myself, what was the most
important thing you did in your 30s to change your future? – PK why don’t you take that. He’s about to turn 30. – That’s a great question,
and the answer is, I took a deep breath, stepped back,
and I said to myself, where did I kind of want to be in the next 10 to 20 years then. I actually was working at Gillette. I worked there twice and
this was 72-78 and I took a step back and I said you
know, I wanted to be in a position between the ages
of 32 to 35, where I can make a decision to either stay
corporate America on a fast track and doing all those things etc. or shift gears and go into
a small start up, or smaller business environment and write
a couple of my own patents. A bit of an entrepreneurial
spirit, but I wasn’t in a position where I really had those choices. I wasn’t getting
inundated by smaller start ups or new ventures. I so I said you know what,
and I love Gillette they were doing great, and they were
by me and everything that counted, and I said
you know, I gotta get into the New York area, and I
made a decision to move into New York, with a large company
whom I communicated with and said hey for 3 to 5 years,
I’m gonna beat the bushes and see if I want to stay
or go into small business. So that’s kind of when I
stepped back and I said and the rest is history. – That’s cool. So, Peter was there, because
I married Lizzy when I was 28, turned 29 on our wedding night, and so he saw this, which a
lot of you have heard before, which is right at 30 I kind of
freaked out a little bit and started really putting
the pedal to the metal, started Wine Library TV right
after it, and as much as I worked and as intensely
as I worked in my late 20s, 30 started the process of this
insanity that I’m executing against now. So, I just wanna buy the
Jets, but I didn’t think I was going fast enough, and so I
also took a step back and said where am I gonna be in 10 or
20 years, let me make sure my behavior maps it. So, I think if you’re entering
your 30s, I think it’s really smart to think about your 40s and 50s. – So what Gary does on
intuition and gut, and heart, and passion, I kind of did
over my career, maybe in a little more disciplined,
little more balanced, left brain, right brain way,
and it was a driver of why we decided to write the
book, Think to Win, was to try to bring some very
simple concepts and how tos in the world of strategy
and execution to folks who are working in small,
medium, large, companies, public or private, even in
the not for profit sector, where they can take a step
back and say hey look, here are a few principles,
a few how tos, to get folks aligned, fact based– – Yep. – Not myth based, and get
aligned on key issues, key opportunities, and how do we execute. Yogi Berra, who I was a
big fan of, and yes I do have a signed picture from
Don Larson and Yogi Berra. – Cause all of you were curious. – Curious of that, who said,
“A good batter will always be “a good pitcher, and vice versa.” – He is the best. – I’m a believer in good
strategy always drives good execution, and vice
versa, and that’s kind of what this book is about,
a more disciplined way to kind of those how tos to let some power strategic thinking can work. – Tremendous right hook
Peter, let’s go India. – [Voiceover] Ryan asks, “How
do you deal with drama in “the workplace, and how do
you avoid having more drama?”

Has there ever been a point for you where you’ve kind of been
overwhelmed with options for where you wanted to go,
kind of, in your career, and life and what was
the thought process, and the decision making
process you went through when you ultimately made a decision? – I think it’s happened
more, unlike what I think you’re going with your
question as you’re younger, you may be in school,
there’s a lot of options. You know, to me, I was
set at your age, right? I was, I mean, I barely went to college, I was like, I that badly wanted to go into the family business and do my thing. Where I started having
these things happen really is more of like the last
five to seven year phenomenon where I’m crippled by business options. Do I want to be a venture capitalist, do I want to start companies,
do I want to do more econ, do I want to do TV shows? Like, I’ve had a lot
of options in the last five to seven years, and I think for me, you know, what I like to do
is run on two parallel paths. So, here’s my piece of advice. One, I’m constantly debating them, right? I mean, you just have
to, you’re a human being, you’re thinking about your options. But I’m always doing something. I think the thing that bothers me is that people are
crippled by their options, and then actually aren’t
doing anything in parallel, they’re lollygagging while they decide, and to me, whatever you’re deciding, given that these should
all be loaded questions, whatever is in your option
point, you need to be doing. Right, you need to be executing. So, if there’s three
or four tangible things going on in your mind,
you need to make sure your internships, your
free time, you know, whatever you can do to let you taste them and get context around them
is what really matters. – Sweet. – That’s it, good. – Awesome.
– I thought there was gonna be a follow up. – Oh, in terms of that, I mean, that makes a lot of sense, just… – It’s about execution, right? Like, to me, what I was
doing was I showed up on TV a lot, I did angel investing, I ran VaynerMedia, like, I
was doing all these things. I think people are
confused that you could be doing a lot of things
at once if you’re able to stretch that rubber band. – But how much of it
would you say is like, following your passion
versus kind of like, trying new things, and
experimenting, and seeing… – I would never try anything
that I’m not excited about. Like, to me, when I hear you
say following your passion, literally, what I heard is,
how much is it about oxygen? Like, to me, that’s the only thing. Like, everything I just
mentioned are all things that I want to do. Like, do you know how
many people have asked me to go into politics? – I’d vote for you. – So, but I don’t want to do that. And so, I’ve never pondered that. Right? And so, you know, to me, you know, teaching is interesting. I think I’m a modern teacher,
I like it, I love this, but I don’t wanna do
it, I don’t wanna do it in the way that USC actually wants me to teach a course. The guy that I came, and did that course, where he’s like, look,
we’ll set it all up for you, you can be a professor. And there was a part of me
like, my mom would really get a kick out of that,
but other than that, I’m like, I don’t wanna do that. And so, all of it has to do with passion, but you can have passion about a lot of different things. So, to me, if you’re
contemplating anything that’s practical or money
based, get the hell out. Like, oh, I can go into
finance and make more money. That’s, like, I think
that is a terrible idea.

