
the fucking game baby. This is entrepreneurship. – [Josh] Yeah, I know.
– What? It is India. – [India] No! It’s the beeps!
– Oh, the beeps funny to you. Alright I got to
go bro, I love you. – [Josh] Alright, thanks man.
– See ya. – [DRock] Here, your phone. – [Phone] Call from unknown caller.
To accept press one.

– [Chase] My friends and I
are starting a creative agency. – Good. I think I know thing
or two about that. – And so while we work and
read a lot of your stuff we’re trying to get all of our
ducks in a row before we start. We launch August 1st. How do you think the best way
for us to get over the fear of failing at this?
It’s kinda taking a leap. We’re currently in-house
marketing department for 21 chain retail store. – I think you guys, if you guys
are taking the leap, you guys are rounding the troops and saying
screw this place we’re going to do our thing you’ve got to first
decide here the ways to do it you do the emotional and
practical when you take a leap. The practical is how
many of you are doing it? – [Chase] Three. – The three of you have to
figure out worst-case scenario nothing goes well how long can
you survive on your savings or you’re willing to be
entrepreneurial ghetto. Got it?
– [Chase] Yeah, got it. – So the three of you need
to sit in a circle and you go India, how long can you last?
And India says 18 months long. Andrew how long can you last?
Four months. Andy how long can you last? Two years. We know we’re only as
a strong as our weakest link. God damn Andrew’s only
got four months so we have to talk about that. Number one do you think that the
three of you can go without any sales for a year? – [Chase] Yeah. The good thing is that we have
investors from the company that got behind us and they’re like
we kind of have a safety net in a little bit if it fails. – So great. So it sounds like you created the
practical version and you just have to make the
emotional version. Too many people and you know
I’ve been talking about this fake entrepreneurship. If you’re scared to make
the jump you still have entrepreneurial tendencies. You’re not an entrepreneur yet. It’s why you worked at a
company in the first place. You just got to
make the jump or not. It’s like swimming. You either jump in the
pool and you go or you don’t. The end. – [Chase] Yeah, definitely. And that’s my fear and when
you’re starting this its new frontier you know– – Dude, don’t be scared
nothing’s gonna happen. You can always go back
to the god damn job. – [Chase] Yeah. – What’s gonna happen? People are gonna make fun of you? Your mom’s gonna say you failed?
Who gives a shit. Go try it, doesn’t
work it and you go. Don’t care what other
people think, it’s the only reason
that you’re scared. – [Chase] Yep. – Whether it is your spouse,
your partner, your child, your mother, whoever it is eliminate those voices,
listen to yourself and know that if you fail you
go back into it and nothing bad will happen but if you win
it’s the greatest shit that ever happened. – [Chase] Hell yeah.
Awesome. – Cool. Alright brother,
see you. – [Chase] Thanks man.
– You’re welcome. So why are calls coming through
I’m on the line but then not?

“Gary, have you ever dropped the ball “on making a decision
due to over thinking it?” – Chris I would say that my… I almost need her to repeat
it, but I think I got it. Actually I sent it to her so I got it. I got it. The reason I sent it to India, was I say this Chris in the feed, is I’m actually normally making mistakes in the other direction. So I tend not to overthink
at all, I’m very intuitive, and most of my business mistakes have been to act too quickly
and then have to bail out. I have found that speed trumps everything, and so for me when I
weigh opportunity costs, I’d rather start something both money and time if
I intuitively feel it and then let it fail six
months or a year later. New concepts I have for
Vayner, new divisions, new types of wine’s for Wine Library, things I’ve done for my own brand and I wanna push so many of you for this I really wanna push a lot of you. So many of you are not taking action because you overthink it, you
overthink it, you overthink it I always say deploy your resources that you can afford to lose. A lot of you don’t have the dollars, I used to not have the dollars, but I had my time. The reason I punted at my twenties is because I didn’t have money, or I didn’t have a lot of it. You know a lot of you hear about the three
million dollar business, I love when people try to rag on me and say oh if everybody had a
three million dollar business I mean every single kid that gets 500,000 dollars in startup which was millions have more
dollar resources than I had. We didn’t have dollars, the business did three million dollars, it made 300,000 dollars in profit in selling three million
