How You Can Spot Trends Before Everyone Else | The OGs Podcast

0:00Welcome back to the OG's of Playmaker Original presented by DraftKings and we have a very special guest in the building today. A lot of people don't know what we in. When me and Mike talk about doing podcasts, we didn't want to do athletes originally. You know, we want to kind of stay away from athletes. You understood? We know sports. We can talk about sports all day. So this is a very special opportunity for us. He built a$60 million wide business, serial entrepreneur, investor who built on Facebook, Snapchat, Twitter early. He runs a media empire. I'm not even going to bring that jet stuff.

0:33We're going to go for the jet stuff. Gary Vee in the building, ladies and gentlemen. Thank you, my man. Thank you, my man. It's a pleasure to be with you. So, I mean, we got a lot to cover, so this is very exciting. I very rarely have people on that I can learn something from. I mean, we have a lot of athletes on. Athletes can't tell me shit. I get it off my head. I mean, I know a lot about that. But for me, obviously, being born in the Soviet Union, what was life like? Because I know where I'm from. I'm from Liberty City. We think we got it rough. Tell me what rough really is. You know what's funny is I think about that a lot.

1:06Because I grew up, so I moved to the States when I was three and a half, four. So I didn't really live in the shit my parents lived in either. But when we came to America, we were broke. You know, I lived in a studio apartment with five, six family members in Queens. And then I grew up in Edison, New Jersey, went to Martin Luther King Elementary School. and so and then I was a terrible student and went to a straight up hood college Mount Ida College where all my boys were on financial aid came from this fucking hood hood and I was just telling you off camera one of my boys just turned 50 we're up in Brockton like real shit and it was funny growing up in that culture and I was a Jersey boy east coast 80s 90s urban culture was getting so cool you know having my adidas with no laces in sixth grade was the apex of my life and because of the stories my parents told my parents didn't have my both my parents grew up in a house that didn't have a bathroom in the house like they had to go to the outhouse like the soviet union in the 50s 60s 70s was like america in the 20s 30s and 40s and so and then my parents raised and i was the oldest from the old country.

2:27I have two siblings that were younger. What I got brought up with was a real framework of just being grateful for what we had versus being envious for what you don't have. As you know, especially growing up in sports, your situation I know enough because I'm a big sports fan. I know a lot, you know, a lot of guys grow up with so little. And there's only two things that happen when you grow up so little. You either become grateful for what you have and become hungry and ambitious, or you become cynical and you get fucked up and you get angry and you let jealousy and envy become your fuel. So I got lucky in that I wasn't jealous when on Christmas all my friends around me got more.

3:15Because even as my family was growing out of poverty into a middle class life through my childhood, my mom kept it real fucking poor. She didn't buy, like, my mom wasn't in the business of buying shit. Money was for food, even clothes. My dad worked at a liquor store from second to eighth grade. Every t-shirt I had was fucking Hennessy Budweiser. Like, like we didn't buy clothes. We definitely didn't buy soda because my dad got it from the liquor store like we just didn't spend money so real quick by the time I was seven eight if I wanted toys and then definitely by sixth grade when Nintendo came out video games my mom was on some gangster shit of like like yeah on your birthday maybe I'll get you a little something I did not get toys in my childhood outside of my birthday or Hanukkah it just did not happen.

4:13And so it made me hungry. I started selling lemonade when it snowed. Instead of making a snowman, I was like, fuck it, grab a shovel, get three bucks, get five bucks. And so it was obviously how my life has turned out. I was entrepreneur from the get. It was written. But I put in the reps as a kid because of my circumstance. My son is an entrepreneur. I can see it in him. But he's not, he's sitting courtside at a Knicks playoff game. My first sticks game was the last row in the arena. You know, going crazy for Bernard King. Last row. So, you know, people that are listening, of course it's nature nurture.

4:55Of course we all got our DNA and then we got who are our parents? What was the circumstance? What was the neighborhood? When I think about my success, I think about first my mom, she built me on some real shit. you know what I mean? Like she really built me like that. Next, the next place, and of course my father too, but he came later. I'll get to that in a minute. But the next place I go to why I got to where I got to is Edison fucking New Jersey. I believe the terroir, I grew up in the wine business. There's a term called terroir. It means like where the wine comes from, but it's not just location.

