Matthew Berry here from
ESPN, and you and I are friends in real life,
so I happen to know, in addition to all the other
things that you’re into, you happen to love fantasy sports, especially your fantasy baseball. And you know that in addition to my duties at ESPN, I happen to
also own two websites, RotoPass.com and RotoPassBaseball.com. Both these sites cater to
fantasy sports enthusiasts, and frankly, I wanna know what I can do to take it to the next level. I’m lucky that I have a
nice platform here at ESPN, and on my Twitter, and Facebook, social media platforms to
be able to promote the site, but ultimately, it’s just me. And I wanna expand the
site beyond just my reach. What can I do to make the site go viral, what can I do to increase sales, to increase visibility of the site? I don’t wanna take on money or try to raise anything like that,
again, it’s just me. So, what can I do to take
those sites to the next level? – Matthew, first of all, big
shout out, love your work, we are friends in real life,
and digital life, two minutes. First of all, I hate fantasy football, and I’ve never played it, and
never will because my love for the Jets is too intense,
and I don’t wanna hear all the explanations from everybody in the comments section,
leave it for yourself, none of ’em are valid. I do love fantasy baseball,
getting ready for our draft, I’m super pumped. Look, I think it’s content,
content, content, my friend. So, first of all, the
first thing you should do is so many, so many people wanna be in the fantasy baseball, fantasy football, fantasy sports industry. So, first thing is the exposure
of this show’s question alone puts you in the game. I bet you that if, Matthew,
you go into my YouTube channel right now, you will see 11
people that will volunteer to be an intern to work on this project because they wanna put
themselves on the map, and you’ve got brand equity. Like, I kinda, you know what was weird, my first inclining to answer this is like, let me write
a guest weekly column about like, my sleeper picks each week because I want exposure in that world, and you’re the platform for it. And I’m busy, and I’m rich,
and I really still would do it because I don’t need to get paid, I want the exposure, right? And by the way, I said I was rich, and I want everybody to understand that because if you’re poor,
or not as many dollars, it should make you wanna do it even more. That’s the brain twist
that everybody doesn’t see. Anyway, you need to put
it out in the world, Matthew, that I need five
to, you need to take a day of your time and vet 50 to 100 people, and see if they can bring you value, create a team that you give exposure to, and then you need to put out content. Basically, you need to reread
Jab, Jab, Jab, Right Hook, and you need to put out
fantasy sports content, native. Look what’s happened to
this world with my content on Medium and LinkedIn, like, I mean, you need to put out,
where’s your weekly video that you put out on Facebook
of your sleeper pick that then gets amplified? You need to put out content. The answer to your question
in content, content, content. Especially in fantasy,
content is a gateway drug to subscription. You need to figure out how to
afford or use your leverage to bring value to youngsters,
youngsters normally, but maybe oldsters. Do you know how many
retired chicks and dudes would do this as well ’cause it’s fun? You need to find the right
person that matches up to this opportunity that
wants your brand equity in exchange for their work
’cause they love doing the work, ’cause they wanna talk
about how much of a sleeper James Paxton is gonna be
this year in baseball. I am preparing for my
fantasy baseball league,

– [Voiceover] Matthew
asks, “Are you worried “you might have created a Steve Jobs-esque “reality distortion
field at VaynerMedia?” – Matthew, first and foremost, I’m massively flattered by this question. I don’t even know how
else to really take it other than, you know, my
ego is very happy with you. I guess not, mainly because, and I didn’t know Steve,
and I knew a lot of people that knew him, but everything’s hearsay. My intuition tells me
that I’m dramatically more a people person and maybe, you know, the answer’s fully no. Do I think that people at VaynerMedia drink the VaynerMedia Kool-Aid and their friends and relatives tell them that they’re drinking the
VaynerMedia Kool-Aid? I do because they tell me
those stories every day. But, you know, look, I mean, is there
times where I realize that if I was a little
more dark and a little bit more of a bad guy that I
could have created a cult and it could have been real negative? I do. But I guess at the end of the day the reason I feel really okay
is I know what my intent is, and I think what matters is if
you know what your intent is, you’re not fearful of that. If I am creating some distortion amongst my employees and my friend base that consumes my content, I think it’s gonna be all for good. I mean, that’s a very, you know. It’s not like, “Ha ha ha,
I’ve got them all tricked “and I’m gonna make 51
cents on every dollar,” it’s, “Holy crap, if I
have them all tricked “I’m gonna make 49 cents on every dollar.” Got it? And that’s a big difference, man. Those two cents? That’s a big difference. That two cents is the whole difference, and so the answer is, I’m flattered, maybe, I don’t think so, and if it’s happening, I
think everybody’s gonna win.