dollars worth of liqour and then it still had to pay expenses. My dad took home his salary, like we had no money. But I had my time, and I would test things, and I stayed up. I didn’t punt my twenties
for kicks and giggles, I pumped them because the only
resource I had was my time, and so I had to work 18 hours a day because that’s what I had. Got it? So taking action, especially
if it doesn’t cost you money and it’s just time is
always a better answer than pondering or thinking or trying to decide if this is gonna work, you don’t know. The learning of the failure is as equal to the victory of it. The thing’s I’ve learned in my 20 years, the reason I’m so advanced
as a business person in my own mind is not
only have I worked a lot, but this work hard work
smart thing I’ve worked smart and one of the smartest things I do as an entrepreneur and a business person is I do things so I can understand
whether they work or not. You can’t just sit here and say “Is this going to work or not?” Debate it your whole life, never do it, and then not know the answer. Like no. One of two great things happen, one you did it and it worked and you made money and you won and you got accolades and it worked Wine Library TV, it worked. The classes I was gonna do, I’m trying to think of things that failed another thing is that I
just forget them so quickly. I’ll work on this, you know India I wanna do top 11 things I did on Wine Library that didn’t work. Local van delivery,
at scale I never did. So one of two things happen, either it works and you make money the email service it worked, or it doesn’t and you’re like well I’m not gonna do that again. This whole indecisiveness
when you can do it, if you don’t have the
money you can’t do it so what the fuck are you
thinking about it for? “You know I wonder if I buy
a building in New York City will it go up in value? I wonder.” The answer is it’s gonna work, but guess what I don’t have
400 million dollars liqiud to buy the fucking Empire State Building, type of building because
you can’t even buy that for 400 million. This is an interesting question, the answer is no, I’ve never failed because
of indecisiveness. I’ve only failed because I’ve done stuff, but I’d argue that I didn’t
really fail I learned, I might have micro failed but I macro won. – [Voiceover] J Scot asks, “Gary do you expect your own
employees to work like you do?

– [Voiceover] Meet asks, “Hi, Gary, “it seems like everyone speaks about “not giving up no matter what, “but how do you know when
it’s time to let it go?” – So, I’m, this is
something I struggle with, like, having a loss on
your resume is so scary, and the business ventures that I’ve had in the past where I
wasn’t actively running and I’ve talked about Cork’d or Forrst. Lindsay and Kyle, amazing entrepreneurs that I don’t feel that I supported enough and thus those two, Obsessed
TV with Samantha Ettus, where I try to produce a video show, that didn’t start me. I never was able to give it enough energy, and the thing I spent
the most time with is when do I let it go? Because there’s a point where you realize, by the way, I realize this with employees, you know, I know a lot
of VaynerMedia employees watch this, but I’m gonna tell the truth. There’s 5 to 6 employees that I think it might be time to not
work together anymore, and do I struggle with that? Boy, do I struggle with that. One, mainly because I don’t
like letting other people down more than anything. The truth is, Meet, I think
this is a very personal answer. I think it depends on every individual, but what I will say is, way
too many people watching this right now are holding onto
hope, or a non-reality, or don’t wanna make somebody feel bad, or dont wanna have the
reputation of having a loss on their record, and I
think that’s a huge mistake, and it’s probably the mistake
I’m most vulnerable to, and as I think about my next 40 years of executing, and you’re right, I am hustling more than ever, I’m feeling more fit and energized and feel like I’m gonna really
go into my golden years, especially the next 20
years, that’s just the truth, though I’m sure when I’m 60 I’m like, this is when I’m really gonna do it. I do think that that, this
is a tremendous question, I’m so goddamn pumped that this happened on my 40th, post-40th
birthday episode, first one. This is the one thing that
I’m spending a lot of time on. I think it’s hard, but it is, I think more people have
to let go more often. And the two things that I’m working on are both ends of that:
saying no more often, because boy that’s hard for me, and then letting go more
often, and really zoning in on that middle is my answer to that. So the punchline is, very personal, but, because I wanna bring value
to everybody listening, what’s up, podcasters, and watching, I really think that a lot of
you need to take this question, use it as a moment, use it as permission, let me be your olive branch, link to this part of