“to have two burning
passions and pursue them “at the same time without half-assing them? “Or is it ideal to pick one at a time?” – That’s a really good question. I, you know I think there’s people that have two burning
passions at the same time. I really do and I wonder
if you can Wuzzle them and make them both work at the same time. That was a 1980’s rare television cartoon Saturday morning reference, Wuzzle. Do you know what Wuzzles are? India search it right now.
– [India] Wuzzles? – Let’s watch India’s face
as, she’s gonna love these watch this, this is India in real time, this is India in real time.
– Wuzzles? – Yeah Wuzzles, W, yep see it?
– [India] Wuzzles? – Uh-huh, go to images
because this is Wikipedia go to images.
– [India] Okay. – I want you to like really
wrap your head around how cool these things are, cool right? They’re two animals in one. So she was like a hippo
– [India] Oh. – and a butterfly, you
see what’s going on here? two animals in one.
– [India] I see it, I see it. Oh I kinda remember this. – Bang that’s what I
was lookin’ for, uh huh. – [India] The two animals in one. – Uh-huh, so maybe you can
Wuzzle them right and find a way to make your two passions… For example, you know
I could’ve very easily made Wine Library TV and the Jets.. What’s goin’ on to you? – [India] (laughing) Wuzzle them. – Well Wuzzle them, like take your two passions
– [India] I know – and smash them into one. – [India] I get it. – Like for example, I could’ve
done all my wine episodes at football games that
would’ve been a further.. You know I have the
Jets bucket but you know there’s ways to uniquely… I think you know I once
said and a lot of you liked this photo on Instagram,
if you order this quote, if you want to be an anomaly
you have to act like one. I wonder based on this question if you could be the first
person that combines two things that nobody’s ever combined
before which are weird and win. For example again, I love wrestling. What if I did Wine Library
TV only at tailgates or football environments
and wrestling matches. Like independent
circuits, like weird stuff where there’s 150 people
in the audience at a gym and the Iron Sheik’s still
there, you know stuff like that. So I’m a big fan of trying
to find a way to Wuzzle them and that’s what I would do. Now obviously a lot of
people are gonna tell you pick one, focus, I may say that at times. Today I felt like Wuzzling
them, tomorrow if I answer this question I might say
pick one, both can work. I think at the end of the
day, and we’ve talked a lot about this, it’s about self-awareness. And it’s funny I’m reading
every goddamn comment in Facebook specifically, right now I’m on a Facebook comment kind
of spree so I apologize to all the YouTubers but
that’s just what’s happening, and it’s interesting I’m
feeling more and more pressure on my shoulders more than ever before because the show is
picking up so much momentum and I’m watching so many people comment about them implementing
and seeing results. And it makes me hungry,
ambitious, greedy to try to impact more people with
what is really working. Which is if you really
know yourself, really India this question comes down
to a very simple place which is it’s one of two choices. It’s truly one of two choices. It’s really just two
levers, it’s happiness and financial and street cred upside. It’s just trying to pull the lever.. and listen I do this, I think
a lot of you may be confused. I leave enormous amounts
of money on the table for happiness. I just do, I do it all the time. The largest speaking gig
of my career, a number that makes me vomit on the
table out of happiness, I passed on ’cause it’s week
four and the Jets are playing in London and I want to go
watch the Jets play the Dolphins in London, and by the way
this is a significant number, this is a hefty six figure deal. This is more money than I
made in a three year period in my mid-twenties to go
and MC and speak at an event for a day and a half. Still could’ve watched the
Jets like I do all the time and I’m choosing happiness
over cash and we all have to do that all the
time and our lives evolve. I’m in a better financial place
than I was seven years ago. Maybe then I would’ve
chose cash, I don’t know, but even in my early days.. For example, when I lost an
eighth of, eight Jesus Christ, a third of my entire wealth in my twenties to have fun in Vegas so I
then lose it all gambling was ’cause I chose
happiness, kinda sadness, over, over, over wealth. And so the answer to this question is predicated very simply. Do I believe there’s, I’m gonna
really, I’m really breakin’ this down India, if you
Wuzzle it you may pop and be an anomaly and have
disproportionate success ’cause you’re the first guy to ever bring spaghetti and music together in this way. Most likely you won’t
and your financial upside is probably predicated on
picking one and going all in. Most likely, however, you
just might have more happiness mixing the two and have the
home run grand slam potential of breaking out which is why
I always do those things. I’m always picking my
happiness versus the straight and obvious course because
I’ve got a little bit of magic and sometimes my weird
stuff actually works as well and the booboo prize is that I’m happier. And boy happiness is addicting. You know what I’m gonna actually – [Voiceover] Vayner Nation
Serious Right Hook war.

