Why Execution is the Game of Entrepreneurship with Jesse Itzler

11 Jun 2026 · 55 min · 28 chapters

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In short

Jesse Itzler discusses entrepreneurship as “execution,” arguing that success comes from long timelines, relentless follow-through, and building value through relationships and momentum—not quick hacks or empty “win-win” deals.

Guest backgrounds

Jesse Itzler is a serial entrepreneur from Long Island, educated at American University. He started in the music business as a signed rapper (Delicious Vinyl, signed in 1990; dropped after a year). After writing the New York Knicks theme “Go New York Go,” he built a sports-theme-songs business, then later co-founded a private-jet company concept that became NetJets-style jet cards. He also became known for coconut-water entrepreneurship (partnered with Zico; sold to Coca-Cola) and is a part-owner of the Atlanta Hawks.

Key claims

execution beats speed-to-money; foundations take years; people buy stories/people/momentum; “put yourself in the room” creates luck; ask for “no-lose” asks; you must truly want the goal (obstacles don’t matter).

Notable examples

sleeping on 18 couches; buying playoff tickets on a credit card; selling theme-song compilations (~1M units); NetJets meeting after being rejected in 12 minutes; coconut water training for a 100-mile race; first Marquee Jet sale via TED coffee-shop muffin strategy; DM/relationship value and “no-lose” collaboration pitches.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Jesse Itzler's Journey: From Rapper to Entrepreneur

0:45 to 4:12

Jesse shares his early life, music career, and entrepreneurial spirit.

“i was a white rapper believe it or not i'm aware i can see it uh for everybody who's listening you'll hear some laughs in the background and things that nature we're here at an off-site kind of conference thing.”

The Role of Parenting in Shaping Entrepreneurs

4:12 to 6:06

Jesse discusses how his parents influenced his approach to effort and success.

“My dad didn't even get that deep into it.”

Finding Passion at the Intersection

6:06 to 8:59

Jesse talks about discovering his passion for sports and music through entrepreneurship.

“And I wrote a theme song for the New York Knicks.”

The Birth of the Private Jet Business

8:59 to 11:16

Jesse explains how he ventured into the private jet industry after selling his first company.

“So all of a sudden I was like, Whoa, as an entrepreneur, you guys, we have a lot of entrepreneur in this, in this room.”

Sales Success and Understanding Relationships

11:16 to 14:01

Jesse reflects on the sales success of his jet company and the complexities of money and relationships.

“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.”

The Turning Point: From Wealth to Purpose

14:01 to 15:10

Jesse Itzler reflects on his life changes following financial success.

“And a year later we did$5 billion in sales.”

Training for a 100 Mile Run

15:11 to 16:52

Itzler shares his journey from couch to 100-mile race in 90 days.

“And then I decided that I didn't want to sell airplanes anymore.”

Coconut Water and Entrepreneurial Insights

16:53 to 17:55

He discusses discovering coconut water during his training for the race.

“When I got to mile 83, I had seven toenails floating around in my shoe.”

Zico: From Partnership to Profit

17:56 to 19:59

Itzler details his partnership with Zico and its eventual sale to Coca-Cola.

“So I partnered with a company called Zico, Z-I-C-O.”

Experiential Living and Business Culture

20:00 to 21:53

He discusses shifting to a more experiential life and business perspective.

“We're part owners of the Atlanta Hawks, which you know, we live in Atlanta and I got - Which is the epicenter of culture in America.”
Show all 28 chapters

The Time Investment in Entrepreneurship

21:54 to 23:01

Itzler emphasizes the long-term commitment required for building a brand.

“I think that a lot of entrepreneurs have been tricked into thinking that things happen quickly.”

Leveraging Relationships for Success

23:02 to 24:20

He explains the importance of relationships in achieving business goals.

“It's really cool to get the meeting with the jet company.”

Creating Opportunities in a Digital Age

24:21 to 26:24

Itzler discusses the power of social media to create opportunities.

“You put yourself in a position where you attract luck.”

The Value of Giving and Building Relationships

26:25 to 28:00

They discuss the need to create value and meaningful connections in business.

“real story right now for anybody listening not just people that happen to be in city areas where this shit could happen.”

Valuing Relationships in Entrepreneurship

28:00 to 29:25

Learn how to assess your value as a leader in various roles.

“how can I provide value as a husband, as a boss or whatever, in the long term, it's going to pay off.”