5:36It's like bigger than that. It's like religion. It's like the fucking bees that buzz around there. You see what I'm saying? Like the fact that there was a factory and the fucking smoke, like the whole essence of the place, not just the physical location. I credit the terroir of the 80s in New Jersey as making me because how old are you? Perfect. I'm 49. I'm about to be 45. Respect. 44. Hold it. Hold it. You know, we grew up in those 80s, early 90s. Like, you know, the reason so many kids talk so much shit these days is because people don't fight like they used to.

6:20It's real. These kids are keyboard warriors on Twitter because there's no ramifications. I used to walk the hallway. You look twice before you said some shit about someone. Because if you said some shit about someone and they saw it, it was flagpole. in fourth grade in my school we were like fucking UFC and Don King. There was pay-per-view every second day after school flagpole. When you said it was named Martin Luther King you already knew. Only Martin Luther King's is in here. Ain't no motherfucking Martin Luther King's in Beverly Hills. You said Martin Luther King's school? And I got real and I'll tell you where I got real lucky.

6:58My Martin Luther King, yes Martin Luther King schools are where they're at but we had some real diversity. I found my second grade picture. I didn't even remember. You know, you got that lower class white kid but we had Asian kids, we had Indian kids, we had black kids. Later when I got older, I think again, it's in me because I love people to get along with people but in hindsight, I got lucky. Like when I went over to my friend Brian Chen's house, I got exposed to that Asian culture. You know, when I went over to my friend Rasheed's house, like his mom was half in he was half black half indie like when i look back i'm like oh shit i got real real lucky and then my parents really tipped it off and in high school i moved to rural rural rural new jersey like straight hunting like i first grade first day of eighth grade uh i moved in eighth grade right before high school it was like the ninth day of school i walked in there was not a single boy in school i was like yo what's up with this hickville boys don't have to come on Fridays.

8:01My homeroom teacher said, what are you doing here? I'm like, I'm confused. Where are the guys? Because the girls were there. He's like, bro, it's the first day of hunting season. Oh, shit. I was like, what? Because Edison didn't have no rifles and deer and shit. So I just got very fortunate in how I grew up. How do I think about the Soviet Union? How do I think about my childhood? Adversity is the foundation of success. Wow. That's how I think about it. You talk about the hustling You said you were shoving snow Lemonade Trading cards, blow pops All the shit we all know Bracelet Anything that could Because you know You can't be hungry when you're fed Can't be hungry when you're fed Like that Can't be hungry when you're fed But fuck When you're not fucking That's real shit The fuck is that, I'm always whining and complaining.

9:01You can't be hungry when you fuck it. It's true. By the way, I don't even judge kids. Like, I don't judge it. It's their reality. In fact, I admire the fuck out of rich kids that go hard. I actually think they got a different year altogether. You know, those kids, for kids like you and I who built our shit, we got judgment for those kids. Born on third base, all that shit. But in real talk, now as I'm getting older, I'm like, damn man, I actually in a weird way respect those kids that go hard because they, it's almost like they're playing a game they can't win regardless. You imagine, listen, you and I have lived our lives.

9:39I'm sure of it that both of us will confirm to all these kids watching right now, we're grateful that we were in our spot because we were too competitive and hungry that if we were our kids and people could take away from us on some bullshit, just semantics, that would hurt. I've worked too hard for shit to be taken away from me and now that I've lived a little bit I've watched kids that had a lot that really worked like that that really fought off that really tried I mean I see it in my own children they're the only two that don't really fuck with Gary V like that they're trying to be on their own two feet I respect it I've seen kids change their last names I've seen kids like and you know when I was growing up, I had so little, I was like, man, that'd be that.

