“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.

– Good to see you, my man. – Cheers.
– [John] Cheers. – My name is John Henry. I’m a serial entrepreneur now
just coming off of my first exit and now I’m running an accelerator. So, it kind of puts me in an odd position cause my first company,
my success is predicated on how well I executed
– [Gary] Yes. – And now I was predicated on how well my companies get to execute by the way shout out to Shawn I went to Vayner/RSE last week – Awesome
– [John] got to stop by. – Great. – But can you give me some
advice on what to focus on with my companies to make sure that they go out there and kill it. – Yeah, listen, I really
struggled with this transition from being the entreprenaur
at Wine Library to investing after I made the
first three good investments Facebook, Twitter and Tumblr, where I was really just
trying to make money and I was like these
are the best companies. When I then started investing
for real which is interesting

I’m from Warsaw, Poland. – I love it. Julian, are you the one who
I was tweeting with today? – Yes, sir. – And so, you didn’t even
know it was going on today? – No.
– [Gary] And then we tweeted. – Yeah. – And then you showed up. – Yeah. – Big ups to Poland, baby, yeah! (audience cheering) – That’s the ROI of twitter, fuck-faces! (audience laughs)
– [Julian] (mumbling) – All right, sorry, hold
on, I can’t hear shit. Go ahead, start over, brother. – I mean, I was already in New York. – I know you didn’t fly from
Poland 20 minutes ago, dick. (audience laughing) – This guy, this guy. I get it, I get it. – [Julian] (mumbling) – Start over, start over! – I have a health care company that’s focused on limiting
obesity in America and I’m meeting with all
these VC’s and they look at me and I look like I’m 12 years old and they’re like, you know,
“What the fuck do you know?” – [Gary] Yep. – so, I explained the problem they’re like, oh, yeah,
that’s a really good idea like we all really like that,
but leave it to the grown ups and I was going, you know, fuck you and your receding hairline. – [Gary] Dude, I’m losing
hairs watch yourself. Go ahead. – So, how do I get like
some respect from them and actually make and see eye to eye you know, a little kid whose
tackling a big problem. – [Gary] You know look, I think I think the truth is
that’s interesting to me because I would tell you like,
I have no empathy for you because, this is the
greatest era of all time of kids getting disproportional respect because we’ve seen technology grow and you know, I was looking
at the 30 and 40 year olds in this audiance who were like that we wish we had any we wish we were allowed to do anything but, go grab the coffee 20 years ago so, I promise you like, you’re
getting way more respect the fact that a VC is willing to see you is like, way advanced
compared to where it was five or 10 or 15 years ago? I would say this though and look you need to raise money, right? Like you’re not going to see them to go see their receding hairline, you’re going cause you want their money. – [Julian] Yes, exactly. – I wanna align you on
some respect factor you’re going to ask somebody
for their money, right? so, you know, we’re in a place now where money is flowing so freely but, I would also keep
that chip on your shoulder because that’s great. I love that. The best thing to do and I’ve said this before on this show is sell to people that are willing to buy. To me this second I feel any indication that somebody is not interested you look, I’ll give you a good example if I went on a VC pitch and it
was allocated for 45 minutes. And if you sniffed out that just like they’re out, they’re like out. I would cut the meeting short I want that 30 minutes back, right? So, I’ll tell you that sell
to people that are interested versus trying to get
somebody and sell it to them. I’m never selling to anybody but the market that attract,
I’m selling to you guys you’re attracted to this
content. I appreciate that. I’m not trying to convince anybody else. This is right. I’m just
gonna go out and prove it. You know, so I would first
it sounds like you need money I’ve never gone out and raised money I just do shit, make
money, and then go back and tell you I told you
so, right? That you know and so, for me it’s sounds
like you need dollars but, money is easy. Go find the people that wanna find their “Polish Mark Zuckerberg” take their money and go and execute – [Julian] The thing is I’ve
been here for seven days in New York so I’ve of kind
of had an up hill battle but I know what you mean. – [Gary] Yeah, get it, but like I’m not sure what that even meant meaning like
– [Julian] Meaning like – going into a bar where
they only let me in because I am 20.
– [Gary] Right. – I already get like shut down–
– [Gary] Right. – [Julian] where all the
networking events are so, I’ve actually
been standing outside of like Wall Street firms and like hitting up the people. – [Gary] I think your
strategy was fucked up then. – Probably like
– [Julian] Why? Well, I mean, there’s
two ways to look at it. I mean, your strategy is not fucked up if you hustle to get in the
New York, right from Poland to try to raise money then that’s awsome,
but, then I wouldn’t be whoa is me about that like, dude I fucking work 19 hours a day like, I’ve, everybody’s got struggles. – [Julian] I work 20. – What’s that?
– [Julian] I work 20. – [Gary] Cool, I work 21. (audience laughing) So, here’s what I think I think that you clearly
got hustle, right? – [Julian] Right. – And like, I guess, let’s go backwards well let’s make it a
ask the Polish kid show. – [Julian] Okay. Bring it. – What do you need right now? Money?
– [Julian] Yes. – Cool, money is I think
money is shockingly easy. So, what I would tell
you is I would’ve before I came to New
York and knock on doors I would’ve use the
internet, new thing, and I would’ve e-mailed
people, hit them up on Twitter done different things to try to have much warmer meetings in place. How many meetings did you have
in place when you got here? – [Julian] I’ve had about seven. – So that’s good.
So how did those go? – They went well, but looked at me like I was 20 years old and said this is a way
too complex problem to solve for such a young kid we’ll give the money
to someone who’s older who has more experience.
– [Gary] I disagree. I think that’s what you
want to think they thought. – [Julian] Well, I mean
you told me and I said you know, I’m not gonna say it. – [Gary] By the way, I bet
you that they said that you because a lot of people are
bad at giving critical advice they probably just use that as an excuse. Because, I promise you, I know
every fucking VC in the game and they’re pumped to
give a 20 year old money. They just wanna give it to
something that they believe in. – [Julian] Okay, cool. – [Gary] Cool man, good luck. – [Julian] Thanks. (audiance clapping)