The Power of No-Lose Opportunities

29:25 to 30:50

Discover the concept of no-lose propositions in business outreach.

“now that you bring it up, the guy that does all my merch for my company, uh, 29 or 29, this race company we have DM to me.”

Understanding Rejection and Persistence

30:50 to 32:49

Hear about the importance of persistence and handling rejection in entrepreneurship.

“and they asked everyone to name three people that were alive they'd want to have dinner with.”

Challenges Faced by Entrepreneurs Today

32:49 to 34:53

Explore the struggles of modern entrepreneurs compared to the past.

“And I'm like, there's gotta be rich people at Ted.”

The True Desire Behind Entrepreneurship

34:53 to 36:29

Understand the deep motivations driving entrepreneurs beyond success.

“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.”

The Psychological Aspects of Achievement

36:29 to 37:44

Delve into the psychological factors impacting entrepreneurs' success.

“And I could say, if someone said to me, what's the silver bullet of being an entrepreneur?”

Embracing Competition in Business

37:44 to 39:40

Learn how embracing a competitive spirit fuels success in business.

“Athletes play Like I love people That like I love Draymond Green.”

Reflecting on Rejections and Growth

39:40 to 41:26

Hear insights on the value of learning from past rejections in business.

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

Finding Happiness in Entrepreneurship

41:26 to 42:00

Explore the different paths to happiness and fulfillment in life and business.

“you're like man you saw it, I didn't fucking see it I'll take that L so I love sports bro you win and lose, entrepreneurship's hidden right now Accu hires, fake headlines.”

The Pursuit of Happiness in Entrepreneurship

42:00 to 43:50

Discussing the fundamental human desire for happiness and its implications in entrepreneurship.

“I think also at the end of the day, and we can talk about this.”

Parenting and Potential

43:50 to 46:40

Exploring different parenting philosophies and the push for children to realize their potential.

“I just want them to be in love and respect their characteristics as much as I do mine.”

The Future Landscape for Kids

46:40 to 48:24

Examining how today's kids are navigating a rapidly changing world and the implications for their future.

“I never clicked into wanting good grades for myself.”

The Evolution of Speaking Engagements

48:24 to 49:44

A look into the journey of speaking professionally and the unexpected turns it can take.

“White kids talking about rap in 1985 in fucking Long Island, rap wasn't even a fucking genre to people.”

Starting Small and Thinking Big

49:44 to 52:54

The importance of starting small in business and growing with authenticity.

“Straight talk, because that's what I love about you.”
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Transcript

Automatic transcript. May contain errors.

0:00Jesse Itzler: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 going to let him frame it up for you and then I'm going to fire away with a bunch of questions. But first and foremost, Jess, thanks for being on. Thanks for having me. I appreciate it. So tell the Vayner Nation that's listening right now who you are. great well i'm a serial entrepreneur i started out in the music business i had uh i was signed to a record label called delicious final in the 90s what year did you sign i signed in 1990 i was 21 and what kind of artist were you don't laugh i was a rapper i'm not laughing i'm not laughing i was a white rapper believe it or not i'm aware i can see it uh for everybody who's listening you'll hear some laughs in the background and things that nature we're here at an off-site kind of conference thing.

0:57So we're just recording the podcast in between sessions. So keep going, Jess. So you're a rapper at 21.

1:04Jesse Itzler:Started out right... Where'd you grow up? I grew up in Long Island. And then I went to school in Washington, D.C. at American University. Got a record deal. Good test taker, maybe. I don't know about smart, but... Fair enough. Got a record deal right out of college after a lot of rejection. Signed to Delicious Final. Got dropped from the label a year later. Why? Um, 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, because I only had two things on my resume after that.

1:40Jesse Itzler:I was a kiddie pool attendant and I was a rapper. And that's not going to get you a lot of jobs. How did the rapper thing go down? How old are you? I'm going to be 52. Hey, you look great. So 52. So you're eight years older than me. So when does rap hit your radar? 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 um it's like that by run dmc sucker mcs by run dmc fell in love with it grew up in long island where hip-hop was like emerging fast yes and just got the bug so started out break dancing started out in the you know just doing whatever i could do this is a different era you know, mid 80s and just got into it.

2:24Jesse Itzler: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 at that time, I'd never been in a studio. Were you an entrepreneurial kid? I was an insane kid. Like I tried everything. My parents gave me a long leash and 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 didn't have a paper route. I was, no, but I was just, I was exploring. You were not looking to make money? I was looking for adventure, man. I was looking for fun and I still am, but I was never really wired for, to make money.

