#AskGaryVee Episode 123: How Creatives Can Start Thinking Like an Entrepreneur

“for pickup hoops and social media. “What, if any similarities do you see “in these two passion points?” – All right DRock, DRock
dropped his headphones. That better be gray DRock,
no editing or you’re fired. Pickup hoops and social media. I think, here’s the one
correlation that comes to mind. I think a good one. I think that it’s super
interesting in the fact that when you play pickup
hoops you actually don’t know who’s going to be on your team, right? Usually ten characters get around, ten, 12 characters, you
shoot some free throws, you have five on five. You look at the dynamics and very quickly, within the first five to ten, 15 minutes, or if it lasts that long, definitely at least through the first five or ten possessions you’re trying
to figure out the dynamics of the teamwork on the team on the spot. I find myself very similar going
through that kind of motion when I’m trying to
learn Vine, or Snapchat, or Periscope, or Meerkat, and old school Facebook, Twitter, Tumblr, Pinterest, Instagram. Those first days, like something’s popped. Like everybody’s talking, I remember Meerkat, this
just happened six months ago, all of a sudden on a
weekend everybody’s talking and obviously I’m in a nice brand position where everyone’s like, when’s
Gary Vee gonna be on Meerkat? Beme right now, right? You’re figuring out your way of doing it on that platform. And to me, it really does
remind me of a pickup basketball where you’re tryin’ to figure
out the dynamics of the game similarly to early days
in social media apps. That was really good.

“Louis CK doesn’t take selfies with fans. “Instead he shakes their
hands and talks to them. “Would 2015 Miss Manners approve?” – So first and foremost, it’s not my place to judge anything. Well, stay calm there, India. It’s not my place to judge Louis CK’s execution, how he interacts with his fans. I think there are very
few things that I hold up to a pedestal more than one’s interaction with their fan base
whether that’s eight people or eight drillion people. There’s one thing that’s
interesting to me in this is, my first gut reaction, that’s not true. I’m so damn curious if he desperately like a religion believes that’s the right interaction, or if he’s just schticking a
little bit to make a point. It got asked on this show, is it a thing, is it a fight the system
kind of play from him? I don’t know much about this
so I’m going on question. You see something? What’s going on here? – [India] Louis CK explains–
– Why he doesn’t take photos. So, I need to check that out. I’m sure it’s super interesting. You’re reading it really quick? – [India] Yeah. – What’s the gist idea? – Just says he doesn’t like
taking pictures with people. – Right, so listen,
that’s his prerogative. I do believe that if
you’re lucky enough to make millions of fucking dollars
to be in the limelight, that there’s certain
things that you should, I think if a fan wants the selfie that you should deliver on that. But, that’s just one
humble man’s point of view. I have tons of empathy
if you’re introverted or you don’t like it, but to me, the fan is always right. And a fan wants a signed
book, if they want a picture, if they want a handshake, if
they just want to thank me, if they want to give me their book, I’m just very thankful
they want to do anything. And so for me, I’m most
comfortable in counterpunching, reverse engineering, the finish
line for the other person. But I can’t be mad at
somebody drawing lines because, I mean, he may be a germaphobe. Oh, but he says he shakes hands. Everybody’s got their own thing. I see a lot of people who are
actually very scared of germs that don’t want to shake
fan’s hands and it’s awkward. You know, there’s all
sorts of things out there, so for me I think it’s a misplay, I think more and more people
are going to want to do it. I think it means so much more to them. If you’re a celebrity of his value, I’m sure he has empathy to
recognize that people want to show off that picture
and put it on their social. It’s not the event, it’s
the aftermath of the event. And so I want to provide that
for people that value that, and I’m humbled that anybody
would want to do that with me and I’m sure there’s a lot
of people that weren’t able to take a selfie that are
massively disappointed in that interaction but I respect people creating their own personal boundaries. People are different
than businesses to me. I can get really mad at businesses because there’s people driving that logo but as a human, people have
their lines in the sand.

