Why Execution is the Game of Entrepreneurship with Jesse Itzler

In this episode of the GaryVee Audio Experience, I throw it back to a conversation with Jesse Itzler - the rapper behind the Knicks theme song - to discuss the importance of execution as an entrepreneur, the dedication it takes to be successful, and Jesse's origin story. Share this episode with a Knicks fan 💙🧡🏀

• 0:00Speaker 00

  This is the Gary Vee Audio Experience. Hey everybody, it's Gary again, back with another episode of my new show that I'm super excited about called Interrupted by Gary Vee. Today's guest is Jesse Itzler, an entrepreneur, but I'm gonna let him frame it up for you and then I'm gonna fire away with a bunch of questions, but first and foremost, Jess, thanks for being on.

• 0:24Speaker 01

  Oh, thanks for having me, I appreciate it.

• 0:26Speaker 00

  So, tell the mainzer nation that's listening right now, who you are.

• 0:30Speaker 01

  Great, well, I'm a serial entrepreneur. I started out in the music business. I had, I was signed to a record label called Delicious Vinyl in the 90s.

• 0:39Speaker 00

  What year did you sign?

• 0:40Speaker 01

  I signed in 1990, I was 21.

• 0:42Speaker 00

  And what kind of artist were you?

• 0:44Speaker 01

  Don't laugh, I was a rapper.

• 0:46Speaker 00

  I'm not laughing, I'm not laughing.

• 0:48Speaker 01

  And I was a white rapper, believe it or not.

• 0:50Speaker 00

  I'm aware, I can see it. For everybody who's listening, you'll hear some laughs in the background and things of that nature. We're here at an offsite kind of conference thing, so we're just recording the podcast in between sessions, so keep going Jess, so you're a rapper at 21.

• 1:03Speaker 01

  Started out right at...

• 1:04Speaker 00

  Where'd you grow up?

• 1:05Speaker 01

  I grew up in Long Island, and then I went to school in Washington DC at American University. Got a record deal, um, good test taker maybe, I don't know about smart, but...

• 1:16Speaker 00

  Fair enough.

• 1:16Speaker 01

  Got a record deal right out of college, after a lot of rejection. Signed to Delicious Vinyl, got dropped from the label a year later.

• 1:24Speaker 00

  Why?

• 1:25Speaker 01

  Sales and just wasn't the right thing, and tough timing, I was behind Vanilla Ice and I wasn't, you know, nearly as good as Eminem, here I am. But it was the best thing that ever happened to me, the worst thing at the time, cuz I only had two things on my resume after that, I was a kiddie pool attendant and I was a rapper, and that's not gonna get you a lot of jobs.

• 1:44Speaker 00

  How did the rapper thing go down? How old are you?

• 1:47Speaker 01

  I'm gonna be 52.

• 1:50Speaker 00

  Hey, you look great, so 52, so you're eight years older than me, so when does rap hit your radar?

• 1:55Speaker 01

  Rap hits my radar in, right away man, right when it came on the scene, I was probably, my, I don't know, 16, 15, so, early 80s, I heard "It's Like That" by Run DMC, "Sucker MC's" by Run DMC, "Fell in Love with You." With it grew up in Long Island where hip hop was like emerging fast.

• 2:13Speaker 00

  Yes.

• 2:14Speaker 01

  And just got the bug. So started out breakdancing, started out in the, you know, just doing whatever I could do. This is a different era, you know.

• 2:20Speaker 00

  I remember it.

• 2:22Speaker 01

  And um, just got into it. And when everybody in college was like making resumes and sending resumes to companies, I'm like, I'm getting a record deal. I don't need a resume. And uh, at that time, I'd never been in a studio.

• 2:33Speaker 00

  Were you an entrepreneurial kid?

• 2:36Speaker 01

  I was an insane kid. Like I tried everything. My parents gave me a long leash and um, I just tried anything and they allowed me and supported me to do anything like that. But I wouldn't say I was a sharp entrepreneur. I wasn't, I never paper route.

• 2:50Speaker 00

  Right.

• 2:50Speaker 01

  I was, no, but I was just, I was.

• 2:52Speaker 00

  You were not looking to make money?

• 2:54Speaker 01

  I was looking for adventure, man. I was looking for fun and I still am.

• 2:58Speaker 00

  Mm hmm.

• 2:58Speaker 01

  But I was never really wired for, to make money.

• 3:01Speaker 00

  So what did your crew look like? Were you like a skateboard kid too?

• 3:04Speaker 01

  I was, I was athletic.

• 3:05Speaker 00

  Okay.

• 3:06Speaker 01

  Um, I was artistic. I was a good storyteller.

• 3:08Speaker 00

  Mm hmm.

• 3:09Speaker 01

  And um, I wasn't scared. I wasn't scared to fail. I wasn't scared to try. Uh, cause my parents really just supported my effort. They praised my effort and not the results. And.

• 3:20Speaker 00

  Did they acknowledge when you failed?

• 3:24Speaker 01

  They praised the effort. So we got blown out of a basketball game or if I had a great game or a bad game, it was like you tried so hard. And they've always praised the effort. And as a father of four, that's something that we do with our kids. It's all about the effort.

• 3:36Speaker 00

  Where do you think, where do you think the Mendoza line is on praising effort and making one appreciate process? Versus creating delusion when one is not good at that thing?

• 3:48Speaker 01

  Well, I think the, the fine line in between those two points is disappointment. And I think disappointment's been stripped from kids.

• 3:55Speaker 00

  I agree.

• 3:56Speaker 01

  There's participation trophies and you get, you know, everyone's on it. You know, you can make.

• 3:59Speaker 00

  So your parents on the way home of losing a game forty two to sixteen were like, hey, I really appreciate the fact that you were down by thirty, that you were going hard. But in the same token, they weren't making excuses or saying you're gonna be Michael fucking Jordan.

• 4:11Speaker 01

  Yeah, but my, my dad owned the plumbing supply house, man. My dad didn't even get that deep into it. He was like, he took me to the game. He washed it and then he went and he sold plumbing supplies.

• 4:21Speaker 00

  Did he talk?

• 4:22Speaker 01

  He, of course he talked, but he wasn't, it wasn't about like raising this kid that's gonna go to Harvard or that's gonna be an amazing athlete. It was like.

• 4:29Speaker 00

  So you went, you went hard and you get in the car and he says, good, good job, kid?

• 4:35Speaker 01

  He says, "How'd you feel about it?"

• 4:37Speaker 00

  Okay, that's a really good.

• 4:38Speaker 01

  Yeah, and then I said, "I feel terrible. We got blown out."

• 4:42Speaker 00

  Right.

• 4:42Speaker 01

  And then he'd say like, "Well, you know, you did great and keep trying," and that kind of stuff. My father wasn't the kind of person to put any kind of pressure on me to succeed. He was a family guy, he still is, and it was just about that.

• 4:56Speaker 00

  And mom?

• 4:57Speaker 01

  Teacher and then raised four kids.

• 5:00Speaker 00

  And what was she saying to you?

• 5:02Speaker 01

  Um, same thing. It was just-

• 5:05Speaker 00

  She's like, "You look so cute in your shorts." Like, was she like that kind of mom? My mom was. She was like, "You looked great too." I was like, "Thanks, mom." I think I was like 16 when I first realized, "Wait a minute, I'm not the best-looking person on earth." Like, was she like that kind of mom?

• 5:20Speaker 01

  She was, they really gave me my distance and they let me figure it out myself. I was the bottom four.

• 5:27Speaker 00

  Got it. It's cool, though.

• 5:29Speaker 01

  It's very cool.

