#AskGaryVee Episode 233: Jason Calacanis, How to Monetize Your Personal Brand & Future Of Employment

My name is Bryan AKA MindofBun,
I’m on the app Musical.ly and I have a following of
over 600,000 people. Not only that but I’m one of
four Musical.ly reps that live in New York City. So my question is
I don’t know what to do next. I feel like I’m
stuck in a plateau. I don’t know what to do next. I love making these videos,
not only on Musical.ly but I’m also pushing
everybody to YouTube, too. I ask this question because
I have friends who have less followers than me who have
managers and people who I know that have millions of fans who
don’t even have managers or they don’t even know what to do. So, what should I do
next with this following? Do I go out there and look
for companies or brand deals or should I link up with the
manager or what should I do? I put my business email out
there and I’m not always getting emails every day or something. I am patient, I do wait but
lately I just trying to figure out a way to get a source of
income from this because, again, I do love doing this, I love
doing this but at the end of the day I still have my mom
harassing me saying A, are you gonna get
a job or this and that? And yeah, so Gary
what should I do? – Jason, it’s fun to have
you here with this question. Good job by you guys curating
because again we lived through early bloggers getting famous–
– Sure. – then Twitter was really
the first preview to this– – Sure. – where both of us were lucky
enough to be one of those 100, 150 people that
everybody was following. – Sure. – What kind of advice do you
give to, I’m paying a lot of attention to the
Musical.ly stars. – Sure.
– This is the youngest generation of stars
we’ve ever seen. You’re making a joke of
VaynerMedia being young,– – I know. – We’re talking about 9,
10, 11, 12-year-old stars. – Yeah. – Like it’s, it’s Nickelodeon
up in Musical.ly right out. What’s your advice for this? – Well, I mean what
is the goal here? Does the person want to be, do they actually
have any raw talent? Are they actually a musician? Are they actually a singer or
are they just kind of becoming popular for doing– – Do you think that’s possibly
becoming just talent in itself? – That’s a good question. – Like you said that and
I’m debating it myself. – Right. Do you
actually have a skill? So what I think is adding skills to your repertoire like
that can only help you. So if learn an instrument,
if you actually learn to sing then you can kind of
take it to the next level. So when you saw Justin Bieber
on YouTube it was like, “Yeah, he’s a YouTube star but
he actually had core talent.” – No, he was a real talent.
– He was a real talent. Then you look at
somebody like King Bach. – Yes.
– On Vine,– – Yes. – he was the number
one guy for a while. Probably still is.
He actually is funny. – He’s a real comedian.
– He’s a real comedian. – Actor.
– Actor. – Yes.
– He’s a comedic actor. – Yes. – So I think adding skills when
you’re a young person is one thing that this
generation got backwards. – That’s a good point. – They go get the
fame and it’s great. You can hit that lightning in
a bottle but get that skill you can, it can never be
taken away from you. – Yeah, I think networking. I think just even asking this question like, for example,
I’m interested. I’m spending more time in
Musical.ly so let’s get this kid into my office, I want to
meet him for 20 minutes. And you just need to do
that over and over, right? – Yeah. – How many people have been able
to get to you and met for 15 or 30 minutes just by pounding you on social and email
through the last decade? Give me a rough estimate of
numbers because I know– – Over a thousand.
– That’s it. – Over a thousand,
it takes time. – You, right and some people
they email you one time and you gave them 15 minutes and some
people have emailed you 37,000 times and you’ve
never talked to them. – Exactly.
– That’s the punchline. – I look at the quality like I look for people with
skill but that’s me. – But you know this, it’s a
subjective moment in time. – Sure. – Like at that moment
it felt like, right? – Yeah.
– I mean it’s a crap shoot. – Yeah but you know what? It’s a numbers game, if you,
one of the things is I had, I have a portfolio company that
raised money from seven people and they’re like we can’t raise any more money,
it’s not working. I’m like well, how’d
you get the first seven? They’re like well, we
met with a ton of people. I said how many
people did you meet? They said 15. I was like so you can raise
money from 50% of the people you meet with and now you met with
another five, you didn’t get an investor so you’re quitting?
– Soft. – So soft.
– Soft! – You got to do at least 50
meetings and what you do is you take notes after every meeting
and you ask people candidly why did you pass on investing? The way you can help me,
I understand you’re passing, can you just tell me the truth? – Interesting. – Be candid with me
and tell me why I suck. – I love that.
– Or tell me what I need to work on.
You know what? People will do it if you give
them permission to speak freely. – Love it. India,
let’s move it forward. By the way, I’m serious,
I want to meet the kid. Make it happen. – [Jason] Hey-o!
– Manu.

