The Craziest Story Of My Life…

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Jesse Itzler shares a crazy story and the valuable lesson it taught him.

And I sit down, I go to this guy’s apartment, again I’m 21, in his apartment he’s got a swimming pool, artwork, and he says to me, “I would trade…”, this is exactly what he said to me, “I would trade everything that I have, I’ll trade everything I have for the one thing that you have”. And I’m like, “man, I’m f**king broke, what are you talking, me?” I remember when I was starting out, I was 21 years old, this is a crazy story. I just got dropped from a record label, I signed to a record label called Delicious Vinyl, I was a rapper. So my album doesn’t get picked, I don’t get picked up for a second album and I moved to New York City.

I have two things on my resume, kiddie pool attendant, because I was a kiddie pool attendant and rapper. So I’m staying on my friend’s couch, living on his couch with his roommate, and he tells me on Monday I got to get out of the apartment, so instead of going to look for a new apartment over the weekend, I go to my friend’s bachelor party on the Jersey Shore. I’m at the Bachelor party, I’m getting a drink at the bar and I see this girl, I start chatting with her, she asks me where I live, I told her, actually, as of Monday, I have nowhere to go.

She takes out a napkin, she writes her address on the napkin, I’m 21 years old, and she says, “if it’s an emergency on Monday and you’re stuck, you can come live with me”. Monday comes, I get kicked out of my friend’s apartment, I have nowhere to go, I’m like, this is an emergency. I take out the napkin and I live with this girl and her roommate for six months. Turns out that her father is a big entrepreneur businessman, he owns a piece of the Yankees, just like monster mogul. I write this song for the New York Knicks called “Go NY Go”, and it becomes a big success, it becomes a big hit, and I just realized that there’s an opportunity to write theme songs for all these professional sports teams, but I don’t have a penny to go in the studio, to do the demos, to shop them to the teams, so I need money.

So I go to this music guy and he says, “I’ll give you $10000 to go and do these songs for 10 percent of everything you make for the rest of your life”. He wants to buy me like a stock. For the rest of your life? For the rest of your life, everything you do? I will invest in you. You own an airplane business, he owns 10 percent. Yes. Forever? Yes, but I needed the 10 grand, so I said, “I’ll take it”. So before I take it, I go to this girl’s father for advice, this business mogul that I’m living with, and I sit down, I go to this guy’s apartment, again, I’m 21, in his apartment he’s got a swimming pool, artwork like, fancy…he’s macked out, man.

it’s like, I’ve never seen anything like this. And I go in and I tell him the story about the 10 grand, and he says to me, “I would trade…”, this is exactly what he said to me, “I would trade everything that I have, I’ll trade everything I have for the one thing that you have”. And I’m like, “man, I’m f**king broke, what are you talking me?” I go, “what’s that?” And he said, youth. Because he had already gone through the journey, even though he had everything, he already had gone through the process. He wasn’t that 20 year old that you’re talking about that whatever… he had gone through it, he had it all.

He missed the process, the journey of being, you coming up at 20 and not knowing like, here you are, but those were the years man. The first fight, the first this, like that’s what makes you like… and that stuck with me, man, at 21 years old, it stuck with me and I realized that, man, I got to enjoy the process. And it’s really never rubbed off on me, from me. So what did you end up doing? The second part of that conversation, he said, “will you make this work on your own?” I said, “I think I can”. He said, “I didn’t ask you if you can, will you make it work?” I said, “I will”. He said, “then go tell the guy to f**k off, and go make it work”. And I did.

Jesse Itzler

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