Jason Calacanis, How to Monetize Your Personal Brand & Future Of Employment | #AskGaryVee 233
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on this episode, Jason Cal canIs stops by Harry B Promoting scary they nerd shock In this episode 2 33 of the Ask Gary Be Show two of my favorite people here. Jason Cal, canIs in India, India. Why are you even here? This is amazing. I'm excited. Elliot. Are you sad? Showed sad Elliot. Sad Elliot. I love it. India. Very good to see you. But, Jason, more importantly, for the four people that don't know who you are, why don't you give them a 30 to 75 2nd bio? I'm


a angel investor


that when you start with No, I started it. I say I say things all the time.


No. It started smoking a reporter here in New York. So I started a bunch of Internet companies, mainly in publishing. And I am an angel investor on duh commentator. I kind of like the West Coast version of Gary. Like the Knicks. Your jets?


Yep. Your ambition is to buy the Knicks. Like


seeing the garden. It's getting harder and harder.


We're not being more successful than the value of these companies are getting worse, but not fast enough. Well, the good news for me with the NFL is that ultimately has a decline with concussions and this and that. And so we'll see. But anyway, so what's been going on? A lot of a lot of people, you know, it's funny. I have a lot of young young young entrepreneurs and a little bit more like not old just tech, where you have enormous name. So I think for a lot of people look, I think from my standpoint, from afar and we've interacted a bunch, he just executing hustles. I like that very early Web 1.0 kind of entrepreneur.


I started when the Web WAAS no images, no video. The nineties here in New York. It was pretty exciting. We all knew it would get big, but


it took longer than we all thought, right, kids, right. Like by the year 2000 it felt like I remember wine library is going to sell all of its wine online library by the year


2000. To you know, this device, that chart was wrong. Unexpected game changer, game changer. Because we never expected you would have


brought. Didn't we find the video on wine library TV where I'm like you can use Twitter on your phone. Now we need to pull that out like you have it




about when one wants it. When did I say when was the video? From 2007 which is? And this is what, 2 33 way almost. That would have been great. That would have an amazing recall. But things change fast and just, you know, one of the few guys in that angel ecosystem that I grew up with that was smart enough to invest


in the angel round of uber. Yeah, one of things you learn about being an angel investor is you don't have to know if the companies don't succeed. You just need to know if the person's gonna Travis about it. And you just knew a Travis that he's into fatigue abo he's a hustler. He's hard working, and I passed on Twitter and single because I couldn't figure out the businesses. And that's what I said. You know what? I'm betting on? Horses. Exactly. Eddie Williams. Whenever they dio, you gotta just bet the person in the their ability


to figure it out. Talk about great people. Let's go to India, India. Let's get to the first question video. Rusty. Hey, what's up? Gary V. My name is Brian, a k a minor bond on the APP musically, and I have a following of over 600,000 people. Not only that, but I'm one of four musically 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 flat,

so I don't know what to do next. I I love making these videos now musically, but I'm also pushing everybody to YouTube to I asked this question because I have friends who have less followers of me who have managers and people who don't have millions of fans who don't. You don't even have managers. 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 a manager or what should I do? I put my business email off there, and I'm not always getting e mails every day or something. I am impatient. I do wait, but lately I'm just trying to figure out a way to get a source of income from this. Because again, I do love this. I love doing this,

but at the end of today, I still have my mom harassment saying a Are you gonna get a job or doesn't that? Yes. Oh, 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 than Twitter was really the first preview to this where both of us were lucky enough to be one of those 100 150 people that everybody was following. What kind of advice do you give to? You know, I'm paying a lot of tension to the musically stars is the youngest generation of stars. We think you're making a joke of boner media being young. We're talking about 9 10 11 12 year old stars since it's Nickelodeon up in musically right now. What's your what's your advice for this?


Well, I mean, what is the goal here like this? The person you want to be active, they actually brought out. Are they actually a musician? Are they actually a singer where they just kind of becoming popular for DUI? Do


you think that's becoming. Do you think that's possibly becoming just talent itself? Like, you know, it's interesting. 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 you learn an instrument, if you actually learn to sing, then you can kind of take it to the next level. So when you start Justin Bieber on YouTube, it was like, Yeah, he's a YouTube star but


he actually had a core talent. He was a real talent. He was


a real town. Then you look at somebody like King Batch. Yes. On Fine. Yes. Is the number one guy for a while. Probably still is like he actually is


funny. He cares. A real comedians. A real comedian. Actor? Yes, comedic actor. Yes, I


think adding skills when you're a young person is one thing that this generation backwards, they go get the fame, and it's great You could hit that lighting a bottle. But get that skill you could never You can never be taken away from you.