• 5:29Speaker 00

  It is cool. Like, they've been through enough reps where I'm sure you're, is there a sister or brother that's the oldest?

• 5:36Speaker 01

  Brother.

• 5:36Speaker 00

  Had it slightly different.

• 5:38Speaker 01

  Yeah. Yeah. It was the best kind of childhood for me, though, man. There was no, I didn't feel any pressure to have to, it was, you know what they did? They put the pressure on me.

• 5:46Speaker 00

  By not putting the pressure on you.

• 5:47Speaker 01

  They made me want it for me. Like, it can't be my parents' dream. It had to be my dream.

• 5:52Speaker 00

  I get it.

• 5:52Speaker 01

  And they never, I remember when I wanted to get good grades from my parents, my grades sucked. When I was like, "I want to get good grades so I could like get to a good school for me," they skyrocketed. So they took the pressure off of me.

• 6:05Speaker 00

  The freedom created the result.

• 6:07Speaker 01

  It was my goal. It was my dream.

• 6:09Speaker 00

  So now you get signed. Tell them about the New York Knicks song.

• 6:13Speaker 01

  I get signed to this label called Delicious Vinyl. I wrote a couple of songs for an artist named Tone Loc. I get dropped from the label a year later. I move back to New York City. I have two things on my resume. I was a kiddie pool attendant and I was a rapper. And, but-

• 6:28Speaker 01

  My wife always says this, it's so true. You find your passion at the intersection of what it is you love to do and what you're good at and providing a product that people like or enjoy. I love sports and music, so I married those two things. And I wrote a theme song for the New York Knicks. It was called "Go New York Go." I was 22 and the Knicks paid me $4,000 for the song. It cost me $4,800 to do the song. She asked me if I was into money. Not really. I lost $800 on my first big trade. But the reality is I would have paid the Knicks 10 grand to do the song. And the song became the number one most requested song on New York radio and that took off.

• 7:06Speaker 00

  As a 44-year-old Knicks fan, you can't imagine what that song actually is. It was being played while the Knicks made a run and actually got to the NBA Finals, lost unfortunately in seven games to the Rockets. But like, I probably heard that song 8,000 times. 7,800 of them were in a four-week period in 1994.

• 7:28Speaker 01

  Yes.

• 7:30Speaker 00

  It was insane.

• 7:31Speaker 01

  It was insane.

• 7:32Speaker 00

  Like, that became your... Tell me, living that moment where, like, June 1994, you're eight years older than me, so you're 22, right? 22, 23. Are you basically... You know, the internet's not around, so people don't know shit the same way. Are you just walking around life and before you even say hi, you telling people that you wrote that fucking song? I would be.

• 7:54Speaker 01

  Yeah, well, it was interesting because at that point in my life, I slept on 18 different couches. So I had 18 different friends. I bounced around for a week here, to couch, couch, couch, couch, and then all of a sudden I wrote this song and it's the number one song, you know, at the time.

• 8:10Speaker 00

  It was crazy. Big, big. In New York, uncomfortably big.

• 8:15Speaker 01

  Yeah. And I didn't really know how to handle that, you know? But everyone was asking me for playoff tickets. And I had no money. I was sleeping on couches. And you know what I did? I got everybody playoff tickets.

• 8:28Speaker 00

  That's cool.

• 8:29Speaker 01

  Yeah, on my credit card. And I realized at an early age that to be a connector, and not having to ask for anything in return, and just, I knew it would come back tenfold. And I wanted to be the guy that could get anything done, you know?

• 8:41Speaker 00

  That was what you wanted to stand for?

• 8:43Speaker 01

  I still do. Anything, like, there's no obstacle, there's no business, there's no goal, there's no race.

• 8:48Speaker 00

  So how much in playoff tickets do you end up spending?

• 8:53Speaker 01

  Enough that it set me back. But, but, again, those seeds, those seeds, you know, were planted. Yeah, they paid off later.

• 9:01Speaker 00

  So what happened next?

• 9:02Speaker 01

  So, all of a sudden, I was like, whoa. As an entrepreneur, you guys, we have a lot of entrepreneurs in this, in this room, you realize that you look for something that differentiates yourself. And this was a big differentiator for me. I was like, no one else is doing sports music. Everyone's trying to be Vanilla Ice at the time, or whatever, but no one's writing theme songs for pro sports teams. So that was my aha moment. And I started, I set up a company to write theme songs for other teams.

• 9:29Speaker 00

  Interesting.

• 9:30Speaker 01

  And I'm like, I ended up doing almost every team, and then I sold that company.

• 9:34Speaker 00

  In the NBA?

• 9:35Speaker 01

  NBA, and some baseball and football.

• 9:38Speaker 00

  What was the most next famous song?

• 9:41Speaker 01

  Well, what happened was, the songs became somewhat popular in each region, but I turned it into selling them as a compilation with all the songs that.

• 9:48Speaker 00

  That I understand, but in its own region, I mean.

• 9:50Speaker 01

  Chicago, because Jordan came back. It was all called Right Back in it. But I sold almost a million units. So it became a business, and I sold that company to a public company.

• 10:00Speaker 00

  And in that transaction, did you make some money?

• 10:02Speaker 01

  Yes.

• 10:03Speaker 00

  Did you have to work there for a little bit?

• 10:06Speaker 01

  I worked, we had an earn-out. So I worked there for a year and a half, and then we hit the earn-out.

• 10:10Speaker 00

  Talk to me about that year and a half.

• 10:12Speaker 01

  Uh, well, in our contract, they paid us a couple of million dollars upfront, but we had a sixteen million dollar trigger if we hit X amount in profit. So we literally had a calendar. We had three years to do it. And I'm like, every day it was like, we got three hundred and sixty-four more days, man. We gotta hit this number. Every day was a countdown. And uh, that's how, I mean, and we hit it.

• 10:33Speaker 00

  So you're wildly motivated, interest-aligned?

• 10:36Speaker 01

  Yeah.

• 10:37Speaker 00

  Day, you hit it, you're out. What happens next? Now you have some money.

• 10:41Speaker 01

  What happens next?

• 10:42Speaker 00

  How old are you?

• 10:42Speaker 01

  I'm twenty, at the time, maybe twenty-six.

• 10:45Speaker 00

  And you have some money?

• 10:46Speaker 01

  Mm-hmm.

• 10:46Speaker 00

  Like, way more than you ever had before?

• 10:48Speaker 01

  Yeah, anyone in my family.

• 10:50Speaker 00

  And? Do you go crazy? Do you do some shit? What do you do?

• 10:53Speaker 01

  No, I mean, my li- my life was, is pretty simple. It's pretty simple then, it's pretty simple now. But um, I was still twenty-six, twenty-seven years old. But what happened was, the guy that bought our company had a time share on a private jet. And he invited me at twenty-seven years old onto his private plane. It was like, when I walked on, it was like, I don't know if you guys saw The Wizard of Oz. It was like the scene in The Wizard of Oz, when everything goes from black and white to color. It's like, what? People fly like this? I was like, you gotta be kidding me. I wanna fly like this. So by the time we landed, my partner and I were like, let's start a private jet company. So we can fly on private planes when we travel. It's like, definitely, except we had no airplanes. But um, but we had an idea, and we took that idea to-

• 11:32Speaker 00

  And who was that partner?

• 11:33Speaker 01

  Uh, his name is Kenny Dichter. And we took that idea to-

• 11:36Speaker 00

  And how did you meet Kenny?