– [Voiceover] Clayton wants
to know, “How do you push “your team beyond their best?” – Clayton, great question. Way to start off 2015, good questions. Oh, actually, I picked this one, right? (people laughing) Hit ’em with some Barry Harowitz’. But that was so subconscious, too. It was a great question.
I thought we should do it. I really, really, really
think that the best way to push somebody above their own means is to guilt them into it. And I know that’s a weird kind of answer. But it is my honest belief
that the thing that drive, first of all, everybody is
driven by different things. So, the real answer to your question is to use your hear, right? DRock, zoom in to my ear. Right, you know, the ear
is the key in this scenario because the truth is,
the way to push somebody above their limit is to
actually have individual conversations with them about what is their Holy Grail. What do they wanna accomplish? Like India and I, I have a
good feel of some of India’s long-term career ambitions. That gives me, first of all, her knowing that we’ve even had that
conversation, in and of itself, gives her a little bit more
confidence to work harder. Because she’s tryin’ to get
what she wants out of it, professionally, and
knowing that I’m the person that can most likely make that happen, at least in the context of this world, that just even having the conversation puts her in better spot. But some people are literally
rawly driven by straight cash. Like, truly, you wanna push somebody? You carrot, like, “Hey,
I know you love cash! “I’ll give you 10,000 more if you, like,” You know, and so, you’ve gotta find out what makes people tick. I’m so not motivated by cash, that so many people try
to get me to do things, JV with me, invest in things, do things, speak at things. And they think cash is the way to do it. And, listen, I love the cash, but it’s not my biggest driver. And I make a lot of
decisions based on legacy, long-term impact, on myself by the way. Not like long-term global impact. You know, that’s not how I think. I mean, I think there’s
a byproduct of that but that’s not the
number one thing for me. But, to answer the
question in a general-form, I truly do believe the best
way to get that is to guilt. And what I mean by guilt,
it’s a variation of listening. Which is not only listening,
but delivering in a world where so few people even begin to listen, let alone delivering on that listening. And once you start doing
that, people start realizing, let me tell you what’s
happening at Vayner; it’s not super confusing. I know exactly what’s
goin’ on in this company. It’s starting to get old enough that there’s enough things
happening for enough people that it’s really easy to
point to Phil Toronto, or to somebody else and
be like, “Wait a minute.” Or Steve Unwin, like, you
can start pointing to, “Oh, crap, that person wanted that, “that person’s getting that, “that person’s happy as crap!” I want that, and so, it’s listening and then delivering, which
then creates a scenario where people want to over-deliver because, the only way somebody
will over-deliver for you, ’cause you asked a very selfish question. “How can I get my team
to over-deliver for me?” “For my thing.” It’s very simple. The best way to get them
to over-deliver, John? – [Trouty] I’m Jack,
if that’s a substitute. – No, Jack is not a substitute. I know what you’re thinking. No, that is not a substitute. – Okay, we’re on the hunt. – The only way to get
somebody to over-deliver is to attack their own
selfishness, their’s. You’re selfish ’cause you want more out of your team to help you. Well, the best way to get that to happen is to over-deliver
against their selfishness. I do believe that guilt is a huge driver because, and there’s something that I, I believe in human beings. I mean, some people don’t
have self-awareness, or empathy, or these emotional feelings. So many people, like, it’s amazing to me now living 20 years professionally, like, how many people are not
confused eventually. They may be emotional at