10:25Why are you doing that? You're so lucky. In reality, if you're a winner, the last thing you want to do is be a, put in a position where your work is undermined because of where you started. You just gave me, you just made a great point because you said, you know, you're two kids up and everybody fucking with Gary V besides your two kids. And the same thing with me, I got three boys and it's like, I feel like I'm the coolest dad in the world. of course look at you i can't give you advice who can you go to of course i've seen everything but the wind but it seems like my kids kind of fight that but the point that you made is now it makes sense to me it's like they want to create their own land they want to create their own path they want to do their own thing so i'm sitting here being a selfish thing like how the fuck you ain't going who who better to listen to than me but in their mind it's like you just want to do it our way my my my big thing is when i see other people i admire that are speaking similar songs because your boys will listen to me quicker even if we're saying the same shit with slightly different words.

11:24It's crazy. Yeah, it's just fucking the flight of man. It's just like it is what it is and then they really come around as they get older. You and I have the luxury of being middle-aged at this point. We appreciate things about our parents, our uncles, our grandparents that we couldn't comprehend when we were 13, 15 because we didn't fucking know the score. back to sports analogy these four teams right now right like they've watched the finals they've had success at other levels a lot of these kids right but like until you're in game six of the NBA finals places you've been where 13 seconds left like you don't know until you know right you like that that adage of like I really don't think someone really knows themselves until adversity hits.

12:17Someone once said to me on a business trip when I was a kid, it was real deep fucking, it's crazy. How old was I? This happened 25 years ago. It pierced my soul. I was 25. I had just started running my family business three years earlier and completely blew it up. Changed my family's life. Was building it for my family too, doing it right. I was one of those rare breeds where I was putting my dad on more than he was putting me on. I was feeling myself. I was feeling like the man because I was really built. Like I'm talking about of the family because I'm building the business that we're eating on and I'm working the hundred hours a week.

12:57But I wasn't flexing or anything. I was just listening to a different story. But this is, I'm giving you my mindset when this was said, it struck me to the core. This man who was like 48 at the time in business said some nonchalant, everyone's just talking over dinner, over wine, he said, a man does not become a man until his dad dies. And I never forgot it. And I'm very fortunate, I'm very grateful that I'm not in that position yet. Pops has, just spoke to him 15 minutes ago, complained about some dumb shit like he always likes to, about he's always, my dad is a fucking gangster. But it really struck me.

13:37and I think for a lot of people listening

13:43my biggest observation to the audience that listens to this podcast is the reason I pump all the content I put out out there is I think we're not grateful enough and I think we're soft and I mean it I think we complain about dumb shit for example I just was working on something on the flight down here from New York I'm on the board of something called Charity Water. We build wells for fresh water in Africa and parts of Asia. As we all are chilling right now, all of you behind the scenes and you and I right now, 800 million people on earth, 10%. There's 8 billion people on earth. 800 million people on earth do not have access to clean water.

14:28That means they can't get to clean water within six hours. And the way they get there, by the way, in most of those tribes is the woman puts a fucking bucket on her head that would make most athletes in the NBA struggle to carry on their head for an hour and she walks seven or eight hours with it, fills it with water and then brings it back. And we're out here complaining that our Instagram following isn't going up. Or like, why don't I have a Lambo? Or like, why can't I get into 11? like people crying about dumb ass shit. So I think that for the men and for the ladies, but for the men here, like stop acting tough until A, you got punched in the mouth and figured out who the fuck you were.

15:22And B, when all the responsibility of your family is on your chest. You know, and I think we need to get our perspectives right. That's what drives me. that's why I am not silent and just building my businesses that's why daily I am putting out videos and putting out stuff because I want to contribute in a positive way to the conversation and I think most of the shit that's out there is nonsense right I want to rewind because you talked about you know your business and building your dance business and you know where we started to where it was but you visualize YouTube as as an outlet to build a business and you were ahead of the game with that.

16:03Talk about that. And also piggybacking on what you said because you might just say a man doesn't become a man until you lose your father, which is crazy because I thought I was a man until I actually lost my father. But when I lost my father, it was at that point I realized in my life I knew everything to do. I wasn't confused. I wasn't lost. I wasn't, you know, concerned. Like I literally knew exactly where my job was. I knew what I had to do. I understood my responsibilities. I was no lack with my father. How old are you? I'm 44 now. My father passed away. I was 40. Really good. Sorry, it's still fast.