3:01Jesse Itzler:So what did your crew look like? Were you like a skateboard kid too? I was, I was athletic. Okay. Um, I was artistic. I was a good storyteller and, um, I wasn't scared. I wasn't scared to fail. I wasn't I'm scared to try. Because my parents really just supported my effort. They praised my effort and not the results. Did they acknowledge when you failed? 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.

3:36Where 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.

3:48Jesse Itzler:Well, I think the fine line in between those two points is disappointment. And I think disappointment's been stripped from kids. I agree. There's participation trophies. Right. You know, everyone's on it. You know, you can make the team. So your parents on the way home of losing a game 42 to 16 were like, hey, I really appreciate the fact that you were down by 30, that you were going hard. But in the same token, they weren't making excuses or saying you're going to be Michael fucking Jordan. Yeah, but 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.

4:18Jesse Itzler:He watched it and then he went and he sold plumbing supplies. Did he talk? Of course he talked, but it wasn't about like raising this kid that's going to go to Harvard or that's going to be an amazing athlete. It was like letting you go. You went hard and you get in the car and he says, good job, kid. He says, how'd you feel about it? Okay, that's a really good thing. Yeah, and then I said, I feel terrible. We got blown out. Right. 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 that put any kind of pressure on me to succeed.

4:51Jesse Itzler:He was a family guy. He still is. And it was just about that. And mom? Teacher and then raised four kids. And what was she saying to you? Same thing. It was just. She said, 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 it was like 16 when I first realized, wait a minute, I'm not the best looking person on earth. Like, like, you know, like, like, was she like that kind of mom? She was, she, they really gave me my distance and they let me figure it out. What number were you in the kids? I was the bottom four.

5:27Got it. It's cool though.

5:29Jesse Itzler:It's very cool. It is cool. Like they've been through enough reps where I'm sure you're, is it a sister or brother that's the oldest? Brother. Had it slightly different. 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. By not putting the pressure on me. They made me want it for me. Like it can't be my parents' dream. It would have to be my dream. I get it. And they never, I remember when I wanted to get good grades for 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.

6:03Jesse Itzler:So they took the pressure off of me. The freedom created the results. It was my goal. it was my dream so now you get signed tell them about the new york dick song i get signed to this label called delicious vinyl i wrote a couple of songs for an artist named tone loke i get dropped from the label a year later i moved 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 um my wife always says this is 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.

6:38Jesse Itzler: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. You asked me if I was into money. Not real. 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. 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.

7:18But I probably heard that song 8 ,000 times. 7 ,800 of them were in a four-week period in 1994. Yes. It was insane.

7:31Jesse Itzler:It was insane. and like that became your like tell me living that moment where like gene 1994 uh 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 like are you just walking around life and before you even say hi you telling people that you wrote that fucking song i would be yeah well it was interesting because at that point in my life i slept on 18 different couches yep so i had 18 different friends I bounced around for a week here at a 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 it was big and big, big in New York, uncomfortably big.

8:15Jesse Itzler:Yeah. And, um, I didn't really know how to handle that, you know, but, um, 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. That's cool. 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 that was what you wanted to stand for i still do anything like there's no obstacle there's no business there's no goal there's no race so how much in playoff tickets do you end up spending um enough that it could it set me back yeah but but again those seeds, those seeds, you know, were planted.

9:00Jesse Itzler:Yeah. They paid off later. So what happened next? So all of a sudden I was like, Whoa, as an entrepreneur, you guys, we have a lot of entrepreneur in this, in this room. Um, you realize that you look for something that differentiates yourself. And this was a big def 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. Interesting. And I'm like, I ended up doing almost every team.

9:33Jesse Itzler:And then I sold that company. In the NBA? NBA and some baseball and football. What was the most next famous song? Well, what happened was the songs became somewhat popular in each region, but that I turned it into selling them as a compilation with all the songs. That I understand, but in its own region, I mean. Chicago, because Jordan came back. There was a 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. And in that transaction, did you make some money? Yes. Did you have to work there for a little bit? I worked. We had an earn out.