Yeah, I think I think networking. I think just even asking this question like, for example, Mom interested? I'm spending more time in musically, So let's get this kid into my office. I want to meet for 20 minutes, and you just need to do that over and over. 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 number because I know but you write and some people they e mail you one time and he had 15 minutes and some people have a 1,000,037,000 times, and I never talked to them. Exactly. That's That's the punch line quality I look for people with, You know, this. It's a subjective moment in time. Sure, like at that moment it felt like right? Yeah, it's a crapshoot.


Yeah, but you know what? It's a numbers game. If you One of the things is I had an investor have a portfolio company that raised money from seven people and, like we can't raise any more money. It's not working well. How'd you first like when we met with, like, a ton of people said 15. I was expecting money from 50% of you will be with And now you've been with another five You didn't get an investor So you're quitting psych so so soft You gotta do at least 50 meetings at what you do is you take notes after every meeting and you ask people candidly Why did you pass on investing? The way you could help me understand Your passing is just Can you just tell me the truth and to stand with me and tell me why I saw were telling what I need to work on? You know what? People will do it if you give them permission to


speak freely. Lovett, India Let's move it forward. By the way, I'm serious. I want to meet the kid. Make it happen


Phil. Manu, Gary. It's a Canadian homey swish. Had a question for you. Very short and sweet. What's your career? Advice to de rock and how he can progress his career because he the madly talented person and I know for sure you want the best


out of a great question up for me. I think the rock needs to hold on to me for dear life because I think he's grossly overrated because of the fame and stardom of my amazing ability. And so if I was Dirac, I'd be holding on for dear.


Life is just one of your


know That's the Rock, the Rock. So he is obviously filming Daily V, and he's got clearly he's got video skills and he's built in order. Now when I think of something,


let me tell you something about loyalty. It's your three and four with. Everybody wants to bounce after a year to go to the next day because somebody could go. Oh, do you rocks associate with him? Let me give him a 10% bump in salary jump over there. But I'm


telling you for 100 when you're making two bucks an hour.


But I always find the people who stick around for your 345 and a start up. They kind of ascend to this level. They learned some stuff, and you want to learn when you're young and the problem is, a lot of people don't put the time they


quit too early. I think the big thing is, um, you've got I agree in some ways and I'll go slightly different. You just have to reverse engineer. What? You gotta deploys much self awareness as you have this moment and reverse engineer what you want. If Iraq wants, For example, if the Rock wants to make a movie for real, write a feature film. He's never been in a better position with me because it was 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 future. I could find a feature film now raising money like I don't want to know what Dirac. But you know, I think I think,

but you just have to know what you want. I think I think that my career advice manner to you to d rocked India, Thailand Annie, 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. India. But you're in the game. That's important. Yes, crazy,


crazy video a minute before reveille. No, Jock. You remember when Episode three You said it should be a life dream to get your question on my show. It's my life treatment. Please, India. Come on, girl. Get me on the show. Just getting India. You're awesome. I love you. Hey, I'm really glad you didn't get fired. Way worried. We were worried bein a nation was worried.

Hey, dear up cameras get together and focus. I'm sick. Freak coming from you from Valparaiso, Indiana. Cornfields and everything. Oh, God, help me. I need a mountain. Somebody give me a mountain. I'm a personal trainer and a lifestyle manager. Oh, that's a new one. Lifestyle manager. What does that even mean?

I'll tell you, but let's let's just get to the question, okay? No, we're really I love what you're saying about self awareness is one of the number one things. I talk to my clients about one of the number of things that has changed my life for the better in so many different ways. But being truly self aware, I know that one of my best talents, obviously, is the energy that I bring to the table. And I'm telling you I'll bring this energy of the table wherever on that. Okay, call me out there right now. I'm gonna drive out that You think I won't? I will bring this energy, Gary.

And I know this would 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 and an emotion that comes through the energy that I developed 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, Iraq. Lincoln description. Oh,

get right there. Right there. Live life guy and go New York. Jack. Jason, what do we owe? Thanks. Jim Carrey. He's really, really That's really got some interesting charisma. What do you think? How does he monetize


all that energy? Well, here's something way both know online is a great way to get attention. It's It's a little bit challenging sometimes to monetize. I was CPM very low. It's hard to get to the brands. That's why big agencies like yours exist in other ones. around town. They have the brand relationships. So be some opportunity to join these networks of stars. You know about those? Yep, 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 in the role paying 50 bucks an hour what I was finding, people are afraid to raise their prices on lose clients, right?

