culture and look at zeitgeist. Where is culture
swinging and where do I authentically
intersect with that? For me, I’m great at connection and I love the
technological age. I love how
accessible information is. I love that with
education at our fingertips. I love that it’s
disrupting everything. It have the tremendous ability
to cause a distraction addiction and we need to be careful with
our children and with ourselves of how we consume. Now what does that mean?
It’s a very interesting topic. How do we consume in a way that
doesn’t hurt our mental health? That doesn’t cause
neural pathways of addiction and distraction addiction and that’s actually a
very fascinating topic. – I think the thing that a lot
of people are talking about, Simon Sinek has a video that’s
going viral on this right now. I think the question
becomes that we never do is what was the alternative?
– Mhmmm. – So, it’s one thing to say that
we’re addicted to this and we’re spending our time on this. My question is
that same human being, what would they have been
doing with this time– – Mhmmm.
– in 1989? Would they be
addicted to television? I had plenty of friends who
played 11 1/2 hours of Nintendo. – Yep. – You know we’re deploying our
angst against the medium and we’re not looking at
the human being enough. – Absolutely. – You know there’s a lot of,
there’s a lot of kids sitting in their room on their phone all
day long creating Instagram accounts and doing
stuff that would’ve been on the street doing something bad. Like this thought that it’s all
bad is very fascinating to me. I don’t know. I am unbelievably
pro-human being. – Yeah. – I mean back to just data
and behavior and patterns, like we’re still here.
– Yeah. – Like we’ve
had all the ability, when you think about what we could be doing to
each other negatively. We’ve all, there’s so much
carnage that could happen in one second and we don’t and so we
are scared of what we don’t know and I think that, I think that
I’m surprised by the collective cynicism of the of
the American market, for sure, around these
technologies but it makes a lot of sense to me because
every time there is a massive communication shift we
are very cynical of it. – Yeah. And we’re frightened. – We’re scared.
– But what I love is the Millenials already
have the antidote. So they’re already a
product of the culture of being, having the ability to do this
and look at their screen and what are they telling us? We want experiences,
we don’t want things. – Of course.
– That’s the antidote. We get to get out
and have experiences. – Guys, this is nothing
compared to VR in 20 years. – Mhmmm. – People are
gonna sit in their home. You’re never
gonna see them again. They’re gonna put their contact
lenses on and they’ll be gone. This is, I’m being, this is it. Be happy that they’re
actually out and about looking at the phone ’cause of
the San Diego in a pod and they’re not coming out.
– Right. Yeah. – Andy? Really though
because by the way,– – Yeah? – to your point, and I
see where you’re going. It’s why we’ve
always loved reading books, and watching movies. We need to escape–
– Yeah. – for our mental health.
– Mhmmm. – That’s what this is. It becomes the
alternative universe. The much more extreme version
of that is gonna be the virtual reality world when they
can absolutely in 20 years technology put in
contact lenses and be somewhere. – I always add in caveat–
– Go ahead. – a lot of people talk
to me about mindfulness and, you know, about
being in your head. It’s actually not about,
we do need an escape. – Yes. – Our minds will
run us, they hijack us. – Yeah. Yep. – And so a lot of us use
escape so that we don’t, so that we can escape our minds. I look at our bodies
as an amazing machine. And it’s an amazing machine, our brain is
actually not the driver, it’s the steering wheel. So who’s the driver? I think it’s our observer. When we get so
caught up in our mind we’re desperate for an escape. For me that’s when mindfulness
tools come into play with how we interface
with everything. You have to give yourself a
break from your mind that’s healthy habit and not
just constantly a distraction. – Jewel, just because
you’re so deep in this. This is what I want
to ask you for me. I’m being selfish now. I don’t know the answer. I’m curious for
your perspective. I don’t need an escape.
– Mhmmm. – I don’t want to escape. I’m super duper pumped.
– That’s good. – Like I mean it. Like, I’m even
scared to do meditation, this is real because I’m so
happy with my mental state that I don’t anything that
rejiggers anything ’cause I never need an
escape from anything. I’m super it’s true, And. I deal with plenty of stresses
and things of that nature. I don’t know, I like it. It’s fine, it’s part
of the, I don’t know. What do you think about that? – I don’t know what
to think about that. But I know you
can trust yourself. – Yeah, and?
Have you seen that? How do you think about that? It’s just interesting to me that I don’t gravitate
towards an escape at all. – That’s awesome. – I don’t want to, I want to
stay in my head all the time. – Yeah?
– It’s cozy. – Uh-huh. What’s it like in there?
– Fucking awesome. – Yeah?
(group laughter) That’s good.
– Alright, And. One more time.
One last one?