10:07Jesse Itzler:So I worked there for a year and a half and then we hit the earn out. Talk to me about that year and a half. Well, in our contract, they paid us a couple of million dollars up front, but we had a$16 million 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 everything was about 364 more days man we got to hit this number every day was a countdown yeah and uh that's how I mean and we hit it so you're wildly motivated interest aligned yeah day you hit it you're out what happens next now you have some money what happens next how old are you I'm 20 at the time maybe 26 and you have some money like way more than you ever had before yeah anyone in my family and do you go crazy do you do some shit what do you do no i mean my life my life was is pretty simple it's pretty simple then pretty simple now but um i was still 26 27 years old but what happened was the guy that bought our company had a timeshare on a private jet and he invited me at 27 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 of the wizard of Oz when everything goes from black and white to color.

11:16It's like, what?

11:18Jesse Itzler:People fly like this. I was like, you gotta be kidding me. I want to 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. Who was that partner? Uh, his name is Kenny Dichter. And we took that idea to, and how did you meet Kenny? Kenny was, so I own the trademark to all these themes. The songs 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.

11:50Jesse Itzler: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 the 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 check company. He was like, definitely. And we took a meeting with a company called NetJets owned by Warren Buffett, the largest private jet company in the world. How did you get to that meeting? This is a crazy story, man. The president of NetJets daughter had a sweet 16 and Christina Aguilera was performing.

12:29Jesse Itzler:And through somebody that knew me, they knew that I knew the manager and called up and like this guy wants to do something special for his daughter. and like I said, nothing's 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, 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.

13:06Jesse Itzler: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 I 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 a hundred PowerPoints and entrepreneurs have to differentiate.

13:43Jesse Itzler: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 from Run DMC, a powerful female 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. Then what happens?

14:12Jesse Itzler: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 and 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.

14:51Jesse Itzler: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? What do you want to do? I mean, like people go to Studio 54, try to get to Studio 54. I'm like, let's go to Hawaii tonight. So I had a great decade.

15:09Jesse Itzler:Fair enough. And then what happened? And then I decided that I didn't want to sell airplanes anymore. Like that wasn't, 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?

15:50Jesse Itzler:And it came back with a year. Everything came back with a year. How did that even hit your radar to enter? I went through a crazy period of time and I was thinking about giving all my money away. I was thinking about charity. I was just like, I just, you know, just trying to figure it out, trying to figure it out. And I was like, I want to do something big for charity. And like, I don't want to have a bake sale or a golf outing. My friends were all having like foursomes. I don't want to, I'm not a foursome guy. So I'm like, relax.

16:19Jesse Itzler:Just trying to help the kids at home. I want to run a hundred miles without stopping. yeah so i was 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 what year was this this was in 2008 six 2006 six. Because when you run 100 miles, it's like, how many calories does that take in an hour?

16:55Jesse Itzler: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 have photos of you in that wheelchair yeah you ever post it yeah that's a good one yeah I have a whole did a documentary on it you know 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 can Bro, I can't even spell coconut water.

17:49Jesse Itzler:Right. Okay, so you can go. I get it. Keep going. You would have been a great partner for me. Clearly. 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 i got married i married an entrepreneur my own my wife owns a company called spanks uh which is a big deal here in the states sure is and internationally too and um and that's where i am and then what um i started shifting my life to think about changing my show to and then what with the movie.

18:39Jesse Itzler:Go ahead. 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. You just put the energy into a different bucket. The energy was actually always there, but I started really obsessing on experiences and just really obsessing on almost like living a manic life. Is that how you ended up in Atlanta, the Coke transaction? No, my wife's business is in Atlanta. Understood. But I shifted after these sales to like really becoming more experiential and being intentional about how I live my life.

19:16Jesse Itzler:Was the coconut water sale? 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 Giselle and Kelly Ripa, Eminem, and take money in as investors in exchange for equity, for doing more stuff. Like 50 cents got equity. Yep. And vitamin. And vitamin water. These guys wrote checks. So it was really authentic. Yep. 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.

19:58Jesse Itzler: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 and I got - Which is the epicenter of culture in America. Yeah. Maybe the world, even for that matter. Yeah. 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 in importance of business, because I think business is a by-product of what is established in culture. Popular culture in America starts in Atlanta. I really believe that. It's an amazing city. When I think about what hip hop actually means to the world and where the innovation and it's just, it's an, 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.

20:48Um, it's just a really interesting time in Atlanta. Yeah.

20:51Jesse Itzler: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. That's right. What do you think, 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.

21:27I think we have more similarities than we don't, but obviously we have differences. It's what leads me to this question. 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. What's like on your radar as a consumer of energy around shit like this?