16:41I lost my stepmother. I lost my father. So you were also now the cancer. For me, the crazy thing is, everything was different until I lost my father. When I lost my father, I think everything caught up with me at once. So now I had to reach out, and I had to do my therapy thing. Good for you. I really get that balance and find myself. Proud of you. I was part of being a man. 100%. Growing up. And then all of a sudden, like I said, I'm looking around and I was not confused about what I need to do best. So he prepared me for that. And I was the man that he prepared me. So you absolutely swat off from that.

17:10But just talk about how you visualize to being an outlet to build and grow. In 2003, taking a step back, my dad had a local liquor store. He lived his American dream, had nothing, saved every dollar. I already told you my family didn't buy anything so we could save, save, save. and then eventually my dad bought a small liquor store in Springfield, New Jersey. Immigrant life. You know, I was 14. I started working there, stocking shelves. The shit you see at the gas station, it's like immigrant shit. Built a nice business for himself. Got to live, support our family with that. I came in and I knew, you know, I knew like I like talking to athletes because I love sports so much but I wasn't gifted physically that way.

17:55but mentally I was gifted that way and I knew and when I say I knew I knew at 14, 15 and this is before you're in the same general age group as me you know this business men weren't cool like that that wasn't a cultural thing rappers, athletes but being a businessman that'd be like fine but it wasn't like cool like it is now but I knew that I was going to be world class at business at that age I knew it and I grew up real immigrant what I mean by that is immigrant kids really understand this more than hood kids. Immigrant kids understand you do it for your family. It's not even about you. So I grew up where I was like my mom's the best of all time.

18:39She's just done so right by me. My father's worked his face off. I haven't even seen him like that. Bro, my father and I slept in the same house every night for the first 14 years of my life. I got 6 to 10 memories of him from 0 to 14. He woke up and left for work before I woke up. And he came home from work after I went to sleep. Seven days a week. Seven. So I had this crazy guilt and gratitude that I wanted to do right by them. So I decided, like decided. I remember calling my mom crying. Crying. When I was 18. I was a grown boy. Being like, Mom, I know that I'm destined for big shit. but first I'm gonna really build this business for dad.

19:30Like I was like I'm just gonna give up my 20s and build this business because I think I can and I wanna give back to my family. So that's what I did in 1996, 1997 I launched one of the first e-commerce wine businesses in America, winelibrary.com. The internet was crazy. That'd be like me telling you all let's build AI robots and have them sell shit on Mars right now. That's how crazy the internet was in 96.7 because it hadn't existed yet. And so like people were just like what is that even? I did that from 1998 to 2003. I ran the business. In those five years the business went from 3 million a year to 45 million a year.

20:13Completely changed my parents life. I bought my car at 16. I bought it at a garage sale with my money for$580. That is the first car I had. My brother's 11 years younger than me. He got a brand new Lexus on his 17th birthday. That's how much our life changed in that decade. In 2003, I'm cooking and I'm like really building. And I go to my computer guy, as I called him. He was a developer. I go, yo, I want to make videos and put them on the internet. How do I do that? he's like we have to host them this and that so he did the work he came into my office like a day later he's like here's how much it would cost I don't want to make this up because I want to keep it real but I'll give you what it felt like he said some shit like if an hour is watched on our website it's going to cost us$10 ,000 to host those videos it was something I could not afford no matter what so that was it it just got put on the side I want to give him his flowers his name is Eric Kastner with a K.

21:16He was my lead developer. Two years later, I'm working on some shit. We sat closer than you and I are sitting. That's how small the office. Close. No bullshit. Closer than you and I are sitting right now. We sat. He taps me. He goes, check out this site. It was YouTube. I go on it. I'm like, what is this? He goes, you remember the video thing? I was like, yeah. He goes, on this site, we can upload it and we can host it on the website. It'll cost free. They're taking on the costs. I'm like, bet. The next day I call my brother. I'm like, this thing's going to be crazy. He's a freshman in college.

