“When you’re business
is successfully growing, “when do you start another? “And how much time do you devote to it?” – I think it comes down to who you want to be as an operator. Travis Kalanick, CEO of Uber, really taught me a lesson
a couple years ago. When Uber was starting to
take off, he became the CEO. We did angel deals together, and i was pinging him
about this hot angel deal. And he said, “No, I don’t
do angel deals anymore.” And then I pinged him about a talk. And he says, “No, no I’m not gonna talk.” And it was just very focused. And then he’s basically in that Bezos, Steve Jobs, Zucks mold, which is, this is it. This is it. This is the job I’m gonna
do for the rest of my life, and this is my career. I already, clearly, am on my second oofy business. I think I’ve got two
more, three more in me. And so, I’m gonna be an
entrepreneur that has, you know, four or five businesses, is my intuition, India. Clintus. And so, I think it comes
down to who you are, right? And what you want. Like, what’s the size level of a business that gets you to go
into a different place? I mean, VaynerMedia
next year, revenue wise, is going to substantially, probably pass Wine Library’s
biggest year of revenue. So I’ll be going into new territory. Am I an entrepreneur that likes that 50-100 million dollar revenue place, then I go away? Or am gonna see? It really just comes down to a lot of different circumstances. I do think that you need
to question, the question. Which means, if you’re already
asking me this question and thinking about going
on to the next thing, you need to figure out how much you love the
current thing at all. Are you just trying to pass it away? I think there’s a more
interesting insight to that. I think everybody who’s watching the show, needs to think about, are they happy with their business? There’s businesses that you could be making $200,000 a year in, that could be holding you back. ‘Cause it’s a ton of money,
you might just not like it. And so, I think there’s the like factor. For me, I will run this
business, VaynerMedia, as CEO, as long as I love it. That’s really the answer. I mean, I’m glad I got to stick here, because I kind of used a financial proxy as the justification. But to me, as long as I
love it, I mean it could be. But my intuition tells me
I’ve got a couple more. So, I think it comes down to you. And I think it also comes
down to infrastructure. If Brandon Warnke and Justin
Novello and Bobby Shifrin and John Kassimatis and Bryan
Delatorre and Geoff Thurose, if they weren’t in place at Wine Library, along with my dad, I would still be there. VaynerMedia, I mean, some of
you have been here for awhile. VaynerMedia is a helluva
lot better shape today for me not be around, than it was a year ago. I mean, a helluva lot. We’ve gotten dramatically more senior. People have grown. But, I think it’s still
maybe a couple of years away before I feel like it can
sustain and grow without me. And so, the practicality of
this decision matters as well. India, wait a minute, how
did we not talk about this?

“Which of your views do
you think has changed “the most in the past five years and why?” – Oh, we’re coming out strong. Which of my views has changed the most in the last five years and why? I yell at everybody to
not draw lines in the sand but the four, five things
I actually care about are pretty hardcore lines in the sand. You know, I’ll talk about
some things that have changed. I think that I’m a better communicator as the CEO for VaynerMedia than I was with Wine Library. I think that I hate confrontation
and negativity so much that I lollygagged, and
it wasn’t easy for me to give critical feedback. I mean, even people in this room have gotten critical feedback, and have fundamentally benefitted from it, and it’s not something that I’m sure that I could’ve delivered
as a younger CEO, which is, I didn’t like it. I literally kind of took the role of like, well, if they’re not
winning in this environment, then eventually I’ll
just, they’ll get fired. If they can’t figure it out,
it’s so good, they’ll get fired and I wasn’t providing that value, so I think micromanaging along the way instead of letting complete capitalism and complete openness
kind of rule the day, is something that I’ve changed. You know, I don’t have that many, you know what’s funny about
that question, Brandon, is I’m over-the-top
passionate lines in the sand as equal as I am to being
willing to change them. I always like to say,
I’m a mobile, mobable? No, no, no. What’s that? Moldable, thank you. Modable dictator, movable,