21:57Jesse Itzler: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'm going to live 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 - That's in the speed of your execution. I just feel like I've done 200 years worth of stuff in 50 years.

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22:30Jesse Itzler:But I feel like entrepreneurs 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 that leads to disappointment. Like it takes time and that's okay to build the foundations of a long lasting business. I think what we've glossed over, and you touched on it lightly with the tickets, is a lot of your execution. 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.

23:10You built up equity through relationships, which takes time to be able to convert that energy for that execution.

23:16Jesse Itzler:Yeah. Yes. Right? Yeah. I mean, why did Carl Banks and Ron and all these people, why did they go? I'm going to tell you why. I'm going to tell you why. Because people buy into stories, people, and momentum more than products. Always. 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. 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.

23:56It'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 run 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.

24:18Jesse Itzler: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. Cause 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, this is where everyone is. You don't have to have a room at the hotel to come to here for lunch.

24:51Jesse Itzler: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're here again, you look great. 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 buy you for five minutes let me interrupt I apologize it's the name of the show thank you very much what scares the fuck out of me is how unbelievably true that is how an eight dollar 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.

25:55What 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 bumble fuck Iowa listen to these two right now and not realizing what they do have 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 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.

26:36The serendipity of creating that for you now is literally, 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 DMed a bunch of people. I haven't gotten my music out there or sold my t-shirt. I'm crazy. And I reply, I'm like, hey Carl, with three followers. I'm like, how many people have you DMed? They're like 29. I'm like, go fuck yourself. you sat there for fucking 12 15 hours a day i think can i add on to that you can do anything

27:12Jesse Itzler:you want so i think a lot of people do send dms don't even actually know how to send the proper dm i agree so people by the way real quick because i'm going to add on to it there's been plenty of people that went to the right places that lost oh you had the right tack to start the conversation with russell simmons i 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. When I write an email. People roll up on me, I apologize, 99.999 % of the time to tell me what I can do for them.

27:50Yeah.

27:51Jesse Itzler: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 - As humans. 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 going to pay off. And always you won't, you won't have the ability to pick up all the opportunities. Right. One thing that I do that really helps me, helps me. I asked myself a very simple question. Would I recommend myself as fill in the blank? Would I recommend myself as a dad, as a CEO, as a business partner? And if the answer is no, why and what am I doing wrong?

28:26Jesse Itzler:When it comes to DMs, I feel like people want to know, like what's in it for me so if 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 real quick yep and what we're painting for everybody who's listening is look the fucking internet has given everybody an at bat. It doesn't mean that you can hit a fastball.

29:03And 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.

29:15Jesse Itzler: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, email, 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, uh, 29 or 29, this race company we have DM to me. And you know what he said? He created a win-win. I'm sorry. He created a no lose. Win-wins don't work because if I say a win-win, wait, you talk about this too? No, no. I like where you're going. When you have a win-win, Gary might win here and I might win here. That's not a win-win.

29:51Jesse Itzler:That's a Gary's dominating the win. A no loses. Oh, there's no risk I can't lose. He sent me a DM and he 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 these amazing product line. And I'm like, done. Hundreds of thousands of dollars later. 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. Okay, that's amazing.

30:26Like, if you think about it, that sounds win-win. No loses. 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. Yeah.

30:43Jesse Itzler:Action. Always action. I invited, 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. I knew two of them.

31:16Jesse Itzler:And people are like, how did you get Rakim, man? How did you get Big Daddy Kane? and I'm like, I asked them in a no lose and they came. People want to help people. 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. You're right. On the flip side, it's also how you got there because the 21 year old you that had nothing was willing to ask a hundred people to get one yes. Yes. 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.

31:58And 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. I still do it. Me too, which is why I'm saying it again. Yeah. 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.

32:41Like, you've got it so easy right now.

32:45Jesse Itzler: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 right but I had to go where rich people were I didn't we didn't have you had a pager? a what? did you have a pager in 99? I had a pager I probably had like but there was no but you had that pager to like act cool I had to show up 100 % I didn't like I had no email list and I heard about this event called TED this conference called TED in Monterey California.

33:19Jesse Itzler:And 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, well, 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 realized 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 stole.

33:54Jesse Itzler:No, I bought every single muffin in the store. I controlled all the muffin inventory in Monterey, California. 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, I'm so sorry. I overheard you. I actually have a muffin. I have 450 muffins would you want one he's like well he's like no no no you can take one I says well what do you do we start talking I said I want a jet company he goes get out of here he's like I'm actually in 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.