• 11:38Speaker 01

  Kenny was, so I owned the trademark to all these themes. The songs that I was writing for the sports teams were popular, but the trademarks were more valuable. So Go New York Go is being used by Budweiser, Foot Locker, all these big companies. And I wasn't getting any money, because I sold the song for four grand. So I got smarter, and I started licensing the song and keeping the marks. Kenny owned a clothing company. So I'm like, we make Go New York Go t-shirts and hats. And we started working together, and, you know, built a big business out of it. Then I was a guest. I'm like, let's start a private jet company. My, he was like, definitely. And um, we took a meeting with a company called NetJets, owned by Warren Buffett, the largest private jet company in the world.

• 12:18Speaker 00

  How'd you get to that meeting?

• 12:20Speaker 01

  This is a crazy story, man. The president of NetJets' daughter had a sweet 16, and Christina Aguilera was performing. And through somebody that knew me, they knew that I knew the manager, and called up and like, "This guy wants to do me a special for his daughter." And like I said, nothing is impossible. I called up, and the next day at the concert, she was a background singer with the mic off. And he called me up, he was like, "I don't know who the fuck you are, or what you do, but my daughter is a hero in our town. If you ever need anything, let me know." A year later, "I need 650 airplanes." Jim?

• 12:56Speaker 01

  You remember Christina Aguilera's story? I'm like, "That was me. Can I see you on Friday?" Friday comes, we go and we have the meeting. And it lasted about 12 minutes. And the CEO, Rich Santulli, said, literally threw us out. This is a direct quote, and it really pissed me off. He said, "If you think I'm giving two guys, who probably didn't break a thousand on their SAT, which really pissed me off. I got a 980 on my SAT, so that really bothered me." He's like, "That's never happening." He threw us out. And then the president, Jim, who had got his daughter hooked up, grabbed me and said, "That was unbelievable." So we got thrown out in 12 minutes. He goes, "Santulli doesn't give anyone 12 minutes. I believe in this, but bring it to life. Come back next week." So we came back next week, and we realized, like, we could never sell this idea in a PowerPoint, because this guy sees 100 PowerPoints,

• 13:40Speaker 01

  and entrepreneurs have to differentiate. So we brought in our own focus group. And we set up a table by the boardroom table, and one by one, we had eight people come. Carl Banks from the New York Giants, Run for Run DMC, a powerful female, a real estate mogul in New York. And one by one, they stood up, and they said they'd never buy a fraction what NetJets was selling, but they'd buy a 25-hour jet card, what we were offering. And he gave us a deal. And a year later, we did $5 billion in sales.

• 14:08Speaker 00

  Then what happens?

• 14:12Speaker 01

  Then life changed. The chips are purple. And, you know, money's interesting, man. It's interesting. We all play for it. We all want it, but we don't really even know what we're playing for or why we want it. And then we get it, and it's confusing. And my relationship, we think of relationships in terms of people. How's your relationship with your mom or your dad? We don't think of relationships in terms of money and time. And I have a very good understanding of my relationship with time. I know you just posted that. I've been talking to that for a while, and money. And all of a sudden, I came into a lot of money. And I was single. And I had airplanes, and I was in New York. I could go on a date with this lady. I'd be like, if it was going good, I'd be like, you want to go to Canada?

• 14:56Speaker 01

  What do you want to do? I mean, like, people are going to Studio 54, trying to get into Studio 54. I'm like, let's go to Hawaii tonight.

• 15:04Speaker 01

  So I had a great decade.

• 15:09Speaker 00

  Fair enough. And then what happened?

• 15:14Speaker 01

  And then I decided that I didn't want to sell airplanes anymore. Like, that wasn't, um, I didn't feel like... I felt like I wanted to make a quarter by myself and a 75 cents in the company I was in. I want to go out on my own. So I was training for a 100-mile run. I realized, I signed up for the USA National Ultra Marathon Championship because you didn't have to qualify. You could just send $50 registration, and you're in the national championship. And I'm like, I'm competing in the national championship? It's fucking unbelievable. Then I Googled, "How do you run a 100-mile race?" And it came back with a year, everything came back with a year.

• 15:53Speaker 00

  How did that even hit your radar to enter?

• 15:55Speaker 01

  I went through a crazy period of time, man. I was thinking about giving all my money away. I was thinking about charity. I was just like, I just, you know...

• 16:03Speaker 00

  You were just trying to figure it out.

• 16:04Speaker 01

  Trying to figure it out. And I was like, I want to do something big for charity. And like, I didn't want to have a bake sale or a golf outing. My friends were outing like foursomes.

• 16:12Speaker 00

  Yep.

• 16:12Speaker 01

  I'm not a foursome guy.

• 16:14Speaker 00

  It's a golf term. Relax.

• 16:16Speaker 01

  Yeah.

• 16:17Speaker 00

  Keep going. Just trying to help the kids at home. Go ahead.

• 16:21Speaker 01

  I want to run 100 miles without stopping.

• 16:24Speaker 00

  Yep.

• 16:24Speaker 01

  So I like, and what would be the biggest race to do that in? For me, it was the national championship. So I Googled it. It gave me, everything was like a year training program. The race was in 90 days. So I went from basically couch to 100 miles in 90 days. And during the training, I did a lot of research around hydration and nutrition. And everything pointed to coconut water. So I became the human guinea pig for coconut water. And like, um.

• 16:47Speaker 00

  What year was this?

• 16:49Speaker 01

  This was in 2008, six, 2006. Because when you run 100 miles, like, how many calories that's taking an hour? How much sodium? How many fluid ounces do I need? Coconut water was the solution. So anyway, I finished the race. When I got to mile 83, I had seven toenails floating around in my shoe. But I don't negotiate my goals. Like, we don't negotiate our goals in this room. Like, whatever our goal is, it's unwavering. And like, the plot might change and the script might change, but the goal doesn't change. It's not like, my goal wasn't 87 miles or 83 miles. So I finished it, and then I was like, this coconut water shit, man, there's something to this. Like, by the way, I was in a wheelchair for four days after the race, but I did finish it. And I spent a year trying to figure out how to.

• 17:31Speaker 00

  Do you have photos of you in that wheelchair?

• 17:32Speaker 01

  Yeah, yeah, yeah.

• 17:32Speaker 00

  You ever post it?

• 17:33Speaker 01

  Yeah.

• 17:34Speaker 00

  That's a good one.

• 17:34Speaker 01

  Yeah, yeah. I have a whole, did a documentary on it.

• 17:36Speaker 00

  Go ahead.

• 17:37Speaker 01

  You know.

• 17:37Speaker 00

  Yep.

• 17:38Speaker 01

  Anyway, long story short, I spent a year trying to figure out how to import coconut water, and I did get a 980 on my SAT, because I couldn't figure that shit out, man, it was way over my head, but I knew I could market it.

• 17:47Speaker 00

  Bro, I can't even spell coconut water.

• 17:49Speaker 01

  Right.

• 17:49Speaker 00

  Okay, so you can go. I get it, keep going.

• 17:51Speaker 01

  You would have been a great partner for me.

• 17:52Speaker 00

  Clearly.

• 17:53Speaker 01

  Um, but I knew I could market and sell it. So I partnered with a company called Zico, Z-I-C-O. They were doing about $3 million in sales at the time. You know, one of the things as an entrepreneur is figuring out how to get from point A to B the fastest, you know? And for me, the learning curve was too great, so partnering was the fastest way. So I partnered with Zico, and two years later, we sold it to Coke. And, um.

• 18:19Speaker 01

  I got married. I married an entrepreneur. My wife owns a company called Spanx, which is a big deal here in the States.

• 18:26Speaker 00

  Sure is.

• 18:27Speaker 01

  Internationally, too. And that's where I am.

• 18:31Speaker 00

  And then what?

• 18:34Speaker 01

  I started shifting my life to...