too, and moldable. Make me! Moldable dictator, because I think that the thing the team will about
is, if you can debate it out, and if it makes sense to
me, I’m willing to try, I’m willing to test. So I don’t get too passionate about it. I’m trying to think. Kids, family balance, work life balance, profit topline revenue. I feel myself changing
on YouTube a little bit, in the current moment, like, you know, Jeff Nicholson on the paid team
is really selling me hard on preroll YouTube and it’s value prop and so that’s a rabbit
hole I’m intrigued by. Growth hacking, I think I was cynical to the term, I didn’t love the term, and so I would kind of like zing it, because I thought it was, I thought, like, Ryan
and other people in it, I thought were really great players, but I thought the term
was getting huckstery, but I very much value, kind of, you know, understanding, you know, result driven marketing, so maybe that. – [Steve] Are you any
risk-adverse in your investments? – Risk-adverse in my investments. No, but I definitely think
that I struggled a little bit to calibrate the 25 million
dollars in Vayner/RSE versus Angel 25 and 50 k for
the first three to four months, but I haven’t changed
my point of view there, it’s still jockey and. There is something I’ve
really changed my mind on, and I’ve brought it up recently. Dammit, I’m so pissed, I’m
good at this top of mind stuff. I’ll keep going with the show, and see if I can dig it up, or we’ll come back to
it in another episode. I’m very into changing my mind. I’ll give you a preview
to changing my mind. I will bash Facebook advertising in three to four years. Bash it. We’ll say that it’s overpriced
and doesn’t deliver, because that’s what always happens, the same way I bash banner pre-roll, and the same way I bash SEM to not being as good
as people think it is, those are my calling cards,
along with e-mail marketing. I’m definitely way more
down on Twitter today than I was three years ago, so, I don’t know if it’s like,
you know, it’s not like a religion change, but
the tactics I believe in constantly change, it’s my kind of, write similar books over and over. Sid, you’re smiling. Something happening on Periscope? – [Sid] They’re like,
‘we wanna ask questions.’ – They wanna ask questions. Periscope, why don’t you
calm your goddamn role for a few seconds and let me do the show. And so, my tactics change a lot, but like, you know, the core things, I believe in being good
to people bring value, things like that means you’re
having shifted that’s so much.

“you’re the sum of the five people “you spend the most time with. “How do you level up your five?” – This is an interesting question. This is something I’ve spent a lot of time trying to figure out. Do I, am I willing to surround myself with people who are better than me, I know it’s windy, DRock,
relax, we’re outside. I know, a lot of times
I’ve wondered if I’m surrounding myself with
people that are not. You know, I’m very nurturing. I like having a lot of people around me, I like building up people. – True. – Yeah, I like it. – Very true. Listen, not because he’s my son. I don’t want to sit and
brag on in front of him. He’s extremely, extremely special kid. If I knew what I’m going
to get, it’s a true story by the way, his mother
before we got married, said she has this thing,
she wants to have five kids. And of course, being a young
guy I say, hey, no problem. – (laughs) My parents were married at 20. – Right, we were young. And the time went on, I
got scared about education, to be able to pay, the
kids should not have loans, such nonsense, they should all have loans. – I would have paid it off easy. – Right, and so, he’s,
again I’m not going to sit and brag about you– – I think I might have you
on the show more often. This is, I’m feeling nice. – I’m being very honest with you, maybe somebody out there who’s going to stumble
on this video, whatever. His DNA should be bottled. I’m very serious, not
because we had four wines. Well, that helps, but,
I mean, he’s extremely, extremely special in many ways. And Barack Obama doesn’t
invite him to the White House. – Please, this is nice enough,
you don’t have to get crazy. – Just because, as a father I’m very proud. In the business, we had
a lot of disagreements. (laughter) – We could disagree about the
color of the goddamn thing. But end of the day, we
bounce off each other things. And I don’t think Gary
ever mentions that because he’s a very competitive guy. But a lot of good ideas,
and I don’t want to put myself somewhere, but a
lot of them beginning, was Wine Library, it came