34:31Jesse Itzler:Qualified you can sit wherever you want to swim man absolutely and he was my first sale Josh Koppelman from half.com and And that's how my first sale. 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 does it matter with people? like back to nothing is impossible well the internet has made it uncomfortably easy and yet people are losing fuck you i think it goes back down to what i said earlier even deeper than the dms gary good is is negotiating your goals and i think you asked me about entrepreneurship and i said you know people want to get happen quicker and speed up the process and this and that.

35:34Jesse Itzler:But I also think it's easy to negotiate your goals. It's easy now to say like, oh, I'm not going to do this. I'm going to try this. I'm going to throw. And like, people don't stick with things. Most people do 95 % of the same thing. 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 through. 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.

36:06They 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.

36:23Jesse Itzler: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. but 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.

36:55Jesse Itzler:So if you do 400 DMs and they don't hit, it doesn't mean anything. You're on DM one. It starts with one. 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 Yeah it's fuel It's real fuel Like I'm on some Real chip on shoulder I'm gonna fucking Kill your mother shit Well you can't When it comes to business No No I mean this When it comes to everything Like in real life I don't wanna kill your mother But in business Like when I watch Athletes play Like I love people That like I love Draymond Green.

37:49Like that's who I am as an athlete. Fuck you at all costs. I don't give a fuck. Fuck you.

37:55Jesse Itzler: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's, you have to create an environment in your head that no matter what, you're going to get it done. But real quick, and I'm, because your part ownership in the Hawks is a good comp. The, I'm always fascinated by this. You're on the field football game, right? that'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.

38:28Like 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 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.

39:00I have heroes 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 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?

39:29Jesse Itzler:Listen, if there's one thing we agree on, it's that. That's the way I'm wired. And I mean, that's the way. What that does is it makes you not be scared of losing. You actually already set it up to enjoy the losing. 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 my brother aj and i have a sports representation business we we just went through a draft class right we got a ton of nose when i tell you i can't wait to see those fuckers in real life in six years and look them dead and 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 going to do and their agents don't give a fuck about them anymore because they're not going to make any money and I would have fucking taken care of them for life, I look at them dead in the face and say, you fucked up, dick.

40:16Jesse Itzler:Listen, anger is a really, uh. No, it's not anger. No, no, it doesn't sound angry to me, Gary. First you're gonna kill someone's mother. It sounds, no, no, I know you're, no, no, it sounds wildly aggressive. It's actually unbelievably good oxygen for its deep merit-based competitiveness. it is i think listen i think you 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 negative but it's funny 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'm i'm devastated for them which then manifests me like it's like this incredible like all I want to 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 going to 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 so I love sports bro you win and lose, entrepreneurship's hidden right now Accu hires, fake headlines.

41:39Like, it's just not sports. Right. 182 to 79. That's what it was. You know?

41:46Jesse Itzler:Yeah, I mean, there's score. You can use bank accounts as scorecards and that kind of thing. You can, but there's a lot of hiding. There's a lot of manipulation in that where 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. I think also at the end of the day, and we can talk about this. This is 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?

42:19I think it's happiness.

42:21Jesse Itzler:Exactly. We want to be happy. So if you're happy, all for it. You know, things make people happy. Different things make people happy. People are driven by different things. 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 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 his swim and I said you know he's doing really good but he doesn't have the eye of the tiger and he's a great swimmer but he just doesn't have my brother said that's okay as long as he's happy and I'm like no My son would be happy playing Minecraft and eating Haagen-Dazs every day and Fortnite on the couch.

43:09Jesse Itzler:That's not what I want. I want him to live up to his potential. And I don't see how anybody - But is that a different framework than the way 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, think about the freedom your parents gave you and were they into the guiding aspect? Is that why you run a basketball team or not? I'm just curious. 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 or whatever within yourself I understand you know 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 this 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 yep that was it that's what made them happy yep my life is bigger than that not in a bigger difference 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 i got it 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 but do you want to impose that on your children So 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.

44:39I just want them to be in love and respect their characteristics as much as I do mine.

44:44Jesse Itzler:Oh, that's fantastic. And to your point, everybody does their own way. I'm just curious where you're going with it. 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. all 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 on their terms or yours on on both like i want to know i want to give them the opportunity it's amazing by the way first of all while we're talking about this because a lot of people listening i have 0.00 zero interest in ever getting into anyone's actual personal way of parenting because 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 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 and 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.