was one of the winners of
the Crew for a Day challenge. Thank you so much for choosing me. As you can see, I’m
resting up for the big day. But before that, Gary, I have a question. Put yourself in my shoes. You just won a trip to
meet Gary Vaynerchuk. You’re pumped, you’ve been
following this dude for awhile. This is a once in a lifetime
opportunity for you. How would you go about preparing yourself for that type of trip? Would you set expectations and goals or just kind of go with the flow? What would you do if you were meeting you? You keep throwing contests,
I’ll keep winning them. – That’s pretty, listen, I like, by the way, that last part is probably why this question’s on this show. I like the bravado. (breathes deeply) Respectful bravado is very attractive. Bravado insanity is not. That is a little forewarning
to some of the people’s actions in the last couple weeks. I think that what I would
do is I would probably bring him some English peas, because I would know that
Gary loves English peas. And not like the bullshit
kind, like the big ones. You know, like English peas, not like Long Island English peas which are a little smaller. Definitely not snow peas, like sugar peas. Got so many different names. – [India] You walk on
the show with your dad. – Exactly, 118, watch those the big ones so I would bring him that. I’d probably bring him
like a rare Jets jersey of maybe the second or third round pick in the draft this year. What else do I want? I would probably bring some cool Nikes. Something that was like fly like these. I would bribe him to thank him. No. The answer to the question is very simple. I think you’ve already lost. I predict that your Friday
experience is not gonna be as good as you think because you’re already overthinking it. You need to roll in, be you,
the end, the end, the end. It works for me so much. Yesterday Brandon Marshall was here, football player, Jets wide receiver, umps. I don’t even know how to not be myself. First of all, I think I’m
better than everybody, so I don’t get star struck. It’s a flaw and a strength. And I think you roll in with that thing. I think you walk in
and you just need to be basically, it’s so hard, and I get it. Really, around Jets
players is probably where I struggle with it the most
but yesterday I crushed it. Just you have to be yourself,
there’s nothing else. Because then, if it doesn’t, and by the way this is why I fundamentally believe in being yourself. This is the secret
reason to being yourself. If you’re not yourself, and
then it doesn’t go well, you have to think about that
for the rest of your life. You went out of your way to not
let the natural thing happen and it didn’t go well, that sucks. I’d much rather be like, welp? When I get a comment
that like, “you suck.” Right now, the USC video and
the Monday motivation video are both going viral on Facebook, right? A lot of people have never seen me before. When somebody says you
suck, I’m like well, that was me, that’s just
where the chips fell. But if that was my schtick or
that was a fake version of me or that, well then that would hurt. Be like whoa, what if
I just was me, right? And so, that my friends
is why it’s always best, because then you don’t
have to second guess.

“What’s your top tip for a creative mind to start thinking like an entrepreneur?” – Derrick, this is a tough one, right? There’s so many creatives
that just don’t know how to be a salesperson, entrepreneurial. They don’t have that gear. They have incredible, creative chops. First and foremost, I
want to be very careful to try to mold you at tactics that you have no chance of winning at. That’s like me saying, how
do I want to start being a great painter? Well I can go watch YouTube
videos to be better at painting and go buy some good paint,
I can start painting, but I have a funny feeling
if I showed it to India, she’d be polite because she’s a wonderful human being,
but with her artistic eyes, she’d be like, yeah, no, Gary really, I could see some stuff there, yeah. I be like, fuck, she hates it. So to me, I’m very
concerned of forcing people. Just ’cause you may be excited about what I’m putting out there
or what society’s pushing with entrepreneurship, let’s make sure the right
answer to this question isn’t how do I go and find a
partner who is a business mind to team up with me as an artist. I can sell way more paintings
of India’s than India can, ’cause it’s just what I’m great at. That’s without me really knowing, truly, as much as we adore each
other, I don’t fully know your entrepreneurial sales abilities, but I just know mine are better. ‘Cause mine are better than all of yours. Just what I feel. That to me, is the answer
to your question my friend, and obviously I gave that answer
because I want to provide, one of the things I think
I’m hitting a roll on in this golden era, is
I’m starting to understand how to answer the question at hand, instead of picking answering
the question at hand or making it broad, if
you’ve been paying attention, this is my own self-critique which is why I think we have momentum. I’m finding a cadence
right now of how to answer the question and at the same time broaden it to make more sense. And so the real story behind
everything I just said, kids, is hey, don’t force
yourself into things that are not maybe naturally there. It’s okay to have a business partner, a team mate, an employee. You don’t even need a partner. Maybe you hire someone
to be the salesperson. Super important because
just like, how do I become X is a very dangerous game, especially if you just aren’t capable, really truly not capable of ever being X, or just being a two out
of a ten index at X. Were you better off spending four years to become a two instead of a zero, when what you could have
done is gone from an eight to a 12 in the thing that
you’re actually great at? Time is valuable, my
friends, time is valuable. – [India] Awesome. – Thanks India.