driving an hour each way – I wrote a Medium– – I miss it so much. I miss it so much. And I understand, listen,
he’s got things going on, but that part I always miss because it was very special. You know even today when
the family get together, it’s, even my daughter’s
birthday was a couple days ago, you know she turned what, 30? – Six. – Right. – Sorry Liz. – Yeah, no but even her
friends saw the dynamic of our family, and I
have to give it to mom. Mom built a very strong foundation. Who grew up without a mother, you know. She was at age five, she lost her mother, and but she’s very special person who built this family, and you know, I work and she was building the family. It’s a great combination,
and it’s you know I’m very proud what this
family were able to accomplish, and especially what Gary and AJ. I mean you know, special kids definitely. All of them, and I see grandchildren, Oliver and you know. – Alexander. – Alexander. – Alexander is eating a lot of olives, so we decided to name him Olive. – He wants to call himself Olive. And that’s a really real
special, real special. – Thanks dad, I have no idea
Andy what the question was. But, what was it again? – [Voiceover] Sum of the five people you spend the most time with? – Yeah I mean, I think
that, yeah I think I have. I definitely over the
last five to seven years surround myself with
higher caliber characters. I think it’s a commitment, I think, but on the flip-side, I’m
very comfortable in bringing value to the people
that maybe aren’t better than me, I think giving
back is massively important. I think it’s, there’s a level of karma, and I think as long as you’re focused on surrounding yourself with five people that can bring your level up,
I think the real answer is it’s about 10, right, I think it’s about creating a scenario where
you have five people that are leveling you up,
and I think it’s about surrounding yourself with five people that you level up, and I think I think I get tremendous enjoyment on leveling up the five people around me. – [Voiceover] Chris asks,
“I got a question for ya. “How bad do you wish Tom
Brady was your quarterback?”

“and VaynerMedia through
insane growth, what’s your “best advice to those
leading growing teams?” – You know, I think one of
the things that I think about when growing, and you know,
Wine Library probably, from 1998 dad, until
2004 or five, in kind of, that five or six, seven year period, we probably went from what, how many employees do you
think, with Dick and Bob, maybe 10 or twelve to like
eighty or ninety, right? Would you say in that
five or six year period? – Yeah. – So– – But we were overstaffed. – Yes, dad. – No, no, no but we were
overstaffed for a reason. – Yeah, we were growing! – We were growing – And the same thing’s happening now. I’m sure AJ would now
say we’re overstaffed because we’ve gone from
thirty to 525 people in the last three years at VaynerMedia. I think the big thing for
me, and it’s interesting it’s fun to have my dad here. The big thing with me that I think is a little bit different
than my dad and AJ, I’m just, I’m kind of, when you’re going through insane growth, I definitely don’t worry
about the little things. You gotta move fast. There’s going to be a ton of headaches. There’s going to always be issues, but I try to focus on the top line, right. When you’re trying to grow quickly, you’re really growing top line revenue. A lot of times that may be at the mercy of gross profit and net profit. For sure there’s always
issues with personnel, there’s always disagreements
and things of that nature, but for me, it’s not
sweating the small things. To me, I keep my heads
very much in the cloud. I really focus on the agenda at hand, and I think where most people struggle, is they focus on the small things. They get caught up in the things
that may not matter as much in a net net game, and
I think that has been a very major factor in my business success that I’m able to not get caught up in the things that I think
the far majority of people get caught up in. I think people get emotional about things, I think people don’t
project financial outcomes, you know, both when I got
involved in my dad’s business and with VaynerMedia,
the growth of the revenue on the high end, on the top
line, was very extreme and I think that’s something that
people struggle to calibrate. To me it’s not sweating the small things. Dad? – Yeah. – Great, let’s get into the next question. – I think that’s well, well, yeah. – Right? – You know, look, a lot of
people now watch the show. The show’s gotten very big,