• 18:36Speaker 00

  Think about changing my show to "And Then What?" with the movie. Go ahead.

• 18:40Speaker 01

  I started focusing, putting more on my plate of the things I love to do with the people I love to do them with. So my life shifted. It didn't really shift because it's always been this way, actually.

• 18:51Speaker 00

  You just put the energy into a different bucket.

• 18:54Speaker 01

  The energy was actually always there, but I started really obsessing on experiences and just really obsessing on, almost like living a manic life.

• 19:05Speaker 00

  Is that how you ended up in Atlanta? The Coke transaction?

• 19:08Speaker 01

  No, my wife's business is in Atlanta.

• 19:09Speaker 00

  Understood.

• 19:10Speaker 01

  But I shifted after these sales to like really becoming more experiential and being intentional about how I live my life.

• 19:16Speaker 00

  Was the coconut water sale?

• 19:18Speaker 01

  2013-ish. Yeah. And the coconut water deal was interesting because we were the first company ever, I believe, or at least publicly, to actually go to, again, how do you get from A to B the fastest? To go to influencers and celebrities like Gisele and Kelly Ripa, Eminem, and take money in as investors in exchange for equity for doing more stuff. Like 50 Cent's got equity.

• 19:45Speaker 00

  Yep, and vitamin.

• 19:46Speaker 01

  And vitamin water. These guys wrote checks. So it was really authentic. And customers are smart now, man. They can see through endorsements. So we had these like real people that really believed in it, real brand ambassadors, and it worked. And we sold it pretty fast. And now I got four kids. We're part owners of the Atlanta Hawks, which you know. We live in Atlanta.

• 20:05Speaker 00

  Which is the epicenter of culture in America. Maybe the world, even for that matter. It's a really dynamic time in Atlanta for me. Like, just like, it's been really fun to watch it for the last decade. It's just very clear to me an importance of business because I think business is a byproduct of what is established in culture. Popular culture in America starts in Atlanta. I really believe that.

• 20:31Speaker 01

  It's an amazing city.

• 20:33Speaker 00

  When I think about what hip hop actually means to the world and where the innovation and it's just it's and then you start layering in the tax breaks that are now in place for Hollywood and just the Hollywood infrastructure that's being built. It's just a really interesting time in Atlanta.

• 20:51Speaker 01

  Yeah, I feel fortunate to be a part of it and I feel fortunate to have been raised in New York because I think New York gave me a lot of edge, a lot of competitiveness and helped me just get over my fear, man. You couldn't you get swallowed in New York if you were walking around scared.

• 21:07Speaker 00

  That's right. What do you think, what's, what's, you know, hearing that background and a lot of people, you know, hear that it's obviously, you know, I think this is what, you know, we don't even really know each other that that well and I think our relationship is like so good because I think it's bound on this intuitive, creative entrepreneurial execution. I think we have more similarities than we don't, but obviously we have differences. What it's what leads me to this question. What's just a hot take. What are four to seven observations that you think are interesting right now in the world through the lens of entrepreneurship? Like individual person, platform, what somebody's doing.

• 21:52Speaker 00

  What's like on your radar as a consumer of energy around shit like this?

• 21:57Speaker 01

  I think that a lot of entrepreneurs have been tricked into thinking that things happen quickly. And, you know, for me, my journey was different and I remember going to Coke when we had Zico and the president of Coke said it takes eight years to build a brand in this country. And I was like, eight years, like, you know, I live in dog years, everything's time. So I'm like, I live with eight years is forever. And I feel like every year for me is four years, literally, the way I live my life. So I feel like.

• 22:24Speaker 00

  That's in the speed of your execution.

• 22:26Speaker 01

  I just feel like I've done 200 years worth of stuff in 50 years. But I feel like entrepreneurs are feel like it's get rich quick and everything has to be quick. And we try to cut corners and not all, but that's just the vibe that I'm getting. And because we live in an age of likes and Insta and fast and speed and that's amazing. But there's also that leads to disappointment like it takes time and that's okay to build the foundations of a long lasting business.

• 22:53Speaker 00

  I think what what we've glossed over and you touched on it lightly with the tickets is a lot of your execution, you know, it's really cool to get the meeting with the jet company. What's more interesting to me is why those really fancy people would go to that meeting and sit there. You've built up equity through relationships which takes time to be able to convert that energy for that execution.

• 23:16Speaker 01

  Yeah, yes.

• 23:18Speaker 00

  I mean, why did, why did Carl Banks and Ron and all these people, why did they go?

• 23:24Speaker 01

  I'm gonna tell you why. I'm gonna tell you why. Because people buy into stories, people and momentum more than products.

• 23:31Speaker 00

  Always.

• 23:32Speaker 01

  So you're the business plan. You're the business plan. Like, we had momentum and we had a story and when you have a story that's exciting.

• 23:41Speaker 00

  But even taking it for, yes. But what I'm curious about is buying the tickets on your credit card. Hey, everybody, I hope you're enjoying the podcast right now. Make sure you follow the podcast. That's why I'm interrupting. Let's keep going on this show, but follow the podcast. It'll make my mom super happy. You're right. How does one who's listening right now get in front of the Carl Banks and the Ron of their day, Gunna, right now, get in front of Gunna and Von Miller right now, for everybody who's listening, is a disconnect? I want to go into that because I would argue the seed of so much of this foundation is within that.

• 24:18Speaker 01

  You put yourself in a position where luck can find you. You put yourself in a position where you attract luck. So like, when I was 21 years old, man, I had nothing. I wasn't, I wasn't like broke, but I had nothing. I was staying on couches. My office was the Beverly Hills Hotel. Because I realized that if I went to the Beverly Hills, I was 21 years old, I got invited to a lunch meeting. And I walked in, I'm like, Russell Simmons, there's Lior, there's all these music moguls and entertainment moguls, and I'm like.

• 24:46Speaker 00

  This is where everyone is.

• 24:47Speaker 01

  You don't have to have a room at the hotel to come to here for lunch. I was like, what? I can buy an $8 salad. And sit here for 10 hours, and I did, every day. And that was my office. And then people started recognizing me. And then it was on me to attract them. Hey, you look cool. Whatever, just to get a face. And now, all of a sudden, after six months, I put myself in a position where I could get a record deal, where I could find somebody, where I could call somebody, where I could say, hey, can I borrow you for five minutes?

• 25:20Speaker 00

  Let me interrupt, I apologize.

• 25:21Speaker 01

  It's the name of the show.

• 25:23Speaker 00

  Thank you very much.

• 25:26Speaker 00

  What scares the fuck out of me is how unbelievably true that is, how an $8 salad for that cost is the arbitrage, and how somebody in Iowa that's listening to this story right now in the rural part of Iowa has something 37 trillion times more powerful than your ability to be in a place to pay $8 for that salad, which is called direct messaging on Instagram. What scares me to no end is that people will spend 80 trillion hours on dwelling and complaining and worrying about what they don't have. But we live in fumble, bumblefuck Iowa, listen to these two right now and not realizing what they do have,

• 26:11Speaker 00

  which is us two schmuckos with all our charisma and all this, still didn't have something called Instagram DM. And the 21-year-old you would have stayed on that couch and DM'd for 19 fucking hours because you would have bled for it, and then there would have been one yes. And that is such a real story right now for anybody listening, not just people that happen to be in city areas where this shit could happen. The serendipity of creating that for you now is little... But people then hear me say that, because I put out that content, and they give up after 29 people that they DM, and then they DM me, and they're like, Gary, you're fucking full of shit. I DM'd a bunch of people. I haven't gotten my music out there or sold my t-shirt.