Gary, which do you care about more? Interacting with people who
are your fans, who love you, or interacting with
people who don’t like you, who are haters? Where do you spend most of your time?” – Ah, Jay this is such, man, Jay is such a smart guy. Actually, you know what? Jay, you may take this is an insult. Jay’s a nicer guy than he is smart. Just a good dude. Jay, I think that there’s some interesting dynamics to this question. I would tell you, me, 2006 until 2013, I would have answered, the haters. You know me, I love the climb. I love the challenge of converting. I also very much believe I’m a good dude. So many people didn’t think
I was on their first impact because they thought I had too much ego. Or I cursed. Those would be the two things
that most turned people off when they’re first interacting with me. Many of you felt that about me. As matter fact, leave that in the comments if you were one of them. As somebody who, the cursing
really was standoffish or this guy thinks he’s
the greatest of all time. It’s been interesting if you watch people that are commenting over
the last couple of episodes, ‘specially in this golden era,
you’ll see a lot of people talking about how humble you are and I laugh because I know
so many people would see that and be like, pfft what? You start getting to see the
layers as they go over time and that’s why I always say I’m gonna win in the course of a marathon. I really, really was all about the haters. All the negative reviews on this, I went, the first hundred bad and replied to and engaged with. And then something switched. And then I said, you know
what, I’m disproportionately spending my time on the converted, versus all these wonderful people, that are giving me these nice accolades and comments and so many of you know, especially in Facebook because everybody that’s been
sharing these episodes and then commenting, I
been jumping in randomly and saying thank you
because I’m so thankful. Somebody said to share this, by the way that’s a subtle cue
to have every single person who’s watching this right
now, share it on Facebook. Everybody that’s sharing it
and getting their friends to see this and bringing me new audience, that’s incredible, versus somebody saying, you’re a douche bag. I need to reward that
behavior because they get happy with the engagement too, so I think I’m in a much better balance. I would even say that I’m
probably 80% the positive, 20% the negative, but
I’m still very committed. It’s just maybe because,
knock on wood, the new show is a format that is leading
to more people liking me. The keynotes are so brash. The one-off rants are so brash that if that’s the first impact, but the show has a different
tone to it that allows more, I’m far more consumable if the
first thing that you ever saw was this show versus, especially depending
on the first question, I still got that in me. So I would say both. I think both matter tremendously. I’m so disappointed in my
contemporaries and friends who disregard and just label
anybody that just disagrees with them a hater. I actually fully understand
why people disagree with me. I have very narrow views,
as a matter of fact, that are completely predicated on where I think the market’s going which are not very
clear to everybody else. I’ve got nothing but confidence. Confidence for days, with like four Z’s. I’ve got confidence for days. I communicate in a certain style. It’s very East Coast. It’s Jersey in the house. I understand. I hate Patriot fans,
fucking hate you guys. You know, I get that. That’s not feels nice if
you like watching this you’re a Patriot fan, like
oh, wait Gary, hits me weird. I got my dynamics. But what it all really comes
down to is everybody matters, and I have enormous empathy
to why people disagree or might be put off by me
in the beginning and I think that they absolutely deserve
my attention just as much as somebody who says I’m
the greatest of all time. I like all people whether
they agree with me or not. Whether they think I’m a dick or not. It’s just all very understandable for me and I also feel extremely at peace to where this all vets
out in our relationship. That’s it, cool.