So if he keeps growing and he's that good, you know, we should go to races, doubles price, then double your price, then double your price. And, you know, maybe have five people who are paying $400 a session where that kind of thing. So be good at whatever your skill is, and they keep raising your price


products Service's content. There's only 4 to 5 things that one can hear to monetize. You've got great energy. You get intention you get, you get, you build a base, and then you could do a lot of different things. You could sell them stuff right? Make a product for you. You can sell a T shirt like you can sell them a physical thing you can create a service. If you train people in its 50 bucks an hour, that's 102 100. You can be in a place where you as a personality gets monetized. You signed a book deal. You sell a lot of them. You speak for 100 bucks than 1000 bucks and 5000 bucks you create Ah, scalable content play.

You put out something that is, you know, you put your classes on you, Demi and all these kind of things collect creative, collective and things like that. So you and I can give you like a lot of things. But like the truth is, there's only like five or six things that are out


there. Rookie mistake. When I talk to somebody, say, What's your business model? And they say, Well, it's gonna be advertising and subscriptions and they're going to sell things And then we're gonna sell the data and they list 18 things, and it's like, Whoa, whoa, whoa! The great companies uber take a percentage tumbler. Advertising Google Ad Network is very rare that you see even a big company Apple selling hard work goes into a second or third business you have to pick one and go see it 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 your category, and you have to have great tight relationships have to deliver for those advertises 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.


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 like try different things. See what? Yes, Seems


like what you enjoy. Yeah, I think so. Critical to because you don't enjoy being in the service business. Having customers like you can't do it. You're


all like tech friends as you like, you know, like like from what I came from, like you like this, like you like having them like I'm like, I like it because I know what it's building for me long term, but it's you know, like nobody in Tech wants the unstable nature of service. Nobody


know if you look at real clients and look at the knowledge you're getting heels out here like the different.


I don't think I don't think you know what I think that's a popular conversation. I think people pretty basic do they like, Yeah, I think that they have 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're more power because the world has gone in their favor there, 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 what


they're looking at you that they're like I could be him and I could do what he does.


I hope not. Because then they're fucking stupid.


Yeah, I think they're looking at I think I'm looking around the room. I think a lot of her life,


you know what's funny. I hope they feel that way, but they won't happen. All right, let's go. What's up, Gary In team had the use of here off of your inspiration. I started blogging my startup journey. I've been interacting with online communities like the great Vader nation and just making sure that I'm putting out good content. But aside from patients 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 jump and Jason is I think more real life stuff like ABRI meet up like Like Jason might remember this when I first got I mean, it's really fun to get your perspective This When I first came into the ecosystem, I was pouring wine at a joy ICU. Leo Laporte, meet up one guy?

Yeah. I mean, I was like, I I was service. I was to help,


basically. I mean, I don't want to say, but it's kind of


true. And so and so like, we need one here. I mean, a new ally. I mean, while I had the biggest business in the room, everybody else have business on paper, actually on a business, but I was willing to earn my keep into the ecosystem. That's the advice I would give here, which is if you're documenting your journey. Amazing. But goto every Israel's such a hotbed for tech start ups and just start ups in general. Goto every meet up, meet every person, be part of the ecosystem. I think you did that extremely well. That's


right. When I started looking reporter, here were a silken, our reporter shirt every day, 20 of them. So I was the brand, and I would show up at every party, and I have copies of the magazine. You have to be the brand, and you have to be everywhere. But a little act for him might be be the most intelligent question. Under the most important people's block posts were their tweets. In other words, really Take your time. Forget about building your own content, your own audience. Find somebody who's got an audience that you would like to acquire and be the most intelligent person in there for a while.

We just kind of what you did. Like you meet the guy like this guy's passion or wine, but I'm here to see Leo, but this guy's also kinda interesting to write and So if you can put yourself in Fred Wilson's comments on ABC, it's like


people. You know what? I really think this is really smart, especially in the Facebook we go system 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 car. That's the problem of the people are trying to build a brand. They're


pitching instead of bringing value to the community of the micro community within that blonde post. Correct? Yes. What


is the topic we're talking? And how did you say something?


And to your 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 blog's that are just like you. Entrepreneurs are trying to make it than us reading it. And so so you saying Here's my perspective from an Israeli lead startup that from a 23 year olds perspective, you'll get a lot of juice for that. You need to own it There's way too many people trying to fake the funk right now that they're so genius. Business people and I have no experience under her fingernails.


There's nothing Maur like, I think, appealing than somebody who's a young entrepreneur saying I really don't understand how this works. Did somebody explain it to me or help me? Because I really would like to be successful. People will come out


and help one 100% if you deploy the humility and don't fake it. Well, everybody doesn't way. I've been there like like when you don't when you're not there yet. You kind of wanna You want Isis saying yes and this and it was just not smart. I should have said, Please tell me in this now got there faster


in my meetings. Anytime a word comes up that I don't know, what does that mean? This is meeting


and I wouldn't even have meetings that because I'm terrible at, like vocab you had, like


something like, Oh, do you know about this? And what is that? And I just explained to me what that is. It's an acronym for this, and now I'm getting smarter.