“Gary, how can I prevent angel investors “interested in investing in my enterprise “from potentially stealing our IP?” – Christopher, this is
a really interesting Monday morning show. Christopher, this is also a shit question. Ideas are shit, execution’s the game. People walk around going, “Gary, please sign this NDA
before I pitch you my idea as an angel investor.” Let me reenact it. India, I’ll get to that later, let me just catch up on my email. “Hey, Gary, I’m a really big fan and you’re the best guy I’ve ever met. Anyway, listen I’ve
got this big time idea. But before I pitch it to you, please see the following attachment and sign the NDA because I
just can’t let you see it. I don’t want it stolen.” Great, delete. Out of (bleep) business. If you literally think
in 2015 that your idea is so profound that
nobody’s ever thought of it, that when I sit with you and I pitch I go, you’re a dope, but
I’m gonna take this idea and give it to somebody else, you are lost in the
reality of the marketplace. Again, if that is where
your mindset is at, I just don’t see that as a winning mindset for 2015 and beyond. The days of patent or idea IP, every idea has been thought about. There is nobody who has come
up with a big time idea. I’m telling you, every idea
has been thought about. All of them, every one of them. People executing, or having the pieces in
place to be able to execute, or the right time in their career, the right resources financially, energy, skills, opportunities, those are the variables. Not the ideas.

– [Voiceover] Danny asks, “In the past, “what was your equivalent of that “one almond moment from episode 46? “What did you potentially miss out on?” – Danny, I want everybody
in the VaynerNation to go to their copy of
Crush It!, my first book if you’ve got it, and I
want you to go to the first 20 or 30 pages where I do acknowledgments. You will notice that I
acknowledge every one of my family members and then a random name. That random name is Travis Kalanik. Travis is the co-founder and
CEO of a company called Uber that is rumored today to be raising at a $40 billion valuation. When they were raising money
at a $4 million valuation, I passed even though
Travis is one of my boys and I think is one of the best
entrepreneurs in the world. I, at that moment, just
bought a new apartment that liquidated me at
a very aggressive level and I wasn’t so sure
about the idea of Uber that early on, but not that
I didn’t like that idea. I just didn’t think that
Garret, the co-founder of Stumble Upon and then Uber
who came up with the idea, and Travis, I didn’t
think they were actually going to do it. I thought they were going
to hire somebody else and as somebody who went
through, and you’ve heard me talk about in this past
my failures where I put other CEOs in place and I don’t drive it, if it was them driving
it, I would have got in. Hopefully, maybe, maybe
not, but not once but twice because Travis and I are
such boys that I pass on investing in Uber at the angel round. Now, I later invested in
them and I’m going to do quite well, but the valuation
differences are substantial and that $25,000 investment
that I probably would have made, because those were the size
of the checks that I made, right now would be worth
in the ballpark of, if at this $40 billion
valuation, I don’t know what the dilution was or the
prorata, but you can very comfortably say that
you’re looking at somebody who missed an almond by passing in a world where I was
writing $25,000 checks to a lot of dumb crap, let alone the guy, the only guy that I gave
a shout out to in my book in 2009, two years before Uber came out. That $25,000 investment is probably worth in the ballpark between
$75 and $200 million. That’s one big (bleep) almond. Do you know, and I sit
here in front of you with ambitions to buy the New York Jets and no question if I
made that one decision, that one simple decision
that was right there for the taking for me, I would be dramatically further along to my goal right this minute than I actually am. Remember I told you
yesterday that I can take 8,000 punches in the face? That’s 25,000 punches in
the face in one punch. That’s what you have to do
when you’re playing the game. That’s where you have to understand when you’re an entrepreneur. Those misses are going
to come in my career. That’s as big of an almond as I know.