I don’t know if you know. – No, I didn’t know. – Ask #GaryVeeShow, it’s very big. – So how come I’m the
first time on the show? – Well, I mean, it’s all
just worked out, timing. You’re very busy, you’re busy. You don’t come to New York
when I’m taping the show. – Right, that’s true. – Tolls, it got too expensive. – You have a very different point of view, you have a very unique point of view on me that the audience does not have. – Listen, no question about
it, not because he’s my son he’s a very, very special kid, no doubt. – I’m almost 40, Dad. – You’re always going to be a kid to me. – I know, I know. – Please. – I get it, I get it. – You’re children will be– – Why don’t you tell the
audience when you first realized how special I was. (laughter) – Oh I knew what– – No, tell them, this will be fun for me. – Shit – I can’t get you to tell me to my face. – No, no! – I always give you the
credit where the credit– – Always. – Okay, what, I’m going
to tell you to your face? No, no, no, you sold drapery right? – Ha, you’re going way back. – Wait a minute. – I was 10. – What year was that? – 1985. – No, before, was (mumbles). – Yeah 1985, I was 10, when
I did the mini flea market. – Mini, Andy, Mini flea market. – ’85. – They had some– – (mumbles) clock. – No, no. – A drapery. A blue drapery. – And my day at that time, I used to take Sunday off once and a while to spend quality time
with my children, right? – Which meant we would sleep. – Listen, I used to work
16 hour days, 14 hour days. – For sure. – That’s not so easy. – Nope. – But, Mom gave you the draperies, right? – Yeah. – And you sold it. – And they were stunned. – Yeah. – And Grandma. – And yeah, listen, I knew it. You’re my son, right? When I lent you, supposedly,
no I did lend you– – You lended me, yep. – Money, a thousand dollars. – You lended me a thousand dollars to start my baseball card
business when I was 14. – I was in the business, right? And a couple people said to
me, you know, you’re an idiot. You’re never going to see this money back. – I paid you back fast. – Fast. – Within the month. – And that was hard, that was like 1989 when I could only go to a
show once every other weekend. – And then you start working in a store. – Kenwood Chardonnay. – No, Sebastiani. – Well, that I asked you to move. – Yeah, well. – Kenwood, I sold. – And that’s uh, yeah. – Alright, let’s go Andy. – Okay, let’s go. – [Voiceover] Buzz.hr asks, I
started a daily vlog series.

for the creative class. I’m a writer and I started
my own marketing consultancy in January and I’m having
an issue getting out and meeting people. You meet a 100 people before breakfast. Some of us don’t have
that kind of personality. So what advice would you
give people like me who have a hard time getting
out, shaking hands, and handing off business cards. What can we do to help
grow our own companies? You have anything? – Jim that’s a great question. Networking doesn’t come natural to– give me my headphones, India. Networking doesn’t come
natural to everybody and the truth is you’ve watched the show probably enough to know I’m a big fan of betting on your strengths versus
working on your weaknesses. I believe people that are
more introverted, reserved, it’s hard for me to ra ra
you into going and like shaking people’s hands
and rolling up on people and being like, “Hey.” Oh no, we’re all great. You know like that’s not going
to be what you do, right? That’s not going to be what you do. That’s what I’d do, but that’s not what
you’re going to be doing. And so, I would say put out great content and play the honey game. Become the honey and
let the bees come to you instead of you becoming
one of the bees, right? And so, I think that’s the game. I think way too many
people are trying to be better at things that seem obviously good. And listen, I spend a disproportionate
amount of time networking. Much of which doesn’t come to fruition. So that could be a waste. Maybe you’re saving a lot
of time being a creative, doing your thing. So, I would say for you and
all the other people out there that don’t want to network,
hand out business cards, shake hands, kiss babies, scare red-headed dudes, I think that you need to go
out and put out great stuff and let people come to you. Let your work speak for itself. I would work in a B2B
Environment and try to get your work seen in other
places except your blog. That can be done behind your keyboard, on email to blogs and
news sites that cover the arena that you play in. That would be my advice to you. Let it come to you. (car engines revving) Cool. Question of the day.