• 26:56Speaker 00

  I'm crazy. And I reply, I'm like, hey, Carl, with three followers. I'm like, how many people have you DM'd? They're like, 29. I'm like, go fuck yourself. You sat there for fucking 12, 15 hours a day.

• 27:09Speaker 01

  I think, can I add on to that?

• 27:11Speaker 00

  You can do anything you want.

• 27:12Speaker 01

  So, I think a lot of people do, send DMs, don't even actually know how to send the proper DM.

• 27:18Speaker 00

  I agree. By the way, real quick, because I'm gonna add on to it. There's been plenty of people that went to the right places that lost.

• 27:25Speaker 01

  Oh, yeah.

• 27:25Speaker 00

  You had the right tack to start the conversation with Russell Simmons. It's my life. I'm on the other end of this now. It is fascinating to me to watch people go with selfish behavior in their one serendipitous moment to get something to happen.

• 27:42Speaker 01

  When I write an email-

• 27:42Speaker 00

  People roll up, I mean, I apologize, 99.999% of the time to tell me what I can do for them.

• 27:50Speaker 01

  Yeah. It's, the whole thing about this, it's like, as entrepreneurs, there's one rule of thumb. We have to create value. If you obsess on-

• 27:58Speaker 00

  As humans.

• 27:59Speaker 01

  Right. If you obsess on value and wake up, how can I provide value as a husband, as a boss, or whatever, in the long term, it's gonna pay off. And-

• 28:08Speaker 00

  Always. You won't, you won't have the ability to pick up all the opportunities.

• 28:12Speaker 01

  Right. One thing that I do that really helps me, I ask myself a very simple question. What I recommend myself as, fill in the blank. What I recommend myself as a dad, as a CEO, as a business partner? If the answer is no, why? And what am I doing wrong? When it comes to DMs, I feel like people wanna know, like, what's in it for me? So, when I write an email, I could spend three hours on an email. Sleep on it, review it, edit it. How can I make it shorter? Is the caption punchier? If I was the recipient, how would I react to it? Like, it's not like just, oh, I'm gonna DM and boom. It's like, how do I get this person to respond in the way that I want the response to happen? And I don't believe in-

• 28:53Speaker 00

  Real quick-

• 28:54Speaker 01

  Yep.

• 28:54Speaker 00

  And what we're painting for everybody who's listening is, look, the fucking internet has given everybody an at-bat.

• 29:01Speaker 00

  It doesn't mean that you can hit a fastball. And so the work you put into having the ability to hit a fastball, but the fact that we're now in a place where everyone gets an at bat, which was not the case pre-internet, is bonkers, bonkers shit.

• 29:15Speaker 01

  You're a genius about this DM thing, though, because like, I got a lot of layers to get to me. I have my assistant, voicemail, people screen my email, but I check my own social. So, I actually, to your point, now that you bring it up, the guy that does all my merch for my company, 29 or 29, this race company we have, DM'd me. And you know what he said? He created a win-win. I mean, I'm sorry. He created a no-lose. Win-wins don't work. Because if I say a win-win with... You talk about this too?

• 29:44Speaker 00

  No, no, I like where you're going.

• 29:45Speaker 01

  When you have a win-win, Gary might win here, and I might win here. That's not a win-win. That's a Gary's dominating the win. A no-lose is, oh, there's no risk, I can't lose. He sent me a DM and it said, "Hey, send me your logo, I'll send you a bunch of samples of stuff, no cost, no risk, no anything. If you like it, I'd love a shot to work with you." I'm like, "Okay." I sent it to him. A day later, I get a FedEx with this amazing product line, and I'm like, "Done." Hundreds of thousands of dollars later.

• 30:14Speaker 00

  We talked about this earlier, and it's great for everybody to listen. It's about doing instead of talking. People DM me all day long, "Gary, I want to work for you for free."

• 30:25Speaker 00

  Okay, that's amazing. Like, if you think about it, that sounds win-win. No-lose is, "Gary, I made this." And then we look at it. Our team looks at things that are made with my content. We, 99.999% of the time, don't even hear you when you say you're going to work for free.

• 30:42Speaker 01

  Yeah.

• 30:43Speaker 00

  Action. Always action.

• 30:46Speaker 01

  I invited, um... I went to a dinner party with my wife, and they went around the room and they asked everyone to name three people that were alive they'd want to have dinner with. And you came up, "Oh, Gary, Buffett, this one, that one." But when it came to me, all three of mine were rappers. And the reason was, I wanted to meet the three people that changed the course of my life as a 14-year-old kid growing up in New York. So at the end of the dinner, I called my 10... I invited the 10 most influential artists in my life to my house for dinner, and they all came.

• 31:15Speaker 00

  That's cool.

• 31:15Speaker 01

  I knew two of them. And people were like, "How did you get Rakim, man? How did you get Big Daddy Kane?" And I'm like, "I asked them."

• 31:23Speaker 01

  In a no lose and they came. People want to help people.

• 31:27Speaker 00

  Yeah, it's really crazy because again, it's super important because I want to make sure the listener gets value. You've put up enough W's on the board and had enough social currency to pull off that hail Mary, which is amazing.

• 31:38Speaker 01

  You're right.

• 31:39Speaker 00

  On the flip side, it's also how you got there because the 21 year old you that had nothing was willing to ask 100 people to get one yes.

• 31:49Speaker 01

  Yes.

• 31:50Speaker 00

  Okay, that's why I'm fired up. So for everybody listening, if you've put enough wins on the board, you're probably more likely to get seven out of 10 yeses than you think. And for everybody who's the 20 year old you and me that nobody knows at all or gives any fucks, you will get a one out of 400. How do I know that? Because you and I are exactly the characters that say yes out of that 400 once every thousand times.

• 32:13Speaker 01

  I still do it.

• 32:13Speaker 00

  Me too, which is why I'm saying it again.

• 32:15Speaker 01

  Yeah.

• 32:17Speaker 00

  This is a very important conversation and because we grew up in the same era, I shit on these entrepreneurs in this era. You gave me the internet? Fuck you. Fuck you. This internet thing? Fuck you, man. First of all, I would have definitely not graduated high school. And second of all, I would have made some crazy shit happen. Like you've got it so easy right now.

• 32:46Speaker 01

  Yeah, I mean, I remember when I, just to that point, Gary, when I was starting out at Marquee Jet, I was looking for my first customer and I didn't have a database. I didn't have Salesforce. I had no way to get lead. The only way I could get a lead was to show up where rich people were. This was like in 99.

• 33:01Speaker 00

  Right.

• 33:01Speaker 01

  But I had to go where rich people were. I didn't, we didn't have.

• 33:03Speaker 00

  You had a pager?

• 33:04Speaker 01

  A what?

• 33:05Speaker 00

  Did you have a pager in 99?

• 33:06Speaker 01

  I had a pager. I probably have like, but there was no.

• 33:08Speaker 00

  But you had that pager to like, yeah, cool.

• 33:10Speaker 01

  I had to show up.

• 33:11Speaker 00

  100%.

• 33:12Speaker 01

  I couldn't like, I didn't like, I had no email list. And I heard about this event called TED, this conference called TED in Monterey. California, I'm like, there's gotta be rich people at TED. So I flew 16 hours. I connected in Chicago, landed in LA, drove five hours to Monterey. And I get to the event and I recognize immediately, like, you can't get into TED without a credential. And I'm like, that's so ridiculous. You need a credential? So I just traveled 16 hours. I need a sale. So I go to the coffee shop and I realize that every 15, every hour and a half, people are coming in and they're ordering lattes and muffins. Because they're on break. They have credentials. They're on break at the conference. So I'm like... So the next day, I showed up at the coffee shop and I-

• 33:53Speaker 00

  You stole a fucking credential?