People, organizations you
won’t work with for whatever reason? – That’s an interesting question. You know and actually, one thing I promised myself
on my comeback trail, here in episode 216 is I’m
gonna answer these questions not just kind of
literally, black and white, but I’m gonna really
challenge myself. I think the golden
eras of the show was when I could
answer the question, but also then know how to bring
value to the whole audience and I, right off the bat,
came in hot, I’m excited. Which is, I don’t and
now let’s talk about it. I truly believe that
anybody who has a shit list has a vulnerability. Because when you’re
using negativity to drive your success,
I think that’s a problem. To me, spending
any energy and time, with a list of people I don’t
wanna do business with or put out of business, or
negative, or like people that got me and
I’m gonna get them back, I think is insane. It’s stunning to me, looking
back at my 20 year career. There was a guy that I went
to a wine tasting of, went to the wine tasting in
New York City at the Hilton. The Wine Spectator
National Wine Tasting, all the best wineries are there. I came in, and I come,
and I go to this winery, and they have this great
Shiraz, Australian wines are getting super hot, and I’m
like selling a lot of them, more than anybody
in the country. And I come and I’d like
to taste your wine, thinking this guy was
going to react really well because we sold a ton of it. He goes into a curse
laden, I’m a piece of crap. And I’ve never lad this
happen to me in life. Like just drilled me. You’re the devil of the
industry, I hate you. Like nasty, nasty, nasty stuff. And it was because
I was selling his wine at the most aggressive
price in the country and he thought
I was killing his brand, meanwhile, there were 30
other stores selling it for that price, but he hadn’t
been on top of technology yet and didn’t know there was
a site called Wine-Searcher that allowed you to see
every price on the internet, and I was just matching the
best price in the country. But because I was
the biggest guy, when I emailed it
and promoted it, all the other stores that
were selling it for more called and complained. He did no homework,
he was immature, he was very hot at the time so
he had the audacity and ego. Needless to say, the
Australian wines got less hot, over the next five years,
and then that coincided with Wine Library TV’s explosion, and then this guy who said I
was the devil of the industry and the worst piece of
crap, and a loser kid and was never going
to amount to anything, emailed me, five years
later, begging for me to be on the show for
exposure for his wine. And with no hesitation
I said yes. I believe being the bigger man. I believe not holding grudges. I believe that one of the
reasons I’m successful in life, let alone business is I don’t
allow poison or negativity to be stored within my confines, and I think it’s a very big thing. I’ve been talking a
lot more about optimism and positivity being
a real factor, I’m starting to get
a little more zen in my older age, and
I believe that if you have a shit list, if you have a list, if you hold a grudge, you’re
coming at your own expense. That you’re not doing
anything, do I forget? No. But it’s just context,
it doesn’t mean I’m going to get you with it, it just
means I have to navigate around it, and that’s
a very big difference. I don’t wanna stick it to you. I just need to navigate
around your truth and there might be
some negativity there, and I wanna get around it. I don’t wanna walk into your
cancer over and over again, punch in the face either. So, I would highly
recommend for all of you, If I can do anything
with this episode, if this becomes the
moment in your life where you stop thinking
having a shit list. By the way, so many people
in my family love that. They love the grudge list,
Eastern European old school, we’re gonna get them,
we’re gonna stick it to them in the end. I think the positivity
and the winning. I think nothing sticks it to
anybody better than results. Instead of tearing them down, just get so God damned big
that that’s the ultimate I got you back. And that comes
through positivity.

