“who is your all time favorite Jet “and all- time least favorite Jet “and why?” – My all time favorite Jet and my all time least favorite Jet. My all time least favorite
Jet is probably Kyle Wilson. He just ended being a Jet. Kyle, if you’re watching
this, I apologize, it’s just the truth. He was a first-round pick. He was terrible every second of the way. Just, broke my heart. Just did not like the way he played. Didn’t feel that he had
ball skills for a corner. Even when, like, our starting
corners would get hurt he would have to not
play, he was a terrible, I just really disliked him. My favorite all time Jet is Al Toon. I was a young kid, he
was our best receiver, number 88, I loved him with all my heart, I love you, Al Toon, if you’re watching. And that’s it. Those are the real
answers to that question.

“you were wrong and how did you handle it?” – Kyle this is a great
question damn it Stunwin. I’m wrong a lot. I don’t talk about being wrong a lot because here’s the secret weapon. Guys it’s taken 141 episodes to get to the secret weapon. Stunwin the secret weapon
to why I am the way I am. Staphon I need massive
graphics right now. Give me some like rockets coming up here. Secret weapon (whistles)
(rocket engines roaring) I am wrong so much it’s kind of scary. But for some unknown reason, I haven’t fully quantified
this, I’m not capable of giving it much thought and actually spend zero
time post gaming it. I don’t microanalyze for hours, days, weeks, months, years and this is for some of
you out there, lives. For your whole life, you’re microanalyzing why you made that mistake. You know here’s a good mistake. I passed on Uber’s angel round
and left 200 million dollars cold hard cash out of my pocket in a world where my game is being a business man. I would argue that my biggest mistake is disproportionately bigger
than any of my victories. I just don’t you know, I’m
just not crippled by it. I have friends who passed on things and they just can’t ever
get over it, get over it. So, what was my last mistake? I probably made one in my last meeting. I’m probably making one right now. I make tons of wrong hires,
I say things that don’t sell in a meeting, I make bad investments, I make wrong strategies. I started four massive initiatives for VaynerMedia this year,
two crush, two are failing. Like, I mean, I you know, I make mistakes all day. I just don’t respect my mistakes. – [Voiceover] Best wine club asks,

“When do you know it’s
time to hire an assistant?” – Tim asks, when do you know
it’s time to hire an assistant. – [Steve] Show title, by the way. – What’s that? – [Steve] Show title. – Yeah, this is a great show title. Let’s go with that, DRock. You know, for me, it was Matt Sitomer, who worked in the order
department at Wine Library, who is now a lead account strategist in our LA office, who’s the only employee I took from Wine Library to VaynerMedia when we started it, I’ve
enormous heart for him. He’s also battling
Brandon, my best friend, who runs Wine Library for the championship and our fantasy baseball league this year, so it’s Brandon versus Matt, I’m watching that very carefully
for these next 30 days, enjoying that. So, but, for me, it was that I started to have to be places, and I wasn’t completely in
charge, or had all the leverage. What I mean by that is,
when I ran Wine Library and I was literally in the store 12 hours a day, every day, I didn’t schedule a lot
of things, and if I did, I went off memory, and if they showed up and I screwed up and
made them wait an hour, I was okay with that, even
though that was disrespectful of someone else’s time, I
was the biggest wine buyer that they had, and they
were there to sell me, and I was okay with that. When I started having to
show up to conferences, do interviews, when no longer did I have disproportionate leverage,
that if I was off on time and had to make somebody wait, and this is all predicated
because I’m disorganized and I’m not anal and I’m
not into the details, that’s when I changed, and, so, Matt, I said Matt, you wanna be my assistant, I just need it. I’m starting to travel, I’m
starting to do other things, my world’s evolving, I need
to stop being disrespectful, I need to fix this, I
need to figure it out, and I felt that I was very unschedulable, that I couldn’t follow a schedule, in the same way that I didn’t
think I would ever work out, and I would tell you
that having the assistant and following a schedule and working out have been two of the
biggest confidence builders, to me, to know that I’m
capable of changing, because up until that point,
the first 35 years of my life, I just went with whatever was easy to me, which is why I so mailed in school. Following a schedule and working out make me believe that I
could’ve been an A student, where I used to not believe
that to be the case. So, that’s exciting, that excites me for next
four years of my career, that I’ll be able to
mold and do other things, while still completely
betting on my strengths, but trying to round out, not, round out my weaknesses
in a way that’s scalable, that isn’t, take disproportionate
amount of energy, right, it’s, if you’ve noticed, I’ve hacked it with other human beings. An assistant, a full-time
trainer, so, like, if I can use somebody else’s
skills in my ecosystem, that seems interesting, so, for me, the time to have an
assistant was when I felt that I was disrespecting other people. It’s an interesting answer,
but it’s the true answer. You know, I’m just looking
for, I’m looking for, you know,