the time you fire them, or not reward them, but
boy, every time I run into somebody four, seven,
nine years down the line; I’ve had a very good
track-record of them saying, “Yeah, I know why you did that.” I mean, like crazy stuff like, “I had a drug problem!” There was, like, you know, stuff! Life, right? So, I would answer your question like I have before on this show. And you haven’t heard me
say it, I’ll say it again. The single best way to win is to give 51% of the relationship. If there was a jury of 500 people, that they would all
agree that you’ve given 51% to the relationship. And you have to be good enough to know what to do with the other 49. So, I would attack their own selfishness. I would make it so good for them, that you’ve guilted them in delivering. And be very prepared in your stomach by making it awesome. And then them under-delivering, still being entitled to
think they did deliver. And then you being disappointed. “You listened to the Gary Vee Show, “and he told you, and he so great.” Yeah, at least you think
so thank you very much. “And you did it.” And then all four of
these people who you gave $10,000 raises to yesterday, a month later are doing
the same crap they did, and it didn’t motivate them at all. Or you gave them four weeks
off instead of one week off, and they’re still just as crappy. Or you, like, got them a
babysitter, and you pay for it, and they still aren’t. Gratitude and all these
wonderful human characteristics are not guaranteed. But the best way for you to have it happen is to consistently keep trying
to do it for that person. And then, look, I just had a meeting with all these characters, right? But the rest of the team, and I was like, “Look, you may not win on this team.” Like, 2015, I wanna take
it up another notch. And the consolation
prize is you get to work for one of the best
companies in the world. But, like, you just might not
be able to be on this team. You’ve gotta be upfront,
you’ve gotta be fair. You gotta know when you’re
setting up people for victory; and when not, you gotta do that. And then you get to
judge, not before hand. Way too many of you are
making a mistake yourself. You didn’t train, you didn’t
put the person in a position to succeed, you’re not
communicating properly on what you expect. You’re not shooting it straight, you’re scared to hurt feelings. You’re too much of a dick. It could be a million different reasons why it’s not happening, but
it is always going to be the greatest form meritocracy
that you can create. And that starts with your ear and it finishes, in my
opinion, on a second-step move of you actually delivering on that. Call people’s bluffs. I live life on calling people’s bluffs. “Oh, you’ll really crush it
if you have another person?” “Here.” Now, you have to be good enough, back to that 49%, to afford
to give somebody that person. You may not have that situation. But you might have to make a decision. One of the quickest
ways I grew Wine Library was by making 30,000 dollars a
year for five years in a row. Because it took all those monies. And I called people’s bluffs. And when they let me down, do
you think it hurt my feelings that I wasn’t making 45 instead of 30? It sure did, but did I have
my eye on the big prize? Sure did! Now I get paid double that
salary to speak for one hour because I bet long-term,
because I was 23 years old! Right, you gotta know where you’re at. If you’re 83 and you’re watching the show, first of all, big ups, ol’ dog. And second of all, second of all, you know, maybe you don’t
need to play the long-game and invest as much. Maybe it’s time to cash out. I have these weird feelings that in my 80s I’m gonna be rogue as crap, and just take! Because I just gave for so long. I don’t know, you’ve heard
me say that’s my concern. But I can tell you this. (sighing) Most of the reasons, let me phrase. If they work for you, all of the reasons that they’re not over-delivering
against their best, all of those reasons are your fault. – [Voiceover] Harold asks,
“Will you force your children