– Hey Gary. It’s your Canadian homey Swish. I had a question for you, very
short and sweet, what’s your career advice to DRock and
how he can progress his career because he’s a madly talented
person and I know, for sure, you want the best outta him. – Manu, great question. For me, I think DRock needs
to hold on to me for dear life ’cause I think is grossly
overrated because of the fame and stardom of my
amazing ability. (DRock laughs) And so if I was DRock,
I’d be holding on for dear life. – Is this one of
your whack packers? – No, that’s DRock. – That’s what I said,
one of your whack packers. – So DRock, he is obviously
filming DailyVee and he’s got clearly, he’s got video skills
and he’s built an enormous– – Yeah. – Now when I take a selfie–
– How long as he been here? How long you been here, DRock?
– [DRock] Two and a half years. – Alright, let me tell you
something about loyalty. It’s year three and four
when the magic happens. – Interesting. – Everybody wants to
bounce after a year or two, go to the next thing.
– [DRock] Yeah. – ‘Cause somebody’s gonna go, “Oh, DRock’s associated
with him? “Let me give him a 10% bump in
salary to jump over there.” But I’m telling you– – Or 100 when you’re
making $2 an hour, you know. – Yeah, exactly. I always find that people that
stick around for year three, four, five in a startup they
kind of ascend to this level and they learn some stuff and you
want to learn when you’re young. And the problem is a lot of
people don’t put the time in. They quit too early. – I think the big thing is,
I agree in some ways and I’ll go slightly different. You just have to reverse
engineer what, you got deploy as much self-awareness as you
have of this moment and reverse engineer what you want. If DRock wants, for example, if DRock wants
to make a movie, for real. Right, a feature film, he’s
never been a better position with me because as long as he
keeps believing in me and as long as I keep proving that
I continue to grow I’m closer to being able to fund a feature,
I fund a feature film now. – Sure. Why not? – It’s like raising money. I don’t want to.
No way, DRock. (DRock laughs) But you just have to
know what you want. I think that my career advice
Manu to you, to DRock, India, Other Tyler, Andy, to Jason, to
myself is know what you want and put yourself in the best
position to succeed to get there but be careful because the
thing right in front of you is normally not the thing that’s
actually going to get you to the best position to
actually do what you want. – Hmmm. There you go. – India.
– But you’re in the game. That’s important.
– Yes. – [India] You ready
for a crazy video?

– Gary, Gary,
Gary, Gary Vaynerchuk! Hey you remember when episode
three you said it should be your life dream to get your
question on my show? Gary, it’s my life dream, man. Please, India!
Come on, girl. Get me on the show. Just kidding,
India, you’re awesome. I love you. Hey, I’m really glad
you didn’t get fired. (laughs) We were worried,
we were worried. Vayner Nation was worried. Hey, DRock, can our cameras
get together and focus? (laughs) I’m Zeek Fit Freak coming
from you Valparaiso, Indiana. Cornfields and everything.
Oh God, help me. I need a mountain. Somebody get me a mountain. I’m a personal trainer
and a lifestyle manager. Ooh, that’s a new one.
Lifestyle manager. Ooh, what does that even mean? Well, I’ll tell you but
let’s just get to the question. Okay? No but really, I love what you’re saying
about self-awareness. It’s one of the number one
things I talk to my clients about, one of the number one
things that is changed my life for the better in so many
different ways but being truly self-aware I know that what my
best talents obviously is the energy that
I bring to the table. And I’m telling you,
I’ll bring this energy to the table
wherever I’m at. Okay? Call me out there, right now. I’m gonna drive out there.
You think I won’t? I will bring this energy, Gary. And I know this will be really
great for brands but I’m trying to brand my own thing
on the side, right? So the question is
how do you harness an emotion that comes through the energy that I develop and give and
share with other people? How can I monetize that online? I’ve been working on it and
I could really use your help. Thank you so much, Gary. I love you, man. Hey, DRock link in
the description. Ooh, get right
there, right there. Lift life guys and
go New York Jets! Woo! – Jason, what are
you doing with that? (group laughter) – Wow, it’s like Jim Carrey. – He’s really, really, that’s
got some interesting charisma. What do you think? How does he
monetize all that energy? – Well, here’s the thing,
we both know online is a great way to get attention. It’s a little bit challenging
sometimes to monetize. Obviously, the
CPMs are very low. It’s hard to get the brands,
that’s why big agencies like your’s exist and other
ones around town. They have the brand
relationships, so they’ll be some opportunity to join
these networks of stars, you know about those.