“What is your biggest goal heading into “the homestretch of 2015?” – My biggest goal, professionally, is where I’m gonna go with
this, is to set up VaynerMedia for it’s biggest year, get
all my venture capital, and investing world in
order, a lot of transition, a lot of exciting stuff coming
that you’ll be hearing about, wrap up the book, very much focus on Resy and BRaVe and FaithBox, the businesses that I’m, and Grape Story, the businesses that I’m
deeper involved with, get deeper into the HR of 100 employees at VaynerMedia that I
haven’t gone as far with I wanna have that
personal connection with, dismantle the #AskGaryVee
Show through the winter and put out better and
better and better content, work closely with DRock to make a couple of killer, original videos,
work with you, Steve, to make WineDeals really
powerful, and I think we can, so those are some of the
things off the top of my head. Hopefully have my first really
exciting football season in five years, four years, I really am very optimistic, or maybe not, you’ll find out Friday on
my football preview show, and start the process, and most of all, number one, now put a
little personal in there, continue the workout regimen. I don’t know if you
noticed, but I’m starting to go into muscle gaining mode, and start the process of
hacking more time with the kids from a Monday through Friday standpoint than I have, whether
that’s walking to school, whether that’s coming home early. It’s not built into the infastructure this September, the way I wanted it to be, maybe because I got so much time in August that that didn’t populate,
but I’m definitely, in the same way that if
this show was going on the year before I started working out, I know it started right
when I started working out, you would’ve heard me talk a lot about working out, working out, working out. I’m a very smoke then
fire kind of individual, so I’m starting this smoke
on this kids hack thing, because the extremes are working, but I’m trying to find a little more time.

– [Voiceover] Sam asks,
“What is one of your favorite “questions asked by an
interviewee for a position “at VaynerMedia?” – I don’t like when Interviewees talk. What is my favorite question, by the way there’s a little bit of a truth in that statement. It’s something I’ve been
giving a lot of thought to is, I’m live. Oh, you got something? Oh, A.J. – Did you see the
Outside the Lines report? – No. Oh, AJ, bring some news here on the Ask Gary Vee. – I’m breaking a scoop. – I see you’re happy too, so it’s not the Jets are
in big trouble again. – No, it’s about Spygate. – Oh my God, what? – Three aspects that
came out of the report: one, a owner confidentially
told Outside the Lines that he thought deflategate was a make up call for Spygate. – Makes sense. – Owners are probably generally happy with how good Al handled it,
even though he lost. – Yep. – Outside the Lines is reporting can’t be completely based in fact that they think Spygate
was 40 games worth of tape at least. – Wow. – And, there was one other fact. Mike Marts, former coach of the Rams, – Yes. – on the record is saying
that he put out a statement saying he was satisfied
with the investigation, but that Goodell called
him and asked him to do it and Marts is now on the
record with Outside the Lines saying that he believes
Spygate was really bad, and that, – They lost the Superbowl because of it. – He didn’t say that. – I’m saying it. – But he’s saying Goodell asked
him to put out the statement and he didn’t believe it,
saying that he put out. Outside the Lines, huge
story, exploding right now. – I love it. We hate the Patriots around here. And that’s just a bottom line. Wow. – [Steve] That’s good, I got
a question about Deflategate. – You know what, is that right? That being said, I do
wanna say the following. I’m not upset about the Tom Brady ruling, a lot of you asked me, I’m
happy that he’s playing. I’m happy. Alright, I’m serious, by the way. I’d rather him play. We don’t play them in those sport games. – [Steve] Interviewee questions. – Oh, interviewee. Yeah, you know, the truth is, I don’t have a really
great answer for this. I like when interviewees
ask me honest questions. I think a lot of times,
they’re just mailing it in, they went to some website that says, ‘seven best question to
ask during an interview’ or they have an interview coach, or their dad told them to say something. I hate mailed in bullshit,
I like when they ask, or when they pander to me, like, ‘Gary, what’re you gonna
do when you buy the Jets.’ Like, I don’t need that
either, though I like it, I like being coddled, I don’t need it. We’re there to try to help
them help me help us help them as a team, and the truth
is what I’m looking for, so, you know, not that they
have to go the other way and ask a hard-hitting question, either. I don’t care if it’s,
if they truly wanna know what I’m gonna do when I buy the Jets, then I’m happy. If they truly wanna ask me, like, is the vulnerability of
this company your charisma and personal brand of
what happens without you, if they truly mean it and
they’re not just trying to win points on asking
the hard-hitting question, you know, I think that that
has always been my thing. I don’t want anybody going
too far in either direction of bullshit, just keep it in the lane of something that really matters to you, and so, sometimes I like the, you know, now it’s spurring some memories,
sometimes I like when they ask about, like, how much can they contribute to the 401k, or, do
you really, truly allow unlimited vacation time, like, like, I like when it’s just
actually coming from something they wanna know for themselves. I feel like I’m there to
provide value to them. I don’t think an interviewee
is trying to sell me on them to work for me, I think I’m trying to sell
them on working for me. And so, I really flip interviews
on their head that way, and that’s an interesting
thing altogether. Maybe I just love selling so much, maybe I’m trying from the day we meet, create an environment of safety, which I’m very proud of
that I think I create here. That’s the answer.

