most big successes have a huge turning point where
things really take off. What was that turning
point for Wine Library?” – Sean, great question. I guess there were some turning points when the Wine Spectator ad that we ran, the first New York Times full page ad, the time I reset the score and took 50% of the beer off the floor
and added more wine, when I started WineLibrary.com, the day I started the email service, the day I jumped into Robert
Parker’s forums in ’97 and became part of the
internet community around wine, the 2000 Bordeaux Vintage,
when we bought heavy, when I first started
promoting wines nobody ever heard of on email, Richard
Partridge Cabernet comes to mind, when I hired Brandon. As you can tell, there are
many moments that we made it, but it was just trucking
along, building on top of each other step by step. My friends, if you listen to
two of my answers on this show, you understand one very
interesting thing about me, which is, I may have
the energy of the hare, but I am the tortoise.
(bell ringing) You know what I’m putting up there, right? That beautiful thing you did, Zak. Show Zak. You did a very nice job on that one. For everybody listening,
I’m pointing to the tortoise and hare image I put out on Instagram. Go check me out on Instagram/garyvee. Anyway, when I made it,
the turning point moment, everybody who’s watching
and asking these questions are looking for this
sign, like I saw the sign, It’s not that. It’s head down, you love
and believe in what you do, and you just never think
about those moments, you just keep trucking along. It’s lunch pail mentality, it’s old school Eastern European
put-in-the-work mentality. I don’t think about these things, guys. The Fortune 40 Under
40 that just happened, is that a turning point in my career? Sure, some people now
think of me differently ’cause I’m in the context of
those people, but it’s not. It’s just chug and chug and chug and chug and chug and chug and chug and chug, And so chug. Thanks for watching the show.

– [Voiceover] Michael asks,
“How do you define hustle?” – Michael, this is funny
because show his face. ‘Cause I can see him grinning. This was the first question– What are we 35 in five? This was the first question
of 150 questions that I can see from the corner of
my eye he literally said, “How do you define hustle?” ‘Cause he could see this (laughter) I mean this is a challenging question. So first of all, it’s
different for everybody, right, but I would say hustle is to me, is that when you have
passion around something, that you were squeezing
every last bit of the juice out of the orange, right. To me, hustle is maximizing
the energy you’re putting into somebody. I’m blown away by people
saying that they’re hustling and they wanna achieve these great things, and then their actions don’t match. It’s like saying you
really wanna lose weight, while eating a Big Mac, right? So to me, hustle would be
putting all your effort into achieving the goal at hand, and for me, that means
making every minute count. Hiring a full time assistant who is… Friday night didn’t happen because I was hustling every minute, like if I miss my 15
minutes to tape this show, I’ve missed my 15 minutes
because there’s so much hustle in my day there’s no, you know, there’s no like… There’s no hanging out. There’s no time we’re like,
if I could do like one joke with you guys as I’m
walking in between meetings, we find that to be a rare
acquaintance situation, like occurrence, not acquantance. Hustle is putting it all in a line. Hustle is waking up one
day, the day before you die, and you realizing you gave it your all until the parenting of your children, the building of your businesses, the philanthropy you wanted to do, whatever you define, it’s just, you know, all in, emotionally
and executionally. In theory and strategy, and in execution. – Hey, Bridget Willard here
from you too can be a guru

– [Voiceover] Darren asks, “How much sleep “should you get on average? “Do you work seven days a week? “Do you have set days off
to spend time with family?” – Darren, you know this
is a great question, I get it asked a lot. I talk so much about hustle
and people don’t think I sleep. You know, I try to get six
or seven hours of sleep. I think sleep is massively
important for the body. Right now I’m working out a
lot, as you guys can tell. And that’s affecting my sleeping patterns. Not that I sleep better, by
the way, everybody thought. I was so exhausted before that I was just sleeping like a rock, I’m
lucky with the sleeping, but I sleep quite a bit. Weekends are for the family. No this on the weekend, anymore
for the last couple years. Lot more vacation time. Going from maybe a week or two, even as early as four or
five years ago to now, then three or four, now even like five. So sleep’s important, rest is important, recharging’s important. It’s not about 365 days
of complete insanity. It’s about 265 days of complete insanity, and a hundred days of really resting and giving you the energy
to have that insanity. I think hustle is about when you’re in it, versus every day doing it, right. So for me, it’s this
Tuesday, uh Wednesday, see? This Wednesday is all in, right? Like I’m gonna go all in
the whole way, every minute. A lot of the people that
are around my life now, even you guys probably,
get very caught off guard of how I have zero minutes in
play for 15 hours in a day. Like there is no, Zak needs
like two minutes to like, hey look at this new
design for Wine Library, and DeMayo, my assistant’s
like, yeah next Thursday. And he’s like, two minutes, right? So I go all in on the days I’m in, but boy, do I rest when I rest. And boy, do I check out when I check out. I don’t even like travel. I don’t want the pyramids
of the Eiffel Tower, I don’t care about the coral reefs. When I vacation, I need
to sleep on a beach. And don’t talk to me. That’s how much recharging. When I sleep, if you walked into my home, punched me directly in the face, and stabbed me with a knife in my left arm while I was sleeping, and
robbed everything in my home, I’d still not wake up. That’s how all in I am when I’m resting. So I’m just an all in character, regardless of what I’m doing.