doesn’t invest in rich kids’ businesses. How do you feel about
entrepreneurs from privilege?” – You know, Babs from the Shark Tank is one of my favorite characters,
I like calling Barbara Babs, that’s just something
I’ve been doing for years. Barbara Long, if you’re watching,
that’s where it started. Wine industry chatter. You know, look, I was very much, we all have our prejudices. Since I came from a zero place, I have for a long time talked
about the rich kid syndrome. Right now I talk about
the Ivy League, if I go to an Ivy League school,
I should be a founder because Zucks wears a
hoodie, I’m wearing a hoodie so this is perfect timing. For a long time, I really
pushed against that and said they’re not
hungry enough, they’re not pushed enough. My kids are going to be
rich kids, and I think what I’ve learned as I’ve gotten older, 39 tomorrow, and because of one or two very special friends in my
life right now that grew up very wealthy but are hungry and fiery and making stuff happen,
I think it comes down to anything like a business. I talked about VaynerMedia, I
just had an amazing meeting with somebody and they’re
like, this place is so caring and so good. I thought it was going
to get worse when we got to 400 versus 150, and I said look, it stems from the top. I actually give a crap, and I
think that trickles through. That’s the same thing on this. I, when I meet rich kids,
and see their pitches, spend 45 out of the 50
minutes asking them about how they were raised, how
their parents played the game. The reason I think my rich
kids are going to be OK is because if they act too
rich kiddy, I’m going to punch them directly in their mouth. What I mean by that is, not like literally because I know some of you will freak out. Though I may go there, I’m a little weird and Eastern European. The truth is, I’m going to humble them. I’m going to hurt their feelings, I’m going to make them cry. I’m going to tell them how soft they are. I think that it comes
down to the parenting, just like it comes down
to the CEO in a business. Everything trickles from the top. Just because you grew up
with a hundred million dollar trust, doesn’t mean that
you don’t have the hunger and just because you grew
up with thirty thousand dollars in cash, maybe your
mom did everything for you and took care of everything for you. It’s how you were raised. What’s the foundation? It’s the cement. My dad, Wine Library was built
to be a 16 floor building and everyone made fun of my dad from an engineering standpoint. He’s an old school guy, he
just wants the foundation to be strong and there’s
too much steel and concrete in the basement of Wine Library. That’s how I think about this question. What’s the foundation? I’m not worried about the
optics, the interior decorating. It’s the foundation. – [Voiceover] Zbra Studios
asks, “How long are you going