the show as the excuse or the frame that let you do it, there’s a lot of people
that need to let go. – And if I could have one thing, that would be, this book is probably the
first time where I felt like I was gonna fail in a while. – Interesting, because you, because you had to do the work? It wasn’t like what naturally was in you. – Right, it was, what was naturally in me was just write another book, you know, and I thought that I would
be letting everyone down by doing that, and in three
and a half years in the making, right, there were, I mean,
even up until six weeks before it was done, I thought
it was not gonna happen. – Meaning what? – Just, so many things
were going wrong, you know, in terms of production
and printing processes and finding the right shapes
and everything about it. Also, re-learning how to write sentences. Like, I was beaten. And there was a saying
that a friend of mine, Adele Ressie, had told me that, an entrepreneurship,
it’s always the darkest before the dawn. And I thought that, yo, maybe that is it, maybe this was just a test
to go a little bit further and see it through, but at the same time, it was the right thing to do, but at the same time, there are moments when you have to walk away, and just try to learn from them, because that’s all anybody wants from you is to show that you tried
and that you learned from something and that you did it better or did it differently the next time. – Appreciate it, my friend. As the guest of today’s show,

“how do you not take defeat personally?” – When you’re giving 100%? Staphon, give me a 100 moji right here, ’cause you know I love that. We’ll see what you do with that. When giving 100%, how is it possible to not take defeat personally? – Yes. – Uh, no. Meaning, I always take defeat personally. I always give 100%, but when giving 110%, defeat should be personal. If you do not take defeat personally, then you’re a non-winning player. Sorry to get very realistic
here this morning. If you are not pissed
every single time you lose, and I mean Parcheesi, I
mean Madden, I mean in work, I mean when you don’t
even control the outcome, a.k.a. what I’m gonna deal
with if and when the Jets lose tonight, when something
I can’t even control, because I’m gonna give 100 as a fan, I’m gonna start fighting and being nasty to the Bills fans that
I see on the way out. I want to get nasty, I want
to make them uncomfortable, and I take it extremely personal. I really believe that
struggling with defeat, being a sore loser is an
absolute proxy to success. It means you care, and
when you care, you fight. The reason I think I will
always be great at business is I’d literally want
to die instead of fail. Die, death, over. I do not know how to live in life. with an L in business on my resume. I may have micro-Ls, but the ultimate L. You know that joke I
make of, secretly I want to lose everything to rise like a phoenix? I don’t even know, yes, but boy, I’m not even sure I’m
gonna get that chance because I wouldn’t even know how to function in society with that loss. That’s how much I care, and so you should take defeat personally, period. – [Voiceover] Jared asks,
“Do you think Starbucks

“Just lost one and I’m mad as hell.” – Yeah, mad as hell is good. I think mad as hell is appropriate. When I lose a client, the
first thing that I think about is what did I do wrong? And then, most of the
time I have an answer. If I don’t have an answer,
I try to figure it out. But, I’m pretty interesting when it comes to losing a client. I’m very much onto the next one. I on the other hand am very lucky. Listening to you is really interesting. I was sitting here and saying my god, my ability to dump and
move on in any situation, relationships, business,
it’s the game for me. It’s why I’m always in a good mood. I literally sit on bad news and bad stuff for fractions of seconds. DRock’s shaking his head, right? – What about with intimate
or personal relationships, with friends or family? Now do you just say screw you,
I’m off to the next person? – I haven’t really lost
anybody who I would call in my most inner circle. I’ve had relationships
that have, like, my longest girlfriend relationships
that ended were predicated on me sitting on it longer than, it was in my head for a long time anyway. So, yeah, I mean, I don’t know. I’ve been very blessed that
somebody that meant the world to me hasn’t decided to leave me. So that’s one part of it. And, the other part is, I haven’t, outside of a couple long-term girlfriend relationships, I
haven’t parted from anything that’s been in my inner core. In business, I’ve had to fire
people I care a lot about. But, I’ve come to a
place where I recognize that I was doing more
harm by keeping them here and giving them no growth
here, Wine Library. So, yeah, that’s that.