– [Voiceover] Paul asks, “We get like five views on our video, “three of them being from us. “How do very new and small channels “gain a following when
people don’t interact?” – Paul, nice ratio on your viewership because from Wine Library TV I had a similar thing and it was my grandma and mom, so, I know that world. The reason I was able to build up my channel back in the day and now as well, though I have a bigger base now and you can argue with that, is the quality of the output, right? I mean, at the end of the day, how are you gonna find traction? There’s two ways. One, you can put out great content, that’s what I do. Two, and I don’t know
if that’s what you do, maybe you stink, so we need to talk about that. Two, you need to biz dev. Show this man. Right, so, I’ve done all my biz dev my entire career, but, I’m getting stretched so thin. So, Alex DS is gonna come in and start doing biz dev. So, when I see something from a tweet from one of you, and you want to distribute this content on your page, that used to go to my inbox and it would disappear, or the new WineLibrary.com and there’s wine content there, and I want to get that distributed ’cause you have a food blog, and you’d hit me up on Twitter, that would get passed on. But now, he can capture that and biz dev. So, it’s about biz dev. You now, don’t have
anybody talking about you ’cause you have five views, and all those things. But you need to biz dev in reverse. I’ve been lucky enough to have a 20 year well-executed successful career, so it comes to me, I
deserve it. It’s capitalism. You have not done that yet, but you will, hopefully. I want you to. I want to
look back at this video and be excited that you did. When I didn’t have that, I had to biz dev. When Wine Library was
Shopper’s Discount Liquors and nobody gave a crap, I walked around the neighborhood and knocked on restaurant doors and said, “Can you put these flyers on your counter, “for a 20% off coupon
by the case of wine?” I hustled. You, my friend, need to hustle. Number one, the variable
is your creative. No matter how much you hustle and sell and put out flyers, Steve, and put out flyers. Podcast listeners, that was Steve playing something in the background, I apologize, he just
doesn’t have any manners. I was on a big point too, Steve. No matter how hard I hustle, and put out flyers and made it happen. When people came to Wine Library, if we didn’t have a good selection, if we didn’t get good prices, if we didn’t have good
customer service, we lost. So, the two variables are, can you biz dev, can you make it happen or are you willing to hustle? Do you realize that we can’t be romantic, that, we’re just gonna
put out an awesome show and it’s all gonna work out. Bullshit. What needs to happen is you have to put out an awesome show and hustle your face off 15 hours a day to get people to care. That’s very different
than spamming people. That’s very different
than going on Twitter and be like, “Watch our show, “watch our show, watch our show.” Even in a world where you don’t have a huge audience, you have a way to bring value to somebody. If you can figure out how to do that, and then leverage that value for them to give you what you want which is exposure, you will win. It blows my mind how many people email me every single day saying, “Gary, can you tweet about my show?” In a world where I’m such a hustler and such a biz dev guy, and such a wanter to give
to people on the rise, and none of them ask
what they can do for me, or do something for me. Like, where’s that video,
where’s your video show saying “Hey, we want to do like “five custom GaryVee videos.” In our world, we’ll give ’em to you, you can use them as assets and then maybe you can give us some love. No, because people think about themselves and how do I get views. And what the whole world is predicated on when you’re doing biz dev is, can I give that person
51% of the value of the situation. Because if I do, then they’ll say yes and then I can get 49% of the value, and that’s what I do, day in and day out, and day in and day out. And that’s why I continue to win in a world where people
want 100% of the value. You wanted this question answered ’cause you wanted an answer and you were hoping that you could get on this show
and get the exposure, right, for your channel. You know what?
I’m gonna be a good guy, DRock link it up, there it is. Can’t you do stuff
within the YouTube world? There you go, you got some views. Now, bring some value.