– What’s up? (mumbling) 1,700 on Meerkat. Hey, Meerkat. I love it. Cool. Let’s keep it going. Hey. – Chris Green from Massachussets – [Gary] Hey, Chris. Congradulations 100 episodes
of #AskGaryVee. – Thank you, man. Shout out to DRock for that hustle video one of the greatest
videos I have ever seen. – Let’s here it for DRock! (audience cheering) – You can talk about the hustle, you just said two questions ago you can make any company successful, I know you believe that, we all believe it but when you can do so
many different things when your hustle can turn
into so many different things with so many opportunities today 2015 how do you chose what to do and what’s your greatest opportunity ’cause to do what you are doing? – This is the part that I’m not great at. You know, many around me would argue that I’ve done a poor job in selecting opportunity cost because of the earlier question to the gal that pitched
all the stuff of you know, I’m playing such a long, my vulnerability and I think I said it on one
episode, but I am not sure. My vulnerability is that I was too patient and I left the prime years on the table by giving back too much by leveraging too much, by doing non scaleable things too much and so it’s something, you
know, I turn 40 in November and much like when I
turned 30 and freaked out at Wine Library, and
started Wine Library TV I think I’m forcing the narrative ’cause I think it’s convenient. But I’m definitely feeling weird. I’d be lying if I wasn’t. I have been spending a
ton of time on you know, I’m sure I don’t really recall this, but I actually do recall it. I remember thinking
like all right 30 to 40 is going to be the years where I lay down the foundation
to buy the New York Jets. All right, and so, you know, I’ve definitely been
like, you know 40 to 50, like this is it, right? And I’m sure when I get to 50,
I’m like this is really it. You know, but, I’ll be honest with you I’m not sure that I am the
best guy for this answer because the truth is I
like non-scaleable things I love doing stuff like this. Like you understand at some level and I think people will
eventually figure this out about me, and I think a lot of people here probably do recognize it. I disproportionally like
people which will then probably ultimately not allow me to
maybe squeeze out every dollar but I’m still going to
be much happier for it. Like this show, like I’m
going to watch this show. Wait, hold on, let me just talk to myself. You look terrible. (audience laughing) – That was me talking
to my 90-year-old self. Like these things, it’s funny
when I come across somebody tweeting out like an episode of Wine Library TV from like
2006, like I do a ton of stuff that on black and white don’t look like the smart opportunity cost
play, but they are the things that make me happy as a human being and just hustling for the cash so that we’re buying the Jets is only one part
of the equation for me and so I think from a business sense I leave a lot on the table from a life sense, I’m happy
with my allocation of my time. I’m happy that I get together
with former employees that I love so much, even
though everybody around me will say “We need those 15 minutes “for these 700 other things
that need to happen.” I don’t care. And so, I think that you know,
I think the way I judge it is how it feels in my
stomach and my heart. Not my brain. (audience applauding)

when starting up
VaynerMedia from scratch?” – Seth, you know this
is another place for me to give a little bit of insight. Believe it or not, yes, not
doing Wine Library day to day with my dad. Yes, the notion of
taking the risk of being in another family business and
not ruining the relationship with A.J. Confident on both fronts. The hardest thing was actually
being crippled by options. The notion that over
the first nine months, it was very difficult
for me not to think about the fact that me and
A.J had 800 other things we could have done and did
we pick the right thing. I think a lot of people
who are watching this are always crippled. I get this a ton, which is
why I picked this question. Well, I didn’t pick it, you
know, Steve picked or we picked, you know, how did we pick it? – [Steve] This one was collaborative. – This was a little more
collaborative, right? You tried to give me a different question and I said, “No.” No. I like this one, because it
allows me to give an answer to my audience that I see a
lot of you struggling with. It’s been asked of me a
ton on email, twitter, and other places, which is, at some point, you’ve gotta
put your big boy pants on and say, “I’ve made this decision.” And you move on. The buyer’s regret or remorse, or like, did I do the right thing? Or crippled by options is
something so many of you are struggling with. And I struggled with it as well, especially with all the
opportunities that I’ve been able to be given. I’m so fortunate that I’m
struggling with, like, should I do a national TV show? Should I extend the fund by 10 times and do a quarter billion dollar fund? Should I quadruple down on Vayner? You know, I’m crippled. I’m crippled by options, which
is a blessing and a half. And so the hardest thing
was, in 2009, was like, is this the right thing? Don’t forget, Vayner
started in 09, May of 09. Misha was born in May of
09 and Crush It! came out in October of 09. So there was all those
other things going on. The struggle, the hardest thing was not starting the business. It was second guessing, was it the right use of
my time and A.J.’s time and upside and talents at the time. And that’s it.