45:59There 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've deemed that not being a thing, and I think about that every day.

46:12Jesse Itzler: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. Like, I'm curious about Fortnite all day in Haagen-Dazs 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 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. When I was 11, I was doing everything off the reservation. I was an immigrant kid. Everybody had to get good grades.

46:43I was getting Fs. I never clicked into wanting good grades for myself. I clicked into this is all horseshit. 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

47:02Jesse Itzler:listen again I think I can only speak for myself and just so you guys know my kids have glitches just like your kids have glitches everyone's got glitches you know it's like you think you sold a company it's like I got 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. Honestly, you'll appreciate this. 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.

47:34I 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 we FaceTime 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. Like it's fucking crazy out here and it's about to get wildly crazier. You think technology's advanced now? This is dog shit. This is a fucking pager.

48:11Jesse Itzler:I agree. 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. Gary for president. But you know what I mean? It's fun. I know that makes sense to you. We're byproducts of that. 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.

48:52The whole fucking thing was a fad. Do you understand what's coming? Fuck.

49:00Parting shots. What do you want people to know? You got a lot of people listening.

49:02Jesse Itzler:Well, first of all, I want to thank you for the opportunity. This is super cool. I've been wanting to do this for a long time. I'm glad we did it. We connect once in a while, but it's good to sit with you. It's good to see you too. I like to arm wrestle you. How's Vayner speakers going? Okay, we'll do that. How's Vayner speakers going? How's Vayner speakers going? speakers going one thing that everybody should know is uh i think you guys saw about 16 months ago we started vayner speakers uh i uh i teamed up with my agent 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 uh 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 um so it's exciting that you're with us.

49:47Straight talk, because that's what I love about you. How's it going?

49:50Jesse Itzler:It's been great. Zach's been amazing. I was hesitant to do it because I was getting a lot. 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 and you have 45 minutes and that has led to you know much bigger stages and i did it all myself for two years and then gary text me and said i don't even remember this i'm starting this thing and you know i saw you speak you're great or whatever and introduced me to zach and um what goes through the process like why am i giving the process i get so much inbound myself like the process for me was you know can i do this myself i'm doing it myself and it was 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.

50:49Jesse Itzler:And I weighed it all and it became super simple for me. Um, and it's, it's been a really good process. Listen, after I sold my last business, I'm like, I'm never having partners again. Right. I don't want partners. I want freedom, right? You'd work. So you get freedom. Correct. And I have a partner with partnership with you guys. And it's been really good. What's been the most surprising thing I like learning?

51:17Jesse Itzler:It's just there hasn't been really no big surprises. You know, you guys laid out exactly what it has been and it hasn't. We've been able to talk. The surprises that you can deliver on the hyper bike. Yeah, it actually did. For the first time, this is what we're going to do and we're going to do it. And when I was disappointed in certain things, I would say to Zach, like, I want something bigger. I need more. And, you know, and he would respond. So, yeah, it's been really. You like it? Do you like speaking? I love it. Yeah, me too. I wouldn't do it if I didn't like it. Yeah, I understand. Yeah, as you get older, man, it's like you only have two buckets, Gary.

51:48You got aggravation versus reward.

51:52Jesse Itzler: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. You know what's funny, Jess? If you, I, and many others can get people to realize you don't have to wait to 50 and some success to put yourself in a position for that. And you can actually do that at 22. You'll just have to be a little patient and a little more humble, but you can 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 22 to 30, and it fucks them up.

52:30Jesse Itzler:It's true. And just to add on about the speaking, because I've talked about walking in and speaking in front of 40 people. and then you know you as entrepreneurs man it's okay to start small and i just want to say first go ahead i'm sorry 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 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 three to 60 million.

53:07The 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 JICU event, a Technorati 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. Most people don't have the humility to do that with no success. Yeah, that's what it is. 18 couches. 18 couches, brother. Love it, brother. Thanks for being on. Let's clap it up for Jessica. I think 18 couches could be a really, I think 18 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 insecurity, 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.

54:23And I think the framework of 18 couches could be a really cool starting point.

54:27Jesse Itzler:Yeah, and the mindset of me when I was on 18 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. Bro, I've owned the Jets for a long time. Right, exactly. That's a tough one though. 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.

From the publisher

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.


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