We do seed-stage investing, and I’ve got a question for Gary. Gary, what’s up with virtual reality? (laughs) – What’s up uh, with virtual reality? First of all, Hunter, great background. As you guys can tell,
Hunter was in the office We’re talkin’ biz. We’ve done some mutual investing together. He’s a great V.C., a great blogger, great Twitter personality,
you should check him out. Link him up during the thing, do something DRock to help the dude. Anyway, Hunter, that’s a great question. I wonder, it’s funny, because I know what you do for a living, I’m like “Hmm, is Hunter looking at this space?” You know, I’ve been talking
and I’ve been doing this move and if you’re listening, I’m
putting my hands on my eyes. Uh, Oculus Rift, it’s coming. You know, I very much think that, look I mean, I hate predictions, but we’re getting close
to the end of the year, where I think we’re gonna force me to do a prediction show,
when I say we, I mean me. Uh, I, uh, 2014, I think by 2024 for sure, that’s 10 years, I think by 2021, V.R.
is gonna really matter. I think video games,
television, and movies, a.k.a. entertainment, and I don’t want to get crass,
but I think porn as well, I think those four categories,
from a business standpoint, will be heavily affected
by virtual reality. And then by virtue, I see advertising going there. Because all of the
sudden, you can imagine, if I’m playing, you know, Madden and I feel like I’m the quarterback, and all the signage
around the stadium is now Lionel Richie, root beer,
wine, things of that nature, you can see how advertising
gets filled into it. I, look, I’m in the
eyes and ears business. If you want to know what business I’m in, and if you want to get a
cut, DRock, of a video clip for a 50-second video for my
YouTube channel, take this one. Because, once and for
all, stake in the ground, I’m in the eyes and ears business. Where ever the eyes and ears go, I go. Right? If I think the ears are
moving quicker and quicker to podcasting because
connected cars are here and mobile devices are here, I start podcasting, get it? It’s how I move. And so, V.R. is coming. As an investor, under the
context of you, Hunter, and asking that question,
I am looking at it. I’m looking at the production companies, the people with the kind of 360 cameras that are gonna be in it. Video game producers that
are gonna play in it. I’m a big believer. I think it’s a little early, and it’s definitely early for mass. But I think over the next three years, you’ll start seeing sprinkles to it, and I think five to seven years from now, virtual reality will have a real place in our society, bigger than
people think right now. In the way that you
didn’t think older people would take selfies three years ago, that’s what I think about V.R. Meaning, a lot of you don’t
think it’s gonna happen. I just do.

– Charlie. – Nice to meet you.
What’s up, guys? – Pretty quick question, what’s your stance on investing
in competitive companies? – Meaning? Like for me as a fund. – You as a fund, you individually – Don’t, guys. – [Steve] It’s gonna
be useless audio though. – It’s not useless
audio, it’s just a horn. Nobody in the VaynerNation
is concerned about a horn. – [Steve] They won’t
be able to hear the words. – They’ll be able to hear the words. Do you think they’ll be
able to hear the words? – Yeah. – Can we hear the words. I get it and I love you
supporting your teammate DRock. I see what you’re doing.
I love the support. But that horn, this fire truck, is adding to the ambiance of the fact that we’re sitting in New York City. Like we’re not sitting in our normal room. They’ll deal with it. Right DRock? Alright, thank you. It pains you right? It’s like the editor in you just like can’t deal with, now the horns are coming. This is just pouring it on you. We’re sticking with it. So, if I’m a fund, for example, when I was an investor in Gowalla and there was a chance
to invest in Foursquare. I didn’t, but I know
people that have invested in similar companies. Are you asking me like
to put my VC hat on? – Yeah.
– And angel hat. You know, look I think,
there’s two answers. One I think, if you’re
investing in a company and then there’s a chance
to invest in somebody who’s a direct competitor and that company wants you to do that. That seems to me like … (sirens blaring) (laughing) That seems to me like a
little bit of a dick move. What I’m more worried about
is the problem I’m facing now. (sirens blaring) I’ll be quiet for you. This is me doing a nice thing for you. But the tape is running,
the tape is running. – It better be. – To me the bigger problem is the pivot. Right now my biggest problem is I’m investing in companies that
are a little bit different. But I can see an entrepreneur how one move by each product gets them in to a competitive space. My answer is, you go in with the open eyes and honesty that you can. But you can’t fight against
the fact that people are competing with each other. As we now live in a world
where the cost of entry to compete with each
other is so much lower. I think you should go in
with the right intentions. Your reputate, by the way, the only reason I think you
should be a good guy or gal and not invest in a competitor, is because your reputation is your equity. Like it’s selfish. It’s cause I want to be
able to invest in things in the future. And if I have a reputation
for constantly investing in my competitive stuff just
to win on short term money, I’m not gonna be able to get into deals. So I think reputation management in a transparent world matters. I think that is a dick
move, if you’re doing that. – Gotcha. – Is that basically
answering your question? – Totally makes sense.
– Why do you ask that question? Is that something you’re seeing out there? – Just kind of curious. I co-founded a startup with Max. Sometimes we kind of
run into that problem. People say no, they already
invested in a similar company. – And do you view them
as a direct competitor? – No, that’s the problem. Like on paper, they
see us as a competitor. But when you dive into it’s not. – Well that’s where you guys
just have to do a better job and educating people how it’s different. – Gotcha.
– Thanks. – I appreciate it, Gary. Thank you.
– Thanks guys. Guys, episode 28 in the bag.