“just broke up, and I’m
feeling really depressed. “For the last four years,
I’ve had someone to talk to “about literally everything in
my life, and now that’s gone. “It’s hard to believe that
a four year relationship “ended in 20 minutes. “I was saving and planning
on proposing to her “in the next few months, and
now that’s not gonna happen. “I feel empty, I feel
a void, I feel blank. “Got any advice on how “to pick the pieces of my life back up?” – Jesus. (laughs) You couldn’t have warned
me this was coming? Well, ya know, I mean,
if this was my buddy, the first thing I would
desperately try to do is I always feel like the
quickest cure for heartbreak off a long-term relationship
is a scummy move of hooking up with as
many girls as possible. I think it helps in a weird way. I really do. I think,
I really do think it helps. So I think, there’s only
meaningful relationships and then kind of like the
vanity of relationships when you break this down, and so he’s coming from a meaningful place and I think the vanity of it all, like the one, the one
micropositive that guys cliche will think about in this moment is, “Well, I can hook up with chicks,” and I think you have to go all in on that. That will last for about three
weeks to three months of fun and is a softener. I think you need to recognize
that you got off easy. I don’t know if it’s Bronx Tale or one of those gangster movies where the guy owes the kid, the kid owes the kid 20 bucks, and he goes and chases him,
and then the gangster grabs him and goes, “You got off easy. “You found out he was a
scum bucket for 20 bucks.” You know, brother, I
gotta be honest with you. I think you got off easy. I mean, it’s a hell of a lot
better that you didn’t propose, that she was, I give her credit. She, a lot of people, a lot of people mail it in and get married to
people that they ultimately aren’t fully 100% infatuated,
in love, and for full life, and I think people are mailing in. Now that divorce is so easy, I think that people just kinda do it, and I actually think, in a
weird way, you got lucky, and I actually give her a lot of credit that she, after a four and
a half year relationship, had the backbone and the guts
to go through a tough process I’m sure for her as well. And so I actually think you
look at this as a positive. I’m an optimist. It’s easy for me to say, but I think at some level,
you take a step back and recognize as much as it hurts now, it would have been tougher and hurt more to unwind after marriage or, what’s so difficult for so
many, after having children which creates such a different dynamic and becomes extremely difficult. And so, you know, there’s
not much I can say that’s gonna make it
feel a whole lot better. Maybe just talking it out and getting the question on the show. The e-mail was asking
for it to be on the show? Or are we just taking somebody’s random? Oh it just, it came in, OK. So, that’s it man. I think, go hook up with some chicks to ease the pain for a few minutes, and then take a step back and
recognize it’s a positive, and then try to learn from the experience and find out the qualities
you really loved in her and try to replicate them in
the next relationship you have, and you know, maybe even find the things that you didn’t like as much in her and try to close the gap and find somebody you love even more.

“When looking at potential
investments that you might “be on the fence about, “how do you balance risk versus reward?” – I always, always, always dramatically value reward over risk. Hey, this is such a great
episode to do this in in the context of everything going on. When I invested in Meerkat, it was obvious that
Periscope was gonna launch within the week of my investment, and that it was completely backed on Twitter’s infrastructure, and that Meerkat was gonna get shut down. As a matter of fact, Meerkat got shut down on Twitter before I made the investment, but the upside was so great, if they were able to win that game, in the world of, remember,
Facebook’s attempt to slow down Snapchat, right, with Poke? Like, you know, the leader
doesn’t always win, right. Remember Blockbuster was
gonna go after Netflix? You know, with their service? Remember Walmart’s gonna
crush Amazon six years ago? Happens all the time, and so, the reward was much greater than the risk, even though the risk was very obvious. I’m always, always going for the upside. The other thing is, I
bet on the jockey a lot. You know, I bet on the jockey a lot, and so investing in someone is not necessarily always
just about that startup. You know, if they’re a true entrepreneur, and I feel they’re a true entrepreneur, they’ve got two, three, four, five, six, there’s a female-driven
company right now in New York that I just bet on that
I’m so obsessed with. I think she’s gonna win in this one, but, like, there’s no doubt in my mind she’s gonna multiple times, and I think Travis and Uber
was the final nail in my coffin that it’s always about the jockey. if you can bet on the right
jockey, you’re gonna win, and so, reward over risk every time. I’m on the offense in life, you know, I do not value, and I feel a far majority of people watching this
show are on the defense. I really do. I feel like when I quantify
the world that I know, 70, 80% of the people fall into defense. They’re telling you and themselves why not verus why it’s going to work, and I do believe that
blind optimism and naivety and self confidence are
enormously delicious traits that allow you to win
more often than you lose, because it’s truly a net-net
game you can lose 800 times. There’s four to five substantial bets that I made in driving
VaynerMedia this year. Two of them are really
working, three of them are not. We won big. That’s how I look at it. I’m not gonna cry about the three. There’s no crying in business. Or baseball.

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

“integrity in the
communications industry?” – Dylan I want to too
and I think the answer is there absolutely is but I
think that there’s integrity, there’s very little integrity
in every single market, advertising, politics, sports, music. The reason integrity is so
attractive is it’s so hard. It’s far and few between and
integrity’s defined differently by everybody and I think
it’s interesting to watch. I actually think society
is giving people more room to be flawed, which is intriguing. I think the level of
integrity, the way integrity is viewed upon today I
think is in a much better place than it was by society
let’s say 50 years ago because I think we’re
now factoring in that nobody’s perfect and we’re making mistakes even by standards like
drugs and relationships and cheating, like intense
stuff, I think there’s an interesting evolution and I think that that’s allowed for a
little bit more gray and a little bit more if you’re
really on your high horse creating a scenario where
you judge integrity. But I think in a lot of ways
there’s plenty of integrity. I think there’s a ton of
integrity out there still. I’ve been saying this
a lot lately, I said on another video, are we gonna bang out that video that I did earlier today? – [Voiceover] Which one, we did four. – Yeah I know, the last one we did. – [Voiceover] The Twitter one? – Yeah, Staphon’s working on it? – [Voiceover] Yup. – In there I say, no I think
it was a different one. – [Voiceover] It was the other one. – It was in another one, I screwed up. But, I’m a big fan of this
thing that’s on my mind right now which is you find
what you’re looking for. You know, I see integrity everyday. Everyday and I think it’s
because I look for it and I look half glass full,
like this is Niagra Falls to me. Like this is a very full
glass and I think that plenty of people can see plenty
of what’s missing. I think that’s as much on you my man as it is on what’s actually
happening in the marketplace.