• 33:54Speaker 01

  No, I bought every single muffin in the store. I controlled all the muffin inventory in Monterey, California.

• 34:01Speaker 00

  I believe in this shit.

• 34:02Speaker 01

  And the first break comes and the guy comes, I was like, "I'll have a latte and a muffin." The guy's like, "You can have a latte, but we're out of muffins." He comes back out. I'm like, "So sorry, sorry." "I overheard you." I actually have a muffin.

• 34:14Speaker 01

  "I have 450 muffins." "Would you want one?" He's like, "Well, he's like, "No, no, you can take one." And I says, "Well, what do you do?" We start talking. I said, "I own a jet company." He goes, "Get out of here." He's like, "I'm actually in the..." This really happened to me. "I'm actually in the market for a private jet." He goes, "Do you mind if we sit down and talk about it?" I'm like, "Mr. Qualified, you can sit wherever you want to sit, man. Absolutely." And he was my first sale. Josh Koppelman from Half.com.

• 34:37Speaker 00

  Oh, Josh.

• 34:38Speaker 01

  And that's how my first sale.

• 34:41Speaker 00

  But like, but if you think about, it's actually stunningly unbelievable and wildly not. It's incredibly practical. You know who your customer is. Go there. What pisses me off, and this is why he's telling this story and it's an interesting take, is that's amazing and epic and iconic of a story. You can lay in your fucking bed and email and DM people. Like, what is a matter with people? Like, back to, nothing is impossible.

• 35:11Speaker 00

  Well, the internet has made it uncomfortably easy. And yet, people are losing? Fuck you.

• 35:19Speaker 01

  I think it goes back down to what I said earlier, even deeper than the DMs, Gary.

• 35:23Speaker 00

  Go ahead.

• 35:23Speaker 01

  Is negotiating your goals. And I think you asked me about entrepreneurship and I said, you know, people want to happen quicker and speed up the process and this and that. But I also think it's easy to negotiate your goals. It's easy now to say like, "Oh, I'm not gonna do this, I'm gonna try this, I'm gonna throw..." And like, people don't stick with things. Most people do 95% of the same thing.

• 35:45Speaker 00

  Because they don't mean it, Jess. They actually don't. It sounds good. Like, there's a really deep psychology on this that people have to wrap their... And by the way, there's nothing wrong with it. Like, why do you want to be a billionaire? Why do you want to start a business? Like, this is what goes into like, a very deep conversation, which is, people do things they think they're supposed to do. They don't mean it. When you mean it, there is no other option. When you mean it, there is no other option. When you don't mean it because you think it projects well, or it's the thing you should do, or your parents want you to, or you think it's cool, or it'll get you girls, or it sounds fun.

• 36:23Speaker 01

  The deeper layer of that, the deeper layer of that, of meaning it, comes from wanting it. And I could say, if someone said to me, "What's the silver bullet of being an entrepreneur?" I would say, "You have to really want it." And then people laugh. "I really wanted the promotion, I really wanted to win the lottery." They don't understand what I'm talking about. I can look at someone in their eye and tell right away if they want it or not, if they're willing to go through the 18 couches that I went through. And I'm not... I have plenty of egg on my face, too. You gotta want it so bad that the obstacles don't mean anything. So if you do 400 DMs and they don't hit, it doesn't mean anything. You're on DM1. It starts with wanting it.

• 37:01Speaker 00

  And when you're really there, you're like, almost evil about it and you're happy nobody replied. Like, where I go is a scary place where I'm like, like, I hear that, I'm like, "Yeah." Like, I'm... Like, I want... I want disgusting. Like, I want... Like, I mean it. If I hit 400 DMs and it comes back goose egg, I get crazy. I'm like, "Uh-huh." I'm like, "You fuckers are gonna be real sad when you see this DM in six years."

• 37:27Speaker 01

  Yeah, it's fuel.

• 37:28Speaker 00

  It's real fuel. Like, I'm on some real chip on shoulder, "I'm gonna fucking kill your mother shit."

• 37:33Speaker 01

  Well, you can't...

• 37:36Speaker 00

  When it comes to business. In real, no, I mean this.

• 37:39Speaker 01

  When it comes to everything.

• 37:40Speaker 00

  Like in real life, I don't want to kill your mother, but in business, I like, like when I watch athletes play, like, I love people that, like, I love Draymond Green. Like, that's who I am as an athlete. Fuck you at all costs, I don't give a fuck, fuck you.

• 37:55Speaker 01

  See, I think, I think it's everything, because if you don't have that attitude in other buckets of your life, it like, it's everything. It, you have to create an environment in your head that no matter what, you're gonna get it done.

• 38:08Speaker 00

  But real quick, and I'm, because your part ownership in Hawks is a good comp. The, I'm always fascinated by this. You're on the field, football game, right, it's a rough fucking sport, you're breaking people's fucking faces, triple zero, game over, everyone comes to the middle, and you're like, hey, how's Sarah been? I actually feel that in my business life, like, in the context of business, I'm gonna break your ankle, and like, I don't give a fuck, and fuck you, and I want the whole crowd. The reason I've become friendly with Novak Djokovic is like, he's one of the few people I've reached out to, ever, because I'm like, motherfucker, there is only one thing I see on earth right now that I completely wish I could do, which is be in center court at Wimbledon, against Roger Federer,

• 38:48Speaker 00

  and know every fucker in that stadium, and everybody who's watching, is rooting for Federer. When Novak goes into that zone, when he's like, basically like, fuck all of you, I get crazy. I, I, hairs on the back of my neck right now, and goosebumps. Novak, when he's against Federer, in center court in Wimbledon, like, happened this year, and the entire world is like, let's go Roger, let's go Roger. When he hits a big shot, and everyone goes quiet, the, the chemicals in my, like, all I want to do is be in that moment, because nothing excites me more to look at every single person in the crowd, of like, what's up with your boy, dick?

• 39:29Speaker 01

  Listen, if there's one thing we agree on, it's that. That's the way I'm wired. And I wa-

• 39:35Speaker 00

  What that does is it makes you not be scared of losing. You actually already set it up to enjoy the losing.

• 39:40Speaker 01

  When I took my book, Living with a Seal, to the publishers, I got 11 rejections. And all it did was make me be like, "I can't wait."

• 39:47Speaker 00

  My brother AJ and I have a sports representation business. We, we just went through a draft class, right? We got a ton of no's. When I tell you, "I can't wait to see those fuckers in real life in six years and look them dead in the..." I'm already doing it, because there's some kids that said no three years ago, that are already not doing as well as they thought they were gonna do, and their agents don't give a fuck about them anymore, because they're not gonna make any money, and I would've fucking taken care of them for life. I look at them dead in the face and say, "You fucked up, dick."

• 40:15Speaker 01

  Listen, anger is a really, uh-

• 40:18Speaker 00

  No, it's not anger.

• 40:19Speaker 01

  No, no, it doesn't sound angry to me, Gary.

• 40:21Speaker 00

  No, it's not.

• 40:23Speaker 01

  First you're gonna kill someone's mother, then you're gonna-

• 40:25Speaker 00

  It's sound- no, no, I know you're- no, no, it sounds wildly aggressive. It's actually unbelievably good oxygen for its deep merit-based competitiveness.

• 40:41Speaker 01

  It is. I think, listen, I think whatever you have to pull, whatever emotion you have to pull from. People say like, "Get rid of your anger, it's negative." I- anger to me is like fuel. I need a little anger, you know, it's fuel, I need it. It's a hard thing to channel consistently, and it, there's a nega- but you need it.