21:52I'm like, you need to start a video show about the Jets. So he started, this is a fun fact, Stefan. You might not even know this. My brother AJ was actually the first vlogger. He did like seven or eight episodes of Jets TV. He did some videos, but it's not what he, yeah, respect. But he didn't, he didn't want to be about that world. he was more into like the business side so he was done pretty quick and I kept looking at YouTube it was getting bigger but it was all pirated shit in its first year it was like South Park clips Family Guy clips nobody was making original videos then there was this guy named Zay Frank Z-E space Frank he was making videos there was another show called Rocket Boom I was like there's something this is gonna be something so I on February 21st 2006 less than nine months after less than nine months after YouTube came out, I made my first video of Wine Library TV.

22:46Changed the course of my career. I knew, I wrote a book a couple years later called Crush It, my first book. If you were to read it today, it's crazy. I wrote that book in 2008. It came out in 2009. That book's 16 years old. Basically, I completely predicted content creators, influencers making money on the internet. And at the time it came out, it did extremely well, but critics panned it for being not realistic. One news outlet said, this guy's such a snake oil salesman. He's trying to tell you that people are going to make$100 ,000 a year on YouTube. LOL, LOL. It's crazy. It's crazy. And so, yeah, YouTube, I always knew that video was going to win.

23:39video always wins and I knew it would just be a matter of time before it was real on the internet back in the early 2000s and YouTube came. So as you go from wine media to intercapital, different things like that like what's the bridge? What was the bridge? The bridge was that actual moment. Nine months later or within that year YouTube sells for$2 billion. $2 billion in 2007. So nine months after you posted your first video? Yeah, about a year later, I don't want to get the timing wrong. Somewhere quick, I think it was the next year, YouTube sells to Google for$2.1 billion. Again, I want the kids that are listening right now to understand.

24:18$2.1 billion in 07, I would argue would be like a$100 billion, maybe even$500 billion deal today. Numbers were different. We didn't print all that money during COVID. The world was different. Everyone's shook. I read an article in the Wall Street Journal and in there, it's the first time I'd ever seen the term it was writing the article of YouTube this incredible exit and then it said angel investor Ron Conway is set to make XYZ amount of money on his $100 ,000 or I don't remember the number,$50 ,000 angel investment I was like, what the fuck's an angel investment? So I went to Google I typed in angel investment, I read it and I remember because it was one of those moments that you'll always remember in your life I remember I had the big ass computer screen and I'm reading it and you know how you can like see a reflection in your screen with the right lighting?

25:07I remember reading it and then I looked in the screen and looked at myself and I said motherfucker you're gonna be an angel investor. And I promised myself because at that point when YouTube sold like that I was like fuck man I got some sort of gift and I'm not making paper on it. I was right about email. I was right about the web. I was right about Google AdWords and now I'm right about YouTube. I'm good at seeing shit. I said I'm going to promise myself the next time I feel that shit I'm going to angel invest because I had a little bit of savings about six months later I had that feeling I saw a new startup and I was like this is it and I wrote my first angel check and that was Twitter so just for the people that don't angel invest is when you're investing early you're the angels you're basically the first money's in before there's institutional venture capital money you're the$50 ,000 and$100 ,000 smaller checks just to get someone off the ground later they'll go for a series A a venture capital round it's high I mean listen Facebook, Twitter I really really won there was others Uber I really lost and really won Snapchat there was a lot of wins but 98 % were losses.

26:29Like, don't get excited about angel investing if you don't have paper like that. Like, 98 % are losses. I don't think you understand that. That's why do you think I'm fucking taking this moment to fucking break it down? You know what I mean? Like, now, the reason it works is when you hit, you hit. You know, when you're making 3 ,000 times your investment back, you can lose a lot. So, but it is, I wouldn't call it gambling. I would call it extremely high risk investing. My last point on this and we'll bounce, I'd still do angel investing, but now I only invest if I like both the jockey and the horse.