100% Andy, Let's move this. I know we got it. I got a call. Last one. That's cool. David. Whoa! Hey, this is David Villa in Tampa. Ford on the CEO of I P D. And hey, Gary, I got a question for you. How do you deal with the sacred cow or the top performer in your business? That generates a ton of business, but it's toxic to your company.

Culture fired, Fired, Fired. David Fire! David, Let me Do you have anything else? Top fired even before he finished, right? Good guess. Fired, Fired, Fired. Fire! 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 just gonna cap out. It's like it's like math based marketing. Eventually you run out of time and, like you can only extract


so much. You know what it's like. You know, you have something like J. R. Smith on your team and like he's eventually going to implode and cost you a championship. Well, like


J R. Smith Jr Smith as the number one on that team. When the top performer is toxic, you are finished. Thea other thing, by the way, is you have to be the most. You have to be the top performer, like like, to me. That is the number one thing that I've always loved about my businesses, which is like, I don't know, I just don't rely on anybody at like I could never imagine running a business, that I would sit there and say If de Rock were


you scared You scared about quitting because he's the top


100%? That's what you see. The fear You wouldn't even ask that question. There's a boy away in a car salesman world. There's a 1,000,000,000 great car says, by the way, in the comment section, If you're tremendous car salesman and up for moving, leave Akane, Jason, get to ask the question of the day. Any question you want. Great focus Group of hundreds, if not thousands of answers inside of Facebook and YouTube. What's on your mind, too young entrepreneurs and business peeps and social media peeps. What do you curious about these days when he looking at us?

You're You've been a very successful investor. You've been absolutely historically correct on trends, even the people that love to razz you and things that did not deny the fact that you've seen things play out properly with your business behavior could not Yeah, way as people that have put themselves out there, You get your pros and cons of that like nothing trumps the resume. Having winds helps its air


cover. As I tell people when they criticize, I'm just a guy who got lucky times just a just eight times. But, you know, like at a certain point, if you just keep hustling and you have one of those Windows


number really three or four Need me? Like like really? Like I'm imagining you show about.


Like so for example, please, an LP and a fund? Yes, that fund soccer. I can't say which one it wasn't, but it was in that stock certificate up there. Got it. And it wasn't. What's that? Yep. And I just got a call one day and they're like, by the way, you have these two huge wins. I don't know how those winds, but somebody get I gather things happen. I just sold my book. I'm doing a book on angel


investing and Hollis. Look, Hollis, I know. I just So you know a little, but not only that, little behind the scenes. I get calls from Hollis once in a while. Like, what's the story here? And usually I'm like And this and I'm like on this one. No, no,


she was like Carrie went


And you guys know I hate to go to bat for sure. No, India. I don't go back.


Okay, so my question for body is What do you think the future is of employment now that we have robotics and a I A mortar solutions. If in fact, we see a lot of jobs go away, how would you solve the problem of a society with, let's say, 20% less jobs available, which would increase unemployment, which, you know, we say the number three or 4% right now, but it really does include people who gave up, which is another 15%. So what if we lived in a world where the majority of people couldn't find a job? Only half the people employed. How would you try to solve for that creative way? Because in our industry we debate this, but we all and in the past we always come up with new jobs, but it feels like this could be the difference.


Joe Bide I was at an event where Joe Biden spoke. I don't and reason I'm name dropping is because maybe maybe because he's got a quote out there that could somebody can make this completely tight because I could be wrong. I don't remember if he said it's the number one job in America or the number one job. Now we're calling for people that do not have a college degree. But whatever the punch line is and again, somebody leave a comment for clarification. He said the number one job in the marketplace is transportation. Driver's right, and he goes with this looming, this is the number one job people have and I'll actually write Cap. That's right, you know? Yeah. I mean, listen. And by the way, that's what happens in industrial revolutions like shit's


about to hit the fan. And what is the solution versus open?


That's a big question. One coming


out. He's gonna come back next summer. Yeah, let me know when you tweet here.


They're well, have you asked a question and we'll link it up. I know you're fundamentally blown away by the youth of this organization. I have


never seen an organization this young. I'm looking around the room. That kid's definitely


in high school things get Tyler. How old? Tyler banging? 19 said He's got


this kid's 21. Yep. Back kids 25.


Yeah, looking 26. She told you that? This How are you? I'm 45. Nice number. Put it this way. You and I can hear the oldest people here. No, I get it. I know you keep asking questions will keep answering them.

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