• 41:00Speaker 00

  It's funny, just to play out the story, to give context, because I think all these things have layers. It's funny, I'm not angry at any of these kids. I, I'm devastated for them. Which then manifests me like, like, it's like, it's like this incredible, like, all I wanna do is have dinner with 11 people that said no to your book and you. And like, just sit- I love that shit. I love, but I also like losing. Like, if you're gonna be that person, you also have to be the person that when you're wrong, you're like, "Man, you saw it, I didn't fucking see it, I'll take that L."

• 41:33Speaker 00

  So I love sports, bro. You win and lose. Entrepreneurship's hidden right now. Accu-hires, fake headline. Like, it's just not sports.

• 41:40Speaker 01

  Right.

• 41:41Speaker 00

  182 to 79. That's what it was. You know?

• 41:46Speaker 01

  Yeah, I mean, you can use bank accounts to score cards and that kind of thing.

• 41:49Speaker 00

  You can, but there's a lot of hiding. There's a lot of manipulation in that. We're just like, you're watching every... I wish everybody recorded every single action. Then you could see it more. Because that's what sports is. We're watching all of them. All the minutes.

• 42:04Speaker 01

  I think also, at the end of the day, we can talk about this. It was a great conversation. You know, going back to your question about entrepreneurs and what I see. At the end of the day, man, we humans, we all want the same thing. What do you think the one thing that we all want is?

• 42:18Speaker 00

  I think it's happiness.

• 42:21Speaker 01

  Exactly. We want to be happy. So if you're happy, all for it. You know, things make people hap... Different things make people happy. People are driven by different things.

• 42:30Speaker 00

  When you said, "My dad's a family man, plumber," you know, like, I was like, "So awesome." Like, because I know that. Like, I know so many, like, people that feel different. Like, to your point, there's 7,000 ways to be happy. This is about self-awareness of how you tick, not how you think you should tick.

• 42:45Speaker 01

  My brother asked me... My son is a swimmer. He's young, 10 years old. And my brother asked me how my son was doing at swim. And I said, you know, "He's doing really good, da-da-da, but he doesn't have the eye of the tiger."

• 42:58Speaker 00

  Yeah.

• 42:58Speaker 01

  And he's a great swimmer, but he just doesn't have... My brother said, "That's okay, as long as he's happy."

• 43:02Speaker 00

  Yep.

• 43:02Speaker 01

  And I'm like, "No." My son would be happy playing Minecraft and eating Haagen-Dazs every day in Fortnite on the couch. That's not what I want. I want him to be... to live up to his potential. And I don't see how anybody...

• 43:15Speaker 00

  But is that a different framework than where your parents went about it? I'm just curious. Because it was interesting to hear you... Like, when you just said that, I went back to the beginning of this podcast, thinking about the freedom your parents gave you. And were they into the guiding aspect? Is that why you were on a basketball team or not? I'm just curious.

• 43:31Speaker 01

  Their potential. So like when I look at myself and I'll answer it this way, I don't want to be the 80% version of me. Right? I don't want to grow up and be like, okay, you could have been built Vayner to this, but you only took it here.

• 43:41Speaker 00

  And that's you within yourself.

• 43:42Speaker 01

  I understand. I understand. My parents, their scorecard was how they raised their kids. That's what made them happy. My mom's whole life, I remember going to the grocery store and someone, my mom got into confrontation. I'm like, I can't believe my mother even has a life outside of our family that she would even react like this. Their whole life was about building my family.

• 44:04Speaker 00

  Yep.

• 44:04Speaker 01

  That was it. That's what made them happy.

• 44:06Speaker 00

  Yep.

• 44:07Speaker 01

  My life is bigger than that. Not in a bigger, it's just got more buckets. It's wider. So for my family, that's their happiness to them was taking care of their kids, putting them in college, giving them a car.

• 44:20Speaker 00

  I got it.

• 44:20Speaker 01

  And for me, it's, I want a number one, my standards are high, man. I don't want to write a book. I want a bestseller.

• 44:27Speaker 00

  But do you want to impose that on your children?

• 44:29Speaker 01

  My children.

• 44:30Speaker 00

  For me, when you went there, I'm like, I have no interest in my kids taking on my characteristics in any shape or form. I just want them to be in love and respect their characteristics as much as I do mine.

• 44:44Speaker 01

  Oh, that's fantastic.

• 44:46Speaker 00

  And I, to your point, everybody does it their own way. I'm just curious where you're going with it.

• 44:50Speaker 01

  My kids are on their own journey and because I used to play basketball till midnight every night and my son wants to play Fortnite. I can't tell him to go play basketball. They're on their own journey, but I do want them to live up to their potential. I just sat with a financial advisor and he said to me, what would you rather give your kids? A boatload of money or a boatload of life experiences? I want my kids to experience and see what they like.

• 45:14Speaker 00

  On their terms or yours?

• 45:15Speaker 01

  On, on both. Like I want to, no, I want to give them the opportunity.

• 45:20Speaker 00

  It's amazing. By the way, first of all, while we're talking about this, because a lot of people are listening, I have 0.00 interest in ever getting into anyone's actual personal way of parenting. Cause that's, everyone's got their own uniqueness and they should. I love the macro conversation of this game because where I go into this is.

• 45:42Speaker 00

  Kids are living in a reality that is intuitive to where their world is going versus the world we came from. I think so much about esports for that reason. It's changed the last 24 to 36 months, but the demonization of parents, and you're not doing that, but I'm just, I'm using this as an example. There are a ton of parents out there who have taken their kids out of the path of becoming all-time great professional esports players because they deemed that not being a thing. And I think about that every day.

• 46:12Speaker 01

  My parenting's a work in progress, guys. I'm figuring it out as I go. I don't, you know, I have four kids, they're all under 10.

• 46:18Speaker 00

  Like, I'm curious about Fortnite all day and Haagandas as actually being the stepping stone to actually winning, to actually getting full fulfillment. I really believe that. Like, I'm debating it for myself. I'm fascinated by that. Because, because I, and it sounds like you too for that matter, I didn't do anything that gave people confidence that I was up to something.

• 46:38Speaker 00

  When I was 11, I was doing everything off the reservation. I was an immigrant kid. Everybody had to get good grades. I was getting Fs. I never clicked into wanting good grades for myself. I clicked into, this is all horseshit. And, and I, and I always wonder, what are the 10 and 12-year-olds thinking right now that we can't see? And I feel like some of them are exactly where I was, and I think about that.

• 47:02Speaker 01

  Listen, again, I think I can always speak for myself. And just so you guys know, my kids have glitches just like your kids have glitches.

• 47:10Speaker 00

  Everyone's got glitches.

• 47:11Speaker 01

  You know, it's like, you think, oh, you sold a company. It's like, I have the same. My kids don't get out of the carpool line because they have anxiety. The same kind of stuff everybody deals with. And, I don't know. I just know that I want to give them as much opportunity.

• 47:23Speaker 00

  Yes, honestly, you'll appreciate this. I'm not even talking, I want to take even the four of them out of the equation. I just think you're a creative thinker, and it's just an interesting conversation for me. You know, just, I think we're at an interesting time. I, I think people are in deep shit in thinking they know where the world's gonna be in 15 to 20 years. When I think about what 5G is gonna do as an infrastructure, and what that opens up, you got fucking Elon Musk today talking about like, living on Mars. Like, people are like, people don't get it. Like, like, we FaceTimed people in fucking China, and it costs zero dollars. The people that were making decisions for us didn't have phones that got off a wall.

• 48:01Speaker 00

  Like, like, it's fucking crazy out here. And it's about to get wildly crazier. You think technology's advanced now? This is dogshit. This is a fucking pager.