“For blogs just starting
out, how do I get people to be interviewed without
being a big name media company?” – Annie your question really means to me, which is how do I go out and get people where I can
take their brand equity as a starting point for mine, right? Like if I could interview Gary Vee and put it out there some
of his fans will come over, listen to that interview and then they’ll become aware of me. So what you’re talking about
is equity leveraging arbitrage. Brilliant, agree with it, for
the people that are listening. If you look at podcast land
that’s how they all do it. I did a bunch of those interviews promoting Jab, Jab, Jab, Right Hook and then they’re leveraging my name over and over and over again
to build auidience. So it is a classic game. There’s a dirty little secret Annie. People that have leverage and have fame even if you call it z-level fame, like me. They like to talk and so I’m going to tell you something that kind of refers to question number one on this episode which is the answer is hustle. I would just keep asking
and asking and asking. I would audit all the
places that look like you or kind of like you and look at the people that have done interviews there and when you start realizing that I and Tim Ferriss and Seth Godin like to give interviews because
we also like the exposure. We also have been successful
and we like to give back. I loved, a couple of
years ago, or last year, my interview 365 day year thing where I just gave people interviews that didn’t even have any audience because I was giving back. Some don’t want to give
interviews unless you’re big. That’s why you get nos others do it because they like to pay
back to the community and they remember grinding and the person that gave them a break. And so very honestly I
would ask and oh by the way, I got a real curveball for you and this is for everybody listening. Sometimes you need to ask
the same person 11 times. And one could say that
you’re being annoying but if you come from a good place and you do it with a prideful tack and you do it in an appropriate way and if you’re actually listening to what’s going on in their world maybe Tim’s got a new book coming out. Maybe he redesigned his website. Maybe he’s got a new podcast. Those are times to strike like a cobra when they want something and you want something,
then interests align. – [Voiceover] NCG asks “What does one do

to hustle the way you do anywhere outside of the United States?” – Alex this is a ludacris question. It is complete- Do we
know where Alex is from? Maybe you can look it up real quick while i’m answering this question. Alex this is a ludacris question. This question pisses me off so much that it’s starting to start to show with it, as Steve is looking. The thought and nature of people saying well America is an
entrepreneurial paradise is the same conversation that’s happening within America of like to
be great in tech you need to be in San Francisco,
like no good businesses are made outside of Silicon Valley. That is just asenine. Let me just remind everybody that Facebook was invented in Boston. Alright, and the home of the Patriots It’s crazy for me when people debate this. Of course you can. Your country is not the variable
of your hustle life, right? Now the environment that
entrepreneurship is glorified in the US. The UK wants
to be more reserved. China got it’s own version
of entrepreneurship. Yes, does the environment
effect it? Of course. My parents growing up in soviet Russia where there was no business, of course they were effected by that. But your hustle, your work ethic, your drive is not
predicated on your zip code. – [Voiceover] Tony asks,
“Gary, what are your thoughts

So I have a job that I absolutely love, I actually work for ReMax of New Jersey. You spoke for us pretty much
right before I got hired so I just missed you. I love my job. I love what I do. I do social media and graphic design. I work with SEO company.
We develop content and of course I want to get
into doing my own thing, doing my own blog, starting my own hustle, and I have this, and I know it
stems from a fear of failure, but I have this really hard time. I get like crippled when
it comes to like executing, and I know you’re probably
just gonna be like just do it, (beep) them,
go for it, do your thing– – You know me so well. – I just need to hear it like, I need you you to look me in my face
and tell me what I should do. – Do you want it? – Yes, I do. – And so literally you’re
just scared to fail? – Er. – I mean, if you want to go
deep with me, I’ll go deep. Who are you scared to fail in front of? Is it your mom? Is it your
best friend? Is it your sister? That’s the only thing
that holds people back. Something happened to me,
like everybody thinks like oh I’m so nice, look at
what I’m doing right now. Truth is, I don’t give a shit
about anybody else’s opinion so rawly that I’m never scared because if I fail and people
are like, “See hahaha.” It doesn’t even register. In the same way, when people are like, “You changed my life, you’re the best,” I’m able to be grounded,
because it also doesn’t. You know, I’m kind of in
that middle zone, right, like not too high, not too
low, which would confuse people based on my energy but I
equally care about every comment in the YouTube section of this
episode, I’m gonna read ’em but if somebody says, “You
blow and this format stinks,” and, “You should let DRock
edit,” that’s gonna be okay. And so, if you wanna get deep with me, I know for a fact, ’cause
you’ve already given it to me that it’s the fear of failure, now the question becomes to whom. And what I would do is, and
you don’t have to share that with the whole world, I’d go
talk to that person up front. The best practical advice I’ve
ever given in this scenario, and it works over and over is you go and you sit down with
dad and say, or Johnny, or your boyfriend, or your
sister, or your girlfriend, I don’t care who it is right. You sit down, you look
’em in the face and say, “I’m about to do this and the only reason “I haven’t done it for the last year “is I don’t want to let you down, “because entrepreneurship is a crapshoot, “and I’m not sure if I’m gonna win, “but long term I’m gonna win, “and I just need to make
sure if I fail on this step, “that your response to me doesn’t crush me “to never let me have a second at bat.” ‘Cause that’s what it is. – Okay.
– Right? – Yes.
– That’s it.