27:09I used to do it if I liked the horse. The horse I call the idea. If I liked the idea back in 06, 7, 8, 9, 10, 11, 12, probably into 13, I would invest. The mistake I was making was I didn't realize, I would look at something and be like, oh shit, I know what to do with this. I'll build it big. But when you're putting money and you're not in control, now I gotta like the jockey too. I need to like her or him. I'm like, does she have the stomach for it? Now I'm analyzing the person. Because I got caught on all those Harvard kids. All those Ivy League kids came with good ideas, but they got fed. They got to Harvard because grandpa made a donation.

27:49They got to Harvard because they're a great fucking student, but being a great student doesn't mean you're a great entrepreneur. so I had to learn those lessons in my 30s and 40s. Great point, great point. I asked about the Uber because I do my research so obviously I do my research when you came on. It's a conflicting story. You lost in one. It's not conflicting. I lost in one. In my first book I just mentioned, Crush It, it's your first book. You're acknowledging the most of the people in your life in the first page. The only people I acknowledge is my family and then one random ass dude, Travis Kalkinick who was the co-founder and CEO of Uber.

28:24Travis was in between companies when I wrote Crush It and I sent him an early copy and he really helped me with it because he was just chilling. He actually, Garrett Camp, the founder of a company called StumbleUpon is actually the gentleman that came up with the idea of Uber. It was originally called Uber Cab. I was actually in the room in Paris when he literally pitched the idea for the first time. Garrett was involved. They were looking for a CEO. It was a side project. This is real talk. Yep. Two entrepreneurs that already made it had an idea. They went out and found a third guy, Ryan Graves, a hustler kid to run it because it was a side project because they were doing other shit.

29:11It started off real strong in San Francisco. Travis came in and decided to be the CEO because he saw it was going to be big. He asked me to invest. You know why I love this sale so much? Why? Because it confirms one of my favorite sayings in life. Scared money don't make money. Ooh, shit. They say that everywhere. They say that at the business offices with the CEOs and in the hood at the dice game. Bro. They say that everywhere. Bro, this moment is my watershed statue of liberty in a career that spans 30, 40 years, if you count my kid hustle. The amount of times I played Scare Money was almost zero because I came from nothing, so I was never scared to go back.

30:03But I bought my first big boy apartment in New York, and I had no fucking liquid. it. I just bought it. I was going to have my second child and I had no paper. I had a little bit, you know, that immigrant little bit, you know, like got to have a hundred thousand in cash somewhere. But you know, like I was not, I was not with paper. So when, when Travis came and said, I want you to invest in Uber, I was like, fuck. I was like, I'm going to have to pass to his credit, which is why I love him so much. He came back because we were boys. he came back three four five weeks later he's like bro i was in san francisco for a talk i was in that grassy knoll every time i pass it by i'm like fuck that spot he's like please be in i was like i just can't i said no twice if i had written the normal 50 000 check that i was writing back then 25 50 you're talking about three four five 600 million now so I pass about a year and a half later or a year later they were in their next series A like instead of, I would have gotten in at like a 4 or 8, I don't remember the number under$10 million valuation about a year and a half later I did invest, it might have been at $100 million or$80 million or$120 million and I did well I mean I made millions and millions of dollars when it went IPO on$100 ,000 investment it but you know yeah i mean like i'm grateful that i have a career that i can sit and talk about moments where i've passed on a twice that would have resulted in you know a half a billion dollars in paper and and to me like on the other side looking at all your reactions i've been telling the story for a decade i know how people react i react too but you know it's like you know this as an athlete when you're in the arena you're it's just next play yes it's just like you know you can hear the crowd booing you know you can hear the announcer's takes you can see the hot takes on you know on the shows and the radio but like what am i gonna do cry i'm still working like and in a weird way and i think people that get it will really get it on the other side of this podcast I'm happy it didn't happen not because I would have been any less hungry it would have changed the complete foundation of my life and I think in the butterfly effect I'm like like not to make me feel better but because of how I lived I'm like okay that would have happened but then this would have happened this like I'm in a world where I sit here today healthy and happy I'm like who knows I might have had to go to Tokyo for a business meeting because of that and maybe I wasn't paying attention crossing the street and got hit by a car.