has India replaced Steve on the show? Where’s he at?” – Ross, this is a
perfectly timed question, because India is right here. – I’m sorry Steve. – And there’s Zak. And Andrew, and then go over here to Staphon and Alex behind him, and DRock get your hand in there somehow. Good. You may notice, no Steve. Steve, this is a message to you. Like I said on email this morning, there is no sickness on our team. When you miss the day,
this is what happens. – Hey Gary.

– [Voiceover] Jarek asks,
“Would you be able to lead any type of company? Do you think that the leaders
can switch industries easily?” – Jarek, this is a great question. You know, I’m speaking for myself that I fundamentally 100,000% believe that I can run any company. I just do. I myself, as you know,
are a reverse engineer. Show the t-shirt. And so what I would be able to do is look, I don’t know, I don’t know dick about
99% of the businesses out there, but it would only
take me about six months with my sponge like skills to figure out whats going on, look at the data, look at the numbers, look at the culture. Reverse engineer,
understand the marketplace and the consumer that’s selling, whether in a B to B or B to C place. There is no business that
me as an operator feel intimidated by. I can’t speak for
everybody, but I do think there’s clearly, I don’t
think I’m that special. I think that there’s other people that also have that
skill set where they can take a look back, really
assess the situation and then operate, and I think that balance comes with sales and HR. For me, I think that’s why I’m able to do so much, for me my strengths are within the HR universe and the sales universe which are really the
two things that you need to know in an organization. You need to be able to sell stuff, and you need to be able to build teams around you. If you’re lucky enough to have that deuce in your life like I
do, then you can do it. – [Voiceover] Ella asks, “What
do you think about Serial?

– Gary, my name is Zac. I’m the CEO and lead designer here at Power Labs, which
is a website design company, and my question for you today is: when you’re faced with two
equally qualified candidates, how do you choose which one to hire, assuming you only need
to hire one employee? I’m asking because I
recently needed to hire on a lot of new employees for 2015, and I appreciate your answer. Thanks, man. – Zac, so many things are
running through my head, all of them are gonna razz
you, which pisses me off, because I really appreciate
you watching the show, and you seem like an awesome dude. A couple things. No such thing as ‘equally qualified’, make a goddamn call, right, just make one. Number two, it seems like
you’re growing pretty well. There’s a weird part of me that’s trying to tell you to hire both of them. The only rationale is
that you can’t justify in any shape or form
within the first six months of 2015, you needing, there’s both so narrow,
back to the last question, great way that worked out, that you could never see you using them, because if you both, if you
love both of them so much, that you should absolutely hire them both. I’m a big fan of hiring
ahead of my growth. A lot of people are always like, how did you grow this so quickly? It’s because I am on the offense and I’m hiring ahead of my growth because I’m not worried about my margin. I’m not hiring enough that
I couldn’t make payroll if something weird happened, you know, and in a week I couldn’t make payroll, I’m leaving a cushion for practicality because I’m an immigrant
and I care about people and I wouldn’t want to have layoffs, but I’m always on the offense. So, the two big things
that pop off for me are, one, you know, are you indecisive or was it, like, the best thing to figure
out how to ask a question for the show, or if you really mean it, as a CEO, and, you know, and this is where, if you’re
CEO and lead designer, you need to put your CEO hat on and make a decision, and then, number two, as a CEO, you’re hiring a lot of people, there’s something weird,
I can’t tell you why, but there’s something weird that tells me you should hire both. – [Voiceover] Courtney asks,

– [Voiceover] Andrew asks, “On
your team, is it better to have employees who’re
specialized in one thing, or people who can wear many hats?” – Andrew, I think the answer is both work. I think you need both in an organization of size, but I, you know, in a world of not trying
to be politically correct on this show, and, like, trying to draw some
real lines in the sand, I’m a huge fan of jack of all trades. Tons of people will tell you
that means you’re not good at any of them. I don’t agree. I think I’m really (beep)
awesome at 19 different things, and I’m watching even
the people in this room and this room get better
at different things. I hate when people use the excuse of I’m great at this,
and I go deep in this to not try to get better at other things. So, to make a 51-49 call,
which is what this is, which is, like, both matter,
both really do matter. DRock’s not good at basketball, but he doesn’t have to do
that for what he’s doing here. This one has a shot at being a meme. Makes Staphon so happy. But I won’t do the DRock, I’m gonna find something on somebody else. I’m gonna go with having multiple skills. I think it speaks to agility, and I love that. – [Voiceover] Anthony asks, “If
given an opportunity to swap