“you were wrong and how did you handle it?” – Kyle this is a great
question damn it Stunwin. I’m wrong a lot. I don’t talk about being wrong a lot because here’s the secret weapon. Guys it’s taken 141 episodes to get to the secret weapon. Stunwin the secret weapon
to why I am the way I am. Staphon I need massive
graphics right now. Give me some like rockets coming up here. Secret weapon (whistles)
(rocket engines roaring) I am wrong so much it’s kind of scary. But for some unknown reason, I haven’t fully quantified
this, I’m not capable of giving it much thought and actually spend zero
time post gaming it. I don’t microanalyze for hours, days, weeks, months, years and this is for some of
you out there, lives. For your whole life, you’re microanalyzing why you made that mistake. You know here’s a good mistake. I passed on Uber’s angel round
and left 200 million dollars cold hard cash out of my pocket in a world where my game is being a business man. I would argue that my biggest mistake is disproportionately bigger
than any of my victories. I just don’t you know, I’m
just not crippled by it. I have friends who passed on things and they just can’t ever
get over it, get over it. So, what was my last mistake? I probably made one in my last meeting. I’m probably making one right now. I make tons of wrong hires,
I say things that don’t sell in a meeting, I make bad investments, I make wrong strategies. I started four massive initiatives for VaynerMedia this year,
two crush, two are failing. Like, I mean, I you know, I make mistakes all day. I just don’t respect my mistakes. – [Voiceover] Best wine club asks,

“Where does confidence come from? “How do you both work on it?” – That’s tough. – I’ll let you go first here. (laughs) – Confidence, I mean– – Hold on. – [Voiceover] That’s awesome. – Yeah, I couldn’t (laughs) – You didn’t know the address? – Gary, over your left shoulder
is my electric skateboard. Right there.
– Yes. – I rode that electric skateboard up here. And if there’s one thing you
don’t wanna do while traveling 24 miles an hour in heavy
traffic through New York City, on an electric skateboard
is to whip out your phone and double check an address. – Respect. – So you gotta write that down. – Respect. All right, answer Ben’s question
about your outrageous level How does one have enough
confidence to ride an electronic skateboard 24
miles an hour in New York City? – I have an answer that’s
not really a great one for people to hear, so I’m hoping you have a better answer than I do, Gary. My answer goes like this, I’m one of four kids. There was the first born. The only daughter. And the baby. And then there’s the
forgotten child, Casey. So in my household, it
was like fight to survive. And my confidence was like born into me out of need to just exist
and be noticed and be fed. Now, not everyone has had
the beautiful misfortune that yielded the fortune of my childhood that turned me into a confident person. But I think it’s very
different from someone who finds themselves, as an
adult, in a world that sort of thrives on those who have confidence and being forced to find
that within yourself. But one shortcut I found to
that is making something. Making anything. Whether that’s writing something, whether it’s something creative, whether it’s something more pragmatic. Whether that’s a relationship, whether that’s a friendship. If you generate something
you can take sort of, you take comfort in what
it is that you’ve just made in your yield and I think
that’s a really great shortcut to finding confidence. – Casey, answer– Give me a word association
play really quick here. Fear. – Illness. – Illness? – Yeah, that’s– – I really didn’t want you to go there. Thanks for screwing up my answer. (laughs) For me– – The only thing, being
sick is the only thing that I’m scared of. – By the way,
that’s really funny. Actually, that’s really interesting. Because I was dissing a little bit and now I’m gonna put you on a pedestal. It is literally the health and
well-being of the people I– Weirdly, for me, it’s the people I love is scary ass crap for me. It’s a very big challenge and we all go through it. And so, I’m with you on that. Where I was going with that, is this, I am not scared to fail, by any stretch of the imagination. And it comes in the form of
truly being in this weird place where I really don’t give a
rat’s ass what anybody thinks. And again, that’s wiring. How does one work on that? What do you think I sit– What do you think I go in my room like, “Don’t care what anybody thinks. Don’t care what anybody–” (laughs) Like, you don’t do that. – Yeah, you get made fun
of a lot in high school and it seems like the entire
world is falling apart because you’re being picked on. – I want people to make fun of me. – You grow up and it
realize it doesn’t matter what other people think. – I do, India.
– You really don’t. It really doesn’t. And appreciating that– – It’s like those last
two weeks of high school. If you can capture that feeling. – Those last two weeks in high school, literally, everybody stops
caring what anybody thinks ’cause you’re all going somewhere else. And so, I’ve always had that feeling. It’s crazy how, you know, I was born with confidence,
I truly believe that. I do believe, in my case, I
also have the fortunate aspects of coming from a struggle
place, in a different way. On the flip side, my mom,
I was the first born. The apple of my mom’s eye. And so I had massive
positive reinforcement which then just made me
feel entitled to success. In an environment where
I was failing classes. I was 4 foot 11 when I went into my freshman year of high school. Not so strong…
– Rough, rough. -of a situation.