“What do you is a bigger
obstacle to success, “a lack of time or a lack of capital?” – Roberto, this is a tremendous question. I think the biggest obstacle to success is a lack of optimism. That question in itself
is the problem, my friend. Right? You’re looking at two things
that are both negatives, and guess what? Both of ’em are obstacles. When I started winelibrary.com, transformation for my business, I had time, I worked my
face off every minute, but we didn’t have a whole lot
of money in our profit center so it took more time, right? It’s just the way it is. Today, I have more money,
but boy, don’t I have time. But neither, ever, ever, will be an excuse for me. And so, just to drill
this through the throat of the VaynerNation, that’s
right, I went that graphic, don’t smile DRock,
here’s the bottom line: I refuse to allow you to get
an answer to that question because both of them are firmly square in the excuse column, and I
have no patience for that. There will always be problems. Let’s talk about a million other things that are a way to stop success. The health and well-being
of your family members so it takes your mind away from execution. The country you live in’s government and political concepts in these moments, a la, startups in China that I’ve invested in that got traction, but then people that were
wired in to the government decided to not allow it to happen and then the start up disappeared. Not as easy to be an entrepreneur there, it’s still a communist country. Sorry, it just is. And so all these things
can be problems, right? There’s a competitor
with a billion dollars who’s also skilled and
punches you in the mouth and knocks you out in
the first round, right? The world changing. I mean, there’s just a
million obstacles, right? The media, one bad coverage of you. A moment in time. You know what I think about a lot? You know what I think about a lot? Let’s get really real here,
this is why we did this show. I always, I’m a human being, and I always think about a moment in time. What if I just say the wrong
thing at the wrong time? Right? What if I call out China for
being a communist country in an episode while I’m on a rant, and somebody who’s watching
doesn’t like the way that tastes and that takes away a business opportunity for me in China in seven years? Even though I’m not trying to zing, it’s just things that I saw. What if, you know, what if what if I look down on my phone while I’m driving even though
I’ve really not done that, and I hit somebody and I kill them? And that becomes the story, and then like forget about the story, about what you think about me, I will never recover from that because I killed somebody because
I needed to check a Tweet. These are moments in time. So there are so many things that can keep you from
being successful, right? The people that you invested in having something bad happen to them so it slows you down. My friends, there are a
million reasons why not, but there’s one great reason why, which is, you just gotta persevere, no matter what it is. It’s just the way it is. It’s hard being an entrepreneur. It’s hard building a business. Everybody thinks it’s so easy, that there’s an entitlement. There’s a disaster, zinging China? Here comes my U.S. zing right now: there is an insane generation
of 18 to 25 year olds that think they’re entitled
to having a business because they saw the
social networking movie and everybody’s decided
that if you’re a kid and you know what tech is. Because you used Instagram early on, you’re entitled to
actually build a business. Building a business is hard. And you know what makes it really hard? Everything that happens
every day of every moment. So, you can pick time, you can pick money as the one or two things
that you think stop you from winning your game, but the truth is, there’s a million reasons. 99% of businesses go out
of business for a reason. And that reason is, it’s hard. And so, if you’re watching this show, I’ve got a sense of who you are, and you need to start
creating layers and layers and layers of skin to
be able to get through. Because the glamour of
being an entrepreneur, the goodness, you know you get
very confused by my optimism. Because it’s my optimism, I can’t help it, it’s just how I roll. It’s probably one of
the variable 1% reasons why I’m successful. But please, don’t get it twisted. This is hard. Every day is hard. And if you don’t have the
stomach to weather the storm, you will not be successful. And by the way, let me throw you a real weird curveball, and that’s okay. People have to look
themselves in the mirror and understand if they’re
number two, three, four, five, six, seven in an organization, That has differences
of being a number one, but maybe that’s where
your skill set sits. Maybe that’s how you make
your fortunes and happiness and all the things that
you’re looking for, and so. That question got me
goin’ a little bit, Steve. Because it’s under the context of excuses. And I will never make an excuse. Everything that’s a problem with me, everything I don’t achieve, everything that’s a
problem at VaynerMedia, and everything is my fault. And I succumb to that, and I respect that. And I actually think that’s
the way it should be. And so, um, no excuses my friends.