– Hey Gary. Miles Keever with HappyHumanoids.com. In episode 49, you were asked a question about high-end wine
business and was it a hoax. Now, I thought your answer
was brilliant and profound. So profound that I checked
out and I began observing your staff members behind you. Lots of them are standing without chairs, and when you asked Lou to go get DeMayo, somebody snatched his
chair out of the way. Do you have a set up in your community? A way to keep the competitive edge going by not having enough chairs? – First of all, who’s Lou? – [Man] Little Lou! – Oh, Little Lou! You’re right. I literally think of him as Little Lou. This question is so perfect for episode 50 because I’m so devastated that I’m not limiting chairs on purpose to create a competitive culture, so the answer is no. I haven’t created that on purpose, but yes, yes, yes, do I wish I did. I love the thesis behind it. I think it’s a phenomenal observation. I desperately wish it was true. And I will say this, I don’t have any hardcore tactics to create competitiveness. And as a matter of fact, one of the biggest things that I really value is that a lot of the senior people that have been coming into VaynerMedia say this is the first
agency they’d ever worked in that people are competitive
because they wanna do great work but not at the cost of their
other employees around them which means we’re building real culture. It excites me and it’s something that I strive for. But I do think everything
stems from the top, and I don’t know how I do it, but boy, do I know I breed
competitiveness here, because I’m competitive as (bleep). – [Voiceover] Terri says,

– [Voiceover] Sean asks,
“How do you instill “soul and swagger into a
physical product you create?” – Sean, this question is
phenomenal for so many reasons. One: The Wednesday before Thanksgiving I met with a bunch of new
employees at VaynerMedia, and so many of them
talked about this notion of loving it here three months in because that’s usually
when I see somebody, two to three months in. They’re blown away by how
competitive and great everybody is but not at the expense of others. Whereas every other agency they worked, you know, you’re killing each
other politically to move up. You’re like climbing the
dead bodies to the top. And they’re caught off guard by what we have here. My answer to them is,
“Everything stems from the top.” And I really believe that. I’ve said four or five times on this show, “Everything that is wrong at
VaynerMedia is 100% my fault “because I’m the guy.” And I’m empowering Steve
if things are screwed up or anybody else behind me, and so I have a very big belief
in what I’m about to say, which is products take the
byproduct of its leader. So if she has got swag and flavor, then her product is gonna
have swag and flavor. I truly believe that
physical products, right, that physical products
take the personality of the people that are dictating it, that literally, in essence,
the soul, the swag, the vibe, the DNA, is
extracted out of the person and put into the product. And I’ve seen it 100 times because I think when you pay attention, a lot of brands change, and ebb and flow, and a lot of times that
coincides with the CEO, the CMO, the people really dictating the product’s course. You’re making decisions. Humans are the variable. This doesn’t come alive; it’s the people behind
it that instill that. So the answer to your question is the humans behind the
product dictate its outcome, period, end of story. I truly, truly, truly believe in that. Question of the day: I’m gonna ask Steve to ask
the question of the day.

“how did you structure your day?” – Yoli, first of all, I
just wanted to tell you I appreciate all the interaction. Thanks for being a supporter
of The #AskGaryVee Show. By the way, back to the last question. The middle is dangerous. Pre-assistant. I mean, it was a disa– I was such a bad person, you know, I had this power position at Wine Library, where I was one of the biggest
wine buyers in the world, or definitely in the U.S., in the world. And nothing got to my
head, but I was like look, somebody can wait 15 minutes or 20 minutes if I’m like, you know,
finishing up this meeting. They’re here to sell me. So I kind of took the, you
know, the buyer’s approach mentality to that. But what was bad was I
would triple book people, like literally, I used to
be like on floor at 11:30 in the morning helping
somebody with, you know, a big selection for a
party, and I’d see like somebody walk in, and be
like oh yeah, that’s right, I have a meeting with Craig. And I’d be like yeah, you
should try this Pinot Noir, and then I’d be like oh crap,
why did Frank just come in? That’s right, I have a meeting with Frank, and I think it’s at the same time. That’s bad, let me figure
out what I’m gonna do. And by the way, you need a
little cheese for your party. Why did Sally just walk in? Holy crap, I’m triple booked,
and this would happen a lot. And it was complete chaos,
it was disorganized. It wasn’t efficient, and it was piss poor. – [Voiceover] Z asks, “If you were to jump