– Yep. – And that’s a fine way to do it
but I think building your brand online and then
increasing your prices offline. So if he’s a trainer and he’s
got five clients and they’re all paying $50 an hour, what
I always find is people are afraid to raise their prices
and lose clients, right? So if he keeps growing and he’s
that good, he should be able to double his price. Then double your price, then
double your price and maybe have five people who are paying $400 a session where
that kind of a thing. So be good at
whatever your skill is and then keep raising your price. – Products, services, content.
– Yeah. – There’s only 4 to 5 things
that one can do to monetize. – Sure. Yeah. – You got great energy, you get
attention, you get you build a base and then you can
do a lot of things. You could sell
them stuff, right? – Sure.
– Make a product, yep. You can sell a T-shirt like you
can sell them a physical thing. – Yeah.
– You can create a service. If you train people and
it’s 50 bucks an hour then it’s 100 and 200,
you can be in a place where you as a personality
gets monetized. You sign a book deal,
you sell a lot of them. You speak for 100 bucks then
1,000 bucks then 5,000 bucks. You create a
scalable content play. You put out something that is,
you know, you put your classes on Udemy and all
these kind of things. – Yeah. – You collect, Creative
Collective and things like that so you and I can give
you like a lot of things. But the truth is only five or
six things that are out there. – It’s always the rookie mistake
when I talk to somebody and say what’s your business model? And they say well, it’s going to
be advertising and subscriptions and then we’re gonna sell things
and then we’re gonna sell the data and they list 18 things. It’s like, whoa,
whoa, whoa, whoa, whoa. The great companies,
Uber, take a percentage. Tumblr, advertising. Google, ad networks, right? It’s very rare that you see even
a big company, Apple selling hardware, goes into a
second or third business line. You have to pick
one and master it. – Go deep. – And just master it because
you know how hard it is to get advertising and content to work. You have to be the number one
person in your category and you have to very tight relationships and you have to
deliver for those advertisers. On a product basis, people who
are making great products and selling them at a high profit
like Apple, man, it’s hard to compete against
people like that. You have to be
exceptional in this nature. – The other thing for a lot of
you that are watching that I think will be valuable
is try to do everything. Give a free speech. Create a content e-book. Go try to get a publishing deal. Try different things. – And see which ones pop.
– Yeah. – And which one you enjoy.
– Yeah. I think so. – That’s critical to because
if you don’t enjoy being in a service business and having
customers, you can’t do it because you’re gonna
hate your customers. – Oh my gosh, all my
tech friends as you know– – Yes. – Like from what I came from,
they’re like you like this? You like having–
– (sighs) Brutal. – I’m like I like it ’cause
I know what it’s building for me long term.
– Yeah. – You know like nobody in tech wants the unscalable
nature of this. – Of a service business.
– Nobody. – No.
– Nobody. – But if you look at it, you
have real clients and look at the knowledge you’re getting. You have all these Millenials
out here and they’re different, aren’t they?
– I don’t think so. – Maybe different
than Gen X’ers. – You know what, I think
that’s a popular conversation. I think people pretty basic.
– Yeah? – They the same tried-and-true
things which is they have some balance of their
wants and needs. I just think that
they have more power. – They do. – They have more power because the world has
gone in their favor. They’re 20-something in a
time where 20-somethings are respected by 40, 50 and
60-somethings around business because business
is being done here. And they know it better. – Do you get the sense when
they’re looking at you that they’re like, “I can be him
and I can do what he does.” – I hope not because then
they’re fucking stupid. – Yeah. I think I’m looking
around the room, I think a lot of them are like
I could be in charge. – You know what’s funny,
I hope they feel that way but it won’t happen.
(group laughter) – It takes time. – Alright, India, let’s go.
(group laughter) Hadi Yousef here.
Off of your inspiration,

– What’s up Gary and team? Hadi Yousef here.
Off of your inspiration, I started vlogging my
startup journey. I’ve been interacting with
online communities like the great Vayner Nation and
just making sure that I’m putting out good content. But aside from patience and
thinking about the long game, what are some things that
someone like me should be doing to grow his audience?
Thanks a lot. – So I think one thing that
stands out for me and then you’ll jump in Jason is
I think more real-life stuff. Like every meetup.
– Sure. – Like Jase, you might remember
this, when I first got, it’s really fun to get your
perspective on this. When I first came
into the ecosystem,– – Yeah. – I was pouring wine at a
Jaiku, Leo Laporte meetup. – Yeah. You were the wine guy.
– Yeah, I was– – You were more
like, who’s that guy? – I was service.
I was the help. – Basically, I mean
I didn’t want to say it but it’s kinda true.
– And so like– – They’re like we
need wine here. – And meanwhile, and meanwhile I had the biggest
business in the room. – For sure. – Everybody else had
business on paper. – Yeah. – I actually had a business but
I was willing to earn my keep in to the ecosystem. That’s the advice I would
give here which is if you’re documenting your journey,
amazing but go to every I mean Israel is such a
hotbed for tech startups and just startups in general. Go to every meetup,
meet every person, be part of the ecosystem. I think you did
that extremely well. – Be everywhere.