“is there anything that you
feel you need to start doing?” – I need to start hacking
more day in and day out time with the kids. I’ve been talking about this out loud. Where’s there’s smoke, there’s fire. I wish I did the show one year earlier, because that whole year
I would have talked about health. The show started right as I started taking care of my health, so I was already in it. You guys have been hearing me talking about going home, taking
the bath with them, or dinner with them. This is me selling myself. What I’m really good at is I keep pounding myself into submission when something doesn’t come natural. I need to hack more time with the kids and they get to six and three now. They’re six and three. Now they’re really, really, there’s things, and I’m
going to the recitals and this and that, but I want more day in and day out time. I’ve been winning on extremities. It’s worked, but now I need to figure
out more opportunities to spend that hour minimum a day with them, walking to school, bath, dinner together. It’s gonna be hard, because I’m really a continuous guy like start and then I just
go, breaking up the day where I have to shut off the intensity that I live with. You have to understand the speed at which my brain is activated and the hyper sensitive nature of how I roll when I’m in my game when I’m, that was me putting on a helmet on the field which is where I start my day. I don’t stop it. That’s why I don’t eat lunch. I’m just on, and so to stop that, defrag, really give, you know, so many of
you are spending hours with your kids and loved ones, but you’re not spending real time. Real time is mentally being in it. Checking the box that you took your kid to baseball practice,
but you looked at your phone the whole time was not being in it my friends. I need to be in it, and to shut that down at five PM what’s been going on for eight hours. Give into listening, consuming, engaging, and then restart, because
that’s what’s gonna happen, is gonna be a real challenge for me, and I need to do more of that.

fifty of your clothes will be less or
more successful entertainer media I love this question fifty my clothes now there’s an aspect
to this answer as long as you know I love being in a number 1 I’m so I don’t
think anybody else so if you’re my clone and we can listen each other we may
conflict and we have major problems and so the answer is if it’s a direct loan
we would crash and burn and not be anywhere close to successful as major
media because they’re be fifty people trying to be number one if I could be if
I could have won ABCDEF all the way through Z twice short because the two letters 26 p.m.
but if 50 bucks can go from 1.1 to 1.50 and go through that latter we would
dismantle the earth and dominate and be the greatest 50 forget about 300 those
workers that one BB 50 and we would dominate the universe my intuition is
strickland’s we’d lose clones with eight week just an intimate week that allowed
us to have that 50 person rank and people listening to each other we would
dominate earth birth mother have you got

“How do I succinctly explain
who you are and what you do “to people who don’t know
and aren’t new media savvy?” – How do I do that? – [India] How would you
explain it to someone? – Me? Oh man, I wish this was
the ask Lizzy Vee Show. My life, my wife, she is my life. My wife thinks this is the… it is literally her favorite thing. ‘Cause we know, we go
to a lot of functions and meet a new couple. And they’re like, so what do you do? And she just gets a kick out of it, because I think your dad,
who’s got some context of me at this point, recognizes it’s not that easy. It’s a long-winded answer. At this point I do say
that I’m an entrepreneur. I think it just saves time. But then there’s a part
of me that feels like that’s a fluffy kind of answer. And so, I also lately,
that’s actually not true. I was going entrepreneur for awhile. But right now, lately, I’m very hard core, I’m a CEO of a large
social digital agency. And I’m the lead partner in a $25 million venture fund. And I’m also the host of
the #AskGaryVee Show. I don’t say that yet, but I stuck it in the other day. I love talking about myself,
so I always love that question and I drag it out for as long
as they’ll keep listening. But that’s what I’ve
been doing at this point.