– Alright. – Anyways, so you know,
I wanna piggyback on that because you were capturing a certain demographic and age group
so I wanna represent all those who are a little bit older. So I’m asking it for them, you know. – Okay. – People who already have
kids, financial commitments, homes, mortgages, blah blah blah, so when you keep talking about how do you audit your
time, how do you analyze what character traits, can
you speak to the older folks, between the 30, 50-somethings, how to go out and make it happen or analyze do you really
have what it takes, because at this point,
these folks probably have 10+, 15 years of experience
in their endeavors already. – The one thing I think, thanks Chef. The one thing that I
think is interesting is, let’s break down the question
a little bit differently which is, there’s a
level of never being able to fully make it but
still being in a process where you enjoy the effort to get there. This is not an all sum
game, I’m okay with somebody being a nuanced entrepreneur,
where there’s a full time job and they’re trying to make it happen. Because what happens is,
you’re almost talking about being an entrepreneur as a hobby there. Right, it almost takes
on, this is something, and I just got goosebumps, so I’m starting to get into a new thing that I’m trying to figure out how to
articulate, I’m doing it here out loud for the first time which is, when does entrepreneurship or going for it take on, morph on, whether
it’s very practical, ’cause you’re asking for the
for the 35-55 year old demo, or when it’s, you’re still
under 30, in your 20s, but you’ve confided into
or picked a job route, when is it actually in hobby land? – Exactly. – When is it, you like
having your side hustle and you’re enjoying it,
but it doesn’t need to or have to become your
life and you don’t have to make a billi, for you to be happy. So, what I would say is,
if you’re up at night and you can’t breathe and
you have to do your thing well then, you just
might not be good enough. I mean, think about all
the people we’ve seen on American Idol who are
like, “I grew up my whole life “and I knew I was gonna
be Whitney Houston.” You’re all pumped and you’re
like, back when people watched and you’re like, you can do it! And then she like, “Aaah!”
and you’re like no, and it’s delusional, but we
have that in entrepreneur land. I get emails every day,
I meet people every day who are delusional about their skill set. I desperately, desperately, desperately want to be the small forward
of the New York Knicks. If I truly acted on that,
like if right now at 38, I’m overseas trying to be
the 13th man on the bench of an Italian B-league
team, that’s not gonna work. It’s not gonna happen no matter what I do, and so, I think the answer
to your question for me, to make it as valuable
for them as possible is are you willing to get
comfortable in accepting that you’re in hobby
zone versus transitioning into that zone, and if you
are, well then in a weird way, that’s your question, these tie in. You can have a best of both worlds. – Right. – If you’re asking me
like, how to get somebody to become self-aware
enough and not delusional that they’re hurting
themselves, that’s not something I know how to really fully answer.

