“Gary, awesome segment with Seth Meyers.” Lisa asks, “With all this
talk about Snapcash, what is the one thing you’ll
teach your kids about money?” – Thanks for the love, Lisa. That’s an interesting question. You know, my parents taught, my mom, actually, really
taught me to respect money. You know, my dad, for an immigrant, was a big thinker with
money in the business. He really let me splurge and take chances. I give him a lot of credit for that. You know, it’s funny. I have a
weird relationship with money. I want it. I’m aware of its benefits. But I’m much more into the PR legacy. You know, where’s my place in history. Much more so about the dollars. I think if you try to
put yourself in history, the money finds you very quickly. You know, I don’t know. My biggest fear is my
kids are going to be rich versus what I grew up with and so I’m trying to figure out some level of creating respect around it. I guess the only thing that’s
defaulting into my mind is I’m going to make those two work. They’re going to work so they earn their own cash and then they can figure out
what their relationship is with their cash. – Hey GV, it’s TF.

– [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

for vetting clients,
specifically at VaynerMedia?” – Dan, answer number one. Do you have enough money? Dan, answer number two. What I’m really looking
for, to not make a joke, and you know, this show’s putting
me in a better mood, guys. I gotta be honest with you. I forgot that that’s what
Wine Library TV did for me on these Mondays where I want
to annihilate people’s souls. Putting on a show with my
community does help my feelings. I need a lot of comments on
this episode, by the way. I need comments in there. I need, I need, comments. Anyway, you know, the things
we’re looking out for is, are they creative? The number one thing I’m scared of is we have a ton of creativity and we can do real work. But if people want to
follow a very strict process of how they’ve always done it versus how we’re supposed to do it. I’m petrified in that. So really there’s no way to do it, because everybody says
they want to be innovative and do the new thing and
invest in the future. And then you get into practicality and the first thing
that’s cut is the future, which is why so many people lose. So everybody’s into defense versus offense when times get tough. For me, when times get
tough, you go harder, not eh. Anyway, so I’m trying to sniff out if people have the
stomach to be innovative and do things differently. To take some risks, but be practical, but have a little more
patience for that practicality and that ROI to present itself. – Gary, I’ve got a very
serious question for you.

So, you know, I just quit my job at radio after being on air since
I was 16 years old. I kinda risked everything
for this new Dash Radio app. I hope you’ve checked it out. You’ve gotta tell me
your favorite station. But what was the riskiest
thing you’ve ever done in your career? Because it was tough for me to leave something I’ve been at for so long, especially an institution
like traditional radio, in order to try something new with zero listeners today to disrupt that industry. What was the toughest choice you ever made in your life or in business
about leaving something that you’ve done to do something new? – You know, again, the enormous excitement I have behind doing this show
and thank you all for allowing me to do this show, is predicated on the fact
that I get to tell you things you’ve never heard before. I’m gonna say something
that I’ve never ever ever ever ever ever have
talked about before. Which is the toughest
professional thing I’ve ever done. My cliche answer historically
has been, you know, leaving the Wine Library
with is my first love, and that’s a very big truth. But as I’ve started becoming a little bit more in
tune with my own feelings and have given this thought, the toughest thing I ever had to do, and Steve, pay attention to me. You’ll like this answer. The toughest thing I ever had to do, believe it or not, was make the decision that I was okay with putting myself out there. You know, a lot of you
probably have at this point forgotten because the Gary Vee persona and narrative has taken over
my career and my Wikipedia and things of that nature. But the first 10 to 15
articles that have ever been written about me in the
AP and the New York Times and the Wall Street Journal was, “Wiz Kid Builds Business.” That the establishment,
the business world, the people that I look up to in ways, maybe not specifically because I don’t really have heroes, but respect their opinions
and their accomplishments. I went from the narrative of being a great business operator that
saw trends and executed it for financial gain,
which is like something everybody deems to be so noble in business to being a self promoter, to being a social media guru. To being an author. Making the decision that I could accept the rolling of the eyes
of the Ivy League grads or the establishment to get bigger reach, to build audience to jam with people, to be human and extroverted and taking that step back or two or three in the minds of the top two or three percent was a pretty interesting,
difficult decision for me. Knowing what the consequences were of putting myself out there
and that I would be respected less for my
business accomplishments because of it wasn’t the easiest thing
that I ever had to deal with and something that’s very honestly I still continue to deal with. I, now, this is where you
start getting into the, I don’t know, DRock, if you
wanna make it dark. But this is where you start
getting into the darkest stuff. In a weird way, I like the underestimation that comes along with it as well. Because the truth is the
reason that entrepreneurship and business speaks to me
especially in an American context is that the truth is undefeated. That ultimately, you
know, if I go and execute multiple hundred million dollar businesses and make smart investments, it’s all net net, right? Like you may not like
the fact that I don’t dress up or that I curse on
stage or that I self promote or whatever you wanna call it. But if I execute, you just have to eat it. And so that was clearly,
DJ, that was clearly the toughest thing for me, which was that I was consciously self aware
that I was entering a realm where I would start
becoming more disrespected even though my accomplishments
were gonna be greater. That mis-positioning was something that, that was tough.