“Which of your views do
you think has changed “the most in the past five years and why?” – Oh, we’re coming out strong. Which of my views has changed the most in the last five years and why? I yell at everybody to
not draw lines in the sand but the four, five things
I actually care about are pretty hardcore lines in the sand. You know, I’ll talk about
some things that have changed. I think that I’m a better communicator as the CEO for VaynerMedia than I was with Wine Library. I think that I hate confrontation
and negativity so much that I lollygagged, and
it wasn’t easy for me to give critical feedback. I mean, even people in this room have gotten critical feedback, and have fundamentally benefitted from it, and it’s not something that I’m sure that I could’ve delivered
as a younger CEO, which is, I didn’t like it. I literally kind of took the role of like, well, if they’re not
winning in this environment, then eventually I’ll
just, they’ll get fired. If they can’t figure it out,
it’s so good, they’ll get fired and I wasn’t providing that value, so I think micromanaging along the way instead of letting complete capitalism and complete openness
kind of rule the day, is something that I’ve changed. You know, I don’t have that many, you know what’s funny about
that question, Brandon, is I’m over-the-top
passionate lines in the sand as equal as I am to being
willing to change them. I always like to say,
I’m a mobile, mobable? No, no, no. What’s that? Moldable, thank you. Modable dictator, movable,
too, and moldable. Make me! Moldable dictator, because I think that the thing the team will about
is, if you can debate it out, and if it makes sense to
me, I’m willing to try, I’m willing to test. So I don’t get too passionate about it. I’m trying to think. Kids, family balance, work life balance, profit topline revenue. I feel myself changing
on YouTube a little bit, in the current moment, like, you know, Jeff Nicholson on the paid team
is really selling me hard on preroll YouTube and it’s value prop and so that’s a rabbit
hole I’m intrigued by. Growth hacking, I think I was cynical to the term, I didn’t love the term, and so I would kind of like zing it, because I thought it was, I thought, like, Ryan
and other people in it, I thought were really great players, but I thought the term
was getting huckstery, but I very much value, kind of, you know, understanding, you know, result driven marketing, so maybe that. – [Steve] Are you any
risk-adverse in your investments? – Risk-adverse in my investments. No, but I definitely think
that I struggled a little bit to calibrate the 25 million
dollars in Vayner/RSE versus Angel 25 and 50 k for
the first three to four months, but I haven’t changed
my point of view there, it’s still jockey and. There is something I’ve
really changed my mind on, and I’ve brought it up recently. Dammit, I’m so pissed, I’m
good at this top of mind stuff. I’ll keep going with the show, and see if I can dig it up, or we’ll come back to
it in another episode. I’m very into changing my mind. I’ll give you a preview
to changing my mind. I will bash Facebook advertising in three to four years. Bash it. We’ll say that it’s overpriced
and doesn’t deliver, because that’s what always happens, the same way I bash banner pre-roll, and the same way I bash SEM to not being as good
as people think it is, those are my calling cards,
along with e-mail marketing. I’m definitely way more
down on Twitter today than I was three years ago, so, I don’t know if it’s like,
you know, it’s not like a religion change, but
the tactics I believe in constantly change, it’s my kind of, write similar books over and over. Sid, you’re smiling. Something happening on Periscope? – [Sid] They’re like,
‘we wanna ask questions.’ – They wanna ask questions. Periscope, why don’t you
calm your goddamn role for a few seconds and let me do the show. And so, my tactics change a lot, but like, you know, the core things, I believe in being good
to people bring value, things like that means you’re
having shifted that’s so much.

“Or do you even have free time?” – Lucky, I have a ton of free time. Well, it’s not free time, I mean I assume you’re asking
when I’m not working, spending it always with my family, and then the only other thing I like to really allocate time to is the New York Jets. Lizzie and I sometimes
watch documentaries, movies, that’s a fun thing for me. I really like docus. I don’t talk about that. There’s that. Let’s keep going. This is fun. Let’s do a rapid, kind of like a