“that is growing fast, is it more important “to perfect the system and process “or focus on adding more
people to the team?” – Jared it’s a good question. I’m a big fan of both. I don’t understand why
not both, I do both. As building VaynerMedia, I
was perfecting the system while hiring people and training them up and building out the team. This is not an either,
or my man and this is where I think people struggle. To really be victorious, I
think you need to be able to do both at the same time. That’s what separates the
women from the girls right? The ability to be able to do
both things at the same time and by the way that’s
where hustle comes in. Because you know what, to
do both you’ve gotta kind of integrate the team nine to five
while kind of spending five ’till like two in the morning
to perfect the system. This is where hustle matters. This is where extra hours
in the day actually matter because you can’t get to both
actually, like physically, you can’t get to both and
so in a nine hour work day. So if you’ve gotta business
that’s growing fast, first question is are you
actually deploying 18 hours a day because remember too
many of you have missed or are gonna miss your moment in time. When it’s happening, when it’s happening if you don’t triple pedal down,
that’s pedal on the metal, like foot on the pedal, if
you don’t go all the hell in, all of it, if you don’t
do that at that moment you will regret. You have missed your moment in time and that is why I’m burning the
candle from both sides right now because everything is
hitting a proper crescendo as I’m going into my 40th
birthday in November. VaynerMedia, Vayner/RSE my fund, cruising, just cruising and the
#AskGaryVee Show cruising you know just, family life and
health, I mean, cruising and so I’ve gotta push harder
because you know what at 42 I mean it might
just be that break and that moment in time where
things aren’t cruising as much and so you’ve gotta extract,
you’ve gotta extract all the value when you’re
hitting that point. You’ve gotta live it,
you just have to live it. As a matter of fact, for all
of you that in your senior year of high school that are watching
your show, squeeze the crap out of that ’cause it’s the best. And college, you’ve gotta
squeeze everything all the time and especially this
question really hits a nerve because I want people to
understand the answer is both.

“Gary Vee, as a successful
solo entrepreneur, “do I have to grow my business bigger “than I can handle alone?” – Q Studios Inc, that’s a great question. I think the answer to that
question is completely predicated on what you want in life. I mean, you’ve set up
the question by saying you’re a successful solo entrepreneur. Are you making the monies
and are you fulfilled enough to keep it at a one woman/one man show? I mean, to me, I can’t
answer that for you. I just had an interesting
conversation with AJ. Our professional ambitions
are in a different place. Everyone’s are. If you wanna build a bigger business, you need to build it
outside of one person. You can only be so big, but maybe what you’re
getting and what you’ve got and how it goes appeals to you. I find a lot of people not
being able to be good managers. They love to micro-manage, they’re romantic and
obsessive about what they do, they don’t allow other people
to come into their ecosystem, and they struggle with the growth curve and they get just as
little exponential growth, they go from making $73,000 a year to 113, but it comes with a lot of pain because they don’t like it, you know? They’re introverted, they’re solo acts, they’re flawed in building
out a big business, but incredibly good and
happy at doing their thing. So it’s not about making more,
there’s really a fine line of making more money
but giving up too much of your happiness for
that bigger money amounts, and then there’s probably
a place where that monies justifies what you want. But to me, doing what you love and doing it the way you love to do it is really, really, really important. I happen to be lucky that that also creates wealth and big dollars, but for the people that it
doesn’t, they need to reconcile. And look, what I don’t get
is a lot of other things, which is kind of the relaxation or the lack of pressure
that comes along with some of the smaller plays, but, I can’t answer this question for you, you need to know yourself. This goes back to all
the self-awareness stuff that I’m trying to put out. This goes back to
yesterday’s video about, or a couple days ago
video of a day in the life where a lot of people
critique my work-life balance, my family time, this, that, and the reason that video
ends with, you know, that’s me, now do you.
That’s a perfect way, actually, DRock, link up there. Give me like a, give me 13 seconds of the day in the life video. – Gary Vanderchuk. – You know I’m a hundred percent right. (laughter) You just do. (laughs) Like, I’m super glad
we’re connected, brother. Alright, now I’m back, and so, you know, I think um, I think it’s on you. – [Voiceover] Adam asks,

– [Jen] Gary, I’m Jen Lebowitz. From New York originally,
but here with my team of community managers from Philly and my brother from New York. – Love it. – Thank you so much for
the show first of all, it’s awesome, we freakin’ love it. – Oh, thank you. – So, I wanted to ask if, well
I know you hate automation. – Yes.
– [Jen] But you get so big to the point where you’re
scaling your community so much that it’s critical to automate.
– What? – How do you decide what and when? – Jen, right, that’s what
you said your name. – [Jen] Yeah. Jen.
– Jen, why is it critical to automate? – Like if you’re getting
thousands of e-mails a day of people registering you can’t manually write back.