– That’s right. – When I started Silicon
Alley Reporter here I wore a Silicon Alley Reporter
shirt every day. I had 20 of them so I was the
brand and I would show up at every party and I’d have
copies of the magazine. You have to be the brand and
you have to be everywhere but a little hack for him might be is
be the most intelligent question under the most important people’s blog posts
or their tweets. In other words,
really take your time. Forget about building your own
content and your own audience, find somebody who’s got an
audience that you would like to acquire and be the most
intelligent person in their ecosystem for a while.
– Love that. – Which is kind of what you did. You’d meet the guy you’d be like
this guy is passionate about wine but I’m here to see Leo
but this guy’s also kind of interesting too, right? And so you can put yourself in
Fred Wilson’s comments on AVC it’s like who are these people writing highly
intelligent comments? – You know what this is
really smart, especially in the Facebook ecosystem where if it’s
actually that, it populates up. – Yeah, they trend it up.
The best comment goes up. But this takes time and you
have to not be thinking about yourself with your comment. That’s the problem I think. People are trying to build a
brand so they think it’s about– – They’re pitching instead of
bringing value to the community of the micro community
within that blog post. – Correct.
– Yep. – What is the topic
we’re talking about– – Yep. – and how do you say
something highly intelligent and further the conversation? – And to you, because you
don’t come from 20 years of experience, 30 years experience
you need to put your lens on it. By the way, there’s a lot of
people reading comments on those blogs that are just like you,
entrepreneurs are trying to make it than us reading it. – We’re not
reading the comments. – So you saying here’s my
perspective from an Israeli led startup that from a
23-year-old’s perspective, you’ll get a lot
of juice from that. You need to own it. There’s way too many people
trying to fake the funk right now that their so genius
business people and they have no experience under
their fingernails. – There’s nothing more, I think,
appealing than somebody who’s a young entrepreneur saying I really don’t
understand how this works. Can somebody explain it to me or
help me because I really would like to be successful? People will come
out and help you. – 100% if you deploy the
humility and don’t fake it. – Yeah, there’s no
reason to fake it. – Well everybody does it.
And by the way, I’ve been there. When you’re not there yet,
you kinda wanna, you want to, I used to say yes and this.
It just was not smart. I should have said please
tell me and this and that. I would have got there faster. – In my meetings, any time a
word comes up that I don’t know, I say, “What does that mean?”
In a business meeting– – I wouldn’t even have meetings
then I’m terrible at vocab. – No but when you have to pitch
and someone’s like oh do you know about this?
And I’m like what is that? And I just say explain
to me what that is. And they’re like oh
it’s an acronym for this. And now I’m like now
I’m getting smarter. – Yeah. 100%.
– Right? – India, let’s more this.
I know we got a call.

– Hey, this is David Villa in
Tampa, Florida. I’m the CEO of IPD and hey Gary,
I got a question for you. How do you deal with the sacred
cow with a top performer in your business that generates
a ton of business but is toxic to your
company culture? – Fired! Fired. Fired, David. Fired, David! Does he have anything else? – [India] Eliot and I thought
you were gonna say that. Tox, fired.
– Yep. – Even before he
finished, right? Good guess. Fired. Fired. Fired.
– Yeah. – Fired. – It’s fired.
– It’s fired. – Life is short,– – It’s not even about like
living your best life and life is short.
It’s you lose. Like, you lose. Like you’re just gonna cap out. It’s like math-based marketing. Eventually, you run out of time. And you can only
extract so much. – You know what? It’s like, you
know you have someone like JR Smith on your team and he’s
eventually going to implode and cost you a championship. (crosstalk) – No, no, JR Smith, JR Smith
as the number one on that team. – Yeah. – When the top performer
is toxic, you are finished. – It’s game over, yeah. – The other thing, by the way is you have to be the most, you have to be
the top performer. To me, that is the number one
thing that I’ve always loved about my businesses
which is, I don’t know, I just don’t rely
on anybody. I could never imagine running a
business that I would sit there and say if DRock quit. – He’s scared of that
guy quitting because he’s the top salesperson.
– 100%. – That’s what, I can
see the fear in his eyes. – 100%. – If he wasn’t he’d be like
well, I’ll just do the sales. – He wouldn’t even
ask that question. By the way, in a
car salesman world, there’s a billion
great car salesmen. By the way, in the comments
section if you’re a tremendous car salesman and up for
moving, leave a comment. – Absolutely. – Alright, Jase, you get to
ask the question of the day.