#AskGaryVee Episode 135: When Is It Time To Get A Personal Assistant?

– [Voiceover] Gregory asked,
“If you ever become the CEO “of a local Chamber of
a community of 12,000, “what would be the first
thing you would do?” – If I became the CEO of a
Chamber of Commerce for a small group of 12,000 people, 12,000 members or 12,000 people in a town? – [Steve] Community, yeah. – You know, I’m a very big
fan of scaling the unscalable. Right, I talk a lot about engagement, one on one engagement, Twitter
videos, depth versus width. When you’re talking about
a town of 12,000 people, even if we’re answering this incorrectly and it’s a membership of 12,000, it’s still a very small number
in the scheme of things. So, what I would fundamentally
do is create a infrastructure to allow me to connect one by one with every single member of the Chamber, and even considering if it’s
a 12,000 person community the thousand to 4,000
people that really care about business in town, and
connect with them one by one via coffee, via Skype, via phone call as much face to face as possible, and ask them to reverse
engineer their objectives, meaning what can the Chamber do for you? What do you want out of it? I’d also have a better
understanding of what I was trying to get out of it
if I was the CEO of that. So, I don’t know if that’s fees, I don’t know if it’s something
as simply noble as making business better in town, if
that’s the objective at hand. That’s a little bit of a tongue in cheek for the people that don’t get my humor. I think I get razzed a
little bit too much for this. I was reading plenty of
comments on these three weeks. Basically my job would be to make the business environment in
this community better, and I think the number
one way to do that is to get people aligned. I think leadership comes
from getting entire group of people aligned on a mission. I actually think the most
effective way to do that is to actually understand
each individual person’s goals and objectives and
then come and find that little sweet spot that
is the closest thing to the overall masses that brings value across the board, and then go backwards. What’s the number one thing
that I can do that brings value to all 600 people at Vaynermedia? That brings value to all 12,000 members, and then go down the
list to where the number 10 thing maybe brings value
to half of the people, but it’s still better
than to three people. So, I reverse engineer
by listening upfront, collecting the data, and
then executing against the top 10 things that will
bring value to everybody in the organization.

– [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.

– Hey, Gary Vaynerchuk, on holiday so I’ve got a question for you. What have you learned from WineDeals, you Instagram account, the best place to buy wine in America? Link me up here. What have you learnt from you
WineDeals Instagram account that small wineries can still use to make a buck on Instagram? Cheers. – Good job, Vineyard Paul. – [Paul] Hey, Gary Vaynerchuk, on holiday so I’ve got a question for you. – Oh, that was on loop? – [Steve] Yeah. – That’s cool. Does it loop? Oh, yeah, yeah, on desktop, I, yeah. Vineyard Paul, great question. I’ve learned what I thought
with creating WineDeals, the greatest place on
Instagram to buy wine, which is people are
disproportionately paying attention to Instagram, plus Instagram has built-in word of mouth functionality. People, by habit, when they
see something on Instagram that they think somebody else is going to be interested in, tag their
friends in the comments. They leave a comment with
that person’s user handle, because everybody’s paying
attention to Instagram, they’re seeing that alert, then they are then checking it out. I have not seen anything work like this since early e-mail, and early Twitter. I’m sorry, this is very early
e-mail, very early Twitter, where anybody who’s on the platform is disproportionately paying
attention to the platform, in a way that creates
aggressive word of mouth infrastructure, so we’re
selling a lot of wine, we haven’t even taken it that serious. Steve, you’re about to get
really, really in there, you know, we’re kind of
in the Summer months, which is fun, but now, here we are, as I start seeing, you know, it’s funny, when I start seeing leaves go orange and, you know, all that stuff,
like, that’s when I know it’s time for money, right, because I came from retail,
and the fourth quarter is what, I mean, literally, this day. I’m gonna literally get goosebumps. This exact day for me, the
day I stopped going to school, was the greatest day of my life, because it was the day that shit was about to get serious at Wine Library, because we’re about to do a lot of sales in these next 16 to 20
weeks, and football, and no school. I mean, just like the best. So, as much as I love running VaynerMedia, and as much as this is gonna
be a much bigger company, and as much as this is awesome, I’m still a merchant at heart, and I, as, I’m fired up to,
you know, here, today, and ready to go, but I can’t lie, a little extra kicker,
because I love selling stuff and, even last night,
with Brandon, I’m like, here we go, like, I’m just so pumped for this Saturday. I had an interesting Instagram cutpost a couple days ago about
this upcoming Saturday in the store, I’ve got
surprise gifts for people, they’re going to see
Brandon, I won’t be there, don’t wanna fool anybody, and so, Vineyard Paul, I think
that people’s attention is on this platform and that you need to be storytelling on it, and
I do think it’s a tremendous, direct response, selling
right hook platform, and WineDeals, as many of you guys know, is straight right hooks. It’s three wine offers
are discount prices, and, buy, the end, like, there’s no thrills, you know, clever, Instagram-like pictures, to the best of our ability, and,
but it’s the wine. So the attention graph is real, people’s word of mouth
infrastructure is real, and we’re picking up a lot of
customers, it’s going well.

“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.

“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,