– [Gary] Okay. – Okay, okay, got it. You know, there’s some big guys, let me and this is why this show is great. Let me redefine this. There’s a big difference
between automating your human interaction versus
automating a sign up process or something that can and is
acceptable to be automated. Like, for example, I think it was today I just saw it somewhere in my stream. Like did the President of the
United States sign up today? Right like, like I think
you said, the tweet was on twitter I think Barak
Obama finally signed up and the tweet was like, “Now,
I’m finally really here.” There’s a video made six years ago that you can see where
people got mad at me because I said that
wasn’t really Barack Obama tweeting on his behalf
and that was fucked up because everybody was mad at
Britney Spears for like a day for not doing it and having her manager. And like, everybody was all about Obama and down on Britney at the
time, it’s like, fuck this, Britney’s back, baby. So, I wanted to back up
Britney and I jumped in and made a video, and I was like, do you think Barack’s
really doing this? And everybody was mad at me. So, Jen, I think what
you need to recognize is there’s plenty of circumstances where you need to automate, as long as you are not making
like if your automation email when somebody is signing up is like “Hey, Jack, this is Rick.” Really now you’re getting into that level of like trying to fake the funk, but automation is fine in
a lot of places, not just, I don’t want people automating
their human interaction or making pretend it’s them. You know people get pumped when
a celebrity replies to them, that like means something to
them and when they find out that that’s like Ricky
the PM of that person they get disappointed and
that takes equity away. It’s just not authentic. You see what I mean.
– [Jen] Well, thank you so much. Yeah, that’s really helpful.
– Was that it? – Yes, thank you. – Well, no meaning, I don’t
want a second question but like, are we now aligned like, did that clarify that conversation? – That totally clarifies it, thank you. Awesome, well that’s tremendous. All right, let’s clap it up. (audience applauding)

– [Voiceover] Mahdi wants
to know, “What motivated you “to continue any project,
like Wine Library “without seeing any
significant growth prior?” – Mahdi, you know, for me,
that’s a very easy answer, which is, I just believe
in my holistic purpose. I’m blown away by how
many people are crippled by one project or the other,
to me this is a net-net game. I have a very clear vision
professionally where I wanna go but overall, I just want
to be a good human being, do business the right
way, the right process, put in the right hustle
and I control that. If I don’t get results, well
that means I made a wrong strategic decision, but that
doesn’t cripple me either because as a net-net,
I know where I’m going. So for every one or two times I decide to get in the wrong business
or invest in the wrong thing, I’m going to figure out
a win alongside of that and that’s all that really matters to me. – [Voiceover] Michael wants
to know, “As an entrepreneur

Great to see you back. I hope you remember me from Wine Library episode 759 where we drank out of bottles. Enough of that, my question. I run a video blog inmymug.com. Plug, got the plug in.
– Smart plug. – And get about 5,000 views a week but we’ve been kind of there for the last 100 or so episodes. Should I kick on, should
I be bothered about that? We get in sales from it, we
get lots of interaction from it but should I kick on and if I am, should I look at dark posts, should I look at Twitter? What should I kind of do to kind of find that next level? And thank you for the show. – My pleasure, my friend. I definitely, definitely remember you and that was a lot of fun. You know, it’s funny I
was just about to segway in closing off the show about, I also want more viewers and I wanna keep building, like, when you’re in the game,
you’re in the game. You wanna build. And you’ve done the patience thing which is normally my answer. That’s my answer to me. I’m only 18 episodes in and you gotta restart
and rebuild an audience and get people used to behavior and it’s not email or RSS
like I had with Wine Library back in 06, 7, 8 and
so it’s different ways. It’s Twitter but that’s
noisier and different. You know, so, I would say distribution. The reason you’re stuck right now is you need distribution,
distribution, distribution. I highly recommend you say to yourself, what are the 100 websites that are the biggest websites in the world that speak to or are in
the genre of my show? And then literally email them one by one and ask them if they want the rights to distribute your content with maybe you writing on top of it. I’d also reach out to the top 100 podcasts that you can get out there
on and promote the show. Give interviews, you need to hustle. What you just did by
getting on this show worked. You were gonna pick up 39, 42, 73 new listeners for your
show by being on this show. And you need to just scale
the living crap out of that. It’s hustle, hustle, hustle,
hustle, hustle, hustle hustle, hustle, but with
a thread in distribution. You need more awareness. You need to show up on other
YouTube celebrity’s show. You need to get into
the LinkedIn community and start putting out that content. You need to get the hell out there. That is the game, my friend. And that is a nice way to
kind of wrap up the show