This is not the outfit to do it in, so, one second. Okay, whew. – You’re wrong, brother. You had the right outfit on the first time.
– [Man in suit] I have these, occasional rushes of motivation. It’s like, yes. Now I’m gonna do this. But after a few days, that motivation goes away. So how do you get that constant stream of motivation? Thanks a lot. – You know speakin’, you know, this piggybacks well off of the last question. Ya know, my motivation
comes from a couple places. One, I love what I do. You know, you may not love, again, back to what you want. Especially seeing a lot of the youngsters jumping in today’s show, you may think that doing things is the process needed to what you want, which is you wanna be in Las Vegas with 30 beautiful women around you, and like, drinking
champagne and going crazy. Like, I don’t like that stuff. No, I don’t. You know, I don’t like that stuff. I like the process. So, you know, to me there’s
two things that drive me. One, I love what I do,
for the billionth time. My separating aspect from a lot of you, I’m keepin’ it real, is I love working, I
love putting in the work, I love the headaches,
I love HR nightmares, I love it. I like it. I like the grind. I like that I have a 6:30 call today with an upset customer. I like that. And so, that’s number one. Number two is straight up gratitude. You wanna have real fuel? I don’t know what this meant. I’m just trying to become Superman. If you want real fuel, that was injecting gratitude, You want real fuel to win? Be grateful. Now you can’t be grateful. You can’t watch this video and be like, oh great, Gary Vee said I’m not grateful. In me, in my personality is gratitude. The self-awareness that I was born in the, in the Soviet Union, that the
timing of when I was born, was better than when my dad was born, better than when my
grandparents were born there. It created a scenario
where this moment in time, where America and Israel got together, and made a deal with the Soviet Union, and people were able to leave the country, and that’s it. I got really lucky that,
what I’m great at is, is really kind of glamorized here. Entrepreneur businessman,
whereas in Russia, who knows, I’d probably
be dead or a trillionaire. And so, I’m just grateful. I’m grateful for the greatest parents that one could ask for. I’m grateful for, like, amazing wife. A lot of, unfortunately, I
lost a lot of my grandparents before I was even five. So I haven’t had a lot of death. And so, you know, it’s really like, I don’t even have a gear that’s like, woe is me or too bad. First of all, I also
don’t like complaining. I’ve made this bed. Like I feel ill today, I’m
under the weather, right? But I’m not like, oh. We’re always like, watch this. Here, I don’t know if you can get in here. People are gonna like this. Let’s show something of fun to everybody. I don’t know, talk to me. Can people see the schedule? – [DRock] Yep, they can. – Yep, I mean, like, you know. So schedule, right? Like, workout at 6:30, and travel, and meeting, and meeting, and meeting, and speak, and call, and
speak, and tape the show, right, and then call, and then
meeting, and then meeting, and then meeting, and then meeting. And if you’re paying
attention to 10 minutes, 10 minutes,10 minutes,
five minutes, 15 minutes. Planning meeting, call,
call, coffee, meeting, meeting, meeting,
meeting, meeting, meeting, meeting, meeting, meeting,
and today’s a good day, ’cause it’s a Friday. Because I get to be done, you know, by eight o’clock, with
dinner with some friends. But like, when you go back, you know, I mean, the bottom line
is, I’m in meeting, well this is Jet’s game. But, but (phone clanking against table), I’m making my bed. I’m making my bed, I’m going forward. I’m hustling from six to 11 pm everyday, with every second allocated. There is no break. There’s no, there’s no eat a salad, and read Reddit, or watch YouTube. That is not in my game. Yes, Steve, that was for you. You know that is not in my game. And so, because I’ve made my bed, I’m surely not gonna complain and be like, oh, I’m sick today. Like, I just, you know, no. So that’s it. I don’t even remember
what I was answering., but that’s what I think. (laughing)

“Would you ever automate your position, delegate to as many people as it takes, and spend 95% of your time fully engaged in family and life?” – Absolutely not. And as a young entrepreneur, Young Entrepreneur, let
me tell you something from Old Entrepreneur. Which is, I love the process of the work. I love the grind. I love the climb. You know, I love the idea of
getting to buying the Jets, more so than buying the Jets. It’s the process. To delegate out what I love, would defeat the purpose. Of course, I wanna spend as much time with my family, as possible. But that would be lying to my soul if I didn’t do what I wanna do. And what I want to do for a living is build organizations, build companies, create commerce, be a salesman, be a guidance counselor, HR character, social commentate and put out content. I would suffocate if I
couldn’t put out the work that’s needed to accomplish
the things that I want. Psst. The problem Young Entrepreneur, especially when you’re
a young entrepreneur, is people want stuff, right? They want the bling-bling here, right? They want the cool ass kicks. They want the car, they
want the jet, not the Jets. They want stuff. I don’t want stuff. I want the sweat, and the pain, and the gratitude, and the, you know, happiness that comes along with the work. I want the work, I don’t want the stuff. – Hey Gary, I’ve got a very
simple question for you.