(laughs) But I walked out– I mean my book bag was bigger. Where’s you big book bag? – Didn’t bring it today,
not on the skateboard, Gary. – Like, I literally– My book bag was like your size. Let me tell you story
about my freshman year. Ninth day of school, I’m
walking down the hallway. I’m late for a class. I have a Jordache book bag (laughs) that’s twice the size of me. I’m walking. It’s like eight minutes
after the bell rang, I’m lost as fuck ’cause we have huge high school,
I have do idea where I am. This is terrible, right. There’s some dude, hanging out of class with Paige Parlow who was one of the hottest
girls in our school. It eight days into
school, I know who she is. She’s a sophomore, he’s a senior. I’m walking by them. He goes, “Psst.” I go, (beep). I go, “Yeah.” He goes, “The nursery
school’s over there.” That’s what happened to me. Do you know what I went through, what went through my mind? I said, wait till (beep)
(beep) (beep) face, punk. (laughs) Sorry, India. That’s what went through my mind. And that’s just where
I’ve always been. (laughs) I know it was a little crude. – Gary Vaynerchuk, folks. (laugh) – All right, let’s move on. (laughs) – [India] From Allen.

– What has been the
largest or biggest failure you’ve had either in
your business or in life, that’s propelled you forward
towards the most success? Also, I hope to see you next week as I film the #GaryVeeShow with you. Thanks. – That’s a great job, Aaron. Sorry you lost. Great question, love the video. You know I think, you
know, I’ve been lucky. I think the one failure I’ve had was that 2009 to 2011 window
where I was trying to be Gary Vee, ’cause of Crush It!. I was running Wine Library. We started VaynerMedia. Misha was just born. I was trying to do Obsessed TV. I was trying to do the wine
social network, Cork’d. I was trying to do the
social network for developers and designers called Forrst. And I was very stretched thin. I was investing. And so, I learned that I
was trying to definitely put my ass on too many toilets. That’s a Russian translation
for all you Ruskies out there, you know exactly what I’m talking about. And so, I wasn’t able
to balance all of that. And even now, I really, I
feel like I’m starting to take on a lot of stuff. The difference is, I did
a better job up front. There was more selective of the people that I’ve partnered with
on Resy and Faithbox and BRaVe ventures. And this has nothing
to do with the Obsessed or Forrst or Cork’d team. I picked partners that I needed to provide too many things to, besides
capital, and made those promises so, it’s my failure, not theirs. This time around I found
people who had skills that were more similar to mine. I also have dramatically
more infrastructure with VaynerMedia and my team. And so, you know, DRock’s
helped out with Faithbox, you know, and so, you know
Zak has helped out with BRaVe. You know, everybody’s helped
out a little bit here with Resy you know, so there’s,
that’s really it my man. I’ve been very, very, very lucky. I think for the most
part, I think in only, you know, this is the reason
I struggled with yesterday’s question with what I
don’t like about myself. I think there’s something
interesting in the way that I process, that I’m really
getting deeper into myself through this show, through your comments. Just really, really gathering
a lot of pieces right now. And what I’ve realized is wow,
I am really a net net guy. I mean, if you think about all the things that are not working
in my world right now, there’s a ton, there’s a ton
of shit not working out there. Different initiatives,
different departments, a ton. But I can’t help but not
recognize that we’re gonna grow, you know, outrageously this year and be massively successful. And so, there’s probably
tons of flaws with me from yesterday’s question. I’m just not capable of seeing them because in a net net
game, I’m a decent dude. And so, one thing that I
would implore and one thing I would challenge and one thing I would actually want so many of you to shift into is why are you allowing
yourself to look at every small loss along the way? Instead of taking a step back and looking at, minimally, a year. You know, preferably a five year window and say, have you won in that environment? And so, who cares if you, you know how many
investments I’ve lost on? You know, like, in the last two years, you know how many
employees didn’t work out? You know how many flights I took that took up a lot of time
that materialized into nothing? You know how many negative
comments I’ve gotten about this show? You’re allowing yourself, and
this is based on your DNA, so listen, if you need
to go speak to somebody and lay on a couch. If you need to write and express yourself. Find your way to level up your ability to look at things at a net
score versus the minutia from a day to day, week
to week, month to month loss game and I promise you, you will have a happier and more
successful career slash life. – [India] Jay asks, “If you’re
in a wholesale business,