• 48:11Speaker 01

  I agree.

• 48:12Speaker 00

  I know you agree. So, we're imposing today's reality against kids that are gonna live in a world that's 15 years from now looks nothing like today. And we must hedge for that in when we think about shit.

• 48:28Speaker 01

  Gary's president.

• 48:30Speaker 00

  But you know what I mean? It's an interesting, it's fun. I know that makes sense to you. We're byproducts of that.

• 48:35Speaker 01

  Yeah, it's interesting.

• 48:36Speaker 00

  White kids talking about rap in 1985 in fucking Long Island. Rap wasn't even a fucking genre to people. It was a fad. Rock and roll. The internet was a fad. People laughed at my fucking father when I launched an e-commerce wine business. The internet was a fad. Fuck TikTok and Vine. The whole fucking thing was a fad. Do you understand what's coming? Fuck.

• 48:59Speaker 00

  Parting, parting shots. What do you want people to know? You got a lot of people listening.

• 49:03Speaker 01

  Well, first of all, I want to thank you for the opportunities. This is super cool. I've been wanting to do this for a long time.

• 49:07Speaker 00

  Me too, I'm glad we did it.

• 49:07Speaker 01

  You know, we connect once in a while, but it's good to sit with you.

• 49:09Speaker 00

  Brandon, it's good to see you too.

• 49:10Speaker 01

  I like to arm wrestle you.

• 49:11Speaker 00

  How's Vayner Speakers going? Okay, we'll do that. How's, uh?

• 49:15Speaker 01

  Pay-per-view.

• 49:16Speaker 00

  How's, uh? How's Vayner Speakers going? One thing that everybody should know is, I think you guys saw about 16 months ago we started Vayner Speakers. I teamed up with my agent at CA, Zach Nadler. He's now the CEO of that. It's been really fun. He's actually in the room while we're talking. And one of the key targets for us was Jesse because we were looking at things that... Arbitrage. Who is way better than people realize at this exact second? They are at this thing. So, it's exciting that you're with us. Straight talk, because that's what I love about you. How's it going?

• 49:50Speaker 01

  It's been great. Zach's been amazing. I was hesitant to do it because I was getting a lot of... Yeah, so I mean, just so you guys know, I started speaking about three years ago. I wrote a book. The book became a number one bestseller. It was amazing. But it launched me in a completely different direction than I anticipated. I started getting asked to speak. And the first speaking event I went to, there were 40 people, no microphone. The guy... Said to me, speak loudly and slowly, you have forty-five minutes. And that has led to, you know, much bigger stages. And I did it all myself for two years and then Gary texted me and said, I don't even remember this. I'm starting this thing and you know, I saw you speak, you were great or whatever. And introduced me to Zach and um.

• 50:31Speaker 00

  What goes through the process? Like, why am I getting the gig? I get so much in about myself. Like, how are you thinking about it?

• 50:35Speaker 01

  The process for me was, you know, can I do this myself? I'm doing it myself and it was, it became an easy decision for me. Because I fell in love with Zach and you know, you handpicked Zach and, and, and what you guys do at Vayner Speakers. And I weighed it all and it became super simple for me. Um, and it's been a really good process. Listen. After I sold my last business, I'm like, I'm never having partners again.

• 51:00Speaker 00

  Right.

• 51:00Speaker 01

  I don't want partners. I want freedom.

• 51:02Speaker 00

  Right.

• 51:03Speaker 01

  You'd work so you get freedom.

• 51:04Speaker 00

  Correct.

• 51:05Speaker 01

  And I have a partner with partnership with you guys and it's been really, it's been really good and I'm.

• 51:11Speaker 00

  What's been the most surprising thing? I like learning.

• 51:14Speaker 01

  Um.

• 51:17Speaker 01

  It's just, there hasn't been really those big surprises. It, you know. You guys laid out exactly what it was been and it hasn't, we've been able to.

• 51:24Speaker 00

  The surprises that you could deliver on the hyper.

• 51:26Speaker 01

  For the first time, like, this is what we're gonna do and we're gonna do it. And when I was disappointed in certain things.

• 51:31Speaker 00

  Yep.

• 51:32Speaker 01

  I would say to Zach, like, I want something bigger. I need more and, and you know, and he would respond. So. Um, yeah, it's been really.

• 51:39Speaker 00

  You like it? You like speaking?

• 51:40Speaker 01

  I love it.

• 51:41Speaker 00

  Yeah, me too.

• 51:41Speaker 01

  I wouldn't do it if I didn't like it.

• 51:43Speaker 00

  Yeah, I understand.

• 51:44Speaker 01

  Yeah, as you get older, man, it's like, you, you, you only have two buckets, Gary. You got um aggravation versus reward. And I want low aggravation for the most amount of reward. If something's high aggravation, even high reward, I'm not doing it. And you guys have made it low aggravation.

• 52:00Speaker 00

  You know what's funny, Jess? If you, I and many others can get people to realize you don't have to wait to fifty. And some success to put yourself in a position for that and you could actually do that at twenty-two. You'll just have to be a little patient and a little more humble, but you could be way happier. You and I in a lot of ways did do that, which is what I think led to this. And I think a lot more people can do it, but they have all these expectations of what they're supposed to do from twenty-two to thirty and it fucks them up.

• 52:30Speaker 01

  It's true, and just to add on about the speaking, because I just, you know, I've talked about walking in and speaking in front of 40 people. And then, you know, as entrepreneurs, man, it's okay to start small. And I just want to say-

• 52:43Speaker 00

  The first- go ahead, I'm sorry.

• 52:44Speaker 01

  It's okay to start small. You start small, you think big, you scale it fast. Something my wife always says, "You start small, think big, and scale it fast." And that's the way we've been able to do it. It feels really authentic and grassrootsy.

• 52:57Speaker 00

  When I wanted to get into tech, the first five public things, meetups, events, I did, this is in 2009, when Wine Library had gone from 3 to 60 million. The first five things I did was cold email conferences in the tech world and offer to set up a table and pour wine. I was a bartender at the first, a Robert Scoble Jiaku event, a Technoradi conference. I literally, the first five of it, I found a picture of me and AJ recently at a tech cocktail event, which was a DC meetup. I was the help. That was after real success.

• 53:40Speaker 00

  Most people don't have the humility to do that with no success.

• 53:45Speaker 01

  Yeah, that's what it is.

• 53:47Speaker 00

  Eighteen couches.

• 53:48Speaker 01

  Eighteen couches, brother.

• 53:49Speaker 00

  Love it, brother. Thanks for being on. Let's clap it up for Jess.

• 53:54Speaker 00

  I think Eighteen Couches could be a really, I think Eighteen Couches could be a real framework for either a book or a talk, because I really think, and you saw I zoned in on it, I think if you can go deep, in the way that I've gotten deep into like fear and insecure, like if you go deep into the network you built, which then became the foundation of everything you've pulled off, and the pattern recognition of human arbitrage when you over-deliver and you ask for less in return, I think there's a real unlock there for you. And I think the framework of Eighteen Couches could be a really cool starting point.

• 54:26Speaker 01

  Yeah, and the mindset of me when I was on Eighteen Couches was, "I'm a millionaire. They just haven't paid me yet." That's how I was thinking. That's how I was thinking.

• 54:33Speaker 00

  Bro, I've owned the Jets for a long time.

• 54:35Speaker 01

  Right, exactly. That's a tough, that's a tough one, though.

• 54:38Speaker 00

  I'm gonna pull it off. Everybody, if you enjoyed this podcast, please go back and look at the prior episodes. They're loaded. I appreciate your attention, and thanks for being part of this journey. See you later.